Her Idea

It was a girlfriend quite a few years ago. She was exciting in many ways, and a sexy redhead to add to it. I didn't realize what she had in store. I knew that I wore panties and knew that the main reason was for the fabric, color and cut was much for preferable for me although I do feel sexier than I otherwise would .She also knew what very few people in my life knew. That because of a large dose of steroids due to an illness when I was in my developing years, I experienced one of the major potential side effects. I have to wear jog bras when running/exercising and shape wear when I'm out in public to support my overgrown chest. Yep, breasts. I don't see them as sexy. Embarrassing at times and I'm very self conscience.

She had things in mind. Looking back, I'm not sure if the plans she had were because of the feminine side of me and therefore I wasn't the manliest man for her or if she desired to fulfill a fantasy of her own.

Here's how it went down. When we met she led me to her vanity and asked me to sit down. She then began applying make-up. I have never cross dressed. Just not really my thing and besides I figure if I did try that I would get discovered right in the middle of things and simply die of embarrassment if not worse.

Well, after the initial uncomfortable feeling, I watched her begin to transform me and I started feeling a stirring between my legs. She kept saying; "ooo, you could really be a pretty girl. You have such nice, soft features". Under any other circumstances, I might think she was just belittling me but I was beginning to not care a whole lot as by now my **** was ooozing and calling for attention. "That's out of the question for now, girlfriend," she said.

Well, by now I'm fully made up and she told me to get up that she had something for me. She pulled out a gift bag with a pretty bow and gave it to me. "It's for you". I opened the bag to see a red lace teddy. A red lace teddy. She demanded I put it on. It was a larger size, obviously...she had planned on everything. Still, my **** and balls had to be tucked in order to fit. She asked that I parade around in it for a while. Gotta admit, it was really a bit weird, having never seen my self, nor do I still see myself, as a cross dresser. I don't have a problem with it at all if that's your thing. I have my things too. This was her idea and she had it planned down to the finest point.

After some time where she had me walking around, she was cat calling and the like, she told me she would be with me in a minute. After a few minutes she came out from the back bedroom and was wearing a strap on. Yes, a hot red head waving a ****. Things are looking up.

She laid me back on the bed, put my ankles up on her shoulders, gently pulled aside the thong cut teddy, lubed me and her attachment, then pressed it in. All the way...deep. OMG!!!!! It was unbelievable and she began thrusting me, wearing both of us out. Her breasts seemed on fire, her nipples piercing out stiff. She wouldn't let me touch her so I grabbed behind my knees and pulled my legs back to allow her the deepest access. I looked down to see her juices dribbling down her leg as she worked up a sweat pounding me.

Then the finale. She reached and grabbed my stiff **** and as she pumped me in the *** with her "man hood", she pumped my ****. It didn't take long. I blew up to the point I almost passed out.

Yeah, it was her idea. All in all, not a bad one either!