Two Way Stretch Ch. 01

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I sat on the bed next to him. Our thighs were adjacent, I slid my hand up his leg and could feel the swelling of his cock inside there. I kissed him again, lingering even longer this time, teasing his tongue with mine. Then I sat back a little and turned away from him.

"Richard, would you unzip me, please?"

I felt his hand hesitatingly move down as he did just that. I stood up to face him and slid the dress from my arms, allowing it to fall to the floor and stepping out from it.

"Now, darling, stand up, let me undress you."

It didn't take us long, I really did have some difficulty unfastening buttons with those long nails but very soon indeed Richard was standing before me wearing only his shorts. I really couldn't wait, I pulled them down and looked at, for the very first time, another man's erect penis. 'Richard' wasn't a big man. Okay he is tall but not enormously well built, a bit skinny really. I shouldn't have been surprised, hell, I really had very little to compare it with but his cock seemed to me to be about the right size, like him it wasn't very wide but it was long.

I lowered my mouth to the tip and teased it gently with my lips. There was just a smear of creamy fluid oozing out, I kissed it again, and then I took it right in my mouth. Richard groaned softly, and I sucked harder, taking time to stroke the head occasionally, then before returning to sliding the shaft deeper and deeper inside my mouth. His breathing got heavier, and then his whole body tensed.

"Oh my God!" he called out loudly.

His cock erupted inside my mouth, far more hot creamy liquid shooting into my mouth than I had imagined would be produced. I almost choked at first, then I swallowed and swallowed, loving the feel of the sticky cum sliding down my throat. He was writhing and bucking as he climaxed, he was obviously having a wonderful time, and so was I. Michael had been right! Being a woman -- like this --was exciting. It was fun!

But I knew there was more to come, I didn't want to stop there, I could feel my own cock straining inside my 'pussy' and hoped it was strong enough to hold me in. I moved up to look at Richard, smiling, satisfied, and kissed him again.

"Now for the main feature" I said, reaching my hand down and beginning to tease his balls with my nails.

I slid my nylon-covered thigh up and down his bare leg a few times, his cock reacted! He was very soon erect again, I could tell he was not at all sure about this, about 'performing' again so soon after cumming.

"Don't worry, my darling, it'll be all right, remember, I am here to give you pleasure, that's my job. Is that good for you, are you getting horny again? Richard, would you like to fondle my tits? I'd like that, and I'd really love you to fuck me."

I looked across. I had been in control. He was as my beck and call. Or at least he had been up to that moment. But something changed, something clicked inside him. He was the man, he was supposed to be the forceful one, I saw him change in front of my eyes. He raised himself up on his left arm and leaned over me, it was him taking the initiative this time.

Our lips touched, he backed off just a little and then he came to me, we touched lips again, his slightly parted lips pushed and he kissed me passionately and slid his hand over my bra top. His lips were soft and moist and warm, I wanted him to keep on kissing me. My lips opened, his tongue entered my mouth, I had the impression he wasn't used to French kissing but he learned quickly. Very quickly indeed. My arms reached around his neck and I caressed his shoulders. He pulled me tighter and our kiss became even more arduous as I submitted to his caress

As he moved on top of me I could feel his cock between us, I felt it grow once more as we embraced. I lay on my back, boobs jutting upwards, and lifted my legs into the air. Again I stroked my nylons along his body, this seemed to arouse him even more. I could feel his cock 'in place', our positions seemed to be just right, I was desperate not to give the game away in any way. I relaxed, he began to enter me very slowly, the angle of my false 'cunt' seemed to be very convincing. I remembered my own efforts with Michelle - I had absolutely no idea, it still seemed difficult to believe I had fucked Michael - three times!

I felt Richard's cock-head penetrate - that did cause me some discomfort, indeed some pain as he stretched me but there was more feeling inside my arse than I thought. I could feel the thickness of his cock inside me, it had definitely grown since I had last seen it! Then he wriggled - and slid deeper. THAT bit was heaven. He thrust in and out slowly for about two minutes, I could feel the excitement building in my 'cunt'. He gently and very slowly continued to slide in and out, the discomfort eased, it was a strange feeling but very comfortable, it all seemed just so natural. He just continued sliding in and out for several minutes as we kissed, he was cooing sweet nothings in my ear all the time.

"Ooh yes, Richard, honey!" I muttered as he continued.

And then he sped up in his thrusting, he was obviously building up to a climax. As he came I pushed my pelvis up and arched my back and groaned, I couldn't help it, and he slid just a little further in and touched something deep inside me, I bucked again and a massive cataclysmic shiver went through my entire body. I could feel his hot sperm gushing up inside me as he reached his orgasm. He was again calling out - and I was too, it was a mind-blowing experience, my very first as a woman and one I shall never forget. Having for several years done bits of the 'dressing-up thing' with Caroline and then with Monica, it was at that moment I became a real honest-to-goodness practicing bisexual.

After which, not surprisingly, we both collapsed. He slid out of me and lay there, beside me, my first male lover, breathing heavily but with an expression of pure delight on his face. I leaned over and kissed him gently on the lips, smiling.

"Richard, my darling, that was so good, really it was. You are a fantastic lover with a beautiful cock, I do so hope you will want to be with me again."

Whether I meant it or not at the time I don't know, but in a business sense it seemed the right thing to say. However it may have been a wasted advertisement, his eyes were already closed.

I slid out of the bed and pulled my panties up, then grabbed the long thin black negligee which was hanging beside the door and crept out and back into the bar. Without asking or seeking any other help I dashed behind the bar and got myself another drink, and again downed it in one. I sat there on the bar stool, satisfied. Sarah crept in and looked towards me.

"Well Raelene?"

There were a dozen questions in the way she said those two words but I think she could tell the answers to most of them by my expression, and by the only two words I used to reply.

"Fucking fantastic!"

6 - The purchase

Michael was right. After that experience, and another look through the accounts the next day with my solicitor I was convinced. Working there would be a dream, and financially I reckoned it could be a little gold-mine. I spent the next week going in and out, watching the team in action, looking and learning, and discussing with Sarah, the senior assistant, salaries and staffing and so on. I saw several clients in action including one pair of regulars. They didn't just 'dress' for their roles, they went all the way with costumes and make-up. It was rather strange watching Superman pick up Lois Lane in the bar and head for the bedroom. When I saw the guy in the red room earlier I would never have imagined he could look so good. Sarah did most of that changeover, she produced a great Lois Lane.

On the Friday afternoon all had been sorted, I was there finally to do the last bit of signing. Mr. Williams had all the stuff ready and at about 2 o'clock I became the proud owner of 'Two-way stretch'. Michael set off into town to drop the papers in at the bank and George stayed around to sort out his own papers during the afternoon. I settled in the control room to see what was going on. Then Elaine dashed in.

"I'm sorry, I've just had a call from no. 933. He has to go abroad on business unexpectedly, he's very sorry but he can't make it."

"Shit!" said Sarah when she heard, looking down at the booking sheet. "Okay, it's no good. Michael will have to do it. It's the busty blonde again, for Farmer John."

George explained that Farmer John wasn't really a farmer, well, maybe he was but he just looked like one. He was a regular, but one of the guys who came in every month or so to screw a blonde TV, the 'girl' of his dreams. And there was no shortage of transvestites willing to volunteer to book into the red room and do the job for him. But one had cancelled.

"But he'll have to wait, Michael isn't back yet."

"Sorry," butted in George "But I said he could go straight home, I thought you said we were going to do 933 on our own, Sarah. Now we haven't a 'woman' here at all for Farmer John."

Sarah looked at me. "Unless..."

I looked at her. Me? Well, why on earth not? I had enjoyed my previous incarnation as Raelene, could I do it again? Of course I could. My face must have given my enthusiasm away.

"I've checked Farmer John's record sheet, it does actually specify blonde or redhead, so you can do the whole Raelene act again. Okay? We won't have to redo the photo-sheet, that will save a little time but we had better get on. Mr. Wood - can you go into the red room and strip off? I can do this in about twenty minutes. Okay?"

It took nearer twenty-five but - though I say it myself - I made an even foxier 'Raelene' this time than I had before. Actually it was more down to Sarah then to me, she worked quickly but efficiently - the falsies above and below, the tight undies, red this time, the white 'body' top revealing my more-than-ample boobs, the tight scarlet leather micro-skirt, the fishnets and scarlet stilettos. And the make-up, more extreme this time, deep dark eyes and bright red kissable lips. I felt great, and again it must have showed.

I teetered into the control room to have a look just as 'Farmer John' was arriving. I almost backed out at that moment. I could see why he had been given that nickname. He was huge! About 6' 4" maybe, and big, very big, very well built and ruddy in complexion. Whatever his job actually was it was something outdoors, he was a very healthy specimen of manhood. I looked apprehensively at Sarah - could I cope?

"Don't worry, Raelene, he'll love you. I've made sure of that."

I bet she had. I saw Mr. Williams going into the bar with 'John' and showing him my photo-sheet. And I saw the look on his face. I really was still not sure I could live up to his expectations. However, in for a penny... I walked into the bar.

"Hi there, glad to see you. Gin and tonic, please, barman."

He was a regular customer, obviously, this 'John', within a minute he was sat on a stool right next to mine, his hand on my knee beginning to work its way up under my tiny skirt. I knew I had to slow him down just a little. I reached up behind his head and pulled him down towards me, kissing him hard, trying to begin to get into enjoying the moment. He kissed me back - hard - now I really was enjoying myself, this was really something. And then he picked me up!

With one hand round my back under my shoulders, the other behind my knees, he carried me through into the bedroom. He dropped me on the bed and before I could make any comment his shirt and pants were off. I gasped - his cock was erect already, and it was big, much bigger than any I had seen in my own limited experience.

"Wow, my darling, that looks good. Can I have a taste?"

And this time before he could surprise me I was leaning over him on the bed, opened my lips round it, and slid my mouth down onto that enormous cock. Seriously, it wouldn't fit, I reckon I got just over half of it in before it jammed into the back of my throat. Anyway I resisted, gave him a bit of a suck but I wanted to get on with it. I moved off him, lay back and opened my legs.

In all my experience since then I have never had such a cock shoved up me, never felt so full, so ecstatically aroused as a man slid back and forth up me, and never been filled so much as he shot his load deep up me. I was shaking as he climaxed, I didn't need to fake anything, it was glorious. I think Sarah knew it too. By the time I had finished in the bathroom, John had gone. I emerged from the bedroom to find Sarah waiting. I strode past her and behind the bar, after all in a few minutes I would own it - and got myself a drink.

"Well, Mr. Wood, or rather Raelene, if you can cope with John's organ you can cope with anything!"

Too right!

"You didn't tell me, his cock is enormous!"

"And, go on, what was it like?"

"Fucking brilliant!"

Sarah grinned at my unintended double-entendre.

"Michael was right, you really are a natural at this, Raelene. I can see we're going to have some fun in the months to come."

Suddenly the door signal went - I must have seemed rather worried. Sarah got up to get it, calling back as she left.

"Don't worry, that's my girlfriend Debbie. I'm off now, are you and George going to lock up? I've got the back-up computer tape, see you Monday."

At which, to my surprise she gave me a quick peck on the cheek, really a very girly action. I saw her open the door and again quickly kiss the girl waiting just outside the door. Girlfriend? I had never realised.

I had really had enough surprises for that day but it hadn't finished yet. George Williams came in from the control room, holding out a package towards me.

"You'd better have this, we always do two backups for the computer data every Friday, just in case of a fire over the weekend or something. So that's it then, in some ways I'll be sorry to see the last of this place but I really am sure it's in good hands. Elaine's gone already, she was desperate to get home and start packing. How about a last drink - sorry, I forgot, you have to change!"

Too true, I could hardly go home in fishnets and a negligee, and 6" high heels. I suggested a final drink to George, after all I was paying for it. We chatted for a few minutes, George wouldn't have another, he was due to be driving home. Me? I was still catching a bus to and fro.

"Just one thing, George, how did you get into this? I mean this business, it's a bit of a strange set-up isn't it?"

"Funny really, my dear." he started to say, then we both realised it was in a sense 'Raelene' he was talking with, maybe it was easier, I don't know, discussing it with a woman. I smiled and put my hand on his.

"About twelve years ago, Elaine and I were having a bad time. She had just started to get ill, not seriously then but it affected our - sex life, you know. We just couldn't get it together. Still, we were very happy in other ways, always have been. We went out with a friend of hers from where she was working, just for a drink. Ended up with the three of us in a bar somewhere getting a bit drunk, feeling sorry for ourselves. Anyway this gorgeous brunette was there, asked me for a light, we got chatting, the four of us. Then Elaine asked her friend to drive her home, gave me a look as she suggested it, to say 'go on, go for it, have a good time for once'."

He began stroking my hand as he was talking, obviously relieved to get it off his chest.

"We went back to her flat, she was really a very sexy-looking woman. She went straight into the bedroom when I got there, came out wearing a thin baby doll nightie and panties, nothing else. I was really turned on, we started making out, and as I fondled her boobs and got inside her panties - you can guess, can't you?"

I had to smile, and couldn't really think what to say, but he continued.

"That night I fucked him - her - twice, it was a revelation. I realised that some guys make better women than women. And maybe there are more than people think."

I looked him in the eyes, he was feeling sad at the recollection but I could tell he was relieved to get it off his chest.

"Did you tell Elaine?" I just had to ask.

"Oh yes, sure, everything. He, or rather she, was one of my first assistants and damn good too. I've been lucky there, lots of good people working with me. Like Michael and Sarah, and the two part-timers, they are all people you can trust. They'll serve you well, Raelene."

And it was that final name which did it, as he looked straight at me and called me that, I just had to kiss him. Not aggressively like John or my bank manager, but as tenderly as I could I leaned across and slowly teased his lips with mine. I slid a hand inside his shirt, feeling his hairy chest, sliding my long-nailed fingers down towards his waist, gently beginning to probe inside his pants. I smiled as I detected his reaction.

"Look George, this is the last farewell in a sense, you and Elaine off for a new life together. If you would like one final fling... I would be honoured if you would fuck me."

He did, and we did, that final time for him, the end of part of his life but the start of a very different part of mine. It was a fitting start, getting screwed by the 'ex-boss'. As he climaxed inside me on the bed I hoped he would be doing the same to Elaine for years to come.

"Christ Raelene, thanks for that. I've never had a guy since that one time and to be honest I'm not really sure I have now. That was good, really good. Like I said I know the business is in good hands. I think it's all sorted, you just need to get another assistant, with you coming in for Elaine and me, you need another woman to help out."

I sat on the edge of the bed and crossed my legs, showing him acres of thigh, and leaned over to give him a final gentle kiss, and of course to show off my tits.

"Or another man!" I joked.

So it's all go from Monday, the three of us and Carol, the student part-timer who is coming in full time for a few weeks until we find a replacement for Elaine. George had a good send-off, I am pleased I was able to do that for him. I wonder if he will tell Elaine he fucked me?

I hope the clients keep coming in. Maybe we should advertise. Not in the papers of course but where? On the Internet? Possibly. Maybe by putting something in the sort of place potential clients might look? Like one of those sites for tranny stories? Maybe they could send me an email?

So how about it? Do let me know? How can 'Two-Way-Stretch' best serve you? What would you REALLY like to do? And with whom? Or to whom? I am sure we can accommodate you, we are booked up for a while ahead but I am sure I can fit you in - somehow. Let me know.

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5 Comments
AnonymousAnonymousover 12 years ago
GREAT story!

VERY immaginative! You are one great writer!

Marcie

AnonymousAnonymousover 12 years ago
great read

I found myself not wanting it to finish. Great read! As a real Gurl myself, I remember those first steps years ago.....

AnonymousAnonymousover 12 years ago
WOW ! WHERE DO I SIGN UP ?

SIMPLY ONE HOT , SEXY STORY - wish I could land THAT JOB !

AnonymousAnonymousover 12 years ago
WOW!

that was one of the best by far....Keep up the great work

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