Jack and Jill Pt. 04: Jean

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The trio take a trip to Thailand.
4k words
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Part 4 of the 6 part series

Updated 06/09/2023
Created 06/17/2020
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He looked in the mirror, clean shaven with blonde wig and full make up, he was unrecognisable to himself, his false eyelashes fluttered back at him, his shoulders, his hands and his Adam's apple all gave him away on close inspection, but from a distance he was passable as a woman. He couldn't believe he was doing this, he was terrified of going out in public like this, but they were in Bangkok and it was all very surreal.

'You will be fine baby.' Jill comforted him.

'Just think of all the cock out there for a dirty bitch like you to suck!' Jean smiled.

He adjusted his tuck one final time, zipped up his black thigh high boots and pulled down the bottom of his white mini dress, which was covering nothing and the three of them left the hotel heading for Patpong and the sex district...

She was already wet with excitement when the taxi delivered them to their destination, making her sissy go out in public in his sluttiest outfit pleased her immensely and thinking about the possibilities, the adventures they were going to have made her tingle. The street smelled of food and sweat and copulation, bars lined either side, semi naked local women dancing and flirting outside, desperate to pull in the passing sex tourists. Her heart beat increased, she grabbed Jack's hand, who grabbed Jeans hand and they entered the first bar, the Queens Castle. The bar was dark and seedy, the centre of the room was dominated by a large stage where naked girls were performing various tricks with their vaginas for the crowd.

She stopped dumbstruck for a second, Jack and Jean at her side as she watched a girl on stage pull a string of razor blades from her pussy while another emptied, held and then discharged a large, full bottle of Coca Cola from her pussy. This place is crazy she thought, moving to the bar and taking a seat, the girls with her, she ordered cocktails for the three of them, she soon finding herself surrounded by young scantily dressed Thai women. She enjoyed their attention, their hands on her body, their soft breasts pressing against her, her hands on their bodies. Soon fingers were between her legs, working their way into her wet folds, she spread her legs on the bar stool, throwing back her head and grinding against them.

Fingers inside her now quickly and expertly found her G Spot, she looked down at the pretty Thai girl with big breasts who was working her pussy and smiled. She saw the girl return the smile and then move closer, finger fucking her harder. Jill leaned back, her pussy gushing all over the stool, the floor and the Thai girls hand and came hard, pulling the Thai girl in close to her and holding the Thai girl tight as she shuddered through her orgasm. When she was done she released the girl and sat catching her breath. The pretty Thai girl looked at her expectantly and Jill gave her 50baht, the girl seemed pleased, but not as pleased as Jill who's pussy was still quivering with delight. She slid down her sopping panties and put then in her bag, the fresh air on her pussy felt good and she felt extra dirty knowing every man in the bar could see her bare and very moist vagina as she sat there in her obscenely short dress...

He sat on the barstool in his his tiny dress and slutty boys watching his wife being pleasured by pretty a Thai girl, he squirmed in his seat imagining his pussy being fingered, the pressure on his tuck felt good. He watched his wife climax, giving her own little show to every man in the bar, followed by a display of her wet pussy. As men began to approach the three of them, Jill grabbed his hand and led him and Jean off to the bathrooms.

'You need some lipstick baby' she said to him.

'That was quite a show!' Jean laughed to Jill as he applied more red lipstick.

'I needed that,' said Jill 'seeing my sissy out on the town dressed like a slut made me so horny, I needed relief, besides I enjoyed being part of the show, did you see all those guys looking over at us?'

'They want to get their hands on your greedy little pussy!' Jean teased, grabbing his arse.

Make up applied, he looked around at the squalid bathroom, it was small and dirty with a large curtain at the back. He tottered over to the curtain on his heels, his tuck pulling his knees together, making his arse wiggle in his tight dress, he pulled the curtain open and looked behind, he smiled and licked his lips as he realised the room connected the ladies and men's toilets and four glory holes were in the wall opposite. A big black cock was poking through one of the holes, he felt sure it belonged to the big American he had been eying up at the bar. He quickly got down on his knees and took the head into his mouth. He felt the cock pull back and then thrust into his mouth.

He allowed the cock to fuck his mouth and throat, sucking it eagerly, licking the shaft and wishing he could lick the balls. He looked to the side and tried to smile through a mouth full of cock as he saw Jill and Jean, also on their knees, sucking hard on strange dick. They were clearly savouring every second. He returned to his black monster and pumping the shaft with his hand, sucking and swirling his tongue over the tip he brought it to conclusion. Thick ropes of hot semen spraying into his mouth and all over his face. He swallowed greedily enjoying the salty goodness sliding down his throat. He looked over at Jill and Jean and watched as they took their own facials, he smiled again at what a trio of dirty bitches they were. He stood slowly in his tight dress and high boots and tottered back to the sink to fix his makeup...

She left the toilets with her girls in tow and headed for the bar, she sat and drank cocktails, chatting and giggling with her cross dressing entourage. The conversation rarely strayed from their favourite subject, cock!

'Who's going in the chair?' said Jean mischievously, looking over at the bukake chair next to the stage.

She couldn't explain where her sudden surge of confidence came from, but before she knew what was happening, she had pulled her dress up over her head and was strutting through the bar wearing just her bra, stockings and thigh highs. She wiggled her way over to the bukake chair, every eye in the room on her. She sat in the chair, her legs up in the stirrups, her moist pussy facing the crowd, she lay back, closed her eyes and moved her hand between her legs, rubbing slowly, she started to explore her sensitive clit. She floated away in her own world, revelling in the extreme sluttishness of playing with herself for the enjoyment of a room full of men. She strummed contentedly, moving her hips in time with her hand, bringing herself very slowly towards climax. Gradually she became aware of movement around her, she opened her eyes and saw a growing crowd of men standing around her, cock in hand, masturbating in unison with her. This excited her very much and she began to rub harder, sliding her fingers between her lips and inside her soaking hole, using both hands now she started to moan.

'Mmmmmmmmmm, ohhhhhhhhhhhh, yesssss!' she panted playing up for the crowd.

She felt the first lot of hot fluid land on her stomach and watched it pool their, this was quickly followed by another and another. She loved the feeling of hot cum on her body and urged the crowd on.

'Yes, cum on me, cum all over me!' she purred.

This was enough to push many of them over the edge and she soon found her body entirely covered in spunk, the taller men shooting ropes of salty relish all over her face. She scooped handfuls of the warm semen tipping them into her mouth, enjoying the taste she craved. She began to rub herself with fresh vigour, until she couldn't take any more, her body thrashing in the chair as her orgasm ripped through her body, radiating from her swollen engorged clit, outward until it touched her everywhere. She felt light headed and weak and in that moment she felt like she was outside of her body, watching herself lying in the chair, her face and body covered in cum, her pussy drenched in a mixture of cum and her own juices, her lace bra now cum soaked, her thigh high boots splattered with cum.

She was a real cum dumpster and she loved it, she loved losing all her inhibitions and allowing her inner slut to run wild. She came to a few seconds later and began to rub herself again, watching all of the hard cocks surrounding her shoot their load, this drove her crazy with lust, she could feel the cum on her hands and fingers getting rubbed into her greedy cunt and she loved it. It didn't take very long for her to cum a second and a third time. Finally the crowd dispersed and she was left there spent and covered from head to toe in strangers spunk. She opened her eyes to see Jack and Jean laughing and clapping. Helping her out of the chair, they gave her a towel and led her towards the bathroom...

He was helping Jill to the bathroom with Jean when a strong black arm grabbed him and manhandled him into the men's bathroom. The two girls continued into their bathroom, not realising what was happening. He tottered on his heels, trying to keep his balance as the large black man pushed him into the nearest stall.

'Wha...' he began to speak but was cut off.

'You've sucked my cock like a bitch, don't you want me to fuck you like a bitch?' Asked the deep voice of his assailant.

He thought about objecting, but the truth was ever since he had sucked it, all he could think about was having that lovely big black cock inside him. He opened his purse, pulled out a bottle of lube and poured it all over the big black mans cock, which was raging hard and exposed, the black mans trousers now around his ankles. He took off his dress and stood there in his well padded bra, panties, stockings and boots. He turned around, pulling his thong to the side, exposing his hole, but protecting his tuck. He bent over the toilet and submitted to the big black man behind him. He felt the head pushing against his back door forcing him open, it was tight, but his well used slutty hole opened up quickly allowing 10" of thick black meat to fill his greedy tunnel.

'Ughhhh...' he grunted as the black cock thrust into him, touching the furthest regions of his gurl pussy.

He loved the feeling of being opened up and stretched, especially by a delicious big black dick, he pushed back against the monster penetrating him, all the way until he could feel big black balls pressing into him, he wiggled his hips, enjoying the fullness and the feeling of being dominated. He panted harder as he felt the thrusting start to pick up pace, each deeper than the last, the head rubbing against his prostate, milking him and pushing him towards climax. He felt his clit dripping into his panties creating a wet spot.

'Oh god yes!' he cried out involuntarily.

'You like that don't you bitch?' his black man laughed.

'Yes, yes I do, fuck me, fuck me, fuuuuuck me!' He replied breathless.

He spread his legs wider, wanting to take every millimetre of that beautiful cock inside his slutty gape. He felt the weight of the black man on his back as the relentless thrusting continued, then a big black hand between his legs, rubbing his tuck. He loved it, he felt so feminine having his smooth undercarriage fondled while he was being fucked hard. It wasn't long before neither of them could take it any longer, his anal orgasm hit hard, like tidal wave washing over him. His anal passage clenched hard milking a massive load of cum from the huge tool in his arse. His spasms continued for some time and the cock remained blissfully buried inside him, his bowels completely coated in semen. Slowly the diminishing cock withdrew, leaving him with a sense of loss. Cum leaking from his gaping pussy he turned to face his big black man, eyelashes fluttering and lips pouting as he had been taught. Strong hands pushed him down until he was sitting on the toilet, slightly confused he looked up, but his big black man turned around, pushing his big black arse towards him until he understood. Parting the black cheeks with his hands he buried his tongue deep in the black anus in front of him.

'Ughhhhhhhh...' his black man grunted, clearly enjoying the attention at his backdoor.

He licked hard, pushing his tongue deep into the musky hole in front of him. He loved it, licking out that big black arse really turned him on. He reached around and began stroking the cock and balls as he sucked and licked and thoroughly tasted every corner of the black sphincter. The cock in his hand quickly regained its hardness and he began to pump in time with his tongue.

'Oh god!' his big black man grunted and he knew he was on the edge.

He could feel the balls in his hand contract as he licked arse and pumped shaft. At the last second his big black man turned to face him, shooting cum all over his lace bra and panties. He sat there on the toilet frozen as his big black man pulled up his trousers, threw 50baht at him, turned and left. Suddenly he was alone in the stall, his underwear soaked in semen, cum dribbling from his arse. He felt dirty, used and abused, he had been treated like a whore! It was very slutty and he loved it. He wiped himself with tissue, unable to resist tasting some of the cum, put on his dress and headed off to find the girls...

She and Jean met him leaving the bathrooms, she saw the cum leaking down his thighs and smiled, dragging him and Jean back to the bar to get the details. She drank cocktails and listened to his story of the black man in the bathroom, she was getting hot now, she needed to cum again, she needed to fuck him and she needed to be filled herself. She needed somewhere for the three of them to go, she spoke to the barman who escorted them to a private room out back. The room had some chairs and a large bed, the walls were plush with blood red curtains, it was a very sexy room. She removed her dress revealing her cum stained bra, standing there in her stockings and boots her pussy wet.

She watched Jean remove her dress and her panties, her big black cock flopping between her legs. Jack removed his dress, she smiled, his bra was as cum stained as hers. She watched him remove his panties and release his tuck, his clit dangling limply between his legs, his arse still leaking semen. She pulled the two of them over to the bed with her and kissed Jack hard on the mouth, Jean moving behind to finger his gapping arse, Jack's hand on Jeans hard cock, the three of them tangled up in each other. She broke away to retrieve her strap on from her bag and Jean thrust her cock in Jack's mouth, his lipstick staining the thick black shaft. She moved in behind him, lubing her big rubber dick, pushing it firmly through his barrier and filling him in a single thrust.

'Mmmmmmmm...' he gasped.

She began to thrust, the pressure on her clit driving her on, thrusting harder and deeper into him. Jean came quickly and hard in Jack's mouth, withdrawing her softening prick and moving to the other end of the bed. Jill picked up the pace, watching his limp little clit drooling and dripping between his legs as she fucked his prostate dry. She pushed his face down into the pillow, pulling his arms up behind his back, taking control. The pressure on her pussy building and building until she came, burying herself completely in his bowels, forcing his anal orgasm to explode through him. He collapsed to the bed gasping for breath and was quickly replaced by Jean, her pre lubed arse, clearly desperate for attention. She spread Jeans cheeks and pushed the head of her cock into Jeans waiting backdoor.

'Oh baby, fuck me baby!' Jean cried out to her.

She began to thrust, pleasuring her clit again and again, fucking Jean with all her strength until the two of them collapsed in post coital bliss. Lying there with her girls, she enjoyed a moment of quiet satisfaction at the naughtiness of their sex life. She was brought back from her thoughts as she felt lube being applied to her arse, she moved her legs to allow better access to the fingers working their way inside her. She wiggled and gyrated allowing the fingers to stretch her open. She could feel Jack's breath on her shoulder and his bra pressing against her back, she turned her neck to kiss him as he slid his cock slowly into her puckered bud. She relaxed and pushed back taking his whole cock in her anal passage.

He held her close and became still, allowing her to get used to the fullness inside her bowels. She moved against him, slowly riding his big cock, he began thrusting and she started to moan with pleasure. She felt Jean move closer and she rolled over on to Jack allowing Jean full access to her desperately hungry pussy. Jean moved in, her cock sliding into Jill's pussy all the way to the hilt. She was breathless with pleasure as the two big cocks pounded her relentlessly, making her cum from every hole in every way possible, she was screaming the room down and she was sure that Jack and Jean were close to cumming inside her when the curtains began to open and a whole bar full of men were sat watching them. She gasped in surprise and the three of them froze...

Once the shock of being the main event on stage had subsided, he continued to thrust cumming quickly into Jill's musky tunnel, he could feel Jean's cock spewing semen into his wife's pussy through the thin membrane that separated them. He withdrew and lay panting beside the two of them, trying to regain his breath and his composure. When he looked up again he saw Jill talking to the bar manager at the side of the stage. He looked over at Jean who rolled her eyes and smiled. Jill returned, wearing only her cum stained bra, stockings and boots, with a spreader bar in her hand, he allowed he to position him on his knees, strapping his legs wide open to the bar and pulling his arms though, between his legs, securing them to the centre of the bar. He knew she had plans for his arse and he submitted willingly, he loved being her sissy bitch and would do anything to please her. He felt her lube him up, her fingers working inside him, he was already stretched from the dildo and he gaped open quickly.

His face was forced down into the bed, but he was still aware that the men from the audience were now on the stage with them. Jill withdrew and he could hear her arranging a line behind him, a queue to fuck his wet pussy. He felt the first cock press into him, it entered easily and he began to press back against it, taking all of it inside him, he felt his penetrator start to pick up speed, ramming his cock up inside him, stimulating his prostate and milking his little clit which was drooling between his legs, flopping uselessly around. The sight of it turning him on and encouraging him to push back even harder and faster. He soon felt the cock inside him give up its load and fill his cavity with warm salty fluid, it withdrew and was quickly replaced with another, this one much thicker, he relaxed, trying to help its girth pass through his sphincter, it felt good, he loved being stretched, he pushed back, forcing the large head up into his deepest regions.

'Oh, yes!' he gasped, the pain and pleasure of this monster tearing him in two, pushing him towards orgasm, the internal pressure milking him hard, a steady stream dripping from his clit.

He took his pounding, savouring every second, feeling his fuck tunnel stretching wide open until he was comfortable, even greedy, for more girth. He felt the huge balls smashing into him, dominating his girly little balls, until they contracted hard and dumped a huge load into his ruined anus. He felt more and more of the juices running down his legs, onto his stockings, with every finishing thrust of the big dick inside him. His head was lifted from the sheets and he looked up and saw Jill, legs splayed, positioning him onto her wet slit, he began to lick and she began to purrrr, arching her back and throwing her head back, they were surrounded by men, cock in hand, stroking themselves to the show they were putting on. Hands grabbing at her tits squeezing her nipples, she turned to the side taking a strangers cock in her mouth, he focused on her clit, he knew she would be loving all of those hands on her body. A large glob of spunk landed on her pubic bone and he gobbled it up quickly, then returned to her greedy pussy, forcing her to gush hard in his mouth.

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