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Sometimes You Just Want to Feel Pretty

Posted by: Age: 50 Posted on: 15 comments
4 likes 2 views Category: Masturbation Male Solo Tags: Masturbation, lingerie, Male
Going from feeling like the ugly little boy to the man that sometimes feels pretty in a set of sexy lingerie.

If you hang around my posts on picture sites much… or at all… you notice that I am often taking pictures of myself in panties or lingerie. I comment on lingerie posts about things I wish I had, or wish I could wear, if I had tits to carry it off.

Don’t get me wrong here. I’m not Trans-gender. I haven’t fought that battle in my life. I’m happy being male. If I had a super power, it would be awesome to be able to switch back and forth at will… I mean who wouldn’t want to have tits and a pussy to play with? Anyway I digress.

To understand what’s going on we need to get into the way-back machine and visit the “Ugly little boy” that was my childhood. There are multiple issues there, that could fill a Doctorate thesis… but we don’t have the time, nor I the desire, to lay that all out at the moment.

As a young kid I thought of myself as ugly. I was the youngest of five children in a family where both parents had to work to makeends meet. My clothes were often hand-me-downs from my brother. (This wasn’t an issue until most times except when the jeans turned out to be Bell Bottoms in third grade in the 80’s…) My mother cut my hair, which often resulted in a classic bowl haircut. I had large eyes and freckles, on top of that I was short. I was not at all athletic, and I got teased a lot… So my persona was the ugly little boy…

In my teen years I grew, and I grew a lot. I went from being the “little” kid to being well over 6’ tall. I got hairy all over. My legs and arms looked more like money arms to me. My chest and back were more like a fur coat, again to me. While guys and girls in their teens would spend time in the mirror trying to look good, I would avoid the mirror at all costs. On top of this, shooting up from 4’3 to 6’6” in two years, I was scrawny… I barely tipped 100lbs.  I went all of high school without a single date. The girl I went to my Jr. Prom with went with me because she wanted to go, and I was a safe bet. I didn’t get so much as a kiss. When the girls would play games like Fuck, Kiss or Friend… I was always the friend.

In college I met J. Now there are a hundred reasons that my relationship with J was toxic, and horrible, and did a lot of damage to me. But there were some positive points.

At one point I had asked J to shave her pubic hair. She initially reacted with revulsion, and accused me of being some sort of pervert. She hated the thought that I had seen smooth pussies in porn. However one night after some drinks and loosening up, she offered me a deal. She would shave her pubic hair if I would get a full body wax at a place not far from college. Herfriend Jenn was working there and she needed practice waxing… so J basically volunteered me. I got waxed after hours for the cost of just the wax. Anyway… For the first time I saw myself as an adult, completely smooth. I felt more attractive. The smooth skin made me feel sexy. For the first time I liked what I saw a bit in the mirror.

Then J started working at the lingerie shop at the mall. I’ve written about our first forays into Lingerie, and I did a recap of one of our parties. J thought I looked good enough initially. When I was smooth, she thought I was more attractive, enough so that she kept her pussy smooth so that I would stay smooth. When I dressed in lingerie she turned into a wet mess. Something else happened when I put on lingerie though…. I felt sexy. Lingerie helped transform me into this slutty little thing that would lick and fuck all night. Knowing that J was looking at me, knowing that she was getting wet and horny because of me. It was empowering.

When J and I finally went our separate ways, the lingerie got thrown away. And the sexy little slut got packed away for a while. While it would be years before I had so much as a pair of panties of my own, shopping for lingerie never fails to get me hard, and makes me imagine wearing everything.

And then the 2000’s happened. Picture sharing sites. The first time I put a picture of me nude on a site I was terrified. And then the comments started coming back. Women checking out my pictures and admitting they thought I had a good body. I would get wet reading the comments.

A couple of years back when my wife and kids were away for a month I went to Walmart late at night and bought a pack of panties. I was so horny driving home I’m surprised I didn’t cum in my pants. I was barely in the door before my clothes were off. I pulled on this sexy lace thong and it felt so incredibly good. The pink lace holding my swelling cock in place. I loved it. Instantly that feeling of being sexy came back. I was online in and instant posting a few pictures. The love and attention I got back was a huge thrill and a turn on. The entire time they were gone I wore panties day and night.

One day I saw a comment from a guy saying how hot I looked. And how he wanted to suck my cock. Now I have had fantasies about sucking cock since I was young, but this intensified those feelings. I was desirable both to men and women. A day later I got a message from a t-girl calling me sexy. I clicked n her profile and saw this really cute gurl with amazing tits, and this gorgeous pink cock. My own cock gushed looking at her.

So now I put on lingerie… sometimes for other people to see and sometimes for myself. I feel sexy when I do. I’d love it if my wife was into the idea, but I know she isn’t. The very thought would freak her out. But when Ihve time alone, I slip on some stockings on my smooth legs, pull on a nice pair of sexy panties and I feel good. I truly hope you enjoy what you see. You can be sure, the I am feeling sexy, and horny and more than likely stroking my cock, though you never know what or who I am stroking to. 

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