Accidental First Time with a TS

This is the story about the first time I had sex with a Transsexual, or should I say the first time she had sex with me!

I come from a small country town with a population of about 10,000 people and to say I don't get out much was an understatement! Being married with 4 kids is bliss for me and my wife as we are child hood sweethearts with the white picket fence big house and everything we had ever desired.

I had been offered a job 1300 miles away from where we lived and it was just to good an opportunity to not at least go and find out what they had to say, so that meant a trip by myself to the big smoke. It wasn't like I hadn't been and lived in big city's or was naïve I just had got used to small town living.

After a couple of days and meetings I was due to head back home and was feeling a little stressed, as I said I like small town living. I headed to a near by bar and had a couple of drinks and started to unwind. I had an early flight the next morning so I didn't drink much just enough to take the edge off!

i left the bar and headed for the hotel and i saw a neon sign across the street saying "Massage", still feeling a little tense i thought why not! i go inside and i am greeted by this stunning tall woman who shows me to the private room

"Take off all your clothes, put this towel on and lay face down please, I'll be back in a moment." At the time I thought it was a little odd because I had had massage's before and usually leave my jocks on but I thought what the hell. I was a bit tipsy so my inhibitions where pretty much gone!

The masseuse came back in the room and started her ritual and proceeded to massage me. "how has your day been sweetie" she asked "pretty good just a little stressed" I replied, I then told her why I was in town ect, don't know why I told her I just felt relaxed a very comfortable with her.

"Oh yes you are very tense and tight, don't worry I'll fix that!" she said in a calm a soothing voice. As she worked her way down my back and got to my butt I was very relaxed and barley noticed that she removed my towel and was massaging my butt cheeks and inner thighs. She moved down my legs and back up to my inner thighs and arse.

My cock stirred as her hands glided in between my legs and ever so slightly brushing my balls and arsehole. By this time I was a mixture of aroused, groggy and relaxed as didn't fight it when she slipped a hand under me a grabbed my growing penis and pointed it downwards between my legs and stared to stroke it, hen she stopped.

I lifted my head a saw her back to me and she was removing her clothes, I thought it was odd but in too much of a euphoric state to care! I put my head back down and continued to enjoy the experience, it was then things got hotter and wilder than I had thought it ever would.

She continued to massage my arse cheeks but poured heaps of oil down between my cheeks and began to tickle my anus and gently started to push her finger into my arsehole, I was in such a trance of horny, relaxed and obviously drunker than I first thought, I found my self pushing back a little. My cock was harder than it has ever been before so hard it was aching, all the while this stunningly beautiful masseuse was fingering me and rubbing her big fake tits on my back.

She climbed on to the table, straddling my legs, reaching in between my thigh's, stroking my now purple cock "mmm that is such a nice looking cock" she says in a seductive voice "I cant wait to see it shoot a load".

I felt some pressure on my arsehole again while she poured more oil in-between my checks, I pushed back as it felt sooo good before, but this time it was something much bigger than her finger!

It felt a little uncomfortable but still felt good as she slowly pushed deeper and deeper into my arse until she stopped and leaned over and whispered "does my cock feel good?" I just nodded my head and pushed back, pushing her big love meat deeper in my arse.

"Fuck that feels goooooood" I yelled " fuck my arse" as she her got faster, I pushed back more and felt like I was going to explode as I had positioned us so I was in full doggy style while she went to town on me. I looked down in between my legs and my cock was dripping cum like a leaky faucet.

I couldn't take it anymore I was in such ecstasy, I could barley get any words out but managed to say "I'm gunna come!!" With that she flipped me on my back, grabbed my ankles, pushed them over my head, and slid her what I could see now was a glorious cut 6 inch cock back into my hole.

Staring at her athletic body with amazing dd fake tits, that had a little bounce with every thrust into my man pussy, I was in heaven. She reached down and stroked my cock and looked me in the yes and said " i want us to come together" and sped up her thrusts which in turn sped up her strokes of my purple love rocket

"Oh fuck I'm going to come" I moaned, she squeezed my cock and I could feel her cock unleash ropes and ropes of glorious cum into my virign arsehole, and with that I exploded thick cannon balls of jiz all over her tits and stomach.

She ran her fingers over her body collecting my seaman and sucked her fingers moaning. "that was amazing baby, your hole is so tight" she said smiling at me, "it should be I have never done this before" I said hazily back "mmm baby are you relaxed? I told you I would take all your stress away" and that she did.

I took the job in the city and am now a very regular client of this amazing masseuse my wife cant believe how relaxed I am and how much I love working and living where we are now.

She will never know about my secret stress reliever!"