I was Introduced to Crossdressing

by Stephen T (Bristol)

I was at college and need some spare cash and I got chatting to a guy I knew from the pub I said I need a weekend job to earn some money to make life easier whilst at college. He said He could do with a little help and offered me an opportunity.

I went along on the Saturday morning and he showed me what he needed done and he was very nice and there were plenty of things to do.

As we went about the various chores he walked past me and touched me up, I laughed and took no notice as that has happened before just messing and he did it a couple of more times I still took no notice.

When we finished he said he will need to go to the cash point and to come back later so he can pay me so I went home showered and then walked back as it wasn't far and it was a beautiful summers evening.

I knocked on his caravan door and he opened and said come in I was shocked at how clean and nice it was in there as he was a 45yrs old man living alone. The first thing I noticed was some freshly ironed sparkling white underwear of his.

He said sit down and asked me if I would like a drink of cider so I accepted I noticed a pile of glossy soft porn mags which he caught me peering at he laughed and said you can have a look if you like so I did.

I was engrossed as they were top notch mags and I started to fidget a bit as I was trying to get comfortable as I had a raging erection, he smiled and said having trouble and he also started looking at them. He lifted off the top 3 mags and down the pile he pulled out a mag it was porn and he showed me it and the rest were all porn.

He stood up and I noticed he had a huge bulge in his trousers and smiled he said I have got your problem as well and stroked the massive bulge. He said you can stroke yours if you like nobody will come so it is safe and then he unzipped his trouser and out sprang a beautiful huge cock with a really big head.

It shook me a bit then I felt a funny feeling in my stomach as I realized it was having an effect on me as nobody had ever done this around me before. He said go on take yours out so I did he said that is not a bad size either and sat down on the couch beside me and started to wank it slowly he said go on you can do it as well so I did while looking at the books.

He said we may as well get more comfortable and said it will be better if we took out clothes of and said this sofa will drop down so he did it. Lost in the moment I disrobed he then took hold of my cock and started to wank it slowly.

He then and took hold of my hand and placed it around his huge cock, god was I getting excited by the site and feel of this lovely slippery huge cock as I had never done it before.

He then slipped of the sofa bed to his knees and slipped my cock into his mouth and started to suck me wow was that good another first I got carried away then reached for his lovely cock fell to the side and took that gorgeous cock in my mouth we then got in a 69 position and I sucked for all I was worth.

I came and he swallowed it all, he said he was going to come and it will be a lot as he had not come for a while. I had never done this before so it was new to me then suddenly he came spurt after spurt into my mouth, god it was so much and I gobbled and savored every drop , I loved it and was lost in his cock.

After we had finished I was still rock hard and carried on looking at the mags and there was one where all the guys were sucking their own cocks that got me going more he said have you never done that I said no never thought of it. He said you should be able to do it easily so he helped me raise my legs over my head and guided my cock into my mouth and with help got half way in it was amazing.

He held me there and he also became erect again and I really wanted that lovely gleaming slippery monster up me and watched as he guided his cock to my butt hole squirted a little KY on it and slowly pushed it in. It hurt a bit at first but slowly it became an amazing feeling as he fucked me for ages until I came again in my mouth and he came in me. Wow that was a first and absolutely amazing.

I knew I wanted more of him we carried on looking at his mags and there was one where the guys were dressed in female lingerie stockings, suspenders, big grannie panties camisoles and nighties and some had their hair tied up with silky scarves, my cock sprang into life again and he said wow that had a big effect you obviously are turned on by that and I admitted I was very.

He said would you like to do that I nodded he said ok if you like next weekend I will see what I can do. I went home in rapture at what had just taken place and could not get it out of my mind all week. I returned on the Saturday we did some work and then I showered at his.

He called me into his bedroom and there was a bag on the bed from M&S stores open it he said and in there was all this lingerie all in my size I could not believe it.

Slowly he dressed me in this lovely lingerie and slid the stockings on me and attached the suspenders then slid the lovely big silky knickers up over my stocking legs my cock was pulsing bobbing up and down in front and every few seconds he slipped it in his mouth then pulled the diaphonous knickers up over my pulsing cock.

He then tied my long wavy hair up in a silky scarf turban. He opened another bag and there was red lipstick and told me to purse my lips and applied the lipstick. He then opened a box and pulled out a pair of high heeled black shoes and put them on me.

He had all the right sizes he said come have a look in the mirror I did and I was flabbergasted at how feminine and sexy I looked, I turned around and he was stood unclothed and he had hidden full lingerie under his clothes also so it was obvious this was his thing he had a wig also.

We laid on the sofa bed and he kissed me then slid down under the silky sheer nightie I was wearing and pulled my cock out and sucked me wonderfully I got into the 69 position and could not wait o suck his beauty again.

It was a wonderful feeling of abandonment writhing there on the bed all that fabulous silky slithering and swishing of the soft nylon and the feel of stockings rubbing against each others.

He then laid on his back and I took hold of his slippery great cock and with the help of KY slowly impaled myself on his cock until I was able to take it all then I bounced up and down on it for all I was worth all the time he was wanking me until I shot all over him and he then came loads in me.

We did this every weekend until I finished college and had to get a job and then every now and then when we could. He introduced me to something that I will always want especially a lovely huge slippery cock.