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tonytnt
Gender: Male
Activity: 295 points
Last Login: 1 year ago
7 ratings

My First Time In Heels & Pantyhose

I have a female friend who I have a friends with benefits relationship. We have been have sex every now and then for 12 years. I'd use dildos and vibrators once in a while. The subject of Trannsexuals came up when she called me to tell me bar in our area has Tranny Shows on Thursday nights.

She said she'd love to go see the show. She also said she would love to see a guy suck a Tranny or two guys sucking each other off. When she came over for sex later that day, she asked me to suck on the dildo. At first I told her no. But she started teasing me with a soft, slow BJ until I agreed to do it. She sat on the couch, held the dildo between her legs like it was her dick. I kneeled on the floor and put it in my mouth. She was was moaning, pushing my head down on it and telling me to suck it you bitch.

I started rubbing her pussy through her jeans and she came. It takes her a while to cum, but it took her only about a minute to cum watching me do this. The next time she brought over a squirting dildo she bought from an adult book store. She filled it up with warm milk and again I went down on it.

Again she was talking dirty and did not warm me when she was going to make it squirt. When she did it, it gag me a little and the milk came running out of my mouth on unto her lap. She absolutely loved it. It was more of a turn on watching her cum so fast and hard than sucking it. Then she pulls the big surprise. She also bought a strap on dildo, pantyhose and heels that would fit me. I put them on and she also dressed up in the same. It was suck a turn on when my nyloned legs rubbed against her nyloned legs.

She sucked my cock through the pantyhose I had on. What a great, different sensation that was. She then said she wanted to fuck me. I was so turned on by this time, I didn't care. I have had fingers in my ass and liked it, so I thought I'd try it.

I laid on my back, she pulled my pantyhose half way down my thighs and mounted me. She put my legs over her shoulders. She had trouble getting it in. Once she did, it hurt. She stopped moving and left it in. I loosened up and it started feeling good. But as she started fucking me harder, it was a combination of pleasure and pain. I told her to stop. She suggested I try sitting on it.

This way I can control that movement. I did and it felt great. No pain at all. She put lotion inher hand and jagged me off while I bounced up and down on her. I reached back and was rubbing her pussy. It didn't take me long to have one of the most intense cums I ever had. It squirt in her hair, face and tits. She came also came a few seconds after I started squirting. That cum was so hard and intense that I was wiped out for about a half hour. She also said that was most turned on she has ever been. We are trying to find another girl to join us that will put on a strap on also so they can gang bang me.


Showing 1 to 3 of 3 comments.
Visexual - 3 year ago

It sounds like you have a really cool girlfriend!

My wife did that for me a few years back. We'd pretend that she was my transsexual lover.

You might try a 'feeldoe'. The way it goes into the vagina you don't need a strap to keep it in. And because it inserts in her, it gives her more pleasure while you're sucking her off. Now, when she fucks you it does seem to want to slip out though.

Damn, the thought of all of this is sure making me horny. I sure wish my wife was still into that!

brandycd56 - 3 year ago

very sexy

tonytnt - 3 year ago

my patyhose