Written by Wolfman54
04 Mar 2016
My First Time with a Crossdresser
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8 minute read
Now you have to remember that this was 35 years ago when the world was different in many ways, Gay was kept a secret as was the subject of cross-dressing.
. I was only 21 and away on training for the company i worked for. I drove down to just outside London on the Sunday afternoon where the training was to take place. It was not far from where i stayed and in those days the traffic was not what it is now.
I booked into the small hotel and started to look for a pub that had some life in it. I soon found what i was looking for, a place tucked away down a back ally with just a small neon light outside. As soon as i open the door the music hit me, so loud that i could feel the base pumping in my chest. I went over to the bar and ordered a beer, sat down and looked around the room to see if there was any spare pussy around. Nothing came to mind so i just sat and enjoyed my beer.
With the music so load you can only stand it for a short while and so i went outside into the pubs back garden and sat among the trees. After about 5 minuets a young girl of about 19 came out and started to have a smoke. We looked at each other and acknowledged each other with a nod. On one else came out so we started talking about the normal things two strangers talk about, do you live here?, what are you doing here?, the normal. I ordered some more drinks from a barman that popped his head out of the door and carried on with our conversation. Her name was Susan and we talked for about three hours, with more drinks the conversation got round to sex as it always does. She asked me what turned me on, and i told her that a woman's body was a beautiful thing to see. But it should be dressed to feel sexy as well. She asked me what i meant, so i said that a woman dressed up in stockings and suspenders with silky panties and heels just did it for me. The feel of nylon and silk on a body felt so soft and sexy. She laughed and said. You would just love my flat mate, she wears all of those things every day. I couldn't stop asking questions about her flat mate and my new friend was just laughing at me.
Then she stopped and said, would you like to meet her? For sure was my answer. So she said just wait a minute and i will call her to see if she is in.
So off she went to the Phone Box. As i said it was back then when Cell phones had not been heard of. She came back and said i was in luck. We walked for about 15 minuets till we came to a block of flats. We went in and climbed up to the third floor. She open the door and invited me in. It was a normal students place, with posters and personal things lying around the place. We walked into the lounge and she said, sit down and i will make a cup of tea. I sat there by myself for a while and then i heard a noise from behind me of a person walking into the room.
I stood and turned around to see this beautiful blond girl walking towards me with her hand out to shake mine.
You must be John, the boy Susan told me about, i am Tracy. We shook hands and i could hear the heavy silk of her yellow blouse rubbing together. She sat down next to me and straight away i could see as her tight fitting black nylon skirt rode up that she was wearing stockings and suspenders.
My hart was beating 20 to the dozen and i decided to be forward and placed my fingers on the top of her leg and ran them over the suspender strap clasp. i said, i love what you are wearing, very sexy. She smiled and said i love a man who appreciates what a girl wears. She seemed so calm and asked me if would like to feel the quality of her cloths, i ran my hands all over her blouse skirt and nylon clad legs. as i touched her legs she opened them just a short way to allow me to run my hand under her skirt and feel the suspender straps.
She laughed and stood up. Take your cloths off was all she said. So i did...as quick as i could. She sat me down and knelt between my legs and took hold of my cock that was standing like a pole, she stroked it up and down with such tender strokes i nearly came there and then. She was smiling and just lent forward and took my head into her mouth and started to run her tongue around soon she was moving up and down taking more and more of me into her mouth. I have a good 16cm but she took the whole thing till her lips were on my balls. She came off and asked, do you like that? wow that feels fantastic i said. Again she smiled and stood up, undid the hem of her skirt and let it drop to the floor. What a sight, Black stockings, suspenders and the most shinning silky pair of full panties i have ever seen.
She knelt down facing the empty seat and asked me to go to the side dresser and get some lube from the top draw i stood and did as she asked. Whilst i had fetched the lube she had pulled down her panties to just below her beautiful ass cheeks. She said, you can fuck my ass but no more. I wasn't going to argue with her and opened to top of the lube and applied it to the top of my cock. She said, i am going to keep my legs closed so that it will be tighter for you. At that i knelt behind her with my knees on either side of her legs. i started very slow and worked my way in bit by bit. She was moaning and telling me the speed i should go as well as when to go deep and when to hold it still. I must admit i nearly came a few times but held back. I was in heaven, feeling the silky nylon of her suspenders and blouse and my balls rubbing against the material of her panties, i didn't want to go anywhere.
She said that if i wanted to come it was OK, she knew how i was feeling. At this command i let go... the most intense cum of my life up to then. Whilst i was in a dream world letting my cum just fade away i heard her say. You have had your fun, now its time for you to do the same for me. Whilst still leaning over the couch cushion she picked up my shorts and wiped herself clean. Sit down she said, to witch i did. She looked up at me and said, have you ever been with a man before? to which i said no, never. she smiled and asked if i had enjoyed my cum in her ass. Fantastic was all i could say. Great she said, close your eyes and do not open them till i tell you to. So i closed my eyes and waited for a few seconds, then i felt her straddle me with a knee on each side of my legs. Then she said, i want you to open your eyes and do not say a word. As i opened my eyes there before me was a 9 inch standing cock...bigger that mine. Where...i began to say, but did not get any further. Then it came to me, as i went to get the lube she slid her panties down and hid that cock in front between her legs and the couch.
Don't be scared she said it wont bite you. Hold it in your hand as if it were your own and think of it as an extension of your own cock. I took it in hand and started to stroke it up and down. I must say it did feel nice. After a while i could see the love juice starting to cover the head. Still she did not say a word. It was as if she was letting me discover a new experience. like i child learning to build a puzzle. You know what to do she said in a low soft voice, and as if had done this a thousand times i took her into my mouth and tasted for the first time the cock of a man.. She rolled over back onto the couch and with her legs open invited me to continue to pleasure her. I did for a long time.
After a while i could tell she was going to cum so i pulled back, just in time before rope after rope of white hot cum exploded onto my face. No.. i didn't lick it off, or swallow any of it. i just picked up the same shorts and wiped my face.
We looked at each other and smiled and laughed again.
Just then Susan walked in and said, by the look of you two you both enjoyed yourselves. We did i said, you should have been here to watch us.... a couple of pros. Ho i did see she said...I was filming it from the next room.
So some where in Porno land there is a film of me giving my first head to a man. And it wasn't the last.