The Day I Became a Girl
My wife was out of town and I started crossdressing.
(Minor details were changed for privacy reasons. More chapters to come..)
Until recently I did not think of myself as a crossdresser. I separated my sexual desires and secret habits from who I was. Yes, I had been privately dressing in women's clothes but it was a temporary fetish that didn't reflect on me as a person. On multiple occasions I even threw away my girly clothes as if to prove to myself that I was a regular guy. Funny how much a person can change.
Since I started working from home early this year, my crossdressing has escalated to a point I can hardly believe. My wife Hayley almost certainly suspects something but we carefully dance around the subject ("sometimes I wonder what you're up to when I'm gone") rather than face it head on. I am relieved she probably knows even if we never talk about it.
In eight years of marriage, neither of us has had an affair. Of course some people have stricter ideas about what constitutes cheating and to them my recent escapades would cross the line. I can rationalize my behavior though. If my wife had a fetish and wanted to play with another woman, it would not bother me as long as she was careful and the relationship wasn't intensely emotional. I give myself the benefit of the doubt by assuming she feels the same way about me playing with men. She knows I am responsible and as long as she does not ask specifically, she is expressing tacit approval. Or so I like to think.
This whole thing started nearly five years ago on a weekend when Hayley was visiting her parents out of town. We had just watched The Crying Game and (like everyone else) I was fascinated by the transgender character from the movie. I looked up the actor online and since one thing always leads to another on the internet, it wasn't long before I started browsing naughty photos of transgender models and exhibitionists.
The crossdressing photos woke something in me and I was immediately aroused. Ninety-nine percent of my previous fantasies were heterosexual and none had anything to do with crossdressing. On rare occasions I had gay fantasies and even tried anal stimulation while masturbating but it never felt that great. That was about the extent of my kinkiness so it was strange when I suddenly felt attracted to crossdressers. Even stranger was that almost immediately I felt compelled to try it myself.
And so it started. I do not remember thinking, "should I do this?" or "am I turning into a weirdo?”. I just remember picking out a small black pair of panties from Hayley's dresser, sliding them up my legs, and being overcome by eroticism.
It would help to describe myself and give some background about my self-image. I do not know want this to appear egotistical because I promise that is not the case. Nonetheless I have always been complimented about my appearance. The term I get most is "good-looking" with the occasional "handsome" and "he's a looker" thrown in. Despite the compliments and ease attracting female attention as a teenager, my self-confidence stayed relatively low. Throughout high school and college, I was incredibly self-conscious about my physique. I was the only cool person who was not athletic and muscular. I did not even hit puberty until I was 16 years old. Sixteen! Even then my body did not grow half the hair my friends had. My legs were thin and worst of all my penis was small.
When my friends went to the beach, I made excuses for not going because I felt too exposed. This only made it worse because my friends got tans while I stayed fair-skinned. I could never enjoy my supposed attractiveness because it was tainted by a tinge of girlyness. That may partially explain what happened during the weekend my wife was out-of-town.
As I looked at myself in Hayley’s panties, liabilities became assets. My skin was soft and my legs were shaped perfectly. At 5'11 and barely 150 pounds I found that from certain angles in the mirror I could emulate a very feminine figure. I immediately learned to tuck my genitals and make myself look like a girl. After a little while I knew I needed to do some shaving. I do not have much hair anyway but I especially wanted my thighs to be smooth.
I wasn't sure how much hair I could shave without it being a big deal for Hayley to see. Even though our sex life was in a rut, it seemed impractical to conceal smooth legs for long. I decided to start at the top of my thighs and see where it would lead. I sat on the edge of the tub and turned on the hot water. I gently glided the razor down the inside of my inner thighs until they were completely smooth. The sensuousness was mesmerizing! I continued with the front of my thighs and worked around my ass.
I stood sideways in the tub with my legs extended apart so I could get to every crevice. I knew it had already gone too far but the gratification was increasingly worth the risk of Hayley seeing me shaved. I would think of something to say if I had to. Swimmers shave their bodies, right? Besides summer was over so maybe I cover my legs for a few weeks.
I continued below the knees until my entire legs were smooth and (if I say so myself) extremely sexy. It was thrilling and I oozed pre-cum. I wasn't finished though because my pubes and underarm hair still needed work. Armpit hair has always seemed yukky to me so I did that next. Once they were smooth I felt a strange freedom when I put my arms above my head. I practiced poses in front of the mirror as if I was being photographed for the Sports Illustrated bikini edition.
Lastly I came to my pubes. Using scissors I carefully trimmed the area above my penis until my my hair was about half an inch long. I completely shaved my 'goody trail' and around the edges until my pubic region was a nice little triangle. While I was at it a shaved the few little hairs on my chest that were barely visible anywawy. To finish it off I used a fresh razor to remove all the hair on my balls and underneath. I had never shaved my balls before and I fell in love with their softness. I stood over the edge of the tub and slowly lowered myself until my sack rested on the cool porcelain. It felt wonderful.
Even though I shaved very slowly and carefully, I had minor razor burn so I rubbed Aveeno lotion into my thighs. Like everything else that day, it felt so good that I couldn’t stop. I rubbed my belly, arms, ass and just about every other part of my body.
It is a strange thing to be sexually attracted to yourself but I totally was. As I fondled myself there was an odd sense of detachment from my cock as if it belonged to someone else. It kept oozing precum and I really craved it. I desperately wished I could contort my body enough to blow myself!
Next I chose a t-shirt from Hayleys's dresser and pulled it over my head. I had never paid attention to the way shirts are cut but I loved the way this one made my waist look thinner. I wasn’t sure what to do for breasts. I stuffed anything I could find that might resemble a breast but nothing looked right. Finally I just picked a bra with slight padding and that was enough to enhance my shape without looking artificial.
I walked around our house feeling almost drunk on my femininity. I relished the feeling of my smooth thighs rubbing together and each time I saw my reflection in a mirror, I was impressed by how effortlessly I walked like a girl. A feminization circle had begun. The more feminine I looked, the more feminine I felt and the more feminine I felt, the more I wanted to look like a girl. The day went on like that and I tried different outfits and lingerie from Hayley’s closet. I was a natural.
I didn’t spend much time on my face or hair because it didn’t seem like I needed to. I am lucky to have soft skin which makes the girl-next-door look easier to achieve. My hair was longish in the front and I used hairpins to feminize it. I am not a huge fan of make-up so I definitely didn’t go overboard on myself. I put on lipstick and that was it. (Five years later hairpins and lipstick are still my mainstays.) I wish I had photographed myself that weekend because I remember feeling passable as a woman. I probably wasn’t in reality but I sure felt it.
It was inevitable that I started fantasizing about men while I was dressed like a girl. I would lean with my back against the wall and imagine a guy pressing against me and kissing my neck. That led to lying in bed and imagining a man on top of me. Even though my past experiences with anal stimulation weren’t memorable, I really wanted to put something inside me.
Hayley keeps a vibrator in her dresser and I wanted to use it but the size was too much. Even with lubrication there was no way I could insert it. I looked around the house and eventually opened a drawer with about a million candles of different sizes.
I picked one of the skinnier candles and went back to the bedroom. I thought it best to put a condom on it and I also got KY jelly out just in case the condom lube wasn't enough. I set the candle on Hayley's side of the bed and pulled the covers back on my side. I was still wearing panties and a t-shirt and felt sexier than ever. I turned off the lights and there was just the right amount of light coming between the curtains.
I imagined someone in our backyard peeking inside and that got me even more aroused. I slowly climbed on the bed and remained upright on my knees with my arms stretched over my head. This caused my t-shirt to rise and exposed my torso which was flat and smooth. I tugged my shirt down in false modesty to teasethe imaginary person watching through my window. Then I bent forward on all fours with my ass angled up and basked in the realization that I was completely fuckable!
I turned over on my back and lightly ran my hands across my body, occasionally sliding a finger under my panties. Lying in the missionary position I caressed my thighs and pulled my panties to the side so my hole was exposed. Every nerve ending was turned on as I gently used my index finger to tickle myself.
The person watching through my window became more vivid and I imagined he was my neighbor from down the street. His name is Blake and for some reason he eased perfectly into my fantasy. (Blake is a pharmacist at Rite-Aid and I still fantasize about him all the time.)
I slid my panties off and reached for the candle. I added a dab of KY to the top and opened my legs. The jelly felt cold as I glided the candle an inch inside me. I closed my eyes and fantasized that Blake was on top of me. He rubbed his hands up and down my arched torso and his cock slid gently into me. I imagined him kissing me while my hands were on his hips pacing his body.
I could feel an orgasm building quickly even though I wasn't masturbating. I could not handle the excitement for long so I wrapped my fingers around my cock and started jerking. An orgasm began immediately and the sensations radiated from my groin and prostate. I couldn't remember it ever feeling so good. The first shot of semen hit my chin and the rest landed on Hayley's shirt. Oh my god, the intensity!
I was exhausted and my heart was still racing as I lay in my own cum with the candle still in meAfter a few minutes of lying motionless I started teasing my belly with the tips of my fingers and lathering my skin with semen. I pulled the t-shirt to may face and sipped from the puddles until they were just damp spots.
It was the first of several masturbation sessions that weekend and an obvious sexual turning point. Until that weekend I could not have imagined that one day I would crossdress in public or make out with a man. I still haven't been fucked but something tells me it won't be long now.