First time -might help the nervous part 1

[Arthur]

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..............

Dude, part 2!? Pleeeeeaaase!?

[entwcu]

yes this is favorite too!

[Woollaine]

Married or not, the part one of your history is surely that of much d' men. It remains has to see for part 2

[studformtf07]

C'mon! Don't leave us hanging...I vote for part 2 also.

[Arthur]

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.

[Arthur]

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.........

[Arthur]

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................

[Woollaine]

Verry good writer, you maintain the interest.. Like the way you descrive your felling. hope the suite soon -)

[tlover]

Arthur this is a excellent post.
I can see some of myself in you and my feelings where very much the same as yours when i first encountered shemale porn.
Worrying about my sexuality, not wanting to go to my grave without trying it out, worrying about all the risks, all things that have run trough my mind over the past couple of years and i think alot of the tgirl virgins on the forum too. So your story is of great interest and you tell it so well.
I almost felt im there with you your descriptions of the events are so vivid.
I have imagined trying to contact a tgirl and some of what you've said about your experience is almost exactly how i imagined the events would unfold and how i would react and feel in that situation.
So im totally griped, i can hardly wait for the next installment.
Great work and thanks for taking the time (and the risk) to tell your story, much appreciated.

[Arthur]

Thanks again for the encouragement. I'm glad if it helps others. It is a selfish attempt to get my thoughts down in a place that will only be found by those with similar inclinations. It is 'no holds barred' and is exaactly how it happened which is why it reads like it does. I couldn't sleep tonight thinking about the next part. It is a delicate subject and needs to be covered.

[Arthur]

........well, almost like my dreams, because they contained a cock enshrouded in a condom. This was the real, flesh on flesh contact.

She warned me to be careful with my teeth, I nodded and greedily sucked her cock into my mouth. At the same time I fondled that huge velvety sack and heavy balls. In hardly any time at all her cock began to stiffen and I had to force my jaws wide to accomodate the growing girth. Of course the inevitable happened, cock to teeth contact, at which point see suggested laying down on her back to make it easier......and less painful.

Laying back with her legs apart, that big cock must have been about 8 inches long and well proportioned. This is where I decided to really live my fantasy and take plenty of time to really get to know this cock. Of course I sucked and licked and fondled, but really that is just the actions......I could easily be describing eating an ice cream.

Well, unsuprisingly its nothing like ice cream, that warm smooth head resting against lips and tongue it felt a complex structure. Some say its like sucking a thumb, but thats not my experience. Firstly, it's male, it sounds obvious but it has a taste and a smell that announce it is a male part. The taste is subtle, but I found it was quite distinct. Also, when you suck on the Glans it becomes really slippery. It's all very familiar and unfamiliar at the same time. If you have had oral sex with a Woman you will recognise a similar slippery feel in the mouth, the complex folds of skin and the subtle scent and taste. Imagine that as an erect Penis with the scent and taste being different and you are about there.

I was really conscious of the lack of a condom and the more I used my tongue to trail up and down that beautiful shaft of flesh, the more she moaned gently and I had no idea if it was just for my benefit, although it was pretty difficult to ignore the fully erect cock. Also, I had read somewhere that escorts generally only cum towards the end of the evening. Anyway I was scared of her cumming in my mouth, although if I could have guaranteed it was safe I would love to have taken her to climax. So I slowed down and just savoured her cock as it began to soften in my mouth.

She asked if I wanted to be sucked, well, by this time I was on a head trip like no other and all I could do was gasp 'yes'. She put a condom on me and began a really gentle and erotic oral massage. I could not really get stiff, somewhere inside my head a voice was yelling 'thats a guy sucking your cock', but in another way it was so nice it hardly mattered. I went back down on her cock and completed the 69. I could have gone on like that for hours, but this is a 'time is money' situation and we had to move on to the next stage.

"Do you want to try letting me fuck you now Darling?" Wow, this was the main course and wild horses wouldn't have stopped me.

"Have you had anything like this up inside you before ?"

"Yes" I replied, "Not the real thing, but the odd dildo". I thought I would manage her, but that cock was far bigger than the Dildos I had used. She had a real pornstar cock, the sort that you wonder if the filming just makes it look large, the sort that makes the pornstar queens gasp, gag and scream. Whats more it was about to enter me.

"The best way is doggy fashion, you know, from behind with you kneeling"

She moved me into position.

"OK open your legs wider and push your bottom into the air"

She pushed my head down into the pillows. I felt like a frog, I felt exposed and I felt ready for the feel of that cock inside me.

Now, my wife has had a go at penetrating me from behind, she lubricated me and had a go, so it was far from an unusual situation, although the position i was in was very much more open.

She began by massaging lubricant around my anus. She was incredibly gentle and the cool lubricant dribbling down onto my ball sack was totally wild. I could feel her finger beginning to penetrate me, forcing in more lubricant. As he finger slid deeper I could only groan in total ectasy. After loosening me with her finger she withdrew and wiped the excess lubricant on my cock and balls, I felt like a cow being readied for milking. Here I was, bottom in the air like a little slut and as rampant as hell.

Behind me I heard the snap of rubber. I asked if she was using a condom and made a joke about being careful she didn't get me pregnant She laughed and said that would never do.

I felt the tip of her press against my anus.

"OK, just relax and push back against me, go at your own pace, just as much as you can manage comfortably"

Well, I wanted to manage the whole thing comfortably, or not. Jesus, I think I was ready to be fucked by an Elephants trunk by that stage.

I did what she said and felt her begin to open me up. The tight muscle gave way and allowed the head to push inside. God it was heaven, I kid you not, it is one of the most erotic things ever and I was panting for more. Pushing back harder I felt her slip fully inside, leaving a dull ache somewhere deep inside me.

"Now, you can slowly slide up and down while I keep still"

Fuck me, sliding up and down that shaft, trying to gauge when the tip would pop free was so bloody hot I was on fire. When she was fully inside me I reached between my legs and found the soft folds of her ball sac and gently fondled the contents. She was buried up to the hilt, balls tight against me.

"Do you want me to fuck you?"

Oh yes please and can you fuck me until my head falls off.

She put her weight onto my back and I could feel her breasts against me. Then she started to fuck me, each time she was fully inside I could feel the stubble from her shave cock pressing against my bottom. At this point I am lost for words, it really was impossible to describe, it almost brought me to tears because it released a wave of emotion that must have been hiding for years.

Up to now, I really have not mentioned her age. Well she is mid twenties I would guess. Smooth, faultless skin, toned but not muscular and very strong and fit. A slim, petite ladyboy might seem the best choice, but if you want fucking in every position possible and as deep as possible then this woman is the ideal choice.

On the side, legs over her shoulders, upside down.......it was a real effort to keep up with her boundless energy and incredible fucking power.

We finished off back at doggy style with me controlling the pace again while she reached around and wanked me off. It was so incredibly intense, you have to experience it to know just how intense it gets, I was transported to another dimension as her hand massaged my cock faster and faster and her cock butted hard agianst my prostate gland. Eventually I let go and delivered a pool of cum which looked like the efforts of at least three cocks, not just mine.

"What was that like, did you enjoy it?"

"that was fantastic, better than I could have imagined" I replied.

"It's so much more intense when you cum" she said and grinned like a Cheshire cat.

All the way through she had been telling me how I was enjoying her big cock filling me up and I could not disguise that fact.

We finished up and she handed me a wet wipe. I began to get ready.

"Would you want to try that again Darling?" she asked.

"I dont think so, I think I fulfilled my fantasy, got it over with"

She grinned again. "I think you will be back, give it six months and the thought will start going around your head"

"Well, you never know" I said and she just laughed.

I said goodbye and left.

[Arthur]

I was back in the car and travelling home. My head felt clear and I was so relaxed and pretty stretched, it felt like an intense gym work out. My mind was one place trying to get to grips with the experience, it was dream like.

Something jerked me back to reality, it was the heady scent of the massage oil. Bloody hell I thought, I need to get back home and scrub this off me before my wife comes home. The traffic was heavy and about half an hour away from home my mobile rang.

It was my wife "where are you" she said.

"About 30 minutes from home" I replied.

"Oh looks like you will beat me home" she said.

Turning the corner into our street, I noticed her car was not yet back. I flew around the house, showering, getting rid of any item of clothing that smelled of oils. i was convinced it was still strong enough to smell a mile away.

Anyway, I made it, no harm done. Strangely I feel totally guilt free and somehow more in touch with myself. More powerful somehow, its weird.

I think it has helped me to be more in touch with my wife's sexuality and less scared of male sexuality. A sort of cathartic liberation.

The thing is. She was right. Once you have tasted that strange fruit I think I will need to try it again, at least once more

[tlover]

Thanks again Arthur, that was a very frank and powerful account of your encounter and very erotic, thank god it ended on a happy note.

Even if it was partly written for selfish reasons i think you've given all of us tgirl virgins a good idea of what we could expect and for me the prospect of my first experience doesn't seem quite as daunting now.
I hope its helped you to get it all off your chest so to speak.
I'm sure you will be going back for seconds some day and i really hope you tell us about it.
Please keep posting there must be other things you want to get off your chest

[maxxluv]

Great story well written, i .oved it. She is right once you done it goes around your head. Coming back when you least expect it. Since my first tim about 18 months ago ive been back 3 times.

My first time was as great as yours, but the last time was amazing.

male from london

[franalexes]

Thanks for the story. Now Ila has something to go by.
I'm ready.

[ila]

Originally Posted by franalexes

Thanks for the story. Now Ila has something to go by.
I'm ready.

I'm always ready.

[franalexes]

Originally Posted by ila

I'm always ready.

<sigh> Damn Canadians. First thing they need is their special* brand of maple syrup.

[hankhavelock]

Arthur, that's a wonderful description - I remember something similar mindwise the first time I as a rather young man decided to visit a sadomasochistic club in Copenhagen ;-) And once inside it was ofcourse totally un-dramatic :-)

My first encounter with a transsexual woman also did give me some funky butterflies in my stomach, though not to the extent that you describe. But you did it, and my goodness, you should write novels. You have a way to build up a totally "I-am-there-with-you" scenario. Talented!

It will be easier next time... but then reality sets in. Is this something you want to keep a secret to your wife? The butterflies you had in your stomach getting prepared to meet with your first transsexual date are NOTHING compared to the ones you will have when your wife finds out about it, mano...

So plan a little ahead!

But a wonderful account that I'm sure hits the head of the nail for most guys!

Respect!

H

[randolph]

Dear nervous,
A great story, well done and very exciting! Reminds me of some encounters in the past with females. I am with you in this fascination with shemales. Its like a drug addiction the more you think about it the more you want it. Just thinking about a lovely shemale standing in front of me with her hard erect cock pointing at my mouth gives me a hardon. Why is this so desirable? One thing is that you know she is horney, something you don't know with a female.

[asefase1]

i hope i will soon be able to share in detail my first sexual encounter with a tranny. i have dreams all the time which hopefully means it'll happen soon

[trannylover1]

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.

[ila]

Originally Posted by trannylover1

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?