Sunday, 7 April 2019

Laura's Sexcapades with a cross-dresser


Back around Christmas I had an interesting hook-up with a cross-dresser who at the weekends goes by the name of Wendy. When she originally hit on me, she piqued my interest because I had no idea how being with a cross-dresser would play out.

In the end I think I felt like it was a bit of an opportunity to experience something new missed because she just ended fucking me with her cock and it might as well have been one of those days of the week with she's a he.

I bumped into her again this evening, and when she asked if I was interested in hooking up again, I invited her back to my place, saying only that I had something a little different in mind from last time that I wanted to try...


Upon arrive at my place, I disappeared into my dressing room while Wendy patiently waited in my bedroom, before reappearing wearing that little something that I had in mind. (Actually it wasn't so little)

As she eyed the size of my strap-on, I could see a look of apprehension in her eyes. Nevertheless, she unbuckled her jeans and wriggled them to the floor as I approached and kissed her tenderly to put her at ease.

She spun round in my arms before sliding her panties down to her ankles, bending right over and giving me an irresistible view of her tight little butthole. I seized on the opportunity and eased my lubbed up strap-on into her. A surprised gasp escaped her lips.


At Wendy's insistence, I took it easy with soft, shallow thrusts from behind but as her ass became more accepting of my strap-on, I asked if she was ok with me stepping it up a gear. Again, she was slightly hesitant but consented.

In my enthusiasm, I possibly got a little carried away and stepped it up a few gears rather than just one. As I put more force into my fucking, Wendy was unable to keep her feet and toppled forward on to my bed. Clinging on around her waist, I fell on top of her and, without so much as a pause, continued plunging my strap-on into her.


She writhed and wriggled underneath me but her moans and groans of approval made it clear that she was enjoying what I was doing.



As Wendy's wild bucking started to subside, I eased back my fucking and, gripping her hips, I pulled her up onto her knees. Holding my hand aloft, I unleashed a series of hard spank on her ass cheeks.


With her now on all fours, I could feel my strap-on not moving with quite the same freedom as it had before. Pulling out of her a drooled a generous helping of spittle onto her butt hole and spread it all around with me fingers.

Before plunging my strap-on back into her nicely re-lubbed ass, her dangling hard-on was just too tempting and I couldn't resist the temptation to give it a quick stroke.


I guess she fancied a slight change of pace, as she rolled over and encouraged me to play with her cock a little more. I was a little reluctant because I wanted tonight to be all about her taking my strap-on but she has been a good sport so far, so I obliged.

My tongue flicked back and forth across her balls before I gently gave them a little suck. Any spittle that escaped my mouth was allowed to trickle down to her ass where my fingers guided it in and around her butt hole to keep it nice and wet ready for when I penetrated her again.


Finally, her respite from my strap-on was over, as I crawled up between her legs and eased my strap-on back inside her. The spittle did a fine job of keeping her lubbed and my strap-on was freely being accepted once again.

Having gone hell for leather already, I elected to take things a bit steadier now, as our bodies quick quickly started to move in unison.


However, having teased her cock with my hands and tongue, Wendy seemed to be more interested in some cock action than ass action. Wrapping her arms and legs tightly around me, she abruptly rolled us both over so that she was now on top of me.

Licking her fingers to give them a generous covering of saliva, she climbed off my strap-on, hastily moistened up my pussy with her fingers and then proceeded to drive her cock deep into my me. With each thrust, I took the entire length of her cock as she used all her weight to drive it deep into me. After each deep thrust, Wendy would slowly pull it back out before ramming it back inside me, her balls slapping hard against me.


I moaned and bucked with pleasure but again, I insisted that this was supposed to be about me fucking her, not vice verse. Although clearly disappointed, Wendy pulled out of me.

She spun round to wiggle her butt enticingly at me. As I reached forward to squeeze and then spank it, she batted my hands away. After another generous helping of spittle, she lowered herself back onto my strap-on, and with a devilish look in her eye, she started to ride me.

For the first time, Wendy was in control of exactly how hard she was being fucked, and she did not hold back, gleefully rocking back and forth on my strap-on much to my delight. My lust got the better of me once more as a I reached forward and grabbed hold of her hips. Yanking back sharply, I pulled her backwards on top of me. It did nothing to break her rhythm though, as she continued to bounce up and down on me.


As we continued to fuck,Wendy made several aborted attempts to stroke her cock whilst balancing on just one hand, However, the intensity of our fucking meant that each time she would quickly have to go back to using both hands to support herself to prevent her from collapsing on to me.

Taking a hint, I finally relented and decided that her cock could have the attention that she obviously was craving for it. As a compromise, I manoeuvred her onto her back so that I could simultaneously fuck her ass and jerk off her throbbing cock, and she was loving every second of it.


Not knowing how long she had left until she would blow her load, I conceded that her ass had probably had enough and it was time to bring things to a conclusion. Pulling out of her for the last time, I saddled up on top of her and carefully lowered myself onto her cock.


I had barely got into my rhythm when she kicked me off and manhandled me onto all fours. A vicious slap to the ass followed. I guess I deserved that from earlier...

As she teased the head of her cock against my pussy lips, she firmly took hold of my hips and jerked me back on to her cock. My pussy swallows it whole. She rocked me backwards and forwards, whilst also thrusting her hips to generate some extra force. My moans turned into screams as I implored to fuck me harder.


She suddenly pulled out from me. I expected to receive a face full of cum, but instead she rolled me on to my back and climbed on to my stomach. She tugged my tube top down, and moments later her cock was between my tits. Using her thighs to gently squeeze my tits together, she did her best to try to titty fuck me. My attempts to split down on to my chest to provide so much needed lubrication were forlorn as my aim let me down time and time again.


Wendy's body started to tense and I prepared myself for the inevitable cumshot.

She hopped off and pulled me up to my knees. With both hands, I furiously beat off her cock and, within a matter of seconds, a shot of cum streaked across my face, splattering against my glasses and forehead. A second and third shot swiftly followed but, with less force behind them, I was able to catch most of the cum either in or around my mouth.


She massaged a last few extra drops out into my mouth and was then spent.

Wendy slumped down into my lap and, as she lay there panting from her exertions, I lent my head forward over hers and slowly opened my mouth. I'd not swallowed a single drop of her cum so it slowly started to trickle from between my lips. Wendy opened wide and caught all of it in her mouth, before swallowing hard to gulp down the whole lot.


And with that, she got dressed and departed, walking slightly awkwardly as she went.

(After having two very different encounters with Wendy, I wonder if I should make it a hat-trick and seek her out on a weekday when she is a he?... It would certainly make my choice of pro-nouns a lot easier as I'm still not sure if I should be using masculine or feminine ones for when he / she is Wendy)


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