A Cuck Story

Part 2

For a few days after Rob's first visit, things went somewhat back to normal between Annie and me, but I could tell that something had changed. Annie was making no bones about the fact that she was regularly in touch with Rob and that he would be coming back soon, and for the first time she wasn't so much as asking my opinion. A couple of days after that fateful night, as she rode me and brought me close to a climax, she made me admit that the whole humiliating ordeal had turned me on and that I wanted it to happen again, before allowing me to cum inside her. And so Rob came back a week after his first visit to our house. This time, Annie and I set the wine (with just two glasses) and snacks on the table ahead of time. When the knock came at the door, Annie opened it and welcomed Rob in with a long, full kiss on the lips, while he groped her and I stood quietly. After a good 30 seconds, Rob finally turned towards me and smiled. "Hey sissy," he said. "Hello, Sir," I replied, feeling myself blush. Rob took off his jacket and handed it to me, then led my wife to the living room. After hanging it up, I joined them, intending to sit in the armchair once again, but Rob had other ideas. "Cucky, today I want you to take your clothes off and kneel over there," he said, pointing to the corner. "We'll let you know if we need you." "Yes, Sir," I said meekly, and began to strip. Annie giggled and began kissing the younger man. Once I was in position, with a full view of the show, Rob addressed me again. "Next time I want you in lingerie as soon as I get here, for today you can borrow your wife's again after I take it off her." "Yes, Sir." "I'm planning on turning you into a full-blown sissy." I wasn't sure what that mean, so I just repeated my "Yes, Sir" mantra. For the next several minutes, I tried to ignore how uncomfortable I was kneeling on the floor while my wife and her lover made out and gradually shed their clothes. When Annie was naked, Rob tossed me her bra and panties with the instruction to put them on. I immediately obeyed, pulling up the black lace undies, but couldn't snap the bra closed. After I fumbled for a few moments, my wife noticed and laughed. "Aww, do you need some help with your bra, sweetie?" she asked mockingly. "Yes, please, Ma'am," I replied in the small voice I'd found myself using. "Crawl over here," she said. I did. "Now turn around." She fastened the bra and gave me a pat on the head. "What do you say, sissy?" said Rob. "Thank you, Ma'am," I replied. "You're very welcome, sissy. Now go back to your corner." I crawled back and turned to face them, undeniably enjoying the feel of my wife's lacy lingerie against my skin. A few minutes later, Annie and Rob, fully naked, rose and walked to the bedroom, indicating that I should crawl behind them. I took my place on the floor, and for the second time watched Rob fuck my wife. This time, as he rolled off her, he addressed me. "You know where this is going to end up, don't you sissy?" he asked, referring to the very full condom on his still half-hard penis. "Yes, Sir," I replied, remembering how I had sucked out the contents last week. "Good. Come over here, take it off me and put it in your mouth." "Yes, Sir." I started to crawl forward. "You have my permission to touch me." "Thank you, Sir," I replied without thinking. "Good boy," he chuckled. "Don't lose any of it." As I peeled the used condom off him, I could see that Annie was staring at me intently, but I was too embarrassed to look straight at her. For the second time in a week, I put the condom into my mouth and started sucking, swallowing the bull's cum. "You're such a pussy," sneered Rob as Annie snuggled up against him. "Start rubbing yourself through your panties. You have permission to cum." "Thank you, Sir," I mumbled, my mouth full. My dick was already straining against the lacy fabric, and in an embarrassingly short two or three minutes I exploded into the panties. Rob turned to Annie. "We'll have to get him his own panties so he stops ruining yours," he said. She just laughed. I hadn't been given permission to clean up, so I remained kneeling, now empty condom in my mouth and cum in my panties, as the two lovers forgot about me and turned their attention toward each other. Annie again gave Rob a blowjob, but this time she swallowed, thus sparing me that particular indignity at least. I was still in my wife's dirty lingerie as I fetched Rob's jacket and thanked him, back on my knees, for visiting. It was less than a week before Rob visited again. Annie and I had sex a couple of times during those few days, but always with her on top, whispering in my ear, teasing me about our previous encounters with Rob and about what was still to come. My explosions of cum left me no room to argue about what was happening to our relationship. The night before his return, Annie made me suck all my cum out of her, in her words "to get me ready for tomorrow." The next day I worked from home as usual. When Annie returned from her own job she greeted me with a passionate kiss on the lips. She was clearly horny and excited for the evening. "Are you ready for tonight, baby?" she asked playfully. "Yes," I answered in the small voice I found myself using more and more these days. "I think you mean Yes, Ma'am," she chided playfully. "Yes, Ma'am," I corrected myself. "Good boy," she laughed, and taking me by the hand she led me to our bedroom. "Come on. I've been talking to Rob and I'm gonna get you ready for tonight." I followed without a word. "Strip," she ordered. I obeyed. "You remember Rob said he wanted you in lingerie as soon as he arrives today. But I don't want you stretching out any more of my stuff - or staining it. So I bought you your own the other day." She produced a shopping bag. "I think pink is totally your color," she teased, as she produced a pale pink bra, panty and stocking set, decorated with tiny bows. She held the panties out and I stepped into them. She pulled them out extra slowly, making sure to caress my legs. I breathed in sharply and closed my eyes, feeling my cock get hard already. As she pulled my panties all the way up, she lightly fondled my cock and balls. "How do they feel?" she whispered. "They feel good, Ma'am," I replied. "Good. You do NOT have permission to touch yourself," she laughed. As she fastened the bra and rolled the stockings up my legs, she excitedly told me about Rob's and her plans for me. "Rob is very excited about turning you into a sissy. The next step will be shaving off all that body hair, and pretty soon you'll be wearing panties all the time, and then dresses, and makeup... Is there something you'd like to say about that?" she added, grazing my rock hard cock straining in my panties with one finger. I just shook my head. Annie laughed. "No, I didn't think so. Now sit down, we're gonna start you on a little makeup tonight." I sat down next to her on the bed and for the next few minutes my wife applied blush, eye shadow and red lipstick to my face. She didn't talk much other than to instruct me to turn this way or that, so I had time to take stock of my situation. On the one hand I was mortified that Rob was soon going to see me like this - the fact that I was now wearing my own lingerie, and not some borrowed from Annie, somehow made it that much worse. On the other hand, I couldn't deny that I was incredibly turned on, and the careful personal attention Annie was paying me as she did my makeup made me wish she'd go on forever. But she did declare herself to be finished, and led me to the mirror to see myself. I suppose I didn't look as ridiculous as I expected, but I certainly didn't look like myself, and I didn't look like your average straight, married man. From the neck down I did look absurd, with my chest hair clearly visible despite the bra. Further down, my dick was still straining against the pink panties, which were already sporting a visible wet patch. The stockings were sheer and did not hide my hairy legs. "Alright, stop daydreaming, sister," Annie laughed, patting my ass over my panties. "Time to get me ready." I turned away from my reflection and looked at my beautiful wife as she began to undress. Once she was done, she produced the lingerie she would be wearing, a lacy and very sexy black basque, panties, garter belt and stockings, plus stiletto heels. My dick throbbed just looking at the outfit, which was new and she had clearly purchased for Rob's benefit. "One of your jobs will be to dress me for my bull," she announced. "Yes, Ma'am," I replied. So I proceeded to do just that. Despite knowing I was dressing her for another man, I found it an incredibly sensual experience. As I knelt before her, rolling up her stockings, attaching them to her garter belt, then delicately putting her shoes on, my cock was as hard as ever. From my submissive position, I looked up and my eyes met hers. She gazed at me for a few seconds, smiling, then stroked my face with her hand. In that moment, I saw that she still loved me. Despite my current attire and position, despite knowing that a younger man would soon be pleasuring her in ways I couldn't, I found that I was no longer afraid of losing her. As if to reassure me, she bent down and kissed me gently on the forehead. "Don't want to mess up your lipstick," she whispered. I smiled. As I prepared the wine and snacks for my wife and her lover, while she did her makeup in our bedroom, I found that my nerves had practically disappeared. They returned suddenly, however, when the doorbell rang. I took a deep breath and opened the door for Rob, who chuckled at the sight of me. "Good evening, Sir," I welcomed him. "Hey sissy," he replied as he walked past me. "You look ridiculous." Annie practically jumped into his arms as they kissed passionately. He took a few seconds to admire her outfit and led her straight to the bedroom. Clearly her lingerie had had the desired effect on him. Although I had been forgotten for the moment, I decided to follow and assumed my usual kneeling position, from which I was treated to a truly impressive display of lovemaking. Eventually they collapsed into each other's arms, naked, sweaty and exhausted. Once she caught her breath, Annie spoke to me. "Nick, bring the wine in here." "Yes, Ma'am," I replied immediately. I found that following my wife's orders, however mundane, was more thrilling than I ever could have imagined. I quickly returned with the bottle of wine, opened it and poured two glasses, then scuttled back to my kneeling position. Rob reached down and pulled a very full condom off his soft member. "Reward time, cucky," he announced. I crawled forward, accepted the condom and retreated again. Prior to this, Rob would leave after sex, but clearly today there was going to be a round two, and before long the two lovers began kissing again. Before he climbed on top of Annie, Rob spoke to me again. "I wasn't going to let you cum today, cuck. I want to start training you not to worry about your own pleasure. But, you've been really good this evening. I think you're really enjoying being turned into a sissy cuckold, which is good, because I have big plans for you. Anyway, you've earned a release. You can rub yourself through your pretty panties." "Thank you, Sir," I mumbled through a mouthful of condom. His cum was long gone, but I didn't dare say anything, so I began rubbing my dick as he mounted my wife. I came within a couple of minutes, so for the next half hour I knelt, empty condom in my mouth and a puddle of my own cum in my panties, and watched the show. By the time Rob came a second time, I was hard again, but I hadn't been given permission to touch myself any more so I kept my hands down. Finally, he took his second condom off, stuffed it in my mouth without letting me take the first one out, dressed and was on his way. For as little attention as Rob and Annie paid me when they were together in our house, I was clearly one of their main topics of conversation the rest of the time. I was obviously not privy to their exchanges (in fact I didn't even have Rob's phone number), but they were frequently in contact, and Annie wouldn't hesitate to text him when she was alone with me or even, increasingly, in public. I know they talked about me because, true to his word, Rob was indeed intent on making me a full-blown sissy, even if I initially didn't know what that would mean. Every few days, Annie would announce that it was time to add another feminizing element, all of which, it seemed, were Rob's idea and she endorsed fully. Within a few weeks, I was completely shaved from the eyebrows down, including around my cock and balls and in my ass crack. While this was initially achieved with a lot of Nair, I was given strict instructions to keep myself hairless by shaving frequently. While I was none too thrilled with this development, the first time I wore stockings on my smooth legs I had to admit that the sensation was heavenly. Speaking of stockings, my feminine wardrobe soon grew to four or five sets of lingerie. My wife declared that I looked ridiculous in a bra, so she took me to Victoria's Secret to buy some more loose-fitting babydolls, all in various shades of pink. She also went online to buy me a pair of pink shoes with three-inch heels. Once they arrived, she made me wear them around the house every day, even when I was otherwise wearing my normal clothes and Rob wasn't coming over, in order to practice. I was wearing my shoes, along with pink stockings, panties and a babydoll, one evening, about a month after our first encounter, when I opened the door for Rob and greeted him, as usual, with a "Welcome Sir, please come in." He swept past, still taller than me despite my heels, and joined Annie on the couch. As I served the wine, fully comfortable already in my role as the feminized cuckold, he announced that he had a present for me. Annie, clearly already in on the secret, giggled as Rob produced a pink plastic chastity cage. He had only been allowing me to cum about once every other time he came over, but apparently it had been decided that even that was too often. I obediently stood before my wife as she did the honors. She pulled down my panties and forced my semi-erect cock and balls through the plastic ring, making me wince a little. "This wouldn't hurt if you weren't hard," she mocked me. Once the second piece was on over my dick and the whole contraption locked, I found the cage was not too uncomfortable, which was good, because they announced I'd be wearing it anytime Rob was in the house. I meekly agreed with this decision, not that I had any say in it. The following week a package arrived at our house, addressed to Annie. When she came home from work, she eagerly opened it and produced three stainless steel butt plugs with pink jewels at their base, the next step in my sissification. She was so excited she decided she couldn't wait for Rob's next visit, so she had me drop my pants right then and there, lubed me up and gently inserted the smallest one, which I had to keep in until our bedtime a few hours later. For the next few weeks, there were no more surprises. Rob would come two or three times a week, and I would meet him at the door, dressed all in pink right down to my high-heeled shoes, my face made up, dick locked in chastity and butt plug firmly implanted. Annie and Rob would sit on the couch and enjoy each other's bodies while I stood at attention, refilling drinks as needed but otherwise unnoticed. Even as my feminization had progressed, my shameful enjoyment of it had not diminished. I loved the feel of the lingerie on my smooth skin, and I couldn't deny the pleasure the butt plugs gave me. I had graduated to the medium-sized one, but Annie still let me wear the small one most times. I had also become comfortable walking in my heels, and Annie declared that I was now moving quite gracefully, which I replied to with a genuine "Thank you, Ma'am" and a blush. Although I could no longer cum during Rob's visits, I invariably ended up with wet panties after leaking out of my cage. I had also, to my shame, become accustomed to the taste of Rob's semen as I lost count of the number of loads I had swallowed. I certainly couldn't say I enjoyed it, but I would feel the thrill of extreme humiliation when the younger man, having brought my wife to orgasm, would lower his used condom into my mouth as I knelt, femmed up, chastised and plugged, by our marital bed. The next step in my submission arrived in a nondescript package. It was, once again, addressed to Annie and clearly contained clothes, but I ignored it as I went about my working day at home. When she came home in the evening and saw it, she squealed like a giddy schoolgirl and marched me to our bedroom. It seemed the package was for me. As she opened it excitedly, she ordered me to strip. Blocking the contents from my view, she declared that she was going to put me in chastity first. Having done that, she lubed up my ass and inserted the medium-sized butt plug, which I was still getting used to, then turned her attention back to the package. The first thing to come out were the panties. Until then I had been wearing lacy panties, the kind any woman would wear. These were different. They were pink satin, with a big white bow on the front, and the back was decorated with white ruffles. It occurred to me that they seemed designed for a man to wear, as my caged cock fit comfortably in them. Annie giggled and clapped as she pulled them up my legs into place. She was thoroughly enjoying this, and she was also very turned on, as she rubbed my ruffled ass and pulled me in for a long kiss, then whispered, "I love you." The dress came next. It was made of the same pink satin, with white lace around the neckline, sleeves and hem. I had never worn a dress before, but the sensation of the satin all over my hairless body was incredibly thrilling. I knew that if I wasn't caged I would have been hard as a rock. I was still gathering myself from this new sensation when Annie turned me around and tied a white pinafore around my waist. She followed this by having me step into a white petticoat, which she pulled up and under the skirt of my dress. A pink choker and flower, which she pinned into my hair, completed the outfit. Annie stepped back and looked me up and down, a look of lust on her face. I just stood there, demurely fingering the hem of my new dress, feeling both incredibly self-conscious and incredibly turned on. After a few seconds, she moved closer to me and put her arms around my waist, looked into my eyes and kissed me deeply. I hadn't made out with Annie like this in months. Now, dressed as a French maid all in pink, our tongues met with a passion I feared had been lost. She pulled me onto the bed on top of her, but she would not be unlocking me. Within minutes, she was completely naked while I remained feminized. Annie pushed my head down and I got to work licking her beautiful pussy. It didn't take her long to cum in her aroused state. A few minutes later, we were resting, locked in a loving embrace. Annie, still naked, was sitting up. I rested my head on her chest, her juices still on my lips, as she stroked my hair, then ran her hand down my pink satin dress, at times kissing me on the forehead. Although I was acutely aware of my feminine clothes, and of the plug in my ass, I felt safe and loved. Finally she spoke: "Rob is coming tomorrow," she said, "and you'll be cooking and serving us dinner. From now on you're going to be our sissy maid." She kissed me again. "Yes, Ma'am," I replied, and smiled.