This is a work of FICTION for ADULTS only. Do NOT read this if you are under 18 or if you are not an adult according to the laws of your state or country. Do NOT read this if you are offended by fantasies involving sexually explicit material.

Comments welcome to bethjac@hotmail.com

A series of stories with TG themes, dedicated to women, and to men who like to be women (which includes me!)

 

I Is For Isla - And The Double-Glazing Man

Bethany Jacques

 

It was all down to 'Jennie', really. If she hadn't reacted so clearly and positively when I'd suggested we should meet, things could have - indeed would have - turned out oh-do differently.

I'd actually been in touch with her for several months by that time, chatting and sending emails and pictures and so on. You know the sort of thing. Oh, and doing role-plays too in a chat-room, sometimes me being the woman, sometimes her. Occasionally both of us, wanking off in a pseudo-lesbian roleplay where I virtually fondled her legs, slid my fingers up her virtual thigh while we virtually kissed and fondled each other's virtual bodies. The one I liked best was when I played the housewife and when Jennie, or rather John, was some sort of salesman visiting and being attracted by my voluptuous figure and my feminine charms, and ....

Anyway, it was Jenny who suggested the meet one day when we were 'chatting' online. We'd vaguely tried to arrange it two or three times before, always hitting the two-wife problem. When her wife, John's that is, was away from home, Carol wasn't and indeed needed my attention, for decorating or entertaining or going to the cinema or whatever. And when Carol was maybe at her Mum's for a night or two, Mary wasn't. John's wife, that is, if that's her real name. I think it probably is.

Then when I'd mentioned something about Carol being away for three nights in a couple of weeks, we realised that for two of those nights her absence coincided with Mary's college course meetings for a whole week. Two nights. Overlapping. Friday and Saturday. We could meet.

Right at that time, what with work and Carol's preparations and me helping her I didn't have much chance to contact Jenny or sort things out until the night before. We met up in 'our' chatroom and made the final arrangements. She had met problems trying to visit me, basically she - or rather he - had to meet a client the next day and really didn't want to risk anything 'feminine' occurring. So we decided, for this first meeting, that he would come to my house in male mode, and just meet 'Isla' rather than Ben. We'd both agreed, several limes in our chats, that meeting either M-F or F-M would be most fun.

<Isla> What shall I call you, then?

Since Jenny would be in male mode, I'd obviously need to use a male name for her. Him, I mean. I'd clearly picked a femme name a bit similar to my male name, I just didn't know about Jenny. I'd always called her Jenny. Was he James? Or Jeffrey? Even Joshua?

<Jenny> Call me John. OK?

I didn't know if that was his real name, but it didn't matter, did it. John was fine by me.

<Jenny> And how are we going to do this? How about some roleplay, IRL this time?

<Isla> OK then, what do you suggest?

<Jenny> How about I be the salesman? OK?

<Isla> OK, sounds good to me.

<Jenny> Got to go. W.

Jenny's name disappeared from the chatroom. W. That meant wife. So Mary had interrupted him, or more likely he'd heard her on the stairs and off-clicked the chatroom straight away, maximising something else, a letter to his mother or something. OK, so we're both trannies and both rather devious. After all what was I about to do? Entertain a man in my own home, someone Carol didn't know about, and someone she'd be very upset about if she knew. Specially if she knew what I'd be wearing to entertain him.

I closed down myself, then sat there for a few minutes thinking. The roleplay, in real life, the thought did excite me. It's one thing doing it on-line, you can lie about all sorts of stuff or rather just pretend. To be wearing something sexy like fishnet stockings, or even go on about how big your boobs are and how you're feeling your vagina and so on. But to do it in real life, the rules would have to be a bit different. If I was to be the housewife I was going to go for the sexy housewife, short skirt and high ells and so on, and flirt massively with the 'salesman'. I shivered at the thought.

Because something sexual was almost bound to happen. I'd always thought of myself as 'bi-curious', that's the phrase everyone used, not exactly gay but .... I'd never actually done anything about it, never needed to, in fact I'd never even been out of the front door in femme mode. Just minced around and posed and so on in front of the mirror and so on. OK so I wouldn't need to go out since - John - was coming to visit me. But I was determined to do as good a job as I could.

And I did. I pulled out all the stops, as it were. You know the sort of thing, ultra-short and indecently tight skirt, very high heels, heavy make-up, all the features of the caricature tart. At last I was ready. I did one final inspection in the mirror, turning and twisting to inspect my hourglass figure as best I could in the big mirror in the hall. I noticed the clock. Ten to. I shivered. I crept into the kitchen and took the bottle of white wine I'd opened out of the fridge. I poured myself a tall glass and sat at the kitchen table, legs crossed in typical tranny fashion, sipping it, trying to breathe calmly. Was I really going through with this? Too late now, 'John' would be here in a few minutes if he got the directions I'd given him right. It was nearly five-to on the clock, I took another deep gulp of the wine.

The doorbell rang. He was early. I very quickly looked out of the kitchen window, carefully. Yes, a red car parked just outside the gate. He was here. I didn't have time to check in the mirror. I opened the front door.

John was stood there. He opened his mouth to say something, then really saw who he was visiting. He 'froze'. Not surprising really given the circumstances. I had to jerk myself into action, OK, so I was the housewife.

"Yes? Can I help you?"

"Er - yes. I'm John Green. I notice you have full double-glazing here, I was just wondering - have you a conservatory already? We're doing a special offer in the area."

Conservatory. Nice touch, John! "Er - no, we haven't. Do come in. Mr Green." I moved to one side to allow John to pass, then shut the door behind him, making sure the little lock engaged. Not that anyone was going to come in, of course, but I needed to be sure.

"Come on through into the lounge. I'm Isla. Isla Jacques." I held out a hand, John shook it gently. A had to smile when I saw John's large male hand take my own, with its long, long red nails, it really had been great doing them.

"Please sit down" I said, offering him the sofa. "Can I get you a drink? I've just opened a bottle of wine, or would you prefer beer, Mr Green."

"Er - no, wine will be fine thanks. And it's John."

Of course it was. I smiled at him, maybe a little conspiratorially as I handed him the wine. "So, John, come and have a look out of the lounge window. What about this conservatory, then?"

We stood side by side looking out at the rain, I thought John would go into some sort of spiel about letting light in or something like that but he didn't. He just stood in silence, apparently staring out of the window. After a couple of minutes of this rather strained silence I sat down facing him and finished my glass. I crossed my legs - like you do. And he almost choked on his wine.

"Look, Mrs Jacques. It is 'Mrs', is it?"

I showed him my left hand, with my imitation wedding ring on the third finger. I decided the silence had to be broken. I reached out a hand towards him. "But my husband isn't going to be back for a couple of days. So, John, come and sit here, beside me. You seem ever-so quiet."

"It's just - Isla - you're not quite what I expected."

"In what way?" I asked quietly.

"Well, on your own at home, Isla, and looking so attractive, I mean ..."

Afterwards, a couple of days later, I got to wondering just how things might have turned out differently. He seemed to be about to embark on quite a long speech about what he expected and so on. But I interrupted him. Like any tranny in that situation I wanted him to tell me just what he did think, in what way he found me attractive. I mean, at that moment, I myself had no doubt at all what I looked like. Of course I'd have preferred to look convincing rather than attractive. Many trannies want both, just the first would have done me. Just so long as convincing didn't have to include ugly, of course.

"Attractive? What do you mean?"

John changed tack. Maybe the wine was getting to him, just a little. "Well you really do have a very nice figure, that tight top is very revealing."

I realised I'd not really explained my obsession with breasts to John in our online chats. I'd been so thrilled to find such a well-shaped pair of breast-forms in a flesh colour which so closely matched my own on-line, and also to find on a web-site somewhere - I think it was 'Terri's TV Times' - some very clear and simple instructions on how to use just a small amount of make-up to blend in the edges of the falsies.

But the wine was getting to me too. "Do you like them? My breasts, I mean, you think the cleavage looks good?"

By which I meant 'convincing'. Again, later, I realised he had interpreted 'good' differently. "Oh, Isla, they look totally gorgeous." And his hand moved. Just a little, towards them. I didn't realise then why he was hesitating. It had been clear to me from our online chats that this afternoon may include some sort of sexual involvement. I really did expect him at that stage to reach out and cup them, maybe to see just how realistic my boobs felt. But he didn't, maybe he was shy.

I realised again I was going to have to make the running. I re-crossed my legs, allowing my red-tipped fingers to push the hem of my skirt up just a little to provocatively reveal just a little of my stocking tops. I didn't say anything yet, but John just gulped. I decided to take the roleplay forward, to maybe tease him a little in the way I had done when we'd acted out a scene very like this online, when he'd 'visited' me as a horny, lonely housewife.

"And my legs, John, do they appeal to you too?"

"Oh my, yes they do. Certainly."

"Tell me John, when you've been out selling your double-glazing, do you often come across women alone in the house, dressed in tight tops and mini-skirts?"

"Well, not usually...."

I cut him short again. He really was being rather slow, this wasn't just shyness. Still I continued our theme. I reached across and took his hand and placed it on my thigh, well above my exposed knee.

"And do the women you meet ever make advances at you? After all, you're a very handsome man, John."

"Really, Isla. I don't think ..... Oh hell!"

And he kissed me. Basically he snapped. He'd clearly been wanting to go on, to carry on the role-play or so I thought. But suddenly he'd had enough. Basic animal instincts took over. And as soon as my lips touched his, at the moment I felt his hand slide up my skirt, I snapped too.

"Oh my God, John, my darling, I want you. So much, you really must - ooooooooh!"

His hand had slid round the back and was clutching my arse as his lips worked on mine. 'OK so this may well have be the first time he's done this with a guy', I thought, 'but he's up for it now, whatever was slowing him down earlier.'

And within seconds, there on the sofa in the living room we were at it. On the way to my first taste of sex with a guy, I knew I was going to enjoy myself. OK, so he was about to cheat on Mary, and I was going to be unfaithful to Carol. But for the moment neither of those seemed to matter. Right then I was playing at being a woman, and a horny woman at that, eager to get screwed by any salesman or visitor who I could get onto my sofa.

I realised it would be better not to mention either Carol or Mary at that point. Maybe he was having similar thoughts but I didn't want to spoil the illusion we'd created. I was the horny housewife, so ...

I slid my hand down to the waistband of his trousers and undid the zip, sliding my hand in to grab his now-fully-erect cock. "John, please, I want to - well, you know."

Clearly John wanted to too. Within seconds he'd undone the small buttons down the front of my blouse, and was fumbling round at the back to undo my bra. As it fell off he cupped my right breast, oh-so gently at first and then more firmly.

"Oh Jeez, Isla..."

I was amazed, John was doing so well. I grinned at him, OK so if he could be the randy salesman I could be the willing wife. I smiled a knowing smile at him.

"Well, John - er - since my husband isn't going to be back for such a long time ...... "

I left it to him to carry on with the roleplay, maybe to say something like 'No, I can't, I'll lose my job' or 'but Isla, I'm a married man' or something like that. But as I slid my hand down again to stroke, for the first time, a man's engorged prick - he just groaned as he buried his head in my neck. Maybe he didn't want to carry on the role-play any further. Maybe he just wanted to fuck.

But as he got more and more into it, as I nearly ripped his shirt off and his hands groped higher and higher up my thighs, he got back into it.

"Are you sure, I mean, if he comes back, I could get the - OH!"

I'd just gone the final step, just finished undressing him, just leaned down to suck the bulging head of his cock.

"Don't worry, my love, we won't be interrupted. So, you want to fuck me?"

I realised something was going to go wrong with the roleplay. When the contents of my thong got revealed we couldn't pretend any more that I was a real housewife. Hell, by then it wouldn't matter. The roleplay was to make us both feel a bit more comfortable in the initial stages of what was, after all, the first gay meeting for the both of us. And by the time we were both naked or nearly naked - for some reason I desperately wanted to keep my stockings on - the roleplay really wouldn't be relevant any more. My excitement was mounting.

I looked down at John, naked on the big sofa, at his swollen prick. "Ready my love?"

"Er - ready."

I lifted myself up on my knees, sitting astride his thighs. I undid the small ties at the sides of my thong. I slipped it off and almost simultaneously leaned right forward to kiss him again. I sat up again.

As we separated I looked at him, imploringly, hopefully being the housewife-who-wanted-it, somehow wanting the roleplay to continue. He looked at me. At my made-up face, at my rich smooth, gorgeously made-up lips. Then down to my bulging 'boobs. And then - down again. The role-play had to change direction in some way.

"What's wrong, John? Never seen a housewife with a cock before?"

"Er - no, I haven't."

I decided to push on, to make the most of the opportunity. John did in fact look a little disappointed. To be honest I'm not surprised. Though I was obviously erect, having indulged in such erotic foreplay, I had known that he might be disappointed with my own cock. In fact it just didn't compare with his, it was fully three inches shorter, and not quite as thick. OK, so it wasn't the biggest or the thickest in the world. But it was erect, and I was horny. Since he was being the guy, and me the girl, our next step was obvious.

I lifted myself up onto my knees and shuffled forward a little. "OK John. Fuck me."

And I lowered my arse down onto his erect prick. He jerked a little as it began to slide up my lubricated arse, not surprisingly. Neither of us spoke, we were too busy! Within seconds - he was right in! I was overjoyed, I just had to show my appreciation, I kissed him passionately again, gently scraping my long red nails down his back as I hugged him. We rolled over, I was looking up - at my lover.

"Streuth, I never thought! Oh my God, that is so gorgeous!"

I was thrilled. I - Isla - was being a woman and was satisfying a man! Soon he was plunging his gorgeous hot cock deep into me, sliding up and down and moaning in an ecstatic state comparable to my own. I just couldn't stay quiet.

"Oh God, John, YES! Cum up me, cum hard up my cunt my lover!"

And he did. I knew the neighbours in the adjoining house were away, lucky for me that they were. They'd surely have heard the shouts of uncontrollable lust coming from both of us as my lover emptied his spunk deep up my arse. It was SUCH a delicious experience, I knew then that I'd never forget my first time with a man.

We collapsed. Sated. I smiled at my lover and gently smeared my lips across his. "John, that was sensational!"

"It fucking was!"

John had to excuse himself, to go and pee after his exertions. I got up and began to dress again, realising that the new breast-form makeup had done its job superbly. There was still no trace of a join even after our sweaty exertions. I refilled my wine glass and lit a long cigarette, sitting on the sofa. My lover came down and kissed me yet again.

"John ..."

"Isla. That was sensational. I've never had sex like that - in my life!"

I glowed with pride. OK so it was my very first time, but I was so thrilled that John had been satisfied.

"John, you really...."

He interrupted me. I'd wanted so sit and discuss things, think about the role-plays we'd done before and maybe which one we could do - next time. And I was certain there was going to be a next time. But John wanted to have his say. He seemed to be in a hurry.

"Isla. I've got to go. Really. I'm so sorry to have to run so soon after this, I hope you won't think too badly of me but I have to get home, it's getting late, to see to the kids. But - Isla. I've just got to see you again. How about tomorrow?

I didn't understand the comment about kids but John's last comment distracted me. Tomorrow? Well - maybe. I knew Mary was still going to be away and so was Carol. We'd really just made arrangements for the one meeting, to see how things went. I wondered - for a moment - whether to suggest a 'meet' between Jenny and me. Me, in male mode, that is. But again John was ahead of me.

"We could go out for a drink, maybe, I'd just love to take you out."

Out? OUT?? That hadn't been anywhere in my plans. OK, so really I'd just love to, what tranny wouldn't. But I was still doubtful about whether I could 'pass'. Did John think I could?

"We could go to a pub I know, it's just off junction 8. They have an outside bar there. It's a bit dark there and very - er - romantic. At this time of year it's a very pleasant place to have a drink or two. Then maybe come back here again. How about it - you up for it?"

"John, I'd love to!"

Yet again I was going to say more. But John really was in a hurry. "I'll pick you up here - about eight. OK?"

"OK."

And he had to rush. And I had to relax. The previous couple of hours had been so delightful. I'd realised a life's ambition - and there was the chance of achieving yet another dream the next night.

Saturday - started out awfully. Now usually I liked Saturday mornings. Every week, my big workout, over half an hour's squash with my mate Will. But this time, in order to actually play, I had to 'undress'. Which meant using the awful-smelling solvent to take off the breast-forms, and going at my toenails with polish remover, and using the other even-worse-smelling solvent on my fingernails. And the most difficult thing, making absolutely sure that every single bit of make-up was removed. I had to do it Friday evening to be sure that all traces, all the bra pressure lines and thong lines and so on, had eased away in time.

And, distracted as I was, I really didn't play well. I dashed away afterwards claiming I had an urgent appointment, so that Will wouldn't notice that my body hair had been removed. I had a quick lunch and then started out on my preparations for my second excitement in two days. I'd picked the dress, of course. It just had to be my purple mini-dress. Not a micro this time. It is more stylish than that. And I just loved the colour, quite a deep reddish purple which allowed me to do all sorts of typically-tranny co-ordination with lipstick and nails and bag and eye-shadow. And a gorgeous necklet I'd only recently bought, a silver chain with a purple 'stone' in a very modern looking silver setting.

When I looked into the mirror - well - even I was impressed. I looked as good, as gorgeous and as sexy, as I'd ever looked even though I say so myself. John hadn't a chance. I'd won before we started. I was a little concerned though. John and I had always gone for the role-play thing online, and doing it the previous day had been such fun. Really he'd made a very good double-glazing salesman!

But since he was taking me out, I wondered if he had any other idea in mind for our 'evening out'. As if that wasn't an exciting enough idea. By the time I was ready it was already after half-seven, John would be here soon. He couldn't ring me of course, we'd never swapped phone numbers before out first meeting. Safety first, like they say. Maybe he'd emailed me. I rushed up to the study and logged on. Yes, there was an e-mail from him.

I opened it. I read it. I was puzzled.

'Hi Isla. John here, I'm so VERY SORRY about tonight. I'm not going to be able to make it.'

SHIT! I read on.

'Mary decided not to go away so our first meeting is going to have to be delayed. I promise you, this is not a lame excuse, it's real. As soon as I can I WILL write again, we really MUST meet somehow. Maybe even Isla and Jenny next time. Lots of love. John XXX'

It didn't make sense. Then I noticed the date. And the time. Yesterday. 3.00 pm. So if John had emailed me then ....

Then it clicked. He'd said something about having to go to 'see to the kids'. Plural. Kids. In all our previous conversations, our chats online, John had mentioned - several times - his son. Just his son. In fact, I remembered when we'd been chatting about something at some time in the past, he'd made a point of saying he only had the one son. And no daughters, I distinctly remembering him mentioning that, saying that he was glad he hadn't got a daughter so he wasn't tempted to wear her clothes because they would be too young for him. For Jenny, that is.

So John had sent the email the previous afternoon .... telling me that he wouldn't be able to make it .... because his wife hadn't actually gone away .... and he only had one son ..... unlike the guy who'd fucked me ..... so .... that guy wasn't John. Not 'my' John at least.

Suddenly, despite the two glasses of wine I'd had to calm myself down before John arrived, I was awake. Wide awake. I'd been fucked by a double-glazing salesman called John.

Two co-incidences. OK so John, a common enough name. A double-glazing salesman. Well, common enough. And - there was a third one, the fact that this double-glazing salesman, the one who wasn't the John I was expecting and who probably wasn't doing any sort of roleplay at all, had called on me at just about the same time as I'd been expecting - my John. Jenny, that is. But as John.

Hell. Coincidences apart, there were other factors here. John - my lover - was due in - I looked at the clock at the bottom corner of my screen - about five minutes. And even more importantly, he wasn't, or probably wasn't, a tranny or even a tranny-fancier. He was - or he probably had been - just an ordinary guy. And he'd fucked me. More than that, up until the moment I'd taken my thong off he hadn't known! He'd thought I was - a randy housewife seducing a double-glazing salesman. I'd passed. I'D PASSED!! I'D BLOODY PASSED!!!!

The doorbell rang.

John - that John - had arrived. To take me out. What the hell was I going to do? I could just sit tight, not answer the door. He'd either assume I was out, or didn't want to see him, and go. Probably.

I thought quickly. Very quickly. No contest really, there was only one thing any self-respecting transvestite could do. I went down the stairs, and opened my front door. John was there. He came in, and looked me over.

"Christ, Isla, you look even more gorgeous today."

I reached up and slung my arms round his neck to pull his body close to mine. I kissed him, passionately. VERY passionately. "Hi honey, good to see you. You want to go out - or fuck now?"

 

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