Chapter 1: My cuckold life
I have a small penis. In fact, I have a very small penis. I’ve been in permanent chastity for over 7 years. My wife and her lovers call it my “caged clitty” and that’s about right as far as it being a useful penis.
I suppose I should start at the beginning. I’ve never been much of a man. I’m not very muscular and was never good in sports. I was always picked on by bigger and stronger boys in school and other boys my age frequently called me a “sissy”. As humiliating as it was at the time, it turns out they were right. They could see what I was long before I realized it myself. I wasn’t gay, I liked girls very much. And I never felt attracted to men (back then) although several older men found me attractive. Nothing happened but looking back, I can now see their advances more clearly. What I brushed off as older men being nice, were attempts to get me into their bed. Today, part of me wishes a more dominant man had discovered me when I was a teen. But Iiving in a small town, my life progressed as normal as possible for a weak, passive, male. I graduated from high school and accepted a job as far from home as I could to start a new life. Little did I know, it only allowed me the freedom to become who and what I am now.
I met my wife and she recognized right away that she would be the leader in our relationship. She was gorgeous. At 5’4” and 110 pounds, she was only an inch shorter than me but curvy and voluptuous with blonde hair, blue eyes, a narrow waist, tight round ass, and full 36D breasts. She was completely out my league in my old life back home and I couldn’t understand what she saw in a small, weak man like me. As I was completely inexperienced with women and had never had sex, we made out but never actually had sex until our wedding night where she discovered the full extent of my inadequacy as a man. She had been very sexually active in previous relationships so when we were finally alone and naked on our wedding night, she was shocked and obviously very disappointed with what she found when my underwear came down. We tried to get my little nub to penetrate her but she could barely feel me at her entrance. As I lay shamefully next to her on the bed, she began telling me about how good sex was…with real men. She explained in great detail how her other lovers made her feel like a woman and filled her in a way that we both realized I never could. As she talked about how good it felt to have a large cock stretching her and the deep satisfying joy of orgasms, my tiny clitty became harder than ever before in my life. I was embarrassed and humiliated but she found it amusing at how excited I was. “Look at you! She exclaimed. “I think you like the idea of other men fucking me.” and continued to describe their huge cocks and how good they felt inside her. It didn’t take long before my tiny penis erupted all over myself. It was my first orgasm with another person but as good as it felt, I was deeply ashamed that it happened without entering her. Her soft hand and long manicured fingers spread my meager ejaculation all over my spent clitty and tiny balls. She brought a small pearl of my thin cum to my lips and said, “open”. I did as I was told and she pushed my own salty, pungent cum into my mouth and rubbed it on my tongue. I was stunned but followed her lead, tasting sperm for the first time in my life. She smiled lovingly at me as she mused, “Perhaps, our sex life is salvageable after all”, with a gleam in her eye she said, “Wait here. And don’t get dressed.” I lay in the bed and watched her slip on her lacy white bra and lacy panties that she’d worn for our first time together as man and wife. She slipped on a very short, low-cut dress and a pair of very high stiletto heels. She pecked my forehead and said, “I’ll be back soon” and added more forcefully, “I expect you to be right here, just like this. And don’t you dare wash this off,” she warned me, tracing a nail over the shiny semen smeared and drying on my clitty and balls. With that, she went to the door and just as she was leaving, she turned and said, “When I return, open the door for us, then sit quietly in that chair in the corner.” And then, she was gone. My mind was reeling, “Us?” I thought, but somewhere deep inside, I knew what was coming and I was secretly happy to be told what exactly what to do. She’s a beautiful woman and it didn’t take long to find what she was needed. There was a tap at the door and I obediently answered. There she was with a tall muscular man on her arm. They swept into the room and as I stood there looking down at my feet. My clitty shriveling even smaller in the presence of a real man and my wife. When I glanced at her, she nodded toward the chair in the corner and I went to it and sat down. “I see what you meant,” the man said, noticing my undersized genitals. She took him to the bed and knelt at his feet. She looked at me as she unbuckled his belt, opened his pants and pulled out the biggest cock I’d ever seen in real life. Even flaccid, he was three times bigger than me. She stroked his cock, then leaned forward and sucked it into her mouth. The sight of her red painted lips on his much bigger penis was something I’ll never forget. I panicked as I felt my clitty getting stiff as she expertly sucked him until he was fully erect. He was rock hard with at least 8 inches of throbbing, veiny masculinity. By now his pants were at his ankles as she licked him all over and cupped his huge balls in her delicate hand. She glanced at me with his thick cockhead between her lips. Paused for a moment and said, “See Honey, this is what a real man looks like.” I nodded meekly but all I could do was watch and wish it were me. He undressed her and pushed her onto the bed. I could see her pussy was glistening wet as he rubbed his massive tool up and down my wife’s slippery opening. Her juices coating him as the thick round head entered her. I watched as she opened for him and his cock slid easily into her eager wet pussy. She moaned, and told him, “Yes! Yes! Fuck me! I need this so much!” He fucked her for a long time in long, deep strokes and she obviously loved every second of it. Pulling her legs up high and locking her heels around his waist as he reached places I could never, ever reach. They fucked for a very long time with me watching and dripping pearls of my own pathetic cum from my tiny erect penis. Eventually, their pace became faster and I could tell he was getting ready to cum. “Oh my God,” I thought, “this stranger is about to cum inside my wife.” Something I hadn’t done yet and didn’t realize, I never would. She coaxed him on, “Yes! Cum in me!” she cried pulling him even deeper in her. From where I was sitting, I could see his huge balls contract as he groaned and whispered to her, “here it comes Baby!”. My wife orgasmed wildly as he released in her, pumping jet after jet of his thick cum inside her newly married pussy. My own clitty convulsed and more of my weak juices flowed out me and down my small testicles. She noticed me cuming and told her lover, “Look, he loves watching us together.” The man glanced at the mess I’d made and smirked. “I’m sorry,” he told her, “Not much of a man you have there. More of a sissy. Maybe you should have him wear your panties, he'd make a better girlfriend than a husband.” I could see the idea appealed to her and it was a glimpse of what was yet in store for me. “You may be right Sweetie,” she said, milking more of his cum from his deflating penis with her hungry pussy. He pulled his slippery cum coated penis from her well used hole and rolled on his back. “But first, he must learn how to be a proper sissy husband,” she told him. Looking directly at me, she said, “Honey, put on my panties and come over here.” I reluctantly obeyed, stepping into her lacy white panties, feeling their silkiness on my shriveled balls and shrunken penis. I stood next to the bed as she said, “Come up here and clean your wife’s lover like a good sissy husband.” I knelt on the bed and looked at her. “Go on, do as your told!” She commanded. I reached out for his now flaccid cock. “No”, my wife said sternly. With your mouth. I was stunned and hesitated. “If this marriage is going to work, you’re going to have to do as your told Sweetie,” she told me. “Now, lick my juices off of our lover.” “But…I’m not…” I stuttered. “Yes, of course, you’re not gay. But you are my husband, and you will do as your told. Now lick him clean.” I obediently bent closer to his cock. I could smell his musky cum and the sweet smell of her pussy juices. “Now!” she said, looking me straight in the eye. I knew this was a decision point in our marriage. I would do as she says or she would leave me. I closed my eyes and licked a man’s penis for the first time. It wasn’t terrible. The mixture of their juices was sweet and salty but not as revolting as I thought it would be. I started licking him up and down the shaft, taking care to scoop up the pearls of cum at the base of his cock which was still much thicker than me even when he was soft. I reached the head and ran my tongue around it. Poking my tongue into his pee slit and extracting a huge glob of his cum. “Good.’ She praised. “Now put him in your mouth.” I opened and allowed his cock into my mouth. It was slippery with their cum and my saliva. “Suck it Sweetie,” she said, “just like you saw me doing.” I was ashamed and humiliated but I sucked his cock. I honestly believed I had no choice. I could
feel him growing firmer in my mouth. “That’s it, Baby,” she encouraged me. “Make him hard so he can fuck me again.” I did as she said and before long he was standing erect again. I looked at her with a strange sense of pride. “That’s a good girl.” She said. You’re a very good cocksucker. I wasn’t sure how to feel about being called a girl and a cocksucker but I was happy to please her. “Now, clean me up Sweetie,” she said, laying back and opening her legs wide. I could see her freshly fucked pussy opened wide by his huge cock and glistening with their juices. A large amount of his seed was leaking from her. I moved over and buried my face in my wife sweet pussy. It was so wonderful to finally be able to have any kind of sex with her. I desperately needed to please her. I licked her all over, probing my tongue deep inside and retrieving mouthfuls of his thick cum. She was moaning in pleasure and I was in heaven. Eventually, she pushed me onto my back and straddled my face. He kissed her and fondled her gorgeous breasts, as their cum dripped from her pussy into my eager mouth. I swallowed my first load of a real man’s cum. When they were ready, she sent me back to my chair and they fucked several more times calling me over between sessions to clean them both and get him hard again. When he was finally spent, she led him to the door and kissed him goodbye. After, he had gone, she looked at me and said, “you did very well tonight, Sweetie. I think things are going to work out just fine.” We both crawled into bed and cuddled until she fell asleep. I lay there for the longest time, thinking about what had happened and whether or not I liked it or whether it mattered if I like it or not. I realized then, that I enjoyed giving her pleasure and if this was the only way I could do it, then this is how it must be. I finally fell asleep wondering when, and with who, our next sexual encounter would be. That was seven years ago and my wife has had many lovers in that time. Each time taking my cuckolding a step further. She also began feminizing me but it happened so slowly, I didn’t realize how far it had gone until it was too late. The first major step happened within a month of that first wedding night cuckolding. One day at breakfast she produced a small metallic device and asked me if I knew what it was. I’d never seen a chastity cage before and thought it might be some kitchen utensil since I did all of the cooking and cleaning in our house. We went to the computer and she showed me several photos of men wearing chastity cages. Many of them showed bondage scenes and almost all had the woman in charge. She saw that it immediately aroused me and teased me with it. “You realize, if we put this on, it may never come off…” I was a little worried about that but she added, “it’s not as if you’re ever going to use it, except to pee, and you can do that with it on. Of course, you’ll have to sit like a girl to pee and I love the thought of owning your tiny little thing.” She knew she had me. “Let’s put it on now.” We watched a short video showing how to put it on and how to keep myself clean while wearing it. Within minutes, I was caged. She turned the key with a satisfying grin, slipped the key onto a long silver chain and put it around her neck. The key dangled in her ample cleavage and the sight of it so near and so far made my tiny clitty stiffen in the cage. It was tight but not uncomfortable. She had purchased one of the smallest ones that snuggly encircled my small balls and held what little I had securely inside the small metal framed cage. I thought we were done but she then produced a small metal tube. It was about 2 inches long and slightly curved. “One last thing,” she said as she lubed the tube and placed it at the tip of the cage. She smiled and gripped my cage firmly. There was a hole there which I had assumed was for peeing. She applied pressure, pushing the tube inside my penis! It was a whole new sensation as the cold steel slid inside me. When it was all the way in, there was a small threaded ball on the end that screwed into the tip of the chastity and held it firmly in place. “Don’t you dare remove that without my permission or I will superglue it in place and throw away your key. Is that clear?” she said in a tone I’d learned to obey. “Yes Ma’am” I meekly replied. “OK, I have to get to work. I expect this place to be clean when I get home.” And then she was gone. I normally cleaned the house and took some time out to stroke my tiny penis when she wasn’t there. I learned later that she’d installed nanny cams throughout the house and the chastity was intended to put an end to my secret self-gratification. It took a while to get used to the weight of my chastity and the ever-present tickle of the urethral probe inside my limp penis. But soon enough, I was used to sitting on the toilet and in time, it just became a part of me. On the rare occasions she allowed me out of my cage, it felt strange. I felt naked without it. With very rare exceptions, I’ve been locked in permanent chastity since that day. Which brings us to today. A few months earlier, she had met a man on-line. But this one turned out to be much different than the others. She dated him several times and always came home with her pussy very stretched and overflowing with cum. She told me how he was the biggest and the best lover she had ever had in her life as I licked his still fresh cum from her freshly fucked pussy. I made a huge mess in my panties as I cleaned her thoroughly. “He must be at least 10 inches Sweetie,” she said dreamily as I struggled to swallow all of his seed. “But you’ll find out soon enough, he’s coming over this weekend. I want the house sparkling and be sure to wear your prettiest pink panties when you greet him at the door.” I nodded my muffled agreement into her saturated and swollen pussy. On Friday night, I had cleaned thoroughly. As my wife dressed, I prepared snacks and drinks, then slipped on my pink panties and waited nervously for him to arrive. Over the years, she normally when out to meet her lovers, leaving me home to think about what she was doing. Sometimes she called while they were having sex or sent me a text of his hard cock in her sweet mouth. So tonight was different and special and I was a little worried why. I always feared she might meet a man she liked better than me but she always reassured me that she loved having me at home while she had sex with real men. Right on time, the doorbell rang and I promptly answered. There in the doorway was the biggest, blackest man I had ever seen. He was easily 6’4” and had 100 pounds on me. He smiled and said, “Hello Sissy, I’m Jamal. I believe your wife is expecting me?” “Y…Yes, Sir.” I stammered stepping back to let him in. I was immediately emasculated and embarrassed to be standing before this Black stranger in nothing but a pair of pretty pink panties. He stepped in, reached over and cupped my tiny silky package with his huge black hand, and looked me in the eye. “Very cute,” he smiled, squeezing my tiny balls and shaking my caged clitty. “I think we’re going to have a lot of fun together.” I blushed and could only say meekly, “Yes Sir.” He came in a sat down as I regained my composure. “Would you like something to drink Sir,” I asked submissively. “Yes, please. How about a whiskey and coke?” Happy to have something to do, I said, “Yes Sir,” and practically curtsied before slinking off to the kitchen. My wife came in and greeted him with a long, wet kiss. “I see you two have met,” she smiled at me, knowing I was completely in shock. “Yes.” Jamal answered glancing at me. You didn’t tell me she was so cute. “I look forward to breaking her in.” Another shock to my already frazzled system! “Breaking her in?” I thought of all the things that could mean, as I served his drink and brought my wife her favorite wine. “Yes,” she said matter-of-factly. “She been a wonderful housewife, but It’s time she learned what it feels like to be a woman.” I couldn’t believe they were talking about me! It was frightening, and yet, my clitty had been fully engorged in my cage from the moment he had squeezed me with his huge hand. I had no idea that my wife had been secretly slipping me female hormones every morning and calling them vitamins. I’d noticed my nipples were larger, darker and almost always erect. My breasts seemed larger and were always tender, my skin was softer, and my clitty rarely grew hard any more, but I never put all those things together. But standing there in my panties, listening to my wife and her huge Black lover discuss “breaking be in” brought me to the verge of tears. I was an emotional wreck but also very excited at a level deep inside that I couldn’t quite understand. My wife sat next to him as I stood out of the way but nearby in case they needed anything. They kissed for a while as she ran her hand over the prominent bulge in his pants. Eventually, they paused and he looked me up and down for an uncomfortably long time. His gaze penetrated me and it wasn't like a man looks at another man. He studied my body as a man would look at a woman. He turned to her and said, "she has nice little boobies doesn't she"? My wife agreed. "Yes, like a teen girl about to blossom". I squirmed under their attention. He noted, "What she needs is a pretty bra and some makeup to go with those panties". "Yes, she does, my wife agreed". "Honey, go put on one of my bras and some of my pink lipstick." She commanded. I hesitated but knew from her eyes, it wasn't a suggestion. I went to her lingerie drawer but all of her bras were much too big for my tiny breasts. I finally found one of her pink spandex workout tops that fit me. It hugged my budding teen breasts. I then went to her make-up table and found some bright pink lipstick. I applied it the best I knew how. I glanced in the mirror and couldn't believe how much bigger my boobs seemed in the form fitting top. My sensitive nipples were erect and visibly pronounced through the fabric. She had me grow my hair out for the past year so with my shoulder length hair, full pouty pink lips, and the pretty pink undergarments, I looked more like a girl than ever before. My legs and arms were slender and hairless. My face even looked soft and feminine. I brushed out my hair and stood there admiring myself. I brushed my nipples with my long, manicured nails and felt a thrill throughout my body and even felt something stir in my cage for the first time in a long time. I knew I had to get back before they missed me or worse yet, I might make a wet spot in my panties! As I returned to the living room, I found my wife naked and her lover in his boxers. His huge hand cupped her beautiful full white breast which I had never held in seven years of marriage. Her nipples were taut and erect as she ran her hands over his muscular chest and kissed him deeply. When they finally noticed me, Jamal said, "Now that's more like it!" My wife said, "Oh my goodness Sweetie, you look adorable!" I looked at the floor in a mixture of shame and pride. "Thank you", I whispered, sounding like a little girl wearing her first Sunday dress. He stood up and took her hand, leading her to the bedroom, I couldn't help but stare at the enormous bulge in his shorts. He caught me looking and said, "Don't worry Sissy, there's enough here for both of you..." Again, I felt my clitty swell against the steel bars of my cage as the meaning of his comment swirled through my brain. I was completely conditioned to clean men's cum from my wife, clean her lover’s spent cocks, and even suck them until they were ready to fuck her again. But this was a whole new level. Does he want to fuck me with the monster straining at his underwear? Early in my chastity, my wife read on-line that Sissies need to be relieved of their pent-up semen to maintain good prostate health. She began monthly “milkings" where I knelt on all fours and she inserted a rubber gloved finger into my anus. By pressing down on my prostate with her long slender finger, my watery sperm would release into a bowl on the floor. The first time she did it, I exploded like never before in my life! Releasing a large amount of cum. I didn't orgasm but it felt so wonderful to cum at all and even better to please her. Soon she was using two fingers, then three. These days, she uses a realistic dildo to extract my juices. Of course, each time she makes me lick the bowl clean and gets very upset if I spill a single drop. For years now, she's referred to my ass as my "pussy" and I very much look forward to my monthly milking. His comment gave me a tingly feeling in my pussy wondering if I was really going to lose my anal virginity to this gigantic Black man. I was terrified and excited at the same time. I stood motionless as they headed toward our bedroom. "Bring her along too", he said to my wife. "Do as he says, Sweetie, from now on you will obey him as you would me." I followed obediently and stood in the corner of the bedroom as he led her to our bed. She dropped to her knees in front of him and he looked at me and turned so I had a direct view of what was about to happen. As she pulled down his shorts, I could see his thick black shaft appear. It was huge! And incredibly thick. As if in slow motion, more of his shaft appeared as the shorts inched lower. It just kept going! She had already pulled them down 8 inches and no end in sight. By the time his shorts reached his knees, the fat round head popped out and his entire length swung outward toward her face. It was gigantic! The biggest cock I'd ever seen, even on the internet or porn movies. My wife hadn't exaggerated, it was at least ten inches long. It was literally as thick and as long as my forearm and wasn’t even fully erect! There were huge veins running the full length of his shaft ending in a cocoa-colored baseball sized head. She stroked him with both hands, mesmerized by it. She opened her mouth and encircled the fat tip with her lips. She could barely fit the huge head in her tiny mouth but she greedily sucked and licked it all over. She glanced at me with the tip in her mouth and I knew she was thinking, "This is a real cock, Honey." I couldn't imagine how his enormous cock could fit in my tiny wife. It would reach all the way up into her ribcage! I was about to find out. After ten minutes of her loving attention, he stood fully erect and ready for my wife's tight sweet pussy. He lifted her easily to her feet and pushed her back onto the bed. His long hard Black cock pointed at her sopping wet slit. I stood there in my lingerie, staring helplessly. Lost in a whirlwind of emotions. I was pulled back by his firm command. "Get over here Sissy." You need to see this up close. "Kneel between my legs and watch me fuck your wife. You need to know who owns this pussy now." I scurried over and knelt obediently behind him. The view was overwhelming. His huge, goose egg size balls were directly in my face but I could still see his cock poised at her entrance. "Hold my balls, Sissy." He commanded. I reached out and cupped his heavy balls, imagining how much of his superior cum must be stored in there and would soon fill my wife. At that moment, I realized I’d already swallowed massive amounts of his seed over the couple of months not knowing my wife was seeing this huge Black man. My stomach rumbled and mouth watered at the thought of swallowing even more of it today. This time fresh from the source. I cupped his heavy balls in my hands, each one completely filling my palm. I gently kneaded them, marveling at their size and weight. I watched as his massive head parted her wet lips. She opened easily for him allowing the thick head inside her. He kept pushing, as his shaft slowly sank into her. Stretching her wider and wider with each thick inch. Her pussy was stretched wider and fuller than I had ever seen it. Her pussy lips gripped his impossibly huge shaft as she stretched further and further to accept him. I could hear her moaning in ecstasy the deeper he went. How could something so big fit inside her? I wondered dreading the thought of him ripping my own pussy wide open with his enormous cock. But he kept going until the entire length and width of it was buried inside her. I held his massive balls as he hit bottom and pulled back slowly. It was an incredible sight. I mentally searched for my clitty but found no trace of it. It always retreated inside me, soft and limp whenever I was in the presence of a real man. And this was a real Black man with a gigantic Black cock buried in my tiny white wife. I could feel my nipples, fully erect and pushing against the fabric of my bra and realized how good and right it felt to have my breasts and nipples supported in a bra. He fucked her for the longest time with me supporting his heavy balls as he thrust in and out of her. Her pussy obviously had adjusted to his size over the past month because she met each of his thrusts even as he pulled her legs over his shoulders and pounded her ruined pussy deeper and faster. It seemed like an hour before he grunted and his balls tightened in my hands. "Here it comes Baby!" He hissed as she cried out, "Yes! Yes! Fill me with your seed! Give me your Black baby". I was shocked at the "baby" part - I'd never considered she would get pregnant. At least, I assumed she was on birth control but later learned he'd made her stop the first time he fucked her. His balls contracted in my hands as he commanded me, "Squeeze them, Sissy! Fill your wife with my baby juice!" This time I felt my clitty drip as I squeezed his balls, feeling them crinkle and spasm as his cum flowed into her. She must have orgasmed ten times on his hard black cock. He filled her so much that it oozed out around his shaft as he continued to pump his black seed deep into her fertile white womb. Eventually he slowed and pulled his still massive cock from her cum filled pussy. Thick white globs poured from her sloppy hole. Her pussy lips were swollen and distended and she remained open and gaping even after he pulled out. As he rolled on his back, I knew what I was expected to do. I crawled onto the bed and began licking him clean. By now, I loved the taste of fresh cum and eagerly licked every drop from his softening but still huge black cock. “That’s a good girl, Sissy,” her lover sighed as I went to work. I could barely fit my hand around his girth as I guided the head into my mouth. Even more cum emerged into my mouth as I stroked his shaft and sucked the head. Probing his pee slit with my tongue. When I was sure he was completely clean, I turned my attention to my wife. I couldn't believe how much thick, salty sperm he had deposited inside her. It just kept leaking out into my mouth as I swallowed as fast as I could. My wife orgasmed again as I cleaned her making me so proud to please her. I looked up at my wife. Her smile beamed as she said, "You have some on your chin Sweetie," I scooped it into my mouth, swallowed, and smiled sheepishly at her. "Good girl," she complimented as I buried my face between her legs again. Just as she pushed a giant glob of his cum onto my tongue, I felt my panties being pulled down. I swallowed my mouthful of fresh cum as I glanced over my shoulder. Her lover was kneeling behind me with a tube of lube in one hand and one of his large fingers circling my smooth pink anus ring. I knew I couldn’t refuse him and nervously went back to licking my wife’s still cummy pussy. I could feel him apply cold, slippery gel to my pussy and then felt his thick finger pushing into me. His single digit was bigger than my milking dildo and stretched my pussy as it slipped past my tight anal ring. It felt strange and wonderful to have something alive inside me. He pressed it in further. I felt his knuckle enter and he kept going deeper. Soon he was sliding his whole finger deeply in and out of me. I could barely concentrate on licking my wife as he fucked my pussy with his huge finger. Eventually, he pressed downward and found my prostate. I discharged violently, spilling everything I had onto the bedspread. I tried to jump up and clean up my mess but he grabbed my tiny caged package firmly and held me in place. With two large fingers he pinched my balls at the base and used them as a tether as he continued to fuck my ass-pussy with his other hand. “You ain’t going nowhere, Sissy,” he said. With that he inserted a second slippery finger in my ass. Oh my God! His two fingers stretched me to the limit! “There you go Baby girl,” he said, “Just relax and enjoy it.” I tried to relax but each deep thrust brought such incredible feelings. By now, I had stopped licking my wife. When I realized it, I looked at her. She was thoroughly enjoying the sight of me impaled on his long, thick, Black fingers. “It feels good, doesn’t it Sweetie?” she asked. I just moaned and closed my eyes. It did feel good, so very good. I went down on my elbows and raised my ass for him. “Oh yeah, she likes it a lot.” Jamal said. “Just wait until she feels me inside her.” He added. With that, I wiggled my ass in agreement. This was the most pleasure I’d been allowed in our entire marriage. He added some more lube and slowly pressed a third finger into me. If I thought two was large, three fingers was overwhelming! He gently probed me for a long time before withdrawing his fingers. My ass felt so empty. But soon, I felt him at my anal entrance again. Only this time, it was the head of his enormous Black Cock! I tried to pull away but between him pressing down on my butt with his huge hand and my wife placing her hands on my shoulders, I was trapped. I glanced at my wife in panic. “Don’t worry, Sweetie,” she soothed, “I thought it was too big at first, but you’ll learn to love it soon enough.” Jamal instructed me, “Just relax and open your pussy for Daddy,” he said. Again, I tried to relax. Focusing on my flexing my anal ring for him. He could feel my tight ring “kissing” the head of his cock. “That’s it little girl,” he said. “Your pussy is mine too.” With that, I felt his head stretching me wide. It hurt so much! "He’s too big!, I thought, "It will never fit!” My mind shouted at me but my body was working hard to let him in. I rotated my hips and tried to open as wide as I could. It felt like a baseball bat was being pushed inside me. With a sudden “pop”, his giant head slipped past my anal ring. The pressure seemed to lessen but I was still stretched impossibly wide. He pushed a few inches further into me, then withdrew. Popping back through my abused ring. His cockhead nuzzled my opening and pushed back in. Then popped back out. He kept this up for the longest time. Popping in and out of me. I didn’t know, but he’d broken in many tight white wives and sissies. He was expertly conditioning my pussy to accept him. After an eternity of being impaled over and over again. He pulled out. “That’s enough for today, Sissy,” he said, slapping me ass hard. “Go get us something to drink while I fuck your sweet wife again.” I gingerly slipped off the bed and headed for the kitchen. I loved how feminine I felt as I walked through the house with my loose, wet pussy. It was sore but I was so happy he stopped before he damaged me. Jamal fucked my wife three more times that night as I stood by, serving them refreshments, and of course, cleaning his never-ending supply of cum from his cock and her overflowing pussy. I could feel my stretched pussy and wondered at how my wife could take all of him over and over again. By morning, they were fast asleep and my tummy was completely full of his cum. The next day, as I served her a very late breakfast, my wife was radiant and kept teasing me about being a real woman now. “I just knew you and Jamal would hit it off,” she said. “He's such a strong and powerful man. Just what we need, don’t you agree Sweetie?” “Yes Ma’am,” I agreed. “But he’s so big!” I complained mildly. “Oh yes!” she agreed. “So wonderfully big. He fills me so completely. I’m a little tender down there, but I suppose you understand that, don’t you Baby?” she smiled. “Don’t worry, you’ll adjust to his size. It took me a week to finally take all of him, but oh my God! It’s so worth it!” “You’ll be taking all of him too and we have plenty of time to break you in, the three of us are going on a cruise!” I was surprised and taken aback by the thought of the three of us going out in public together for any length of time. “We leave next Saturday, so while I’m at work this week, you need to pack our bags. Be sure to pack my sexiest and most revealing outfits. We’ll all be in the same cabin and I want everyone to know exactly what’s going on in there.” I could see she was excited at being with him for an entire week but also looking forward taking my cuckold status to the next level. On Monday, she brought home a large black dildo. It wasn't as big as Jamal but she instructed me to practice on it for at least three hours every day. “You need to stretch your mouth and ass-pussy if you expect to properly please our new Black Daddy, Baby.” She said. “And by the way, I had to suck off the Black man at the sex shop to get a discount. He wasn't nearly as big as Jamal, but he fit in my mouth and shot a lovely load of cum straight down my throat.” She kissed me and I could taste his cum on her breath. I did as she said, and spent the next week packing our bags and nervously preparing my mouth and pussy for the cruise.
Chapter 2: Cuckold Cruise
I suppose I should start at the beginning. I’ve never been much of a man. I’m not very muscular and was never good in sports. I was always picked on by bigger and stronger boys in school and other boys my age frequently called me a “sissy”. As humiliating as it was at the time, it turns out they were right. They could see what I was long before I realized it myself. I wasn’t gay, I liked girls very much. And I never felt attracted to men (back then) although several older men found me attractive. Nothing happened but looking back, I can now see their advances more clearly. What I brushed off as older men being nice, were attempts to get me into their bed. Today, part of me wishes a more dominant man had discovered me when I was a teen. But Iiving in a small town, my life progressed as normal as possible for a weak, passive, male. I graduated from high school and accepted a job as far from home as I could to start a new life. Little did I know, it only allowed me the freedom to become who and what I am now.
I met my wife and she recognized right away that she would be the leader in our relationship. She was gorgeous. At 5’4” and 110 pounds, she was only an inch shorter than me but curvy and voluptuous with blonde hair, blue eyes, a narrow waist, tight round ass, and full 36D breasts. She was completely out my league in my old life back home and I couldn’t understand what she saw in a small, weak man like me. As I was completely inexperienced with women and had never had sex, we made out but never actually had sex until our wedding night where she discovered the full extent of my inadequacy as a man. She had been very sexually active in previous relationships so when we were finally alone and naked on our wedding night, she was shocked and obviously very disappointed with what she found when my underwear came down. We tried to get my little nub to penetrate her but she could barely feel me at her entrance. As I lay shamefully next to her on the bed, she began telling me about how good sex was…with real men. She explained in great detail how her other lovers made her feel like a woman and filled her in a way that we both realized I never could. As she talked about how good it felt to have a large cock stretching her and the deep satisfying joy of orgasms, my tiny clitty became harder than ever before in my life. I was embarrassed and humiliated but she found it amusing at how excited I was. “Look at you! She exclaimed. “I think you like the idea of other men fucking me.” and continued to describe their huge cocks and how good they felt inside her. It didn’t take long before my tiny penis erupted all over myself. It was my first orgasm with another person but as good as it felt, I was deeply ashamed that it happened without entering her. Her soft hand and long manicured fingers spread my meager ejaculation all over my spent clitty and tiny balls. She brought a small pearl of my thin cum to my lips and said, “open”. I did as I was told and she pushed my own salty, pungent cum into my mouth and rubbed it on my tongue. I was stunned but followed her lead, tasting sperm for the first time in my life. She smiled lovingly at me as she mused, “Perhaps, our sex life is salvageable after all”, with a gleam in her eye she said, “Wait here. And don’t get dressed.” I lay in the bed and watched her slip on her lacy white bra and lacy panties that she’d worn for our first time together as man and wife. She slipped on a very short, low-cut dress and a pair of very high stiletto heels. She pecked my forehead and said, “I’ll be back soon” and added more forcefully, “I expect you to be right here, just like this. And don’t you dare wash this off,” she warned me, tracing a nail over the shiny semen smeared and drying on my clitty and balls. With that, she went to the door and just as she was leaving, she turned and said, “When I return, open the door for us, then sit quietly in that chair in the corner.” And then, she was gone. My mind was reeling, “Us?” I thought, but somewhere deep inside, I knew what was coming and I was secretly happy to be told what exactly what to do. She’s a beautiful woman and it didn’t take long to find what she was needed. There was a tap at the door and I obediently answered. There she was with a tall muscular man on her arm. They swept into the room and as I stood there looking down at my feet. My clitty shriveling even smaller in the presence of a real man and my wife. When I glanced at her, she nodded toward the chair in the corner and I went to it and sat down. “I see what you meant,” the man said, noticing my undersized genitals. She took him to the bed and knelt at his feet. She looked at me as she unbuckled his belt, opened his pants and pulled out the biggest cock I’d ever seen in real life. Even flaccid, he was three times bigger than me. She stroked his cock, then leaned forward and sucked it into her mouth. The sight of her red painted lips on his much bigger penis was something I’ll never forget. I panicked as I felt my clitty getting stiff as she expertly sucked him until he was fully erect. He was rock hard with at least 8 inches of throbbing, veiny masculinity. By now his pants were at his ankles as she licked him all over and cupped his huge balls in her delicate hand. She glanced at me with his thick cockhead between her lips. Paused for a moment and said, “See Honey, this is what a real man looks like.” I nodded meekly but all I could do was watch and wish it were me. He undressed her and pushed her onto the bed. I could see her pussy was glistening wet as he rubbed his massive tool up and down my wife’s slippery opening. Her juices coating him as the thick round head entered her. I watched as she opened for him and his cock slid easily into her eager wet pussy. She moaned, and told him, “Yes! Yes! Fuck me! I need this so much!” He fucked her for a long time in long, deep strokes and she obviously loved every second of it. Pulling her legs up high and locking her heels around his waist as he reached places I could never, ever reach. They fucked for a very long time with me watching and dripping pearls of my own pathetic cum from my tiny erect penis. Eventually, their pace became faster and I could tell he was getting ready to cum. “Oh my God,” I thought, “this stranger is about to cum inside my wife.” Something I hadn’t done yet and didn’t realize, I never would. She coaxed him on, “Yes! Cum in me!” she cried pulling him even deeper in her. From where I was sitting, I could see his huge balls contract as he groaned and whispered to her, “here it comes Baby!”. My wife orgasmed wildly as he released in her, pumping jet after jet of his thick cum inside her newly married pussy. My own clitty convulsed and more of my weak juices flowed out me and down my small testicles. She noticed me cuming and told her lover, “Look, he loves watching us together.” The man glanced at the mess I’d made and smirked. “I’m sorry,” he told her, “Not much of a man you have there. More of a sissy. Maybe you should have him wear your panties, he'd make a better girlfriend than a husband.” I could see the idea appealed to her and it was a glimpse of what was yet in store for me. “You may be right Sweetie,” she said, milking more of his cum from his deflating penis with her hungry pussy. He pulled his slippery cum coated penis from her well used hole and rolled on his back. “But first, he must learn how to be a proper sissy husband,” she told him. Looking directly at me, she said, “Honey, put on my panties and come over here.” I reluctantly obeyed, stepping into her lacy white panties, feeling their silkiness on my shriveled balls and shrunken penis. I stood next to the bed as she said, “Come up here and clean your wife’s lover like a good sissy husband.” I knelt on the bed and looked at her. “Go on, do as your told!” She commanded. I reached out for his now flaccid cock. “No”, my wife said sternly. With your mouth. I was stunned and hesitated. “If this marriage is going to work, you’re going to have to do as your told Sweetie,” she told me. “Now, lick my juices off of our lover.” “But…I’m not…” I stuttered. “Yes, of course, you’re not gay. But you are my husband, and you will do as your told. Now lick him clean.” I obediently bent closer to his cock. I could smell his musky cum and the sweet smell of her pussy juices. “Now!” she said, looking me straight in the eye. I knew this was a decision point in our marriage. I would do as she says or she would leave me. I closed my eyes and licked a man’s penis for the first time. It wasn’t terrible. The mixture of their juices was sweet and salty but not as revolting as I thought it would be. I started licking him up and down the shaft, taking care to scoop up the pearls of cum at the base of his cock which was still much thicker than me even when he was soft. I reached the head and ran my tongue around it. Poking my tongue into his pee slit and extracting a huge glob of his cum. “Good.’ She praised. “Now put him in your mouth.” I opened and allowed his cock into my mouth. It was slippery with their cum and my saliva. “Suck it Sweetie,” she said, “just like you saw me doing.” I was ashamed and humiliated but I sucked his cock. I honestly believed I had no choice. I could
feel him growing firmer in my mouth. “That’s it, Baby,” she encouraged me. “Make him hard so he can fuck me again.” I did as she said and before long he was standing erect again. I looked at her with a strange sense of pride. “That’s a good girl.” She said. You’re a very good cocksucker. I wasn’t sure how to feel about being called a girl and a cocksucker but I was happy to please her. “Now, clean me up Sweetie,” she said, laying back and opening her legs wide. I could see her freshly fucked pussy opened wide by his huge cock and glistening with their juices. A large amount of his seed was leaking from her. I moved over and buried my face in my wife sweet pussy. It was so wonderful to finally be able to have any kind of sex with her. I desperately needed to please her. I licked her all over, probing my tongue deep inside and retrieving mouthfuls of his thick cum. She was moaning in pleasure and I was in heaven. Eventually, she pushed me onto my back and straddled my face. He kissed her and fondled her gorgeous breasts, as their cum dripped from her pussy into my eager mouth. I swallowed my first load of a real man’s cum. When they were ready, she sent me back to my chair and they fucked several more times calling me over between sessions to clean them both and get him hard again. When he was finally spent, she led him to the door and kissed him goodbye. After, he had gone, she looked at me and said, “you did very well tonight, Sweetie. I think things are going to work out just fine.” We both crawled into bed and cuddled until she fell asleep. I lay there for the longest time, thinking about what had happened and whether or not I liked it or whether it mattered if I like it or not. I realized then, that I enjoyed giving her pleasure and if this was the only way I could do it, then this is how it must be. I finally fell asleep wondering when, and with who, our next sexual encounter would be. That was seven years ago and my wife has had many lovers in that time. Each time taking my cuckolding a step further. She also began feminizing me but it happened so slowly, I didn’t realize how far it had gone until it was too late. The first major step happened within a month of that first wedding night cuckolding. One day at breakfast she produced a small metallic device and asked me if I knew what it was. I’d never seen a chastity cage before and thought it might be some kitchen utensil since I did all of the cooking and cleaning in our house. We went to the computer and she showed me several photos of men wearing chastity cages. Many of them showed bondage scenes and almost all had the woman in charge. She saw that it immediately aroused me and teased me with it. “You realize, if we put this on, it may never come off…” I was a little worried about that but she added, “it’s not as if you’re ever going to use it, except to pee, and you can do that with it on. Of course, you’ll have to sit like a girl to pee and I love the thought of owning your tiny little thing.” She knew she had me. “Let’s put it on now.” We watched a short video showing how to put it on and how to keep myself clean while wearing it. Within minutes, I was caged. She turned the key with a satisfying grin, slipped the key onto a long silver chain and put it around her neck. The key dangled in her ample cleavage and the sight of it so near and so far made my tiny clitty stiffen in the cage. It was tight but not uncomfortable. She had purchased one of the smallest ones that snuggly encircled my small balls and held what little I had securely inside the small metal framed cage. I thought we were done but she then produced a small metal tube. It was about 2 inches long and slightly curved. “One last thing,” she said as she lubed the tube and placed it at the tip of the cage. She smiled and gripped my cage firmly. There was a hole there which I had assumed was for peeing. She applied pressure, pushing the tube inside my penis! It was a whole new sensation as the cold steel slid inside me. When it was all the way in, there was a small threaded ball on the end that screwed into the tip of the chastity and held it firmly in place. “Don’t you dare remove that without my permission or I will superglue it in place and throw away your key. Is that clear?” she said in a tone I’d learned to obey. “Yes Ma’am” I meekly replied. “OK, I have to get to work. I expect this place to be clean when I get home.” And then she was gone. I normally cleaned the house and took some time out to stroke my tiny penis when she wasn’t there. I learned later that she’d installed nanny cams throughout the house and the chastity was intended to put an end to my secret self-gratification. It took a while to get used to the weight of my chastity and the ever-present tickle of the urethral probe inside my limp penis. But soon enough, I was used to sitting on the toilet and in time, it just became a part of me. On the rare occasions she allowed me out of my cage, it felt strange. I felt naked without it. With very rare exceptions, I’ve been locked in permanent chastity since that day. Which brings us to today. A few months earlier, she had met a man on-line. But this one turned out to be much different than the others. She dated him several times and always came home with her pussy very stretched and overflowing with cum. She told me how he was the biggest and the best lover she had ever had in her life as I licked his still fresh cum from her freshly fucked pussy. I made a huge mess in my panties as I cleaned her thoroughly. “He must be at least 10 inches Sweetie,” she said dreamily as I struggled to swallow all of his seed. “But you’ll find out soon enough, he’s coming over this weekend. I want the house sparkling and be sure to wear your prettiest pink panties when you greet him at the door.” I nodded my muffled agreement into her saturated and swollen pussy. On Friday night, I had cleaned thoroughly. As my wife dressed, I prepared snacks and drinks, then slipped on my pink panties and waited nervously for him to arrive. Over the years, she normally when out to meet her lovers, leaving me home to think about what she was doing. Sometimes she called while they were having sex or sent me a text of his hard cock in her sweet mouth. So tonight was different and special and I was a little worried why. I always feared she might meet a man she liked better than me but she always reassured me that she loved having me at home while she had sex with real men. Right on time, the doorbell rang and I promptly answered. There in the doorway was the biggest, blackest man I had ever seen. He was easily 6’4” and had 100 pounds on me. He smiled and said, “Hello Sissy, I’m Jamal. I believe your wife is expecting me?” “Y…Yes, Sir.” I stammered stepping back to let him in. I was immediately emasculated and embarrassed to be standing before this Black stranger in nothing but a pair of pretty pink panties. He stepped in, reached over and cupped my tiny silky package with his huge black hand, and looked me in the eye. “Very cute,” he smiled, squeezing my tiny balls and shaking my caged clitty. “I think we’re going to have a lot of fun together.” I blushed and could only say meekly, “Yes Sir.” He came in a sat down as I regained my composure. “Would you like something to drink Sir,” I asked submissively. “Yes, please. How about a whiskey and coke?” Happy to have something to do, I said, “Yes Sir,” and practically curtsied before slinking off to the kitchen. My wife came in and greeted him with a long, wet kiss. “I see you two have met,” she smiled at me, knowing I was completely in shock. “Yes.” Jamal answered glancing at me. You didn’t tell me she was so cute. “I look forward to breaking her in.” Another shock to my already frazzled system! “Breaking her in?” I thought of all the things that could mean, as I served his drink and brought my wife her favorite wine. “Yes,” she said matter-of-factly. “She been a wonderful housewife, but It’s time she learned what it feels like to be a woman.” I couldn’t believe they were talking about me! It was frightening, and yet, my clitty had been fully engorged in my cage from the moment he had squeezed me with his huge hand. I had no idea that my wife had been secretly slipping me female hormones every morning and calling them vitamins. I’d noticed my nipples were larger, darker and almost always erect. My breasts seemed larger and were always tender, my skin was softer, and my clitty rarely grew hard any more, but I never put all those things together. But standing there in my panties, listening to my wife and her huge Black lover discuss “breaking be in” brought me to the verge of tears. I was an emotional wreck but also very excited at a level deep inside that I couldn’t quite understand. My wife sat next to him as I stood out of the way but nearby in case they needed anything. They kissed for a while as she ran her hand over the prominent bulge in his pants. Eventually, they paused and he looked me up and down for an uncomfortably long time. His gaze penetrated me and it wasn't like a man looks at another man. He studied my body as a man would look at a woman. He turned to her and said, "she has nice little boobies doesn't she"? My wife agreed. "Yes, like a teen girl about to blossom". I squirmed under their attention. He noted, "What she needs is a pretty bra and some makeup to go with those panties". "Yes, she does, my wife agreed". "Honey, go put on one of my bras and some of my pink lipstick." She commanded. I hesitated but knew from her eyes, it wasn't a suggestion. I went to her lingerie drawer but all of her bras were much too big for my tiny breasts. I finally found one of her pink spandex workout tops that fit me. It hugged my budding teen breasts. I then went to her make-up table and found some bright pink lipstick. I applied it the best I knew how. I glanced in the mirror and couldn't believe how much bigger my boobs seemed in the form fitting top. My sensitive nipples were erect and visibly pronounced through the fabric. She had me grow my hair out for the past year so with my shoulder length hair, full pouty pink lips, and the pretty pink undergarments, I looked more like a girl than ever before. My legs and arms were slender and hairless. My face even looked soft and feminine. I brushed out my hair and stood there admiring myself. I brushed my nipples with my long, manicured nails and felt a thrill throughout my body and even felt something stir in my cage for the first time in a long time. I knew I had to get back before they missed me or worse yet, I might make a wet spot in my panties! As I returned to the living room, I found my wife naked and her lover in his boxers. His huge hand cupped her beautiful full white breast which I had never held in seven years of marriage. Her nipples were taut and erect as she ran her hands over his muscular chest and kissed him deeply. When they finally noticed me, Jamal said, "Now that's more like it!" My wife said, "Oh my goodness Sweetie, you look adorable!" I looked at the floor in a mixture of shame and pride. "Thank you", I whispered, sounding like a little girl wearing her first Sunday dress. He stood up and took her hand, leading her to the bedroom, I couldn't help but stare at the enormous bulge in his shorts. He caught me looking and said, "Don't worry Sissy, there's enough here for both of you..." Again, I felt my clitty swell against the steel bars of my cage as the meaning of his comment swirled through my brain. I was completely conditioned to clean men's cum from my wife, clean her lover’s spent cocks, and even suck them until they were ready to fuck her again. But this was a whole new level. Does he want to fuck me with the monster straining at his underwear? Early in my chastity, my wife read on-line that Sissies need to be relieved of their pent-up semen to maintain good prostate health. She began monthly “milkings" where I knelt on all fours and she inserted a rubber gloved finger into my anus. By pressing down on my prostate with her long slender finger, my watery sperm would release into a bowl on the floor. The first time she did it, I exploded like never before in my life! Releasing a large amount of cum. I didn't orgasm but it felt so wonderful to cum at all and even better to please her. Soon she was using two fingers, then three. These days, she uses a realistic dildo to extract my juices. Of course, each time she makes me lick the bowl clean and gets very upset if I spill a single drop. For years now, she's referred to my ass as my "pussy" and I very much look forward to my monthly milking. His comment gave me a tingly feeling in my pussy wondering if I was really going to lose my anal virginity to this gigantic Black man. I was terrified and excited at the same time. I stood motionless as they headed toward our bedroom. "Bring her along too", he said to my wife. "Do as he says, Sweetie, from now on you will obey him as you would me." I followed obediently and stood in the corner of the bedroom as he led her to our bed. She dropped to her knees in front of him and he looked at me and turned so I had a direct view of what was about to happen. As she pulled down his shorts, I could see his thick black shaft appear. It was huge! And incredibly thick. As if in slow motion, more of his shaft appeared as the shorts inched lower. It just kept going! She had already pulled them down 8 inches and no end in sight. By the time his shorts reached his knees, the fat round head popped out and his entire length swung outward toward her face. It was gigantic! The biggest cock I'd ever seen, even on the internet or porn movies. My wife hadn't exaggerated, it was at least ten inches long. It was literally as thick and as long as my forearm and wasn’t even fully erect! There were huge veins running the full length of his shaft ending in a cocoa-colored baseball sized head. She stroked him with both hands, mesmerized by it. She opened her mouth and encircled the fat tip with her lips. She could barely fit the huge head in her tiny mouth but she greedily sucked and licked it all over. She glanced at me with the tip in her mouth and I knew she was thinking, "This is a real cock, Honey." I couldn't imagine how his enormous cock could fit in my tiny wife. It would reach all the way up into her ribcage! I was about to find out. After ten minutes of her loving attention, he stood fully erect and ready for my wife's tight sweet pussy. He lifted her easily to her feet and pushed her back onto the bed. His long hard Black cock pointed at her sopping wet slit. I stood there in my lingerie, staring helplessly. Lost in a whirlwind of emotions. I was pulled back by his firm command. "Get over here Sissy." You need to see this up close. "Kneel between my legs and watch me fuck your wife. You need to know who owns this pussy now." I scurried over and knelt obediently behind him. The view was overwhelming. His huge, goose egg size balls were directly in my face but I could still see his cock poised at her entrance. "Hold my balls, Sissy." He commanded. I reached out and cupped his heavy balls, imagining how much of his superior cum must be stored in there and would soon fill my wife. At that moment, I realized I’d already swallowed massive amounts of his seed over the couple of months not knowing my wife was seeing this huge Black man. My stomach rumbled and mouth watered at the thought of swallowing even more of it today. This time fresh from the source. I cupped his heavy balls in my hands, each one completely filling my palm. I gently kneaded them, marveling at their size and weight. I watched as his massive head parted her wet lips. She opened easily for him allowing the thick head inside her. He kept pushing, as his shaft slowly sank into her. Stretching her wider and wider with each thick inch. Her pussy was stretched wider and fuller than I had ever seen it. Her pussy lips gripped his impossibly huge shaft as she stretched further and further to accept him. I could hear her moaning in ecstasy the deeper he went. How could something so big fit inside her? I wondered dreading the thought of him ripping my own pussy wide open with his enormous cock. But he kept going until the entire length and width of it was buried inside her. I held his massive balls as he hit bottom and pulled back slowly. It was an incredible sight. I mentally searched for my clitty but found no trace of it. It always retreated inside me, soft and limp whenever I was in the presence of a real man. And this was a real Black man with a gigantic Black cock buried in my tiny white wife. I could feel my nipples, fully erect and pushing against the fabric of my bra and realized how good and right it felt to have my breasts and nipples supported in a bra. He fucked her for the longest time with me supporting his heavy balls as he thrust in and out of her. Her pussy obviously had adjusted to his size over the past month because she met each of his thrusts even as he pulled her legs over his shoulders and pounded her ruined pussy deeper and faster. It seemed like an hour before he grunted and his balls tightened in my hands. "Here it comes Baby!" He hissed as she cried out, "Yes! Yes! Fill me with your seed! Give me your Black baby". I was shocked at the "baby" part - I'd never considered she would get pregnant. At least, I assumed she was on birth control but later learned he'd made her stop the first time he fucked her. His balls contracted in my hands as he commanded me, "Squeeze them, Sissy! Fill your wife with my baby juice!" This time I felt my clitty drip as I squeezed his balls, feeling them crinkle and spasm as his cum flowed into her. She must have orgasmed ten times on his hard black cock. He filled her so much that it oozed out around his shaft as he continued to pump his black seed deep into her fertile white womb. Eventually he slowed and pulled his still massive cock from her cum filled pussy. Thick white globs poured from her sloppy hole. Her pussy lips were swollen and distended and she remained open and gaping even after he pulled out. As he rolled on his back, I knew what I was expected to do. I crawled onto the bed and began licking him clean. By now, I loved the taste of fresh cum and eagerly licked every drop from his softening but still huge black cock. “That’s a good girl, Sissy,” her lover sighed as I went to work. I could barely fit my hand around his girth as I guided the head into my mouth. Even more cum emerged into my mouth as I stroked his shaft and sucked the head. Probing his pee slit with my tongue. When I was sure he was completely clean, I turned my attention to my wife. I couldn't believe how much thick, salty sperm he had deposited inside her. It just kept leaking out into my mouth as I swallowed as fast as I could. My wife orgasmed again as I cleaned her making me so proud to please her. I looked up at my wife. Her smile beamed as she said, "You have some on your chin Sweetie," I scooped it into my mouth, swallowed, and smiled sheepishly at her. "Good girl," she complimented as I buried my face between her legs again. Just as she pushed a giant glob of his cum onto my tongue, I felt my panties being pulled down. I swallowed my mouthful of fresh cum as I glanced over my shoulder. Her lover was kneeling behind me with a tube of lube in one hand and one of his large fingers circling my smooth pink anus ring. I knew I couldn’t refuse him and nervously went back to licking my wife’s still cummy pussy. I could feel him apply cold, slippery gel to my pussy and then felt his thick finger pushing into me. His single digit was bigger than my milking dildo and stretched my pussy as it slipped past my tight anal ring. It felt strange and wonderful to have something alive inside me. He pressed it in further. I felt his knuckle enter and he kept going deeper. Soon he was sliding his whole finger deeply in and out of me. I could barely concentrate on licking my wife as he fucked my pussy with his huge finger. Eventually, he pressed downward and found my prostate. I discharged violently, spilling everything I had onto the bedspread. I tried to jump up and clean up my mess but he grabbed my tiny caged package firmly and held me in place. With two large fingers he pinched my balls at the base and used them as a tether as he continued to fuck my ass-pussy with his other hand. “You ain’t going nowhere, Sissy,” he said. With that he inserted a second slippery finger in my ass. Oh my God! His two fingers stretched me to the limit! “There you go Baby girl,” he said, “Just relax and enjoy it.” I tried to relax but each deep thrust brought such incredible feelings. By now, I had stopped licking my wife. When I realized it, I looked at her. She was thoroughly enjoying the sight of me impaled on his long, thick, Black fingers. “It feels good, doesn’t it Sweetie?” she asked. I just moaned and closed my eyes. It did feel good, so very good. I went down on my elbows and raised my ass for him. “Oh yeah, she likes it a lot.” Jamal said. “Just wait until she feels me inside her.” He added. With that, I wiggled my ass in agreement. This was the most pleasure I’d been allowed in our entire marriage. He added some more lube and slowly pressed a third finger into me. If I thought two was large, three fingers was overwhelming! He gently probed me for a long time before withdrawing his fingers. My ass felt so empty. But soon, I felt him at my anal entrance again. Only this time, it was the head of his enormous Black Cock! I tried to pull away but between him pressing down on my butt with his huge hand and my wife placing her hands on my shoulders, I was trapped. I glanced at my wife in panic. “Don’t worry, Sweetie,” she soothed, “I thought it was too big at first, but you’ll learn to love it soon enough.” Jamal instructed me, “Just relax and open your pussy for Daddy,” he said. Again, I tried to relax. Focusing on my flexing my anal ring for him. He could feel my tight ring “kissing” the head of his cock. “That’s it little girl,” he said. “Your pussy is mine too.” With that, I felt his head stretching me wide. It hurt so much! "He’s too big!, I thought, "It will never fit!” My mind shouted at me but my body was working hard to let him in. I rotated my hips and tried to open as wide as I could. It felt like a baseball bat was being pushed inside me. With a sudden “pop”, his giant head slipped past my anal ring. The pressure seemed to lessen but I was still stretched impossibly wide. He pushed a few inches further into me, then withdrew. Popping back through my abused ring. His cockhead nuzzled my opening and pushed back in. Then popped back out. He kept this up for the longest time. Popping in and out of me. I didn’t know, but he’d broken in many tight white wives and sissies. He was expertly conditioning my pussy to accept him. After an eternity of being impaled over and over again. He pulled out. “That’s enough for today, Sissy,” he said, slapping me ass hard. “Go get us something to drink while I fuck your sweet wife again.” I gingerly slipped off the bed and headed for the kitchen. I loved how feminine I felt as I walked through the house with my loose, wet pussy. It was sore but I was so happy he stopped before he damaged me. Jamal fucked my wife three more times that night as I stood by, serving them refreshments, and of course, cleaning his never-ending supply of cum from his cock and her overflowing pussy. I could feel my stretched pussy and wondered at how my wife could take all of him over and over again. By morning, they were fast asleep and my tummy was completely full of his cum. The next day, as I served her a very late breakfast, my wife was radiant and kept teasing me about being a real woman now. “I just knew you and Jamal would hit it off,” she said. “He's such a strong and powerful man. Just what we need, don’t you agree Sweetie?” “Yes Ma’am,” I agreed. “But he’s so big!” I complained mildly. “Oh yes!” she agreed. “So wonderfully big. He fills me so completely. I’m a little tender down there, but I suppose you understand that, don’t you Baby?” she smiled. “Don’t worry, you’ll adjust to his size. It took me a week to finally take all of him, but oh my God! It’s so worth it!” “You’ll be taking all of him too and we have plenty of time to break you in, the three of us are going on a cruise!” I was surprised and taken aback by the thought of the three of us going out in public together for any length of time. “We leave next Saturday, so while I’m at work this week, you need to pack our bags. Be sure to pack my sexiest and most revealing outfits. We’ll all be in the same cabin and I want everyone to know exactly what’s going on in there.” I could see she was excited at being with him for an entire week but also looking forward taking my cuckold status to the next level. On Monday, she brought home a large black dildo. It wasn't as big as Jamal but she instructed me to practice on it for at least three hours every day. “You need to stretch your mouth and ass-pussy if you expect to properly please our new Black Daddy, Baby.” She said. “And by the way, I had to suck off the Black man at the sex shop to get a discount. He wasn't nearly as big as Jamal, but he fit in my mouth and shot a lovely load of cum straight down my throat.” She kissed me and I could taste his cum on her breath. I did as she said, and spent the next week packing our bags and nervously preparing my mouth and pussy for the cruise.
Chapter 2: Cuckold Cruise
2 yıl önce
