Sarah, My First Ch. 01

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My first transsexual experience.
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This is my first submission I thought I'd kick of with one that I would love to happen to me, if you don't like transsexual/gay stories this probably isn't one for you, if it is enjoy and I hope you enjoy.

I've always wanted to enjoy another cock in my bed but never had the guts to do it I suppose it's the age old thing of the unknown.

Anyway I found myself working away on my own in London and I couldn't get the thought of another cock out of my head all day long I was quite thankful that I wasn't working with someone else its always awkward to get away from a work colleague in the evening.

By the evening I had worked up the courage to go out and see if I could achieve my fantasy, so off I went into the centre I ventured into a couple of bars until I found one that was playing some music I like (funky harmless house), I stood just off to one side in the bar with my beer one of my favourites Coors light to keep my courage up, after an hour or so I decided it was going to be impossible to pull if I was on my own I'd just look desperate for company or maybe I was just looking for an excuse to chicken out its silly really.

I thought I'd go outside for a cigarette and move on so I went out back. Just as I lit my cig I caught a glimpse of a girl out the corner of my eye there was no one else out here and I could smell the distinct smell of a cigar, now I never thought of it being a sexy thing now I should explain it wasn't a huge cigar like a Cuban maybe an king Edward, but seeing her with it was erotic and so sexy the way she took a drag and let it slowly escape her mouth and only taking back the very last bit in a deep breath then blowing it out through the smoke I was hypnotised by it.

It was then that she saw me to say I was embarrassed would be an under staightment I wished the ground beneath my feet would have opened up and swallowed me, lucky for me it didn't she just smiled and proceeded to take another drag, I tried to watch her out the corner of eye but decided it was probably best if I went to get a drink to try and cool down my cheeks as I walked to the door she called "mines a rum and cranberry, lots of ice" a little taken back I thought it was worth a shot if could get somewhere.

As I was waiting to get served I tried to think how she looked but she was just out of the light except for her legs coming out of a dark dress as far as I could tell and they were long and a defined-not muscle builder defined, just a look of strength in them.

After getting served I went outside with her drink and mine which had now become a soco on ice and there she was, moved over to where I was standing but looking away from the door, and in the light she look blinking fine, starting from where I left off, on top of those fantastic legs was a nice round ass with a definite change between thigh and ass and even that looked like there was strength in it, then her waist went in just perfectly, she had wavy brown hair that fell just between her shoulder blades.

"here's your drink" I said she turned round blowing out a trail of smoke in a semi circle, as she turned I got a side on view of her, her stomach was flat and some nice breast's a handful and a half each and very pert, her dress was almost black with a slight dark blue shimmer as I caught the light.

Her face was slight with a little Brazilian look to it with nice full lips and with it she smiled and it could lit up a room.

"thanks I was wondering if my little show earlier didn't spike your interest in me, I was nearly hurt" she laughed it was a light floating laugh that demanded I join in so I did a embarrassed quiet one, "so how come your out her all on your own" I enquired "my friends don't really like the fact that I smoke, so I came outside I like it out here as well the music's a little bit quieter so you can talk knowing my friends they have almost likely moved on to next bar. My name's Sarah by the way. What you doing on your own I saw you earlier standing near the side?"

"Nothing really working down here and fancied seeing what was going on around."

Not too bad I thought nice small talk and that's the way it continued for the next couple of hours the drinks flowed easily until I asked,

"do you wanna come back to my room?"

"Yes that sounds good" she said as she came closer to me and kissed me man her lips were extremely soft.

We left the bar and went to the nearest tube station the ride was uneventful and mostly empty of people we held hands most of the way well until we had to hold the nearest pole.

I opened the door to my hotel room went to the mini bar and asked if she wanted another drink "yes please gin and tonic"

I fixed her drink and fixed myself a rum and coke, I walked over to her she went to grab her drink and I put my hand on her hip and pulled her closer to me and gave her a long kiss that got more passionate as it went she put her drink on the nearest table without breaking the kiss, she then broke the kiss.

"It seems that it's gone further than I normally like to take it without saying this."

I remember thinking 'could it really be?!'

"I'm a transsexual, I haven't gone all the way I still have a penis and I don't think I will it's a big decision to make."

"That's fine its better than fine, your hot damn hot! Plus I've always wanted to sleep with a lady like you,

"what you've never been with a lady like me this is going to be fun"

"I've never even touched another persons cock"

"It really is going to be fun"

With that she flung her arms round my neck and kissed me harder then before and her tongue was entering my mouth and dancing with mine this was great my hands started to wonder over her body, hers on mine she pulled my shirt out of my trousers and started unbuttoning it off came my shirt, my hands found her zip at the back and slid it down she dropped her arms down and off it fell falling to the floor.

She took a step back and I took in the view of this lovely girl in front of me nice lacy bra and a now noticeable bulge growing in her matching thong, she undid my trousers and hooked her fingers under my boxers and slid them down to my feet.

There I was standing in front of her with my semi hard cock that had grown to 4 inches she run her finger nails softly up my legs as she blew gently on my cock making it grow to its full 7.5 inches and 5ich circumference, she took it into her mouth as her nails dug into my ass, the mix of a little pain and pleasure was mind blowing it was the best head I had ever had, I looked down to see Sarah had all but half an inch in her mouth gosh it was great, the suction was phenomenal, I had to pull her off it was going to end far too soon.

Sarah came up to my face and kissed me I could taste my pre-cum on her and now it was me pushing my tongue into her mouth, I spun us round and sat her on the bed she put her arms behind her and removed her bra her breasts came down a little bit just enough to make them look relish.

I pushed her gently down so she was laying down and slowly removed her thong out popped a 7 inch cock that only had little bit less circumference than mine and it looked fantastic I ran my fingers over it gently up and down it felt strange, the curve was the other way round in my hands, but it was so soft but with an inner hardness that was like steel.

I stroked my hands down the outside of her legs then up the inside till I cupped her balls Sarah moved her legs apart.

With my left hand cupping her balls softly squeezing them my right hand moved to her penis pulling back the foreskin, exposing its head I looked up to see her push her head back and let out a sigh,

Sarah looked down as I parted my lips and put her cock in my mouth it felt silky smooth I tried to suck it just like she did to me sarah started to moan in pleasure so I assumed that I was doing a good job.

Sarah parted her legs even further and my middle finger brushed against her anus she jumped I thought I'd done something wrong "Sorry."

"No it was nice before we go on have you got any lube?"

"yes I have, got to be prepared for anything"

I reached over into my suit case and found the bottle.

"get on the bed and your back." I did as I was told Sarah straddled my chest and bent down moved up my body a little bit so her penis was in front of my face moved my hand to it and took it in my mouth again as she took mine. I squirted some onto my fingers and rubbed onto her hole I felt it relax and pushed my finger just up to the first knuckle.

Then I felt something cold on my ass and felt a little surprised but it felt so nice, soon I came to really enjoy it and was moving my hips in time with her movements by this time I had the hole of my finger in her ass I felt her bite some nails off and push one of her fingers in my ass it I little painful to start maybe because I tensed up but after I relaxed it felt good like it was always meant to be there she slowly drew it out a little bit then pushed it back in I could feel her going further in with each stroke I grabbed the bottle again an put some more on my fingers and got two into her this made her moan and the vibrations on my cock made me moan soon we were panting and sucking for all our worth.

"fuck me please" she lifted one of her legs up and I shuffled out from underneath, Sarah moved onto her back I pulled her legs up so they were on my shoulders and positioned my cock at the entrance, I lubed it up and put a little pressure on her ass waiting for it to relax slowly my head went in, Sarah gasped and let out a moan, I paused for a second then pushed it further in, pulled it almost all the way out then slowly pushed my full 7.5 inch in it was so tight I started to moan as I sped my thrusting up sarah was begin for me to go faster as soon she was screaming.

I was going faster and thanking my lucky stars that I'd had a few drinks, it felt like the best shag I'd ever had.

I could feel Sarah's cock rubbing in-between mine and her bellies, "Yes! Yes! that's it fuck me good!!!!!!!" with that I felt sarah cum between as her ass squeezed my cock so tight that it was enough to put me over the edge I came with so much force I thought I was going to pass out.

Afterwards I could feel my cock soften and fall out of her as neither of us could move. We held each other I rolled off of her.

"Thanks honey that was amazing."

"thank you too that was the best" I said.

We feel asleep cuddling and stroking each others cocks.

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AnonymousAnonymousalmost 14 years ago
MMMMMMMM...if only it happened to me

If only...we can all dream.

It made me so hard

Calit69Calit69about 15 years ago
Theres much work to be done

Admire your courage in writing. Also click ditto with your fetishes. But unfortunately your story telling requires significant development, construction, grammar and spelling poor- detracts from story. No real story line. Too mechanistic without much build up or eroticism. Your character has one hell of good pick up line "do you want to come to my room" Could have been even more direct "want to suck and fuck I am as horny as a goat" Theres no build up of emotion. Ones trying to create this anticipation, headiness, sense of the unusual, but oh so sexy and pure plain lust Better luck next time

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