19 comments/ 58268 views/ 42 favorites His Son's Teacher Ch. 01 By: GillianCD ~1~ Dave Monet hated meeting his son's teachers for the first time. It was always awkward for one reason or another. Sometimes the teacher would be attractive and he could not help but stare, which he thought was disrespectful to his wife, now his ex-wife. Most of the time what he hated most of all was the not knowing what she would say about his son's behavior and/or academics. His son was the typical teenager, at 17 he cared more about cars, sports and girls than about academics and his future. But tonight was especially awkward. Eric had talked a lot about Ms. Stepford, the new social studies teacher. He had described her as a 'MILF', not too old but old enough that teenage boys were shocked they were attracted to her. Dave felt excited at the prospect of having a pretense to talk to an attractive woman. The numbness of his divorce was beginning to wear off, and he found himself missing the warmth of a woman. * * * Tiffany breathed a sigh of relief as Mr. Atkins' appointment ended and he got up and left. The other teachers said that tonight would be easy, that by high school most parents had become less involved in their kid's education seeing it now as their kid's responsibility and thus less inclined to come in and blame her. However, tonight, all of her parents were showing up at their regularly scheduled time. Correction; all of her kid's fathers were showing up and mostly the ones from kids whose parents were divorced. It was the same story when they came in the door. She would stand and cross the room to greet them. They would look her over and she would let them, secretly she enjoyed all the male attention. It made her feel more feminine. However, they would inevitably lose interest. She should not have worn heels. Sure, she loved her new black platform pumps. However, it only added about six inches to her already tall 6'1". Therefore, as she waited for her next appointment, she slipped out of her shoes and let her feet take a break from the heels. There was a knock at the door, she looked up and saw a tall shadow through the narrow window slit of her door. Awkwardly she fumbled for her heels but it was too late, Mr. Monet was early and had entered her room. * * * Dave was not disappointed. The woman sitting at her desk was a pretty brunette wearing a black dress. It was made of a stretch fabric which combined with a split neckline gave a subtle hint of her curves. A princess waist only accentuated her hourglass figure. He was happy when she stood up; most teachers sat at their desk and made you cross the room to them. She had been playing footsy with something under her desk, and judging by her bare feet it had been her shoes and they had won. This gave him a chance to appreciate her legs. They were shapely and athletic and shimmered in expensive black nylons. He, correctly, imagined that they were thigh highs and that their lacey tops were attached to a garter belt. He found that he liked the fact that she was barefoot and that she was coming to him, and that he had stopped just inside the doorway forcing her to cross the length of her room. And she did, with a smile. She offered a hand and he shook it, her skin was soft, yet her grip was a little more strong and sure than he was used to in a woman. He found that her confidence was a strong balance to what he, again correctly, perceived as a natural submissiveness. * * * Tiffany blushed a little when Mr. Monet shook her hand, it was strong and firm as a man's shake should be. She looked him in the eyes and the strength she saw there made her look away. She glanced back up at him and smiled because he smirking, a self-satisfied smirk. Then she realized she was looking up at him. He was a good 6'5" and she was glad fate picked that moment for her brand new heel to break. "Pleased to meet you, Mr. Monet." She said showing him to his seat in front of her desk. "Please call me Dave." She had a strict rule about calling her kid's parents by their first name. She thought that it was unprofessional. "Alright, Dave." The name felt good on her lips. "I was hoping you'd come. Eric is one of my favorite students." "He is?" Dave was a little shocked. Eric being a mediocre student meant either he was a pain in the teacher's ass, or they did not really have anything to say about him. Tiffany giggled. "No really. He seems to really enjoy American history and he's always paying attention and engaged in class." "He is?" Again, Dave was a little shocked. Again, Tiffany giggled. She opened her desk drawer and leaned over to get Eric's folder from her locked file drawer. As she moved Dave caught a whiff of her perfume, it was Beautiful and it reminded him of an old girlfriend who wore that perfume in high school. Tiffany sat up straight and opened the folder. "Yes. This is his last test." He looked at the paper in disbelief. "104%?" "Yes, he missed one but got the bonus. He's getting straight A's in my class." * * * It had been the best thirty-minute parent teacher conference she had had tonight. Mr. Monet had been engaging and genuinely caring about his son. Then there was the spark. She felt a definite attraction and she thought that maybe it was mutual. Too bad her secret would not let her act on the attraction. * * * Dave smiled as he left her room. There was something about her that was different. She had a warmth and empathy that was different from other women he knew. He had noticed the coffee cup on her desk, her lips had left an imprint in red lipstick on the rim of the cup. It was from Kallisti's Coffee, a small coffee shop in the college district and the interns at his firm would bring coffee in from there. He thought that he should maybe start going there himself. * * * Tiffany got home and went straight to her bedroom. She was so horny and had to take care of business. She just could not get Dave...Mr. Monet...out of her head. She slipped out her dress and just let it drop to the floor. She was wearing a black and panty set and gartered thigh highs. She flopped on her bed, rolled on her back, and slid her hands into her panties. Her cock had become untucked on the drive home and now her 'clitty' was fully erect and she slowly started stroking herself. She closed her eyes and started to moan. She began rubbing her breast, the hormones she had taken had worked better than she and her doctor expected. She now had a decent set of C-cup breasts. Her nipples were almost as erect as her 'clitty'. Dave was all that was on her mind as she touched herself. She rolled over on all fours, reached into her nightstand, and pulled out a purple dildo from her nightstand. She lubed the toy and buried her face in her pillows as she jerked off and slowly slid the anal training toy into her ass. She thought about it being Dave's cock inside her, making her his girl. In minutes, she was cumming shooting her honey across the mattress. Slowly she took the toy out of her ass and looked at the mess she had made. It was cloudy and soaking into her sheets. She started slurping it up, another training regimen she had started when she moved to Portland. Eventually she would work up the courage to accept a man's invitation and get her V-card punched, and she wanted to be ready when that happened. Satisfied that she had slurped all she could from the sheets she swallowed and stripped the bed and put clean sheets on before hopping in the shower. ~2~ This would be the last time Dave would come to Kallisti's Coffee. The coffee was not as good as his interns raved, and the food was all right but nothing great. The only reason he had come here was it was on the way from dropping Eric off at his mother's house and the new apartment Dave had moved into across town. Moreover, he was hoping to see Ms. Stepford. He looked over and reading a book on the Korean War was Ms. Stepford. She was wearing a white, cowl necked sweater dress. After all, it was February in Portland. She was drinking what looked like cappuccino from a wide coffee mug, taking an occasional sip and not looking up from her book. As he waited for his cup of coffee, he admired the woman that he had come here to see. Once again, he could not take his eyes off her legs. They were clad in opaque, black leggings and she was wearing black suede, corset-tie high-heeled boots. He got his drink and screwed-up his courage. He crossed the coffee shop towards his target. Tiffany looked up as a shadow darkened her page, and was more than pleasantly surprised to see Mr. Monet. She smiled broadly. "Hello, Mr. Monet." She said standing and offering her hand. She was shocked when he took her hand and pressed it to his lips. "I said call me Dave." He said with a wolfish grin. "Okay...Dave." Tiffany blushed, finding herself at once at ease with him and off-balance. "Would...would you care to join me?" "I'd love to." He said taking the seat across from her. * * * They stayed at the coffee shop for about two hours before getting bored with the college environment. Dave suggested a bar he knew with an Irish pub motif and nice dark corners where they got lost in each other's eyes and stories. At some point, they stopped talking and started kissing. Dave was a slow kisser, drawing her close to him as their tongues danced. Soon his hands were sliding up her sides and then to her breasts. It felt so good to feel a man's hands on her breasts. However, once his hands started drifting south, she gently guided them back to her chest. She had dreamt of this moment since before she moved to Portland, since before she began the transformation. It was finally here, but as much as she was excited and living in the moment, she was terrified. Not only was she in the arms of a man for the first time, but it was the man she was crushing on. However, what terrified her was what would happen if he wanted to take it to the next level. Her secret would be out, and if he wanted to make an issue of it, she could lose her job. The obnoxious sound of a bell and the blinding light of the house lights caused them to break their kiss. She bit her lower lip and watched him as the waitress came over and handed him the check. She reached for his purse. "Hey, pretty lady, I've got this." He said and pulled out a $100 bill and gave it to the girl. "Keep the change." He slid out of the corner booth and offered her his hand. "My place?" He asked. "Sure." She knew she should not accept the offer, that she should not go back to his place. However, she could not control herself; she wanted this more than anything so she let him lead her out into the cold night and his Lexus. He opened the door for and she slid into the passenger seat. For his part, Dave was beaming as he shut the door and crossed to his side. He opened the door, slid in, and looked at his gorgeous date. She was checking her texts when he slid into the driver's seat. "I'm sorry, Dave." She said when he shut the door. He looked at her, his heart sinking. "Could...could you take me back to my car? My bff just texted me, some crisis with her boyfriend." "Oh..." the disappointment in his voice was thick. "Okay." He said as he pulled away from the curb. "I'm sorry." She said, sliding a hand on his knee. "I want to make it up to you." She leaned over and nibbled on his ear as her hand slowly made its way up his thigh before lightly squeezing his crotch. "Mmmmm...." He moaned as she kissed and rubbed him. He was shocked when she fumbled his belt loose before unbuttoning his pants and unzipping them, freeing his cock. "Wow!" Was all she said as she looked down at the large cock in her hands. It was about six inches long even though it was still flaccid. Her warm hands were making it stiffen as she held it. "Wow, yourself." He said breathlessly. "I wasn't expecting a hand job!" Tiffany giggled. "Who said anything about a hand job?" She said as she leaned over into his lap and began licking his head. Dave swerved in surprise as her warm, wet tongue touch his sensitive head. She giggled and then started licking the bottom of his shaft and massaging it with her lips. Cupping his balls, she started caressing them and tickling them with her fingernails. She smiled as he grew as she pleasured him. A drop of precum glistened in the streetlights as they drove down the street. "Ohhhh..." He moaned as she slid the cock into her mouth and started taking it deep. "Do...do you mind," he asked breathlessly, "we're close to my firm...can...can I pull into the garage?" She pulled off his cock just long enough to reply, "Yes". Her breath was warm on his head as she said the word. She had always been curious what it would be like, what it would taste like. The precum was a little salty compared to hers, but the cock did not really taste like anything. What she loved, and yes, she loved it, was the way his cock felt in her mouth. It was warm, alive and every twitch & moan she knew he was enjoying her effort. From this angle, she could not see where they were. All she knew was they were slowing down and then turned into what could have been a parking garage with how it went from dark to light. The car rolled to a stop and Dave fumbled to slide the shifter to park. He reclined his seat and rested his hand on her head. Despite his disappointment at her needing to go home, this date had gone well for him. He had had drinks with a lady who understood him, and was incredibly nonjudgmental. Sure, she liked the Rams over the Seahawks, but she seemed to genuinely enjoy football. And that was something. Now she was sucking his cock in his firm's parking garage. Dave's hands in her hair felt exquisite as he controlled the speed as she sucked him. His fingers intertwined in her hair, his grip was strong and tugged at her roots. Each time that he pushed down, he went in a little deeper. She was making little gurgling noises as the cockhead pushed past her gag reflex. She relaxed her throat and let the cock slide back into her throat. She began to dry heave, her throat spasming along his shaft. He held her there for a moment and then released her. She came off him, a thick rope of slobber linking her lips to his head. "Fuck, Tiff, I'm going to cum!" He shouted, and she immediately wrapped her lips around his glans. He twitched releasing strand after strand of hot cum into her mouth. About half of her reward shot straight down the back of her throat without her tasting it. The other half splattered her tongue and cheeks as she tasted his cum for the first time. It was salty like she was used, but also a little sweeter than she expected. It was also quite a bit thicker than her's. Slowly she swallowed. Lovingly, she kissed the tip of his penis and reverently slid it back in his underwear and zipped, buttoned and buckled his pants. She looked at herself in the small vanity minor of her visor. A small dab had tried to escape from the corner of her mouth, with a delicate pinky she pushed it into her mouth, making a show of it. "Don't want to waste a drop." She said, turning to him she could see the passion in his eyes. "That was amazing Tiff!" He said, leaning in to kiss and nibble on her neck. She moaned and rolled her head to one side, lost in the magic of the moment. "My turn." He said and quicker than she could react to stop him, his hand darted to her crotch. Her clitty had come untucked and was now fully erect. His hand squeezed and stroked it, but clumsily. He was no longer kissing her, but looking at her with a quizzical expression. She could not make out what he was thinking. "You...you have a cock!?!" Tiffany began to cry. (To be continued) His Son's Teacher Ch. 02 ~ 3 ~ "You...you have a cock!?!" Dave asked again. His date was crying in his passenger seat after giving him the best head of his life. So many thoughts went through his head. She was beautiful, how could she have a cock? Why couldn't he tell she was a he? Did this mean he was gay? She had smelled, felt and her lips even tasted like a woman...so did the cock really matter? Why was he thinking of her as a 'she' instead of a 'he'? Why couldn't he take his hand from her cock? Slowly he withdrew his hand, he had felt her lose arousal about the time she burst into tears and felt guilty. Tiffany started getting out of his car. "Tiff," his voice was soft, "don't go." It was a command wrapped in concern. She paused, the door opened a crack. She thought about it. So many of her transgendered friends talked about safety and security in cases like this. Most, she thought, would tell her to get out of the car and walk back to her car. After all, Dave was still a stranger and had just been thrown into emotional turmoil. She did not know how he would take it and what his response would be. It may be all right, but she may end up in the ER or worse. A few, would argue that she should follow her gut. After all, she did not know where she was and the streets at this hour could be dangerous for any woman especially one with her secret. She looked at him. His face was a mix of emotions. Confusion, fear, a little anger, but mostly concern. She closed her door. He backed out of his parking spot and left the garage. Kallisti's Coffee where she had left her car was a short drive from the garage and they passed the 10 minutes in a very awkward silence. As he pulled in behind her car, she started to get out, silently. "Tiff?" His voice stopped her as she was halfway out the door. "Yes Dave?" This time he was paying attention to the sound of her voice. It sounded sweet and feminine. "I'm sorry about back there." He had taken the 10 minutes to try to process what had happened. Nevertheless, he was only left with more questions. "I...I don't want you to go." This shocked her. She had taken his silence as rejection. "You don't? Even now that you know what I am?" He smiled. "I have lots of questions, some I need answered. You've thrown me for a loop. But right now, one thing I know is what you are: a woman." She smiled back; he had said the right thing. "Well I can give you my number..." "I would like that." He interrupted. "And I don't mean to be insistent, but I'm not sure I can wait for the answers. I mean, as I pulled up behind your car I thought about the blowjob and how your legs looked the first time I saw you and I got hard again." She looked down and sure enough, there was a bulge in his pants. "Does that make me gay?" She looked him in the eyes. It was late, but tomorrow was Sunday. Moreover, even though it was an accident that he had found out about her secret, she had let it get that far without telling him. She felt like she owed him some explanations. "Okay. Where do you want to go?" "Do you mind my place? I've got some wine, if we need it." She pondered it for a moment. Her logical side told her that it was too soon, and Dave was still a stranger. It could be a trap. But her gut told her to go for it. "Mind if I follow you?" He smiled. "Of course not." ~ 4 ~ Dave lived in a nice apartment complex in an upscale neighborhood. The buildings were all brick and it was a gated community. The cars were all luxury class and none, aside from genuine classics, appeared to be more than five years old. She felt out of place even though her Focus was only a year old. She parked next to him and he was at her door, opening it for her. He took her hand and led her to his door. His apartment was nice, if Spartan. There was a couch, an entertainment center, some bookshelves and what appeared to be a well-stocked liquor buffet. But not much else. "Do you mind if I use the ladies room?" She asked as she slipped out of her boots. "Of course not, it's the first door down the hall on the right." He answered. "I want to check my messages real quick." He said dialing voicemail on his cell phone. She locked herself in the bathroom and sat, as ladies do, to pee. She pulled out her cell and texted her friend, Shelley, what was going on and where she was. That way if her gut were wrong, someone would know where to start looking for her. She also did something unusual. Nothing made her feel like a woman more than thigh highs. When she first started living as a full-time woman, she carried a spare pair everywhere she went. That way if she needed an extra boost of self-confidence she would put them on. Today she had worn yoga pants. She slipped them off and put on her stockings. She finished, 'borrowed' some mouthwash to get rid of the cum taste still in her mouth, and joined him in the living room. He was sitting on the couch and when she entered and stood up as he had been trained to do when a lady entered the room. "I didn't know what to pour you, so I don't have us drinks yet." He said as he started towards the buffet. "Please, sit down. I'll get it." She said with a smile and stepped over towards the buffet. Dave smiled too and sat back down. She looked the selection over. It was well stocked. There were several varieties of red and white wine some rum, expensive bottles of various whiskies. But what really caught her attention was a greenish-blue bottle. She picked up the bottle of Blue Label. "Exquisite taste." "Do you like Scotch?" He asked, not used to women liking whisky; much less something that was such an acquired taste like Scotch. Tiffany giggled. "Yes. But I've never had Blue Label. Too rich for a teacher's salary." "Well then, why don't you pour us a couple fingers each? I like mine over ice." She smiled as she poured the drinks. She crossed the room to the couch and handed a glass to Dave. She took a seat next to him, curling her legs underneath her. "I see you changed leggings, why?" Tiffany blushed. Her biggest secret was out. Why hold back now? "Well whenever I'm feeling stressed, thigh highs always makes me feel a little more confident and sexy." Dave smiled. He liked that in a woman. In fact, he had a box of thigh highs he had bought for his ex-wife that she never wore. She hated pantyhose and delighted in returning them to him. "That's wonderful. I love a woman in hose, and you've got some pretty spectacular legs." Tiffany blushed. "Would you like to touch them?" She waited the second for him to respond with held breath. When he nodded 'yes' she slowly uncurled her legs and stretched them over his lap. Slowly his hands touched her legs and started caressing them and her feet. "I've got to ask..." he started. "When did you decide to become a woman?" She took a deep breath and a long drink of her Scotch, impressed with just how smooth the Blue Label was. "Well there was always something off with me. I loved Star Wars, but that was about the only boy thing I liked. I would play Barbie with my girl cousins. Sometimes I'd be the damsel in distress when other kids played something like 'cops and robbers' and no girls were around. Then when I was a teen I found the joy of wearing Mom's pantyhose." She paused to look at him, searching his face for judgment or hate. There was none, just puzzlement and curiosity. "But I was always conflicted. I wanted to experience being a girl. But I didn't think of myself as gay. I was into women, exclusively into women. Then I was married. When she found out about my dressing she made me feel horrible about it, questioned my sexuality. Eventually so did I. When we got divorced, I started experimenting with it even more. Found some ladies, both genetic and T-gurl who helped me start to transform." "Wow." He said, taking in her story. "So the man you said you left St Louis because, was...?" "Me." She said solemnly. Then she looked at him, appraising his expression. "So now it's my turn to ask a question. Are you pissed at me?" The bluntness took him aback, not being used to a lady being so forthright. But then again, this was not your typical woman. "I am and I am not." With a deep, thoughtful sigh, he put his glass down. "I mean I did pursue you, hell I thought there was this spark between us at the parent-teacher conference..." "There was." She interrupted. He smiled a boyish smile that she had been falling for all day and night. "...so I noticed your Kallisti's Coffee cup and thought I'd help fate along a bit." She giggled. "Then fate wanted us to meet. I just stopped in there that night because it was close to school, their chai lattes are not too horrible, and they were serving chili that day. But their coffee sucks, and the men are too young...usually." He laughed and it was a good sign. "Why were you there today? And if I may ask, have you been with many men?" "Shelley, my T-gurl mentor so to speak, loves the place. We were supposed to meet, but this guy she's been crushing on who comes into her restaurant on a regular basis finally took her home. So she texted me after I ordered. So I was going to finish my coffee and leave when you showed up. As for men...you are the first man I've ever even kissed, much less blown." Dave's touch on her legs was intoxicating, it felt so good and when he massaged her feet, it felt so good after being trapped in her boots all day. This guy was really putting her at ease. Dave actually looked relieved. "So you're just as new to this as me?" She smiled and nodded. "And you're a virgin...down there?" Again, she nodded 'yes'. He thought for a second. "No, I'm not mad. I wanted to meet you, I made it happen. It's a first for both us, so I guess I can understand why you didn't just blurt out 'I was born a man' in the middle of a public place." Dave paused a second, he was having trouble thinking of this woman as ever having been a man. "Why did you go along with it?" She blushed and looked away from him. "I wanted it to happen just as much as you. I was just so terrified at the thought of it happening. Then I was terrified on and off all the time it was happening. But I was loving being with you. Your touch, your kiss." He reached out and gently took her hand. "When you asked me over, my heart said 'yes' before my brain could remember I still have one last man-bit." When she looked back at him, his hands moved up her leg and arm to grab her and pull her into a kiss. She was happily surprised. Dave was just as surprised as she was that he was kissing her. He was angry that she did not tell him when he asked her to go for drinks. Or before they kissed. Or before she blew him. Well, maybe he was not angry about the last one. After all, it was the best blowjob of his life. Nevertheless, he did not know who she was before she was a she. Perhaps it was the alcohol or the late hour, but he could not think of her as anything but a woman. And there was a spark. The kiss was passionate; she parted her lips inviting his tongue to dance with her's. She closed her eyes and wrapped her arm around his neck and shoulders while softly caressing his cheek with her free hand. This opened her body to him, his hands exploring her curves. Not satisfied with groping her through her dress and bra, he found the hem of her dress and pulled it off over her head. He took a moment to admire her body as she blushed and averted her gaze, she was exited and terrified at the same time since he was the first man to ever see her this undressed in a romantic setting. She was wearing a matching black bra and panty set with her thigh highs. He was pleasantly surprised. She had a flat tummy, but not one with manly six pack abs. Since he had found out that she was born a man, he had wondered about her breasts. The two times he had seen her, she had been wearing dresses that concealed her cleavage. So he wondered if they were some sort of fake breast forms. Instead, they were real. Dave had learned a few things about transsexuals, his firm had hired an intern who was going through 'transformation' and she talked about the process. Some of his co-workers shunned her and called her 'it', but it was her life and what she did with it did not bother him. So he tried to be nice to her, but you could tell that she had been born a he. But not Tiffany, had it not been for the bulge in her black panties (that he was trying damn hard to ignore for the moment) he would have sworn she was a natural born woman. She had a wonderful hourglass figure and smooth, soft skin. Her bra had a front hasp that was only too eager to be unfastened and he removed it revealing two perky breasts with quarter size areolas. Now topless, she changed position. Once more she tucked her legs underneath her and placed both hands on her ankles in a pose that jutted her breasts out in invitation to his caress. She moaned as he touched her. They felt wonderful, he could not tell any difference between them and a natural born woman's breast. Tentatively, he leaned forward and kissed an erect nipple. Again, it was like kissing a woman's breast. He began to suckle lustfully. With each new discovery of her body being more woman than man, the less he cared about her bulge. Soon he was nibbling and sucking on her neck, not caring that he was leaving a nice sized hickey on her neck. "I need you, I want you." He whispered hungrily in her ear. "Yes." Was all she said, all she needed to say. He lifted her off the couch and carried her into his bedroom. Gently laying her on the bed, he started taking his own clothes off, admiring the beautiful woman in his bed. He kissed her deeply and then gently guided her to all fours and pulled her panties off and tossed them to the side of the bed. He had always wanted to do this with his ex-wife, but she thought anal sex was gross. He was not prepared, he did not have a condom or lube so he spit on his hand and rubbed it on his thick, erect cock and on her tight brown eye. Slowly, he eased into her. She was tight, tighter than he had expected. She grunted and groaned in pain as his thick cock entered her. He hesitated, not wanting to hurt this wonderful woman. Feeling his hesitation, she pushed back taking some more of him into her slowly. "Oh, Dave..." she moaned. She smiled as he responded by grabbing her by the hips and pulling her towards him as he pushed in. It hurt and she grunted as her sphincter struggled in vain to push the invader out. She screamed into his pillow as he took her, stretching her well past the largest training anal plug she had so far tried. He stopped again and she looked over her shoulder at him, smiling through the pain. "It's okay Dave; Shelley said it would hurt the first time." Her eyes were tearing up as she spoke, seeing that this caused him concern she wiggled her ass and pushed back a little bit. "I want you." She said, and then gasped as Dave could no long restrain his passion and plunged into her. He began pounding her ass, his ball sack slapping against her's. Slowly, it started feeling good as her sphincter relaxed and his head rubbed against her prostate. Her moaning softened from one of pain to one of pleasure. Recognizing that he was no longer hurting her, he began pulling out only to thrust back in harder than before. He was moaning as her ass was now comfortable tight on his cock. "Fuck, Tiffany!" Was the only warning she got as he swelled inside her and let loose a hot stream of cum deep inside her. The sensation was too much, she came, spraying her honey all over his bed. Satisfied, he pulled out quickly. She squealed suddenly feeling herself empty but full of cum. Holding her hand close to her ass, she quickly a lighted to the bathroom and shut the door. It caught Dave as funny and kind of cute. He began laughing. While the sound was music to her ears, that it was directed at her predicament made her blush with embarrassment. "Don't laugh at me!" She yelled through the closed bathroom door. "I'm sorry," he said from the other side, "can I get you something to sleep in?" He could not see her face, but she was beaming, happy that he wanted her to stay. "Yes please...and my panties." He brought her one of his old dress shirts. He had lost some weight since the divorce, as well as toning up. So when she came back to bed after cleaning herself up, it hung loosely on her so she looked like any woman coming to her man's bed wearing her shirt. "Thigh highs?" She asked. "Leave them on or take them off?" He had always wanted his ex-wife to sleep in nothing but thigh highs and loose shirt. Now it was his turn to beam, this was the woman of his dreams. "Leave them on." She said nothing but smiled as she slid into bed next to him. He took her into his arms and held her close, smelling her hair and perfume. He kissed her good night. "You're beautiful." He said. These words echoing in her ears, she smiled as she fell asleep in her new lover's arms for the first time. His Son's Teacher Ch. 03 ~ 5 ~ Slowly Tiffany awoke from a very wonderful dream. The man she had been crushing on had asked her out and in a terror and magic filled evening, she had experienced her first sexual encounters with a man. Although not quite awake, she smiled and whispered his name: "Dave." What she did not expect was the bed to move in response! Slowly as she awoke to different smells than what she was used to in her apartment, she realized that she really was in a man's bed! A dull ache in her ass also reminded her that her V-card really had been punched! And then there was the taste in her mouth... There was also the warmth of another human being and an arm wrapped around her. She beamed in delight! It was true! She felt his morning wood stiffening against her heart shaped ass. She was still wearing his dress shirt, although in their sleep his hand had found its way inside and was now resting possessively on her tit. Even in his sleep, he was claiming her! She rubbed her foot, still clad in nylons, along his athletic legs. She felt his cock stiffen against her and she had to bite her lip to keep from either squealing in delight or giggling in joy. "Mmmmmm...." He moaned and rolled over onto his back. Wide-awake, Tiffany knew this was her chance to make a good first morning impression. She gently turned to him and started kissing down his chest. It was muscular and hairless, and she was thankful that he slept in the nude. She found his cock and slid it into her mouth, slowly sliding the thick shaft in and out of her mouth. Last night she had admired and worshiped the member, but now she wanted him to wake up to it in her mouth as she orally made love to him. She did her best to ignore the smell and strange taste, it was not as bad as she expected. Maybe he had cleaned himself up after she fell asleep? Within seconds, she was rewarded with his hand on her head, his fingers intertwining with her hair and gently pulling it as he started using her head to jack off into in his sleep. She smiled, yes, she knew she was being used, but she did not care. This was her way of thanking him for being a gentleman and making a dream come true, and allowing her to wake up in his arms with her dignity intact. Although, as he moaned she caught herself wondering who he was dreaming of as she sucked his cock. She could tell he still mourned for his failed marriage, but there was a spark between them. In her heart she hoped he was dreaming of her. But how would she ever know? Slowly, she slid her tongue along the base of his shaft as he stopped pressing her head down. Right before his glans would pop out of her mouth, he pushed her back down until the tip of her nose was tickled by his pubic hair. "Oh, Tiffany..." he moaned. The words lifted her spirits, but also gave her a split second warning. She felt his shaft swell and his glans erupt inside her mouth. Once more, she tasted his cum, this time it was a little bitter. She wondered if the first time she tasted it was so good because it actually tasted good...or if it was the emotion of the moment. Then she wondered if it could have been all the whiskey he had drank the following evening. But, it tasted good because it was her name on his lips as he came. She had worried that he would cry out another woman's name. But he had said her's instead! She was smiling as she slowly kissed her way back up his chest and then her head slowly slipped out from beneath the covers. "Good morning, handsome." He smiled down at her. "Good morning, beautiful." He said, sleepily. "Did you sleep well?" He asked as he gently pulled her out from under the covers and held her close. She beamed; he seemed to actually care for her comfort. "Dave...may I take a shower before I go?" She was feeling him out; she really didn't want to leave. He frowned a little. "Do you have plans today?" He looked at the clock by his bed. "It's only about 8:45. We could cook breakfast." The disappointed look on his face made her happy; he did not want her to go either. "No...I don't have anything until tonight...and that's just getting ready for work tomorrow. I could hang around a little bit." She noticed the weariness in his eyes. "Would you like to sleep a little more? I'm awake...I could shower and start cooking." "That sounds wonderful, Tiff." He replied. "There's a linen closet next to the bathroom, there should be a pack of toothbrushes in there. Help yourself." She got out of bed and he took a moment to admire her. She looked so damn hot in his shirt. One thigh high's elastic had failed and now drooped on one leg. The other had a run in it. "Listen, if you want you can use my washer and dryer." He said, realizing that he did not want her to change back into her attractive, but all covering dress. "You could borrow another shirt. Also, my ex-wife didn't like that I was always buying her thigh highs. So when I moved out she gave them back to me...still in the packaging. Help yourself; they're in the closet behind my dirty clothes hamper." Tiffany giggled. "I don't guess she left any panties with you, would she?" She wanted to wash her panties, but did not want her 'clitty' flopping around all day ruining the illusion. He laughed. "I have some boxers and bikini briefs in my top dresser drawer." He watched her as she gathered the clothes. She first picked a black pair of bikini briefs from his drawer. He thought it was a good pick; boxers would have covered up more of her wonderful thighs. She then leaned over and her heart shaped butt was shown off as she dub-out the nylons. "Wow!" She said. "You've got great taste!" She was impressed by his selection, expensive silk stockings from around the world. She found one with elastic lace bands; she recognized them from the internet. "I always wondered how these would feel." He smiled, sleepily, from the bed. "They're yours. Also, I'd put on some weight after the divorce. The shirts on the right in the back are a little larger, if you want a more loose fit." He thought she was hot and by no means needed to lose weight. But she was tall for a woman and the loser fit would give her a more feminine appearance. She selected a light blue shirt with white cuffs and collar. Gathering her change of clothing she headed off to the bathroom. Dave smiled, self-satisfied, at the way she walked awkwardly. As she softly closed the bedroom door behind her, he closed his eyes and drifted back to sleep. * * * The warm water felt good on her used body. She had a dull ache in her ass, but her heart was flying. Twenty-four hours ago, she was getting ready to hit the coffee shop for another Saturday night alone. Then she was surprised when the man of her dreams showed up at the coffee house, in pursuit of her! As the night's events replayed in her head, she found that her hand had drifted down to her clitty and was stroking it. She was surprised how everything was different now as she masturbated. She could taste his cum and smell his cologne. As she thought about his cock buried inside her she could feel it. It was sensually different now. It was as if it was happening to her all over again. Her hand, lathered in soap, felt so good as she stroked her shaft. She was cumming before she knew it. "Mmm...Dave..." she softly moaned as she sprayed her honey over his shower wall. She watched in fascination as the water carried her love juices down the drain. * * * After a long, cleansing shower she toweled off and dressed in his clothes. The designer thigh highs felt as good as she imagined they would as she slowly rolled them up one shapely leg and then the other. His bikini briefs were a little big on her, but she looked at herself in the mirror. They were passable, and reminded her of the days when she would buy underwear like that to cross-dress in. They were more comfortable than women's panties. She might find an excuse to keep them. She giggled, realizing that now that her V-card was punched, she was considering going back to wearing under things that were comfortable instead of sexy. She slipped into his shirt. She only buttoned the middle two buttons and looked at herself in the full-length mirror. She was pleased with how loosely it hung on her, and she was glad he had suggested putting on one larger; it looked more feminine hanging off her. She stepped out of the bathroom to retrieve her purse. She kept a spare make-up kit on her during the weekends. More than one time Shelley had called her to go out, and there was not enough time to go home and get made-up. As she quietly made her way through Dave's apartment, she could hear him quietly snoring in the bed. Once she was done with putting on her face, she took one more look at herself in the mirror. Her long, straight brunette hair was down, brushed and freely laying across her shoulders. She put her glasses on, with better than 20/20 vision she did not need them, but she thought the black rimmed glasses gave her a more feminine appearance. Besides, she had always thought the sexy librarian look was...sexy. Pleased with her appearance, she went into his kitchen. She marveled at the place. Dark wood cabinets, stainless steel appliances and expensive cookware...all more than she could afford on a first year teacher's salary. She found his coffee and it smelled wonderful, so much better than the stuff they sold at Kallisti's. She scooped several scoops into the coffee maker; she was delighted that he had a more traditional coffee maker than the modern, pre-measured cups of some of the newer and more gourmet coffee makers. Happily, she began cooking breakfast. * * * Dave awoke to the smell of coffee being brewed. He smiled, glad that Tiffany had decided to stay and was now cooking them breakfast. He got up, went to the bathroom, and started taking a shower. The steam helped clear his head. He really liked this girl, and that really surprised him. He was a straight guy, and was never even curious about 'she male' porn or the intern at work. She was passable enough, but knowing that she was a he from the start...kept him from finding her attractive. So why now? So many thoughts ran through his head. They clicked. She gave amazing head, and he had finally experienced anal sex...and he liked it. He liked it a lot. She was incredibly tight, and it somewhat hurt. However, he figured it would get looser as they continued having sex. Was 'sex' what he thought they had done? Was it as meaningless as a random hook-up? Or was it something deeper, had they made love? He moaned, which stirred him back to reality, a reality where he was stroking himself as he thought of all they had done. He smiled as he jerked off, thinking of the girl he had last night. His mind wandered to pleasuring her, something he loved doing to and with his ex-wife. Kissing her lips, nibbling on her earlobes and neck before slowly making his way down her chest...kissing and exploring her body. His hand stroked faster and faster. He could smell Tiffany's perfume and taste of her skin, it was a pleasant change from still dreaming of his ex-wife. In fact, Tiffany was the first woman he had masturbated to since his ex...something he had been doing since he met her a few weeks ago. In his daydream, he was kissing and tonguing her belly button before making a final dash for her pussy. Then it hit him; she did not have a pussy. Instead of the pink lips that he so loved, there was a hard cock. This mental image shocked him back to the reality of the situation. He was in his shower and about to cum thinking about a 'chick with a dick'. He had always prided himself in being a slow lover who loved pleasuring his woman. But he did not want to suck a cock; did she want or expect that? What about her desires...did she want to fuck him? These thoughts grossed him out; he was a straight man and in his way of thinking, sucking cock and taking it in the ass were not things straight men did. He thought about this as he turned the water off and toweled himself dry. What should he do? He had mixed feelings and had nothing in his moral compass to point him in the right direction. He slid on a comfortable pair of designer lounge pants, no underwear...it was a Sunday after all. His world, he thought as he dressed himself on autopilot, was typically ordered and linear. However, ever since the divorce, nothing seemed to flow logically in his life. He felt as if having a failed marriage meant he was a failure as a man. Now he had had sex with a girl who was not all girl...but he could not think of as anything but a woman. Would he get past his aversion to touching another cock enough to be fair to her? The logical side of him thought that perhaps it would be best to stop the relationship from progressing. Promise her they will be friends and then not have anything to do with her after she left his apartment. Not because dating her would be completely illogical, but rather was he emotionally ready for it? It would hurt both of them when she walked out the door, but would it be less painful in the long run? Would it be fairer? Should he talk to her and express his concern? He put on his t-shirt, deciding that he would be blunt with her. Talk about his fears and maybe let her down easy. 'Yeah, letting her down easy won't be so hard' he thought as he opened the bathroom door and was greeted with the smell of breakfast. 'It did smell good...Laura was not much of a cook, what if Tiffany is?' His heart finally having the courage to think. 'Is that a whiff of her perfume? Remember Gillian, your first love way back in high school? Didn't she wear that perfume?' His heart continued its assault on his logic. He shook his head, willing his feelings aside as he walked into his kitchen. After all, logic had never steered him wrong by ever...looking so incredibly sexy wearing his shirt while cooking him breakfast. Logic never loved wearing black thigh highs as much as he loved seeing her wear them. Logic never delicately brushed an errant strand of hair from her face in a graceful, feminine motion that made him want more. And logic never turned and smiled at his entrance, happy to see him and say; "Good morning, Dave. Sleep well?" It was her voice that was the final straw that broke his logic's back. "Good morning, Tiffany." He said as he confidently crossed the distance between them. "Damn logic, full speed ahead." He whispered as he swept her into his arms and kissed her, firmly and passionately on the lips. * * * Tiffany heard him coming, her own thoughts of logic, terror, and desire battling it out for supremacy in her heart and mind. She wasn't sure what to do, so she stood there for a moment allowing him to look at her. She blushed in her partially dressed state, and part of her wished her clothes were not in the washer but instead on her so she could flee his apartment and this awkwardness. But at the same time, her heart reminded her that he had not kicked her out and had even given her expensive thigh highs. So perhaps she should keep it simple. She turned to him and smiled, her smile brightening when she saw him. "Good morning, Dave. Sleep well?" She said. "Good morning, Tiffany." She heard him say along with an incoherent mumble seconds before being swept into his arms. His lips were on hers, and she had surrendered to them before she could even think about what was happening. She wrapped her arms around him as he leaned into the kiss, bending her backwards like that sweet World War II picture of the sailor and the nurse. One barefoot clad in stockings, gently caressed his leg as they kissed. Their tongues danced her mouth for an eternity that was way too short. She was blushing when he returned her to her original upright position. Now her path was clear. She would spend the day with him. It may not be forever, but being with him felt right...at least for the moment. "How long until breakfast is ready?" He asked. "I don't know, twenty minutes?" "Cool." He replied thoughtfully. "I need to run to the corner store real quick...do you mind? I want some OJ to go with it, I'll be right back." She smiled as she kissed him good-bye. It was a good sign that he felt comfortable leaving her there alone. But then again, she was not just a stranger he met at some bar, he knew where she worked. ~ 6 ~ Dave returned about thirty minutes later and put the OJ in the fridge and put something else away as she served breakfast. They sat down and began to eat. As passionate as the good morning kiss was in the kitchen, the breakfast table conversation was nonexistent. They just stared at each other with a mix of admiration and trepidation. Neither not sure how to proceed, neither wanting to mess things up. Finally, she took a deep breath. "Dave...would you like to talk about 'it' some more?" 'YES!' He almost said very loudly and very eagerly. He coughed, gathering his thoughts. "Sure..." he said, still thinking where to begin, and then thinking perhaps starting with her name would be a good beginning. "Why Tiffany? Why that name, if it isn't too personal?" She had to suppress a giggle. A few hours ago, his dick was in her ass, and she wondered if anything would ever be too personal to talk to this man about. "That's an easy one. Had I been born with my physical gender matching my real gender, I would've been named Tiffany." "Have you had any surgery done?" He said, he had been wondering about it all night. Had she always been so feminine or did she have work done? Also her breasts felt so natural, not like the strippers that had occupied his idle time since the divorce. "I've had a nose job and a face-lift. Nothing too major, just enough to make me look more natural." She explained. "I've been on hormones, that's where my breasts came from. My doctor was surprised that I was able to reach stage five on the Tanner scale. Most transwomen who start in their twenties like I did are lucky to reach stage four. I was expecting to get implants, but that's $10,000 I can save for the last operation." On one hand she felt a little uncomfortable talking about it, she was afraid it would break the illusion of her as a woman. But on the other hand, if this had any hope of continuing he would have to know what the process was. "Well, I think you're very beautiful." He reached below the table where her foot was and gently grasping it, pulled it up to his crotch and began to rub it. She smiled and cooed as his strong hands massaged the stress out of her. "Last operation?" He asked expectantly. If it was what he thought it was, that would solve many problems. She blushed. "Yes, I'm saving to go all the way." Tiffany felt more than a little nervous. She was opening up to a guy she barely knew about the most intimate details of her life. But then again, outside of her therapist, doctor, and Shelley, he was the only one in Portland who knew her secret. Dave smiled, and she could tell that it was a relief for him. She felt mixed about it; on one hand, she wanted to be accepted for who she was. On the other hand, she herself tried to pretend that she had a different set of equipment between her legs. She knew he was a straight male and was attracted to the parts of her that were all woman, and that he had not kicked her out but instead was talking to her about in an effort to get to know and possibly date her. "I can see you would prefer I'd been born the 'other' way?" Dave realized that his reaction to her answer had given away too much of what he was thinking. While he did not want to hurt her feelings, he did want to be honest with her from the beginning. Besides, he loved the feel of a woman's feet in stockings, and Tiffany seemed to share that fetish. As he massaged the soles of her right foot, she slowly rubbed his crotch with her left foot. "Honestly Tiffany...yes I wish you had been born a girl." He examined her expression; it was neither happy nor hurt so he continued. "It's because I've truly enjoyed the last 24 hours. Even if your secret has spun my head around. I'm not sure where to go from here. I mean, if you had a pussy...I'd know what to do." His Son's Teacher Ch. 03 "Why don't you know what to do now?" She asked, not as an accusation but more to understand him and what he was feeling. Her voice was soft. "Well, it's...it's..." Dave stumbled over saying the things he was thinking and feeling. "It's just that...it'd be the mystery of you...not of me." Tiffany giggled. "So a t-girl is not a big enough mystery for you?" Her laugh and the simple truth hidden in the humor of her questioned lightened the mood. He laughed, which was music to her ears. "No...I mean...yes...you are VERY mysterious. But I mean...I wouldn't have to figure out my own mystery. I've never been attracted to men before...or even shemales. So now, when you walk out that door...I need to figure out if the divorce changed me in some very profound ways. I mean you said that you were married once. What if I decide suddenly I want to be a girl? Also, since I couldn't tell...does that make me gay?" She smiled and slid her feet out from his lap. She saw a momentary terror on his face, thinking he had just messed things up. She stood up and walked around the table towards him. She was stunning; barefoot in exquisite stockings and his shirt. The fullness of her wonderfully feminine breasts just hinted at through his baggy shirt, and that she had only fastened two buttons on the lower half of her shirt gave him a peak at her wonderful cleavage. He half expected her to slap him as she drew in close to him... ...and slid into his lap, wrapping her arms around his neck and giving him a soft kiss. "Thank you Dave, for being honest with me about how you are feeling." She kissed him again. He wrapped one arm about her waist and explored her leg with his free hand. "I do not think you are gay. You did not ask me out knowing that I was born a he. You saw a woman you thought was attractive..." "Beautiful." He corrected her; she paused and bathed in the compliment for a moment. "Okay...beautiful...thank you very much." He was rewarded with another sweet kiss. His hand played with the lace tops of her thigh highs, enjoying the different textures of nylon, lace, and alabaster flesh. "But you asked out a woman...not a man. Also, have you ever worn women's clothes...other than a joke...and just because you felt 'at home' or 'natural' in them?" "No." "Have you ever been accused of being effeminate? Girly? A sissy?" He shook his head 'no'. Tiffany giggled. "Well then darling...you have nothing to worry about. You are not going to wake up some morning and think: 'gee...I'm really tired of having a penis...I think I want a pussy'." She looked at him, her words soaking in. She had meant for them to be comforting, but they looked like they stung him a little. "Listen, I didn't mean to be a bitch. It's just that this journey to my womanhood was not sudden and it was not in reaction to getting my heart broke by a woman. I always felt a little 'off' or 'different' from other boys. Then as a teen, I felt nylon against MY skin for the first time and felt...right. Tiffany was always right here," she took his hand and placed it on her left breast just above her heart, "she has always been me." He looked her in eyes. Her beautiful, kind, soft, blue eyes. He saw into her soul, the soul of a woman. He could feel her heart beating, her wonderfully soft and warm breast in his hands. "I've never felt anything like that." He admitted. She kissed him again, something he thought he would never get enough of. "See...nothing to worry about." She said, and he could sense the truth in her words. The dryer buzzer buzzed, her clothes were ready. "I need to get those before they get all wrinkled." She stood up and he understood the relatively new cliché 'I hate to see you go, but love to watch you leave'. She paused just before disappearing into the laundry room. "Dave?" "Yes, Tiffany?" "I...I can go...if you need time to think." He took a sip of coffee and smiled. "You said you liked Star Wars...think you'd like to watch Jedi with me? We could watch it in the living room or the bedroom." "I would love that." * * * Tiffany had opted for the bedroom. She was comfortable in her modest state of dress, and the bedroom fit the mood. Now that it was past noon, she would have been uncomfortable being so casual but all she had was street clothes. She knew that once she had dressed, she would be pulled to go home and prepare for the next day at school. Moreover, she did not want to leave Dave, not just yet. So they lay snuggled up watching the third movie of the original trilogy in his bed. Her legs intertwined with his, he softly groped her and she would randomly kiss him. After their talk, she had helped him avoid blue balls by taking the time to give him another blowjob. She understood the male sex drive as well as how it felt when that urge went unsatisfied; so she did not mind doing him the favor. He noted that she was getting better at giving head. She noted that she was starting to actually really like his taste. Now they were watching as the hero entered the villain's lair to save his friends and sister. When the Princess appeared wearing a set of revealing slave silks, she felt his cock stir to life. She looked up at him and smiled, he was flushed obviously embarrassed. "Sorry," he said, "it's...it's just that this is the first time I ever felt...well...you know..." "It's okay honey, I understand. You always wanted to do her...and I always wanted to be her." It was her turn to blush. "Once when I was in high school, my parents left me alone and I spent about three hours wearing one of my mom's pink slips, pantyhose, panties, and bra. I'd also bought a dog collar and chain and bound myself to my bed." "Really? You...you like that 50 Shades stuff too?" "Yes." She blushed and looked away. She felt his strong finger on her chin and her head tilted up so he could kiss her. He pulled her to his embrace, as the movie became background noise. He kissed her, passionately and possessively. She looked up at him; he had rolled her onto her back and was prying her legs apart as he slid between them. His hands were in her hair as his mouth explored her lips, earlobes, and neck. He was pulling on her hair, moving her head this way and that as he found a new place to taste. He stopped kissing her long enough to slide a pillow under her ass, and slid the borrowed pair of bikini briefs off her. He was pleasantly surprised that the sight of her cock did not bother him as much. "Dave what are..." he silenced her by gently placing a finger on her lips. He leaned over and retrieved something out of his nightstand; a bag from the store he went to this morning. From the bag, he withdrew a box of lube. It said the brand name and 'His & Hers' in big letters above a picture of two tubes; one blue and one pink. He opened it and squeezed some from the blue tube onto his hand before rubbing it along his throbbing cock. She groaned as he began rubbing some of the pink tube's lube along her ring, which he had learned she liked to call her 'pussy'. He watched as she squirmed beneath him as he prepared her pussy. For her part, Tiffany did her best to relax and let him have his way with her. She unbuttoned the shirt and slid out of it. He finished lubing her, and then started to rub his cockhead against her, slowly pushing in. She was still very tight, but not as tight as last night. They were not numbed by being drunk either, so he took his time as he slid into her. He paused as his cockhead slipped in and was greedily held tight by her ring. He looked into her eyes. She moaned, it hurt but felt so good. She was also amazed that he was able to take her missionary. While considered rather vanilla and uncreative in traditionally straight couples, she had not thought it would be possible until she had her surgery. She felt him stop, so she opened her eyes and looked up at him. She smiled, not daring to say anything. He had told her to be silent, so she waited for permission to speak. "Are you okay, Tiffany?" He asked, his voice gentle. She nodded 'yes'. "Does it hurt...bad?" He asked again, this time she shook her head 'no'. He leaned over and whispered in her ear: "I want to fuck you. I want to make you mine. I do not want to hold back, I just want to take you. Do you want that?" She nodded 'yes', this time a little more vigorously. "I want to hear you say it." "Fuck me Dave; make me yours...do not hold back." Her voice was soft and breathless. It hurt taking him inside her, but it also felt wonderful. She loved being held by him. She loved the scent of him. Then she felt him enter her...filling her with him, and sliding all his length into her with one powerful thrust. Then he was all over her, pulling out of her until her ring caught on the lip of his glans, before slamming back into her. His mouth was on her neck kissing and sucking. His hands were squeezing her tits as he fucked her. Fucked her as if she had been born a woman. She wrapped her legs around his waist as he slid in and out of her. Her fingernails dug into his back as she held on as his powerful body took her. She was moaning with pleasure, and even crying a little from the pain. This was the best moment of her adult life; this wonderful man was making her a woman. Then something incredible happened, he hit a spot deep inside her and she immediately came. Her body spasmed around his cock as she came, spurting her honey all across their bodies. It seemed like the orgasm lasted forever, more intensely than she had ever cum before. She was just coming down from the high when he hit it again, causing her to cum again, this time he had moved curious about the new wet sensation on his chest, so she ended up cumming on her own tits. All Dave saw were those beautiful breasts with cum on them. This was almost too much for him. He had not seen her cock spray the cum, just this beautiful woman suddenly covered in sperm. She looked up at him; she was obviously lost in ecstasy. He enjoyed the view when his tip hit her g-spot once more and she came, once more spraying her breasts with the fluid. A glob even splattered across her lips. She parted her lips and with her tongue, lapped the glob into her mouth. The scene was just too much for him and he came, deep inside her. His warm seed filled her, as she was finally cumming down off the intense orgasm. She made a mental note to ask Shelley just what in the hell that was...and if it was common. She felt him as he stopped thrusting and drew her into an embrace, holding her tight. Her own cock had deflated, and she could feel his doing the same inside her. Therefore, she just held on to him as long as she could, but then he was about to pop out of her and she knew she would have to rush out of bed and into the bathroom rather quickly. She kissed him, passionately as he held her. * * * It was around eight at night when Tiffany got back to her apartment. Dave had waited a few minutes to knock on the bathroom door. He had toweled off, his chest had been smeared by her honey too when she came. She had feared that this would be too much for him to deal with and he would want her to leave. After all, she remembered her early days when she would feel guilt the second she came while dressed. Would it be the same for him...or had he fully bought into her identity as a woman despite still being 'pre-op'? What he wanted was to shower with her. It was a sweet affair; he washed her first, using his hands to lather her body as the warm water soothed her body. He even intentionally touched her cock for the first time, but well spent it did not rise to the occasion. When he had rinsed the shampoo from her hair, they shared a kiss under the warm shower. Then it was her turn to wash him, a chore she relished. She loved watching the water as it ran down his chest. The feel of his muscles as she explored his body with her soapy hands. She was amazed at his virility as his cock became hard as she washed it. She was on her knees, her fingers teasing the cock back to life while she watched in fascination. She started to lean in to kiss and suck it, but he pulled her to her feet and asked her for a handjob. Without waiting for an answer, he kissed her and she obediently began to stroke his cock. His hands ranged over her body, relishing her tight ass. Squeezing her breasts. Her hands, slick with soap, stroking his cock. She felt his heart beat as the vein along the top of his shaft pulsed with life. The large mushroom shape of his glans. She teased his balls with her fingernails, and was soft and gentle with the underside of his shaft. Soon the whole dick was throbbing in her hands as he came for the last time that day. It sprayed her thighs, cock, tummy, and hand. She made a show of licking and swallowing it off her hand as he washed it off her body. After the shower, he gave her another shirt, bikini briefs, and pair of thigh highs. She was delighted that they shared the fetish. They settled into bed and finished watching the movie. They kissed and lightly groped until dinnertime when they opted to order Chinese in. She answered the door and he relished how the driver looked at her in her immodest state of undress with lust. They ate snuggled up on the couch watching an evening news 'magazine' that had been a staple of Sunday evenings since they were both children. When it was over, she rinsed what few dishes they used and loaded his dishwasher for him. Sadly, it was also time for her to go home. She closed the door behind and just leaned against it, happy to be home and happy to be confused over a romantic conundrum. He had taken a call from his son, and when he laid the phone down after the call and stepped into the bathroom, she entered her phone number. She really, really, really wanted him to call. However, even if he did not she had her memories, as well as his shirt which she had sneaked into her purse when he was not looking. She would sleep in it for the next couple of months. Moreover, it was a good trade; she had left her opaque thigh highs and panties under his pillow as a trophy for him. She smiled, wondering if he had found them yet. * * * After Tiffany went home, Dave collapsed into bed and tried to think, but found thought elusive and sleep insistent. He did not find his trophies, which had been neatly folded, perfumed, and tucked, under his pillow, until the next morning when he stripped the bed to wash the very used and dirty sheets. He smiled as he inhaled her scent. Since he had gone to bed much earlier than normal, he beat his alarm by about 45 minutes, which gave him ample time to enjoy another hot shower and decent breakfast. He drove to work listening to the radio station she had wanted to listen to Saturday night. Normally, he listened to the news or talk radio, but this morning he was in the mood for music. It was in traffic that he realized he had made a mistake not getting her phone number. His mind brainstormed ways to get it; would showing up at school be creepy? Should he make another romantic gesture? Perhaps he should start going back to Kallisti's Coffee? As traffic slowed to a stop, he decided to get his mind into work mode, so he took out his phone to scroll through his contacts to see if there was a client, he could call. He smiled when he saw her name in his contacts, and a picture. Not only had she left her number, but she had left a picture of her as well! He opened the picture up in full size mode and was pleased. She was holding the phone up so it was from the point of view of looking down at her. She was kneeling on his bed and besides her beautiful face; he could see a nice down the shirt of her breasts as well as her nylon-clad legs. He resisted the urge to call her just then; she would be busy at school. Nevertheless, his mood was once again buoyed. His co-workers commented on his demeanor and his best friend at his firm pulled him aside and asked him who had made him so happy. He blushed and showed him the picture. James, his co-worker, punched him the shoulder and complimented him on his conquest. He even told Dave that he should call her and see her again, that he had not seen Dave this happy since the divorce. He also warned Dave about calling too soon, that the perfect time to call was to wait three days. Dave thanked him for the advice, after all, he had been out of the dating scene for twenty years and James was a confirmed bachelor and the office womanizer. That night, all alone in his apartment and her perfume still lingering in the air, he tried to resist the temptation to call her. James knew what he was talking about when it came to women. But then again, Tiffany was not your average woman by a long shot. It was about eight when he gave in and pulled up her contact and pressed send. "Hello Tiffany, its Dave...would you like to do dinner Wednesday night?" His Son's Teacher Ch. 04 PART TWO: The Spring Break Getaway ~1~ Tiffany had Dave's cock buried in her mouth as he drove to Hayden Lake for a long weekend getaway. It was the Friday night before spring break and they were going for a long weekend at his cabin in Idaho. They were about an hour into the seven-hour drive to his lake cabin he had managed to keep in his divorce. She had gotten bored and had teased his cock from his pants as he drove. The gear selector of his Lexus was pushing uncomfortably into her stomach. It was an awkward position for her, and now she understood why girls did not like giving road head. However, she did not care. It had been a long day. The teachers and the kids were excited for the weeklong break away from school and whatever they had planned. For Ms. Stepford this meant sneaking away to the mountains around Hayden Lake for four days of bliss with the new man in her life. She had worn jeans to work for the first time all year and a comfortable t-shirt since Dave was picking her up from school and they were leaving early. He had been as disappointed as the teen boys had been in her class that he could not see her legs. When he complained she leaned over, kissed him and wiggled out of the tight fitting jeans and comfy tennis shoes. He smiled at the sight of her dark blue, pin-stripped panties and matching garter-belt clipped to back seamed black thigh highs. He complained about the loose-fitting t-shirt and that too came off revealing a halter-top thingy that many young women would wear on a summer's day. It matched her panties and pushed up her c-cup breasts in a delightful presentation for his benefit. She tried starting up a conversation with him, but she soon found she was the only one talking about her day. He was concentrating on the road as she'd noticed he was want to do, and he seemed tired from work and just not talkative. Therefore, once they were out of the metro traffic she turned the radio to the talk channel he liked so much and she hated. She placed a hand on his knee and slowly slid it up, enjoying the feel of his leg through the thin material of his suit pants. "What are you doing, Tiff?" He asked a surprised expression on his face. She put one finger to her lips as she unbuckled his belt, shushing him. She teased him by slowly making her way up his thigh before unbuckling his belt. She awkwardly struggled with his button, and then slowly unzipped his pants. He squirmed as her soft, warm hands guided his stiff cock out of his underwear. She could smell him; he had left straight from work so he smelled of the day's toil. She closed her eyes, trying not to think of what the different things she smelled were. And so here she was, the gear selector poking her uncomfortably in the belly. Nevertheless, she did not care; she was pleasuring the man she had started developing deep feelings for. Her lips were wrapped tightly around his shaft, her tongue dancing along it as she raised her head off and then slurping it back down. She was cleaning his cock of the day's work as he drove. She teased his balls with the tips of her fingernails; he had surprised her with a gift certificate to an exclusive salon to get a French manicure and pedicure. He groaned at the delightful caress. She felt his hand on her head, gently caressing her hair. "Fuck, Tiffany...you are awesome." He said, his voice more relaxed, his mind trying to think of suave things to say to her. She stroked his cock as she slid his cock in and out of her mouth, taking it a little deeper each time. She relaxed her throat; his head was hitting her gag reflex. She knew he was fascinated with the idea of being deep throated, so she was working on getting past the reflex. He smiled moaning, "Good girl, Tiffany..." as she made little gagging noises. The sound of his voice, so longing for her and the pleasure she could give him inspired her to take him deeper. As she gagged, her throat spasmed along his cock. They passed a semi; the trucker sped up to match their speed after seeing what was going on. He gave Dave a thumbs-up and blew his air horn. Tiffany, surprised by the air horn almost slid off his cock, until she felt it start to twitch. She wrapped her lips around it even tighter and keeping half of it in her mouth licked all the sensitive parts of the shaft she had come to know and love over the past mouth. Within seconds, he was shooting globs of bittersweet cum into her mouth. She swallowed his load, licking his head clean as she pulled off him and sat upright. The trucker was still beside them and as she blushed and shyly waved at the man, he blew his air horn again and Dave, laughing, sped up and passed him. * * * It had been a month since their first weekend together. Tiffany had been a nervous wreck the following day at school. Would Dave call her? She hated the three-day rule that was part of every romantic comedy or TV sitcom. So after a long day at work, a long bubble bath, and a long pour of pinot noir wine, she slipped into his shirt and tried to focus on a book in her tall stack of 'I want to read that' books. She was just about to give up and turn on the boob tube when her phone rang; she looked at the number and did not recognize it. Normally she did not answer, but she had a gut feeling that she would regret not answering this call. She almost squealed with delight when she heard Dave's voice on the other end asking her to dinner. She accepted, her voice betraying her excitement at the idea. After she hung-up, she began to worry about if she had seemed too eager. After all, something clicked between them. She also remembered all the times when she was a guy and calling a girl to ask her out. She had the empathy that only comes from shared experiences, and realized that he was in fact hoping to hear eagerness in her voice. That as much as she was hoping he was thinking of her and wanted to call just call her and not wait...and that he was feeling the same emotions. Why did dating have to be so complicated? Wednesday night came and Dave took her to an exclusive steakhouse, remembering that she had mentioned being from the Midwest and growing up on farm raised steak. She looked stunning in a little black dress, black nylons, and heels. The evening went great. She found out that he was a very successful investment banker. A guy came around with a selection of cigars and while it was obvious that Dave was a regular customer of the cigar steward, he was nervous. To make him feel comfortable she asked the steward if he had any Pardon 1964 Anniversary edition cigars. She giggled as Dave's jaw dropped. She found that teasing him could be fun so she continued by expressing a preference for Nicaraguan tobacco over Dominican tobacco. She also talked about reading in a trade magazine how the Anniversary edition cigars had been Box-pressed in the Cuban style. Once over his initial shock that an attractive lady would be conversant in cigars he offered to buy her one. She selected a 5 ½-inch cigar since it would be more ladylike and he selected a 7 inch of the same variety. He was pleased to discover that she had a fine taste in tobacco; the smoke was smooth and the flavor complex and satisfying. In addition, he did not realize until he looked across the table and saw her puffing away on her cigar just how sexy a woman could be. She blushed at the attention. "Why didn't you go for the bigger one?" Tiffany smiled. "Well darling, I thought about it. The 7 inch reminds me of you, but I got mine shorter so you didn't think I thought mine was equal to yours." The comment puzzled him at first, then it clicked and they shared a laugh. He was amazed at how easy it was with this woman to forget about 'it'. Dinner ended with a glass of scotch each. He told her she could get anything on the menu she wanted. However, she did not want to either take advantage of him or come off as easy. So she deferred to his choice. He ordered two fingers each of a 30-year-old Highland Park. She took her's over rocks while he preferred it straight. They talked about the finer things of life until way later than she should have been out. He drove her home, enjoying the feel of her nylon-clad legs as he drove and they talked. His hand never strayed past the lace hold-ups, even though she would not have minded had it did. He opened the door for her and walked her safely to her door. They shared a long, lingering kiss. "Would you like to...um...come inside?" She said, smiling sheepishly. He smiled. "Tiff, I'd love to. I really, really want to. But I want you to know, I'm not one of those guys who's all about sex. I like you...And I just want to show you I'm a good guy. Besides...it's a school night." He winked and kissed her again. "Good night, Tiffany." He said before turning and walking back to his car. She turned and went inside; kicking off her heels, she hurried to the window to watch him drive away. They had gone out several times since then, spending two of the three past weekends together at his apartment. That first weekend after their first date, they did not see each other or talk to each other much since that was his weekend with his son and they were not ready to break the news to him yet. He took her to see one of those supernatural romance movies that were popular with teens and with women in their thirties and younger. She rewarded him with a negligee and an evening of pleasure. She had also talked with Shelley her T-girl BFF over drinks the weekend Dave had his visitation with Eric. They had also met a new girl who had just moved to Portland from the UK, pretty young blonde named Jane. She was studying abroad and was looking to make new friends in the community outside of the University setting. She had been living as a girl for about the same amount of time as Tiffany despite being more experienced sexually. Tiffany was thankful that, while nothing was official, she was not on the market. Not only was Jane absolutely fabulous and stunning; she had that British accent that was just slaying the men at the bar. Shelley and Tiffany reaped the benefits since anytime a guy sent a waitress over with a drink they bought one for the whole table. Jane did dance and chat it up with some of the cuter or more charming guys, but spent most of her time around her new friends. The two women teased and congratulated her on her great catch. They also gave her some great advice on some of the more personal aspects of her newfound sex life. Jane told her about 'douching' and cleansing herself so she would no longer have to sprint to the bathroom and it would save her no small measure of embarrassment. Shelley explained about prostatic orgasms and the special g-spot girls like them had and that she was lucky to have a guy whose length and curve was just right to tickle the special spot. They also gabbed about such lady like topics as their men's length & girth, head techniques, and tasting notes on their men's seed. Thanks to her friend's tutelage, their sex life had gotten better and now they could snuggle instead of her frantically making her way to the potty. She also found that she was more relaxed and sex was becoming more pleasure than pain. She enjoyed the intimacy of missionary, but could tell he always seemed a little more sated when he took her doggy style. She found that she took enjoyment in his satisfaction as much, if not just a little more, than her own. At first, she did not have plans for Spring Break other than grading mid-terms and term papers. Then last Friday he asked her to go to his Lake House with him. She tried not to think of Dave as rich, but she was definitely starting to understand why some women would choose the life of a gold-digger. She wanted to get away; she had moved to the region from Missouri and had heard her grandmother talking about Hayden Lake growing up so she jumped at the chance to go. He offered to spend the week up there, but she thought that maybe that would be too much and she would feel like a gold-digger so she talked him into going up there on a Friday and coming home on Wednesday so they would have four relaxing, stress free days. ~ 2 ~ Dave's lake house was a log cabin that sat about 100 yards from the lakeshore. They arrived well past dark so she could not enjoy the view, but judging from the sound of the lake softly lapping against the shore it would be beautiful in the morning. He opened the door and after slipping back into her heels, she slid both legs out and taking his offered hand, she stood up out of his car. "It's a little cool out tonight, would you like my coat?" He said as he took it off. She smiled and kissed him on the cheek. The cool night air was teasing her nipples erect. Although she knew they were the only people around, she could imagine people in the woods watching her. While she knew she would be petrified to be put on display somewhere public, dressed in nothing but her bra, panties, and stockings she also secretly relished the thought. When she was dating her ex-wife, they had sex on her patio at the Catholic University she had attended as a man. It turned her on then, the idea of someone watching them fuck, her ex's legs clad in black stay-ups wrapped around her waist. When they were done, she pulled the covers away from her ex-wife's body exposing her to the world. "No thanks." She said and let him lead her to the cabin front door. She could tell he was enjoying parading her in the open even if there was no one around to enjoy the show. He opened the door and she stepped into darkness, using a dimmer switch he turned the lights onto a low, romantic level and led her inside pointing out things like which door was the bedroom and which one was the bathroom. She giggled spying a bearskin rug in front of a fireplace. He smiled, knowing what she was giggling at as well as what she was thinking. "Well," he said, sweeping her into his arms. "I'm going to bring everything in from the car." She started to speak but a finger to her lips silenced her. "Why don't you pour us something to drink from my liquor cabinet over there and wait for me on the rug?" She smiled. "Oh, one other thing Tiffany..." he said with a naughty gleam in his eye, "since you like to show yourself off..." he reached behind her and unfastened the bra/halter top thingy and slid it off her revealing her wonderful breasts. He stepped back and looked at his woman. She was beautiful in the dim moonlight. Her long dark hair down, swept back over one shoulder while on the other side she had it draped over her shoulder and breast so that the ends of her hair kissed her nipple. One side of her face was covered by her soft, silky hair giving her that classic seductress look. Her breasts were perfect, full and perky without being over large. She had curves in all the right places, which he knew had cost her a lot in terms of time, money, and effort. She had shapely legs that she was holding in that most femininely awkward pose that women took when they were feeling both bashful and horny. She was wearing a pair of black satin platform pumps that combined the classy upper of a traditional round-toed heel with the one and a half inch platform of stripper heels. It took all of Dave's inner strength to turn away from her and retrieve their bags. When he returned she was holding two glasses of red wine she had poured for them. He resisted the urge to just drop the luggage where he was standing and go take her, but he opted to put the bags away instead. He returned after just putting the bags in the closet, putting their clothes could wait until morning. She offered him a glass, but he refused it. "Baby, it's still a little cold outside. Let me start a fire." Secretly he enjoyed keeping her standing there holding the glasses of wine. He relished the glimpses where he could admire her perky breasts with erect nipples, beautiful face, or shapely legs that were only enhanced by the heels and the shimmer of nylon. They had listened to a book on CD of a popular BDSM romance on the way up here, which put him in a more dominant mood than normal, and the femininity of her soft and silent submission to his suggestions helped him feel more masculine. Something he would need tonight. As he glanced at her, his eyes would be drawn to the bulge in her panties. He felt guilty that she seemed to relish pleasuring him with her mouth and tongue; she even seemed to honestly enjoy just holding and admiring his cock. This was something no other lover would do in the past. His first girlfriend way back in high school would only do it in the dark; she did not want to see it. His first college girlfriend would rub him a little as foreplay to foreplay, but not dwell on it much. Lauren, his ex-wife, after awhile and after reading an article in a magazine did start making the effort to admire his cock and say a few quick things she liked about it before taking it in her mouth. Nevertheless, Tiffany on the other hand, would take about five to ten minutes to stroke it and admire the blood pulsing through the dorsal vein. Watch it grow in her warm hands, or rub it against her cheek as if it were an extra-special gift. It was as if she knew what a man wanted. He smiled a nervous smile every time he caught himself realizing why it made sense that she possessed this knowledge. Tonight, he had decided when he first suggested the lake house, was the night he would try not to be selfish. Tonight, he was going to go down on her. For her part, it was not something she was pushing. She had let him know that she did not have too much desire for her oral favors being returned. For his part, he was developing strong feelings for her and as such, he wanted to return the favor anyway. So tonight, he was going to eat her out. He had to think about it those terms, because it helped him deal with conflicting emotions. He was not a chauvinist or misogynist, but he had found that when he played the strong, dominate male role and she played the supportive, submissive female role he felt more masculine and more at ease with the fact that he was in a romantic and sexual relationship with a transsexual woman. And tonight, he would need all the help he could get. The fire was warm and comforting as it started to catch. He sat on the bearskin rug and patted the soft fur next to him, letting her know that he wanted her to sit down. She handed him a glass of wine and then slowly sat down next to him. He set his glass down on the fireplace and took her glass, setting it next to his noting which one had the pink lipstick on it. He kissed her, passionately, his hand exploring her breast. She closed her eyes, enjoying the taste of his lips and the feel of his hands on her body. She was ready to submit to him, to slide between his legs and pleasure him, as only she knew how. Over the past month, she had become intimately familiar with him and his penis. She would spend minutes softly kissing, stroking, and admiring it before sucking on it. It honestly did not bother her that he shied away from her girl cock; it was something that she was working on getting rid of herself. Having once been a straight man, she understood his feelings. Just as she was about to slowly start kissing her way down his neck and chest to her place between his legs; she felt his lips on her neck. His hands tugging her panties down. His soft kiss and tongue on her erect nipples. "Was this really happening?' She thought as he continued his Southward expedition of her body. Then his lips were at her belly button and still going. Dave let himself get lost in her body. The smell of her perfume. Her soft, smooth skin. He thought only about those things that made her a woman, and not just any woman...the woman he was falling for. As he slid her panties down, he cringed for a moment fearing the smell of ball sweat and a day's worth of filth. He knew how much attention he paid to his own hygiene...and he did not consider himself a slob. However, she did not smell as he had feared she would. This part of her smelled like the rest of her, except with a hint of the baby wipes she used to cleanse herself when she used the ladies' room. He did not look at her girl cock; instead he kissed it, wrapping his lips around it as if he were suckling a clit. He rolled his tongue over her clit head. She shivered and moaned in pleasant surprise. His Son's Teacher Ch. 04 "Oh, Dave..." she said, shivering with delight. "...you...you don't have to...but thank you...thank you...," she groaned as he continued going down on her. She was smaller than he was, maybe four and a half inches at most and more thin. She also kept herself shaved; her shaft and small balls. The smooth skin seemed so feminine despite being a cock. She wrapped her legs around his head as he pleasured her, locking her ankles together behind his head. Her heels rubbing against his bare back caused his cock to throb with lust. He groaned, in his mind he was pleasuring just another part of her pussy. He tried to lick and suck her as well as she could, paying attention to all the places she did. He found that her cock reacted slightly differently than his, different places turned her on than he. He softly lapped at her balls, which seemed to drive her crazy. She shivered. "Dave...I...I think I'm going to cum..." She slowly pulled away from him, leaning over to give him a deep kiss. "May I try something?" He shook his head 'yes'. She smiled. "Well then Darling, roll over please." He rolled over on his back and she slid on top of him, straddling him. His long, thick cock was rubbing against her she-cock. Her silky, nylon clad legs and feet softly caressing his bare legs. She leaned over as she began to ride him, her clitty rubbing against his manly cock, giving them both the same pleasure. She moved slowly, doing all the work, her breasts rubbing against his chest. They kissed and she suckled his neck softly. She would lean up, and his lips would find her nipples. They both moaned in delight. They were both so excited from the unexpected oral encounter, Tiffany more so, and she came. Her warm, shemale honey covered his cock adding to his pleasure as his own orgasm tipped over the edge. His own ejaculation sprayed a trail up both of their stomachs and even splattered along the bottom of her breasts. She stopped riding him and rested on his chest for a moment, bathing in their afterglow and feeling him holding her tight to him. After what seemed like way too short of an eternity, his grip on her loosened and she took this as a sign to slide down his chest and clean him up. He stopped her. "No Tiff, not tonight. Let's share a shower and go to bed." There was tenderness in his voice. A tenderness touched with gratitude for her willingness to do all and be all he wanted sexually, while never asking for anything in return. He had plans to explore their kinky side this weekend, but tonight he wanted to show her that she was part of this too, and he would not only take but give back too. They showered, letting warm soapy water relax aching muscles and wash away the day's cares as well as the more sticky reminders of their lovemaking. She washed him first, despite his early insistence on 'ladies first', but some things were just a woman's prerogative. She was grateful for his selflessness tonight and conquering one of his inhibitions on his own, but she did enjoy softly submitting to him. Feeling his strong chest as she rubbed him down with soap before rinsing him off with the shower massage. She saved his cock for last, knowing that it had been enough time for him to recover, and as it grew in her soapy hand she was not proven wrong. She took her time caressing him, watching it grow in her hands. She was kneeling in front of him as he came a second time. Not wanting to do the same thing over and over, she aimed his cock at her breasts, smiling up at him as he sprayed her tits with his seed. After his cock was rinsed, it was Dave's turn to wash his girlfriend. He started with her hair. He loved the way her hair felt, and had always thought washing his wife's hair was intimate, and romantic. Besides, he did like seeing Tiffany's breasts and belly splattered in his cum and was in no hurry to wash it off. Gently he washed and conditioned her hair, taking so much time that they began to run out of hot water, so after rinsing her hair of conditioner he turned off the shower to massage and loofah her with some bath gel that smelled like cherry blossoms. He noticed that her body was not reacting the same way as his, at first he worried that maybe it was because he was doing something wrong. Then he thought about some of the pills that he had seen her take during their sleepovers at his place. Curiosity gripped him, he tried to force the questions from his head but they were there and he could not get them out. "Tiffany," he finally asked, "may I ask a personal question." She looked up at him as he was caressing and groping one breast with a soapy hand while using a loofah on her other breast. She giggled. "I think we're beyond asking for permission, nothing is too personal." She smiles mischievously. "Mr. Monet." She called him this instead of Dave to highlight just how far they had come from the beginning. He laughed at her barb. "Okay, point taken." He squeezed her breast as he spoke. "Why is it you can make me cum a couple of times a night, but usually I can only make you cum once? Is there something I can do...better...differently?" She smiled and kissed him. "I am a very lucky girl to have a man like you." She stepped closer to him, wrapping her arms around his neck. He let go of the loofah and her breasts and wrapped his arms around her waist, holding her close. "No, it's not you. It's me." She winked as she made the cliché. "Wow...that almost sounds like a break-up." He said; half joking and half worried. She giggled. "No, no...not at all!" She exclaimed. "I have a British girlfriend who would snap you up in a London minute. It really is me...or my biology. The hormones I take to make me a woman...and give me my breasts...well they come with a price. I'm smaller than I used to be and I don't get hard near as much as I used to." She could tell he was aghast and feeling sorry for her. "And it's not a bad thing." She said, looking his straight in the eyes to reassure him. "Like I said, I want to be as much of a woman as I can. I cannot be that and keep 'it', and I'm going to get the surgery done...so if it shrinks and becomes smaller...that's not really a bad thing. As for arousal,...it's shifted. It comes from deeper inside me physically, emotionally, and even mentally. Now I understand the female cliché of 'fuck my mind before my body'. It really is different." Relieved that it was not something he was doing wrong he finished washing her, noting that when he lathered her clitty, she did not react as he had. Instead, she moaned softly and closed her eyes, just enjoying the tingling that came with her man touching her so freely. He rinsed her off and shut-off the shower. As they toweled off, they stole peeks of the other's body or kisses or quick caresses. The he took her hand and led her to bed where she slept naked next to him for the first time. ~ 3 ~ Dave woke up all alone in bed; he looked at the ancient alarm clock by his bed. Its red numbers displayed 9:48. He was just about to call for her when he heard her talking on her phone. "Yes, Jane...everything is going well. It is BEAUTIFUL here; he has this really awesome log cabin up here." Pause. "No...no I have not given him his surprise yet." Her voice lowered into a whisper. "Wait, he may be up yet...hold on..." He heard her stepping towards his bedroom door, the doorknob turned and he closed his eyes and pretended to be asleep. He heard the door open, only to softly click shut a moment later. He caught a whiff of her perfume and cherry blossom body wash. He smiled, wondering what the surprise was and letting his mind wander, drifted back asleep. * * * He woke up again and looked at the alarm clock by his bed; 11:21. He was greeted by the smell of sizzling steak and other delicious smells greeted him. He stepped out of bed and put on pajama pants and a robe. He stepped out of the bedroom and into the living room, he could see the table was made; scrambled eggs were already on the plates. She had a carafe of coffee and juice on the table. He heard the sliding glass door open behind him and he turned to see her come in carrying a platter with two sirloins. She was wearing a robe. He looked her over from head to toe. She had pulled her hair into a ponytail and adorned it with a gold colored hairpiece. Around her neck was a metal dog collar. He noticed a length of purple cloth peeking out from the robe. She was wearing nude colored nylons and a pair of high-heeled sandals. Dave smiled, imagining what was underneath the robe. "You're up!" She said and quickly set the steaks on the table. "Yeah...you too." He said, his eyes mentally disrobing her. She pulled out the seat in front of the plate with the larger portion of eggs. He took the seat. "I got you something." She said, standing before him, taking off her robe. Underneath she was wearing a gold-bikini slave costume from 'Jedi'. "Remember the morning you said you wanted to do her...and I wanted to be her?" She smiled. "I saw this online and ordered it...we both get our wish." He had to admit, she made a good slave girl. Her breasts were just a little too large for the brazier. She had a flat stomach and beautifully rounded hips that gave her an hourglass figure. He had learned that she had worked very hard at getting this body, and he was grateful the she was letting him enjoy it. "The heels and thigh highs is a nice touch." She giggled as she placed the larger steak on his plate. "Would you like coffee or juice, Master?" She asked playfully. "Coffee...princess." He said trying to get into character. He picked up the nicely folded napkin, which revealed a small leash. He smiled at the present; this was going to be an interesting weekend. She poured him a cup of coffee, took her seat across from him, and served herself a steak that was about half the size of his. As they ate, they chatted about his boat. It was getting warm outside and he had been looking forward to taking it out for a spin. As he talked about his Bayliner cabin cruiser, she began rubbing his leg with her foot. He guided it to his lap, slipped the sandal off, and massaged her foot. He opened up about his work and some of the office politics while she listened attentively. Over the last month, their dates had focused on her. He was curious about her and her journey from man to woman. However, he was largely guarded when it came to his own life. She slid her other foot up his leg towards his lap, his foot rubs always felt so wonderful. She had discovered a man who shared her fetish for feet and nylons. When he was finished, she cleared the table and started rinsing the dishes while he enjoyed the show. She was putting the last dish away when she felt a presence behind her. His arms wrapped around her and he kissed her neck. One hand sought out her breast, while the other traveled South, slipping under the fabric of her skimpy skirt seeking out something that was not there. Tiffany smiled as she felt him start to explore. Dave had gotten used to her tucking and the strange, almost natural feel of her. However, it was not there. Her skin felt a little different, something was off. It was warm and soft, but just did not feel like the rest of her skin. His fingertips inched between her legs and found something familiar, but unexpected. It felt like a pussy. "What the fuck?" His voice was confused. "Did...did you have an operation and not tell me?" Tiffany giggled. "No, Darling. It's called a vag-panty. I saw it on an online cross-dressing boutique." She felt his fingers exploring the prosthetic pussy, she had dabbed a little of the 'her's' lotion from a brand name lube. "I thought you might like it." "Is...is...it...fu..." He was shocked that she would do that for him, and a little curious. He had no idea that such a thing existed. "Faceable?" She tried to finish his sentence for him, pecking him on the cheek. "Yes...no...I mean..." he looked her in the eyes, this woman was so amazing. "I was going to say functional. But yes...is it?" She nodded and smiled with an inviting, come-hither grin. He smiled back, and clipped the leash onto her collar to lead her to the bedroom. Once there he just wanted to rip her clothes off and try out her new fake pussy. However, it was not every day that a woman offered herself to him to be the sex slave of his adolescent dreams. He kissed her and placed his hand on her head. Once he broke the kiss, he pushed down, pushing her to her knees. "Yes, Master." She cooed. She knew what he wanted so she slowly untied his robe. She kissed the massive bulge in his pants as she hooked her fingers in the elastic waistband of his pants. Slowly she pulled them to his ankles, his cock smacking her in the face smearing pre across her cheek. She nuzzled it for a moment, enjoying the feel of his warm, pulsing life against her skin. Slowly, she kissed the head. Her tongue lapping and exploring his head, tasting his pre. She glanced up from her knees, the look of satisfaction in his eyes made being his toy worth it. She kissed his balls, sucking one into her mouth and then the other. A tug on the leash let her know that he wanted her on her feet, she slowly rose. Dave could not take it anymore, he needed her and he needed her now. Once she was on her feet, he reached behind her, took off her bra, and flung it to the side. He pushed her onto the bed, pulling the skirt aside. She had not gone cheap on her prosthetic; it blended in nicely with her skin tone. He took a moment to explore it with his fingertips. It was warm and felt nice. She reached into the nightstand on her side of the bed, pulled out the blue tube of lube, squirted a dab into her hands, and started rubbing it onto his cock. He slid between her legs, while she guided his cock towards, rubbing it between her new lips as he started to push into her. For Tiffany it was more mental than physical, feeling him between her legs sliding in and out of her. It was like a dream come true, a man was inside her and fucking her pussy. She wrapped her legs around him, pulling him into her with each thrust. His lips found her neck and started suckling and biting, turning her face to one side, letting him give her a hickey. He was like an animal; she was being taken with a passion he had never shown her before. She looked forward to the day when he would really be sliding in and out of her, the day she would have a real cunt. Dave groaned, the He & She lube she was using was warm on his cock and really added to the sensation. It was very much like all the other women he had, it felt awesome. He was getting close; he pulled her close to him, her breasts pressed into his chest. "Fuuckk...Tiffany..." he moaned as he came inside her. Tiffany could feel his cock twitching inside the sheath of her vag-panty. She felt each time he spurted inside her. Then his lips were on her's, his tongue darting into her mouth. He held her there, letting his cock go limp inside her. Then she felt him move off her. He unclipped the leash. "Done with me already, Master?" She pouted. "No, my pet." He kissed her forehead. "I just want you to get me a beer." "Yes, Master." She said and left his bed. As she retrieved his beer, she could feel his cum oozing out of her and coating her upper thighs. She smiled, thinking that this was going to be a very special weekend indeed. His Son's Teacher Ch. 05 ~4~ Tiffany's world was black, almost pitch black although she knew it was still day. She tried to move, but could not. If she struggled too much the nylon ropes Dave had tied around her wrists and ankles would start to warmly chaffe. She could move her head from side to side and even lift it off the pillow. But she could not see anything through the thick blindfold he had put on her, she couldn't even tell if it was light or dark outside because she was sure she had heard him close the blinds and curtains in the bedroom. All she could do was feel. She could feel the cool kiss of the fan in the room as it oscillated, blowing air across her exposed breasts. The cum oozing from her vag-panty and pooling on the bed beneath her. She was drooling from the corners of the ball he put in her mouth, and could feel it trickling down her cheeks and into her hair. Finally, she could feel the slow progress of time as she lay there tied by wrist and ankle, spread eagle. She was waiting for the sound of his Lexus pulling up the gravel road to the cabin. She had heard him leave, but where he was going she had no idea. Furthermore, the more she thought about the more she realized that she did not know if two minutes or two hours had passed. She was learning that time had no meaning in subspace. * * * Dave took a picture of her tressed up, he was pretty proud of his handiwork with the rope. She could move a little, but not more than an inch or two in any direction. His heart was pounding in his chest. None of this was like him. He had never considered himself a 'Dom', but there was something about the femininity of Tiffany that made him feel more masculine and even aggressive. Along with this came a very strong protective urge in regards to her. He thought about this on the twenty minute drive into town. He was alive with nervous energy. The thought of what was waiting for him when he got back was making him very excited. But at the same time he worried about her safety; what if something happened while he was gone? He tried his best to push those thoughts out of his head. This was her fantasy; she had told him that she wanted to be tied up and left vulnerable. To be taken in such a way that she was not sure if it was her lover or stranger and to never know for sure. She had talked about how the idea of being shared appealed to her, but she was unsure about it. In the end, she had decided whether or not she would be would be left up to him. Yes it was her body, but it was also the body of his girlfriend. So if he did not want to share, she would not force him. He felt awestruck by the power and authority she was giving up to him. He grappled with whether or not he was worthy, but also felt more powerful and masculine for being so entrusted. And so he had tied her up and left her vulnerable while he ran errands. During their planning for this 'scene' she had said that she did not know anyone here, but perhaps he did. He remembered the gay couple who lived just a mile or two down the rode; and that they had gotten a divorce and Steve was now living at their lake house full time. 'Would Steve go for Tiffany?' he was thinking when his thoughts got jarred back to the present. "Dave! Is that you?" He spun around at the familiar voice coming from behind him, suddenly realizing that he was in the grocery store. His basket was already filling up with the few things he had come to get. Was he really that much of a space cadet, flying on autopilot? He turned to see James from work. "Hey buddy..." he said trying to switch mental gears. "I didn't know you were coming up here...where are you staying?" "Oh, just some rental." James moved closer, acting very un-James like, and whispered: "I'm up here with a girl." Dave was taken a back just a little. James was a real ladies man and often bragged at work about his 'conquests'. This must be serious if he's acting like a schoolgirl. "Oh? Pulling out all the stops...what is she, some sort of supermodel and you're avoiding the paparazzi?" He chuckled at his own cleverness. For his part, James realized that he was acting off and stepped back and spoke in a regular tone of voice. "No...it's just this girl is...special. She's really shown me there's more to life." As his friend spoke Dave recognized that he had a glow. James the Lady-Killer had had his heart ensnared. "Hey, are you up here with Tiffany? I'd like to meet her, we could get together and cook dinner. Do you want to come over, we don't have a lake view...but it's still nice." "Sounds good. But actually let's make it my place, I'm right on the lake. I have a hot tub..." 'Fuck!' he thought as soon as he said it, realizing that perhaps a hot tub could expose Tiffany's and his little secret. "...or go on a moonlit cruise on my boat." James perked up. "Sounds great, buddy! Let's get the meat since we're here!" Twenty minutes later they had steaks and brats loaded in Dave's car. "I'll see you at my place around five if you want to help cook, seven if you don't!" He said as he slid behind the wheel of his car and as he started the engine he pulled out his phone remembering to make a call before moving on to his next appointment. * * * Tiffany had totally lost track of time and had begun to snooze lightly when she was awakened by the sound of a sliding glass door slowly opening and then closing. The ball gag Dave had secured in her mouth had been loosely secured and in her sleep she had spit it out. "Dave...honey...is that you?" She said, her heart beating quickly, sensing she was no longer alone. She heard the other person become still. Her heart was pounding in her chest, a mix of fear and excitement. When they were planning this, her imagination overruled her common sense because it was all abstract. They were talking about safety plans and how she would be safe. But now. In the moment. Her mind buzzed with things that could go wrong. She heard movement again. Was this Dave just roleplaying? Did he know a friend and was she about to be used by a total stranger her boyfriend had selected for her? Or was it someone breaking in? The last thought is what terrified her. The first two would be wonderful and erotic. The last one; dangerous. What if the guy initially thought 'jackpot' and then found out that she was a transsexual? She shuddered with the thought. She heard the door open to Dave's bedroom. "Dave...honey...please..." She said starting to have second thoughts. The person stopped. Then she heard something set down on the dresser and then a distorted voice eerily filled the room. "Dave's not here." The recording, a voice distorting app that recorded what you said and played it back in the cheesy, menacing tone so common in B-movies, was their pre-determined signal that everything was alright. That it was either Dave or a friend. "But he said I could enjoy the pleasure of your company for awhile." The signal ended and she drew in a sharp breath, her body filled with erotic energy. She thought that the signal was the entire message, and she was surprised when it continued. "And he says he loves you." She shivered at the last. Then she felt the bed shake as the man crawled onto it and she felt a gloved hand clamp down on her mouth as another explored her body. Pinching and twisting her nipples, being rougher than Dave had ever dared to be. She squirmed and squealed against her bonds, but between the rope and the man's weight pressing down on her, there was not much she could do. She was helpless, but loving every minute. She felt his lips on her neck, then his tongue licking her. She normally did not like the thought, but now...it made her tingle. Her body relaxed, opening to the stranger. Then he released her mouth and straddled her. She heard the rustling of fabric, the loosening of metal and leather, and then the metallic zip of a zipper being pulled down. Then she felt a cock on her face. It was huge and thick. It was roughly the same size of Dave, but at the same time he was either really turned on or he had a friend who was just slightly more endowed than he. The cock was rubbing against her face between random dick-smacks. Each caress or smack smear precum on her. Then it was shoved down her throat as he began taking her. Tiffany loved Dave for his gentle touch, but right now she was being taken...used for another's pleasure. She knew this was not something she wanted every day, but the occassional fantasy was nice. Then he pulled out of her. Gloved hands held her head down and replaced the ball gag, tightening it this time. Her hips were lifted to just the right angle and she felt the stranger's cock slide into her. She cried out against the ball gag as the stranger began to take her, having his way with her body. The ropes greedily clung to her wrists and ankles as she felt the now familiar sensation of a man's cock inside her. She was just getting into the rhythm when the guy shuddered and his cock spasmed buried inside her. She felt him release inside her, then his weight as he rested on top of her. It was not his whole weight, he did not want to crush her. Then slowly as he began to deflate, he pulled out of her. She heard him step into the shower. She lay there, totally on edge. Her chest rising and falling as she tried to catch her breath. Then the fan oscillated across her once more. The sensation as it gently caressed her still swollen clitty allowed her the release of orgasm. She sprayed her own honey across her flat belly, breasts, and neck. She was a little disappointed that she did not have the range to hit her face, but overall she was pleased with herself. Once the stranger left, she slipped into a timelessness trance once more until she heard Dave pull-up and come inside. She could hear him try to stifle gleeful laughter as he took pictures of her all messed up, then he lovingly untied her and carried her to the bathroom where he had drawn a warm, candle-lit bath for her. They talked for a little bit, about how she enjoyed the experience and how relieved he was to come home and find her safe. Then he told her about their dinner guests, which got her very anxious about cleaning herself and the house to make both presentable. ~5~ Tiffany was busying herself in the kitchen making what she called cheesy potatoes; baked potatoes smushed with butter then spiced with her secret, garlic-y blend of salts and peppers, and topped with bacon, chives and a cheese blend. Dave came and went, ever so often playfully pulling up the hem of her dress. She had gone with a 1950s inspired halter dress that ended just above her knee. It was a bright blue nautical theme since she'd been told they may be going on the boat tonight. She had even bought a 'Dixie Cup' hat to go with it and a Captain's hat for Dave at a local gift shop. She wore white thigh highs with blue anchors decorating the hem. Her hair was down, draping down her back and over both shoulders to give her a classic 1940s glam factor. She could tell it was working on Dave. "I love the bright red lipstick." He said complimenting her on her make-up, which she appreciated since perfecting her techniques had taken years of practice and in the beginning she doubted she would ever do adequately. "Thank you, Skipper." She said and giggled as he wrapped his arms around her slender waist and started nuzzling her neck as she continued working. It was about ten till five, and they did not know if they had ten minutes or an hour before their guests arrived. "I could just bend you over right here, right now..." He whispered in her ear. She smiled feeling the boner in his pants rubbing against her as he gently pushed her forward just a little to make his point. She was about to protest, just a little when they were interrupted by the crunch of gravel underneath tires. The cabin had an open kitchen/living room floor plan so all he had to do was turn slightly to look out a bay window into the front yard. "Damnit." He said, he honestly did not expect James to show up. The guy was the type to show up late so he could just enjoy dinner without contributing more than a bottle of wine or a a desert from his favorite boutique bakery. He released Tiffany who, after slipping into her heels, turned her attention back to the potatoes so she could get them in the oven before playing hostess. James entered first, blushing a little and handed Dave a bottle of 2012 Ponzi Pinot Noir. Dave glanced past his friend, and then back wondering where this mystery girl was. James, noticing the glance grinned. "She's in the car, had to touch-up her make-up...specifically her lipstick." He winked and laughed, overhearing the piggish comment she flushed red a little thinking him a little prickish. She hoped the night would not be ruined by the jocularity she had always hated since high school. The screen door creeked open. "Ah here she is now." She heard the other woman's heels click on the wood floors. "Dave, I'd like you to meet Jane." She smiled at the coincidence until she heard an unmistakeable British accent say 'Hello'. "Jane is that you?" She asked as she turned around and spied her Beautiful Blonde British Best Friend (BBBBF for short). "Tiffany?" Heels clicked at the ladies rushed towards each other and hugged and giggled. Dave and James just stared dumbfounded as they processed what this meant. Giggling and holding hands, the ladies stepped to their respective man's side. Jane spoke first. "James, darling this is Tiffany...I've told you about her...how she's one of my special girlfriends." She emphasized the code-word they had established for 'ladies by choice'. James still looked stunned but it was Dave who realization dawned on first. "Tiffany...is this?" She nodded 'yes'. "So she knows..." She nodded 'yes' again. "...and she has...?" A final affirmative nod. His lips turned into a smile. He visibly relaxed, she had noticed his tension since he had gotten home from his trip that morning. She had to fight the reflexive feeling of insult and shame and realize that this was their first big test as a couple; presenting her to a friend who had the additional weight of being a co-worker. "So Tiffany is also a..." James began to ask. But Dave cut him short. "A woman? A special woman." Emphasizing the other couple's obvious code. James smiled, obviously relaxing. "That is such a weight off my mind." "I know how you feel." A short while later the two couples were out on the back deck where Dave had his grill going. The wine was open and the ladies were enjoying while the men drank bottled beer. The men hovered over the grill talking about work and sports. While the girls lounged on an outdoor sofa, heels kicked off and legs curled beneath them. "So how did you two meet?" James asked finally addressing the 500lb gorilla in the room, and still shocked at the unlikely probability of the coincidence. "Well, she's Eric's social studies teacher." Overhearing, Tiffany shot him an annoyed glance. Too much information; she did not know James so she did not know how he'd use the information. "It's okay." He said, turning his attention away from James and to his girlfriend. "He may be an ass, but he's a loyal ass." James playfully punched him in the shoulder. "What does Eric think of all this, you dating his teacher?" "Well, honestly he doesn't know." "We decided," Tiffany joined the conversation, "not to tell him until we decided where the relationship is going...if it's serious or not." "Is it as serious as you hope?" Jane asked, then brought a hand to her mouth realizing she had betrayed a confidence. Tiffany blushed at the reveal of something she had told Jane and Shelley in confidence. But then again, hanging out with this other couple had started to feel as relaxed and safe as 'book club night' with just the three girls. For his part Dave was grinning. He had been wrestling with something for the past two weeks. He had fallen in love with her, and was considering moving faster but was not sure she felt the same way. They were both adults who enjoyed each other's company and the pleasure of each other's bodies. But they had never really told each other where they wanted the relationship to go. They had had conversations about telling Eric, or about attending an upcoming work function at Dave's office where significant others were expected...but they were dancing around their true feelings. Now Tiffany's was on the table, and she was squirming not knowing his. "Actually," he said stepping over to her and topping off her glass of wine. "I was considering asking her to move in with me at the end of this trip." Tiffany's demeanor instantly brightened. "Really?" "Yeah." He replied, happy at her reaction even though it was not fully 'yes'. "I worry about you on your own." She knew what he meant. On a teacher's salary she could not afford the best place to live. It was not the worst, but the crime rate in her area, and her apartment complex, was on the rise. "Plus, you've taken over a drawer in the bathroom and a quarter of my closet. You spend every weekend there, so yeah." Tiffany bounded from the couch and wrapped her arms around his neck, kicking one bare foot back as she kissed him. "Is that a yes?" He asked. "Yes." She said. Still holding on to her man, she looked at Jane. "So how did you two meet?" "Well," Jane began. "I was at Stocking Tops, you know where we used to all hang out before you and Shelley got your stud muffins." she stared at Tiffany with a half-mocking/half-serious look of hurt and betrayal. Tiffany for her part accepted her shame as well-desevered, but took comfort a burying her face in her 'stud muffin's' broad, muscular chest. "And James steps up and asks if he could buy me a drink." "Wait, hold on a sec," Dave interrupted, casting a genuinely shocked look at James. "You were in Stocking Tops?" He geniunely incredulous. "Did you know what it was? Did you think it was a strip a club?" James blushed and looked down at his drink before answering. "Yes...I knew." He finally said, quietly and simply. "Look, here's the thing. Honestly, I'd kinda been on a losing streak with the ladies. One Friday after work I was thinking about what I was going to do that night. I'm about the only bachelor our age anymore at work, and honestly...I just can't keep up with the young bucks at work anymore." He sighed happily remembering a youth well misspent. "So I was on my laptop and searched for 'Portland Hot Blondes' and they had a pic from Tops. And yes, judging from the glam look of the ladies I thought it was a strip club. "So I went to the site, and I was shocked when I read the words 'transgender nightclub'. The women on the page were gorgeous. I could not tell they had ever been anything but. My curiosity was piqued so I decided to go." Dave moved the steaks to the coolest part of the grill so he could sit down and listen to the story. He was stunned that of all people James, the office lady-killer would knowingly try something like this. Tiffany followed him and curled up in his lap. "I was nervous, and it took me about three drinks to get my nerve up to actually approach someone." "Jane?" Tiffany asked, smiling. "No actually, she was the third girl I approached. The first two sensed my unease and kept me at a distance. Had Jane done the same, I would've just left." "That's pretty common right now. Two girls have gone missing in the past two week, rumor is it's the same guy, so everyone's guard is up." Jane added in her precise British accent. "So what made you accept James' offer? And do I know the girls?" Tiffany asked, suddenly concerned. Since she started dating Dave, she had stopped going to the club and was seeing less and less of her friends. "I don't think so, they were both new to the scene and Portland. Plus, I'd never seen James before. If he was the creep, I would have seen him before. Chances are he's not an established admirer, but on the same token he's probably been around to be glancingly familiar. James was neither so I took the chance...but I did watch my drink very carefully. His Son's Teacher Ch. 05 "After a few drinks we danced for a little while, and when we needed a break our hi-top table had been taken. So we hung out at the bar until a nice little booth in the back of the bar opened up." "It was strange," James took over the story. "I've never connected this easily with a woman. She talked about how she loved cricket and rugby. How she wanted to learn American sports especially baseball and football. Not only was I attracted to her body; I was attracted to her mind and personality." He blushed when he realized how shallow he had just come across. "I mean it was also more than liking sports, when we talked about what I did for a living it was more about actually listening to how my days went and enjoying the job. A lot of the girls I've hit on only seem to care about whether or not I'm well-off." "Maybe it's the type of girls you've gone after." Dave interjected. "At one point I realized that he had leaned in and kissed me." Jane brought the conversation back, not wanting to hear about her boyfriend's romantic conquests. "I kissed him back, we closed the bar without leaving that booth for the rest of the evening." "Good lord, I still remember how your legs felt!" James exclaimed. "Of course you do!" Jane said, laughing. "You're feeling them right now!" She said, pointing out how his hand had found its way past the hem of her summer dress. "Did you go home with him?" Tiffany asked. "No, instead I gave him my email and told him to email me if he wanted a proper date." "I tried waiting the three days so I wouldn't look anxious or desperate." "Silly rule!" Both girls exclaimed at the same time, and then giggling and according to some private rule filled each other's glass with wine and chugged it. James and Dave exchanged knowing smiles. "And it was not until the third date that I gave anything up." Jane said, looking straight at Tiffany who blushed a deep crimson. "Yeah, best blow job of my life!" James said proudly, making it Jane's turn to blush. Dave had been flipping and checking the steaks as they talked, and was ready to pronounce them done. They followed Dave and the meat inside to the table Tiffany had so carefully set. The dinner conversation flowed from topic to topic, but the guys would often come back to ponder how it was eaiser with Tiffany and Jane than other girls. Perhaps it was they had more of a frame of reference for what guys wanted and needed. It would also come back, several times, to the topic of how well they fellated their respective man as proof. Despite the initial embarassment, the girls did not really mind that the men were discussing them as a special class of female. They still regarded them as females and not freaks or rejects as some people close to them had when they started their respective transformation. They were also just two couples who shared a special bond enjoying a typical dinner with good friends. * * * After dinner Dave and James retreated to a sectional couch with recliners. Before starting clearing the table with Jane's help, Tiffany refreshed the men's drinks. Dave turned the TV to one of the light jazz stations and the discussion turned to office politics & gossip, sports, and the girls. James admitted that while he was not ready to take the step and invite Jane to move in, he was open to a relationship; which he had not been in one for quite awhile. Finished with their own girltalk in the kitchen the ladies came and joined the men in the living room. Not content with sitting, they started dancing with each other. They danced to the slow jazz, their bodies gyrating smoothly in time with one anothers. Jane was the more aggressive one and slide her hands all over Tiffany's body. "God I missed dancing with you!" Jane said, her accent giving everyone in the living room chills. Then she leaned in and kissed Tiffany, deeply...with tongue. The girls stopped dancing and just held each other, kissing passionately. Dave was the first to cough, nervously. They broke their kiss and, still embracing one another looked over at their men. They were all smiles, and had obvious hard-ons. Jane released Tiffany and they lightly stepped over to their men, their bare feet softly padding against the wood floors. "You know, James and I were just trying to settle something." Dave said as he wrapped his arms around Tiffany as she sidled up close to him. "A matter of grave importance." His friend said with a mischevious grin as Jane snuggled in close and he idly began pawing at her breast. "Oh? And what could that be?" Tiffany asked. "Which of you gives better head...or is it because of how 'special' you ladies are...you'd be about the same." Dave said, smirking knowing that on top of being submissive and taking pride in her abilities to please she also had a deeply buried vain side. She would want to be the best...not just 'about the same'. She played her part just as he expected her to. Her expression changed almost imperceptively, but the slight twitch as the corner of her smile betrayed the effect of his words. "And how can we solve this conundrum?" She asked, trying to sound sweet instead of annoyed and a little insulted. James cleared his throat, he and his friend were in this together. He would not let Dave take all the heat. "I suggest we swap. Jane would you mind sucking Dave's cock while your BFF sucked mine?" Jane took a moment to answer, to evaluate how the other couple reacted. Dave was grinning like the Cheshire Cat, so she knew he was in. No-duh! She thought to herself; he is a man after all. Tiffany's face was a little more difficult to read. She could see her friend weighing her options. Then she smirked; the smirk that at the bar meant: fuck it...let's do something crazy and fun! Jane thought to herself how she had missed that smirk these past few weeks. "Okay." She said with a smile and rose to her feet. She decided to up the ante and started to slide out of her dress. "Let me help." Tiffany said, rising to her feet and pushing Jane's fingers off her dress' zipper. Unzipped, she slowly pushed her friend's dress off her followed by her bra. Jane stood before everyone in nothing but her thong which revealed her tiny erection. "Fair is fair." She said, stepping out of the dress now pooled at her feet. She started unbuttoning Tiffany's dress, pulling her to her at the same time. She leaned in and kissed her friend one more time, more agressively...passionate this time. Her hands worked Tiffany's dress, sliding it off her. Then the bra. She played with her friend's breasts. She had always been a little jealous of the American's boob job. "Ahem." It was Dave again. They could hear their men squirming against the leather of Dave's couch. "I thought you ladies had a contest to win?" He asked, knowing that he did not have long if the ladies kept up their show. "Okay, Darling." Tiffany said, her voice cooing with an edge. "Let me get on my knees for your friend." She stepped between Jame's spread knees and began freeing his cock from his pants and underwear. She glanced over at Jane as she did the same. She leaned over and licked the pearl of precum that had formed at James' head. James was longer than Dave, but nowhere near as thick. She found herself wondering how it would feel inside her. "First girl to get cum, wins!" James gleefully proclaimed as he felt Tiffany's tongue sliding down the length of his shaft. He twitched, almost sliding out of her hand. She smiled at the reaction, knowing she was probably going to win. She glanced over at Jane. The blonde was taking the opposite approach; she had inhaled Dave. She was deep throating him, furiously pistoning her head off his cock. Her tongue snaked out and quickly lapped at his shaft and balls as her face bounced up and down on his cock. She made squishy gagging noises as she took the thicker cock. Her eyes were wide, trying to not gag on the thickness but failing. Tiffany realized that only did she want to win, she didn't want Dave to cum so quickly. It could potentially spark jealousy on her part, temptation for him, or worse: both. She began to lick and kiss her way to his tip while caressing and fondling his cum laden balls. She purred, her voice reverberating against his cock. She wrapped her lips around his cock and looked up, fixing him with her eyes as she slowly slid down his length. She bobbed up and down his length as her tongue worked his magic. She glaced over to her girlfriend sucking her boyfriend's cock. Looked at her boyfriend's face; glazed over in ecstacy. She doubled down on sucking James' cock. As her head went up, her hand went down squeezing gently. As her face pressed more of his cock down her throat her hand moved to meet her lips. All the while her tongue danced along his cock. Then she felt the twitch and smiled. She glanced over at Jane, her eyes were wide. She knew what Tiffany's smile meant and it meant she had lost. Tiffany felt the cock in her mouth swell and spasm as it shot hot jizz down her throat. She pulled off until her lips were securely sealed around the base of his cockhead as he finished cumming in her mouth. Once she was sure he was finished she pulled away. His cock was red with her smeared lipstick and glistened with her saliva. For her part she smiled and opened her mouth to show off her reward before smiling and giggling mischievously. Jane pulled off Dave's cock, but continued to stroke him as she watched Tiffany gloat and show-off. "You whore!" She said in a half mocking, half disappointed tone. Then she squealed as Dave, unable to hold it anymore, erupted across her face. His first shot landing in her eye and cheek. His next spurt in her blonde hair, and his final shot splattering across her breasts. For their part Dave and James looked at each other with expressions that conveyed a sense of shared luck and fortune. They also realized that while the other's girl was an amazing cocksucker; they still preferred their special 'girl'. Tiffany and Jane rose to their feet and grinning and giggling like school girls as they hurried to the restroom to wash the cum off skin & hair, brush teeth, and re-apply make-up. When they returned to their men, they were clothed the way they left: in panties and nothing else save Tiffany's thigh highs. They brought their men a beer and cuddled in next to them with a glass of wine each. For the next hour they laughed and talked and stole kisses as the men caressed their smooth, feminine bodies. Then the old, rustic wall clock chimed midnight. Everyone was getting tired, but also a little horny. Tiffany insisted that James and Jane stay in the guest bedroom. They did not even put up a pretense of declining and protesting about 'intruding'. Fifteen minutes later Dave and Tiffany were sliding into their bed when they heard the soft moans of Jane and the low grunting of James as they made love. Dave smiled at Tiffany as he took her in his arms and pulling her into bed removed her panties. Moments later she was moaning in harmony with Jane as Dave's grunts joined his friend's. * * * On the ride home Tiffany could not believe what had happened. Yes getting out on the lake on Dave's cabin cruiser was amazing. It was made better by sunbathing topless with her best friend as their boyfriends grilled on the back deck of the boat. Even better was the alone time she spent with Dave. Everything was perfect. She was happy. He was happy. They loved and respected each other for who they were. And she was going to move in with him at the end of the month. They were about an hour away from her place when she looked at him and started unbuckling her seat belt. "I love you Dave." She said, smiling and studying his face. He smiled a big, happy smile. "I love you, Tiff." He said, stealing glances of her from the road. She slid closer to him in the car and leaned over. For the high school social studies teacher Spring Break ended the way it began: with the cock of one of her student's dad's cock spasming and cumming in her mouth.