Saturday 29 December 2018

Laura's Festive Sexcapades with a cross-dresser

So after yesterday's frustrations, I feel like I still had a bit of a point to prove. And although I went along to this lovely new voyeurs club just with the intention of checking it out and hopefully getting some sexy snaps, when I saw all the attention that the ladies twirling around the numerous poles were getting, I couldn't resist giving it a go myself to see what sort of attention I would get and perhaps restore a bit of my lost confidence from the other day.

My confidence was partially restored when a young lady grabbed one of the nearby seats and started watching me intently. OK, it was a started but still not progress beyond what I achieved the other day during my live show.

That duly followed as she beckoned me over to join her on her chair. Although initially hesitant as I'm not normally interested in women, the attention was welcome so I slide over beside her, even if was just to politely decline to take things any further.

Now this is where things took a turn for the unexpected... As I squinted through the dim light, it was now that I realised that 'she' was actually a he dressed up as a she.

Remembering back a year or so to the last time that I was approached by a cross dresser, on that occasion I wasn't sure what to make of it and politely declined his approaches but was then instantly hit by regret for not giving it a try. Eager to avoid a repeat of that regret, I figured I'd see how this developed.

Well, it developed pretty darn quickly!

With some slightly awkward small talk about how he had fantasied about being a woman and had finally mustered the courage to give it a go out of the way, he slide his jeans down to his knees and unveiled his rather tasty-looking cock.

Confidence was now fully restored!

As I reached over to give it a stroke to see how hard it really was, he shovelled me off the chair and on to my knees. Hint well and truly received!

I lent in to tease the head of his cock with my tongue; flicking it back and forth across the very tip before running it around the head. But before I could barely get started, he wrapped his legs around me and forced my head down, taking almost the entire length of his throbbing cock in my mouth.

Not being prepared for this, I gagged and had to force myself up for air, but I then managed to get into a steady rhythm of my head bobbing up and down.

Not being entirely comfortable in the position that I had been somewhat forced into, I pulled myself out from under his legs and tugged him over to the neighbouring bed; surely a much more comfortable location for us to go about our naughtiness.

I pushed him backwards on to the bed and slithered down to his crotch. Now that I was freed up to move as I wished, I decided to forego sucking on his cock and give his balls some pleasure instead. As I licked and sucked at them, he threw his head back and groaned with appreciation.

His groans only intensified as I then started to stroke his cock; my hand going the whole length of his shaft whilst my tongue and lips continued stimulating his balls.

Feeling adventurous, I moistened up my middle and fore fingers and lightly ran them round his anus. I gently increased the pressure and, with no objection forthcoming, I carefully forced them inside him. He grunted and his body stiffen for a moment but he then relaxed as I simultaneously pleasured his cock, balls and ass.

He then clambered to his feet, clumsily pulling my shirt off over my head as he went.

As he stood over me, he softly slapped his cock against my face. I took this as a subtle way of him telling me that he had had enough of my attention being split between three different spots and now wanted me to focus purely on cock. Of course, I obliged.

Perhaps I didn't quite receive the measure quite as intended though. As my head moved back and forth, he firmly placed his hand on the back of my head. I assumed I knew where this was coming and took a deep breath. As expected, he pulled my head in towards his crotch until my face was flat against him.

I resisted the urge to pull away for as long as I could but then forced my head away from him to allow myself to grab another quick breath. My head was forced back down again. Again, I tried to hold myself there for as long as I could but this time I lasted barely any time at all before I had to forcefully free my mouth of his cock.

I'd had enough of him trying to suffocate me with his cock so I decided it was time to move things on in a more agreeable direction. I crawled across the bed on all fours and instructed him to remove my panties so he could give me a good fucking.

He eagerly tugged off my panties and grasped me by the hips as he lined up his cock to penetrate me. He nuzzled its tip against my expectant pussy lips and then slammed himself all the way inside me.


I reached back and pressed the palms of my hands against his thighs, trying to stop him from recklessly pounding away at my pussy as his enthusiasm got the better of him. Under instructions to calm down a bit, he became more restrained as we found a much more suitable rhythm to get me warmed up with.

As my pussy got wetter and wetter he took that as cue to crank up the intensity of his thrusting, and it was not long until his was fucking me as hard as he could again. So hard that my arms buckled from below me and my face became buried in the bed clothes. This did nothing to break his rhythm as he continued to pound me from behind.

As I struggled to get back on to all fours, he withdrew from me and rolled me over. Spreading my legs wide, he climbed up between them and entered me once more.

Without prompting, his thrusts were now much more restrained. It was a welcome change of pace from what we had been doing before.

With the more sedate tempo that we had now settled into, I took it as an opportunity to take his shirt off. I grabbed hold of the hem of his t-shirt but as I started to pull it up he was resistant to my attempts, presumably because he was worried that his flat chest was not very womanly. With some encouragement he finally acquiesced though and off it came.

Inevitably, the pace eventually started to quicken once more but before it got too intense, he wrapped his arms around me and rolled us both over so that I was now on top. I used this as my chance to take control.

As I gently bobbed up and down on his cock, I could tell he was getting close to cumming so I eased back a little to draw things out for just a little longer. I'm not sure if made any difference though, as he was soon frantically shoving me off him so that he could spunk all over me.

I gave him a helping hand (pun very much intended) and with a mighty groan, his body tensed as he was about to erupt all over me.

A massive spurt of cum flew across my face, striking me on the cheek and then finding its way under my glasses and into my eye. Two smaller spurts of cum followed quickly behind; one hitting me on the upper lip and then other on the chin. 

As I continued to pump his cock, he dribbled his final drops of cum on to my chest

As I tried to lick the tip of his cock clean off any residue drops of cum, he spasmed at my every touch but that soon subsided and I dutifully cleaned his cock for him.

He then slumped down into my arms and we enjoyed a short cuddle as the post orgasmic chill washed over him.

With our encounter now concluded we got dressed to go our separate ways, me now minus my shirt which I couldn't find. One of the other punters at the club probably has a nice memento of the show we must have put on for them!

In hindsight, I found the encounter rather confusing. This guy wanted to be a woman but then he fucked me like the man that he really was. The previous time that a cross dresser had propositioned me, he was very clear that he wanted me to peg him and that seems to make more sense than what happened here.

I suppose I was expecting it to go that way this time as well, although I'm not sure why since I didn't have anything with me to peg him with. I guess I just got lost in the moment and didn't think things through clearly enough.

Perhaps, since this was his first time going out like this, it was just a case of baby steps. Having made the the first step to go out dress as a woman, maybe next time step two will be to get fucked like one.

Anyways, he left me his contact details, so maybe I'll drop him a line sometime and see if he's ready to move on to the whole pegging thing. Or maybe I'll just take my strap-on along with me next time I visit this particular club...

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