My First Transvestite Meeting   added 4 years ago
  By: bikerjohnny  Age: 49  Country: United Kingdom

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Categories: Oral Sex, Transvestites, Anal Sex
Tags: crossdresser Transvestite
Location: A hotel room
Roleplay: Any
Fulfillment: Act on it
Nature: Romantic

My First TV meeting
Well after a long build up the day finally arrived, a chance to meet Bella at last.

As we had arranged, I would get a hotel room in London, she would arrive, but as her alter ego, lock herself away for a while and emerge as Bella, girl next door desperate to be deflowered.
And so it went…I amused myself with some wine and some porn on my laptop whilst waiting, nerves getting to me, it was finally about to happen, what would it be like?

She emerged from the bathroom, and the transformation was incredible, no traces of her other self, just a very tall girl, looking just as nervous as me.
'God you look amazing' I managed to blurt out, and she did, simple red satin dress, red high heels to match her red lipstick and long blonde hair. Black seamed stockings, leading up to what I knew would be red suspenders and red knickers, completed the look. I could feel myself harden in anticipation, she looked relieved, and then appreciated my efforts, suited appropriately for the occasion.


We approached and I cupped her chin, drawing her in, to kiss those red lips of hers. My first ever kiss like this, and it was mind blowing. Unexpectedly soft lips, opening to my touch, a tongue just as active as mine, darting in and out of each others mouths, the sexual tension building so much inside both of us.
I guided us to the couch in the sitting area, we kissed some more, before I could take no more, and took her hand and guided it to my throbbing groin, where she swiftly got the message unzipped me and released him from his confines.

Her hand encircled him, slowly stroking him, up and down, me getting harder with each stroke, before she bent her head and without any warning, slid him straight into her warm wet mouth. I jumped a little, but relaxed into it, enjoying the experience, her knowing exactly how each lick felt herself, how each suck would almost take me over the edge, knowing the exquisite delights of spunk building up in a hard throbbing cock, it was indeed the best blow job I had ever received.
Too soon I was right on the edge, desperately holding on not wanting to blow this quick, I pulled her away, then felt a sudden need to kiss those lips again, taste me on her.

My hand went to her nylon clad leg, feeling her smooth thighs through the material, she parted them instinctively, and needing no more encouragement, my hand slid its way up. So nervous now, I was about to hold my first throbbing erection that wasn’t mine, to take it in my mouth, it was a big step for me, but as ever my own throbbing cock took control, and my hand finally found its way to her knickers, lovely silky knickers, just about containing the hardness inside.


My hand grasped her through the material, slowly stroking her, teasing her head, cupping her balls, and then it really was the moment of truth. Pulling her panties down, I released her hard cock from her knickers, it felt so different from mine, yet so strangely familiar. She was circumcised unlike me, definitely aroused, and begging for me to do something with her.

I bent my head towards her, and licking the head and shaft for a while, eventually I took her all the way in my mouth, and the feeling was so gorgeous. Couldn’t believe how turned on I was by it. I sucked her deep down, sucking  more as I came up, then down again, slowly sometimes, other times speeding up, and judging by her moans, my inexperience had gone un-noticed.
Using all my knowledge from receiving blow jobs, I proceeded to suck and lick, twirling my tongue on her head as I sucked, deep throating, everything I had been fantasizing about, licking her balls, until I could feel her swell inside my mouth, a couple of sucks later and my first taste of precum.

Nothing could deter me now, loved the taste wanted the real thing, but first another milestone to reach.
Removing her knickers, I pushed her back on the couch, knelt between her legs, pulling them back on to my shoulders, then pulling the lube from its hiding place, slipped a condom on, lubed him up then placed him at her sweet pussy hole, before gently easing my way in. I was surprised at how easy I entered her, I had been expecting some pain maybe for her, but no, I slid all the way in, up to the hilt, then all the way out again.

I loved looking down, my cock thrusting in and out, her cock straining away desperate to shoot also, her hands occasionally having to wank herself but always stopping short of coming.  Slowly at first, then faster until I was pounding her tranny pussy as hard as I have ever done, her moans bringing me on, I could feel my own orgasm approaching, and when I told her, she insisted I come on her face.


I pulled out, threw the condom away, then kneeling over her, pumped my cock fast right next to her mouth, just dying to shoot my load over her face, but just as I was about to come, she took him in her mouth, sucked hard, and brought me right over the edge, my orgasm so powerful, I couldn’t stop shooting spunk, which she swallowed wanting more the whole time, until utterly drained I pulled away.

Then the moment of truth, no longer hard myself, but faced with a throbbing hard erection, would I be able to finish her off. But just looking at her wanton look, her desperation, I couldn’t leave her like that, so taking her once again in my mouth, I sucked her sliding my lips over her head as I did, again and again, until that final swelling, and the first shot hit the back of my throat.


So wanting to do it right I just kept fucking her with my mouth tight over her cock, until she had to pull back, the pair of us totally spent now.
And that was how I lost my tranny virginity, the first of many times now, each so exciting in totally different ways…more later
J




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