Chapter 2: Cuckold Cruise
If you read Chapter 1, you know how I’ve been a weak, submissive sissy my whole life. My tiny nub of a penis never fully developed has never been inside a woman. I was fortunate enough to find and marry a strong and beautiful woman who accepted my submissive nature but only learned the full scope of my physical inadequacy on our wedding night. Rather than leave me then and there, she simply resumed her pre-marital sex life and my life as a sissy cuckold began. She took control of my life and my penis by locking me in what, for the past seven years, has been permanent chastity. Since then, our life together has been fairly quiet, routine, and wonderful and she’s enjoyed various lovers who kept her sexually satisfied. That is until recently… A few months ago, she met Jamal. A very large, dominant Black man. Since then, both of our lives have changed dramatically. With her submitting to him, and me submitting to both of them. He’s been with many other white women and enjoys dominating and fucking them but also enjoys using their sissy husbands. Until now, I’ve only been used to cleaning my wife and her lovers during and after their sex. But Jamal sees me as more woman than man and I’m just another pair of eager white holes to satisfy his enormous sexual appetite and a place to dump loads of cum from his huge black cock. After our first meeting and surrendering my mouth and virgin ass-pussy to him, I then learned he’d booked a week for the three of us on a cruise ship. I was apprehensive about spending so much time together, in such a public place but as the cruise date approached, I avoided thinking about it and kept busy packing our bags with sexy outfits for my wife. I’d learned over the years to simply accept whatever my wife wants and needs. Finally, when the day of the cruise arrived, we took a cab to cruise port with me in the front and my wife and Jamal making out in the back seat. The driver didn’t know what to make of it, but didn’t say a word. Upon arrival, I opened the door for them, then retrieved the baggage. He’d booked a suite, so we went directly to the VIP counter where I presented the paperwork for all of us as my wife and Jamal sat very close together, touching and sipping champagne. The check-in person could obviously see we were man and wife by our passports but didn’t bat an eye as she processed us in. “Here are your cabin keys,” she said. “This one is for you, and these two are for…your wife and…um…her friend.” giving me a knowing glance. Perhaps she’d seen many other couples with our unique relationship. I blushed and took the cabin cards over to them. They walked ahead, holding hands, with me trailing a few feet behind. Within minutes of entering our cabin, my wife and Jamal were naked and having sex on the bed as I unpacked their things. By the time I finished hanging up my wife’s dresses, folding their underwear, arranging their shoes, and putting away everything else, they had finished the first of many couplings they’d have on board. I dutifully crawled on the bed and cleaned them both thoroughly. They were both impressed that I was able to fit his deflated cock in my mouth and even into my throat. I’d been practicing every day for a week on a large Black dildo my wife purchased to prepare me for serving Jamal’s massive 10-inch cock. When I’d finished cleaning his copious semen from his cock and her completely full pussy, I made them drinks from the minibar and stood quietly in the corner as they snuggled. His large black body contrasting so perfectly with my wife’s pale naked skin and perfect breasts. Soon, there was a knock on the door. It was our cabin attendant introducing himself. He stepped inside and could see my wife and Jamal naked on the bed. “Excuse me Sir,” he said, apologizing profusely. “It’s OK, I said. I…I’m not…” My wife called from the bed, “He’s not Sir. This is Sir,” she said, running her hand over Jamal’s chest. “You can call him Sissy”. I was mortified but looked at the floor nodding in agreement and blushing deeply. “Yes Ma’am,” our attendant said, smiling to himself. “It’s a pleasure to meet you Ma’am, Sir, and…,” looking directly in my eyes, “Sissy... Enjoy your cruise.” They spent the rest of the afternoon fucking in the bed, in the shower, and even on the balcony.” My wife had been seeing Jamal at least three times a week for the past two months and her pussy had developed an insatiable craving for his gigantic Black Cock. This cruise would be their longest time together. The room was large for a cruise ship and my place was a couch in the corner. When I wasn’t busy serving them, I spent most of my time standing near my couch. By dinnertime, they were both starving although my stomach was once again full of Jamal’s thick, potent seed. They dressed for dinner with Jamal in a very nice suit and my wife in a shimmering low-cut dress that hugged her hips and showed off her flat stomach and gorgeous 36D breasts. Of course, my chastity key was always prominently nestled in her cleavage. She topped it off with a pair of tall black stiletto heels. I wore a simple suit I’d selected to be tasteful but not draw attention to me or away from them. At the table, my wife told the waiter, “No need to fuss, my husband will take care of us.” Again, I blushed as he studied me closely but said, “Of course, Ma’am. As you wish.” I pulled their chairs out for them, placed their napkins, and ordered the meals and poured the wine they’d selected from the menu. Each time, they said, “Thank you, Sissy,” loud enough for the tables nearby to overhear. They chatted intimately through dinner, paying little or no attention to me. They had both agreed that I needed to lose some weight and get a more “girlish” figure. So, I was only allowed to order a salad with no bread or excess calories. As we were dressing for dinner, my wife produced a corset for me to wear and had Jamal pull the laces tight before I pulled my shirt over it. I could barely breathe but it made my tummy flat and pushed my breasts up higher and bigger than ever. I didn’t know it at the time, but my wife had been giving me “vitamins” which were actually low doses of testosterone blockers and estrogen for almost a year. The changes were so gradual, I had no idea what was happening to my mind and body. My wife kept me completely hairless from the neck down for years and rarely allowed me to cut my hair. It had grown almost to my shoulders and thanks to the hormones was very silky and luxurious. My wife helped me style and curl it in a feminine style. My skin had become softer and I’d gained some weight in my bottom and of course, in my breasts. But I attributed the weight gain to overeating rather than redistribution of body fat from the hormones. The most notable effect was my larger, darker, and incredibly sensitive nipples. Which I loved so much; I didn’t question at all. At this time, I was totally oblivious to my gradual feminization and my very real budding breasts. At the dinner table, whenever the waiter offered more to eat, my wife or Jamal would chime in with, “No, she’s fine.” It was humiliating but strangely rewarding that they showed any interest in me. After dinner, we visited a few bars where I ordered drinks and served them while they sat together as a happy couple. Anyone passing by, couldn’t help but see the large Black man and his sexy white girlfriend. I was glad they didn’t notice me. The next day, they decided to spend time at the pool. I helped my wife into a tiny bikini that showed off her full hips, with only a string between her gorgeous ass cheeks, and her breasts spilling out nearly to her nipples. Jamal wore a speedo that completely failed to conceal the outline of his enormous Black cock. As they headed for the door, I grabbed a bag with sunscreen and water and tried to follow, as usual. Jamal stopped me and took the bag from my hand. Grabbed my caged clitty in his large hand and said, “Oh no, Sissy. Put on your bra, panties, and lipstick and clean the cabin like a good girl.” Adding as they went out the door, “and clean your pussy, I may want to finish breaking in that tight ass of yours today…” and they were gone. I immediately went to the bathroom and used a disposable enema to flush my bottom squeaky clean. Adding plenty of lube to the water and more of the slippery gel inside me before I finished. I knew if Jamal carried through on his plans for my ass, I needed to be very well lubricated if I wanted to survive! Next, I dressed as he’d ordered and was soon making the bed in what had become my “uniform” around the house. I do admit, I love how pretty I look with my hair brushed out, lipstick applied, and wearing my silky pink panties and the new pink training bra my wife had given me after Jamal decided my budding breasts needed support. My breasts felt so much bigger and wonderfully confined in my bra. The fabric instantly aroused my large puffy areolas and ultra-sensitive nipples. I hadn’t finished making the bed when the door suddenly opened! The maid braced the door open and walked right in. I must have been a sight, standing there holding a pillow in my pink lingerie and bright pink lipstick. She stammered, “Oh! I’m so sorry!” but didn’t leave right away. She stood there looking me up and down. My caged clitty was easily visible through my panties. I said, “No, it’s OK. I…I’m cleaning up for my wife and…”. “Oh, you must be the ones…” but she corrected herself before revealing the staff had been discussing our living arrangements. “Yes.” I confirmed, accepting that everyone would eventually know about us…about me. She smiled sympathetically and had an idea. “Wait here.” She said, as if I would step out of the cabin dressed this way. She scurried away and returned a few minutes later. “This should fit you.” she smiled sweetly, offering a maid’s uniform identical to the one she was wearing. “If you’re going to do my job, you should at least dress properly”, she offered. “But you can’t tell anyone – and you can’t leave the cabin in this. I’ll get in big trouble. Go ahead, try it on.” I timidly accepted the uniform and went to the bathroom. It fit perfectly! I hesitantly stepped back in the room to her beaming approval. “Very good! You are now a maid. But we must fix your hair.” She sat me at the mirror and put my hair in a bun using one her hair bands. “Now, you are perfect,” She complimented, “Now, I must go and you have plenty of work to do!”. I thanked her several times and led her to the door. “What is your name, Miss?” she asked as she was leaving. “They call me…Sissy.” I admitted shamefully. “Oh yes, that’s right. I have a cousin who is also a sissy. OK, goodbye Sissy the Maid.” She said cheerfully and left me in the room. I looked in the mirror and was amazed at how feminine I looked. I actually could have stepped out of the room and not been noticed as other than a cabin maid. I made the room spotless and spent the rest of my time alone practicing on my big Black dildo. I still had a long way to go before I could deep throat my toy or even take half of Jamal’s huge, thick cock in my throat or ass pussy. But I was able to loosen them a bit more with each session. Most of the time, my mind was blank as I concentrated on the task at hand. I rarely gave much thought to how my life had turned out. My only concern was pleasing my wife in the only way I was physically able. But the more I dressed as a girl and behaved like a girl, the more I felt I was a girl inside. I had to admit to myself that I loved feeling feminine and girly. Whenever my wife saw me dressed in panties and bra, I sensed her approval and it felt wonderful. And when Jamal looked at me, oh my goodness! I felt the strongest desire to please him! My attraction to his big Black Cock was undeniable. I wanted him to want me. I wanted to suck his cock and I wanted to feel his cock inside me. The only remnant of my ever being a man was my tiny caged clitty and lately, it was as if I didn’t even have that. It was just something to keep clean and presentable for them. I hardly ever noticed my cage anymore and I certainly didn’t think of it as a penis at all. When they returned from the pool, I answered the door in my maid’s uniform and stood aside as they entered. “Look at you, Sweetie!” my wife commented. “You look adorable. Did someone help you dress?”. “Yes Ma’am, the maid found me in my panties and loaned me a uniform.” I replied meekly but feeling very proud that she was pleased. “Perhaps we should get you a job cleaning houses for my friends at home?” she teased. The thought of being exposed in a maid’s uniform to her friends startled me, but I was fairly sure they were aware of our relationship by now. Whenever her friends visited, I always served drinks and snacks and stood nearby obediently responding to my wife’s commands. They always made comments like, “I need to train my husband to be so attentive.” I could also hear them giggling when I was out of the room and my wife would jangle my key when she wanted to make a point. The other girls always laughed when she shook it at me. My humiliation was so constant at this point, hiring me out as a Sissy Maid wouldn’t have been much further. “As you wish,” I conceded, picking up the proper reply from the waiter on the ship. Well, right now, I could use a blowjob,” Jamal interjected. “Not from me, I’m going to get cleaned up.” My wife said, stepping into the bathroom. “Honey, take care of Jamal for me.” She called out to me, leaving us alone in the room. “That works for me,” Jamal said, stepping forward and pulling off his speedo. I didn’t hesitate to fall to my knees in front of him. His thick cock hung heavily in front of me and was already growing. I reached up and tried to fit my hand around his thickening girth. My fingers couldn’t touch around him so I used both hands to stroke him in front of my face. I opened my mouth and placed my lips around the fat head. He was leaking precum and I lapped it up, savoring the sweet and salty taste on my tongue. I opened wide and fit the entire head inside as he moaned in pleasure. “That’s it, little girl, suck Daddy’s dick”. I went to work sucking the head and licking up and down the length of his shaft. I cupped his enormous balls in one hand as I guided him back into my mouth. Each time, I tried to fit more of him inside me - but he was so thick! I was able to get three or four inches into my mouth and felt him pressing at the back of my throat. He was impressed and said, “Good girl, you’ve been practicing. But you have a long way to go. When I’m done with you, I expect to feel my balls on your lips and all of me down your sissy throat. Is that clear?” I gave as much of a muffled agreement as possible with him filling my mouth to the limit. I felt a sharp stinging slap on my face. “Look at me when you suck a real man’s cock, Sissy.” I obediently looked up into his eyes as I continued sucking him. With each inward stroke he held my head and pressed deeper inside me. I couldn’t help but gag on him but he seemed to like that. I concentrated on stroking his hardening shaft and hoping to get him to cum quickly but I’d witnessed his incredible stamina with my wife so I resigned myself to being impaled on his cock for a long time. He fucked my mouth for at least fifteen minutes but it seemed like hours. I could tell by the wet line of my saliva how far down his shaft my lips had reached and was amazed when he pulled out that I had taken nearly half of him. He rubbed his hard cock all over my face but my relief was short as he pushed back into my mouth and continued to fuck my throat faster and deeper each time. I frantically stroked his shaft and swirled my tongue around his head. I tried hard to relax my throat and let him in. I could feel his thick round head stretching my tight throat with each stoke and popping in and out of my esophagus. He treated my throat as his pussy and I had to little time to breathe between thrusts of his massive organ. My attentions finally paid off because just as my wife stepped out of the bathroom, I felt him stiffen and grunt as a torrent of his thick semen gushed into my mouth, most of it pouring straight down my throat. I swallowed and swallowed but it just kept coming. Some of it escaped from the sides of my mouth and ran down my chin. I pulled back and licked his sweet cum off the shaft and scooped thick, creamy pearls from my face into my mouth. “Good girl!” my wife complimented, as she watched me feverishly gobbling up his massive load. “He cums so much, doesn’t he Sweetie?” she patted me on the head as she walked by. I nodded but kept licking it up, careful not to spill a single drop. When he finished, he pulled out and took my chin in his hand as I looked into his eyes and swallowed a big mouthful of his delicious cum. “Good Sissy. You might just learn to be a good cocksucker yet.” Then he kissed my forehead and went off to the bathroom as I continued to kneel on the floor wondering at what had just happened. I had sucked off a man! A big Black Man. And without my wife being present. His kiss sent a thrill through my entire body! Was I gay? I didn’t know. But I knew I loved having him in my mouth and his approval made me feel so feminine and desirable. My wife came over to me, “He’s perfect for us, isn’t he Baby? I can see you love his cock as much as I do.” A tear formed in my eye as I admitted to her, “Yes, I love how he makes me feel.” “Don’t worry Sweetie,” my wife consoled, “It’s perfectly natural for a girl like you to want a real man like him.” I started to deny it, “But I’m not a…” I started. She put a finger to my lips. “Not yet, Sweetie. But you will be…”. I wasn’t sure what she meant but I knew whatever she had in mind for me was going to happen whether I wanted it or not. For the next couple of days, things continued much the same way. Every time we left the cabin, I followed submissively, serving them food, drinks, towels, or whatever they needed. Often as we stepped into the hallway, neighbors would see this huge black man obviously intimate with this gorgeous white woman and then this smaller white man following behind them. My wife always made a point of saying, “Come along, Sissy” or “Run ahead Sissy and save us some lounge chairs,” just at the right moment for others to hear. I always replied with, “Yes Ma’am” or “As you wish, Ma’am”. They also made me wear my most feminine clothes that accentuated my budding breasts and developing ass. My mid-section was almost always exposed and thank goodness they allowed me to wear flesh tone lipstick! Jamal worked out in the gym several hours each morning, and I gave him a full body massage each afternoon. I’m proud to say, every massage session ended with his cock standing fully erect! The first few times, he called my wife over and made long passionate love to her. But on the third afternoon…I’d rubbed his beautiful muscled body from head to toe and stroked his enormous Black Cock to full attention. I finished with a loving kiss on the tip where I was delighted to find a pearl of yummy precum. A shimmering string of cum stretched from my lips to his cock as I pulled away and tried to get up from the bed. I felt his strong hand on my wrist. I looked at him and saw the lusty gaze in his eyes. “Not today, Sissy. It’s your time.” He said pulling me to him and kissing me on my lips. I was in shock but his thick lips felt so wonderful against mine. I submissively melted into him as his tongue probed deeply into my mouth. I couldn’t help but moan softly in a girlish voice. He rolled me onto my back and kissed me again. His huge frame pinning me to the bed. “Are you ready for this?” he asked, in a soft and gentle tone. My eyes watered in emotion and I nodded silently. I had practiced with my toy every day for almost two weeks now. My pussy was clean and slippery and very used to being invaded. Just not by something as big as Jamal. He knelt between my legs and grabbed the bottle of massage oil, pouring it all over his thick, hard, Black Cock. It glistened as he stroked the oil up and down the shaft and all over the head. He reached under my right leg and effortless lifted me off the bed pouring even more oil all over my chastity and letting it run down my crack. He’d set down the oil and began rubbing the oil around my exposed anus. Swirling it around my hole and gently pressing a thick finger inside with each rotation. It felt so wonderful! My wife had been reading a magazine but stopped to watch Jamal preparing to fuck her sissy husband. I could see her hand slip between her thighs as she enjoyed the show. With more oil, he pressed two fingers inside me. My pussy opened for him and it was much easier than the first time he’d filled me with his fingers. He fucked me with two fingers for a long time, stretching me, preparing me…and then he pulled them out. My pussy felt so empty but soon his thick, round cockhead was pressing firmly against my pussy ring. Only this time, I was mentally and physically ready to give myself to him. I opened as wide as I could and lifted my legs high. He pulled my legs over his shoulders and pressed gently into me. “Oh my God, he’s so thick!” my mind raced. Maybe I wasn’t ready for this! It seemed like forever as his giant round head spread my tiny opening wider and wider. I panted as if giving birth and tried to relax my anus as much as I could. He was very good at opening tight holes and would press forward until I couldn’t give anymore, then retreat slightly. Then press forward again, rolling the head around my sphincter, opening me a tiny bit further. Each time working himself deeper in me. Just when it felt like I couldn’t open any wider, his fat head finally popped past my insanely stretched ring and the pressure decreased. My pussy gripped his thick cockhead and I relaxed for moment. But my relief was short lived as he continued his conquest of my mostly virgin ass-pussy.
By now, my wife had come over to the bed and was pinning my arms above my head as she whispered soft words of encouragement. “Good girl,” she said, “You’re doing great, Sweetie. Just relax and let him in. It helps to wiggle your hips, Baby.” I could barely hear her, as my mind was focused on the gigantic phallus working its way inside me. He had slowly rocked another three inches in and out of me and was reaching the point on his shaft where it was every bit as thick as his fat, mushroom head. Every now and then, Jamal would pull back and squirt more lube on his shaft, then press back in. He paused at four inches and slowly fucked me. Pulling back to the head but keeping it inside me, then pushing back to the wet line on his thick shaft. He did this for a long time, as my pussy slowly accustomed to his girth. On one outward stroke, he slowly pulled all the way out. Letting my anus glide around his bulbous head then hang loosely open, my stretched ass wetly kissing his fat head, before pressing back inside me. Oh my God! I felt so empty without him and so full when he re-entered! He did this over and over again, until my ass-pussy opened easily and hungrily for him each time. I was in heaven! A mixture of pain and pleasure swept over my body. My wife released my arms and crept over my head, nestling her dripping wet pussy on my panting mouth and pinching my incredibly hard and erect nipples as he continued to fuck me. The smell was intoxicating and I could taste their residual cum. Jamal was slowly inching deeper inside me, withdrawing almost out of me, then slightly deeper. Picking up the pace as he sensed I could take it. By now, at least five or six inches of thick, hard, Black Cock was sliding in and out of me. I’d never been fisted but knew this must be what it feels like. My legs were still high over his shoulders and I felt something new and amazing. With each deep stroke, I could feel huge balls slap against me. It started with a graze but grew larger with each deeper stroke. Their presence grew more and more until finally, his fat balls were hitting full on my backside. I knew he had to be nearly all the way inside me! Just the thought of his 10-inch cock all the way inside me, sent my mind whirling. Each time he pressed deeper, the pain returned but after five or six strokes it subsided as my ass-pussy adjusted to him. I hadn’t been doing much for my wife, as my whole world was centered around the huge Black cock plowing in and out of me. She climbed off my face and moved behind Jamal to watch him stretch her sissy husband wide open. She knew exactly what it felt like to be helpless under this gorgeous man. I grabbed onto his massive biceps with my delicate hands and dug my long, painted nails into his skin as he pummeled my formerly tight ass-pussy. Finally, finally, he touched bottom. I was in shock that I had taken all of him! He paused, pressing his body against mine, grinding himself as deep as he could go. His massive balls resting on my ass. I looked in his eyes, with so much love, tears filling my eyes at the emotion. He leaned down and kissed me. Flexing his all ten inches inside me at the same time. That was all it took! My clitty erupted in its cage. This wasn’t the same feeling as my monthly milking. No, this was a full body Sissygasm. My legs trembled and my whole body shook as waves of pleasure surged through me. I writhed uncontrollably on his thick pole buried inside me. Spurt after spurt of sissy cum pulsed out of me and I cried out in the most intense sexual pleasure I’d ever experienced. He held me down until my orgasmic throes subsided, then began fucking me full length. His gigantic cock sliding almost all the way out and pushing all the way back in. I nearly passed out in ecstasy as he pumped even more cum from my tiny clitty and kept on going. He was fucking me harder and faster now. My orgasm still subsiding in long feminine waves. All I could do was hang on for the ride as he turned the moment from my pleasure to his. He fucked me for so long! I lost track of time and desired only to please him. My somewhat tight sissy hole eventually worked its magic and I could feel him getting close. I focused on opening my ass on the downstroke and gripping his shaft as he pulled back. He finally grunted loudly and pushed all the way inside me, it felt deeper than ever before as he spilled gallons of his superior seed deep in my used sissy pussy. I was overjoyed to have made him cum and I bucked against him as his cock spasmed and kept pumping inside me. My wife had been licking his ass as he fucked me but was now holding his heavy balls and squeezing them as he came in me. “Yes Baby! That’s it!” she coached. “Take it all Sweetie!” I couldn’t help myself, I kissed him deeply and started crying in joy as he filled me with his warm sperm. For the first time in my life, I truly felt like a woman. I never wanted this feeling to end. He lay there for a while, his weight pinning me helplessly to the bed and his cock still spasming deep inside me. I held his head in my hands, rubbing and kissing him as he rested on my breasts. But too soon, it was over, and he pulled his deflating, but still huge, cock out of my ass-pussy with a wet plop. I could feel my ass-pussy didn’t close all the way and it felt wonderful. I imagined this is what a real pussy feels like after something so big had ravaged it. I reached down and circled my abused slippery anus with my fingertip, feeling his thick, fresh cum oozing out of me. My wife also noticed his cum and said, “Are you forgetting something Honey? Daddy still needs cleaning, and don’t think any of that cum inside you is going to waste.” I quickly returned from my afterglow not knowing what to do first. My wife helped by grabbing a coffee cup. “Get to work on Daddy, and I’ll catch the rest.” She directed. As I knelt over Jamal and began licking his glistening, cum covered cock, my wife captured his thick seed as it poured from my very full pussy, dripping down my tiny, shriveled balls, and into her waiting cup. I cleaned him thoroughly, lovingly suckling his beautiful cock. But he had cum so hard in me, he wasn’t growing this time. In fact, he dozed off as I licked and sucked him clean. It gave me intense satisfaction to have pleased him so well. When I finished, I turned and sat on the edge of the bed. My wife stood before me with the coffee cup, half full of his still warm semen. She handed it to me but said, “Wait a minute”. She fetched her phone, then pointed the camera at me before saying, “Go on Sissy, drink a cupful of your Black Daddy’s sperm from your freshly fucked virgin ass.” It was unsettling, because she had never made a video of me before. But I followed her command and tipped the cup to my lips, allowing his sweet, salty cum to flow into my mouth. It tasted slightly different than usual but not terrible considering it had been deposited deep in my colon. Fortunately, I’d cleaned myself very well. I looked at the camera and swallowed it all. Tipping the cup and allowing the last drops to drip onto my extended tongue. “Good girl,” my wife complimented. “Now go freshen up your hair and make-up. You’re a hot mess, Sweetie.” I tried to stand up but my entire bottom end was sore, and loose, and just…felt different. I wobbled unsteadily toward the bathroom, rolling my hips and stepping very gingerly. “Now you know what a woman feels like Sweetie,” my wife called after me. She was right, I felt more feminine that ever and loved it so much. It took a full day for my ass to close completely and walking was tender for several more. Fortunately, Jamal was satisfied with fucking my wife’s ass and pussy and settled for blowjobs from me when she was tired or busy. I could now take almost all of him down my throat. Stretching my lips and learning not to gag, was the hardest part. After that, my throat accepted him as deep as he wanted to go. My lips were constantly swollen but I liked the look, especially with lipstick on. At one point, we were walking around the ship and he pulled us both into the corner of an empty bar. “Both of you, on your knees,” he commanded. My wife and I looked at each other but obeyed. He pulled out his cock and said, “Suck it.” We looked around and nobody was nearby, of course there were cameras everywhere, but we both complied. It was the first time I had shared Jamal’s huge cock with my wife at the same time. I licked the shaft and suckled his balls as she sucked on his giant head. Then we would swap. All four of our hands were on his shaft with room to spare. I licked and sucked on his heavy balls as my wife slipped a finger between his ass cheeks and massaged his anus. Before long, he gripped his shaft and groaned as he pumped his load all over our faces. We tried to catch it in our mouths but he kept spurting it all over our noses, foreheads, and cheeks. “Good girls.” He sighed, stuffing his deflating monster back in his shorts. I tried to scoop his seed into my mouth but he stopped me. “No, no, no. Not this time. I want you to wear it.” He commanded. “Both of you,” he added looking at my wife too. We walked all the way back to the cabin with his warm seed all over both of our faces. Most people didn’t notice but there were more than a few knowing smiles along the way. In the elevator, you couldn’t help but smell his musky semen. He pushed all the buttons making us stop at every floor. When we finally reached the cabin he said, “OK. You can lick it off each other now.” We cleaned each other thoroughly as he watched us licking his yummy cum from each other and kissing deeply with his thick seed swirling on our tongues. It was so erotic and I loved the rare moment of sexual intimacy with my wife. The rest of the cruise went on the same way, with me cleaning the cabin every day in my uniform. My wife and I satisfying Jamal’s never ending sexual needs. And both of them finding new and ever more humiliating ways to expose me as a Sissy. Jamal fucked me once more on the last night of the cruise but this time, he just took me face down over some pillows. It was more about satisfying his needs than making love. I still had an intense Sissygasm as he filled me with his cum but I craved the gentle face to face, connection I felt the first time. Regardless of how I felt, my mouth and ass-pussy were now trained to accept his gigantic cock anytime and anywhere. Also, by the end of the cruise, I accepted that most of the passengers and crew knew I was a white sissy cuckold, it was a truth that I’d come to accept without shame. Everywhere we went on board, I could hear people whispering, “Sissy” and “Yes, that’s her husband”. But I didn’t care anymore. As confused as I was about everything that had happened, I now realize I was falling in love with Jamal and would have done anything for him and my wife. On the last day, I tried to return my neatly folded maid’s uniform but she said, “It’s OK, you can keep it.” Smiling knowingly in Jamal’s direction. “Perhaps you’ll be needing it at home…thank you for doing my job - I wish you luck, my Sissy Sister.” We hugged and I thanked her again. The cabin attendant offered to carry the hand baggage but Jamal insisted I would take care of it. “Oh, of course,” he said. “I trust you thoroughly enjoyed your cruise Sir, Ma’am...” Then looking me up and down like a girl, “Sissy”. This time, I wasn’t humiliated but felt a sense of pride to serve these two beautiful people. Jamal tipped everyone very well, ushered my wife out the door, and they walked off the ship, hand in hand, with me following obediently behind. Still tender and limping slightly, but very happy.
Next Chapter: Cuckold Sissy Maid
By now, my wife had come over to the bed and was pinning my arms above my head as she whispered soft words of encouragement. “Good girl,” she said, “You’re doing great, Sweetie. Just relax and let him in. It helps to wiggle your hips, Baby.” I could barely hear her, as my mind was focused on the gigantic phallus working its way inside me. He had slowly rocked another three inches in and out of me and was reaching the point on his shaft where it was every bit as thick as his fat, mushroom head. Every now and then, Jamal would pull back and squirt more lube on his shaft, then press back in. He paused at four inches and slowly fucked me. Pulling back to the head but keeping it inside me, then pushing back to the wet line on his thick shaft. He did this for a long time, as my pussy slowly accustomed to his girth. On one outward stroke, he slowly pulled all the way out. Letting my anus glide around his bulbous head then hang loosely open, my stretched ass wetly kissing his fat head, before pressing back inside me. Oh my God! I felt so empty without him and so full when he re-entered! He did this over and over again, until my ass-pussy opened easily and hungrily for him each time. I was in heaven! A mixture of pain and pleasure swept over my body. My wife released my arms and crept over my head, nestling her dripping wet pussy on my panting mouth and pinching my incredibly hard and erect nipples as he continued to fuck me. The smell was intoxicating and I could taste their residual cum. Jamal was slowly inching deeper inside me, withdrawing almost out of me, then slightly deeper. Picking up the pace as he sensed I could take it. By now, at least five or six inches of thick, hard, Black Cock was sliding in and out of me. I’d never been fisted but knew this must be what it feels like. My legs were still high over his shoulders and I felt something new and amazing. With each deep stroke, I could feel huge balls slap against me. It started with a graze but grew larger with each deeper stroke. Their presence grew more and more until finally, his fat balls were hitting full on my backside. I knew he had to be nearly all the way inside me! Just the thought of his 10-inch cock all the way inside me, sent my mind whirling. Each time he pressed deeper, the pain returned but after five or six strokes it subsided as my ass-pussy adjusted to him. I hadn’t been doing much for my wife, as my whole world was centered around the huge Black cock plowing in and out of me. She climbed off my face and moved behind Jamal to watch him stretch her sissy husband wide open. She knew exactly what it felt like to be helpless under this gorgeous man. I grabbed onto his massive biceps with my delicate hands and dug my long, painted nails into his skin as he pummeled my formerly tight ass-pussy. Finally, finally, he touched bottom. I was in shock that I had taken all of him! He paused, pressing his body against mine, grinding himself as deep as he could go. His massive balls resting on my ass. I looked in his eyes, with so much love, tears filling my eyes at the emotion. He leaned down and kissed me. Flexing his all ten inches inside me at the same time. That was all it took! My clitty erupted in its cage. This wasn’t the same feeling as my monthly milking. No, this was a full body Sissygasm. My legs trembled and my whole body shook as waves of pleasure surged through me. I writhed uncontrollably on his thick pole buried inside me. Spurt after spurt of sissy cum pulsed out of me and I cried out in the most intense sexual pleasure I’d ever experienced. He held me down until my orgasmic throes subsided, then began fucking me full length. His gigantic cock sliding almost all the way out and pushing all the way back in. I nearly passed out in ecstasy as he pumped even more cum from my tiny clitty and kept on going. He was fucking me harder and faster now. My orgasm still subsiding in long feminine waves. All I could do was hang on for the ride as he turned the moment from my pleasure to his. He fucked me for so long! I lost track of time and desired only to please him. My somewhat tight sissy hole eventually worked its magic and I could feel him getting close. I focused on opening my ass on the downstroke and gripping his shaft as he pulled back. He finally grunted loudly and pushed all the way inside me, it felt deeper than ever before as he spilled gallons of his superior seed deep in my used sissy pussy. I was overjoyed to have made him cum and I bucked against him as his cock spasmed and kept pumping inside me. My wife had been licking his ass as he fucked me but was now holding his heavy balls and squeezing them as he came in me. “Yes Baby! That’s it!” she coached. “Take it all Sweetie!” I couldn’t help myself, I kissed him deeply and started crying in joy as he filled me with his warm sperm. For the first time in my life, I truly felt like a woman. I never wanted this feeling to end. He lay there for a while, his weight pinning me helplessly to the bed and his cock still spasming deep inside me. I held his head in my hands, rubbing and kissing him as he rested on my breasts. But too soon, it was over, and he pulled his deflating, but still huge, cock out of my ass-pussy with a wet plop. I could feel my ass-pussy didn’t close all the way and it felt wonderful. I imagined this is what a real pussy feels like after something so big had ravaged it. I reached down and circled my abused slippery anus with my fingertip, feeling his thick, fresh cum oozing out of me. My wife also noticed his cum and said, “Are you forgetting something Honey? Daddy still needs cleaning, and don’t think any of that cum inside you is going to waste.” I quickly returned from my afterglow not knowing what to do first. My wife helped by grabbing a coffee cup. “Get to work on Daddy, and I’ll catch the rest.” She directed. As I knelt over Jamal and began licking his glistening, cum covered cock, my wife captured his thick seed as it poured from my very full pussy, dripping down my tiny, shriveled balls, and into her waiting cup. I cleaned him thoroughly, lovingly suckling his beautiful cock. But he had cum so hard in me, he wasn’t growing this time. In fact, he dozed off as I licked and sucked him clean. It gave me intense satisfaction to have pleased him so well. When I finished, I turned and sat on the edge of the bed. My wife stood before me with the coffee cup, half full of his still warm semen. She handed it to me but said, “Wait a minute”. She fetched her phone, then pointed the camera at me before saying, “Go on Sissy, drink a cupful of your Black Daddy’s sperm from your freshly fucked virgin ass.” It was unsettling, because she had never made a video of me before. But I followed her command and tipped the cup to my lips, allowing his sweet, salty cum to flow into my mouth. It tasted slightly different than usual but not terrible considering it had been deposited deep in my colon. Fortunately, I’d cleaned myself very well. I looked at the camera and swallowed it all. Tipping the cup and allowing the last drops to drip onto my extended tongue. “Good girl,” my wife complimented. “Now go freshen up your hair and make-up. You’re a hot mess, Sweetie.” I tried to stand up but my entire bottom end was sore, and loose, and just…felt different. I wobbled unsteadily toward the bathroom, rolling my hips and stepping very gingerly. “Now you know what a woman feels like Sweetie,” my wife called after me. She was right, I felt more feminine that ever and loved it so much. It took a full day for my ass to close completely and walking was tender for several more. Fortunately, Jamal was satisfied with fucking my wife’s ass and pussy and settled for blowjobs from me when she was tired or busy. I could now take almost all of him down my throat. Stretching my lips and learning not to gag, was the hardest part. After that, my throat accepted him as deep as he wanted to go. My lips were constantly swollen but I liked the look, especially with lipstick on. At one point, we were walking around the ship and he pulled us both into the corner of an empty bar. “Both of you, on your knees,” he commanded. My wife and I looked at each other but obeyed. He pulled out his cock and said, “Suck it.” We looked around and nobody was nearby, of course there were cameras everywhere, but we both complied. It was the first time I had shared Jamal’s huge cock with my wife at the same time. I licked the shaft and suckled his balls as she sucked on his giant head. Then we would swap. All four of our hands were on his shaft with room to spare. I licked and sucked on his heavy balls as my wife slipped a finger between his ass cheeks and massaged his anus. Before long, he gripped his shaft and groaned as he pumped his load all over our faces. We tried to catch it in our mouths but he kept spurting it all over our noses, foreheads, and cheeks. “Good girls.” He sighed, stuffing his deflating monster back in his shorts. I tried to scoop his seed into my mouth but he stopped me. “No, no, no. Not this time. I want you to wear it.” He commanded. “Both of you,” he added looking at my wife too. We walked all the way back to the cabin with his warm seed all over both of our faces. Most people didn’t notice but there were more than a few knowing smiles along the way. In the elevator, you couldn’t help but smell his musky semen. He pushed all the buttons making us stop at every floor. When we finally reached the cabin he said, “OK. You can lick it off each other now.” We cleaned each other thoroughly as he watched us licking his yummy cum from each other and kissing deeply with his thick seed swirling on our tongues. It was so erotic and I loved the rare moment of sexual intimacy with my wife. The rest of the cruise went on the same way, with me cleaning the cabin every day in my uniform. My wife and I satisfying Jamal’s never ending sexual needs. And both of them finding new and ever more humiliating ways to expose me as a Sissy. Jamal fucked me once more on the last night of the cruise but this time, he just took me face down over some pillows. It was more about satisfying his needs than making love. I still had an intense Sissygasm as he filled me with his cum but I craved the gentle face to face, connection I felt the first time. Regardless of how I felt, my mouth and ass-pussy were now trained to accept his gigantic cock anytime and anywhere. Also, by the end of the cruise, I accepted that most of the passengers and crew knew I was a white sissy cuckold, it was a truth that I’d come to accept without shame. Everywhere we went on board, I could hear people whispering, “Sissy” and “Yes, that’s her husband”. But I didn’t care anymore. As confused as I was about everything that had happened, I now realize I was falling in love with Jamal and would have done anything for him and my wife. On the last day, I tried to return my neatly folded maid’s uniform but she said, “It’s OK, you can keep it.” Smiling knowingly in Jamal’s direction. “Perhaps you’ll be needing it at home…thank you for doing my job - I wish you luck, my Sissy Sister.” We hugged and I thanked her again. The cabin attendant offered to carry the hand baggage but Jamal insisted I would take care of it. “Oh, of course,” he said. “I trust you thoroughly enjoyed your cruise Sir, Ma’am...” Then looking me up and down like a girl, “Sissy”. This time, I wasn’t humiliated but felt a sense of pride to serve these two beautiful people. Jamal tipped everyone very well, ushered my wife out the door, and they walked off the ship, hand in hand, with me following obediently behind. Still tender and limping slightly, but very happy.
Next Chapter: Cuckold Sissy Maid
2 years ago