First Time With Another Crossdresser

by Stephen T (Bristol)

I have been dressing since I was 14 but never indulged with another guy. One day I was looking at transliving and I came across an ad with a fairly inexperienced crossdresser that was around my age and wanted to get to know another one.

He lived around London and I work there a lot or roundabout so I noted his number and gave him a call it was a very sexy call and he sounded very gentle so we arranged to meet in a Plaza hotel. I was very nervous and being fifty-five had never done anything like this before and have always been worried about Aids and passing it to my wife of 20 years.

We met in a park local in our normal dress and said hello it was very near to where I was working and I gave him the swipe card for the room and we agreed he could go ahead and prepare himself for the meet.

I had to work so he had a couple of hours to ready himself but I had to wait until later to shower and ready myself. I was trembling inside all afternoon and could fell my cock twitching.

I went into the room and sure enough he was just like the picture in the ad and he looked pretty good I walked up to him and kissed him full on his lips which were in red lipstick I slid my hand over his stockings up under his dress and smoothed his cock in his silky panties. I was really hot under the collar and amazed I was so ready for this.

I dropped to my knees put my head up under his flouncy skirt pulled out his cock and put it in my mouth and was amazed how good it felt as it grew and grew until he was very hard. I said sorry but I had to stop to shower and dress, he had brought a wig and high heels as I did not have any with me just my lingerie., so he sat down opened a bottle of wine and relaxed. I readied myself and he said use his douche to make sure I was clean everywhere so I did, I had never done that before.

I came out with all white lingerie big silky soft grannie panties which I love, stockings bra and suspenders and full nylon slip all made up with his wig and shoes, I had on a flouncy summer skirt and white blouse so you could see my underwear through it and my hair tied up in a silky scarf in a turban.

He Said good you look sexy and I went back to sucking his lovely cock I loved the smell and taste and he had lots of slippery precum which I rubbed all over my face in my eyes and everywhere I could I was lost in his big cock.

He stroked my cock which was straining my big panties and he said I can't believe this is your first time as you are so sensual, I fell back on the bed with my head over the edge of the bed .

I said I have dreamt of doing this for years to be dressed like this have my head back over the bed with a lovely cock in my mouth all the way in until the testicles keep banging my nose and face.

We got into the 69 position and enjoyed a fabulous time sucking each other and he came in my mouth the first time I have ever done that I thought it was fabulous to taste and swallow his lovely come.

He said you have a lovely big cock and hoped that is what I had he asked I f I would fuck him I said I have never done it before so we shall try. I said I wanted to use a condom but he looked saddened so I ok we will do without.

He bent over with his stockinged butt in the air I lubed my cock and inserted the head of my cock in his lubed hole he had cleaned and used a butt plug while I was getting ready so I slipped in with ease and slowly thrust in and out god it was heaven.

We fucked for a long time and he said god you must be aching to come and I said yes. We stopped and he got on his knees and sucked and wanked me in his mouth until I came loads in his mouth.

My god he said I have really struck lucky with you as you are so sexual even though you are inexperienced, he said he had done it a couple of times but right from the start when you first saw me then kissed me he said no one had done that and he knew this was going to be right.

So we struck up a great relationship dressing, sucking and fucking whenever we could. We are both getting older but still love the feel of silky undies, scarves, Full sheer nightie sand both love big silky knickers and wanking each other in them. He says he loves me and wants my babies but I don't think that will be happening as it not possible.