Crossdressing a Life - Sex Stories

Crossdressing a Life

... Edinburgh, she shared lots of sexy pictures of her visits, which were quite explicit. After seeing these pictures, I assumed Pauline was out of my league.

I was very excited when Pauline agreed to meet me, I could not wait to visit her home. On the day of my visit, I showered and dressed in sexy underwear then but on my male clothes. I drove to Pauline's at the agreed time.

Pauline lived in a small block of flats, on the ground floor, she buzzed me in the main door and had just her head around her front door, she was fully made up but without a wig. Pauline welcomed me into her bedsit and offered me a drink, we chatted and as we talked Pauline put her short blonde wig on and I got to look at her properly. Pauline was dressed very eloquently in seamed stockings, black court shoes a mini skirt and a nylon frilly blouse. I told her she looked stunning.

I stripped out of my male clothes right in front of her, she could not keep her hands of me.

I dressed in a mini skirt and white blouse, red strappy high heels, and a cheap blonde wig.

We sat together on her bed settee, and we kissed and caressed each other, Pauline stood up, lifted her skirt, and lowered her panties, I went straight to work sucking her cock. Then Pauline knelt between my legs and started to suck my cock.

At Pauline's suggestion we pulled out the bed settee and lay together on the bed, after more kissing and caressing, and lots of nipple play Pauline got on all fours and asked me to fuck ...

... her.

I knelt behind this glamourous elegant lady and began to slide my cock into her bottom, her bum was quite tight and felt wonderful on my stiff cock. I fucked Pauline for what seamed like hours, she squirmed and moaned the whole time, then she had a huge orgasm and came in her panties. Pauline then sucked my cock until I came in her mouth, she then licked her lips and greedily swallowed my come. We kissed and I tasted myself on her lips. We then chatted some more as we calmed down. After I changed Pauline swapped her high heels for some fluffy pink slippers and I was shown to the outer building door with Pauline still fully dressed and made up, if a little bit dishevelled.

My third meet was with Kirsty, this gurl lived in Bedford and was able to accommodate. I arrived at her door to be greeted by a 65-year-old gurl partially made up, she had on shirt and trousers, but was wearing heels and full make up. Once inside I was shown to the spare room and allowed to change, when I walked in the living room Kirsty was fully made up and gently began to seduce me. Kirsty was a widower, who explained that when her wife was alive, they would frequent swinging clubs and she would get a kick out of watching men fuck her wife and she would clean them both up afterwards.

Kirsty was into bondage and discipline; she had the most amazing nipples which where large from many years of using nipple clamps. I would bite them quite hard which turned her on so much. I met Kirsty two or three ...