My Qualifications to Write About Crossdressing
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Wet Dreams To Crossdressing free porn video
Confessions of a Crossdresser
I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to understand how I have evolved.
If I was a woman, I would be a cum dumpster: intelligent, attractive, clean, classy, a good dresser, subtly sexy, and fit… but obsessed with a man’s sperm! I have been unable to control myself wanting to be a woman.
But, I am a crossdresser. I’m married, with k**s and I have even been through years of therapy, first for the pornography, and then for the crossdressing. I love my wife and want to stay married. The reality is that I enjoy dressing as a woman, including make-up and a wig. I find this “fantasy” personality dangerously exciting. I like to call myself “Erica”, or sometimes, “Susan”. I think my wife suspects, but we have never talked about it directly. I didn’t intend for this to happen, it just did, and I’m still a work in progress.
Here is my story. The beginning “history” is my best recollection, from young adulthood until the end of 2011. Later in the “dairy” file, I transition to real-time recording of my acting out. I love it so…
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Wet Dreams to Driver’s License
I had no clue what was going on when I awoke after my first wet dream. My pajamas were a mess, but I felt good somehow. I wondered if I had wet myself. I just didn’t understand. Finally, at a Scout campout, I overhead some boys talking about having “pop parties” and “jerking off”. I realized that they were talking about becoming a man and how one’s penis grew into a sex object. A “pop party” was where a small group of boys would all jerk off and race to see who could climax first!
I was too scared to ask any questions. I had 7th grade health class where they talked about “intercourse” and how boys were different from girls. I heard about “getting pregnant” and about “VD”. I noticed girls developing and starting to wear bras under their blouses. Then I discovered the pleasure of having an orgasm.
I can remember learning about how to fantasize and pleasure myself while looking at the women’s underwear photos in the Sears catalog (yes, this was many years ago). Some of them were very sexy for a teenage boy. I particularly enjoyed the matching bra and bikini panty sets, and the pale pink and blue baby doll nighties. I masturbated regularly behind the closed door of my bedroom as I looked through the catalogs. I don’t know how many boxes of Kleenex I went through! I have loved woman’s panties, bras and intimate apparel ever since.
Then, on the way home from high school one afternoon, I stopped at the local convenience store. In their magazine section was an assortment of “girly” magazines! On the front cover of “Club”, was the most beautiful girl I had ever seen: reddish blond shoulder length wavy hair, bright green eyes, innocent smile, arms crossed over her smallish breasts as if to hide them, and wearing a pair of sheer, white, lace paneled nylon bikini panties! My cock hardened on its own. I could have cum right there! I bravely took the magazine to the woman cashier, she looked at me but didn’t say anything. I secreted that magazine away, rushed home, and jerked off looking at the cover and inside photos! Awesome!
Once, my mother walked in on me. I had a catalog open to the panty page and I had a Time magazine open with photos of the inside of a Playboy Club, complete with a photo of several topless Bunnies sunning themselves on the roof top. These were “real” women who obviously wanted sex! I was jerking off, using my usual tissue, when she came in. I quickly rolled over and attempted to close the catalog. She may have known that I was looking at the pics, but I don’t think she knew that I was jerking off. Nothing was ever said. I tore out the Playboy Club photo of the bare breasted beauties, rolled it up, and hid it in a secret compartment of my desk lamp. Between the catalog photos, my porn magazine, and my Playboy pic, I had hours of fun (okay, “hours” comprised of 3-5 minutes of masturbating!)
Then, I discovered the real thing: panties in the clothes hamper! My older s****r had several pairs of frilly bikini panties, my favorites were a pair of pale pink ones with white lace trim. I used to take her panties out of the clothes hamper while the shower was running to cover any noise. I would put them on and jerk off as I watched myself in the mirror. I loved the soft feel of the panties against my cock, and the look of my hard-on stretching against the front panel of the nylon. I would stand in front of the mirror and watch myself. I could shoot a multi-spurt fountain of the mysterious liquid and almost hit the mirror, if I wasn’t careful. Looking back, I guess this was the beginning of my cross dressing lifestyle.
When she wasn’t home, I’d also go through my mom’s stuff and put on her stockings and bras. Panty Hose hadn’t totally taken over at that point and she had gartered stockings. I ran some of her hose trying to find a way to configure a makeshift garter belt, so she may have known of my exploring. I never got caught, but I sure did enjoy dressing-up. I still don’t fully understand why I have this fascination with panties, bras and sexy lingerie, but I am certainly hooked.
I also enjoyed lying in bed masturbating when I could hear the bed creaking when my parents had sex. I tried to listen to hear what was being said, but I couldn’t really tell. I could hear some laughter, so they must have been enjoying themselves. Anyway, it made me hard, and I would jerk off.
Even during these early years, I did like to masturbate a lot. I could cum 3-4 times a day if I wanted to, and I frequently did. When I was jerking off, I could shoot my load up my chest, not quite reaching my chin, and fill my belly button with cum. I wanted to taste it, but couldn’t bring myself to do so. The erotic idea of tasting my own cum would evaporate just as my climax came to an end.
I found it exciting thinking about being caught whether it was in my bedroom, in the shower, or going through dresser drawers. As far as I knew, no one suspected my explorations. And I’m not sure I fully understood what I was doing.
I wanted to taste my own sperm so bad, but I was scared. I didn’t want to think of myself as “gay” and I was worried that it was a perverted thing to do. I could cum in a big way and could fill the little bathroom paper Dixie cups half-way with sperm! Right after I had climaxed, I just couldn’t get myself to drink it! I did dip my finger in and then taste the warm, white liquid, but I just couldn’t make myself tip the cup into my mouth.
I masturbated at home regularly. But once, in the need for excitement, I took my new Polaroid instant camera with me on a bike ride in the woods. When I was alone, I stopped. No one was around and the woods were quiet. I unzipped my jeans to reveal my stiff cock, pressing against the nylon of my s****r’s pink panties! What a thrill! I took photos of my cock and the panties with the instant camera, and then couldn’t help myself, and I jerked off, my seed shooting into the wilderness! To my regret, I wasn’t able to snap a photo at the moment of my ejaculation, but it wasn’t for the lack of trying! I just couldn’t cum and take the photo at the same time. I enjoyed the feeling of the panties under my jeans and cumming in the open air. I thought about tasting my cum all the time, but right after orgasm, this just doesn’t seem to work. I guess one could consider this my first journey out in public as a newbie crossdresser! And my first sexual self-photos! I was more worried about not wanting to be “gay” than what I was really doing wearing female underwear. Was I a fag?
High School Years 1970-1974
When I got my driver’s license, the world of dating opened up to me. My first “love” was a girl that I met in the all-county band. Mary Ann lived in a neighboring town. We really fell for each other. When I would visit her, we would make-out and explore each other’s bodies on the sofa in the living room of her parent’s house. They thought it safe as they sat in a neighboring room, unaware of me having my hand down their daughter’s pants! She would rub my erection through my pants, and sometimes put her hand around my erection, and would bring me to orgasm. Many nights I drove home with a sticky mess in my briefs! Mary Ann was really into sex and exploring our bodies. We graduated to walking to the nearby school playground when the night was warm, and came very close to having intercourse, something neither of us really understood.
Finally, we discovered “parking”. We’d tell her parents we were going to the local Dairy Queen, and then drive to a secluded spot to pull off the road and park. We would kiss, and pet and please each other. Mary Ann insisted that she wanted to give me a blow job. I had no idea what she was talking about. She worked on my cock with her mouth until I came. When I wouldn’t go down on her, she asked me if “it was the smell?” If I only knew then what I know now! Anyway, we lasted for about six months, and then just drifted apart. I later found out that she had come out of the closet as a Lesbian! I lost track of her, but Mary Ann was one sexy girl!
I continued to date as a High School Junior. Most of my interests, being a football “jock”, were the Freshman cheer leaders: cute, petite, skinny, perky girls who wore short skirts and big smiles!
My favorite little freshman blond cheerleader was Judy. She enjoyed kissing and petting. During the summer between my junior and senior years, I would go visit her at her house and her mother, an attractive divorcee, would always leave us alone to watch TV. We couldn’t keep our hands off each other. I mainly put my hand down her pants and played with her wetness. By the time I left for the evening, my cock was rock hard and my balls would be turning blue!
She lived in the country, and the back roads were all dark with few cars. I would pull off on a side road, get out and stand by the back bumper, pull out my cock and, well, jerk off in the summer moon light, right there on the road. Then I would drive home.
I wanted, but never got, a pair of her bikini panties. I particularly remember a frilly pair that I discovered “under a highway bridge” walking home one afternoon from school with her. I slide my hand down her jeans and discovered the lacy panties, and then her fuzzy bush, and then her wet pussy. We kissed and I fondled her.
I would also go visit Judy when she was baby sitting at her aunt’s house during the summer. I wasn’t able to convince her to let me take her picture naked, with her legs open, but I did fantasize about it! We went parking frequently, and many a night after a football game the fall of my Senior year, I would rub her sloppy wet pussy until she came. I loved the smell left on my fingers and the little pubic hairs that were left on the front seat of my car. We even got into a routine after school when on certain days when my mother was away, we would lay on my bed and ravish each other’s bodies. We never had intercourse, but we sure did enjoy each other! We double dated, and even went double parking. I remember one such incident where I was down between her legs, hungrily lapping her pussy, when I glanced up to see the other couple looking over the front seat at us, smiling! Too cool!
Then, it was time to go off to college.
College Discoveries 1974-1978
When I got to college as a small town freshman, I found myself surrounded by lots of sexy young women. We would drink, and even smoke pot. I was having a wild time. I tried to keep things going at home with Judy, but she cheated on me with a local guy, so I ended our relationship. Now I was free to play the field!
I didn’t have a roommate my first semester. I purchased some girly magazines, and enjoyed hours of drinking at dorm parties, followed by jerking off in the privacy of my dorm room. I started with Playboy, and had a favorite edition with Patti McGuire. She later became the wife of tennis player, Jimmy Connors, but I loved her panty-clad photos (white, lace, side bows, sheer), and masturbated over her many times. Wish I still had that edition. Then I discovered Penthouse, which was even more graphic. I really enjoyed reading the fantasy stories in the Forum section and looking at hairy pussies of the smiling, open legged models. Nice!
I had a couple of casual dates, all with non-intercourse sex involved. One particularly unattractive girl, Bev, got me stoned one night and then tried to give me a blow job. I couldn’t get it up and that really hurt her feelings. She was known as the blow job queen of the dorm complex. Oh, well…
I still enjoyed looking at pictures of women in panties, and fantasizing about what lay beneath the sheer nylon. And, like I did as a young teen, I still liked just looking at panties, even by themselves. Unpremeditated, I stumbled on a new trick. I would go down to the dorm’s basement laundry room to wash my clothes. I frequently would take books with me to study and would sit in the laundry room. I watched girls coming and going with their laundry. I dawned on me that they would have panties in their wash load, so, when I was alone, why not check it out? At first, I would take a dry load of a girl’s clothes out of the drier to empty it for my use. This was the common custom in the laundry room. Checking out the load’s contents, as long as no one else was around, I would look for her panties. No harm, right? Well, then it progressed. Even if the drier was still running, I would open it up and look inside, particularly if I knew the owner of the clothes was a cute girl. Finally, I did it: I removed and stole a woman’s panties. Back in my dorm room, I would look at them, play with them, and even wear them and masturbate even more. I loved the feel of the nylon lace, and I kind of liked feeling feminine. It was a scary sensation. I wasn’t interested in men, so I wasn’t “gay”, but I sure liked fantasizing as a woman. Not being enough, I stole several pair over a couple of months. Not enough to get noticed, very subtle, but it kept me happy.
Some times, I would jerk off in them, watching my sperm load fill the cotton crotch of the panties. I would then allow these panties to dry, leaving a stain and smelling of sex. I could sniff one pair as I jerked off with another. I had several favorite pair, all full back bikinis:
• sheer pinkish-white lace
• pale yellow stretchy lace
• bright pink with white elastic around the leg openings and top band.
I learned who the girl was who had owned them as I would pretend to being doing homework as I waited for my laundry down in the basement laundry room. I enjoyed watching her load her things into the drier, and then would secretly remove a pair. I would never take more than one at a time to avoid being too obvious. I’m sure that she missed them, but as I was never caught, she may or may not have figured out what was going on. (note: later, I met her again as she and her husband lived in the same neighborhood as me and my 1st wife. I enjoyed remembering wearing her panties. I still wonder if she ever figured it out). Anyway, I would wear a pair, such as the stretchy yellow lace bikinis and cum in the crotch of the white sheer lace or on the front of the bright pink pair. It was a real fantasy turn-on for me. Boy, could I cum! I would cum in them, on them, and with them! I enjoyed the smell of cum-crusted panties, after I had used them and put them away in my drawer. Just that smell, even today, reminds me of a panty covered pussy, dripping with sperm …my sperm.
I wanted to taste my own cum, and attempted to lick the cum-covered crotch of panties right after ejaculation, but just couldn’t get myself to do so. A couple of times, I even attempted a d***ken “up and over” maneuver to shoot my load in my open mouth. I couldn’t get my cock into my mouth, but it hovered just inches away. I knew then that I wanted a smooth cock head in my mouth someday! I would put my legs up on the mattress, put my head on the floor bending to face upwards, and watch my hand pump my shaft as the swollen, purplish cockhead dripped its clear liquid on my lips. I could feel my orgasm mounting, my balls pulled-up and knew I was going to climax. Then, every time at the last second, (regretfully), just as I was ready to explode, I would always turn my head and shot my warm stream of sperm down the side of my face instead of in my mouth. Something about the moment of climax that kills thoughts of kinky sex…Damn!
I began pledging at a Fraternity in the fall of my Freshman year of 1978. The frat house had a lot of girly magazines tossed around in the bathrooms, and I loved the pics of the scantily clad women in their garters, stockings, bras, panties and heels. When I dropped by the house, I would go into the bathroom to “use the facilities”, sit on the toilet, and look at their photos. I was fascinated by the ones with their legs spread open, showing hairy wet pussies. Frequently, I would shoot my load on a photo and have to quietly remove the page from the magazine. My favorite porn magazine became “Club”. It seemed to have the right combination of raunchiness and lingerie-clad women. I also saw ads for a company called “Fredericks of Hollywood”, and they were loaded with sexy looking lingerie. Boldly, I ordered a catalog to be sent to my dorm room. When it arrived, it gave me hours of excited viewing, fantasizing about wearing the lingerie, and masturbation!
I moved into the Fraternity house in the spring of 1975 and continued to look at porn magazines and watch my in-box for my Frederick’s catalog. I wanted to grab the catalog before someone else noticed it. Luckily, no one ever saw it or questioned me.
I started dating a beautiful, sexy, ex-Majorette, named, Cindy. She was perfect in every way. Our mutual interest in sex led to exploration. Finally, we fucked in her dorm room. Nice! This was my first time. Cindy also liked it when I bought her sexy things. I ordered some things from the Fredericks of Hollywood catalog…this was before the Internet. We both loved the garter belts and stockings. I remember buying and giving her a black garter belt with heavy elastic garters, black hose, and a pair of bright pink micro bikini panties. Then, I began buying stuff that I “intended to give her”, but…well, I kept it myself. I dressed in it, jerked off in it, and even wore it around under my clothes. I guess this was another step towards crossdressing, although I never thought of it in that way. Best of all: no one knew. What made it all the more exciting is that my girlfriend, Cindy, was a real sex kitten!
But then it happened. My “sex kitten” blond bomb shell ended up dumping me. Heart breaking. She even came to collect a few of the panties I had bought for her, at least what she knew that I had. She didn’t want me to have “trophies” of our time together. We had fucked regularly, she had sucked my cock, and I even fucked her in her ass one time. Too bad! She could have been a keeper!
I went through a couple of short term girl friends with heavy petting but no intercourse. One night in the fall of 1975, the guys at the frat house had group sex with some of the Little s****rs of the fraternity, and some of us who didn’t get in on the action, at least got to watch from the rooftop near the window into the room. Cool! One girl got fucked by three guys while another was next to her also getting fucked. Definitely jerked off that night!
I continued to look at the Frederick’s catalog, and finally got up the courage to attempt a shopping trip to a nearby department store. I wore panties under my jeans and went to the woman’s department. Nervous, and not sure exactly what I was doing or looking for, I discovered a table mounded with “sale” panties. Excitedly, I sorted through the pile of sexy lingerie, my cock hard in my jeans, and selected a yellow pair to take to the check out. I was embarrassed when the young girl clerk looked up from the yellow panties on the counter, and looked at me. “Will this be all?” she asked. I nearly died. I stammered, “Yes. I’m getting them for my girlfriend. Do you think she will like yellow?” The clerk just looked at me like I was an idiot, and said “I guess…” and rang up the sale. I went back to the Fraternity house that night, and took the yellow panties into the bathroom with the “Club” magazine, and jerked off in them. Ah!
I repeated my shopping, finding shopping for sexy panties to be a real turn-on. It was “dangerous”, and exciting. I also found that I enjoyed wearing my purchases in private. I loved looking at myself dressed in colorful panties, fantasizing about being a woman, and watching as my hand pumped loads of warm sperm out of my manhood! Sometimes, I worried if I was “gay”, but I didn’t really even know what that meant.
I kept dating and eventually met the woman who was to become my (first) wife. We dated until I graduated. We had regular, if unexciting sex. She used a diaphragm and we only had straight sex, but at least it was something.
We were separated for six months when I moved to the Mid-west for my first job in 1978, and before she graduated from college. I had no problem entertaining myself via porn magazines and a panty shopping trip or two. I searched for Adult Book Stores whenever I could, and collected a nice selection of porn magazines. My taste in porn remained woman in panties and stockings, but I also discovered I was attracted to hard core porn of women giving blow jobs, and sperm cumshots on their faces.
Then, we were married.
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