New Pleasures

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"Don't worry," he tried to assure her, "I'm a little nervous about all this too."

Chloe smiled back more confidently and Simon noticed happily that she didn't put up any objection to his hand on her knee.

"Thanks," she replied in a sensual, throaty voice, "It'll be good to have you being there."

Simon was surprised that Chloe rested her hand, painted in a similar way to his, on his and kept it there. When Jessie came back in with a glass of wine each Simon and Chloe were already seated much closer together, with Simon's stockinged legs pressed against Chloe's bare ones. The closeness of this contact made Simon's cock begin to twitch again but Chloe didn't seem to notice as she began to sip her wine in a demure and ladylike way, trying not to smudge her lipstick. Simon tried to copy her in a similar style. Feeling a little light headed from the wine, Simon felt a little more confident around Chloe and moved a little closer, moving his hand up her smooth, soft thigh.

Jessie noticed this and said to Chloe, "Why don't you kiss her? You can see how bad she wants it."

On hearing Jessie's encouragement, and feeling the wine going to his head, Karl looked across at the other girl, Sally. She was a sexy, buxom, little blonde and Jessie was right, she had been coming on to him, her hand rested gently and arousingly on his shaved smooth thigh, worryingly close to his panty clad cock. Placing his hand on her bare shoulder, Karl leant over and placed a kiss on Sally's lips. It was a wet, lipstick filled kiss and Karl felt Sally open his lips with her tongue and began to explore the inside of his mouth as her left hand continued to feel his thigh while the right lingered over his false breast. Karl could feel his arousal growing and, for once, was glad that his cock was too small to betray him.

As they broke from the kiss, Karl saw Jessie was now standing over them, "Why don't we go upstairs?" she said and winked. Taking Karl by one hand and Sally by the other she lead them up to a large master bedroom with a kingsize double bed and a wall with an enormous wardrobe whose doors were mirrors. By now Karl was beginning to forget all his fantasies about Jessie as he began to see her as more of a go between. What he desperately wanted now was to be involved in a girl on girl relationship with the little blonde Sally.

On entering the bedroom Simon only had one thing on his mind, and it wasn't Jessie, there was something about the tall, mysterious brunette that was really turning him on. Grabbing Chloe by the back of her long black curls, Simon decided to take control of the situation, pulling Chloe's lips to her and passionately kissing her again. Simon found his hands running down the back of her dress to her pert ass as he pressed Chloe's body against his, desperately hoping Chloe wouldn't see the bulge that was growing in his satin panties. Still kissing Chloe, Simon unzipped Chloe's dress and allowed it to fall to the floor as they broke from the kiss, leaving Chloe in just a sexy black lace basque and stiletto sandals that showed the full length of her gorgeous legs. Simon licked his lipsticked lips in anticipation and Chloe smiled to see it.

Simon could do little to stop Chloe as she helped him pull his red dress over his head. His emotions were becoming confused, he desperately wanted this gorgeous dark girl, but he didn't want to reveal his true self, he didn't know how Chloe would react to it. However now he no longer had a choice, as he cast away the dress to reveal his small, feminine figure in just the dark red lingerie, his bulging member was obvious inside his panties.

"Sorry," he said, looking into Chloe's eyes as he pulled the panties aside to release his firm, hard cock. Chloe paused for a moment and then, licking her lips, seemed to make up her mind about something and, to Simon's joy, dropped to her knees infront of him.

As Sally pulled her sensual dark red panties aside to reveal a hard, erect cock springing free, Karl had realised that Jessie had set him up. However by now he was utterly enthralled with Sally, and, with the wine rushing to his head and his increasing joy in womanhood, he began to act totally on impulse, doing as he knew Chloe would do. Dropping to his knees he began to lick around the head of Sally's throbbing cock, drawing a string of pre-cum from her cock into his mouth as he had seen in porn movies he licked his lips, savouring the surprisingly good taste. Looking in the mirrors, Karl could see what looked like a gorgeous girl on her knees sucking off another sexy girl and this turned him on any more. He knew there was no turning back now and he enthusiastically, if a little inexpertly, began to take Sally's cock into his mouth and suck on it as he felt his own arousal ever growing. The groans of pleasure his sucking was giving Sally just spurred him on further, as a guy he'd never been able to give a girl such pleasure, suddenly Karl felt he was where he wanted.

Chloe's cocksucking may not have been as skilled as Sarah's earlier, but Simon was utterly enthralled with her, and was even more turned on by the reflection of them that he could see in the wardrobe mirror. It didn't take long of Chloe's eager cock sucking to send Simon over the edge and completely forgetting about Jessie as his knees buckled once again and an orgasm shook through him as he spurted his load into Chloe's mouth. Although Chloe appeared eager to swallow, her inexperienced mouth could only take in a couple of mouthfuls and Simon was experiencing one of the greatest orgasms of his life as he withdrew from Chloe's mouth and continued to squirt his warm, sticky cum all over her face and chest and into her hair.

Finally Chloe, face stained in cum, stood up and kissed Simon again, the mixed taste of wine, lipstick and his own cum was heavenly to Simon and her eagerly stuck his tongue into her mouth in an attempt to enjoy the taste of more of his juices before licking her face clean. As she stepped away from the kiss, still dressed in her black lace lingerie with her make-up smudged and cum in her hair, Chloe began to look a little bashful again.

"I've got a confession to make," she said shyly in her throaty sensual voice as she pulled her own underwear aside to reveal an erect cock, much smaller than Simon's but a cock none the less, and Simon realised Jessie must have set them both up.

However, by now Simon was fully enthralled in the experience and fully enfatuated with Chloe, so much so that he didn't care at all about her having a cock, she seemed to deal alright with his after all.

"That's alright," he smiled reassuringly, pulling her back against him and kissing her once again as he felt his cock become hard once again. He reached down to Chloe's tiny girl-cock and began to rub it, jerking it off.

Karl felt a shudder of pleasure run through his body and a moan escape his girly lipstick covered lips as Sally began to stroke his little girl-cock while she still kissed him and licked her cum from off his face. Suddenly Karl realised what he really wanted from Sally, what he knew would make him a true girl, something he knew now he wanted deeply. As Sally bent down to lick her cum from his chest, Karl leant over and whispered sensually into her ear.

"I want you to fuck me Sally, I want you to fuck my pussy like the little slutty girl I am."

Simon was becoming really turned on by the close attention of Chloe and the joy of rubbing her little girly cock, but he couldn't prepare himself from the joyful arousal as Chloe leant over and whispered in his ear that she wanted him to fuck her. He needed no more than a second to think about it. Although somewhere inside him he knew Chloe was as much a guy as he was and he knew he'd never had sexual feelings for another guy, he also knew that Chloe was a gorgeous sensual girl, just the kind that Simon was desperate to fuck and he was delighted by the offer as his cock twitched in agreement.

Chloe knelt on her hands and knees and pulled her underwear aside to give Simon access to her tight ass. Simon touched the head of his cock, now fully erect once more, against the rim of Chloe's anus and he felt a shudder run through Chloe's body. Slowly, Simon began to force his cock into Chloe's tight ass, but the vice-like grip of Chloe's ass made it hard for him. At one point Chloe cried out and Simon offered to stop.

"Don't stop Sally," Chloe replied, "I need you inside me, I want you to be the one to take my cherry, I'm a slut, fuck me hard like I deserve."

Simon didn't need any further invitation to fuck Chloe's tight virgin ass, the tight grip as he pulled his cock out and thrust it back in was stimulating him like now pussy ever could as he heard Chloe's cries of pleasure he knew she was enjoying it just as much. Looking in the mirror at the sight of a sexy buxom blonde fucking the ass of a leggy brunette, Simon couldn't help but feel totally aroused.

Karl was in heaven as Sally slid her hard, large cock in and out of his tight virgin ass, it was the greatest stimulation he'd ever had and he wondered how he'd managed to live so long as a guy when deep down his desire had truly been to be fucked like a girl. At moments Karl thought he was going to pass out from the extreme pleasure of it as his cock was already as firm and large as it's small size would allow, when Sally reached down and began to jerk him off in time with her ass fucking. This was far too much for Karl and he felt his ass tighten around Sally's cock and an orgasm shaking out from his ass through his body as he screamed a girly "I'm cumming!" and blew his load all over his chest and Sally's hand.

As Chloe's girl-cock began to twitch and cum all over his hand and her ass became even tighter around his cock, Simon too was pushed over the edge and he let out his own loud moan and, grabbing Chloe's long, dark curls, thrust one last time, deep into her ass causing her to groan again and her ejaculation to continue as he blew his load right up into her ass.

As the two of them collapsed on the floor, still dressed in sexy lingerie but stained in cum, with their make-up smudged, they heard laughter and clapping and looked up to see Jessie standing in the door with Sarah, Claire and her twin brother Jesse, all looking and clapping. They'd been so engrossed in each other that they'd both forgotten these others who now stood there laughing. Jessie had even been filming with her videocamera, having had no idea her plan could have resulted in so much. She smiled, delightedly:

"Well Karl, Simon," she laughed, "Wait until the guys at school see this."

However neither Chloe nor Sally cared any more about the humiliation, this had been the best night of their lives. Both had got over their crush on Jessie and had discovered new and greater pleasures. Their new lives stretched out before them, far more pleasurable than anything that had happened before.

THE END

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5 Comments
AnonymousAnonymousalmost 8 years ago
5+

Damn that's hot!

AnonymousAnonymousover 14 years ago
Excrutiatingly Hot!!

This story is great and extremely hot, from start to end it had my smooth little penis hard. Would love to see a sequel to this or a progression of Chloe and Sallys relationship.

Great Work!!

OhGreatOakOhGreatOakalmost 15 years ago
OMG!

This story was HOT! God my erection lasted for like an hour after reading this!

AnonymousAnonymousabout 17 years ago
New Pleasures

I enjoyed the story very much and would love to take part in a similar situation. I am a passable transgender and enjoy wearing dresses or blouse-skirt combos and heels very much!

Sincerely,

Josie of Augusta, Ga.

email: augustacd01@yahoo.com

AnonymousAnonymousover 18 years ago
Loved It!

This was the first thing I read when I came to this website. I've read hundreds more stories but this one still remains my favorite. I must of came 5 or 6 times while reading it.

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