MEN in PANTIES STORIES
 
 

I am a 30-year-old straight man and for just about as long as I can remember, I have taken great interest in women’s clothing and styles, especially women’s lingerie and underwear. One of my earliest memories is of my mother shopping for a bra and my friend and I thinking it was hilarious to crush down the padded points of the bras with our faces. When I was about 12 years old, I found myself compelled by silky panties. When my sister left for college she left behind her room in my parent's house and bunch of clothes that she decided not to take with her. Whenever possible, I would help myself into her lingerie drawer and take as many nylon and satin panties as I could. I would then put on each pair over the next until I could hardly feel my erection underneath. The feeling of silky, slippery nylon rubbing and sliding on my body is still one of my greatest pleasures. I would take my time as I put each pair on and off repeatedly. And sometimes, I wore nothing but silky panties when I slept. I felt satisfied but there was still something missing.

The first time I masturbated I was wearing nude, nylon pantyhose. After wearing and playing with panties for the first time, it took me about a year to experiment with masturbation. As I was lying on my bed wearing the pantyhose that I would “borrow” from my sister, I told myself that I would try masturbating just one time. Since that night, I love to masturbate while wearing women’s, silky, sexy lingerie. Sexy for me, generally means satin or nylon preferable shiny or shimmery. This love of feminine clothing is ingrained in my sexuality. One of the greatest thrills for me as a teenager was to masturbate while wearing a friend's sister’s or mother’s panties and lingerie. Occasionally, I would stay overnight at friend's house. More often than not, I would end up sleeping in the empty bedroom of a friend’s sister or parents if they were out of town. By my count, I have worn the panties or lingerie of about 20 different women. I always took great care in never soiling their clothing and putting it back in the exact spot from where I found it. I suspect that no one ever knew.

There are 4 people who I told of my fetish: two past girlfriends, a female friend who told me about her bi-sexual experience and my wife. As an adult, I have been tempted to cross-dress in public but I have never really considered it because I never have craved that kind of attention. I also figured that however satisfying it may be, I would be so self-conscious that it would definitely take away from the experience. Although, I realized, there is one day a year where it is OK to be whoever you want to be and dress however you want to: Halloween.

Last Halloween, with my wife’s help, I wore women’s clothes in public. Every Halloween, I see men, including a number of my friends, “go as a girl”. It always gets a few laughs and no thinks twice about it, except for me. Since I have a long history with women’s clothing, I have probably put more pressure on myself for fear someone would find out my secret passion. I told my wife about my desire to dress like a woman for Halloween last year and she came up with a great tandem costume idea. The party we were attending had a theme and our costumes were clever and simple: sweaters, skirts, wigs, unisex shoes and nylons. The party was great. The costumes were a hit and, of course, I wasn’t the only man dressed as a woman. And, unintentionally, I think I sexually confused a few men and women. I have been blessed with a body that looks attractive in both men and women’s clothing: long legs, shapely bottom and full lips that my wife loves to kiss. This costume was one of the most comfortable costumes I have worn because it fit me. I already owned all of the underwear. My wife and I frequently go on, discount store, shopping sprees where we speak in low tones and she buys the items I pick out for us. What an angel! And the skirt and sweater were purchased in my size too. I took great pleasure in dressing for the party.

After showering I first put on my garter belt and nylon stockings. The garter belt is white with tan embroidery and the stockings are nude. I then put my stretchy, white, nylon panties over the garter. I first saw Cybil Sheppard do that in the movie, Paris, Texas. Since my panties were worn on over the garter belt, I didn’t have to undo the garter belt every time I had to pee. When I did have to pee, I would make an effort to wipe my penis on the cotton crotch of the panties to keep them looking pretty for as long as I could that night. I then put on a stretchy nylon bra and filled the cups with pantyhose. I made my fake breasts and put a white, nylon camisole on to protect myself from the wool sweater. I applied my wife’s deodorant and perfume and looking at myself in the mirror, I felt beautiful. My clothes were soft and comfortable and I smelled good. I stayed up until the last guests had gone to bed so I could enjoy this experience as long as possible. To make the night complete, I knew, one way or the other I was going to cum.

By the time I got to bed my wife was asleep. I had wanted to lift up her skirt and eat her pussy all night long but since that wasn’t an option, I was going to fuck myself silly. I slowly undressed myself in the bathroom mirror, with each button undone, revealing more of my silky chest. I shed the skirt, sweater and bra and since it was a special night for me I decided that my whole body deserved special attention. I found my wife’s hand cream in her bag. It is a creamy peach smelling liquid. I then slowly removed my panties and inspected them. They smelled like I had just put them on and had no stains. I placed my panties crotch side up on the counter, turned around and started to drip the cream down my butt crack and onto my anus. The panty’s crotch caught any cream that dripped off of my body. I then rubbed the cream onto my butt cheeks and into my anus. I applied more of the cream onto my panties crotch so that it was soaked. I decided to switch my garter and stockings for pantyhose to sleep in. I put my panties back on and wore my nude pantyhose over them. With every step and every movement I felt my butt cheeks slide together like a wet, wanting pussy.

I crawled into bed with my wife and proceeded to rub my penis through the slippery nylon. I pulled down my pantyhose, pulled my panty’s crotch to the side and slid my finger into myself. Between the gentle rubbing of my hand on the nylon on my penis and my finger inside of me, I was able to cum with only the slightest of movements. I had another pair of silky nylon panties ready to soak up my orgasm. I fell asleep wearing the camisole, pantyhose and my favorite panties. I woke up early, came again, and changed back into boxers and a t-shirt. That night was the climax of my career as a masturbatory cross-dresser.

I would like to, someday, cross-dress again for Halloween. It might not be for a few years, as I do not want to be “found out”. I hope someday people can dress however they like and not be judged or harassed. I doubt that day will be in my lifetime. As for now, I am happy shopping with my wife for silky toys for us to play in.