Crossdressing a Life - Sex Stories

Crossdressing a Life

... fucked by this tall handsome man and totally loving it.

We had a break so I could kneel and suck Sir's cock, which I greedily did.

In his spare room Master had a dungeon, they was an umbrella stand full of canes and crops. In the middle of the room facing a floor length mirror stood a kneeling horse which had some heavy-duty chrome chains on it. I knelt on the horse and was chained securely in place. Then master gave me six of the best with a chain then he entered me again and rode me. My knees started to hurt, so Master led me to another room which had a double bed in it and looked totally ordinary. The Bed cover was hiding more chrome heavy chains which were attached to the bed corners. Two pillows were placed in the middle of the bed and Master proceeded to chain me to the four bed corners. He lay on top of me and entered me again, he made love to me slowly at first, then he started to grunt as he sped up. I was moaning so much he had to stop and ask if I was ok. I was nearly crying as I told him to carry on, Master fucked me until I came onto the top pillow, it was some of the best sex ever.

My last meet in Swindon was with a crossdresser called Sam. She was in her sixties, quite tall but very elegant and sexy. We met at her home. Sam was married but her wife worked nights so Sam would dress for hours on end. I changed into a sexy outfit, and we had a mutual wanking and blow job session. Sam was a very generous lover who gave my sensitive nipples lots of ...

... attention. She told me I had great skin for a man, lovely and soft and said she would love to fuck me. I told her next time. Unfortunately, I moved away soon after our meet.

After I moved home I kind of stopped meeting, as opportunities became a bit difficult.

I did have one meet with a professional Mistress who was so sexy.

Mistress entertained me in her place of business. She met me at the door she was dressed in a low-cut black dress, hold up fish net stockings and high heels, she looked stunning, and I told her so. I was given a quick tour of her premises and was offered a shower, I undressed with Mistress watching me, which I enjoyed. I then showered.

Once back with Mistress I dressed in hold up stockings and panties. We chatted some more, then I was shown into Mistresses playroom. I was given a pair of high heels wear and then instructed to kneel on Mistress's kneeling stool. I was strapped down and teased, spanked, and paddled, all done with lots of discussion on my pain threshold and lots of touches and caresses. Mistress placed two of her fingers in her pussy then placed them Infront of me so I could lick them and taste her sweet pussy.

After I was released, it was Mistresses turn for pleasure, she lay on her bench and instructed me to lick her pussy, Mistress had a sweet tasting pussy which became wet very quickly.

I then swapped places with Mistress and played with my cock whilst Mistress walked up and down talking to me, she then sat on my face, and I ...