6 comments/ 92359 views/ 2 favorites My First Encounter By: cherrysilk I constantly thought about how feminine and desirable men might make me feel if they looked at me as a girl. I decided that the only way I would ever find out was to stop dressing privately at home and go out into the real world as a woman. I had lots of dresses and lingerie, but I just had to get some new clothes for this excursion. I went shopping, and I bought the prettiest blouse, a lovely skirt, a darling slip, sheer nylons, a pair of sling-back sandals with 2" heels, a necklace, earrings, an ankle bracelet, and a pretty little purse. The blouse was a pink silk poet's blouse with a ruffled plunging neckline and satin cuffs. The skirt was a baby blue linen sheath. The slip had a frothy lace bodice and hem, with satin ribbon bows worked into the lace. The necklace and earrings were crystal drops, and the ankle bracelet was very thin, fine gold, with a tiny crystal heart charm. I was bound and determined to have a real experience, no matter what. My feelings were so very strong! I took a long bubble bath, brushed my blonde ringlets until they shone, and made up very carefully. Then I got all dressed. When I was done, a little of the lace from my slip showed at my neckline. I thought I looked very pretty. I put on my new spring coat to hide my figure a bit. It had a satin lining and felt so feminine. Then I picked up my new purse and went out. I walked to the train, to go into into the City. At the station, I could feel men looking at me, but none said anything to me at all. My coat did not let them really see me. All they saw were my legs and heels, the bulges in my coat that were my breasts, and my face and hair. On the train, I still got the feeling that men were eyeing me, but no man sat in the seat next to me. It was so wonderful just to be out as a woman. That feeling, all by itself, is so marvelous. I got off the train and strolled out onto the street. The feeling that men were looking at me was even stronger here. Of course, there were lots more men. I decided to go to a movie, so I went up to a nearby theatre. There was an older woman in the kiosk, and she looked at me and smiled warmly. "Don't you look pretty today, dear!" she said. I was so complimented! This was a woman. Telling me I looked pretty! I was on cloud nine. She gave me my ticket and I went in. It was warm in the lobby, so I opened my coat. The ticket taker inside was an older man, maybe in his sixties or seventies. He looked me up and down with great admiration. He made a point to touch my hand as he took my ticket. He was so obvious! I was positively thrilled. Inside, in the dark, I removed my coat altogether and hung it over my arm. I slowly began to climb the carpeted steps to the balcony. There were only two or three people sitting up there in the late morning, and I wanted to savor the feminine feelings I was having because of the two people I saw coming in. About halfway up, in an aisle seat to my right was a very handsome young man. He glanced up at me, and I could see that admiring look in his eyes, even though he was no more than eighteen at best. I lowered my lashes and kept climbing, but more slowly. I could actually feel his eyes on my skirt as I went up the steps past him. I just KNEW he was twisted around in his seat watching my bottom sway as I climbed. I sat in a row about five above him, on the other side of the aisle. By then, he was watching the movie again. I placed my coat and purse on the seat behind me, crossed my legs, and let one high heel dangle out into the aisle. I made sure my skirt slid up my thigh, so that a tiny bit of the hem of my slip would show. Sure enough, in a minute or two, he swiveled around in his seat. I could tell he was surprised to see me sitting so close to him, because he turned back very quickly, like he was caught looking. My heart was pounding. My feelings were so indescribably feminine! I had never felt so much like a girl before in my whole life. He looked back again, and I demurely lowered my lashes. Through my eyelashes, I could see he looked at me longer before turning back around. The next time he turned around to look at me, I smiled softly at him. He abruptly got up from his seat and went out. I was crushed! I thought I was going to have a genuine encounter, and I felt sort of spurned. But that is an emotion too, and I love strong emotional feelings. Ten or fifteen more people had come up into the balcony since I arrived, some men and some women, but none were seated near me, so I began to look around to see what I could see. I was amazed to see my young man come back in again after about five minutes. Instead of leaving as I thought, he had just gone out for a while, perhaps for a drink or to go to the men's room. My heart fluttered again, wildly. He came back up the steps, but he did not stop at his row. Instead, he came all the way up to mine and stopped! He bent over me. I knew he could smell my perfume and see my bra down the neckline of my blouse from that angle. He whispered, "Pardon me, Miss," and started to pass into my row. I put my legs out into the aisle, and he slipped past me and sat in the seat one away from me, leaving an open seat between us. There was no one else in the whole row. I looked at him, and he looked at me. "Hello," I whispered, and slid into the seat next to him. I couldn't believe what seemed to be happening. It was just as I had always dreamed it would be. He smiled and put his arm around my shoulder. When his hand touched my silk blouse, it was like an electric shock. No man had ever touched me as a woman before. It was incredibly exciting! I couldn't help snuggling up next to him. I looked at him and could see what he wanted in his eyes. Oh, I wanted it too, so very much! He leaned over, and I caressed his cheek, fluttering my lashes shut. He had a sexy little stubble, and my heart began to pound. Then, he kissed me. My arm slid up around his neck, and I responded. This was what I had wanted since I was a little girl! A man treating me as the object of his desire. His kiss was intense and very passionate. He moaned deep in his chest and kissed me like I was the answer to every dream he ever had. His hand moved to my skirt, and I got scared. He was sure to find out if he touched my panties! I took his hand in mine and moved it to my breast. He stayed there, fondling my bra through my blouse as he kissed me. It was a long, lingering kiss, filled with his desire, and it thrilled me. I reacted to his kiss just as I had always imagined, with a woman's emotions. I felt extremely feminine, and it seemed like I excited him, and that was so satisfying to me. What also thrilled me was the way we appeared to any people who might have looked over at us kissing. I realized anyone who saw us would never doubt that the girl he was kissing so passionately as a beautiful, desirable woman. The thought that everyone was just automatically treating me as a total female was what really fulfilled me and made me tremble with excitement as I kissed him back. He kissed me for a very long time, then almost reluctantly moved slightly away. He was breathing very heavily, his body trembling like mine, his hand still on my blouse, so I knew I had affected him a lot. He hugged me tight, and I laid my head on his shoulder giving him tiny, soft butterfly kisses on his neck. I had never, ever felt so completely, absolutely feminine before in my life! That kiss was the most exciting experience I had ever had. I knew if I stayed with him much longer, he would insist on getting far more intimate. After all, the first place he had tried to put his hand was on my skirt. This would probably have been my downfall, and I was pretty sure I was feeling much too feminine to control him, or myself for that matter. I whispered, "I have to go to the ladies' room, darling," making it sound like he was the cause. He took his arms from around me and smiled. I smiled back, very sweetly, picked up my coat and purse, and went up the balcony steps to the girls' bathroom. I could feel his eyes on my bottom all the way up, so I exaggerated my walk slightly to please him. I had never been in a ladies' room before, and this one was really something. It was two rooms, really. A room lined with mirrors, vanities, and cushy little seats, and further in, an actual bathroom. I could see that my lipstick was really smudged, so I sat down at a vanity and began to fix my makeup. A lady came in, and in the mirror, I saw her smile when she saw me repairing my lipstick. I think she was one of the people in the balcony, watching him kiss me. That made me feel very, very good. A final check in the mirror showed that my makeup looked pretty again, so I slipped on my coat and reluctantly left the theatre, letting my good sense rule my emotions. All the way home on the train, I wondered what would have happened if I had gone back to him as I dearly wanted to. And I still do. My First Encounter With a Man I found myself there more by accident than on purpose. Or so I tell myself anyway. The fact of the matter is that I was yearning for this new experience for quite some time. There was just something enticing about man to me even though I was (and still am) quite the ladies man. For years I was "curious". My first true step was to buy a Bi video. The sight I found, repulsive the first time though. Seeing a man penetrating another man nauseated me. I put the video away. In time enough I cam back to it and watched it all the way through. Then again, and again until I was desensitized to the new reality of man on man sex. Soon I found my distaste replaced with a dark, forbidden arousal. Before long I was purchasing gay mags and dildos. I would ride the dildos as I masturbated to the videos and magazine images. Soon my passive curiosity started moving to the next level and began to wonder how to turn my fantasy into reality. The online world opened up to me and soon I was chatting with would be partners and surfing sites containing information on cruising spots. Before I knew it I was cruising the local hook up spots - not so much to pick some one up or be picked up, but to see who was picking up who and how it was done. Adult bookstores proved my favorite. Indoors, better lighted and safer feeling. Loitering in the magazine section I would make eye contact with guys how would then immediately try to lead me to the back but my courage failed me each time. I grew to love the booths. The smells men left behind, sometimes the spray marks and dripping semen on the walls aroused me in a very visceral way. I quickly took to a favorite bookstore investigating in at different hours on different days wanking off to gay porn on each visit leaving my evidence for the patron behind me. One Saturday morning I stopped in on a whim and found in much brighter and busier than usual. Several guys were standing by the entrance to the video booths as if on a scheduled rotation. The thought crossed my mind but I immediately dismissed walking straight to the back making no eye contact. The booths in the back were surprisingly empty given the amount of activity in the front of the store. Usually I would walk to the back getting lost in the dark maze of halls and doors but this time I stopped midway down the main corridor and took a booth. As always I would lock the door behind me. Inserted a 5 dollar bill and skipped through the channels until I found two hot guys sucking each others cocks. Immediately began to stiffen and took a seat as I was dropping my pants. Then I saw it. My first gloryhole was sitting just left of the waist level monitor that showed the envious picture of a guy with a rock hard dick sliding in and out of him mouth. I was shocked. Everything I had read and fantasized about was right there in front of me on this unsuspecting cool Saturday morning. My excitement turn to fright; almost terror when the thought of some one entering the booth next to me raced through mind. I didn't know what to do. I contemplated leaving and taking another booth when a tongue flicked up and down through the hole. "What the hell?! I never heard anyone enter! What do I do?" Momentarily paralyzed I stood there staring not knowing what to do. In an instant, the tongue was back flicking up and down followed by an eye peering up at me. I found my self moving for the hole and sliding my semi-hard cock through it. I felt vulnerable and not in control, the fear and terror were back in full force but I felt equally committed. In a sobering instant a warm mouth took hold of my cock and my dread was replaced with the pleasures that only a man can bring to another man. I leaned further and further into the wall trying my best to feed him every inch of cock I had to offer. I did not want any millimeter of me dick to miss out on what was finally happening to me. It was my first blow job from a guy and it was already the best blow job I had ever had. He sloppily worked my pole up and down taking it fully into his mouth as I practically tried to climb through the wall. I could feel myself readying to explode but I did not want this incredible feeling to end. I withdrew and bent down. Excited and invigorated, I could not let this opportunity pass without tasting my first dick. Before I was on my knees good, a short, fat cock appeared before me. I was no longer in control of myself. It took him into my mouth and tasted another man for the first time. I absolutely loved it. I sucked him in quickly and worked him the best I could wanting to return the joy he bestowed on me. I stroked and sucked him. I could feel him pressing against the wall. His hard, wide cock filled my mouth nicely. It's fleshy firmness exciting me into sucking him fast and harder. His cock grew. Before I even knew what was happening the warm flow of his cum began to fill my mouth. I never prepared myself for that moment and I was again in shock at what was happening. I continued to let him shoot his cum into my mouth, some of it beginning to run down my chin. In an instant he was gone. I knelt there looking through the hole as the door opened and closed with a mouth full of his semen. I felt like such a degraded slut. I spit in the empty waste basket and stood back realizing I was still rock hard. Just seconds latter I heard the door open and close once again. This time not a tongue but a figure jutted through. I could not help but feel compelled to oblige. This time my fully erect cock went through the hole without hesitation. A cold hand began to stroke me back and forth. Then I felt it again. A warm mouth taking me in. Forcing myself against the wall I let him service my cock with his mouth and his now warm hand. The brewing in my nuts was back. The explosion was soon to come. He sensed it and sucked me faster and harder until I shot wave and wave of cum into his awaiting mouth. I was the single best orgasm I have ever had. Once again I knelt down, still trembling and waited for my second taste of cock and semen. His long slender cut cock was dripping with pre cum. Immediately I lapped it up sucking only the head of his cock trying to extract every succulent drop I could get before going to work on that long pole of his. His taste was salty and dank. I took as much of him in my mouth as I could but he was far to long for a novice such as myself. Harder I worked him and he began to work his cock in and out of my mouth. I sat there letting him fuck my face through the hole when I could taste more pre cum. I started stroking my dick in the excitement. I could hear him getting close, his moans beginning to drown out the porn playing in the adjacent booths. I wanted his cum so bad. I pressed in towards the hole as far as I could without gagging on his cock and sucked hard every time he forcefully entered my mouth. He blasted cum before he reentered my mouth giving me a hard, warm blast of cum that splashed off my cheek and glasses. He slammed back into my mouth and shot a steady stream that almost made me choke. I clamped my mouth around his cock allowing him to finish as I swallowed over and over. I sucked him until I felt I got all the cum he had to offer me and took his cock and wiped his cum from my face into my mouth sucking him clean each time. Just as quickly as he arrived, he was gone. I finished stroking my cock and shot my nutt on the floor to the before unnoticed sound of two guys in the next booth fucking. I cleaned myself up the best I could and walked to the car savoring the warm salty taste left in my mouth. I do so love the taste of cum. My First Encounter With Jennifer This is the first in a series of stories based on my relationship with Jennifer, a co-worker and married mother of two with whom I had a long-distance affair for several years. It was late and the evening air in south Florida was warm and muggy, and the club was teeming with co-workers out blowing off steam after a long day of meetings. I was wearing shorts, one of my favorite Nat Nast shirts, and flip-flops, and in spite of my dress, I was still a little sweaty. I was squeezed in between folks, leaning over the edge of the bar trying to get the bartender's attention, and next to me was an attractive woman, with a come-to-me-big-boy smile and a twinkle in her eye. The club was very loud, and I practically shouted out "Hey, I'm Dave, from San Francisco." She said "Hi, I'm Jennifer, your company librarian." "Oh, so you're Jennifer. You've been a great help to me," I said. "So where are the glasses?" I asked, my tone mockingly serious. "Only in the library," she said playfully. The annual company meeting was always a raucous affair, bringing together hundreds of employees from across the country for three days of meetings, training, and lots of evening fun. There wasn't much competition between offices, so we worked with folks from offices across the country, and this was the case for Jennifer and me. We had talked on the phone and e-mailed countless times as she had helped me by track down articles and other publications needed for analyses I performed for my clients. She was always helpful and friendly, but not too chatty, which I appreciated. Jennifer is an attractive mid-40's dirty blond, about 5'4" tall, 115 pounds, emerald eyes, and, as I learned that night, a great throaty laugh, a kinky side, and an ass to absolutely die for that she likes to show off. She is married and has two boys, one in high school and one in college. I am single, in my late 30's, 6' tall and about 225 pounds. I have a full head of brown hair, hazel eyes, and an athletic build. The club was pulsating with music, and the floor was packed with colleagues—young and old, single and married—that were playing like sailors that just got off a six-month mission at sea. Jennifer and I drank and danced for an hour or so, and she was very flirtatious and loved to wiggle her sweet ass. During one slow song, I played a little grab-ass with her, and she delightfully rewarded me by grinding her hips into me and pressing her crotch into my thigh. At last call, I asked, "Would you like to grab a cab instead of waiting for the shuttle bus?" She responded, "Of course." Her eyes were on fire and had that knowing look of a woman who was focused on getting what she wanted. The cab ride back to the hotel wasn't even 10 minutes, but it seemed like forever. We were awash in that strong sexual tension that makes every minute seemed to move like an hour. Besides the main original hotel, there were several newer buildings behind the hotel that had larger, more private rooms where she was staying. After leaving the cab we started walking and I playfully asked, "So what do you want to do?" She responded by turning to me, with that fire in her eyes, and reached up to kiss me and reached down to rub my cock through my jeans. "I always have a little fun each year at the meeting, and you're going to be my fun this year," she whispered. She told me her roommate wasn't arriving until tomorrow, so off we went to her room. The anticipation was killing me, I was on edge, and all I could think of was ravaging her. Once inside her room, we fell to the bed kissing and groping like there was no tomorrow. Mouths and tongues and hands were a blur: kissing, swirling tongues, sucking her tongue, feeling the intense heat emanating from her. My cock was hard as iron, straining for release, and her hands were raking through my hair. We peeled our clothes off and felt the immediate adrenaline rush from our intertwined naked bodies. I rolled her onto her back and started tonguing her hard, tender nipples, taking one into my mouth, gently sucking it, then swirling my tongue around and around, then gently biting and tugging it. I had another hand pressed against her warm mound, feeling her vast wetness. She was panting and running her fingers through my hair, and her thigh was rubbing my hard, dripping cock. "Oh, yeah, suck it," she whispered breathlessly. Devouring her, I pushed her swollen breasts together, and tonguing both nipples at the same time, and then went back and forth from one to the other, driving her to the edge of ecstasy. Her moaning intensified and I could feel her nails pressing into my back and her hips starting to buck. Encouraged by her erotic responses, I swung one leg over her, straddling her, and lifted my head up. Looking into her molten eyes, I began to gently knead her aching, swollen breasts. My cock was dripping onto her tummy and I slowly slid it back and forth as I rolled and tugged her nipples. I said, "You're a dirty girl, Jennifer." "Yes, I know" she said. Increasing the intensity of the nipple play, I asked, "Have you always been a dirty girl?" "I am a very dirty girl and I just don't know how I got to be this way" she said playfully. "Are all librarians like you?" I asked. "You didn't know it was part of the trade?" she asked. I continued to knead her breasts and work her nipples, rolling and tugging them a bit harder. "Oh God, oh God, make me cum," she pleaded. I slowed down the nipple play and put saliva on my hands and started rubbing her breasts more gently. "I'm going to have my way with you, dirty girl," I said. She opened her eyes and looked at me and said submissively, "You can do anything you want. Anything." "Ok, dirty girl, suck my cock," I said. I laid down and she got down on her knees between my legs, took ahold of my swollen cock, looked up and me and said "You make me feel like a dirty slut," as she engulfed my hard wet cock, her mouth sliding up and down as she gently twisted her hand. 'Oh my fucking God' was all I could think as I watched her go to town on my cock, the intense sensations percolating into unbridled lust. She sucked my cock like she hadn't had one for ages or it was one of her most favorite things in the world. She looked up at me proudly, her eyes smiling, and then slid down to my balls and starting licking them. She slathered them with love, and they ached for release. "Lift your legs up, baby," she said, sounding like she knew what she wanted. I lifted my legs up and held them in the air as she lowered her head and started tonguing the sensitive area between my balls and ass as she slowly jerked my cock. Then to my absolute delight she moved to my asshole and starting loving up on it. She rimmed me and slid her tongue in my ass, making love to my backside. Soon thereafter I felt her finger slide into my ass and begin gently rotating, which would have made me blow my load except for the fact that I had to piss and the alcohol had numbed things a bit. After another minute or so she she swung herself around into a 69 so her glorious hot pussy was on my mouth. Her soaking wet pussy was hot and tasted clean and musky. I swirled my tongue around her swollen clit...around and around and around. She had taken my entire cock into her mouth and was sucking me urgently and passionately. After a couple of minutes, she got off me, turned around, scooted up so she was kneeling over my face, reached down, spread her pussy open and said, "Eat me, baby, I want to watch." I slowly swirled my tongue around and around her clit, and she urged me on with dirty talk. Her hands were on her breasts, kneading them, rubbing her nipples. Her breath became very short, her legs squeezed my chest, and she started to moan and then cried out as she started to cum. Her legs trembled she came and came and came in a series of short intense orgasms. "You are a very dirty girl," I told her, my face soaked with her wetness "Of course I am," she said. She reached back to stroke my cock that had softened up a bit, but I told her I needed to pee. I got off the bed and told her to come with me into the bathroom. "Kneel on the floor, nasty girl," I told her. She got down on her knees, her face just inches from my cock, and looked up at me. She was radiant, and everything in her submissive and knowing eyes told me that she was mine and that she would do everything I told her to do. Power and lust were rushing through me, I was breathing heavily, and I was completely focused on the moment. "Open your mouth," I told her. Maintaining her eyes on mine, she opened her mouth, and I asked, "What am I going to do to you, dirty girl?" "Piss in my mouth," she said. I asked, "And what are you going to do with my piss?" Looking up at me, she swallowed, and then cast her eyes down, and said, "Swallow it." "Look up at me, slut," I said. Holding my cock, looking down at her, crazy lust in my eyes, I slowly peed into her mouth, and then stemmed the tide. "Close your mouth and swallow it," I said. She swallowed that mouthful, and then we repeated the perverse, degrading act two more times. I asked, "Do you like my piss, dirty girl?" "Yes," she said. "Then hold your hands together," I told her. I filled her cupped hands up with my warm piss and then said, "Rub it all over yourself." She looked at me with half-shut eyes as she rubbed it all over her tits and tummy. And then one of her hands fell to her pussy and she started rubbing herself. "I've never been so turned on," she said submissively. As she brought herself off, I emptied myself all over her tits, the warm piss running down between her legs. I was crazed with lust, seeming to be in unparalleled state of mind. I started stroking my cock, and it quickly became hard, engorged with a life of its own. "Fuck me," she said. I told her "Come on, dirty girl, get up, face the mirror, and pooch your ass out." I admired her beautiful backside and knew it was mine to take. Positioning myself behind her, I grasped my hard-on and slid it into her buttery pussy and slowly, very slowly started fucking her. Her pussy felt like a warm velvet glove. In the mirror, I could see her flushed face awash in pleasure as I fucked her. Looking in her eyes as I pumped her slowly, I told her "You're a very dirty girl and I'm going to fuck you all weekend." "Yes," she whispered, barely able to get the word out of her mouth. I increased the tempo, pumping her faster and faster, holding her hips as she braced herself and pushed back into me. I was out of my mind with lust as I watched her in the mirror, changing the tempo and watching how she responded. She was moaning loudly and pleading almost incoherently, "Fuck me, baby. Fuck me. Fuck me." I continued a nice slowing fucking and she was gently rolling her head, tossing her hair to and fro. I asked, "Has your husband ever fucked your ass?" "No, he's way too big," she said. I asked "Is that so?" Leaning in to her, whispering near her ear "Do you want me to fuck your ass, dirty girl?" I asked. She submissively said, "You can do anything you want." Continuing the slow fucking, I wet my thumb and slid it into her ass, feeling my hard cock sliding in and out. Sliding my thumb in and out in cadence with my cock pistoning in and out of her, she started moaning louder and louder. "Well, I think my cock will fit nicely" I said, as withdrew from her pussy and pressed my cock against her ass. She moved her hips down a little, reorienting herself, and pooched out her ass some more, and then I started slowly feeding my hard cock into her warm asshole. She held herself still, pushing back as I fed every inch into her, holding her hips until I was buried inside. I held my cock in her, reached up and started gently kneading her swollen tits, and then started kissing her neck and shoulders. "Oh, Christ," she muttered as she started rotating her ass. Watching her, taking her hips in my hands, I began fucking her sweet ass at a nice slow and steady pace. She was moaning softly, and then she got louder as I change speeds and altered the tempo. Slowly pulling all the way out, then plunging back in. Jennifer's moans turned into grunts, and she braced herself against the wall as I fucked her ass urgently. She felt so damn good. Her ass was so warm and tight. Breathing very heavily, I felt that familiar tingling, then heard the moans coming from deep within me and erupted into her ass, buried deep as I emptied myself. Jennifer stayed pressed against me as her panting subsided and her breath came back to her. After pulling out of her, my cum began to oozing out of her ass. I scooped some up, leaned forward, brought my hand to her mouth, and whispered, "You're a dirty fucking girl. Eat my cum." She opened her mouth and engulfed my fingers, sucking and licking my thick load. She turned around, looked at me, and said, "That was incredible." We had enjoyed ourselves tremendously. And that was Thursday night of the company meeting, and we didn't depart until Sunday afternoon. Hooty hoot! What a weekend it was! This evening was the beginning of a very hot, long-standing affair with the sweetest and dirtiest woman I have known. I will add sequels about other times that Jennifer and I got together. I hope you enjoyed the story and please send me your feedback. My First Encounter With Maryann I first met Maryann at work. We knew and liked each other, and over a couple of years became very friendly. I was always intrigued by her, as it was obvious that she was a very assertive, domineering, and confidant woman. I had only met her husband a couple of times, but it was very apparent who wore the pants in that relationship. For me being a closet submissive to women, I was particularly fascinated by her. I would often playfully and somewhat jokingly flirt with her, and ask her when she was ready to run away with me. She would usually say that I wouldn't be able handle being her boy, and that I should just stick to fantasizing about her while I abuse myself. One time she left some paperwork on my desk for me to handle for her, but I didn't know what needed to be done with it. When she came to me later in the day and found the paperwork unfinished, she scolded me in such a way that it was sort of playful, but at the same time aggressive and a bit belittling. I told her I was sorry and that I would finish it up for her immediately. Then I jokingly said that she should probably spank me to make sure that I learned my lesson. She then sat on my desk and told me that I always say things like that, but that she seriously doubted if I was man enough to take a spanking from her. The tone in her voice was not playful; it was very serious and somewhat stern. She had a wicked smirk on her face as she turned and walked away. The way she had spoken to me made my cock painfully erect. In fact, my cock was actually throbbing so much that I thought I might ejaculate in my pants without even touching myself. A couple of weeks later she had a deck party at her house and asked me to come over. I was happy to be invited because I knew that her husband would be there, and I always loved to watch the way she bossed him around. I found her obvious dominance over him to be very arousing to witness. I was also curious to see if another guy that Maryann was friendly with would be at the party. His name was Gary, and he and Maryann would often meet up and go to lunch together. Rumors abound that they were having an affair, and it was actually difficult to imagine that they were not doing something naughty together. Gary was indeed at the party, and at one point Maryann had both Gary and her husband come in the house to help her with something. They disappeared for about twenty minutes, and when they came back the men were hauling a fresh cooler of beer. The appearance was that she needed the men to help get some more beer, but in actuality, that was just a cover. I later found out that Maryann's husband was a cuckold and that she brought the two men to her bedroom so that Gary could fuck her while her husband watched and everyone out on the deck was having a good time. This is something that I found out directly from Maryann later that evening. As the party began to wind down and people started leaving, Maryann asked me if I would stay and help her clean up. She also told me that she wanted to show me something. I happily agreed and I asked her what she wanted to show me. She playfully said that I would have to be a patient little boy and wait until later. I said ok and was very intrigued, but I really didn't think it would be anything of significance. By the end of the evening everyone had left except Maryann, her cousin Jennifer, her husband, and me. The four of us went to the living room, presumably to sit and chat, but then Jennifer said to Maryann something like, "Shit, I left it in the car". Maryann rolled her eyes then said to me and her husband, "Boys, Jennifer and I need to speak privately. Go stand outside on the deck until we are ready for you". Her husband immediately said yes ma'am, and I followed by saying it as well, but with a little bit of a smile on my face. Maryann did not return my little smile and just leered at me pointed her finger towards the deck. Her husband and I stood outside on the deck together and shared some uncomfortable chat and a lot of awkward silence; actually, just about ten minutes of silence. Then the lights on the deck flickered off and on, and her husband said that meant it was ok for us to go back inside. The way he said that, I had a bit of a moment of clarity and immediately thought that I was involved in something quite a bit out of the ordinary. Once back in the house, Jennifer got up and started walking toward the stairs. As she did she said, "Come on, Andy (Maryann's husband's name) and gently slapped her thigh a couple of times when she said it – pretty much the way someone would call a dog. Andy immediately followed Jennifer up the stairs without saying a word. Now I really knew something odd was brewing. Maryann walked me over to the sofa chair in the living room and simply pointed at the chair and said, "Sit, boy". I obeyed without a word; somewhat due to the fact that I was a little stunned and extremely aroused. Maryann explained to me that her husband and she had a legitimate D/s relationship, and that he was indeed her little bitch. She also told me that he was a cuckold, and explained that earlier in the day when she called Gary and Andy in to help her with something, that they actually went to the bedroom and Gary fucked her while her husband watched. Then she explained to me that earlier in the day Andy accidentally stepped on Jennifer's new pointy toed spike heels that had only been worn once. Although he did not scuff the shoes, he did need to be punished for his clumsiness. Maryann told me that she was going to give him a hard spanking while Jennifer watched. She also thought that it would be good to let me watch, because it would add to her husband's embarrassment, and that I would finally get to see what a spanking from her was like. She stood up and said, "Now, let's go have some fun upstairs". As she began to turn she did the same thing Jennifer did earlier, and slapped her thigh a couple of times and said "Come on boy". I silently followed her up the stairs. Part of me was very excited and part of me was nervous as all hell. Once in the bedroom, Maryann had me sit on a chair right beside the bed. Jennifer then walked Andy over to the bed. He was between where I was seated and the bed and he was facing the bed. Jennifer then leaned towards Andy and said in a very sexy voice, "Show time. Drop those pants". Andy obeyed and dropped his pants all the way down to his ankles. He was bare-assed, and Maryann told him to lay face down on the bed. Maryann looked at me while she folded a leather belt, and told me that this is what to expect when receiving discipline from her. She was not gentle or playful when she began to beat his ass; she delivered a serious ass-whipping. Her and Jennifer were laughing and having a good time though. When she was finished beating him, he was told to get up, and with his pants still down around his ankles, he was made to walk over to the other side of the room and stand in the corner like a bad little boy. Jennifer was laughing like a little schoolgirl and walked out of the room saying that she had to go pee. Maryann sat on the edge of the bed looked at me and asked me if I still thought that I was man enough to take a spanking from her. She said, "If you think you can handle it, I would gladly consider involving you in some of my future activities". I was very intimidated, but I told her that I thought that what she just dished out was more than just a spanking. Then I told her that I could still handle it. She said with laughter in her voice, "That's great... Stand up". I stood up and she snapped her finger and pointed to the spot on the floor in front of the bed where her husband was standing before. I walked over to the spot and she told me to drop my pants and underwear and assume the position on the bed. I did so and waited for her to begin while she paced behind me with her high heels clicking on the floor. Then she yelled to Jennifer and said, "Jennifer, get your ass back in here. The little boy thinks he's man enough to take it". Jennifer's heels clicked loudly on the hardwood floor as she scooted back to the bedroom. When she came back in the bedroom she said, "Wow! I can't believe he agreed. I really thought he was way too much of a pussy to take a good hard one". There was a brief pause between the ladies then they both started laughing and Maryann said, "Well, we haven't gotten quite that far yet". This was followed by more laughter and Jennifer saying, "He actually does look like a closet faggot. I bet he is no stranger to having things in his ass". I was red faced with humiliation and extremely aroused at the same time. Then I heard Maryann say, "On with the show". With that I received the first stinging blow to my ass with the belt. The pain was more than what I imagined it would be. Maryann was not fucking around; she beat my ass. All the while her and Jennifer laughed and talked, belittling me, and questioning my manhood. Jennifer kept saying that she really thought that I was a faggot. To which Maryann said, "That's ok, faggot cock suckers make great pets". When the beating ended, I found out what it was that Jennifer said she left in the car earlier. It was a digital video recorder. Jennifer had recorded the entire beating. I was humiliated and very frightened as to what the women would do with the recording. Maryann told me that I did very well and that she would be using me again real soon. She then told me to put on my pants and told me to scoot on home now, giving me one last slap on my sore ass as she said it. Jennifer was already looking at playback of the video in the view finder and giggling with genuine amusement that was bordering on glee. She said, "Bye faggot. Maybe next time we can get you something in that fairy ass of yours. Oh, and when you get home and spank that tiny little faggot cock of yours tonight, make sure that you eat your cum and think of me while your doing it". I was too overwhelmed with shame and humiliation to say anything back. I just left to the sounds of the two women laughing at me. When I got home, I did spank off to the events of the evening, and I did lick up my sperm while thinking of Jennifer. My First Encounter with Rachel The meeting broke up a lot earlier than I expected. I had about six hours to kill before my flight was to leave, so I decided to call my sister. We rarely had a chance to visit, because I never seemed to make it to Omaha except on business, so this evening would be a rare treat. And it would give me a chance to meet her new husband, Dan, and his daughter Rachel. I touched her number on my speed-dial and heard the pleasant "hello" on the other end. "Hey, Janine. It's Jeff. What's up?" "Nothing much, little brother. What's up with you?" "Well, I'm here in town, and I've got some time on my hands for a change. How would you and Dan and Rachel like to go somewhere for dinner? My treat." She gave it a bit of thought, then said, "Sounds good, but Dan and I have an appointment with the tax attorney at 4. We'll be back a little after 6. Does that give us enough time?" It would. My flight wouldn't leave until 10:15. "That'll work," I replied. "Great. Why don't you come on over and catch some rest while you're waiting on us?" That was a welcome invitation. Much better than sitting around in a hotel bar for 3 hours. "Thanks, sis. I'll be right over. See ya." I hopped into the rent car and headed her way. I arrived at Janine's house, and got out of my car just as another car, full of school kids, was pulling up to the curb. A slender girl got out and headed toward Janine's front door. She was about five-foot-two, and wore a short, pleated skirt, black shoes with the clunky heels the kids love these days, and a baggy pullover sweater. Long, strawberry-blonde hair tumbled down her back, well past her shoulders, and she carried an armload of books and a small purse slung over her shoulder. She looked to be about sixteen years old, which seemed strange to me, since I knew Janine had said that Rachel had turned eighteen two months ago. The front door swung open and Janine stepped out to greet us both. "Perfect timing, you two! Rachel, this is my brother Jeff. Jeff, our daughter Rachel." From under the armload of books, Rachel extended a small, delicate hand. "Hi, Uncle Jeff. Pleased to meet ya." I took her hand, and she squeezed my fingers and held on for only a second or two more than social custom required. This gave me the opportunity to check her out more closely. Rachel had a clear, peaches-and-cream complexion, glittering hazel eyes, and a cute dimple in her chin. Her quick, sly, mischievous, almost conspiratorial grin almost shouted out "naughty girl" and intimated that she was more worldly-wise than her age would suggest. She flashed it at me before quickly turning away. "I'm gonna run upstairs and change," she called to Janine as she headed toward the stairs. "Don't run off to anywhere," Janine countered. "We're all going out to eat tonight." "Cool," replied the little lady as she disappeared. Janine turned her attention to me. "Okay, Jeff, I'm off to meet Dan at the attorney's. Make yourself at home. If you want to watch TV, the remote's on the table by the easy chair. See you a little after six." And with that, she grabbed her purse and rushed out the front door. I didn't feel like watching TV. There was nothing good on at 3:30, anyway. So I picked up the morning paper from the coffee table, settled into the easy chair, and started scanning the headlines. * * * After about half an hour Rachel came back into the room, carrying a towel. She tossed the towel across the back of the sofa, and flopped herself down on the sofa cushions. She had changed out of her school clothes, and was now barefooted and wearing a skimpy athletic short set. It consisted of a pair of hip-hugging low cut shorts and a bikini-style top which was little different from an athletic bra. Stretching out on the couch, she lay on her back with her hands behind her head and stared absentmindedly at the ceiling. As the minutes passed, it became harder and harder for me to avoid inspecting Rachel over the top of my newspaper. She was more than a little on the skinny side, and startlingly prepubescent for an eighteen-year-old woman. A real late-bloomer, to be sure. Her arms and legs were long and slender, but athletic, and there wasn't an ounce of fat anywhere on her bare midriff. There was nothing of substance under the athletic bra; her chest was flat as a pancake. But, whether deliberately or not, she was displaying to me two of the most beautifully sculpted armpits that I had ever seen. And there was something else about Rachel that I found captivating, though it took more than a few stealthy glances at her from behind my paper before I figured out what that was. Her ivory-white skin was perfect. Neither blemish, freckle, nor birthmark, nor the slightest trace of body hair was visible anywhere on her body. As I came to that realization, I found myself wanting to touch her all over, to lick every square inch of that perfect skin I could see, starting with those luscious pits. I knew it was wrong. I knew that she was almost jailbait, that she was my big sister's stepdaughter, that she was almost 20 years younger than me. I knew all that. But I just couldn't keep my eyes off her. After a little while Rachel glanced in my direction, and though I averted my own eyes as quickly as I could, I knew I was busted. But she pretended not to notice that I had been staring at her. The faintest trace of a smile flickered across her lips as she arched her back slightly and stretched herself. This allowed the athletic bra to ride a little higher up her torso and exposed the lower half of her rib cage to my view. I tried my hardest not to be obvious, but I couldn't keep my eyes off her, nor could I shake off the suspicion that she was teasing me. As I tried to put that idea out of my mind, the girl abruptly sat up on the sofa and broke the silence. "Hey Jeff, I'm bored. Janine and my dad won't be home for a couple of hours. Ya wanna play with me?" Grateful to dispel the growing tension in my mind, I folded my paper and replied, "Sure, why not? What've you got?" I thought she was talking about a video game or something, so I wasn't ready for the answer I got. "Tickle me." All I could think to say was "huh?", and I had barely gotten that out when she jumped off the couch, ran across the room and flopped into my lap. She flung both arms up above her head, exposing her gorgeous, hairless armpits just inches from my face, and said it again. "C'mon. Tickle me. I'm real ticklish." This was either too good to be true or a disaster about to happen, but at the moment I didn't care which. With only the slightest hesitation, I ran my index fingers up and down her sides. She giggled and squirmed in my lap, and I suddenly realized that I was becoming thoroughly aroused. And there was no way that Rachel couldn't have noticed it, either. Abandoning all caution, I galloped my fingers harder and faster up and down her rib cage, as she howled and shrieked with laughter. She gripped her left wrist tightly with her right hand, forcing herself to keep her arms high over her head. "Higher!" she squealed. "Get my underarms!" I reached around her back with my left hand and pulled her close, and holding her left elbow high overhead with my right hand, I brushed her armpit up and down, again and again, with my mustache. By now she was laughing so hard that tears rolled down her cheeks. I pushed her out of my lap and stood up, grabbing both her arms at the elbows and lifting her off her feet. Since she couldn't have weighed more than 90 pounds, and my adrenaline was pumping overtime, I lifted her with ease. Moving from left to right, and back again, I worked her armpits over mercilessly with mustache, lips, and tongue. She thrashed about wildly, screaming and laughing convulsively as she struggled in vain against my firm grip on her arms. "Time out!", she finally gasped. She was out of breath almost to the point of fainting, so I carried her across the room and gently lowered her onto the sofa. It didn't take the girl long to catch her breath. I stood above her as she lay on the couch, motionless but for the heaving of her chest, my eyes fixed on those adorable armpits which I had just so thoroughly enjoyed. At last she spoke. "You like me, don't you? You like me a lot. I could tell when I was sitting on your lap." I nodded. Stevie Wonder himself could have seen the bulge in my pants which confirmed that I still liked her a lot. There was no sense trying to hide it, so I tried to be nonchalant about it. "You're a real pretty girl, Rachel." That was the best I could come up with. It's hard to be debonair when you're as horny as a hog. She quickly sat up, grabbed my hand, and pulled me down beside her. "Let's play some more," she said, almost in a whisper, an obvious note of excitement in her voice. I was more than willing, but what I wanted to do more than anything else was to go to the bathroom and jerk off. "Are you sure you're up to it?" I asked. Once again, I wasn't ready for the answer I got. "Yeah, but let's do something else. You wanna take off my top?" Without waiting for an answer, she turned toward me and raised her arms straight over her head, expectantly. To do anything else would have been inconceivable. My heart pounded and my hands trembled as I caressed the sides of her abdomen, hooked my thumbs under the elasticized lower hem of the athletic bra, and slowly moved my hands upward. My palms felt the ribs under the smooth, soft skin. My thumbs slowly explored the hollows of her armpits before tracing their path upward along the inner surface of her biceps. Rachel closed her eyes, bit her lower lip, and moaned softly as my thumbs departed from her pits. My palms and fingers caressed her shoulders, pulling the bra over her head, past her elbows and then her wrists, and finally to the floor beside us. Time almost stood still. My eyes devoured the little angel as she slowly fell backward into a supine position on the couch, arms flung overhead in an attitude of complete surrender, and her feet swung up from the floor and over into my lap. I could hardly keep myself from ejaculating right then and there. My eyes feasted themselves on her breasts, or rather, on the areas where breasts would normally be on a woman her age. In Rachel's case, they were tiny pink nipples which happened to be hard as a rock. Clearly, Rachel enjoyed displaying herself to me. She kept her gaze fixed on me for what seemed like half an hour, as my eyes ravished her. I wanted so badly to pinch the tiny buds on her chest. I craved the silky-smooth skin under her arms. I wanted, no I needed, to kiss her, to stroke her, to nibble her, to suck on her, forever and ever without stopping. My blood pressure must have been in the stratosphere, and I felt like I was about to pass out. Rachel slowly, sensuously shifted position on the sofa, and the sly smile on her face made it clear that she knew I was turned on and that she loved it. Finally, in the husky, whispery voice I had so quickly learned to adore, she ordered, "Now the shorts." "Huh?" It was like I had just awakened from a drunken stupor. "Now the shorts. Take off my shorts, Jeff. Please." This last word had a bit of a begging ring to it which drove me wild. Without a word, I grabbed the waistband of her shorts and quickly pulled them off, and she immediately swung her right leg up over my head and behind my back, so that I found myself sitting between her knees. I turned sideways on the sofa, so I was facing her directly, and confronted the most awesome sight I have ever beheld, before or since. I now knew empirically what I had known intuitively all along. There was not the slightest hint of blemish or flaw anywhere on Rachel's body. The sweet spot between her slender legs was devoid of pubic hair, and her thighs were spread apart enough to reveal the recent onset of early-stage pubescence. The lips of her womb were bright pink and slightly swollen, with tiny beads of moisture beginning to collect around her opening, and I knew that she was every bit as turned on as I was. For another eternity I gazed at her naked body. Her perfect skin. Her smooth, flat belly. Her tiny little pink nipples, perfect little cones like Hershey's Kisses, so hard that you could scratch glass with either one of them. And her soft, smooth underarms, so sweet to the taste, on which the tip of my tongue or the brush of my lip sent her into such shuddering paroxysms of hysterical laughter...hypnotized me. So deep was my reverie as I stared at her, that I almost didn't hear Rachel's next command. "Finger me." I could only stare into her eyes, as in a trance, so she said it again, more urgently. "Finger me. Stick your finger inside me. I need to come now. Please. Make me come. We don't have much time." Those last words snapped me out of my trance in a hell of a hurry. She was right. Janine and Dan had said they'd be home a little after six, and it was now five fifteen. Time flies when you're having fun, and we'd sure been having lots of fun. But now it was time to bring this thing to a climax, so to speak, and once again I was all business. "I have a better idea," I said, in my own husky, quivering voice. Without another word, I slid my hands under Rachel's buttocks, lifted her bottom slightly, and buried my face between her thighs. I felt her shudder and heard her moan with delight as my tongue drilled through her beautiful pink defenses and began to explore her inner treasures. My tongue fluttered and lapped as I satisfied my thirst for her precious fluids, which now flowed so freely that I had to seal my lips around hers to prevent the escape of a single drop. The girl's body quivered and stiffened, her back arching as she strained against me, and a series of long, low moans escaped from her throat, betraying the deepening intensity of her pleasure. My tongue abandoned its circular exploratory mission and worked its way upward, located her tiny, pearl-hard clit, and began to besiege it relentlessly. Rachel's body shuddered and writhed as she screamed out an invocation, begging me for more, and her hands intermittently clawed at the sofa cushions and pressed against the back of my head. She was coming now, over and over and over, wave after wave of shuddering, shattering orgasms propelling her body into uncontrollable spasms of total release, as her vagina gushed its nectar into my mouth. With a long, catlike squeal and a final invocation of the Deity, her body made one last bone-rattling convulsion and went limp. She lay there for several minutes, her chest heaving as she caught her breath, while I dabbed the last of her bodily fluids from between her legs, taking care not to spoil the sofa cushions. Tears ran slowly down her cheeks as she regarded me adoringly, thankfully. "That was so good...sooo good..." she murmured. She had been brought into a state of utter release, complete and total ecstasy, but I still had a problem. A real hard problem, right there between my legs, and it was driving me crazy. "Rachel...I need you...I really need you...right now..." I begged her. A funny look crossed her face. I couldn't tell whether it was fear, or indifference, alarm, or what --- but I knew I didn't like it at all. She finally replied, and as was usually the case with Rachel, I wasn't ready for the answer I got. "Please, no. Please don't fuck me. I'm not on the pill, and Daddy would kill me if I got knocked up. But you can fuck my underarm if you want to. I know you love my underarms." With that, she rolled over slightly on her right side and raised her left elbow above her head, offering her smooth, creamy-white armpit for my satisfaction. I didn't need to be told twice. With trembling fingers I quickly got my belt unbuckled, and let my trousers and my boxers drop to my ankles. My cock had swollen to a size I had never before seen it achieve, and was so hard you could have broken it with a stick. Dropping to my knees on the carpet in front of the sofa, I found that my cock was perfectly aligned with Rachel's left armpit, which was stretched out wide and invitingly before me. Quivering in anticipation, I slipped the head of my cock into the satiny-smooth hollow of her pit. "Mmmm, yeah, that's right," she cooed, as she slowly and gently lowered her elbow until the first three inches of my meat was trapped in the caress of her soft skin. "Go ahead, man," Rachel urged me on. "Use me. Yeah. Ohhh, yeah. Use my pit." Slowly, rhythmically, I began thrusting my throbbing member back and forth into her armpit. To my delight, she responded by slowly moving her elbow forward and backward, caressing the rest of my phallus with the upper part of her inner bicep. The sensation of her pit skin on my dick was indescribable. I wanted it to last forever, but I had been overstimulated for quite a while now and I knew I was about to lose it. I clenched my teeth and concentrated, trying to delay my orgasm as long as possible. Rachel sensed that I was fast approaching my climax, so she readied the towel in her right hand to keep me from drenching the sofa cushions. "Go ahead," she whispered. "Come. Come all over me. Give it to me. Please..." And then it happened. As soon as I heard that last word, I started losing my load. Shaking like a leaf in a windstorm, two, three, four, five, six times I shot my hot seed into her underarm, and she giggled as she wiped up the mess with the towel. Obviously, she was much enjoying the tender torture she was inflicting on me. With the long, low groan of a dying man, I squirted my last droplets and collapsed backward onto the carpeted floor. How long I lay there, with the room spinning around my head, I don't remember. * * * A car door slammed in the driveway, immediately followed by another car door slamming. Rachel's eyes widened. "Fire drill!" she whispered urgently, as she grabbed her shorts, her bra, and the towel and sprinted for the staircase. I leaped to my feet and hauled up my boxers and trousers. I had just gotten my belt buckled and settled back into the easy chair when the front door swung open.