28 Sep 2019

Please see End Of The Road 3 (10/09/19) to get the gist.

The job went on, with Tom and myself acting like nothing ever happened. He continued to make me tea, I continued to do the work. After the one day when it pissed down, the weather had been fine, so no reason to sit in his house with nothing to do.

End of the job all that was left was a day or so of making good to the small areas of disturbed plaster work etc. inside the property. That would be me finished, as other contractors would do decorating etc.

Next morning I set up, dust sheets, steps etc. and get on with the work. Tom makes tea now and then and I still stare at his hanging cock under his trousers.

Around 1pm I have done all prep work and applied first coats of render, plaster, which had to set.

Nothing to do now until plaster has set, so I should call it a day. But I decide to tell him I’ll be back after an hour for lunch, he must have thought it a bit odd, as I normally just ate my sandwiches on site.

I drive around for an hour, thinking of a way to have another session with old Tom, then head back.

I knock and wait. The door is answered by an older woman, slim, dark hair, white blouse, black skirt, stockings or tights and heels, her face is turned away from me, as if she’s listening to someone else. She waves me in and I squeeze carefully past her and into the hall. For a few seconds I’m wondering who this is, as I know Tom’s wife had passed away some time ago.

I look at the woman and it’s not...It’s Tom...Make up, the lot.

This was the early eighties and, although I knew there were men who dressed, I had never seen it in the flesh, and the odd photo I had seen was of men who looked like men, with women's clothes on.

I couldn’t stop looking, he looked great. I suppose his slight build helped. I remember wondering what padding he had used for tits. They looked small, but real inside the blouse and bra. You could still recognise his face, except it looked softer and maybe 10 years younger

He indicated for me to go into the living room and sit on the sofa. He walked over to the old sideboard, pulled out a bottle of whisky and poured two drinks, passed one to me and stood in front of me sipping his drink. His legs looked perfect in the stockings (I had seen the tops of them when he bent down to get the drink) and he walked like a woman. I wondered where his big cock was, there was no bulge in front of the skirt.

Sitting next to me, he smiled, gently took my hand and placed it just above his knee. I was shaking, nervous and excited. I could feel the silkiness of the stockings as I started to run my hand up and down his thigh. I could see the lacy top of the stockings as the skirt road up with my hand.

We both set our drinks down (mine was gone haha) and he moved closer so his leg was touching mine. I stupidly said ‘You’ll get dust on your skirt from my jeans’, he smiled again.

‘It’ll wash’ he whispered.

Not one word had been said until then.

Taking my face in both hands he leant in and kissed me. Soft, gentle kisses. I responded, pulling him towards me and kissing more urgently, my tongue pushing between his lips, my cock straining inside the jeans. My mind accepting this was an attractive woman, mature, sexy, slim and petite, albeit with a huge cock somewhere down there!

He stood, holding out his hand and led me upstairs, I was behind and watching his slim bum wiggle and those sexy legs…

In his old fashioned bedroom we stood close. He was a fraction taller than me with his heels on, but not enough to make it awkward. He pulled at my T-shirt and I whipped it off. He ran his hands over my shoulders, chest and stomach. I was very fit in those days, with a very athletic to muscled build.

He got to my jeans and slowly undid them, sliding them down, along with my boxers, gradually kneeling to push them to the floor.

My cock was brushing against his hair (wig) and he took it in his hand, sighed and proceeded to suck, lick, wank my cock and suck my balls. He was an expert, as good as any woman. I have a good sized cock, looked even bigger when I was a slim young man, but he took it in easily, gagging a little now and then, which turned us both on even more.

I couldn’t take much more so gently raised him up, stood back and hurriedly completed the fiasco of removing trainers, socks, jeans and pants, nearly falling in the process. He laughed and this strangely broke the tension, but not the sexiness of the situation.

I move close and run my hands over the blouse, feeling his tits. I know they are fake, but they don’t feel it, can even feel nipples!!

Hands moving down, I slide the skirt up to his waist. Feel the tops of his legs, very smooth, feel the lace stocking tops, run my hands around to his small bum, through the suspender straps and over a pair of old fashioned full knickers, which seem slightly at odds with the delicate stockings and suspenders. Ran my hands back to the front, across the pubic area, confused as to where his cock was.

He took my hands and set them around his slim waist and looked me in the eye.

I started to undo the buttons of his blouse, but fumbled, cos I was still shaking with excitement.

He took over, quickly removing the blouse. I looked at his slight body and at the bra, which was the smooth, slightly see through type (I think they were called gossamer) that were popular at the time.

Tits, proper small tits, with hard nipples stared back at me!! They were not like the ordinary male fat that some older men have, he was too slim for that. I thought it may be that his chest muscles had gone soft? I just didn’t know. He unclipped the bra, removed it in one movement and there they were….. Real tits, small but a perfect tear drop shape. I touched and fondled them, they were soft and supple, not at all like the silicone implants of the time.

At our previous encounter he only dropped his trousers and wore baggy jumpers, so hiding these assets.

I didn’t know how he had those tits and I didn’t ask, I just looked at them, touched, fondled and kissed them. Sucked his nipples, which hardened. Then we kissed, he turned me and gently pushed my shoulders ‘til I was sitting on the edge of the bed.

Standing close, he slightly parted his legs and I eased the knickers down. As I did so his cock came down from between his legs...so that’s where it was. Cock and balls now hanging down, I remember thinking it must have been half way up the crack of his arse.

Looking at this huge hanging cock, dangling balls between his slim legs and hips, then looking up at those lovely small tits, I reached and took a tit, the other hand wrapping round his cock….and I shot my load, all over his stockings. I hadn’t touched my cock.

It was intense, went right through my body, but my cock stayed firm and hard.

I wanked and sucked his cock ‘til it grew as big as I remembered, then we gradually eased our way onto the bed. Kissing, touching, God it was so good.

Eventually, he guide me so I was laying on my back, then he straddled me, his cock resting along my face. I took it and put what I could in my mouth. Then he moved down, took my cock and placed it at his bum hole, or pussy, as he called it in a whisper.

I entered him easily, he had obviously lubed it well, though I didn’t see him.

We fucked like this for some time. I alternated between playing with his tits and his giant cock. He leant forward sometimes so I could suck and bite his nipples.

Then I started to buck up towards him, and then I was cumming, we were both moaning, he started to wank his own cock quickly and urgently.

I pulled at his legs, moving him up to my face, one hand on his cock I started to suck him. He stiffened and exploded into my mouth, spurt after spurt. I tried to swallow but couldn’t cope with it all. I had never had anyone spunk in my mouth before, but then I had never done most of these things before.

He collapsed onto me and we lay there cuddling, short of breath. We had hardly said a word.

After a while he asked me to go downstairs and he would join me shortly.

I took my clothes, went down, dressed and sat on the sofa, exhausted.

He came down, wig gone, make up off, normal clothes on.

He told me he wouldn’t be in tomorrow (my last day) and he gave me a key and said to put it through the letter box when I’d done.

I asked him when I could see him again, but he shook his head.

‘You’re a very sexy young man’ he said.

‘You have a lot of adventures in front of you, with both women and men. I was just one of them.’

He thanked me for all the work, said he would tell the Landlord what a good job I’d done and said goodbye.

I never saw him again. He was right, of course, but, at the time, I felt quite sad.

Sorry this one was so long, but I couldn’t see a way to shorten it, without dumming down how sexy it was to me.

Next, back to the future