Transvixen Tranny Rock Band Ch. 04

Tony slowly lowered Cherri onto his stiff rampant cock until his glans nestled against her sphincter. He moved his hands onto her shoulders and pushed her down thrusting up with his groin at the same time.

Cherri screamed as Tony's inadequately lubricated cock forced its way past the tight bud of her sphincter. It was the most intense pain she had ever felt. She had not told Panti, but Cherri had pushed dildos and vibrators inside herself before but they were always well lubricated. Tony's cock felt like a red hot poker as it split her back passage.

Cherri bucked and tried to force the invading member from her rear entrance but Tony held her shoulders in a vice-like grip and pushed her down onto his lap.

"Stop struggling girly!" he hissed, "You know the deal!"

Cherri forced herself to relax and put her hands out and rested them on Tony's shoulders so that she had more control of her lower body. She wriggled her backside until Tony's cock was not causing quite as much pain and then she forced herself to slacken her sphincter muscles and slowly lowered herself. Tears of pain streamed down her face but she persevered and instead of fighting against Tony she used her own strength to control the rate at which his invading member entered her.

After a few minutes of suppressed agony and silent screams she was fully impaled on Tony's shaft; her soft buttocks resting in his groin. Tony sighed as Cherri held herself still as she relaxed her internal muscles and allowed her anus to accommodate Tony's swollen penis. Another beat passed and she was past the worst of the pain. She felt stuffed and invaded but the pain began to recede until it became a feeling of general uncomfortableness.

"Oh yeah baby; that's nice and tight," Tony sighed.

He pushed up with his groin and wriggled his hips swivelling his member around inside Cherri, loosening the tight grip of her anal muscles on his erection. Pre-seminal fluid was leaking the eye of his cock as he became more aroused and further lubricated his shaft and he began to slowly thrust his cock in and out of Cherri's anus. Cherri held on to Tony's shoulders and controlled the tempo as he began to fuck her.

The long slow strokes and the steady stream of pre-come was lubricating Cherri's back passage and helped her to relax her internal muscles. Cherri got into the rhythm with Tony and now that the pain had gone she concentrated on getting this ravishment over with as soon as possible and with the least possible pain.

Theo opened his flies and freed his own erection and gently stroked it as he stared with voyeuristic pleasure as Tony fucked Cherri. The sight before him was highly titillating and the anticipation of participating in the sex was getting him extremely aroused.

Cherri was now quite comfortable sitting astride Tony while he slowly fucked her; the pain had subsided and although she still felt shamed and humiliated, in the dark recesses of her mind she realised that a scintilla of pleasure was starting to course through her body. She had adjusted herself so that Tony's glans massaged her postrate as he thrust slowly in and out. Reflexively she was matching the pace of his thrusts and adjusted her position in his lap to take advantage of the stimulation.

Cherri opened her eyes and saw that Tony was leaning back on the couch; he no longer needed to physically force Cherri to participate in the fucking, so he had moved his hands to her thighs, stroking her stocking tops as she slowly humped up and down in his lap.

Theo stood and made his way over the couch and knelt on the over stuffed armrest. He proffered his erect penis at Cherri. Tony turned Cherri's head towards Theo's groin and she took his phallus in her mouth.

Now it was a matter of getting this over with as soon as possible. She trilled her tongue under the sensitive base of the Theo's glans and she could feel his cock throb in her mouth every time she did. Theo placed his hand on Cherri's head and eased her face back and forth in time with his thrusts. Theo's short stubby cock was actually easy for Cherri to accommodate and she had no trouble breathing while she accepted his organ in her mouth and further stimulated it with her tongue.

Cherri was now fully engrossed in the sex and had to concentrate in order to coordinate pleasuring the two cocks simultaneously. She sucked on Theo's cock and licked and slavered at his glans whilst maintaining a steady rhythm in concert with Tony's fucking. Her anus had dilated enough so that she was able to lift her bottom up from Tony's lap so that just his glans remained trapped by her sphincter and then she pushed down until the hilt of his shaft was buried deep inside her anus. The friction of his glans on her prostate and his shaft on her sphincter was now sending waves of pleasure through her body. She could no longer pretend to herself that she was not taking pleasure from the sex. She was still fearful and felt degraded but she couldn't control the involuntary actions of her body as her excitement mounted.

Tony began to quicken the pace and Cherri matched him thrust for thrust. His crotch made loud slapping sounds as he slammed against her thighs and buttocks, Cherri fucked him back, timing her thrusts to meet his; Theo's cock increased its tempo, sliding in and out of her painted mouth faster and faster as she sucked and slavered his erect member.

"Oh fuck I'm coming!" Tony groaned.

"Oh fuck I'm right there with you boss!" Theo moaned in reply.

Cherri felt her back passage flood as Tony jammed his cock deep inside her and pushed her down forcefully in his lap, squeezing her thighs painfully. He pushed up as stream after stream of his hot semen ejaculated inside her. Cherri could feel the viscous fluid filling her as Tony's cock convulsed inside her. She was ashamed to admit to herself that she was secretly enjoying the fact that she had bought her first man to orgasm inside her.

"Take it you bitch! Take it!" Tony screamed as the last of his seed emptied into Cherri.

Cherri ground her buttocks down into Tony's crotch, her anal muscles milking him of the last of his emission. Warm semen flooded her back passage and Tony's glans pressed against her prostrate in the final throes of ejaculation.

Cherri felt her own penis becoming erect as Theo began to come in her mouth. Cherri suckled his erect penis and coaxed out his orgasm and her mouth filled with creamy viscous semen.

Theo pulled his cock from her mouth as the last jets of ejaculate spurted from him and splashed Cherri's face with semen. She gasped in surprise and degradation as Theo's seed sprayed into her hair and splattered her face. Her eyes stung as the warm secretions mixed with her mascara and ran down her face. A few final spatters splashed on to her blouse and she felt it soaking through the satin material of her blouse onto her skin.

"Get off me you bitch! I don't want no come covered tranny on top of me!" Tony said, struggling to push Cherri off his lap.

Chris had been sitting there masturbating watching the beautiful young tranny being used and now he wanted to get in on the action. He was very strong and he pulled Cherri to her feet, spun her around and tossed her back on the couch so that she ended up kneeling on the couch facing the wall.

Chris stepped in close behind Cherri and grabbed her ankles and spread her legs; Cherri's soft white buttocks were fully exposed to him because her skirt was still rucked around her waist. A rivulet of Tony's semen drizzled from her sphincter.

"At least she's lubed up," Chris laughed.

Chris stood between Cherri's spread ankles and put his hands on her hips and pulled her back hard against him. He pushed forward with his hips and she felt his member nestle in her lubricated anal bud. He grunted and pushed forward with all his bodyweight and his shaft slid slowly and steadily inside Cherri's tight back passage. His crotch slammed hard against her soft creamy buttocks and he ground his crotch in a circular motion against Cherri's lovely soft derriere.

Cherri screamed as Chris's cock forced its way inside her but there was no real pain. She was well lubricated and still dilated from the fucking she had received only minutes earlier. Chris's member slid slowly but inevitably deeper and deeper inside her until she felt him pull her soft buttocks back hard against him; he gyrated his hips as he worked his turgid member around inside her back passage.

"Oh yeah baby I'm coming!!!!" Chris moaned as his orgasm coursed through his body.

Then Cherri felt the hot gush of semen deep inside her for the second in only minutes, as Chris emptied himself deep inside her.

Chris howled and shuddered as his orgasm peaked; he ground his hips harder against Cherri's buttocks. Cherri was still semi-erect from her last fucking and as Chris's glans pulsated and throbbed against her sensitive prostrate, splashing it with his hot seed, exquisite sexual pleasure pulse through her lower regions and her penis stiffened and ejaculated; her own semen dribbled down on to the couch. She couldn't suppress the pleasure she was feeling even though she felt utterly debased.

Chris pushed Cherri forward and pulled away from her and his cock exited her anus with an audible plop. The three thugs watched as trickles of semen seeped out of Cherri's sphincter and ran down her thighs, soaking into her stocking tops.

"I always come quick when I do 'em doggy style," Chris sniggered and spanked Cherri on the buttocks.

"Thanks for the fuck honey!" Tony quipped and slapped her on the bottom.

"Here, you clean up and you two fuck off and get to work," Tony tossed a box of Kleenex on the couch.

Cherri remained facing the wall while she dabbed at her blouse and wiped her bottom. She wiped her face and bunched up the Kleenex in a ball and dropped them on the couch while she adjusted her clothing. Her new red lacy panties were in tatters and she rummaged in the large carry back and found the black panties she had worn to Debenhams and slipped into them.

She realised how awkward this was for everyone as they adjusted their clothing but she heard Chris and Theo leave and turned her head and saw she was alone with Tony.

"You're a good kid you know," he patted her gently on the bottom.

"There's a little bathroom through that door. Go use it to fix up your face and whatever," Tony pointed to a door at the back of his office.

Cherri emerged ten minutes later, her makeup fixed, her hair brushed and her clothing arranged. She'd wiped away as much as the semen as she could off her blouse and it was hardly noticeable on the cream fabric.

Tony had poured a couple of drinks and he was smoking a cigar. He pointed to a chair across from him and he pushed the tumbler of scotch towards Cherri. He lit her cigarette.

"I meant what I said. You are a good kid. Not many would put up with what you did to save their friends livelihood," Tony raised his glass to her.

"Look I know I'm a fat old man but I really like you babe. I'm not going to stalk or harass you but if you should ever fancy spending some time with a rich old gangster...well you know," Tony was actually blushing.

"You got the contract and its binding this time. No more fucking around it's a good deal for all of us; good business. I saw the figures this morning."

"And I promise, I really do, that I won't tell Wendy what happened today. On my heart," he made the sign of the cross.

"Thank you Tony. I'd prefer no one knew," Cherri smiled at him.

"Ok gorgeous. Fuck off I got work to do and you're a distraction," he smiled at her.

Tony led Cherri to the door and bent and kissed her softly.

"I meant what I said about spending some time with me. Dinner, champagne, a show?" he grinned at her.

He politely put his arm around her shoulder as he led her to the ante room and kissed her on the cheek.

"Lucy! Get this young lady a copy of the contract you faxed to Wendy," he bellowed.

Tony turned about and went back to his office and closed the door.

Lucy begrudgingly handed Cherri a copy of the contract.

"What did that cost you?" Lucy looked at Cherri with disdain.

"I'll tell you what. Why don't you join me for lunch in the café across the road and I'll tell you," Cherri smiled at Lucy.

"I don't get off for another forty minutes," Lucy lamented.

"That's ok you can meet me there," Cherri smiled.

"Try not to suck too many cocks when you come through the car park," she said bitingly and swaggered out of the office.

To be continued...