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The Sissy And The Superyacht Chapter 5: Olivia Meets Don's Business Partner

"Mistress Bella makes some adjustments to Olivia's body, then Olivia learns what's better than one big black cock"

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Author's Notes

"This fictional multi-chapter story follows the life of a straight white boy who falls down the sissy rabbit hole with the help of a few acquaintances met along the way. In Chapter 4, Olivia went to her first gloryhole, then got bred by Don. Chapter 5 picks up a month and a half after Chapter 4."

It had been a couple of weeks since my excursion to the gloryhole and outfit shopping in Positano, which resulted in my first breeding by Don, the older black Adonis who owned the superyacht. I had settled into my new sissy life well and finally felt like I had found my place in life. I hadn't worn boys' clothes in over two months and loved all the sexy, skimpy outfits I got to wear daily as I sunbathed and worked on my now prominent bikini tan lines. I had never been a muscular guy, but when I looked in the mirror, I was noticeably skinnier and completely hairless below my eyebrows. This was partly due to Mistress Bella putting me on a restrictive diet, consisting of small meals and large amounts of semen, and partly due to the gym workouts I had been doing with my roommate, Lexi. She was also a sissy girl who had been living on the superyacht a year or two longer than I had. Mistress Bella had put Lexi on hormones, which were slowly turning her into a real girl.

After Positano, we had sailed all over Italy and Greece and were due to land in Mykonos tomorrow. When I first joined the superyacht, Mistress Bella and Don had forced me to suck the dick of the boat's First Mate, Scott, for their entertainment. Scott has an athletic black guy who was five to ten years older than me. What had begun as Mistress Bella's way to humiliate me had turned into a secret fling. Pretty soon, whenever Scott and I could get some alone time, I was blowing him, or he was fucking me. We had had a few close calls, but as far as we knew, no one else on the superyacht had any idea about our extracurricular activities. 

That was one of those moments. It was mid-afternoon, and I was alone with Scott on the brig, bent over next to the helm. I had been wearing a white bikini with cherries printed all over it, but the thong bottom was now around my ankles. Thankfully, the top was still on, giving me some modesty. I was holding onto the control panel to steady myself, as he ploughed in and out of me, prodding my prostate with his sizeable, veiny, black dong. I could feel the beginnings of something building inside of me. Was I finally about to have my first sissygasm? I looked beneath me to see my little clitty, locked in an equally little pink chastity cage, swinging in time with Scott's animalistic thrusts. I had been locked up since the first day I set foot on the superyacht, with no release. Mistress Bella had told me that if I ever wanted to orgasm again, it would have to come from anal stimulation. I could feel it slowly building in the bottom of my stomach.

Suddenly, my bliss was broken by Scott pulling his dong out of my ass, grabbing my shoulders and shoving me onto my knees. 

"I'm about to cum, Olivia," he panted. "Give me your mouth so I can hide the evidence."

Eagerly, I did as he commanded, and wrapped my pink, glossed lips around his juicy black bell end. I could taste my ass on his manly cock. The smell was intoxicating as I looked up into his eyes, sucking his tip while he ferociously jerked his glistening shaft. His face clenched up a little as his veiny dong exploded in my mouth. His velvety salty seed instantly coated and filled my throat. Although I had only been a sissy for two months, I liked to think I had become a connoisseur of different men's cumshots, and Scott's was definitely the tastiest I had tried to date.

He had finally stopped shooting his seed into my mouth, so I pulled my lips off his tip, and, maintaining eye contact, opened my mouth, smiling to show him my full mouth. Before it could start dribbling out and make a mess of my makeup or bikini top, I swallowed all his tasty load. I grabbed hold of his softening pole and licked it clean.

Finally, Scott offered me a hand up and spoke, "Damn, Olivia. You really are the perfect sissy slut."

I giggled a little as I bent over to pick up the cherry-printed white thong bikini bottom and started pulling it up my skinny legs.

Scott continued, "You know all the rest of the crew are talking about at the moment is how much they want to fuck that sexy ass of yours?"

He smacked my ass just as I finished pulling the bikini thong on.

Coyly, I turned around to Scott and replied, "Well, maybe I should see if I can relieve the stress of the deckhands."

Now Scott was chuckling, "No chance, sissy. Your ass is mine. I'm the only one who gets to fuck you behind Bella’s and Don's back."

With that, he picked me up and planted a firm kiss on my lips. 

As he let go, I spoke up, "I should probably get back to Mistress Bella and Lexi, or they'll wonder where I got to."

Scott nodded understandingly as I walked off. I snuck out of the brig and back onto the main floor of the yacht. As I walked through the inside, I spotted my reflection in a mirror. Thankfully, my lip gloss hadn't smudged at all, and as I turned around to inspect my ass, I was grateful that there was no visible evidence I had had a big black cock in there a few minutes ago.

Mistress Bella and Lexi were lying together on the front deck of the superyacht. Both looked sexy for very different reasons. Bella had large, perfectly round, and naturally perky breasts, with a tight body. She was the epitome of what a female sex goddess should look like. Whilst Lexi, with her small breasts and tiny bulge in her bikini bottoms, made me think of what I hoped my body could look like with time and practice. We spent the rest of the afternoon chilling together and soaking up the sun.

Later that evening, after we had all finished supper, Lexi and I were back in our room and stripping down for bed when I caught her staring at my body with a certain hunger in her eyes. As soon as she clocked I had noticed, Lexi slowly came over to me, embracing my body and gently squeezing my ass. 

"I have to say, Olivia, you truly have transformed into one sexy sissy girl," she whispered in my ear.

I blushed a little as I replied, "Awww, thanks, babe."

"Just looking at that pretty body of yours is making me horny," Lexi continued. "Will you help me out a little before bed?"

Catching the drift of her innuendo, I stared down at her hairless, limp girl cock. From what she had told me, Lexi had been taking oestrogen ever since Mistress Bella had introduced her to the sissy life.

I licked my lips a little before responding, "Of course, Lexi."

Before I could say any more, Lexi had pushed me back onto our bed. As I lay there staring up, watching her climb onto the bed, she placed each of her knees on either side of my head, then lowered herself onto me. Her limp girl cock slotted effortlessly into my mouth, as I could feel her little breasts squishing into my abdomen.

I began sucking on her limp girl cock, tugging it with my lips. I could feel her growing in my mouth. Compared to Don's or Scott's big black cocks, Lexi's was easy to take. At the other end of my body, I could feel her sucking on my swollen chastity-locked balls and slapping them too. It had been two months since I had last cum, and my life was a perpetual state of horniness, where I would do just about anything for the chance of relief.

Lexi was hard now and pumping in and out of my mouth with her girl cock. Hard, she must have only been about four inches long, but she made up for it with the vigour with which she was fucking my face. I could taste her salty pre-cum oozing out of her girl cock as I gargled on it. She kept the ploughing up for a minute before pulling back and falling back on herself in bed.

Lexi's little hard girl cock was glistening in my saliva, as she frustratedly spoke, "Damn, I just can't cum like this. I need something in my ass, too."

Still mesmerised and staring at her glistening girl cock, "I'd love to be able to fuck your ass, babe, but I can't with this little puny thing," I replied as I signalled down to my tiny pink chastity cage locked clitty, "Do you have a dildo or anything I could use to help you with?"

Lexi's eyes lit up. "Good thinking, gurl! I have just the thing for us to use."

She jumped off the bed before reaching into a cupboard and pulling out a large double-ended dildo. Lexi gleefully wagged it in the air before throwing it at me, still lying on the bed. The double-ended dildo landed on my torso with a thud. The pole reached from my chastity cage up to my nipples, with a bulbous head on either end. I lay there engrossed by the dildo on top of me, as Lexi re-entered my periphery, holding a bottle of lube.

We both applied some to our asses and the shared pole before getting on our knees, pointing away from each other. Lexi began inserting her end of the dildo into herself first as I looked on eagerly. The first few inches slipped in easily, and I could see from her facial expressions how much she loved having a dick up her ass. Once she had taken a few more inches, Lexi signalled for me to start backing onto my end of the double-headed dildo.

Lexi held the lubed-up pole steady as I could feel it pressing against my rosebud. Slowly and steadily, I pushed the fake cock into my sissy pussy. Thankfully, I was still loose from Scott fucking me earlier in the day, so it wasn't painful at all, and it was pure pleasure from the beginning. We both began bouncing on the pole, moaning, and before long, we had engulfed the double-ended dildo in our two sissy pussies. I could feel and hear our asses slapping together, as the dildo inside of me radiated waves around my body. As I looked underneath me, I could see my tiny pink chastity cage swinging helplessly, and in the background, I could see Lexi jerking her little girl cock. 

Suddenly, Lexi stopped thrusting herself onto the fake cock and panted, "Wait... I want to be able to see that sexy body of yours when I cum."

Slowly, with the double-ended dildo inside of us, we turned over so our asses lay on the bed and our clitties were up in the air. Lexi threw one leg over mine, so that we were entwined, then started gyrating on the pole within her. Taking her lead, I copied her, as well as gripping my chest and pinching my nipples. 

At this angle, the dildo was prodding into my prostate, and I could feel something building inside of me again. My gyrations on the dildo were causing pre-cum to begin leaking out of my locked clitty, as I moaned in heaven. I almost forgot Lexi was there as she, too, was fucking herself in ecstasy and jerking on her girl cock. 

I was so focused on fucking myself that I was brought back to reality when Lexi shot her load all over my pink chastity cage. She groaned as she slowed the gyrations on the dildo, and more cum oozed out of her girl cock. At that moment, I forgot about myself and pulled off the dildo that had been inside of me. Knelt over on the bed and took her softening girl cock in my mouth and began milking the last of her cum. With my spare hand, I grabbed hold of the dildo still inside of Lexi and slowly pressed it in and out of her ass, hoping to get more cum, before finally pulling it out altogether.

We lay there for a minute, hot and sweaty, coated in a mixture of lube and our own juices, before gaining the energy to go shower off together. As we cleaned each other in our shower, I reflected on how fun it was to have Lexi as a roommate and how she was the perfect sissy mentor. Once out of the shower, I put on a champagne-coloured satin nightdress and climbed into bed with Lexi.

The next morning, we were woken up by Mistress Bella switching on our bedroom lights, "Good morning, Sissies! I hope you had fun last night, as the whole yacht could hear you moaning like sluts!"

Both Lexi and I were still half asleep but beginning to blush.

Continuing in her husky French accent, Mistress Bella spoke, "Anyway, we have just pulled into the port of Mykonos. Lexi, you're going to have to entertain yourself for a few hours today. Olivia, I want you up on the rear deck in an hour. We have an errand to run and need to be back on the superyacht for mid-afternoon, as we have a visitor then."

We all paused for a moment before Mistress Bella, rather shrilly, shouted this time, "Out of bed now, girls!" then clapped her hands.

Not wanting to annoy her anymore, I jumped out of bed and dropped my nightdress to the ground before heading to the bathroom. By now, I had gotten pretty good at my morning routine. I would shower, shave and scrub my body. Once out of the shower, I would moisturise myself, and as that soaked in, would apply my makeup. Once done in the bathroom, I went back into the bedroom to get dressed. As I opened up my lingerie drawer, a red lace thong caught my attention, so I grabbed that and pulled it on, making sure that the front of it cupped my little pink chastity cage nicely. From another drawer, I pulled out a denim micro skirt and shimmied that up my legs. As I looked about for a top to wear, I found a red halter-neck crop top, which I thought would match the thong I was wearing.

Once dressed, I inspected myself in the mirror and was pleased to see the long blonde-haired slut staring back at me. My skirt barely covered my ass cheeks, and the top was as alluring as it was sexy. I blew a kiss to myself in the mirror before stepping into my pink flip-flops, before grabbing my sunglasses and heading upstairs.

Mistress Bella was already on the rear deck, chatting to one of the deckhands called T'Shaun. Don, the owner of the superyacht, had a policy of only hiring black men, and T'Shaun was no exception, standing at 6 feet and 6 inches, made of pure muscle. They both stared up at me as I approached.

"Cute outfit, Olivia," Bella congratulated me. "I only have one amendment to make to it, though."

With that, she pulled a large gold metal butt plug from her handbag and waved it at me.

"Go on, drop your panties so T'Shaun can put this in you," Mistress Bella continued.

I blushed a little, as he and I had never spoken to each other before, and now I was meant to let him shove that large gold butt plug up my ass. Finally, I nodded to Mistress Bella, then turned around and hitched up my denim micro skirt, pulled my red lace thong down to just below my butt and bent over expectantly waiting.

T'Shaun's eyes widened as I revealed myself to him and didn't break contact with my ass even as Mistress Bella handed him the gold butt plug. He spread my ass cheeks apart before spitting into my asshole, which had recovered from the two ass fuckings I had received the previous day. Then he dribbled a load of saliva onto the gold butt plug and began pressing it into my ass. The gold metal was cold against my sphincter as it stretched the muscle. T'Shaun didn't stop ramming the plug in until I felt my ass gobble the last of it in.

As he stepped away from me, I stood back up and rearranged my outfit to cover myself up again. Aside from the plug stuffing my ass and adding to my general horniness, it felt so heavy inside of me, which made me wonder if it was made of real gold.

Mistress Bella just nodded at me before walking down the gangplank to shore and signalling me to follow. As I walked past a smiling T'Shaun, I could still see him ogling my body, and when I looked closely, I saw the outline of a monster erection under his shorts. 

On land, there was a quadbike already waiting for the two of us, which Mistress Bella was already climbing onto to drive. I squeezed in to sit behind her, and in the process of sitting down, I could feel my denim micro skirt begin to ride up a little. As soon as Mistress Bella ignited the engine, the quadbikes' vibrations began hammering through to the gold metal butt plug currently stuffed in me. Not paying any attention to me squirming behind her, Bella pulled out of the harbour and onto the main road.

By the time the quadbike pulled into the side of the road, twenty minutes later, I knew I was in trouble. The plug had been vibrating against my prostate the entire time, and when Mistress Bella climbed off the bike and turned around to face me, she could see that my clitty had leaked out of the chastity cage and had soaked the front of my red thong with pre-cum.

In her French accent, she almost laughed at me. "Oh, honey, look what you've done to yourself. So pathetic."

Red-faced from Mistress Bella's humiliation, I climbed off the bike too and pulled my skirt back down to try and cover my modesty. I followed her into an unassuming shop front, which, when inside, turned out to be a tattoo and piercing parlour.

As I was inspecting all the tattoo designs on the wall, Bella leaned over to me and spoke into my ear, "Olivia, I just wanted you to know that you've made amazing progress at becoming a real girl since I locked that little shrimp of yours up two months ago. As a little treat, I thought you might like to get some piercings. Why don't you have a little look around to see if there are any you might like?"

As I looked around the shop for ideas of what I might like, Mistress Bella found the proprietor, a middle-aged Greek man, and struck up a conversation with him. I found a couple of large gold hoop earrings that I thought looked hot, and a belly button piercing, too. Once I had picked out what I wanted, the Greek man signalled me to sit in the chair as he got his equipment ready.

The first ear piercing stung like a bitch, and the pain brought a tear to my eye. As I sat there recovering and preparing for the same to happen to my other ear, Bella continued chatting to the Greek man, although the topic of conversation took a sudden change.

"Would you have guessed that the girl you're piercing right now is actually a guy?" she asked him.

The Greek man turned back to me with a puzzled expression. What was Bella doing? I thought to myself as I blushed from the embarrassment.

She continued in her husky French accent, "Yeah, I caught him sniffing my panties a few months ago, and as punishment, I turned him into this slut sitting before you right now."

I sat there red-faced and humiliated. Part of me had grown to love how Mistress Bella treated me, as I could feel my little clitty straining against the cage, and the heavy weight of the gold plug in my ass, but the other part of me hated the humiliation.

The Greek man did the second piercing, and I flinched from the pain, before he responded to Bella, "Interesting story.... To be honest, if you had not told me, I would have thought she was just a pretty beach bum." He paused for a moment. "A little skinny for my liking, but she's definitely sexy."

As I sat there smiling from his compliment, the Greek man moved to my belly button and lined up the final piercing. The final one stung the most, but I was so pleased with the result. I sat in the chair, staring at myself in the mirror, admiring my new gold hoops and belly button piercing, thinking about how hot I looked.

I was about to stand back up when Bella put her hands on my shoulder and announced, "I think you are ready to be branded as my pet, Olivia."

Then she turned her head to the Greek man, "I want you to tattoo on her ankle the words 'Property of Mistress Bella'."

He nodded, then pulled out his tattoo gun. As the gun began buzzing and etching Bella's tag into my skin, I bit my lip a little but reflected that this felt noticeably less painful than the piercings I had had a few moments before. Finally, he nodded that he was done and put the tattoo gun away. I stood up and went straight over to the mirror to inspect all the changes. The gold hoop earrings really added to the slutty look, and I loved how my new belly piercing brought extra attention to my toned body. I would never have admitted it to Mistress Bella, but I secretly loved her tattoo branding me as her toy.

I was brought back to reality when I heard Bella discussing payment with the Greek man, "Oh, I am so sorry. I must have forgotten my purse," pausing for a moment before giving me an evil wink, "Would you by any chance accept payment in gold?"

In an unexpected nonchalance, the Greek man shrugged. "Cash, gold. It is all the same to me. Show me what you have, and I will decide if it is enough."

I could feel the gold metal butt plug, still in me, weighing me down as I knew what was coming next.

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Bella lifted her hand and signalled me to come over to them. "Olivia, come over here, my sissy girl."

Obediently, I tiptoed over to the two of them, before Mistress Bella spun me around, so I was facing away from the two of them, then hitched up my denim micro skirt, revealing the red lace thong framing my ass and bending me over. Next, she yanked the thong down to the ground, revealing to the Greek man staring in surprise, the gold butt plug stuffed inside me, and my little locked clitty dangling helplessly below.

I could feel Bella's knuckles on either side of the plug as she began pulling the heavy gold plug out of me. I could feel a moment of resistance before it plopped out of my ass. Empty again, I went to stand up and turned to face them and was met by Bella shoving the golf plug into my mouth for me to lick clean.

As Mistress Bella gave the Greek man the gold butt plug, I pulled up my red lace thong from the ground and covered my pink, locked clitty once again, before pulling down the denim skirt.

"Is this payment enough?" Bella asked him.

He didn't even look at the plug as his eyes were transfixed on my body, "Sure, that will do."

Sensing he had other things on his mind, Bella, in her coy French voice, asked, "You seem errr aroused by my pet slut? Would you like her to help you out?"

He just nodded.

Turning to me, Mistress Bella instructed, "Go on, Olivia, show him what you can do with your mouth."

Eager to please, I knelt in front of the Greek man, who a few moments ago had pierced my body and branded me, unbuttoned his shorts, and pulled them down before reaching in with my hand. Nestled between his pubes, I grabbed hold of his rock-hard dick and pulled it out. He was by no means large but a healthy six and a bit inches long and uncircumcised. Pulling back his foreskin, I licked the underside of his tip with my tongue before licking the rest of his tip as I looked up into his eyes.

I could tell how aroused he was as I could already feel him twitching a little. Thinking I could make short work of the Greek man. I took his length into my mouth and began sucking on his dick. I could feel his pubes tickling my nostrils as I bobbed my head to the base of his dick and felt him prodding the top of my throat. I gently cradled his balls as I bobbed up and down a bit more before I heard the Greek man groan out in pleasure. Knowing what was imminently about to happen, I buried my face into his hairy crotch and let him shoot his load straight into my stomach. 

I felt him twitch a few times inside my mouth before he began to soften. Not wanting to make a mess, I sucked his shrinking dick clean before standing up and kissing him on the cheek.

"Expertly done, my slut," Bella congratulated me. "Now we need to head back to the superyacht, or you're going to be late."

We hopped back on the quadbike and sped back to the harbour. I felt noticeably empty without the gold butt plug in me this time, but the vibrations of the engine were still making me horny. It had been a successful outing in my opinion. Three new piercings, one new tattoo and one tasty portion of cum.

In no time at all, we were back in the harbour and climbing back aboard. Lexi was waiting for Mistress Bella and me on the rear deck.

"Oh, Olivia, I love your new piercings," she exclaimed as she hugged me, "And shut up! We've got matching tattoos now."

Lexi then turned to Bella. "You didn't say who the visitor was going to be, Mistress?!?"

Bella snapped back in her husky accent, "No, I didn't tell you, Lexi," frustrated at the commotion she had caused, before continuing, “Keep the noise down. We don't want to disrupt Don's meeting.
Quizzically, I, too, turned around to Bella and meekly asked, "So who is it, Mistress?"

"Don has his business partner aboard. They meet once or twice a year to catch up and make sure everything is in order before they have a little... party, shall we say?"

Still confused, I asked again, "What do you mean by 'party'?"

As she responded, Mistress Bella had that evil grin forming across her lips, "Let's just say his business partner is the reason Don likes sissy girls like you."

Beginning to catch her drift, I stifled a giggle as I nodded.

"Anyway, Olivia, today you are their entertainment," Bella announced. "Go and put something sexy on and then head up to the reception room to meet them. Lexi, if I were you, I'd make myself scarce and hang out in the jacuzzi."

Taking my orders, I headed below deck to get changed, but not before Lexi winked at me and mouthed, "Good luck."

Back in my room, I stripped down to just the red lace thong I was wearing and opened my lingerie drawer. I was already having a great day in my thong, so I figured I should complete the outfit. I had a matching red lace push-up bra, which I strapped on and shuffled around my chest to make it look like I had some small breasts. Next, I clipped the matching suspender belt around my waist and slipped the straps underneath my thong.

I looked in the mirror and thought I looked like a pornstar with what I was wearing and my new piercings. However, the outfit was still missing something. I reached back into my drawer and pulled out some white sheer hold-up stockings. I loved how they felt as I pulled them up my hairless legs. Every time I put stockings on, it always sent a shiver down to my little locked clitty.

I took one final inspection of myself in the mirror and loved how the white stockings accentuated my suntan and really brought out the red in the rest of my lace lingerie set. Thinking quickly, I grabbed some red lipstick and smeared some on to complete the look.

I could feel the butterflies in my stomach, knowing what I was about to do as I crept upstairs to the reception room. As I entered the room, I took a moment to inspect Don and his business partner. Don was a huge, muscular black guy in his late forties to early fifties, who was bald, except for a salt and pepper goatee. Usually, he dressed very casually, but today he was wearing a smart two-piece suit. His business partner must have been around the same age as Don and was also a black man. He must have been about six feet eight inches tall, and although still very muscular, was a little tubbier than Don. He was wearing suit trousers, a waistcoat and a white shirt.

Don and his business partner were coming to the end of their discussion, so I knocked on the open door to catch their attention. Both older black men stopped and turned to face me, standing, wearing nothing but my sexy red lingerie.

The silence was killing me, so in my sluttiest voice, I broke it as I tiptoed towards the two black men: "Heyyy, I heard there were two big, strong businessmen who may need some stress relief."

Turning to his business partner, Don spoke next, "I'd like to introduce Bella's new pet, Olivia."

'Hmmmm," the chunky black partner sighed as he stood up, "Bella has a real gift at turning pathetic white beta bois into sluts."

He was standing next to me now, and I realised quite how huge the business partner was as I could feel his nostrils breathing down on me. I felt like a mouse next to this giant of a black man. His hand reached up to my lacey red push-up bra as he cupped a feel of my chest. His warm hand was the size of a spade. He gently pinched my nipples as I stared back into his eyes and bit my lips. Next, his hand wandered down my body, past my new belly button piercing and the suspender belt, until he grabbed hold of my clitty, which felt tiny in his hand.

"Locked, ahah," he exclaimed, referencing the tiny pink chastity cage I was trapped in, "My favourite."

All I could do was giggle a little as he let go of me and reached around to my ass, as he began gently clapping my cheeks up and down. I turned my head to find Don sitting on the sofa, silently with a smile on his face, watching his friend groping me.

The black giant spoke down at me, "Let's see how good you are at handling a real man."

Catching the drift of what he meant, I slowly squatted down as I stared back up at him and undid the zip to his suit trousers. I could see he was commando underneath his trousers, and I spied the top of a very thick black hose. I began pulling it out, and after three attempts, his soft, long pipe flopped out. My eyes widened as I looked up at his japs eye. With one hand, I grabbed hold of the base of his black cock and wrapped my mouth around him.

I began sucking on his mushroom head as I gently stroked his shaft. I could feel his cock getting warmer as more blood rushed into it, making him firmer. I let go of his manhood and let him flop out of my mouth. As Don’s business partner stood before me with his growing cock dangling, I spat into my hand for lube, then picked up his shaft and began stroking him faster. With his cock poking straight out, I lowered my mouth to his large, low-hanging balls and took one in my mouth. I looked up into his eyes as I sucked his black balls, stroking his hard dong, I could taste his manly ball sweat in my mouth. It felt exhilarating serving such an alpha male. I could feel a shiver of excitement as I knelt before him in red lingerie and felt my clitty straining against the cage.

Lost in the moment, I hadn’t noticed Don moving. He had now taken off all his clothes and was standing next to his business partner. He was smiling down at me like a proud owner as I worked my tongue up from his business partner’s balls along the underside of his black cock and finally up to his tip. 

Don was clearly enjoying the show I was putting on as his dong was already hard. With my spare hand, I grabbed hold of his manhood, spitting on the tip, and gently stroked both men’s big black poles. Dons was still a little bigger than his business partners, but both were easily the size of my forearm. As I stared up at the big black Adonis, I thought about how lucky I was to have them both for myself.

Still holding the business partner’s dong, I moved my lips to the tip of Don’s cock and wrapped them around. As I looked up into his eyes, I felt a sudden pressure on the back of my head as the business partner shoved my head down Don’s massive black cock and into his pubic bone. I knelt in between Don’s legs, throat stuffed and gagging for air, unable to pull off as his business partner’s hand was still pressing me down onto Don’s big dick.

Just as I thought I was going to pass out, he released me, and I pulled up, gasping for air. I stared at Don’s saliva-glistening cock as I knelt in between the two men, recovering and pondering if this was too much black cock for one sissy.

Before I had any more time to think, his business partner announced, “My turn,” then grabbed my head again and shoved his big black pole down my throat.

Whether it was Don being slightly bigger or my throat having been warmed up, it felt easier this time as he buried my face into his groin. He held me still for a moment with his dong filling my throat before he began pumping in and out. His big, heavy balls were slamming against my chin with each pump. I could feel my eyes involuntarily crying from the throat fucking. I even had to grab hold of Don’s meaty, hard cock to steady myself.

Finally, with one more mega thrust of his dong shoving halfway down my throat and his wrecking balls on my chin, he released my head. Not wanting to show weakness or get my throat fucked again, I immediately moved to sucking the top half of Don’s cock and jerking off his business partner’s very wet dick.

Both men seemed sufficiently happy as I took regular turns with each of them in my mouth as I jerked the other one off. After a few more minutes, Don picked me up by my waist and laid me down on the coffee table, facing up to the ceiling with my white stocking-covered legs in the air. Don disappeared for a few moments as his business partner knelt and pulled my red lace thong off me. I was now naked except for my red lace push-up bra, matching suspenders, white stockings and tiny pink chastity cage.

As he sniffed my thong as he stared down at me, the business partner remarked, “So cute and girly…… except for that.”

Before I had time to realise what he was referring to, he had slapped my swollen, locked, hairless balls. I hadn’t cum in over two months since the Mistress Bella had first locked me up. That, combined with the slap, felt like a hammer had been dropped on them.

As I whimpered from the pain, the business partner plonked his black, meaty manhood down onto my tiny, locked clitty and balls. 

“Don’s a caring alpha,” his business partner remarked as he slapped his black python against my sissy cage. “I, however, take great pleasure in destroying pathetic beta sissy girls.”

With that, he lined his saliva-stricken pole up with my ass and began ramming himself in. I screamed out in pain as he impaled the top of his shaft into me.

“Yo!” Don had reappeared and had caught both of our attention. “At least use some lube on my new bitch." He threw a bottle, which his business partner easily caught. “Otherwise, you’re gonna split Olivia in half.”

His business partner pulled out of my ass so that only the tip of him was still inside me before squirting lube all over himself. Then he grabbed hold of my tiny pink chastity cage, squeezing hard, and impaled himself into my ass. The lube helped a lot compared to his first attempt, but my sphincter was still struggling to adjust to his girth.

While his business partner was still pressing himself into me, Don was now standing over my head. From beneath, his enormous, big black cock seemed to block out the lighting. I saw his cum-filled testicles and, eager to please, sat up a little so that I could suck on one of them.

As I lay on my back with Don’s huge black pecker lying on my face and his balls in my mouth, his business partner had finally bottomed out in my ass. I was having a sensory overload from having my ass stuffed, chastity-locked clitty being squeezed, being unable to see from the huge cock on my face and a mouth full of alpha balls.

His business partner began pulling out before promptly invading my ass again. With each thrust, my wails were being muffled by Don’s balls. After a minute or two, my asshole had loosened up a bit, and with the pain subsiding to the point of pleasure beginning, I plopped Don’s balls out of my mouth and took his tip into my desperate mouth.

As I milked his bell end, I stared down at my lingerie-covered body and the hulk of a Mandingo ravaging me in between my legs and realised I had never had to satisfy two men’s cocks before. It was crazy to think how different my life was before I met Mistress Bella.

Don’s black dong slapping my face and his business partner pulling out of me brought me back to reality. I suddenly felt so empty.

With one last dick slap, Don commanded me, “Turn over, sissy. It’s my turn now.”

Eager to please my black master, I flipped onto my belly, with my ass hanging over the edge of the coffee table and my head at the other end. Don and his business partner had also swapped sides.

Wanting to feel full again, I jiggled my ass slightly to tease Don. He grabbed hold of my cheeks and spread them apart. I felt his spit hit my already stretched sissy asshole. Then, without mercy, he shoved himself all the way into my ass. 

Somehow, he was even girthier than his business partner. As I lurched forward from the surprise anal stretching, his business partner grabbed hold of my long blonde hair and forced his black cock into my mouth.

Don’s thrusts were pushing my mouth further down his business partner’s cock. On his pole, I could taste the intoxicating mixture of my ass juices and lube.

Holding my head still, his business partner now began pushing his black cock down my throat. I had nowhere to escape as I was being impaled with BBC at both ends. They were both pumping me in rhythm, creating an airtight lock on both their cocks.

As his business partners’ black balls wrecked my chin, I could feel Don’s testicles bashing against my puny, swollen, chastity-locked balls. In addition to destroying my asshole, his animalistic fucking was ramming against my prostate.

I could feel my body tensing and beginning to convulse around the two big black cocks, spit-roasting me. I tried to let out moans of pleasure, but my throat was stuffed, muffing any noise on my part. It has been over two months since I last came, and I could feel something big about to detonate deep inside me.

With an explosion of sensation, my first sissygasm hit me like a train. Every cell in my body went tense and felt fuzzy. My body felt on fire as I could feel my locked clitty shooting out rope after rope of sissygirl cum. 

As the most intense orgasm I had ever had began to subside and I re-entered reality, I realised that Don and his business partner had no idea what had just happened to me. They were still busy rearranging my insides.

Don grabbed hold of my waist just below the red lace suspender belt I was still wearing, and with his huge pole still in my ass, picked me off the ground. In that moment, his business partner’s cock fell from my mouth, and I looked down to see a wet puddle on the coffee table of my cum, which had leaked from my clitty. His business partner picked me up by the shoulders and slammed his cock back down my throat. Like the black alpha males they were, they kept ramming my insides, as I was left suspended in the air by the huge black cocks stuffed inside both of my holes.

I was trying my best to keep in the air as they worked their magic, but his business partner kept slipping from my mouth. Thankfully, Don grabbed hold of my long blonde hair as he kept thrusting from behind. As he held me in position by my hair, his business partner picked up the ferocity of his face fucking even more.

"Fuck. I'm gonna unload in the bitch," was all he managed to get out.

On cue, his black python spasmed in my mouth and throat as he shot torrent after torrent of his silky seed straight into my stomach. Don was still thrusting me onto his business partner's cock as he finished cumming, and I milked the last of his cum from him.

His business partner let go and pulled his spent weapon from my mouth. My hands and face collapsed onto the coffee table as Don ploughed my sissy ass. My face landed in the cum I had shot onto the table earlier as Don fucked me harder than I had ever been fucked before. 

I could feel his huge balls swinging into me, and I began to feel him smashing into my prostate again. Then, with one loud and deep grunt, he shoved himself into me one final time, almost pushing me off the coffee table, and unloaded into my sissy womb. His cum flooded my insides, and I felt the warmth overflow my body.

He pulled out immediately and collapsed onto the sofa next to his business partner. 

As I struggled to regain myself, the two stewardesses and Mistress Bella walked into the room. Two stewardesses poured each of them a whiskey as they looked down at me in a puddle of cum and half-destroyed lingerie disapprovingly.

In her authoritative French accent, Mistress Bella announced, "Well, gentlemen, I think the two of you have fucked the last essence of a man out of Olivia."

Turning her attention to me, she said, "Strip out of what you are wearing and give it to them," signalling to the judgmental stewardesses. "Lexi is out back. Why don't you go and recover with her?"

I struggled to my feet and peeled the cum soaked red lingerie off my body before putting my wet bra and stockings in their hands and hobbling out of the room. 

I could already feel Don's spunk leaking out of my ravaged asshole as I found Lexi in the jacuzzi and eased myself into the hot, bubbly water.

With a knowing smile, Lexi handed me a glass of champagne and whispered, "You're a woman now."

Published 
Written by Sissy_Ami
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