Jack and Jill Pt. 02: Jean

It was two weeks later when Jean returned, it had been arranged that she would get there a couple of hours before Jill came home, to prepare him. He wasn't sure what to expect and he felt a mixture of excitement and anticipation. He followed her into the bathroom where she stripped him naked and shaved his entire body. He loved the smooth feel of his skin, especially his thighs and balls, it felt naughty and erotic and strangely natural all at the same time.

'That's better' Jean smiled with pride, 'a good sissy keeps her skin smooth and hairless for her mistress.'

He shivered, the feel of the cool air on his bare skin and the thought of having a mistress, a master, someone to control you, for you to be submissive to, it was all very new and he still hadn't come to terms with his true feelings about it, but for now he was willing to explore this new side of his sexuality. He watched as Jean removed five plastic cylinders with bulbous tips and a large bottle of lube.

'On your knees sissy,' she laughed 'it's time to prepare your pussy for your mistress.'

He got down on the bed on all fours, the cool feel of the lube making his tight hole pucker.

'Relax now.' Jean instructed.

He felt the tip of the smallest cylinder press against him before sliding through his sphincter.

'Mmmmm...' he cried out involuntarily.

'You like that don't you, you little slut.' she cooed.

Jean moved the anal stretcher slowly in circles and then in and out of him, making him pant with pleasure. Then it was gone and she was lubing the next size up, he braced himself, but it slid in effortlessly and he couldn't help grinding into it.

'You want more don't you baby?' Jean smiled.

He continued to pant with pleasure, already wondering about the next size up. His greedy hole quickly reached the biggest sized stretcher, he loved the feeling of having it filling him and holding his arse wide open. He couldn't deny he enjoyed being an anal slut.

The mixture of excitement and anticipation returned as Jean removed a cord, with two rubber hoops attached, from her bag. She proceeded to place them around his cock and scrotum and then pulled the cord back hard between his legs. He gasped, his whole manhood firmly tucked behind him. She tied the contraption around his waist securing the arrangement.

'There you go baby girl,' she said ' now you will be all smooth in your panties.'

Jean and Jill had picked out red bra, panties and black stockings for him. Jean helped him into them and he stood up. He slipped into a pair of heels and began to move around the room. The tight tuck and the heels pulled his knees together and gave his walk a very feminine wiggle, he looked in the mirror and marvelled at how smooth his pantie front was. The thong back held his anal stretcher firmly in place, he was ready to meet his mistress...

She was dressed in her black corset and stockings with a big black strap on cock, when she entered the room to see him. She was pleased, she enjoyed his hairless skin and the smooth line of his panties, she ran her hand across his undercarriage and he felt as smooth as a female. He looked like a true sissy in his pretty bra and panties and looked surprisingly good in stockings! It was all making her very hard and very wet. She pushed him down to his knees.

'Suck my cock!' she commanded.

She watched him obey her immediately, good! he was learning his place. She thrust her hips forward driving her big black rubber cock deep into his throat and providing much needed friction from the harness on to her clit. She fucked his mouth relentlessly until she came, he taking it all like her obedient slut. It was time he submitted to her, she was becoming more and more powerful in her job and she needed that to be reflected in her sex life. She wanted to be in control, in charge, she wanted to be the penetrator, the alpha male, which meant he would need to be her sissy bitch. She pushed him roughly onto all fours and began to play with his plug, rotating and stretching him with it, applying fresh lube before burying her big black strap on deep in his bowels. She felt him resist, she felt him freeze and then she felt him submit, she fucked him hard to show him how powerful she was and to remind him that she was his master.

Every thrust was hard and ranged from tip to balls, she fucked him so hard she could see his strapped up clit was dripping as her rough intrusion milked his prostate and kept him on the edge of full blown orgasm. She could tell he was enjoying all of these sensations as he was grinding and thrusting back at her. He was a complete anal slut. Her complete anal slut. She was lost in the moment, destroying his pussy, when she felt the tip of a big cock part her sopping slit, Jean was behind her. It took a couple of minutes to coordinate, but soon Jean was thrusting through Jill and straight up Jack's arse. He was grunting and panting and grinding, his anus full in a way he had never experienced and the joy of full penetration kept washing over him, Jill was thrusting into Jack in time with the big black cock thrusting into her tight little pussy, her clit trapped against the harness, sending sparks through her abdomen, driving her towards orgasm, she sped up, he started to cum anally and Jean began to shoot hot ribbons of spunk up Jill's vagina, Jill unable to take anymore screamed out as her orgasm ripped her apart leaving her shaking and soaked, with a pussy dripping hot black semen...

He lay there catching his breath, his panties pulled to the side, his slutty hole gapping and oozing lube. He couldn't believe how much he had enjoyed being fucked, having a big rubber cock banging away in his arse, he loved it, he wanted more and wondered what a real cock would feel like, what it would feel like for a big thick cock to cum in his arse. The thought of cum moved him to action, he pushed Jill's strap on forward and went to work cleaning Jeans cum from her wet snatch. It tasted good, he cleaned every last drop before moving out of the way, allowing Jean to get on all fours for Jill. He watched as Jill applied lube to Jeans clearly experienced man pussy, opening her up quickly and easily before sliding her big black strap on cock deep into Jeans hungry cavern.

'Fuck me baby,' Jean whimpered 'fuck me hard!'

He watched as Jill began to thrust harder and deeper into Jean, Jean responding by thrusting back against Jill's intrusion. He was surprised to see Jeans cock seemed much smaller, completely soft, flapping around uselessly, Jeans clitty. The thought turned him on, he wanted his cock to flap around uselessly, for Jill to call it his little clit and humiliate him, feminise him, it was exciting. He rubbed his tucked cock between his legs, he was touching himself like a woman he thought. Every so often precum would leak from Jean as the big rubber cock milked her. He wanted to lick it up off the sheets, he couldn't bear to waste it. He moved under Jean, positioning himself so her cock was in his mouth. He licked the tip, tasting the warm saltiness, ready to catch any more of the precious fluid. Soft at first, Jean began to harden in his mouth, he opened wide, allowing her to thrust deep into his throat. Jean was obviously excited by this as she started to fuck his throat harder and he could see Jill thrusting with all her strength, burying herself in Jeans arse as Jean buried herself in his throat. He focused on not gagging, loving the submission, priding himself on his cock sucking ability. It wasn't long before Jean dumped a huge load of semen into his throat, cumming with her cock and anally at the same time she screamed the place down. He lay there, feeling the warm liquid coating his mouth and sliding down his throat. He loved cum...

She watched her sissy husband swallowing cum and smiled, his training was going well, it was time to humiliate him a bit further with some arse to mouth action.

'Come here my cum guzzling slut.' she ordered, standing up.

She pushed him down so he was kneeling on the floor in front of her.

'My cock is all dirty after being in two greedy little arseholes tonight, I want you to clean it.'

She watched him look at up at her, total submission in his eyes and she knew she had been right about him all along. He was a little bitch, he always wanted to be a girl and now he was loving the chance to be one. She thrust her cock forward into his open mouth and watched him lick and suck her big black rubber cock completely clean, he took every inch of it into his mouth and sucked off every drop of musky lube. She looked at him with a mixture of surprise and pride, the dirty bitch was actually enjoying cleaning her dirty cock.

'Get up on the bed on all fours.' she ordered.

Obediently he did has he was told with hesitation or question.

'You are such a dirty little slut,' she scolded 'I think you should be punished.'

She spanked him hard across his arse leaving a red welt. She watched, he just took it, she spanked him again, harder this time. She watched, again he just took it. She went over to the bedside drawer and removed a riding crop. She whipped it across his arse, his breathing increased its pace, but he didn't cry out or complain. She unstrapped his cock and let it dangle pathetically between his legs. She looked at his floppy useless clit and gave it a quick swipe with her crop. He inhaled hard, and withdrew, but quickly returned to his original position, arse high in the air for her to abuse.

'You are a dirty little slut aren't you?' she said.

'Yes mistress.' he replied.

'You are a cum guzzling whore aren't you?' she said.

'Yes mistress.' he replied.

'You love having a big cock in your arse don't you?'

Yes, yes mistress.' he cried, instinctively thrusting his arse back towards her.

'Well,' she said 'you are going to feel what a real, big, thick, black, cock feels like in your arse. Would you like that?'

'God yes, I would, I would.' he cried.

'Good slut.' she replied.

She took the ball gag from the drawer and pulled it around his head, strapping it firmly from behind. She pulled his arms up behind his back and tied his hands together with a cable tie. Trussed up like a chicken, she looked at him, helpless, greedy gapping anus up in the air and his face buried in the pillow. It was her job to humiliate him and force him to submit to her will...

The tip of Jeans cock stretched his sphincter to the limit before passing through with a feeling of relief and satisfaction. He felt her helmet run up the inside of his anal passage and rub his prostate. He looked down between his legs at his limp clit, it made him feel more girlie to see it flopping uselessly around and he could see it dripping precum as Jeans big prick began to milk him. He bore down on her, his hole opening wider to allow more access. He felt her big black cock reach his limit and her balls slap against him. He felt full. He loved it, the fullness and the throbbing heat from a real cock made him feel like a real woman. He wasn't gay, he was a girl. He had for a long time wondered what it was like to be the girl when he watched porn. He was fascinated by penetration, how good it would feel and the submission required to allow a big cock to dominate you.

Now he knew and it was blissful. His arse was full and Jean kept ramming her cock deeper and deeper into him. He let go, submitting completely, allowing her to fuck him as hard as she wanted. Being a willing anal slut for her. The pressure on his prostate was immense, the feeling overwhelming, he watched his clit leaking precum onto the sheets. He pushed back, taking more and more cock into his bowels, loving every second, wanting more and more, his arse hanging loosely open now, slutty, greedy and always hungry. The friction from Joan's rampant tool bringing him all the way to climax, he came, hard, his whole body now centred on his ruined anus. His clit slowly milked, he cried out in ecstasy, Jean carried on relentlessly fucking him, her big throbbing cock widening his fuck tunnel with every thrust. He knew he would never be the same after this, his arse would never return to normal, his man pussy would be like Jeans, easy to open up and penetrate any time Jill wanted to have him, the thought turned him on even more, he began to thrust back even harder, his clit flapping against his stomach and thighs in the furious movement of his pelvis. He was Jill's bitch, he was Jeans bitch, he was a sissy fuck toy. He knew his place.

Jean continued to rut him until finally she came, deep inside him, emptying the remains of her balls into his eager crevice. Leaving him lying on his front. Gapping obscenely, cum leaking from his destroyed opening. Stockings and bra still intact, but no panties, like the victim of a sex crime, except he was satisfied and happy to be a sissy bitch. Loving his anal adventures and proud to be a cum guzzling whore. He loved cock, he knew it now. Big rubber cock or real cock made no difference as long as he was being penetrated hard, for her, Jill, his mistress, always for her...