I was still lying on the bed, savouring the taste of Don’s seed in my mouth, wearing the leopard print bikini, contemplating what I had just done. I never would have thought it, but being forced to clean up Don’s big black cock and eating all his cum out of Mistress Bella’s pussy had really turned me on. My hard little clitty was pressing against the little pink chastity cage. At that moment, I wanted nothing more than to jerk off, but the cage was stopping me from doing that.
Mistress Bella and Don lay naked in bed, in each other’s embrace. She was a French ex-swimwear model with long dark hair, a perfect peachy ass, D-cup breasts and a toned body. Don was the epitome of a black alpha male. He was in his mid-forties, bald except for a greying goatee, bulging muscles and a huge, thick black dick. He wasn’t erect anymore, but it was still the size of a large beer can.
Finally, Bella broke the silence. “Olivia, why don’t you go find Lexi? Don and I want to have some alone time.”
I sat back up. “Yes, Mistress,” I responded as I climbed off the bed.
As I wandered through the superyacht, back up to the front deck in my bikini, I was aware that one or two of the black crew members were checking me out. Did they know what I had just done in Don and Bella’s master suite? Finally, I found Lexi tanning on one of the sunbeds.
As I approached, she lifted her head and spoke with a sly smile. “Hey, girl! Did you have fun down there with the two of them?”
“To be honest, I enjoyed that way more than I thought I would have,” I pensively responded.
“That’s good.” Lexi smiled back. “It sounds like you and the sissy lifestyle are a natural fit.”
We lay on the sunbeds for a while, as I thought about my belly full of Don’s cum. Would I ever get out of this pink chastity cage? Was it normal for white boys to wear women’s clothes and suck other men’s dicks? Why had it turned me on so much?
Lexi leaned over to me and said, “I think it’s time we get ready for dinner, Olivia. I’ll show you to your new quarters.”
I followed her inside, and we went downstairs to a cabin. It was noticeably smaller than Don and Bella’s suite, but still had ample space and an en suite bathroom.
“You’ll be sharing a room with me from now on,” she spoke as she walked over to a wardrobe, opening it to reveal an overflowing closet of women’s clothes.
I just stared into the wardrobe in amazement. There were so many different outfits in it. I almost didn’t notice Lexi strip out of her bikini. She was facing away from me, and I got a good look at her peachy ass and long, glossy blonde hair. As she turned around to face me, my eyes fell on her small, perky breasts. She had pink, puffy nipples that caught my gaze. My eyes kept progressing down her body until I saw a small limp dick.
“Wait,” I exclaimed. “You’re like me?”
Lexi smiled back at me for a moment. “I’ve wanted to tell you since Mistress Bella spied you on the beach, but she forced me to keep it a secret until now.”
I was dumbfounded, and finally, I found my words. “S…So how did you end up on the superyacht like this?”
Still naked, Lexi reclined onto the bed, as I kept eyeing up her boobs and little limp dick. “Just over a year ago, I met Mistress Bella on a night out at a gay bar in San Diego. I had never been to one before, and to be honest, before that night, I hadn’t considered myself interested in other men. We clicked immediately, and believe it or not, I actually thought I was in with a chance of sleeping with her. She invited me back to the superyacht, and we ended up having a few more drinks. One thing led to another, and somehow, I ended up trying on some of her clothes. I passed out that night, and when I woke up the next morning, we were already out to sea. When I confronted Bella, she gave me a choice of returning home to my mundane life or staying here and having a new, exciting life. Obviously, there were a few conditions. It started with me having to be dressed as a girl the entire time, before progressing into servicing horny men, or even women on occasion, for the pleasure of Mistress Bella and Don.”
Had I heard Lexi correctly? Had she willingly chosen this life as a girl?
“So how come you don’t have to wear one of these things?” I asked as I pulled down my leopard print bikini bottoms to reveal my tiny pink chastity cage.
Lexi sat upright, engrossed at the little cage I was wearing, and cupped it in her hand, before staring up into my eyes and responding, “You know, Mistress Bella and I spoke about it at the beginning of my journey. She gave me a choice of either wearing one of these.” She paused for a moment to squeeze my locked clitty. “Or she told me I had to go on hormone replacement therapy.”
She paused for a moment to let that sink in before starting up again. “I chose to take the oestrogen, and never looked back. It started changing my body almost immediately and most notably I started growing these little titties.” She dropped my locked clitty and was now squeezing her perky breasts together. “Although it started doing a lot more to my body too. My dick and balls shrank, my voice started changing, my body started getting curvier, and even my body hair got thinner.”
“That’s c…crazy,” I stammered out. “Do you think I will have to start taking oestrogen too?”
“Potentially, if Mistress Bella thinks you are ready, then I am sure one day you could look just like me, too.”
I stood there contemplating what Lexi had just said, staring at her gorgeous hairless legs, until I realised she had a tattoo on her ankle.
“What’s that?” I asked.
She pulled her leg up onto the edge of the bed so I could get a better look. In elegant writing, someone had tattooed onto Lexi, ‘Property of Mistress Bella’.
“Oh, Mistress did this pretty early on in my journey to help teach me my place in life. I’m sure you’ll get yours soon,” Lexi giggled back at me.
Fuck. I knew I was willingly playing along with Bella and her games for the moment, but did I really want to be branded like that? Did I really want a tattoo on my body for the rest of my life, signifying me as a sissy slave?
I sat down on the bed in shock from everything Lexi had just told me, unable to process what was going on. Whilst I was sitting down, Lexi stood up and wandered over to a chest of drawers and pulled some bits out, before laying them on the bed, then doing the same with something from the wardrobe.
“I know you don’t have any clothes of your own at the moment, so I thought you could wear these for tonight,” she caringly said to me.
I looked down next to me, and there was a midnight blue lace push-up bra that had a white trim. There was also a matching thong, and next to the lingerie lay a short, strappy burgundy dress with a small slit at the bottom of the hem.
I was still in a slight daze about what I had learnt from Lexi, so I just smiled back at her before I undid the straps from the leopard print bikini top and bottoms, letting them fall down to the ground. As I sat on the edge of the bed, completely naked except for the little pink chastity cage, I reached over to grab the midnight blue lace thong, then put both my feet into it and pulled the thong up to my knees. I had to stand to pull it up further.
The thong was a lot tighter than the bikini I had been wearing earlier in the day, and although it still managed to fit my locked clitty, I could feel the lace squishing it. I quite liked the feeling of the lace riding up in between my ass cheeks, and as I went to inspect my ass in the mirror, I heard Lexi compliment me.
“Olivia, your ass looks so pretty framed by that thong! Once we get you in the gym, there’s going to be a real competition for who has the best ass on the superyacht!”
I blushed at Lexi before responding, “Awww thanks. You know you’re pretty hot yourself.”
She just giggled back at me, and I grabbed the lace bra and went to put it on my chest. I was flat-chested, but because the bra was a push-up, it managed to make me look as though I did have the smallest amount of cleavage, which I liked. Finally, I shimmied my body into the short burgundy dress.
I stared at myself in the mirror and thought that I looked just like a hot girl you would see in a nightclub. The dress was quite tight-fitting, and the hemline slit gave a good sneak peek of my hairless thigh. Somehow, the burgundy colour brought out the blonde in my shoulder-length hair even more.
Whilst I had been so engrossed in getting dressed, I hadn’t paid any attention to what Lexi had been doing. Now she was standing next to me in a sparkly skin-tight mini-dress that barely covered her panties, holding two sets of heels.
She handed me one pair and said, “I figured for your first time, we can start you off with some wedged heels.”
They looked cute, so I sat back down and strapped my feet into them. Having never worn high heels before, it took a while to get used to balancing in them, and as I struggled up the stairs with Lexi and back onto the rear deck, I wondered if I ever would.
Don and Mistress Bella were already sitting down at the table by the time we got there. We ended up having quite a nice supper, eating and drinking wine, all the while being waited on by the two Latina stewardesses. As we were nearing the end of our meal, two of the crew appeared on the rear deck. Both men were black and seemed to be in their late 30’s to late 40’s.
Don spotted them immediately and, staring at the men, addressed me. “Olivia, let me introduce you to the superyacht’s captain and his first mate. Captain Kirk and I go back a long time, and we picked Scott up in Jamaica a few years ago. Ever since then, they have done an amazing job sailing us around the world!”
I smiled at both men before Don resumed, “You know, Olivia, when I was young and starting my career, I vowed to myself that one day I would be rich. And when that day came, I was going to help my fellow black man succeed. That’s why on this boat, I only hire brothers.”
I could feel myself blushing for some reason.
This time, Mistress Bella chimed in with her French voice, “Olivia, as a sissy, I am sure you will soon come to understand that black alpha males are at the top of the pecking order in life. That is why, for the after-dinner entertainment, I want you and Lexi to suck the dicks of Captain Kirk and Scott.”
I spun my head to Lexi, who was sitting next to me, and thought in a semi-panicked stare at her, Fuck, am I going to have to do this in front of everyone?
Thankfully, she smiled back at me, offered her hand, and said, “Don’t worry, Olivia. Follow me and do as I do, and you’ll be amazing.”
I grabbed her hand and stood up from the table. Lexi and I strutted over to Captain Kirk and Scott, the first mate. Lexi chose the captain, leaving me standing face-to-face with Scott. Looking to my right, I saw that Lexi was already squatting down in front of the captain and reaching into his trousers.
Sensing my hesitation, Scott gave me a little encouragement. “Don’t worry, baby girl. You’re going to enjoy this as much as I will.”
I looked up into his dark eyes, bit my lip, and squatted down. I had to grab hold of his strong, thick legs as I struggled to balance in my heels. My face was now inches away from his crotch as I slowly unzipped his trousers and reached in. I could feel he was already hard as I grabbed hold of his meat and tried to pull it out. Scott was too big to fit through his zipper, so with my spare hand, I unbuttoned his trousers. Out flopped his large black cock.
I had to take a moment to admire his big, straight, rock-hard black cock. I could barely wrap my hand around it. In my periphery, I could see that Lexi was already bobbing her head up and down on the captain’s cock. So, taking her lead, I lined Scott’s black cock with my mouth and wrapped my lips around his tip.
His bell end was forcing my mouth wide open as I ran my tongue along it and savoured the moment. I could taste some of his pre-cum on his cock and was amazed by how different his seed tasted compared to Don’s. With my hand still gripping the base of his black rod, I pulled my mouth off it and rested his cock on top of my face as I looked up at Scott. With his big balls pressing against the bottom of my chin, his big black cock was longer than the size of my head. I stuck my tongue out and started licking his cock like a lollipop up and down.
I had managed to get Scott’s black python nice and wet now and decided to give sucking on his dong another go. I took as much of him in my mouth as I could. I was stretching my mouth as I felt him prodding the back of my mouth as I went back and forth. There was still so much of him that I couldn’t fit into my throat, so eager to please Scott, I began jerking the base of his rod off as I worked up and down on the top half of him.
I was lost in the moment and loved having his black dong in my mouth. At some point, I could feel his hand on the back of my head. Each time my mouth went down his pole, I could feel his hand pushing me further and further onto it. His thick black cock was poking further and further down my throat. Finally, Scott had pushed my mouth and head all the way down to the base of his black monster. He was holding my head buried tight in his pubes.
I could feel them tickling my nostrils, and with my throat being stuffed, I was struggling for air. I began choking, all the while he still held me in tight as my throat convulsed around his thick cock. Finally, he let go of my head, and I pulled back, gasping for air. I had to grab hold of his wet, slobbery dong to balance myself squatting in heels. I had accidentally slobbered on my chin in the moment, too. I scooped it up and began jerking him off, still trying to catch my breath.
Still jerking him slowly, I lifted his rod to reveal his two large and droopy balls. Each one was bigger than both of mine combined. I had spied Lexi sucking on the captain’s balls earlier and wanted to give it a try, so I took one of Scott’s balls in my mouth. He must have liked it, as his dong jumped a little as I sucked on his gobstopper and continued jerking his slobbery shaft. I popped one out of my mouth and began sucking on his other large black testicle.
Fully recovered from choking on his black monster, I took him back in my mouth. Having already stretched my mouth and throat, I was finding it easier to take more of his pipe. I was vigorously sucking on his black dong.
I hadn’t noticed, but whilst Lexi and I were busy sucking dick, Mistress Bella had stood up from the table and was now standing between each of us.
“You sissies are doing so well,” she purred in her French accent. “When the Captain and Scott cum I want you two to swallow all of your prizes.”
With that, she grabbed hold of the back of each of our heads and held them steady. Scott took the opportunity to begin fucking my face. I had nowhere to move, as his long black cock went from tip to base, slamming down my throat, with his giant testicles banging against my chin.
His cock was somehow getting harder and bigger. Finally, Scott stopped ploughing my throat and held the top half of his veiny black python in my mouth as he jerked the bottom half himself.
He began shooting his load into my mouth, at such force I tried to recoil my head, only for Mistress Bella to hold me steady. Scott’s load was filling my mouth up, as I gulped what I could to make space for more of his cum to fill my mouth up.
Once he had stopped cumming he pulled out of my mouth, allowing me to savour his seed. Somehow his was a lot sweeter than Don’s load, which I had eaten out of Bella’s pussy earlier in the day. I gulped down the last of his spunk before taking his softening black cock into my mouth to clean him up. Only then did I realise my little clitty, that was locked in the chastity cage, underneath the thong I was wearing, was rock hard. I had been so engrossed in sucking Scott’s cock that I hadn’t realised how much it had turned me on.
Scott helped me stand back up as I said, “Thank you. You know you were right, I did enjoy sucking your dick.”
I had completely forgotten about the audience when I heard Don clapping. “Well done, Lexi and Olivia! That was very fun to watch. Although all this excitement has gotten me needing a release again. Lexi, come to me.”
As she strolled over to him, Bella grabbed hold of my hand and smiled at me. As soon as Lexi was next to Don, he smacked her ass and began feeling up underneath her sparkly pink mini dress, before standing up.
“You’re coming downstairs with me,” he spoke again as he grabbed her waist and walked inside with her.
I was still standing on the rear deck in elated exhaustion when Mistress Bella squeezed my hand and whispered into my ear with her sultry French accent, “You were very good at that for a beginner sissy, Olivia. However, pleasing men with your mouth is only half the job. Come with me, I have something else to teach you.”
Bella guided me back inside and downstairs to my new room, which I shared with Lexi. I hadn’t paid much attention to what she had been wearing during dinner, but as I followed her, I was admiring the way her curvy ass moved in her long, flowy white and blue embroidered dress.
Standing next to the dresser in the room, Mistress Bella pushed the straps of her dress off her shoulders as it fell to the ground. Underneath, she was almost completely naked, revealing her round, tanned breasts. Around her crotch, she wore a strappy harness.
Reaching into the dresser drawer, she spoke again. “A sissy must know how to make a man cum with her ass.”
She pulled out a dildo that must have been around the same size as Scott’s big black cock, before attaching it to her harness. “Now come and lube this up with that ever-so-good mouth of yours, sissy.”
I was about to kneel in front of her when she wiggled her finger. “First, I want you to take that dress off, sissy girl.”
I willingly obliged and stepped out of it to reveal to Bella the midnight blue lace push-up bra, with white trim, and matching thong I had been wearing underneath.
“Very cute,” she complimented me. “Now kneel and get this wet.”
That was all the encouragement I needed as I obliged her. Before I had the chance to take the big dildo in my mouth, she slapped me across the face with it, then grabbed my hair and impaled the dildo into my face. My throat was already worn in by Scott, so this time around, I had no difficulty deep throating the dildo. She kept ploughing it down my throat for a few minutes before letting go of my hair, allowing me to come up for breath. Not wanting to disappoint, I buried the long dildo back into my throat and held it at the base for a moment. I could smell the sweet scent of her pussy as I looked up at Mistress Bella. From this angle, she looked glorious, with her large breasts, as she stared down at me
Finally satisfied I had lubed the dildo up enough with my saliva, she beckoned me to get on all fours on top of the bed. Bella yanked down the midnight blue thong that had been covering what little modesty I had, then I heard a bottle cap click open and turned around to see her squeezing a bottle of lube onto her fingers.
Staring at my ass, she spoke. “Make sure you enjoy this, slut.”
I had never been called a slut before, but it made me feel ever so naughty. Then I felt a lubed-up finger press against my virgin ass. She didn’t have to apply much pressure before I felt her finger wiggling around inside of me. It was a very foreign sensation that was getting my locked clitty tingly. Before long, she had two fingers inside of me, loosening up my hole.
“I think you are ready for me now,” Bella remarked, before pulling out her fingers.
I turned around to see what was going on and saw her lining the strap-on up with my ass. Before this evening, I had never even had a finger inside of me, let alone a huge dildo. I could feel its large head pressing up against my lubed-up hole. This was noticeably bigger than the fingers she had just had inside of me.
I did my best to relax as I felt the dildo pressing inside of me, inch by inch. I had to bite my lip from the mild pain of having my asshole stretched out by the big, thick dildo. I could hear Bella purring soothingly to me as she grabbed hold of my hips and pressed further into my ass. Before I knew it, I could feel the balls on the dildo pressing against my gooch, and her warm hips pressing against my ass. I had taken all of the big dildo, and I was amazed it all fit inside of me.
I didn’t have long before she pulled it completely out of me. I had this weird feeling of emptiness before she began pressing it deep into me again, this time a little bit quicker. Bella kept on burying the strap-on into me before taking it out until my asshole was finally used to the size of the dildo, and the pain had subsided. Now she was ploughing in and out of me, slamming into my ass cheeks. The feeling was amazing, and I was loving it so much I was now pressing my ass back against her thrusts, which only encouraged Bella to fuck my ass more ferociously.
She pulled the strap-on out of my ass and signalled me to lie on the bed with my legs up in the air. I could see her naked breasts bouncing about as she clambered onto the bed between my legs.
“You horny little sissy slut. I knew you’d love getting fucked like a girl. God knows you could never please anyone with that puny little clitty of yours. It’s nothing like a real man’s cock,” she remarked, before slamming the large, heavy dildo down on my little chastity-locked clitty.
I screamed out in pain from having my swollen little locked balls whacked. She must have liked my reaction, as she did it again with more force this time. Whilst I was whimpering from the pain, Bella grabbed hold of my thighs in the air and ploughed the large dildo into my ass. Suddenly, I was full again and could feel her pressing up against my prostate. I lay there in ecstasy, mesmerised by her swinging, bouncy breasts that moved in time with each thrust. Imagining I was touching hers, I started playing with my nipples underneath the lace bra I was still wearing. Then she grabbed hold of my swollen, locked balls and started squeezing them as she kept fucking me hard.
I don’t know how long I lay on the bed watching her fuck me senseless, but suddenly the bedroom door swung open to reveal a naked and sweaty Lexi.
Bella paused, whilst the strap-on was still in my ass, turned and spoke to her. “Did you have fun with Don, my dear?”
“Yes, Mistress,” Lexi smiled back at her.
“Did he breed you?” Bella asked.
“Yes, Mistress,” Lexi once again replied.
“Good girl. Now sit on Olivia’s face and get her to clean you up.”
Bella resumed fucking me, as Lexi climbed onto the bed, placing a foot on either side of my head and lowering her ass onto my face whilst pulling her cheeks apart. I could see some of Don’s seed oozing out of her used hole already, and instinctively I began lapping it up. As I lay there being pounded by Bella, I worked my tongue in and around Lexi’s ass as I tried to eat as much of Don’s tasty cum as I could find.
When Lexi’s ass was finally clean of cum, she pulled her ass off of my face to reveal her now erect girl cock. I opened my mouth to signal to her, and she slowly put the tip of her dick into my mouth. Mistress Bella’s thrusts from fucking my ass were pushing my head further onto Lexi’s cock. I couldn’t believe I was getting my ass fucked by Bella, whilst at the same time sucking the dick of my new sissy friend, Lexi.
She couldn’t have lasted long, as before I knew it, Lexi was shooting her cum down my throat. Compared to Scott earlier, I was easily able to swallow her load in one. She collapsed on the bed next to me, as Bella’s rampant thrusting eased to an eventual stop and she pulled the strap-on out of my loose ass.
“Well done, Olivia,” Bella panted, also exhausted. “You took my strap-on like a true slut tonight. You’ll be ready for a real cock in no time.”
With that, she climbed off the bed, taking the dildo out of her harness and sticking it to the top of the dresser before leaving Lexi and me alone, and used, on the bed. As we lay there cuddling, I thought back on my crazy cum filled first day on the superyacht.
That night, Lexi and I fell asleep in each other’s embrace.
