Crossdressing a Life - Sex Stories

Crossdressing a Life

... and lee fully dressed, the wife was sat in her usual chair. After a short time, Lee took me to the spare room, this time he stayed and watched me change, he loved it when I dropped my jeans to reveal panties and hold up stockings, once I had changed, we kissed then climbed on the bed. We kissed and stroked each other, and Lee's wife came in and started to caress us both, she massaged my bottom then started to finger me. As I kissed Lee his wife was fingering my boy pussy, she then started to insert a ten-inch dildo into me, as we played his wife fucked me until I had a lovely orgasm.

Once the dildo was removed Lee asked me to fuck him, I stroked his bottom then fingered his pussy until he was ready for my cock, I entered him slowly and then fucked him until he came. We lay together and it was only then I realised his wife was still in the room and had watched the whole thing.

After I changed back to male mode we chatted over a cuppa as if what had just happed was nothing unusual.

My next meet was another car meet, will I ever learn? This time it was properly planned.

I met Alana on a deserted road in the middle of nowhere, I climbed in her car, and we chatted then kissed and cuddled, the suck each other's cocks, whilst Alana sucked me, she fingered my bottom which turned us both on.

Just before I left Wales, I was fortunate to have a meet with Gina. I met her at her lovely home where once I was changed, we got to know each other, lots of kissing and caressing ...

... and cock sucking, then Gina fucked me with a long dildo, we had a wonderful night together I just wish I had met her sooner.

After I moved back to the north of England, I tried to give up on meeting crossdressers, so I started to look for a lady escort would meet my needs. I found a lady who was in her late fifties and gave massages. We discussed at length my interests and I settle on a massage with prostate massage too.

When I arrived at Jean's house I was shown upstairs and once I had carried out the paperwork I stripped and lay on the table on my back with my rock-hard cock pointing up.

Jean stripped down to just a pair of hold up stocking and panties and proceeded to massage me from head to toe, talking to me the whole time, I caressed her legs and bum. Then Jean massaged my prostate and wanked my cock until I came shooting sperm up into the air.

I continued looking at all the crossdresser and swinging sites and eventually was contacted by an older gentleman in Newcastle, I cannot remember his name, but he had lots of sexy pictures of him entertaining various crossdressers. We chatted for a bit then agreed to meet. He lived in a tower block of flats in the middle of town. I arrived on time, and he buzzed me in, we chatted some, then he showed me to his spare room and allowed me to change. I dressed in seamed black stockings, high heeled shoes a knee length skirt and blouse. When I walked into the living room, he was completely naked and stood next to the sofa. ...