Jack and Jill Pt. 05: Thailand

The decision to move to Thailand was a big one, but Jill was glad that they had done it. Here they could live out all of their sexual fantasies in total freedom, without judgement or harassment. She had completed Jack's feminisation by insisting he had breast implants when they arrived, but that was months ago and they were all healed now. She loved to grab them and squeeze his nipples hard while she fucked him with her big strap on. She knew he liked them too, she often caught him looking at them in the mirror and touching them. They had definitely helped him to get a job in the Lady Boy bar where they both worked. She finished touching up her lipstick and straightened her skin tight PVC dress. She was ready. She went through to the bedroom and helped Jack into his dress, his breasts where big and he always wore dresses that showed off his cleavage. Wig, stockings and heels finished the slut look. She took a generous amount of lube from the bottle and bent him over. Thrusting two fingers deep inside him she worked a third and fourth finger in.

'There is a crew of American sailors coming to the bar tonight and they are all black! Need to make sure you are ready for a good arse pounding!' she smiled.

'Mmmmm...' he purred wriggling on her fingers, she loved what a total anal slut she had made him. Giggling they left their apartment and headed for the bar.

He loved his new job as a sissy whore, every night he was fucked senseless, gang banged and cover in cum. It was sissy heaven, even better his wife Jill was running the bar and she took enormous pleasure pimping him out. Especially to big black men with big black dicks. He watched as she marched off behind the bar and took control of the place. He wandered over to the other sissy's and gossiped while they waited for the sailors to arrive. He had a drink and then went to the toilets to do a line of coke, he thought it would be a long night and needed a pick me up. When he came out Jill was waiting for him.

'The sailors have requested that you be caged and they want me to watch, somehow they found out we were together and like the idea of fucking a sissy in front of his wife. Perverts!' She laughed and he followed her into her office.

He pulled down his panties so that she could attach the device, he loved the feeling of being caged, it kept his cock limp and dripping for hours. He pulled up his panties over his now caged cock, straightened his dress and his cleavage and followed Jill out to the sailors. He smiled, they were all big boys, he hoped their cocks where as big as they were. He licked his lips automatically. Jill went away to arrange drinks while he flirted with them outrageously, running his hand over their trousers and feeling the outline of their cocks. He felt their hands all over him, he felt like such a slut and he loved it...

She watched him flirting from the other side of the bar, she smiled and congratulated herself on the job she had done feminising him, he was perfect for working as a sissy whore. She returned and led him and three of the biggest sailors into a private room. She stripped them naked and they sat in the chairs and drank with her as they watched Jack dance for them stripping down to just his thong and heels. She watched him stand in front of each of them wiggling his bubble butt in their face before turning and taking their hard cocks in his mouth, sucking them greedily before moving onto the next. She could feel herself getting wet as she watched her slut perform for her. She moved her hand between her legs and began to rub slowly against it, her clit on fire. She played as Jack pulled the black men around him as he went to his knees, sucking and handling the three enormous cocks in his face. One of the young black guys had an amazing bum she thought, moving closer to it.

She knew she wasn't supposed to but she couldn't resist kneeling behind him, parting his cheeks and sticking her tongue in his arse. She reached underneath and cupped his balls while she explored every inch of his puckered hole. His cock was in Jack's mouth, she felt his balls begin to twitch and knowing he was about to cum she thrust her tongue deep inside him. She felt him release and saw him shoot an enormous amount of semen into her husbands face and mouth. His beautiful black behind sat back in a chair spent and she sat with him, watching the other two black men carry Jack over to the bed and place him on all fours. She idly stroked herself with one hand and her black mans cock with the other as she watched her slut get spit roasted with pride...

Jack loved being manhandled, especially by hot black men, they threw him onto the bed and he submitted to them completely, he loved their hands all over him and the feel of their big black body's dominating his weak girlie body. He allowed them to manoeuvre him on to all fours, he spread his legs slightly and tilted his arse upwards, making it clear he wanted to be fucked. He took Josh (first black guy) into his mouth, he tasted delicious and was clearly excited as Jack was treated to some warm and salty precum. Jack looked up into Josh's eyes while he rolled his tongue around the tip of his big black cock. He looked at Josh's broad shoulders and strong arms and felt his nipples harder and his arse begin to dilate.

He wanted to be fucked hard by these beautiful black men. He continued sucking and licking Josh, desperate now for some attention for his empty hole, but was soon relieved as he felt Amos thrust two well lined fingers deep inside him. Jack gasped with pleasure and looked over his shoulder at Amos, he was 6ft tall and stacked, looking his rippling muscles made Jack's fingered hole quiver with excitement. The fingers felt so good, thick and strong, opening him up ready for his reward, long, hard, thick black cock! Amos soon had Jack's hole slippery and wet and slid in fingers three and four. Jack was panting now and he could feel beads of sweat between his cleavage. He wanted to be fucked so bad he was thrusting backwards towards Amos almost involuntary.

He turned and looked at Amos pleading with his eyes. Jack could see Amos knew what he wanted and soon felt the tip of his 10 inch prick at the entrance to his slutty arse, it was as thick as a coke can and the pressure as it began to enter Jack was enormous. He was a professional slut and he knew how to take big cock in fact he lived to take big cock! Relaxing all of his muscles and bearing down on the monster cock Jack opened himself enough for Amos to enter him. With a gentle plopping noise the bulbous head was inside and Jack cried out with pleasure. 'Oh god baby your cock is so big' he moaned. Jack felt the rest of Amos enter him, it was a feeling of intense fullness and Jack was in ecstasy.

'Fuck me baby, fuck your white slut!' He cried. Amos began to thrust harder, opening Jack up even wider, his slutty arse slippery and gapping.

'Yes baby fuck you white white, fuck me baby, fuck me hard!' Jack continued.

His arse was wet and loose now and Amos was pounding him hard, each thrust rubbed against his prostate taking him closer to the anal orgasm he craved. Jack tits were swinging around underneath him, something he was still getting used to. No longer able to continue sucking Josh during the assault on his pussy.

'I want you both to fuck me, double fuck my sissy slut arse!' said Jack.

Josh and Amos looked at each other and grinned. Josh lay down on the bed and Jack straddled him, once Josh had slid his cock into Jack Amos lined up and slowly pushed his cock in. Jack loved the double, he had fucked thousands of men in his job as adult and his arse was quite a gape, he loved the feeling of extreme stretching he could only get from double penetration. The two big black men began to thrust harder and harder, Jack moaned and panted with pleasure, crying out for them to fuck his white pussy, that he was a black cock slut and that he loved being caged and helpless to them. Jack looked down and could see his limp clit was dribbling into his cage a small puddle forming on the bed sheets. He knew Jill would make him lick that up later. Soon his black lovers could take no more and they spurted rope after rope of hot salty cream into his gapping man pussy. He loved how that felt, all sticky and wet. He loved this, he loved doing it for Jill, he loved her watching him...

Jill was watching the performance and it was making her very hot, she could feel the black cock in her hand starting to harden, Jordan was obviously enjoying the show too! Leaning over to the side she slipped his big black tool into her mouth. Never taking her eyes off her sissy, she savoured the delicious thickness as it stretched her mouth. She cupped his balls and took him deep into her throat, sliding up and down the shaft she never took her eyes off her sissy. Her pussy was throbbing with excitement now and she reached down for her clit, rubbing slowly she continued to gorge on Jordan's black meat. She came up for air, still ringing the tip, when he lifted he up and brought her down impaling her on his vast cock, she breathed in hard as her pussy was forced open and filled to the brim.

She was upright and he was taking her from behind so she could still watch the stage. She ground herself down on that big dick and gasped as his hands found her clit. She continued to grind as he continued to rub and both increased the pace. Soon she was frantic, squeezing her nipples wishing she was squeezing Jack's, on a rocket ship to orgasm! She came hard, her juices pouring from her gaping pussy, coating her and covering Jordan's thighs, waves flooded through her body. She sat grinding slowly for a few minutes while she regained her breath, watching Jack take the second black cock into his slutty hole. Mmmmm she thought, her own arse twitching with excitement and she lifted herself up off Jordan's cock, moving it back to enter her anally. The tip stretched her open, making her cry out in pleasure, slowly Jordan filled her entire tunnel, she leaned back on his shoulder, purring with pleasure as he started to pound her slutty arse, she bounced up and down taking every inch of his enormous girth deep inside her gaping fuck hole. She grabbed for her clit, her fingers working overtime. She was close, she could feel his balls clench and she knew he was close. She thrust down on him hard and began to cum.

'Cum in my slutty white arse,' she screamed 'fuck my arse with you big black cock!'

She felt him unload and her arse flood with hot sticky cum. She looked at Jack, her eyes had hardly left him, he smiled and gave her a dirty wink, then he snorted a huge line of cocaine off a black cock...

Jack was still on all fours, snorting cocaine from Amos's huge member. He could feel a river of cum running out of his arse and down his thighs. What a waste he thought licking his lips. Jill had joined him and had a line from Amos's cock. He kissed her and then began licking the residual powder from the cock. Jill joined him and they were soon gobbling Amos back to life. Jack watched Jill's eyes widen as she saw just how thick this monster was.

'Oh my god,' she said 'I'm so jealous you had that inside you!'

'I think you should try it out!' he smiled.

They knelt on either side of Amos taking it in turns to suck him and lick his balls. Amos lay back moaning with pleasure. Jack felt Jordan slide in behind him and watched Josh slide in behind Jill. Almost instantly he felt the tip of Jordan's prick at his entrance, he thrust back gently to tell Jordan to enter him. He felt a little pressure and the Jordan's whole length and girth was inside him. It felt nice, he smiled, Jordan had a lovely cock, he looked forward to comparing notes with Jill later. He continued working Amos's cock with Jill and occasionally their lips would lock and they would look at each other and kiss. He watched her eyes widen and her hold her breath and he knew Josh had entered her pussy.

Soon he was in a rhythm rocking back and forward to Jordan's thrusts and licking up and down Amos's shaft. Jill was lying on Amos's thigh, she had rolled over and Josh was now on top, thrusting his muscular hips, driving his enormous tool into Jills swollen pussy. He looked and was fascinated by the contrast between her soft pink pussy and his huge black dick. It made him very horny! He focused on sucking and getting fucked like a good sissy whore. His clit was dripping through its cage and his prostate was under constant pressure, he began to cum, his sphincter in full spasm milked a huge load out of Jordan, which flooded his already leaking arse. He looked across at Jordan and watched him fill his wife's ruined pussy with a colossal load. She was purring with pleasure clearly having cum several times. Amos still hasn't cum despite Jack's best slut efforts so he pulled Jill over, onto her knees.

'I want you to take Amos's monster in your arse.' he whispered to her.

'Yes please!' she beamed.

Pulling Amos over to her she told him to fuck her white slut arse. Jack watched her on her knees, he poured lube all over her arse and guided Amos to her door. He watched, proud, as Jill's greedy sphincter opened up and took it all. She grunted hard at the first thrust and then started to get comfortable with the rhythm. Jack crawled back under her and started running his tongue all over her clit. He was looking up at Amos huge tool and balls destroying his wife's arsehole. Lucky bitch! he thought smiling. He looked down and could see Jill licking all the dribbles from his cage, she was such a dirty bitch. He sucked his wife's clit hard as he watched the pounding, she was shaking with pleasure he knew she was going to cum soon. Amos let out a loud cry and released his juices deep into Jill's cavity, as he pulled out a huge blob of cum leaked down into Jack's face who ate it greedily. He pulled Jill lower and tongued all of the cum out of her, keeping the pressure on her clit until she gushed into his mouth. He savoured the taste of cum and his wife's pussy on his lips, he could feel his gaping arse leaking and he was in bed with big black men. He was in anal heaven.

It was several hours later when the black men finally left. She lay on the bed with Jack and they kissed and held each other. Finally it was time to go and she began to remove the cage from Jack's cock. She loved how limp it was and had stayed all night, she rubbed the tip and licked his clit dribble from her fingers, he had a nice soft limp clit most of the time now she had trained him well. The oestrogen tablets she had put him on also helped. She grabbed her clothes and headed for the bathroom. She felt Jack next to her as he sat down to pee, she had insisted on this sissy behaviour from the start and she loved watching how he sat on the toilet like girl now, knees together.

They cleaned and dressed each other, applying their makeup. She helped him with his tuck and secured him in a white thong. She could see the white material didn't cover his well fucked arse, she loved it when he gapped, she was always on the look out for extreme toys to fuck him with at home, the bigger the better. Tucked in his thong and bra he looked just like a woman she thought, it turned her on. She straighten their dresses and with one last look in the mirror they left the bar and headed home. She liked their walks home, they both had enormous slutty heels on and it was more of a wiggle than a walk, but they gossiped all the way home about how different cocks felt and tasted, who they had enjoyed fucking the most and what they wanted to do next. She opened the door and kicked off her shoes, Jack did the same and she led him to the bedroom. She leaned in and kissed him hard on the lips, their lipstick smearing, she felt his hands on her removing her dress, she removed his. She grabbed the baby oil from the dresser and poured a generous amount onto Jack's tits, he lifted his head back, his blond hair flowing down his back, she rubbed it in slowly, working it in and concentrating on the nipple. She listens as he groaned in pleasure, she knew he loved his new tits. She watched as he did the same, rubbing her breasts with the slippery oil.

They were soon panting and moaning with pleasure, stood their both in thongs just rubbing each other. She could feel the oil running down into her panties, he slid them off her. His fingers caressed her ruined pussy, gently stimulating her clit. She relaxed enjoying the lightness of his touch. Moaning now she knew she was going to cum, she could feel semen from early in the night leaking out onto his fingers. She came, grinding herself into him and squeezing his nipples hard. She moved down onto her knees and released his clit from his thong. It sprang to life in her face. She took the tip in her mouth and sucked gently and slowly, her fingers finding his ruined pussy. She started by inserting a finger and then two and then four, he was so loose she slid her whole fist in easily. Pumping his cock with her mouth and his greedy hole with her fist he came very quickly, she opened her throat and let his delicious cum enter her. She licked her lips and fell into bed with him. They held each other and fell asleep. She loved having a sissy husband...

He took off his bikini top and rubbed suntan cream all over his big tits, he did this very slowly, spending a long time on each nipple. He loved the feel and sensitivity of his new tits and couldn't resist playing with them. He loved it when Jill played with them, when she sucked his nipples and squeezed them hard, her big strap on cock filling his arse. He smiled and looked over at Jill. She was wearing a matching bikini and looking hot. They often wore matching outfits, it made them feel closer and held them together when they were performing for men at the bar. He sat back on his sun lounger and looked at the pool, it glistened in the sunlight and looked very inviting. They came to the pool most days, it was a nice way to relax before working in the bar. He loved wearing a bikini, he felt so feminine, he was very careful to tuck himself properly so he had a perfectly smooth profile. He loved spreading his legs wide knowing all the men at the pool were looking. They lay there topless, giggling about big black cocks as usual. There were several large black guys on the other side of the pool they kept looking over at him and Jill.

'I think they like us,' she giggled taking a sip of her cocktail.

Jack rolled over onto his front, clearly showing the queen of spades tattoo on his arse, a clear sign to any black guy that he was a black cock slut, Jill had a matching one on her cheek.

He sipped on his cocktail a little drunk now and waited. Soon enough a group of seven or eight of them came over and sat with them. He and Jill flirted outrageously with them all afternoon and the cocktails flowed. The conversation was very dirty and they discussed gang bangs, ladyboys and double anal penetration. Jill told them how much she enjoyed seeing her husband tied up and fucked. This seemed to make them very horny.

'It's getting late why don't we go back to our place and get comfortable?' Jack said.

Soon they were all back at the apartment and in various states of undress. Jack and Jill had gone to change into more suitable lingerie and were now sprawled out on the sofa, touching and being touched by a group of black men. Jack watched Jill take a cock in her mouth and begin to suck greedily. He loved watching her with other men, she was such a black cock slut, just like him. Jack took another cock and licked the tip, taking it slowly into his mouth and down his throat. He loved the taste and feel of a big black cock in his mouth. He felt hands in his panties and the cool kiss of lube sliding over him. He adjusted his position so he could spread his legs wider and allow easier access to his aching pussy.