3 comments/ 143347 views/ 10 favorites A Natural Sissy Ch. 02 By: harv069 Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments from readers justify it. A Natural Sissy Ch. 02 – The party Just before we reached the entrance, which was manned by a doorman, I said, "Now remember, Stacy, you just do what I tell you, and everything will be fine." "Ok... okay." His nervousness was showing, but that was to be expected. He had no idea what was going to meet him on the other side of the door. As we entered the ballroom where the party was already underway, we were swarmed by a group of my friends, some who already had met Stacy, and some who hadn't. We exchanged the normal greetings, and most of the girls who had met Stacy before gave him a hug and showered him with kisses and then two of them sandwiched him between them and led him into the large room, filled with people. I followed along, allowing my two friends with Stacy lead the way. They took him around the room introducing him as Stacy, Gail's new boy toi. Everyone welcomed him, some kissing his cheek, and a few with hot, sensual kisses on his lips. I noticed how he blushed at the reception he was getting. Such a sweet, innocent sissy. Someone had thought to bring us drinks from the free bar, and I took Stacy from his escorts and led him to the patio just outside the ballroom. "Take these with a sip of your drink, Stacy." I handed him the Viagra and the GHB. He downed them both without argument. The lighting outside was subdued, in contrast to the brilliant lighting inside. I steered Stacy over to one of my male friends, Ralph, and introduced Stacy to him. "Stacy, this is my very dear friend Ralph. Suck his cock." Very dear friend indeed. We met once a week for a marathon fuck. "Wh... what?" replied Stacy, in a tone that showed displeasure. "What part of 'suck his cock' do you not understand, Stacy?" "I can't do that! I don't like men, I like girls. I wont do it." "Yes, you can do it. And you will. I told you to do what I said and everything would be fine. Would you rather that Ralph use you as a punching bag?" I watched Stacy size Ralph up, and I knew he wouldn't want to cross a heavyweight wrestler like Ralph. "Don't let him hit me, Gail. Please." "Then I guess that settles it. Suck his cock. And beg him to let you do it, since you're being such an ass about it." Stacy looked back and forth at Ralph and me. Ralph had a slight grin of amusement on his face. Then he turned to Ralph, and said, "Ralph, may I... may I ... suck your cock?" The GHB has started to work on Stacy's inhibitions. "Sure, sweetie. Just kneel down on this cushion so your stockings won't run, and take my cock out for me." Ralph had, of course, been briefed that this was going to happen, and he threw a cushion from one of the nearby lounge chairs on the floor. Stacy hesitated a moment, then knelt on the cushion and reached for Ralph's zipper. He pulled it down slowly, trying to delay the inevitable, but soon had no option but to fish the large, growing cock from within. He stared at it as it grew, trying to determine how to approach the situation. "Stacy, this is easy. Just suck it like you do my strapon when I fuck you. Lick it all up and down to get it wet like you've learned to do, and then take the head in your mouth and go from there." Stacy finally took the cockhead in his mouth and started swirling his tongue around it, getting it wet, and then took more of the shaft in, and began moving his head up and down, stroking the shaft not in his mouth in rhythm with his head movement. Ralph put a hand on either side of Stacy's head and began slowly fucking my boi toi's mouth. It looked like Stacy was getting excited, and started really enjoying the job he was doing. A small crowd began to form, watching Stacy's initiation to blowing a real cock. There were softly spoken words between those watching, and even a few bets on how long before Ralph would fuck him in his boi pussy. I had to smile at that, because that was next on my planned agenda, with Ralph's agreement. It wasn't long coming. Ralph was getting turned on, and he pulled his cock from Stacy's mouth and said, "Stacy, get over there and lean over the back of that lounge chair. I'm gonna fuck your ass now." Stacy looked up in horror, and tears began to form at the corners of his wide eyes. "Please don't. You'll hurt me. I don't want to get hurt." I spoke up then, "Stacy, honey, Ralph isn't going to hurt you. He's just going to do what I've been doing with my strapon, except he'll be using the real thing. You'll love it." "No, I won't," cried Stacy. "I don't like men. I like girls. I didn't try to stop you, 'cause I love you, but I don't love any man." I took Stacy in my arms and hugged him tightly, moving his to the lounge chair. I took his hard cock in my hand and said, "Stacy, you need to do this. It's in the training manual for sissies. It's what they do, and you know you're a sissy, so you have to do it. How about if I give you a nice handjob while Ralph fucks you?" Stacy wiped away the tears, and said, "Only if you won't let him hurt me, Gail. I'm afraid." "I promise you I won't let Ralph hurt you, sweetie. Now bend over the back of the chair like a good sissy." I started stroking his cock as I pushed him over the chair. Ralph took over and started pushing his cock into the rosebud, and slowly worked just the head inside. Then he waited, giving Stacy time to calm down and adjust to the presence in his ass. After a moment or two he started pushing in deeper and deeper, waiting after each lunge, until he was fully buried in Stacy's ass. Then he started in earnest, fucking my boi's ass faster and faster until Stacy squealed with delight. Ralph continued until Stacy was almost in ecstasy, and then he erupted, filling Stacy's ass with cum until his cock began to go flaccid. This part of the initiation came to a close as money passed hands among the bettors. I pulled Stacy to his feet and praised him for a job well done. "That was wonderful, Stacy. You did a great job there. I'm going to give you a big reward when we get home." Stacy's eyes widened, and he broke into a wide grin. :"I did good?" "Yes you did, sweetheart. You did a wonderful job." I took his head in my hands and planted a long, hard, sloppy kiss on his mouth. "Now I want you to go with Wanda and Shirley and get cleaned up a little. Your hair is a mess, your lipstick and mascara are ruined, and your cock spilled cum all over, and I'm not even going to make you lick it up like I usually do." Now git." I slapped him on his ass and pushed him into Wanda's arms. As Wanda and Shirley guided him into the ballroom and toward the ladies room, I heard his quietly saying to the two girls, "Gail said I did good, and I'm going to get a reward when we get home," his voice filled with pride. The girls smiled sweetly in response. Wendy attended to getting Stacy's face back in order, applying slutty makeup to the extreme. Stacy looked like a whore. Shirley had spent the time toying with Stacy's cock and balls, keeping his cock rock hard. A few minutes later, everyone was back inside when Stacy returned to my side, looking very much refreshed, his hard cock tenting the short skirt he wore. "Oh, there you are Stacy. I've been waiting for you. We're going to play a game now, and you'll be a prize for the winner. I pulled his skirt hem up exposing his cock and started pumping it slowly to keep him from thinking too much about what I had just told him. "Okay, Gail," he smiled broadly. "What do I have to do?" "Whatever the winner of the game wants you to do. It won't be hard." I led him by his cock, to the amusement of all who had gathered, and took him behind a portable folding partition. There was a bed and a chair there. "Just sit in the chair and wait. The winner will be here very soon." I left him sitting in the chair and went back to the other side of the partition. There would be no game. Only a lot of laughing and shouting to simulate that a game was in progress. I placed numbers in a hat, and everyone drew one. Whoever got number one would go first, and so on. The first "winner" was a girl named Roberta. She went behind the partition, and a silence fell on the crowd. They all wanted to hear what was happening behind the partition. Oral sex. Pure and simple. She blew him, and he sucked her off. Numbers two, three and four followed every twenty minutes with similar results. Then the façade of a game evaporated and people just lined up in plain view of Stacy. They took their turn as they became first in line, sometimes one on one with Stacy, sometimes a gangbang. Poor Stacy's mouth and ass took a real beating, but he was enjoying every minute of it. Every once in a while I took him another drink to wash down the cum accumulated in his mouth. Then it was over. The last of the group had finished playing with my boi toy, and everyone started drifting out to go somewhere else, most just to go home. I led Stacy outside in the usual manner, by his cock, and handed the valet the keys to Stacy's Mercedes. On the way home I couldn't have gotten a word in edgewise. Stacy jabbered continuously about how much he enjoyed the party, and when could we have another? The next chapter will begin with Stacy's promised "reward." A Natural Sissy Ch. 03 Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments from readers justify it. Chapter 03. The Reward Once we were at home, I still couldn't keep Stacy quiet. "When do I get my reward, Mistress Gail?" repeated every other breath. Constantly. Finally, after I had changed into my bedtime attire (a pair of 4-inch heeled mules, and a see-through short nylon robe, in pink, like my mules) and Stacy had stripped naked, wearing only a cock and ball harness, as was my requirement when I had nothing else in mind for him to wear, I gave in to his endless pleas. "Okay, Stacy. I've been thinking of what I could give you for a reward. I've decided on your very favorite activity. How would you like to show me just how much you love me?" "Oh, yes, Mistress Gail. That would be wonderful. Please let me show you." "You remember how to do it, Stacy?" "Oh, yes. I could never forget that." As I settled back into my recliner, I said, "Okay, Stacy. You may begin." It was a ritual that I had taught him months earlier, but had not recently allowed it. I lit a cigarette and flipped on the CD player with some soft mood music. Stacy tripped all over himself as he turned down the lights and lit several candles stationed around the room. Then, his Viagra induced hard cock preceding him, he placed a TV tray next to my recliner, and put a iced wine cooler beside it with a bottle of very expensive vintage wine (at his expense, of course) He poured a wine glass ¾ full and set it on the TV tray along with a penis whip and a riding crop. Done with the preliminaries, he knelt at my feet and lifted my right foot, removed the mule lovingly, and started the ritual. He sucked each toe, beginning with the smallest, and as he moved from one to the next he kept repeating his mantra, "I love Mistress Gail. I love my Mistress Gail." He stayed at each toe until I signaled for him to go to the next by tapping his shoulder lightly with the riding crop. At the three-tap signal, he moved to the other foot and the routine continued. I allowed this foot worship to continue for almost an hour. Then a duo of three taps signaled Stacy to go to my pussy. He gently spread my legs allowing room for his head between them, and began a worship ritual there that I allowed to continue until I had my seventh orgasm at the ministrations of his lips and tongue. A very hard slap on his shoulder with the crop told him to cease and rise, standing with his fingers interlocked behind him, his hard cock pulsing rapidly. "Are you ready to fuck your Mistress?" "Please, if it be you will. Mistress." I replaced the crop with the penis whip and began slapping his cock unmercifully with it until I saw the tears in his eyes. "You have done well, sissy Stacy. You may fuck your Mistress now." Without a word he knelt again, straddling my left leg. He placed his left hand at my pussy and began ministering to it very slowly as he humped my leg, rubbing his hard cock against the soft flesh of my calf. "Not too fast, Stacy, dear. There's no need to rush. We have until morning, and it's only three am." "Yes, ma'am." He slowed his pace, and slowly worked back to a steady rhythm. His mantra continued as he muttered "So good, so good, so good..." After an hour and a half, I asked, "Do you want to cum, sissy?" "Please, Mistress Gail. I need to cum so badly." "Then you may." He sprayed my leg with cum immediately, spilling some onto the carpet below. But he was quick. He bent down and lapped it up before I could scold him. Then, without command, he licked my leg clean. "Would you like to do that again, Stacy?" Ritual, you know. "Please, Mistress, may I fuck you again?" "You have been a good sissy, so yes, you may fuck your Mistress again. But not the same leg. That one is satiated. Do you need my assistance in getting your cock hard again?" A stupid question, as it had not gone a bit flaccid, but still, ritual took precedence. "Please, Mistress, help my cock get hard again." He stood between my legs, waiting, hard cock within a foot of my mouth. This was his real reward. I leaned forward and took his cock into my soft, moist mouth. I teased it the way I knew he loved, then took it all, even into and past my gag reflex, and deepthroated it. When I heard him say, "Oh, my." I released it from my mouth and smiled sweetly at him. "I think you're ready now, Stacy. We repeated the entire scene again with the toe sucking, followed by his humping my other leg until he came again, with results not unlike the first time. Cum on my leg, cum on the carpet, cum almost everywhere. When he had cleaned every drop away with his tongue, I stood, and as I walked toward the bedroom, I said, "I'll take my breakfast in bed this morning, Stacy. Bring yours as well, and we'll share a breakfast together as we sometimes do." He knew what that meant. He would bring mine on a lap tray, and his in a dog bowl, which he would consume on all fours beside my bed, lapping at it with only his mouth and tongue. After breakfast, I went to sleep. Stacy had chores to do, so his sleep was delayed until the afternoon, after I inspected his work, and dry humped his ass for every error he made, real or not. The poor man was exhausted when I finished my final humping of his as and sent him to his pallet on the floor beside my bed. I let him sleep, fixing dinner myself. Even a dish for him, which I left in the fridge for when he woke. When he did wake, and as he was eating his dinner (at the table, since I was feeling generous) I sat across from him drinking a scotch on the rocks. "Stacy, I've been meaning to talk with you about moving forward in our relationship. What do you think about getting you some permanent tits?" He spit the food in his mouth onto the table. "Wha... what?" "Breast implants, dear. I think that's what we need to do next, so you can advance to the status of a girlfriend. You do want to be my special girlfriend, don't you?" "Ye...yes, ma'am, I do. But... but breast implants?" "Of course, Stacy. All my girlfriends have beautiful tits. Don't you agree?" "Yes, they do," He admitted. "And you just said you wanted to be my special girlfriend. I heard you very plainly. So shouldn't you have pretty tits, too?" "I don't know..." "Well, if you just want to continue to be my sissy, just say so." My tone was harsh. "No. No, I do want to be your special girlfriend, Mistress Gail. But... tits?" "Well, yes. Duh." "Can I think about it?" "Sure, sweetie. I don't need an answer until bedtime. Oh, just think, Stacy, when you're my special girlfriend, you can sleep next to me on my bed every night. We can do girl things together all the time. Won't that be fun?" "I can sleep with you? On your bed, every night? And you won't treat me like a sissy anymore?" "Yes, Stacy. On my bed, every night, except when I have one of my men friends over. And you won't be my sissy anymore." The last part of that was an outright lie, but we do what we need to do, don't we? "Then... then, okay. I'll get some tits, Mistress Gail." "Wonderful! I'll call my surgeon friend, Abigail, tonight and set up the procedure. I'm so thrilled that you want to be my special girlfriend, Stacy. I could just eat you up." I rose and circled the table, leaned over and kissed my sissy smack on the mouth, probing his with my tongue. The rest of the day was unremarkable, except that I noticed an array of emotions ripple through my sissy as he contemplated his fate. Forty-something year old sissies can have the cutest smiles and the most awful frowns. And the looks of concern alternately opposed to the looks of delight amused me no end. I swear I could see the wheels turning in his sissy little head. * My, my, dear readers, what's happening here? Will Stacy actually go through with this new development? And what, exactly, does Gail have up her sleeve? Stay tuned for the next episode. A Natural Sissy Ch. 04 Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments from readers justify it. Chapter 04. The Next Day I was up early, and called to set up a surgery for Stacy’s breast enhancement. The hormones were working but his tits seemed to have stopped growing at a B cup. I wanted him really top heavy. At least a D cup, maybe a DD. I let the exhausted sissy sleep. As I was finishing up my third coffee after breakfast, Stacy entered the kitchen, dressed to the nines as a very pretty lady. But this was Friday, and he should have been dressed as a sissy. Stacy said as he walked in, “Good morn…” I faked rage, saying, “What the fuck do you think you’re doing, sissy? This is Friday, damn it.” His face went pale with fear as he stood just inside the dining room, balanced on his five-inch high-heeled pumps. “It’s… its Fri… Friday?” he stammered. “Fucking right it’s Friday. You have earned some serious correction, you stupid ass,” I bellowed, suppressing my glee at catching him in error. “Now, you have 30 minutes to correct the situation, and then go to the rec room and lie face up on the pool table. Go!” *** Stacy hastily ran to the bedroom to redress. He stripped the makeup from his face, disrobed, slinging his feminine attire across the room, some landing on the bed, the rest on the floor. He carefully placed the expensive blonde wig on its form, and began digging out some of his sissy attire. Fishnet crotch-less pantyhose in off-black, low heel open toe patent pumps, and an off-black training bra with the cups cut out. He had to search for the ball spreader, but finally found it in one of Gail’s drawers. As he began to attach his gaudy imitation gold dangling earrings, those that almost grazed his shoulders, he discovered that he was still wearing his precious 2ct. diamond studs, and hastily removed them. Then he noticed that his fingernails and toenails were all wrong for a sissy. They had to be pale pink, not the ruby red he had on. He quickly removed the offending color and replaced it with pale pink. He matched that with the same shade of lip-gloss, followed by just a hint of rouge on his cheeks. Matching rouge on the nipples peeking through the cupless bra. Then just a light application of mascara, hardly noticeable to the untrained eye. But he knew Gail’s eyes were trained, and heaven forbid she find anything else to criticize. He was already in enough trouble as it was. Before he donned his pumps, he pulled on a pair of fancy ladies socks with a red bow in the back. “Garish,” he thought, “but I do what I must to please Gail.” He was finished in just under the 30 minutes allotted, and he was wearing all he was allowed unless he was going outside, when he could wear unisex slacks (no front zipper), and a see through white shirt that buttoned like a blouse (which is what it was). On his way out he stopped briefly in the bathroom and swallowed two Viagra pills. *** I was waiting for Stacy in the rec room, and he made it just in time to meet the 30-minute time allotted. He climbed onto the pool table, assuming a prone position, face up, legs spread just as he was supposed to do. I had already set up the IV, with the saline in place. I was fooling with the tubing when Stacy came in, more to call his attention to the apparatus that anything necessary for the procedure I was about to administer. He was as nervous as a cornered rat. Perspiration began to form all over his scantily clad body. Good. Just the reaction I hoped for. “Stacy, you know I have to punish you when you make mistakes as serious as the one you made a few minutes ago, don’t you?” “Yes, ma’am.” This is going to hurt me as much as it will you, because you have violated our agreement. You know that, don’t you?” “Yes, ma’am. Wha… wha… what are you going to do?” “It’s just something to remind you not to screw up again. I’m going to inflate your ball sac with saline. It won’t cause any damage, and your body will eventually absorb the saline and the inflation will recede to normal. But until it does the inflation will remind you of your grave error this morning. Are you ready?” “How… how long will that take? To get back to normal, I mean?” “I’m not sure. Probably a few hours, at least. Let’s get on with it.” I inserted a needle into his ball sac attached the feed tube, and started the IV at full flow. He would take the entire liter of saline. I sat at his side while the IV emptied, wiping his brow as sweat poured from it. His eyes tired up a few times, and I wiped away the tears, all the while praising him for taking his punishment like a real sissy should, speaking like a mother to a small child. I even stroked his hard cock a few times here and there during the drip. When the IV was empty, his ball sac had swollen to a size approximating a large cantaloupe. I removed the needle, and then lifted his balls to test the weight and it was about the same as the liter that had been injected. Just one more thing to do, and then I can send Stacy up to get lunch ready. I inserted a stainless steel rod into his urethra until only the tip remained showing. The rod was just under nine inches long and about 1/8th inch in diameter, so it was a near perfect fit in his cock. The tip left showing had a place to attach two delicate gold chains, the other end of each to be connected to a nipple clamp and fitted to Stacy’s rouged nipples. This would hold the cock up, away from the swollen ball sac, so the enlarged sac would be entirely visible. “Okay, Stacy, you may go and prepare lunch for us. We’ll take it on the patio in an hour.” I got up and walked away leaving him to deal with the swollen balls. I planned to grab a bottle of champagne and some cheese and crackers to pass the time until lunch on the patio. I watched Stacy try to walk with his ball sac so filled with saline that he could hardly manage to take a step without causing the sac to wobble back and forth with each stride. I laughed to myself at the sissy’s consternation. Stacy brought the lunch to the patio about five minutes before the hour was up. Mine on a serving tray, his in a dog bowl. “Oh, Stacy, dear, I forgot. You can eat at the table with me for lunch. Go get a real lunch and join me at table.” His eyes lit up like light bulbs, as he turned to return to get himself a real lunch. When he returned, we ate together like the best of friends, chatting about this and that until the meal was finished. Just as Stacy finished cleaning up after lunch the doorbell sounded. “Stacy, get the door, please.” “Dressed like this, Gail?” “Certainly, like that. You are appropriately dressed for sissy day, and whoever is at the door is probably just one of my friends. And they all know about you. Now go.” A moment later, I heard Ralph let out a boisterous laugh that rocked the house. I knew it would be Ralph, and I knew he would do what he could to belittle my sissy. I tuned in to the conversation at the door. “Well, hello, there, Stacy, my man. How the hell are you? And what happened to your balls? They look pretty swollen. Nice gold chains you have there, too. Are they real gold?” Ralph casually slapped Stacy’s balls a couple of times just for the hell of it. Stacy cringed at the slaps and ignored the question about the gold chains. “I… I … screwed up this morning, and Gail inflated my sac with saline.” Another boisterous laugh from Ralph as he pushed past Stacy and entered the living room where I was waiting. He swept me up in his arms and headed for the bedroom just as our script required. He looked back over his shoulder as I was giggling and squirming in his arms, and said, “Come on Stacy. I’m gonna show you how a real man fucks a pretty lady. I might even let you help.” “…let you help” registered in Stacy’s mind as a good thing. He eagerly followed Ralph to the bedroom and watched as I was unceremoniously dumped on the bed. Then Ralph said, “Okay, Stacy, you can get Gail naked while I strip off.” Dutifully, Stacy started removing Gail’s clothes until she was down to stockings and shoes. “That’s far enough, Stacy. I like my women to wear stockings and heels when I’m fucking them. But I seem to have a problem here. Do you see what it is?” Stacy glanced at Ralph, seeing that he was totally nude, but didn’t see anything wrong. “No, I don’t see a problem, Ralph.” “Well, Stacy, do you think I can fuck Gail with a limp cock?” “Oh. No, I guess not.” “Then what do we need to do to get it hard, Stacy?” “Well… I usually stroke mine.” “Nah, that won’t work for me. What else might get it hard?” “Maybe you could get Gail to suck it?” I broke in at that. “I’m not doing that. That thing would choke a horse.” Ralph feigned a confused look. “Well, I guess that’s out. She doesn’t want to suck me. What can we do now, Stacy?” “I… I… don’t know.” “Well, if you want to watch me fuck Gail, you need to think of something.” I could see the wheels ever so slowly turning in Stacy’s head, and he frowned. “Uh… I guess I could do it for you.” Ralph almost shouted, “Yes. That’s it. Now why didn’t I think of that? Get to it Stacy. Hurry. Times a wasting.” Poor Stacy was trapped. Now he had to get Ralph’s cock hard with a blowjob. Ralph sat on the edge of the bed and motioned Stacy over. “Okay, sport, kneel down here and get started. If you do it right, I’ll let you help me stick it to her.” Stacy took that to mean that he and Ralph would double fuck Gail. But Ralph didn’t mean that at all. So when Stacy had sucked him until his cock was steel hard, he said, “Okay, I think I’m ready now. I’ll just climb over on top of Gail, and you can hold my cock and help me push it in. Then you can wank off while you watch me fuck her.” “But… I thought we were both gonna fuck her, Ralph. Can’t we do that?” “Nah. I don’t share my women while I’m fuckin ‘em. But I’ll tell you what. When I’m done, I’ll try to convince her to let you fuck her, okay?” Stacy just nodded as he took Ralph’s cock in his hands and inserted the tip into Gail’s cunt. Ralph applied a bit of pressure and his rampart cock slid easily into my well-lubricated cunt. “Thataway, Stacy. Ya did good. Now just stand right here beside the bed and watch what I do. An hour and a half later, Ralph rolled off of Gail and reclined beside her. He had fucked her every way known to man, plus a few nobody had ever tried, and they were both sweating from the passion and intensity of the coupling. “How we ding there, Stacy? Did you cum yet?” asked Ralph. “Uh… no, I saved it so I could fuck Gail like you said.” “Oh, yeah. I said that didn’t I? Well, Gail, what do you think? You want to give my helper here a little fuck?” “Oh, Ralph, you know you wore me out. I’m just not up to it. Tell you what, though. I’ll let Stacy show you how he fucked me yesterday.” Gail motioned Stacy onto the bed. “Okay, sissy you can fuck my leg if you want. But go easy, ‘cause I’m really tired.” Well, I could certainly tell that Stacy was disappointed, but I guess he decided my leg was better than nothing, so he took about fifteen minutes of massaging his cock on the calf of my left leg until he spurted his small load of cum onto my stocking. When he finished I pushed him away and said, “I think I’ll just stay here for the night. Anyone want to join me?” Stacy’s eyes brightened, and he volunteered, “I do. I do.” “You’re not anyone, sissy. Ralph is anyone.” Ralph chimed in, “Aww, Gail, let’s give the guy a break.” Stacy didn’t see Ralph wink at me, but I knew Ralph must have an idea to further humiliate my sissy. So I said, “What’s that, Ralph?” “I’ll spend the night, and Stacy can sleep on the bed with us if he keeps my cock in his mouth the whole night. What do you think?” I just smiled an evil smile. But Stacy, not having slept on a bed in quite a while was eager to accept the rules. “I… I’ll do it.” And he did. I woke up two or three times during the night, and Stacy’s head was right where he started, resting on Ralph’s upper thigh, with the cock in his mouth, sucking very, very gently, as if it were a teat. I think he was asleep the whole time. Things are coming along nicely with my plaything. I finally had to shoo him from the bed to get breakfast ready. He had cum dripping from his mouth. How very sweet. What will sissy Stacy face today? Will Gail find more ways to humiliate the poor man? Stay tuned. A Natural Sissy Ch. 05 Author's note: This is a story about a woman turning a man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justify it. Ch. 05 Stacy's Interlude "Hi, guys. I'm Stacy, and I guess you know I'm a sissy from what Gail has been writing about me. I don't mind being called a sissy, because that's exactly what I am, and we should all be proud of what we are, shouldn't we? Gail told me that I needed to write this chapter, and tell you some of the things she has learned about me from our private talks. I resisted at first, but when she threatened to tie me to the toilet with my face up so all her friends could come visit and piss in my mouth, I decided that compromise was my best option. I've tasted piss before, and everyone knows it's sterile, but I just don't like the taste. So just sit back and listen while I tell you a little about me and how I grew up as a rich kid. Yeah, my parents were very rich. My dad, who I didn't know was my dad until I was a teenager... well that's getting ahead of the story. Let me just say 'he' never worked a day in his life – at least not for pay. He inherited a really big estate when his parents died, just like I did later. My mom was rich, too. When I was small, she would go off everyday and not come home until sometimes very late at night, and sometimes it was late morning when she got home. She never told me what she did while she was gone, and I only found out when my two older sisters sat me down when I was thirteen and told me. I remember that day like it was just yesterday. Here I was, dressed just like my sisters, in a girl's school uniform. They wore them to school everyday, but I was wearing one because I was being punished for mouthing off to my oldest sister. Did I say that my sisters had absolute authority from my mom to discipline me when they wanted to? I didn't? Well, it's true. So here I was, dressed like a schoolgirl, except I didn't look like a schoolgirl because my hair was short, like any other boy. The younger of my older sisters was doing things to me that I can't mention, until I yelled, and then they would both laugh their heads off. I didn't dare talk back to them, because one time I did that and they took me down to the dungeon, and strapped me to something they called a St. Andrew's cross, and they beat me with all kinds of things they took down from the dungeon wall. I never want to go through that again. Anyway, my sister let something slip about what mom was doing that day, and when I asked what she was talking about, they whispered to each other for a minute. Then one of them said, "Okay Stacy, I guess you're old enough to know. Mom is a professional dominatrix. Do you know what that is?" I did, because I had been reading erotica stories from Literotica and other websites since I was ten. But I feigned innocence. "No. What's that?" So I got the whole nine yards about my mom. She made her money training men to be subservient to women. Her clients even included royalty from all over the world, and all her clients were near the top of the wealth chain. She was too, because her fees were out of sight. And none of it was reported to the IRS. Only my dad's inherited money was reported. But I still didn't know who my dad was. It wasn't until I was about to go away to college that I found out our live-in maid was my dad. He was absolutely gorgeous, and I wanked off thinking about him when I went to bed at night. He was the most beautiful woman I had ever seen. I mean he put movie stars to shame he was so beautiful. But he was always rather quiet around the house. And he always deferred to my mom and my sisters in everything. I guess mom had trained him well. Being the baby in the family, I was always the first to bed every night, and as I look back I realize that some of the strange noises I heard after I went to bed were my dad being disciplined by my mom and sisters for some fault they found with him. Some of the noises were not discipline at all. Well maybe they were, but they didn't sound like it. I've heard the same noises as an adult, and they were definitely sexual in nature. My mom and my sisters were using my dad the same way I get used by Gail now. Anyway, after I went off to college, I though about my dad, and the life he lived, and how beautiful he was. Or she. Having been dressed as a schoolgirl by my sisters kinda crept up on me, and combined with my images of my dad, I developed a desire to dress like a woman. I didn't want to be a woman, but I certainly wanted to look like one. Does that make any sense to any of you? I bought a few things that ladies wear, mostly lingerie, but a couple of really smart looking dresses, and a wig. Since I was a wealthy kid, I lived in my own apartment off campus. Every night, after classes were over, I'd go home and change into lingerie and put on a dress and the wig, and pretend I was a beautiful, rich lady. That even carried over when I graduated and started working as an electrical engineer. I dressed whenever I could in my ladies wear. I moved up rapidly in my profession because I'm smart. Eventually I became the CEO of a large software developer. I won't tell you which one, because you'd recognize it right off, I'm sure. And I don't want to stain their stellar reputation by having it known publicly that the CEO was a cross-dressing sissy. Let's just say I was rich in my own right when my parents died in a tragic automobile accident some years back. The news about the accident hit newspapers around the world, but they were soon squelched by money. My sisters told me later that my mom was doing weird, perverse, things to my dad in the back of the limo, and it distracted the driver, who ran head on into an 18 wheeler coming the other way, killing all except the truck driver. In settling the estate my sisters got the larger share, as is only right because they are ladies and I'm just a sissy. So they got joint ownership of mom's business, and each of them got 2/5ths of the rest of the estate. I haven't had much contact with either of my sisters in a while, but as far as I know, they are still running the business my mom started, and doing quite well. That left me with 1/5th of the estate, which, when added to my own hard earned wealth, made me very, very rich indeed. No, I won't share any of it with you. It's mine. Well except for what I put in trust for Gail. Two-thirds of it. And no, Gail didn't ask for it. I did it because I love her. And if I die before she does, she will get everything else that I have. I was still cross-dressing when I first met Gail on an Internet forum, and as our relationship online progressed I let down my guard and told her a lot about myself, but didn't mention the dressing thing. But she's a smart lady, and in reading between the lines I guess she recognized a sissy. Turned out that she has trained a few herself, so she has a kind of kinship with my mom. And that's not a bad thing at all. I loved my mom, and I love Gail. And that's what brought me to be where I am now. And yes, I'm very, very happy with my station in life. I do have ambitions to be a beautiful lady like my dad was, and it will happen. I know it will, because Gail loves me, and she will let me do it someday, when she's ready. Yes, of course it's her decision to make. Who the hell else would make such a decision for me? Oh, excuse me for a moment. Someone's at the door. Okay, I'm back. Sorry it took so long. It was the new neighbors from next door. Adriana and Joel, or Joy, maybe is his name. I heard Adriana call him both while she was talking to Gail. They're all in the bedroom right now, and it's getting a little noisy up there. Can you hang on a sec? I need to go ask them to hold it down a little so I can think what I need to tell you next. Be right back. Just help yourselves to some refreshment while I'm gone. I'm back. Sorry about the delay. I had to watch for a few minutes. The new neighbors are sure a friendly pair. Let me just take a moment to tell you what I saw up there. I guess this Joel guy, or Joy... whatever, is a sissy like me. I thought he looked kinda meek when they came in, and he didn't say a lot, but when he did, he curtsied, even thought he wasn't dressed like a girl... then, anyway. But now he is. He's wearing his own lingerie, but he has on a pair of my high heels, and my best wig. I guess the makeup he's wearing is mine too. Anyway, Gail is naked as a jaybird, lying on the bed, and Joy's head is right there between Gail's legs, and he's slurping at her pussy like mad. Gail had her hands on his head, guiding him in deeper, I guess with his tongue extended. That's the way I do it, anyway, and Gail likes it just fine. But get this. Adriana is buck naked, too, and she's wearing Gail's really big strap on. The biggest one we have, and she's fucking Joy like there's no tomorrow. It's a really hot scene, if you know what I mean. She's pounding his ass so hard she's driving him deeper and deeper onto Gail's sweet pussy. Well, enough of that. Where was I, when I was interrupted? Oh, yeah, I was telling you about my ambition to look like a beautiful woman like my dad was. So... Well dammit, I just got called upstairs, so I guess I'm done with my story for now. Maybe Gail will let me write another chapter later. Bye now. A Natural Sissy Ch. 06 Author's note: This is a story about a woman turning a man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justifies it. Chapter 06: Stacy Finds Joy With Joy I had told Stacy to write about how he came to be a sissy, even before I set it in concrete. But I need him up here in the bedroom now for another round of sissy humiliation. I've been entertaining Amanda and Joel, or Joy, I guess I should say. They just moved in next door a couple of days ago, and Amanda and I had a nice conversation yesterday after she revealed that her husband Joel was a sissy extraordinaire. I had asked her to bring her sissy over today to meet mine. We've just finished humiliating Joy, and now Stacy is on his way up to meet Joy. "Oh, there you are, Stacy. I think you spoke to Amanda and Joy when they arrived, but now I want you to get to know them better, so get your clothes off and join us on the bed." I watched Stacy as he looked at the bed, probably wondering where he could find space since there were three of us there already. But then he started carefully removing his outer clothing. When he was down to his bra, crotch-less panties, garter belt and stockings, I said, "That's far enough, dear. Now just climb up here next to me." I unceremoniously shoved Joy over to make room. He landed on top of Amanda. That's right, now, on your back, honey buns." As he settled back on the bed I started stroking his cock to see if he had taken his Viagra this morning. He had. His nine inches were aimed at the ceiling like a flagpole. It was time to start the game. "Now, Joy, I want you to get over Stacy, with your little clitty right over his mouth. Then I want you to suck Stacy's nice big cock for him and see if you can entice him to suck your little clit." Joy was a bit under endowed, so calling it a clit was a source of embarrassment for him. I saw his face flush as he climbed on top of Stacy and silently began sucking. Amanda broke in, "Joy, if you fail to get Stacy to suck your clitty, your ass is in serious trouble, so you'd better damn well start working on that cock like you mean it." I smiled as Joy started sucking more seriously, and he licked Stacy's shaft from top to bottom and back again several times, pausing to twirl his tongue over the head of Stacy's rampart cock, then licking the opening where he hoped some cum would appear shortly. Stacy's cock responded, twitching rapidly. I said, "Stacy, you are not to suck Joy's little clitty until you just can't stand it any more. But when Joy really starts to please your cock in earnest, you may suck it." Stacy hasn't had his cock sucked in a long time, so naturally, it wasn't long until he leaned his head up and took Joy's small cock in his mouth. It only took three or four sucks to bring Joy to a full-blown ejaculation. As he jerked, his cock was pulled from Stacy's mouth, and his cum spilled onto Stacy's face. This in turn triggered Stacy and he exploded, too, his larger dose if cum hitting the back of Joy's throat, causing Joy to have to swallow. Meanwhile, Amanda and I took seats in the occasional chairs beside the bed and watched to two sissies as they recovered from their experience. Joy finally rolled off of Stacy, and rearranged him to recline next to Stacy. "Oh, Stacy, darling, that was wonderful. I think I'm in love. Will you be my sweetheart?" Joy begged. Stacy looked at me for a clue how he should respond. He certainly didn't want to upset me. I nodded in perceptively in assent. "I guess so Joy, since you live right next door, I guess it would be alright." That really set Joy off. He took Stacy's head in both hands and started kissing him wildly, showering kisses all over his face. "Oh, I'm so happy, Stacy. Amanda, is it alright? I mean, I should have asked." "Yes, Joelie, it's alright. I think it will do you both a lot of good to be girlfriends. But you must understand that Stacy will be in charge, and you must always obey her when you are together." "Oh, I will. I will. Stacy, I'll do whatever you say." Stacy looked a bit confused. It has been a long time since he was in charge of anything, much less another sissy. I noticed that Amanda was now calling Joy by another name. Joelie. So I asked, "What's with the name change, Amanda?" "Oh, that? That's what I cal him at home. I only call him Joy when we are with people we don't know well. But now that we are becoming good friends, I'd prefer that we all call him Joelie, even when we are out together. Well, unless the guys are in male mode." I didn't quite understand the logic behind all of that, but I didn't question it. "Okay, Joelie, it is. Did you hear that Stacy? Joy is Joelie from now on." Stacy replied, "Yes ma'am, I heard it. I like Joelie better, myself. It has a certain ring to it." "It's time to go downstairs now, Amanda. Let's get our clothes on and we'll wait for the sissies to shower and come down in a few minutes. Sissies, no more clothes than you are in now after you shower. Then downstairs, understood?" In unison, "Yes, ma'am." The guys rushed to the shower as Amanda and I went downstairs. It was quite a while before the sissies showed up, profusely apologizing for taking so much time. It's alright," I said, "I know how it is when you find a new love." Amanda just smirked. "So what do you want us to do, Gail," Stacy ventured. "I think you two need to spend some more time together, don't you think?" "Oh, yes ma'am," Joelie rushed to reply. "What do you want me to do, Stacy?" Stacy was hesitant. So Joelie continued, "I'll suck your pretty cock again if you want me to. Or whatever." Stacy didn't know what to say. He looked at me for a sign of a hint. I just nodded. Then Amanda chimed in, "That's a good idea. Stacy, why don't you sit over here in this chair, and Joelie can kneel between your legs and suck all he wants." So that's what the two sissies did, while Amanda and I just chatted the hours away. I noticed that Joelie was a great cocksucker, and he had Stacy climbing the walls. It took a while for Stacy to cum again, even with the exquisite manipulations he was getting from his newfound friend. Once or twice I noticed that Stacy took charge, and began fucking Joe lie's face a bit harshly. Neither Amanda nor I said anything to them. Then the moment came. Stacy started moaning, followed by incantations of "Oh, my. Oh, my." Then he rammed his cock down Joelie's throat and let loose a massive load of cum. Everyone was surprised, especially Joelie, who coughed and gagged at the intrusion of his throat. I couldn't help but comment. "Stacy, look what you've done. Poor Joelie is coughing and sputtering because you got carried away. I think you need to apologize." "Oh, no, Miss Gail. Stacy is in charge, and he can do whatever he wants. He should never apologize to me for anything he does." Before Stacy could chime in, I answered, "Well, that's all well and good, Jolie, but Stacy needs to mind his manners. So he's going to give you a nice blowjob now, aren't you, Stacy?" I glanced at Amanda briefly, and she was trying so hard not to break out in a fit of laughter. "Yes, ma'am. I guess I do owe Joelie something for that wonderful job he did for me. Sit down here, Joelie. I'm gonna give you a nice blowjob, just like you did me." Joelie looked at Amanda, to see if she thought it was okay. Amanda just nodded, almost imperceptivity. The evening wore on, with the sissies whispering to each other, giggling, and pumping each other's cock. Finally, Amanda thought it best to end the time together, and excused the pair, "It's time we get going, Gail. Joelie has some chores to finish before bedtime, and it's already getting late. We enjoyed the visit, and we need to do this on a regular basis, now that the sissies are such good friends." I rose as Amanda did. "It is rather late, and Stacy has lingerie to wash by hand and one or two other things to do as well. It has been a very nice visit. Come back anytime. Oh, and call me tomorrow around lunchtime, will you?" "I will. Come along Joelie. Time to get to work." There were kisses and hugs all around, and then they left for their home next door. What's the phone call all about, dear reader? And what else will tomorrow bring? A Natural Sissy Ch. 07 Author's note: This is a story about a young woman turning an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justifies it. Sorry about the delay in getting this chapter up. Real life gets in the way at times. Ch. 07 Stacy has a bad? morning The next morning I slept in a bit. Stacy woke me by climbing onto the bed and spreading my legs as was the method prescribed for such times. Stacy was a world-class pussy eater, and I guess I have his sisters to thank for that. When my orgasm came I opened my eyes to see Stacy's face right in mine. He was grinning broadly, I guess with pride. : Breakfast is ready, Miss Gail." He said. :"Or shall I keep it warm until later?" "No, now is fine, Stacy. Set a place at table for yourself, too. We have something to talk about before we start the day." "Yes, ma'am." Stacy was off the bed and out of the room before I could muster a reply. When I got to the breakfast nook, the table was ready, and it was a heavy breakfast for us both. Stacy had prepared a dozen eggs, biscuits and gravy, sausage and bacon, orange juice, fresh fruit, and best of all, hot coffee. As we ate, Stacy kept watching me, waiting for me to begin listing his assignments for the day. Well, I guess it's time to tell him. "When we finish breakfast just throw the dirty dishes in the sink, and go get dressed. We're going to visit Heather this morning. You remember my friend Heather, don't you Stacy?" Stacy frowned. I knew he didn't like Heather. She was kind of uppity, I guess, but I still counted her as one of my best friends. Stacy was silent. "Don't worry, sweetie, I'll not let her rape you again like the last time you saw her. We just need to set up an appointment with her for this afternoon. Now, let's get the show on the road, shall we?" I smiled at my boi toy in my most charming way. That always melted Stacy, and he would do anything to keep getting those smiles. "I have already laid out what you will wear to the meeting. We need to be ready to go in half an hour." "Yes, Miss Gail. I'll start right away," answered the poor sissy as he rose to go dress. He wasn't aware of what I had set out for him, but I didn't expect any backtalk. He was too well trained now for that. He would be wearing a modified male suit over lingerie. Matching red lingerie. Bra, garter belt with silk stockings, panties with an open crotch, and red patent leather high heel pumps. He would likely not like the blouse I had put out, but he would wear it. There was no doubt about that. It was a sheer white frilly thing that offered no concealment at all. His red bra would be quite visible. His "manly" tie would match his lingerie perfectly. It was solid red except for the design at the bottom, which read, "I give great head" in French script. Of course, he'd round out his ensemble with dangling gold earrings that brushed his shoulders when he wore them. His suit coat was unmodified, but the trousers were. I'd had a tailor fit then to his measurements in a way that made them skin tight. His cute butt would stretch the trousers to the point of slutty, and the legs would hug his thighs like he was poured into them. They were shortened to end at a cuff three inches above his ankles, so his stockings and high heel pumps would be very obvious. I had not put out a wig, so he's be wearing his natural male cut hair. Subtle pink makeup would round out his persona for the trip to the tattoo parlor that Heather owned and operated. No, the tattoos would not be done in the parlor. Heather would come to the house, a much more relaxed atmosphere for us ladies. Not so sure about the sissy, though. He had mentioned that he'd like a feminine tattoo on his breast, and that's what he will think he's getting. He'll be right about that, but there would be moiré that he doesn't know about. I'll tell you about that later. Stacy's on his way down now, and we need to get going. "Oh, there you are, sweetie. With just enough time to spare to take your Viagra before we leave. Hurry now, darling. Heather doesn't like people to be late for appointments." We arrived at the strip mall where Heather's parlor was located at just the right time. All the stores were opening and customers abounded. I chose a parking place as far from the parlor as I could. "Why... why... did you park so far away, Miss Gail?" "Oh, because I have a cramp in my leg, and I need to walk it off. Come along now. We need to hurry." As we made out way across the parking lot, Stacy was on full display to hundreds of mall shoppers coming and going. His high heels clicking on the pavement brought attention to the sissy, and his cock was plainly outlined by the skintight trousers he wore. I stopped him when he tried to button the suit coat, and of course his red bra was obvious to any who chose to look. Finally, we were at the door to Heather's parlor, and she came out to welcome us. She and I hugged, like the dear friends we were, and then she looked at Stacy, her hands on her hips, her legs spread, stretching her mini skirt to the limit. "Stacy, aren't you going to give me a nice manly kiss like last time we met? I'm sure Gail will time it for you." "Uh... here, Miss Heather? Out here on the sidewalk?" "Of course, right here, darling. Why would you think not?" "There's a lot of people here. Inside wouldn't be so crowded." "Crowds don't bother me. Are you going to kiss me, or not?" I was almost ready to burst out laughing, I was so amused at Heather's antics. Stacy was really getting nervous now, I could tell. He was looking around to see how many people were nearby, and there were a lot of them. "Er... um..." "Come on, Stacy. Wrap your arms around me and give me one of your alpha type kisses, you delicious hunk of masculinity." Talk about sarcasm, I thought. Finally, Stacy decided that he was not going to get out of this predicament, so he knelt on the sidewalk, raised Heather's mini skirt, exposing her naked pussy, wrapped his arms around her luscious thighs, and began his kiss. Her pussy, of course. I understood that it was to be a three-minute French kiss so I timed it for them. When it was over, a crowd had gathered, and applauded with gusto. "Here, here!" " Bravo." " Good job, my man." " Would you like to kiss me, too?" Poor Stacy. He was beet red. Heather was quite calm. She unceremoniously grabbed Stacy's tie and pulled him along on his knees into her parlor. I followed quietly. This was Heather's show. The actual discussion about the appointment was brief. Heather and I had already made all the necessary arrangements by telephone. This visit was just to humiliate Stacy. Every sissy needs that as often as can be arranged. Heather escorted us out of the parlor five minutes after we arrived, and demanded a goodbye kiss from Stacy. She also stipulated that she needed to see how Stacy reacted to the kiss, so he was to extract his clitoris (cock) and leave it exposed during the kiss. This was no small feat for a rock hard nine inch cock confined by skin tight trousers, and it too the poor sissy a good three minutes just to do that. He had to pull his ovaries (balls) out, too if he was to have any comfort at all. The goodbye kiss lasted five minutes, long enough for Stacy to ejaculate just from the thrill of his embarrassment. I told you he was a natural, didn't I? Before he could stuff his still hard cock back in his trousers, I grabbed it and led him, using his cock as a leash, across the parking lot to my car at the far end. Stacy said not a word the entire ride home. Amanda called just as we entered the house. I sent Stacy to change clothes while I invited Amanda to visit during the afternoon while Heather was doing her chosen line of work in the recreation room downstairs. We'd use Jolle as our entertainment. When Stacy was back downstairs, I asked, "Did you enjoy our little outing this morning, dear?" "No!. Not one bit, and you know it." He was livid. He was wearing his usual lingerie with no outerwear. "Oh, come on, Stacy. Your body said otherwise. I've never seen your cock any harder that when you were sergvicing Heather on the sidewalk in public." "Well, I..." "Well, you did enjoy it. I could see." "I... I guess it was okay," the sissy conceded. "Right on. Now get us some lunch ready, sweetheart. It's going to be busy around here this afternoon." I gently squeezed his rising cock, dismissing him to his chore. After lunch, I sent him to the recreation room to get it ready as a makeshift tattoo parlor. Just what would our sissy have to endure this afternoon, dear reader? Stay tuned. It's coming next A Natural Sissy Ch. 08 Author's note: This is a multi-part story about a young woman turning an older man into a compliant, sissified plaything. It is best understood if you read from the beginning. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justifies it. One reader suggested that I insert a cast of characters to make the story easier to follow. I can do that with the characters already in the story, but I have no idea where this story is going, so new characters will likely be introduced as Stacy is further humiliated. Not all the characters will appear in every chapter CAST OF CHARACTERS Gail -- narrator and lead female character. She is the one who controls Stacy's life. Stacy -- an older man (the sissy) under the control of Gail. The subject of Gail's mischief. Ralph -- A VERY close friend of Gail's, with privileges. Amanda -- New neighbor to Gail and Stacy. Joel/Joy/Jolie/Jolle -- Adriana's sissy husband. Wanda and Shirley -- minor characters, friends of Gail, who once mentioned, may or may not reappear in future chapters. Heather -- Gail's friend who operates a tattoo parlor. Brut -- a released felon who now works for Heather as her bodyguard. Other characters will be added, as required, to interface with Gail and Stacy as the adventure progresses. * Just as Stacy came back upstairs and told me the recreation room was ready for his tattoo application, the doorbell rang. "That's fine, Stacy. And just in the nick of time. That must be Heather at the door. Go let her in, please." Stacy looked at me like he could stab me in the chest with his eyes, but he turned to answer the door. He was wearing only his bra, garter belt with stockings, and high heels. Not even a panty or wig. I just sat to see what would happen. He ushered Heather into the living room, and I saw a very large black man follow them in. I knew of Brut, but had never met him. He just recently got out of prison after serving two years for raping a single white mother of two small children. Now he was working for Heather, who has known him for years. Heather grabbed Stacy by the balls and pulled down hard as she said, "Stacy, dear, aren't you going to give me a nice welcoming kiss now that I've come to visit?" When he was kneeling, she grabbed his ears and pulled his face to her crotch, covered only by a very short mini skirt. Poor Stacy. What a sissy must endure. He only said, "Yes, Miss Heather," before raising her skirt and beginning cunnilingus, thrusting his tongue into her pussy. Brut pulled a stopwatch out of his pocket to time the kiss. Heather didn't let go of Stacy's ears for a full six minutes while he "kissed" her. Then with a nudge from Brut she said, "that was a wonderful welcome, Stacy. I'm so glad we're such good friends. She helped him up, and continued, "I'd like you to meet my assistant, Stacy. This is Brut. I'm sure he'd like a nice welcome to your home as well." Stacy sighed. He knew better than to question what was about to happen. He walked to Brut and without a word knelt, his face just inches from Brut's crotch. Brut was way ahead of him, with his trousers already down to his knees. I knew immediately that this would not be a blow job. It would be a face fuck. Brut took Stacy's head in hand to hold him still, and started what would become a very lengthy face fuck. Heather came and sat by me as we watched Stacy try to take 13 inches of hard black cock in his mouth. Now the unsupported myth is that black men have much larger cocks than white men, but in Brut's case, it was no myth. He crammed his mammoth tool as far as Stacy could take it, to the point of asphyxiation. He only backed out when Stacy was at the point of passing out. Stacy is an accomplished deepthroater with any lesser cock, but this thing was enormous. After about twenty minutes Brut finally unloaded in Stacy's throat with a yell, "Yeah, man! That was a great welcome." He pulled out, grabbed Stacy under each arm and lifted him to a standing position. Next, he took Stacy's nipples, through the bra, between finger and thump, and twisted as he planted a sloppy wet kiss on Stacy's quivering lips. When he broke the kiss, Brut said, "Yeah, Stacy, I can tell we're gonna be good friends, Real good friends." Then he looked at Heather and asked, "Ma'am, are you ready?" When he got an affirmative answer from Heather, he picked Stacy up, placed him securely under one arm, and said to me, "Lead the way, ma'am. You and I can get acquainted while Heather does her work. Now that was an offer I couldn't refuse. I led the pair downstairs, Brut with Stacy under one arm and a heavy, tool-laden kit in his other hand. Heather's tools of her trade, of course. In no time at all, and over vigorous objections from Stacy that he could certainly have a tattoo applied without being strapped to a table, he was securely strapped down. Heather wasted no time getting her tools ready for the job at hand. When she approached Stacy with a hypodermic needle, Stacy yelled, "What's that? What are you doing?" "I'm just going to administer a light sedative so you won't feel the pain, sweetheart. Everything will be okay." She unceremoniously jabbed the needle into Stacy's thigh and pushed the plunger. Stacy was out like a light in just seconds. Then she looked at me and said, "He'll be out until morning, Gail. Are you sure you want me to do everything we talked about earlier?' "Certainly, honey. The works. Now, unless you need Brut here, I'll take him upstairs and entertain him while you work." "Go right ahead. Brut is my bodyguard, not my assistant. I'm in no danger here. Have fun." I have absolutely no idea what Heather did, except that she took a good part of the rest of the day doing it. Well, I know she would do what I asked her to do, but how she did it is beyond me. Brut and I, on the other hand, had quite a time. Amanda brought Joelie over as we had planned, and that's what I'm going to tell you about. I'll get back to Stacy later. Brut had me pinned naked to the sofa when the doorbell announced the arrival of my neighbors. He pulled his cock from my pussy in exasperation, and said, "Who the fuck? Can't a guy get some sweet white pussy without being interrupted anymore?" I was as exasperated as he was, because he had me at the peak of an orgasm when the bell rang. "Crap," I replied. "Isn't that just like Amanda, to interrupt the best fuck I've had in years?" I threw the door open, startling Joelie so that he backed away quickly. Only Amanda's quick response saved the high-heeled sissy from falling. Joelie was dressed as a full-blown sissy, in pink skintight trousers with no crotch, so the leash attached to his ball harness was free of any encumbrance. I quickly took the offered leash from Amanda and pulled it taught, forcing the ball harness forward, with Joelie's balls now stretched along with the harness. "Come on sissy boi. Let's get inside so I can introduce you to someone special." Brut was standing, still naked, his huge cock throbbing, when we entered the living room. I stopped with Joelie right in front of Brut. "Joelie, this is Brut. Suck his cock." Joelie looked briefly at Amanda for any sign of rescue, but Amanda gave none. As she and I started for the kitchen to fetch a bottle of wine, Brut pushed Joelie down on his knees, saying, "Gail didn't tell me your name, boy, so I'll just call you Cocksucker until she does. Get busy." When Amanda and I returned with the wine and three flutes, Brut had put Joelie face up on the coffee table, his head hanging off the end. It was obvious that, by kneeling, Brut had a straight passage down Joelie's throat at the angle presented. He wasted no time forcing his huge cock in as far as it would go. He held it in place until Joelie was about to pass out from lack of air, then backed out enough for the sissy to take a breath, then he forced his cock in again. It was a game for Brut. He continued this action over and over for almost ten minutes before he unloaded in Joelie's throat. The poor sissy almost drowned. When Brut released his victim and reached for the filled wine flute I offered, Joelie was gasping and coughing. Finally, Joelie was able to recover normal breating, and rolled himself from the coffee table onto the floor, sitting with his legs crossed like an Indian. He kept trying to ask a question, but was interrupted for quite some time. Finally, exasperated he continued with his question anyway. "May I have something to drink? I need to rinse my mouth." "Well, I don't know, Joelie." Then looking at Amanda, I asked, "Can the sissy have something to drink?" "Sure. I brought his bottle." She rummaged through a satchel she had with her and pulled out a baby bottle filled with what looked like a slightly milky substance. The nipple of the bottle was a miniature cock about two inches long. "Here, sissy. Here's you bottle. Drink it all down like a good boi." She handed the bottle to him and he started sucking the cock-shaped nipple. Brut asked before I could, "What's in the bottle?" "His cum from a week of milkings. I save it in the refrigerator, and when the bottle's full, I give it to him to drink." Brut spewed wine as he started laughing. Then he spoke. "I've heard of that, but I'm not sure how it's done." He broke out laughing again. Amanda picked up the conversation. "It's not a secret. The way I do it is put him face down naked on the bed with his cockhead in a cup to catch the cum. Then I go into his rectum with my fingers and massage his prostrate gland until the cum spills into the cup. In Joelie's case there is never an orgasm, and that's why I do it. It robs him of semen when he masturbates while he thinks I'm not paying attention." Brut and I both burst out laughing. Joelie was not pleased at our laughter, but what the hell. Sissies are not to be pleased, they are to please. The evening continued with more humiliation for Joelie. We had him model many of Stacy's dresses and lingerie, and when any of us didn't like the way he performed he got some kind of punishment and the need to make up for his deficiency by sucking cock or cunt. Late in the evening, Heather came up and asked Brut to bring Stacy up from the recreation room. When that was done we all inspected the magnificent work that Heather had done. But I was getting sleepy, so I asked Amanda to take Joelie home so I could rest. Heather and Brut stayed the night just to be sure Stacy was okay. I could hear them fucking through the night in the guest bedroom. It was obviously a mistress handling her subject. The next installment will reveal what Stacy had done to him.