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Old 11-12-2008
Arthur Arthur is offline
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Default First time -might help the nervous part 1

Hi everybody,

as it is probably the only way I can actually tell anyone about my first time with a Shemale. I dont think I am ready to confide in my wife at the moment so then at least this might set the scene for those thinking about trying this and let me tell my story which I am bursting to share.

To set my background:

I live in the UK, late 40s, happily married with no kids, professional occupation, white and male. I'm far from being a looker, but the years have been kind to me and I keep reasonably fit.......no six pack. Just an ordinary bloke really.

Married for over 15 years, never visited prostitutes, never played around. A one woman guy. Over the years I have enjoyed pornography as a leisure activity and its quite likely you would find me reading a book on Spirituality, Yoga, Therapy, World War 2, Motorbikes etc instead of attending to the internet.

Our sex life is pretty quiet these days, that's a mutual thing as there is a level of comfort now. If either of us want to make love we would, but mostly it's cuddles and playing with each other. I have a few kinks which involve a bit of enema play (we tried it together once or twice, but somehow I prefer to do this alone, I like the buzz it gives me), tried some Catheter play (just me that time as she would have nothing to do with it) and we have bought a strap on which she has used on me a couple of times but she is not very expert.

So where do I sit in the sexual frame ? Well, I like women, particularly young women and bright intelligent women. I like cocks, but not the male body that is attached to it (this is something I began to realise a few years ago and found it hard to understand exactly why that was the case). I would mostly fantasize about someone exactly like me actually fucking me (I know its weird but it was the only way I could imagine being fucked by another guy).

Then I discovered Shemale porn, and no doubt like many on this forum I suddenly wondered what exactly it was doing for me. It messed with my head. Here was what looked like a beautiful woman adorned with a cock and balls. It made me feel slightly uneasy, but there was no doubt that there was an attraction.

Over the course of a year the need began to grow and I just wondered how exactly I might feel going to my grave not knowing exactly what I missed........regret is usually for the things we dont do, not the things we do!
Of course the duality of the situation played on my mind as I realised that there was no way I was going to discuss this with my wife and it smacked of deception and infidelity.

By this time I had selected a possible escort from an internet site. She looked pretty and the reviews were good. It was daunting to realise she was kitted out with a cock that was probably a good couple of inches bigger than mine, although I suspected these credentials were prone to exaggeration.

Another year went by and I began to realise I was going to have to satisy this curiosity regardless of the risks.......oh yeah, the risks! She was not going to be as the description, it was a Police sting excercise to trap punters, I would be robbed, someone would find out, I would get an STD, all those and more....

As it happened I was attending a day conference about 30 miles away from her flat. I drove down to the conference HQ, sat outside in the car park armed with my private mobile phone and a concealed phone number. After sitting, staring at the phone, putting the number in and canceling several times I was at that point you get to on the high diving board. It was now or never and so I dialled. Half expecting no answer or an answerphone my heart leapt out of my chest when she answered and it was a great relief to find she sounded like a female. Nervously I asked for an appointment for later that day, I could hardly think straight, all I could do was mumble through the driest mouth in history. A few second later I ended the call with the appointment booked for after the conference.

The conference felt like it was surreal, I just could not concentrate. It was like being stoned and trying to act normally. My mind was reeling and I kept wondering if I should back out. What the hell was I getting into ? I must be crazy to consider going through with it. The conference was due to finish just after lunch, but was beginning to drag on while I had to keep engaging with some sensible input. I knew that I had to find the place and get some money out (wow, even this had to planned as it would be obvious that the sum had come out of our joint account, so I used my private Egg credit card so that it could be hidden in the costs).

At about 1:30pm I had the money ready, the sat nav set up and was on my way. My mind was whirling with all the things that might go wrong, I was in a daze, excited and scared witless all at the same time.

By the time I arrived it was getting late. Parking up at a local supermarket I eyed up the flat. It didn't look vey enticing and sat on top of a printers shop. Just standing around made me feel furtive and obvious, it was as though there was a sign around my neck anouncing my intentions. I went back to the car intending to see if I could explore some chinks of doubt by phoning to cancel.

I dialled the number and she answered..............

Last edited by Arthur; 11-12-2008 at 12:27 PM.
  #2  
Old 11-12-2008
CuriousJim
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Dude, part 2!? Pleeeeeaaase!?
  #3  
Old 11-12-2008
entwcu entwcu is offline
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yes this is favorite too!
  #4  
Old 11-12-2008
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Woollaine Woollaine is offline
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Married or not, the part one of your history is surely that of much d' men. It remains has to see for part 2
  #5  
Old 11-12-2008
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C'mon! Don't leave us hanging...I vote for part 2 also.
  #6  
Old 11-12-2008
Arthur Arthur is offline
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Default just before Part 2

Well thanks for the interest. I have to say I am doing this from a purely selfish motive. I want to capture how I felt and what happened in as much detail as possible. The reason it is in parts is because I do have a wife wandering around the house and it does not take much for the secret to get out. So, to part 2.
  #7  
Old 11-12-2008
Arthur Arthur is offline
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Default Part 2

she answered the phone

"Hi darling, I thought you had decided not to come so I got changed, I'm sitting here in a velvet tracksuit"

Now you have to remember just how nervous I am at this point. This is far from what I am usually like and I am looking for a way out. The flat was above a shop for starters and the thought of having to go through the shop was enough to put an end to my adventures. The windows above the shop looked dirty and unkept and all the curtains were drawn in the very worst approximation of a seedy Soho brothel complete with pimps.....not encouraging to someone who was feeling as freaked out as I was right at that moment.

so I replied "Ok, if you are busy then we can leave it to another time"

"Its Ok" she said " you will just have to give me a few minutes to put on something sexy".

My mind was turning summersaults, it just sounded so corny. I was thinking she was maybe a heavy drugs user, or a prostitute slave with an eight foot tall black pimp with attitude and a gun.

I started muttering something about the area looking a bit rough and was her flat above the shop, and how did you get to it. I thought maybe she would tell me to forget it.

She replied "this is one of the nicest areas to live and my flat is reached around the back of the shop. Give me 5 minutes and I will ring you back when I am ready. Go around the back and walk in the first black door on the left, it will be open and then my flat is straight through"

My heart was beating like a drum. I know how the soldiers must have felt going over the top for the first time. It was paranoid terror.

I waited and my mobile rang. I answered and got the curt response "ring me back". Whoaaa, I thought, this was getting very strange, but I was hooked and re-dialled.

She re-stated the directions and hung up.

I crossed the busy road into the steep cobbled back lane and followed her directions. I missed the door and ended up further down the lane, so I retraced my steps. Turning round I spotted a girl hanging around at the top of the lane and I hesitated for a moment, but she disappeared into the back entrance of a nearby restaurant leaving the lane empty.

Locating the number of the flat and the black door I quickly made my way inside.

It was a short gloomy corridor with a dimly lit glass panelled door directly in front. As I approached the door there was movement. I knocked and the door opened and I was ushered inside.

[you know that at this point I could start waxing lyrical about how she looked and what she said, but in reality I hardly cast a glance. I was worried she was going to be an absolute dog so I averted my gaze. Its funny that I should mention a dog because in my highly charged state I nearly trod on one of her pets, a tiny breed of Dog and I have no idea what it was.]

I looked over to her then, she was just under 6 feet tall.........
  #8  
Old 11-12-2008
Arthur Arthur is offline
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Default part 3

she had long blond hair and a pretty face, wearing a pair of black thongs and a black bra.

I'm into petite women so this was a departure from my usual choice and more Amazonian. Certainly attractive in the way that all shemales can be, with perfectly hairless, smooth white skin and a knowing smile.

She asked me to go straight through to a small room to the left. The room was clean and tidy with a double bed, a chair and a couple of furry pillows. It was warm and lit with a orange bedside light. There was an oil filled radiator which was keeping the room very warm.

She stood just outside the door and asked me to get comfortable as she would give me a massage to relax me. I suddenly realised the 5 cups of tea I had drunk at the conference was driving a new urgency and so I asked to use the toilet.

"Of course Darling, its just through to the right, but could we do the business first?"

I fumbled in my wallet, pulled out a wad of notes and handed them over. I pushed the wallet into my trouser pocket as I was remembering all those films where the guy gets robbed when he leaves his wallet alone. She smiled again and I just knew she understood exactly what was going through my mind.

After the toilet I returned to the room. She again asked me to get comfortable as she was going to give me a full body massage. Obviously 'get comfortable' is the code word for getting your kit off and so I stripped off while she lay on the bed still wearing the black underwear and propped up on one elbow. This was all very surreal and embarassing, so to cover things up I tried engaging in some meaningful conversation. Now usually I am a sparkling conversationalist, but honestly, the half constructed sentences that came out of my mouth were like the sort of thing I said on my first date aged sixteen.

She asked how long I had been thinking about trying this and understood how I was feeling. She said that virtually every guy was exactly the same. I was still wondering if every guy was a homosexual, bi-sexual or straight just so I could fit myself into one of the groups. Her reply was that they could be from any sexual mix and the one thing that united us all was the lure of something strange and different.

[as an aside there was a comedian on a chat show the other night who talked about shemales as the 'swiss army knife' of sexual partners, so you can tell it is popular and figures more highly than most would admit]

So I lay face down on the bed and she asked gently if I had decided what I wanted to do. That was easy, I had been thinking about it for a long time, to suck her cock and have her fuck me. She said that would be good.

She sat astride me and began to massage my back, kneading gently with a slippery film of fragrant massage oil. This was a proper massage and it was certainly making me relax, her hands moved over my buttocks and for a moment the finger tips grazed my scrotum, it was like an electric charge through my body, just like my first experience with a girl.

After a few minutes of massage and conversation (and its the sort of conversation you expect in any upmarket hair salon) I was drowsy and caught in the moment. It was like being in a film, like acting a part. She moved her weight off me and asked me to lay on my back.

Again she sat astride me, there was something sensual in the feel of her oiled skin moving against mine and the weight of her body made this far more intense.

I lay there like someone at a lap dance, just not knowing what to do until she encouraged me to touch her.

I moved my hands up her smooth thighs and around the waistband of those flimsy black panties which contained a bulge that no ordinary woman would have. Peeling the waistband down revealed her limp cock, as I touched her cock for the first time she undid a hidden side tie on her thongs and pulled them away to reveal everything.

She was shaved, totally hairless and even limp, her cock looked big. Its difficult to tell from that angle, but it was a real mans cock and not some girly thing. Her balls hung low and they were definitely big, much bigger than mine, just like two ripe plums.

She straddled me and moved her cock towards my face. This was the moment I had dreamed of................
  #9  
Old 11-12-2008
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Verry good writer, you maintain the interest.. Like the way you descrive your felling. hope the suite soon -)
  #10  
Old 02-18-2014
trannylover1 trannylover1 is offline
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Default Bring the wife she might like it.

Hi Great story You might be able to bring the wife along later. I just read a rather juicy review of one of the danish shemales Ellen/Bianca Gold I think it was on shemalewiki.com where someone had brought his wife along to play.

You know your wife best so you will be the best judge of how far you can involve her in theese fantacies.
  #11  
Old 02-18-2014
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Quote:
Originally Posted by trannylover1 View Post
Hi Great story You might be able to bring the wife along later. I just read a rather juicy review of one of the danish shemales Ellen/Bianca Gold I think it was on shemalewiki.com where someone had brought his wife along to play.

You know your wife best so you will be the best judge of how far you can involve her in theese fantacies.
This thread has been dormant for more than 5 years and the OP hasn't been here in more than 5 years. Do you really think that the OP is going to read your post?
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