tagTranssexuals & CrossdressersCancelled Date Night Ch. 06

Cancelled Date Night Ch. 06


Colleen looked gorgeous, as hot as any girl he'd been with, including Sarah. Her face, even with smeared make up and frizzy hair, was still cute as hell. Her slim body was smooth and soft touch, the push up bra even giving it just enough shape to complete the look.

Her ass gripped his cock so tightly he swore he could feel the vibrations from her heart beating. He even enjoyed the tickling of her unbridled cock, flopping around between their stomachs.

Horny as this all made him however, Dave tried not to get carried away. He made sure his penetrations were slow and shallow at this early stage so as not to hurt Colleen.

She, on the other hand, had other plans all together. Sitting up straight, with clenched eyes and an open mouth she forced herself down hard onto Dave's cock, burying him up to the hilt. Dave yelped in pleasure and surprise and Colleen's face broke into a sly grin.

She fucked with long, forceful strokes, sliding nearly the full length of Dave's cock with each bounce. The sound of her deep groans was broken by the gentle slapping of her hard cock on Dave's stomach.

Sarah climbed up beside her boyfriend. After a long, playful kiss she draped her arm across his chest and snuggled up against him. Cheek to cheek they lay there enjoying the show being put on for them.

Colleen stared down at the two of them as she pounded away, she massaged her imaginary breats, liked her lips and made ludicrously sexy, pouty faces in between giggles and moans.

Eventually Dave couldn't contain his horniness any more. He needed to be in control. Surprising both the girls he suddenly sat upright, one arm swung around Colleen's back as he locked his lips around her surprised mouth. With the other arm he lifted his hips up off the bed and twisted his body around flinging Colleen onto her back with him on top of her.

They landed with a slap of skin and a creak of bedsprings, his tongue still in her mouth and his cock still in her ass. Colleen lay there in shock for a few seconds while Sarah chuckled beside her, she knew well what it was like to be on the receiving end of that move.

Dave kneeled up straight, grabbed Colleen tightly at the hips and just let loose, pounding away as hard as he could at the ass beneath him. Colleen's groaning reached deafening levels, she was basically screaming in pleasure at this point and had to bury her face in her hands to try to keep some composure.

Sarah lay back, watching her boyfriend intently. Her body had finally recovered from her earlier orgasm so she reached her hand down and started to gently pleasure herself to scene unfolding in front of her.

Her fingering sped up as her horniness slowly increased in intensity, eventually she decided she was ready to get involved again. She lowered Colleen's hands from her face and leaned in for a kiss. Encouraged by this, Colleen twisted slightly so she could more easily massage Sarah's clit while Sarah's own fingers were busy plunging deep into her pussy.

Dave was almost salivating at this sight and it prompted him to fuck even harder. Colleen's cock now slapped wildly against his stomach, it had of course being doing this the entire time but the increase in speed brought it to Dave's attention. Looking down at the two girls he realised that Colleen was the only one not being directly pleasured. She seemed to be enjoying the fucking immensely but, as a guy, Dave still couldn't imagine enjoying sex fully without having your cock stimulated.

So he took another bold step, crossed another line. He released his grip on Colleen's right hip and slid his hand down to her crotch. Then with a solid determination and a good deal of clumsiness he awkwardly caught hold of her cock.

It was still drenched in lube so his hand almost slipped off straight away but he managed to secure his grip and concentrated on settling into a rhythm with his fucking. Dave had thought this would come more naturally considering the number of times he had done it to himself but then he was used to holding it from the other side. His thumb pressed over the ridge on the underside of Colleen's cock as his first finger reached the bottom of the head.

Earlier he had thought that Colleen's cock was of a similar size to his own but with it in his hand he could tell that it was actually a good deal smaller, he guessed the shaven pubes made it appear much bigger to the eye.

He started with long, slow strokes. Watching hypnotically as the foreskin was pushed up and down around the head and the lube dribbled slowly over his fingers. After he got into a good stroking rhythm he managed to break his trance and returned his gaze to the show the girls had been putting on for him.

They, however, had stopped. Sarah and Colleen were both just lying there staring at him with shocked expressions. The trio had been pleasuring each other for a long time at this point but this was the first time Dave had engaged in an activity which addressed the reality that Colleen was not actually a woman. It was clear for the first time that Dave was not just ignoring Colleen's penis, he was embracing it. Literally. And the girls realised this.

Dave knew himself that this was a big step. He could no longer justify everything he'd done by telling himself that, viewing Colleen as a girl, nothing had been outside the realm of heterosexual sex. He wasn't sure if this exactly constituted gay sex but it certainly wasn't straight sex. And he was perfectly fine with that, he was having fun, why not go further?

However he had not expected this to have such a profound effect on the girls. It looked as if Colleen was actually going to cry, her lip quivered slightly and her eyes seemed very watery. If it wasn't for the massive smile plastered across her face Dave would have been worried.

For Sarah this seemed to be the kick her sex drive needed to get back into its highest gear. Her eyes had a beastly, hungry look in them and she actually licked her lips subtly before jumping at Dave. She ravished him with short aggressive pecks on the lips before swinging her arms around his neck and sliding her tongue into his mouth, kissing him long and hard.

Without breaking their tightly lock lips Sarah then swung her leg over Colleen. She scooted back slightly, dragging Dave's lips with her, and placed her dripping pussy just over Colleen's face. Colleen needed no encouragement and promptly buried her tongue deep within Sarah's lips

Dave had to lean forwards as Sarah pushed down hard against Colleen's face. He continued to pound away on Colleen's ass as Sarah's tongue invaded his mouth for progressively longer and more passionate kisses leaving them both gasping for breath in between moans and grunts.

Dave felt some fumbling by his hand and looked down to see Sarah lacing fingers with him so that she could help with the handjob. It was somewhat awkward to get into a nice stride as they were coming at it from opposite sides but once they figured the angles out it started to work quite well. Their fingers slid over each other and their hands meshed together as they pumped the shaft, they locked eyes with each other again before desperately resuming their passionate kiss.

Dave could feel the pressure building, he was nearing his climax but Colleen beat him to it. The addition of Sarah's hand on her cock had pushed her over the edge, she squirmed beneath Sarah's legs and bucked against Dave's cock, her screams of pleasure muffled by the pussy over her mouth.

Dave felt a splash of wetness strike him on the chest and begin to trickle down to his stomach. It caught him by surprise and he pulled back to see cum splashing Sarah's boobs and dripping down over his and Sarah's fingers. Colleen's cock continued to twitch and leak for several seconds, each twitch coincided with a tightening of her asshole which pushed Dave closer and closer to his climax.

Sarah climbed off Colleen's face, which right now wore a dazed but contented look, and lowered her head to Colleen's crotch. Dave felt a tickling sensation as she lapped and sucked the cum from both his fingers and Colleen's cock.

He finally reached his climax. Grunting loudly and gripping Colleen's hip tightly, he rammed into her once more and came as deep inside her as his cock would reach. Colleen was already completely spent at this point but the force of the ejaculation caused her to emit one last moan of pleasure.

He let Sarah lick the cum from his chest while he wriggled free of Colleen ass. The tickling of her tongue was relaxing but he had to stop her when she lowered herself to his newly freed cock, it was too much for his aching member to handle. Instead they collapsed on the bed next to Colleen.

Dave was about ready to blackout. He was exhausted, his muscles were burning and his head was spinning. The girls, on the other hand, were not ready to take a break yet. Colleen rolled to Sarah's side and lowered her fingers to her pussy as she pushed her tongue through Sarah's cum coated lips.

Sarah's moans brought Dave out of his trance and he kicked himself when he remembered that only himself and Colleen had cum. He was so overwhelmed by his orgasm he was neglecting his girlfriend of hers.

Shaking his head he summoned the last of his energy and moved over to Sarah's other side. Colleen was still monopolizing Sarah's mouth so instead he settled for locking his lips on her neck while his hand snaked around her hips to join with Colleen's.

Sarah slowly moved her attention between the two, letting Colleen and Dave alternate between sloppy kissing and hickey giving. This continued for some time, it usually took a good deal longer for Sarah to reach a second orgasm but it didn't feel tiring or strenuous for any of them. Taking it slow they all felt extremely at ease, the whole affair was sensual, relaxing, even somewhat romantic.

Sarah started to groan more frequently. Dave felt Colleen's hand move from Sarah's clit, it slid slowly over his fingers and reached down below where his hand was. Sarah pulled her lips away from his to inhale sharply and Dave felt some extra pressure on the back of his knuckles as Colleen's finger entered her asshole.

Dave looked to make sure Sarah was ok with this, she was groaning and breathing deeply but she gave him a nod to affirm her approval. However she needed room to breathe and so gently pushed Colleen and Dave's heads together. Colleen rammed her tongue into Dave's mouth as Sarah's fingers gripped their hair tightly.

Colleen's finger pressed up against Dave's through the thin wall separating Sarah's ass and vagina to provide the most bizarre sensation Dave had ever felt. He could only imagine what it was doing to Sarah, though her yelps of enjoyment gave him some indication .

Colleen quickly guided him into a more efficient rhythm, with them alternating their strokes into Sarah. The kiss was broken relatively by Colleen who drew back with a look that clearly showed she was thinking some very dirty thoughts.

She flicked her eyes downwards, obviously indicated to Dave to follow her gaze. He look a glance at Sarah's body where Colleen had motioned towards. It was hot, sweaty and writhing in pleasure but Dave didn't understand what Colleen was getting at.

Looking back to her she gave him the same indication, this time lowering her head to the spot and running her tongue across Sarah's breast before staring back up at Dave with begging puppy dog eyes. It finally clicked with Dave, Colleen's cum was still smeared down Sarah's chest and stomach from earlier and she wanted him to help lick it off.

Dave froze up, his fingers stopped moving inside Sarah. He wasn't prepared for this step. It was, perhaps, silly but even after fucking Colleen, even after giving her a handjob and even though he knew he was tasting both her and his own cum on Sarah's lips, even after all that this seemed like a step too far.

He knew it would be erotic for Sarah and maybe, one day, he could build up to that but right now he just wasn't able to bring himself to go that far and he was slightly ashamed of his cowardice.

Sarah noticed his hesitation, and even in her near orgasmic, disorientated state she quickly worked out what was going wrong. Thankfully she gave Dave an out, grabbing him roughly by the neck she diverted his attention back to her and enveloped him in a fiery kiss.

Dave, desperate to make up for disappointing her, returned the kiss with equal fervour. His fingers moved with a renewed vigor and Colleen struggled to keep pace as his palm slapped against Sarah's clit.

Not surprisingly it did not take much longer for Sarah to reach her climax. It was not as intense as her last orgasm but it was as much as her exhausted body could handle. Her long exhaled moan cracked and warbled with her still shaking body.

Colleen and Dave gently removed their fingers from Sarah as Colleen finished licking up the last of the cum. Then, smiling contently, Sarah buried her head in Dave's chest.

Sarah started to fall into a post-orgasm snooze and Dave looked apologetically over at Colleen.

'I'm so...'

'Don't. Please don't apologise, I understand.'

'But I just...'

Colleen gave him a look that said, in no uncertain terms: 'Shut the fuck up. It's ok.' Dave took the advice, opting instead to reach out to her, pull her close and give her a long, deep kiss.

He realised that he could clearly taste cum on Colleen's breath. It didn't taste good but for some reason it didn't seem to bother him, though the thought of actually licking it off Sarah still did. Was this just something he'd never be able to do? No, he told himself. He would get over it, next time he'd make himself take that step. He felt he owed it to both Sarah and Colleen.

Then a thought struck him, would there be a next time? It hadn't occurred to him that this might be a one night stand deal. He had been making the assumption that the girls would want to do this again yet they hadn't given any indication of this.

Dave looked nervously down at the two girls quietly dozing beside him, their sweaty bodies intertwined together, Colleen's bra the only piece of clothing between them. Considering he was originally so reluctant about the whole ordeal, Dave couldn't believe how worried he now was that he may not get to experience this again.

He tried to push the thought to the back of his mind as he pulled the duvet over their exposed skin and started to drift off. However, his snooze was not as peaceful as the two contented girls next to him. His mind was plagued with worries and fear, was he about to lose the paradise he had just found?


Thanks to everyone who has followed the story up to this point. You guys are awesome, the support has been really amazing.

Unfortunately I think updates are going to come a little less frequently from now on, I'm swamped at the moment and I also want to try my hand at some shorter pieces. However there is definitely more to come, I've some ideas for where the story is going next, it just may take some time to actually get it down. I'll try not to take too long.

Also, as usual, comments/criticism are more than welcome.


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