Confessions of a Crossdresser
Erica’s reveals his REAL life crossdresser secrets for the first time
Erica says, “I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself”…read on to discover…
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 as a female, masturbation, and inevitably, seeking men to please.
I started out as a pre-teen as a panty fantasizer and have progressed to where I am today. I do not consider myself gay, and outside of my fantasy character, I am attracted to women, not to men. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a family. But, I have evolved to a cock sucking crossdresser (sorry for being so graphic).
I’m writing this to try to understand how I have evolved.
If I was a woman, I would be intelligent, attractive, clean, classy, a good dresser, subtly sexy, and fit… but obsessed with pleasing men! I have been unable to control myself wanting to be a woman.
But, I am a crossdresser. I’m married, with kids 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.
I’m not passable, and admit that, although I try to look attractive, I am not in a position to take hormones, shave myself smooth, or otherwise become the woman I fantasize about.
I’m just a normal guy. Well, for the most part…
Here is my story…
The beginning “history” is my best recollection of my crossdressing, from young adulthood until 2004. I started out not really thinking about what I was doing, or why. Later in my “dairy” files, I transition to real-time recording of my acting out as I evolved into role playing as a woman. I love it so…
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 Sears 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 sister 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 sister’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.
Sometimes, 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 drunken “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 Sisters 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.
First Marriage 1979 – 1993
My first wife allowed me to try a lot of things with her. I bought her stockings, garters and sexy things that she would wear for me. I ended up fantasizing more about what she was wearing than about her. We had straight sex, and I went down on her frequently, but I couldn’t get her to take my cock in her mouth or even stoke it much. Oh, well…
I found that I enjoyed the excitement of shopping for sexy lingerie for her. Just in the town where we lived, which was a college town, I would go into department stores, a local specialty lingerie shop, and even an adult book store, to shop. I gave her some of the things I bought, but then I started my own collection. I hid a couple of bags of lingerie in a closet and she never knew. I worked swing shift and she worked days, so I had a lot of time to myself. I shopped at Sears and Kmart as they had a nice selection of sexy, and slutty, woman’s things; plus they were cheaper than the full blown lingerie specialty shops.
I bought sheer baby doll nighties (I remember a frilly pink one and sheer pale blue one, both with matching string panties), garter belts, stockings, bras, panties and finally, heels. Just the excitement of shopping for sexy women’s clothing was worth the thrill. I liked to shop while wearing something sexy under my man-clothes. I found that I needed to put a non-lubricated condom on my cock to keep the pre-cum from soaking through my panties and pants and creating a wet spot on the front! Sometimes, I would come very close to climaxing while I was shopping.
That was so cool! If I had reached down and touched my stiff cock, I knew that I would have exploded! It is a real challenge to keep from showing my delight as I shopped, standing in the panty section of a department store with women all around me, as I handled panties and bras! I wondered if any of them suspected that I was shopping more for myself than for my woman. Women were so lucky to be able to wear such sexy clothing if they so choose to do so.
They could dress, open their legs, and get fucked! Wow! There was a local adult theater that I visited a couple of times.
I usually went in the morning when I was getting home from working the midnight shift. My wife was at work, and I had time to myself. I would take panties and thigh high hose with me, and change into them at work. Then, I would sit in the mostly deserted theater and watch the porn. I think that this is the first time that I seriously considered approaching another man to offer him a blow job, but I didn’t act on it. I saw a couple of single men in the theater.
I wanted a cock in my mouth, but was much too afraid. I didn’t understand my urges. I wanted to be like a woman, but I didn’t want to be gay. Watching a porn star, Seka, who was always dressed in sexy, frilly panties, bra, garter belt, stockings and heels as she would suck and fuck her men, made me want to be like her! To this day, she is my porn “goddess”.
Not helping my concern about maybe being “gay”, I remember one business trip. I had an upgrade to First Class and the male flight steward paid particular attention to me. I was wearing panties under my clothes and didn’t think much about it as I downed a couple of Scotch Whiskies. Then he bent down to tell me a joke. “Did you hear about the guy who was asked to bend over, and spell “run”?” When I looked up at him, he held my gaze and said, “Get it? R – U – N?” He smiled and moved off. It took me a minute to realize that he was a gay and was coming on to me. He was referring to anal sex! OMG! I tingled but was too scared to take him up on his flirting offer.
We moved back to the east coast in 1985, and had our first child. I did my best to behave.
My lingerie collection grew and I even traveled with it when I went on company business trips. Afraid of discovery, I would go through an emotion that had me get rid of everything that I had. My first (of many to come) purges. At the time, I would convince myself that I needed to stop doing what I was doing, and I would discard my collection. The time, effort and money just didn’t seem worth the risk of getting caught by my wife, or thinking about what I was really doing it all for. Then, after the initial good feeling of “starting clean”, within a week, I would regret what I had done. I really hated it. I got rid of some very sexy stuff.
I have never forgotten a favorite pair of sheer, frilly, red panties that I would wear along with a red garter belt and red lace-topped stockings. I remember wearing them under my jeans and how my erect cock could easily pop out of the elastic band at the top. I loved to jerk off while wearing them. I also remember wearing the red lacey panties, the red garter belt and white hose one time while attending a business conference. I needed to visit the men’s room, and knowing that I didn’t want to risk standing at the urinal pulling my red panties aside to pee, I went directly into a stall. I sat on the toilet, pants and red panties down on my white stocking covered legs. I heard someone come in next to me.
Then I saw it! It was a woman, wearing heels! OMG! I had gone into the wrong wash room! I hoped my man’s shoes didn’t show under the stall. I waited for her to depart, and then, before anyone else came in, I scurried out. I don’t think anyone saw me. Oh, well…I just loved those red panties. But, they were now gone.
Then I had a serious car accident in August 1985, and suffered some head injuries. The recovery period was long. My boss had brought a computer to me (back in the days of big desk top computers) to help with my recovery. With my wife working and be being at home for several months, I had a lot of free time to do what I pleased. I found that I fantasized a lot, perhaps due to the pain meds.
Then, I began using my computer to write sexy stories about being a “fantasy woman”. Don’t ask me why I started doing this, but it gave me a thrill to record fantasies. I pretended to be a college coed, named Alexis. My mission at school was to serve as a “cum dumster” for as many men as I could. I wrote about having sex as a woman, giving blow jobs, group sex, and everything. It was all very unrealistic, but I enjoyed writing about it. I liked the feeling to be a sexy, intelligent woman, desired by men.
Having cocks in every orifice and delighting my men by way of explosive orgasms, was a real turn on for me. I kept the stories on floppy discs for some time, but had to get rid of them to avoid being discovered. I still didn’t understand my passion of crossdressing or fantasizing as a woman. I wasn’t attracted to men, and didn’t want to be gay, but I did love sperm and the idea of hard cocks!
Time passed, and I finally went back to work. To this day, I wonder if my head trauma contributed to what was to happen years later as a crossdresser. I had also started shopping again and had a secret nice collection of feminine things all over again!
But, I still wasn’t satisfied. I wanted more. I loved the fantasy of being a woman and serving men. My writing and my shopping just fed this fascination. Whenever I had a private moment, whether around the house or while traveling on business, I sought out Adult Book Stores. I would troll the aisles, not knowing what I was really wanting, and would buy a magazine or two. After finding a good photo to masturbate on, I would tear-out a couple of particularly sexy photos of women, and add them to a folder I was keeping of favorite shots.
I moved into a sales organization in 1988 and began to attend annual meetings, and such. This gave me the opportunity to seek out actual Frederick’s of Hollywood retails stores. I remember finding one in Florida on a trip, and purchasing several garter belts (white and pink) and silky lace-topped and regular stockings (black, white, pink and pale blue). Of course, I also bought panties.
As the years went by, I cheated on my wife several times with one-night stands. I wasn’t proud of this, but I needed some passion in my sex life. I had opportunities on business trips. Once, while attending a national sales meeting for the business I was with, I went dancing and drinking with some buddies. One guy was known for his ability to pick-up women. Then, to my surprise and delight, a young woman actually hit on me at the bar. One thing led to another and we went back to my place to fuck. I wondered if she wanted a long term relationship, but she just wanted sex. Nice, but I had started down that slippery slope of affairs…
My next opportunity came on an annual “boys” ski week vacations out to Colorado 1988 – 1991.
In each of several years, I always seemed to find a young woman to befriend and screw. I remember one worked in an advertising agency in New York City, and one, named Caroline,was a nurse from CA. The former just wanted sex, that later wanted more. I had lied to her that I was single. Without thinking, I told her roughly where I lived and gave her my real name. She had a great body: trim, athletic, and feminine. She was a great fuck. When I got home, I found a recording on our answering machine from her. OMG! I was lucky that I listened to it and erased it before my wife did. She had tracked me down and called me. My recording on the answering tape, mentioned my name and my wife’s.
So, I snuck out of the house to call her. I found a pay phone, and dialed her number. I got an ear full. I listened to her angry tears as she realized that I had lied to her. After two weeks of trying to keep her as my mistress, telling her that I was going to get a divorce, we parted ways. This was a shame as she was really cute and smart. Anyway, six months later, I had a business trip to San Diego. Once at the Del Coronado Hotel, I got drunk and I dressed in panties and stockings in my room.
Wanting to have her come over for sex, I called her apartment. I was a drunken mess. I left her a message, hoping to get together. If she had contacted me back, what would I have done? Stayed dressed?? Fortunately, I never heard from her.
I was sad that I had hurt her so, but my intentions were never honorable from the start. Lesson learned: don’t give out where I live or my last name!
I continued to visit Adult Book Stores when I traveled. This was before the Internet. I would wear panties under my clothes, and occasionally more. Sometimes I would masturbate in the pep show booths (some even provided rolls of toilet paper). I walked the aisles, glancing at the other men doing the same, and looked at the magazines. I usually would buy one or two of the glossy, color magazines featuring sexy lingerie or cum-shots.
My collection of lingerie grew and I kept several bags hidden in my drawers and closet. I had panties, bras, nighties, stockings and garters. Finally, I decided to experiment with makeup. I went to a drug store holding a slip of paper as a shopping list, pretending to be on a shopping trip for my wife. I bought eye shadow, mascara and lip stick. I took these with me on my next business trip, which happened to be to MI. I planned my arrival early so I could go find an Adult Book Store to cruise.
I drove my rental car to a dark street near the book store, and struggled into the panties, garter belt and stockings I had brought. I then redressed in my man clothes. While sitting in my darkened rental car, I applied a subtle touch of makeup, just enough that I knew it was there but that wasn’t too obvious. I applied just a touch of mascara and eye shadow with a whisper of dark pink lip stick. Turning on the overhead light and using the visor vanity mirror I looked at my first make-up job. Then, I took another big step: I slipped on the pair of women’s flats that I had bought.
Thinking that the shoes, which made me feel sexy, would hardly be noticed, I slid out of the car. This was too exciting. I lost myself in my fantasy of being a woman and walked to the store. I remember going inside, and casually strolling the racks of porn magazines. Was I hoping that no one would notice, or hoping that someone would notice? I did see the store clerk glance down at my feet once.
Then I realized that my subtle wearing of women’s shoes, even if they were flats, was noticeable. Oh, well…I was so excited and could feel my hard cock in my panties. I moved to the pep show booth area. As I pulled aside the curtain to slip into a booth, I noticed a man watching me. He had also spotted my shoes. I held his gaze for a long moment, and then stepped inside. I didn’t know what to do next!
Silently, the curtain opened and the man entered the booth. It was dark, but I could tell that he was older than my 34 years. He slipped a couple of quarters into the pep show machine and the noises and images of women getting fucked filled my senses. He placed his hands on my shoulders, and I got down on my knees. What was I doing?! I unbuckled his pants, found his soft cock, and put it in my virgin mouth.
After a few minutes, when it wouldn’t harden (this was pre-Viagara), he lifted me to my feet whispering that “it was ok and his fault”. He put his hand on my erection. OMG! My hard cock twitched to his touch. He undid my pants, and was delighted with finding me wearing a garter belt, stockings and panties. He pressed his hand against my erect, panty-covered cock, and started to masturbate me. Within seconds, I exploded my load in my panties, onto the floor and in his hand. I was embarrassed by my premature ejaculation, but it was my first time.
We quickly said our good-byes and he departed. I was in a state of sensual overload. What had I done? Was I glad that he hadn’t cum in my mouth, or disappointed? Oh, my! This truly was a new chapter for me. I departed the booth and the shop to go back to my hotel room, convinced that I wasn’t a “cock sucker” or “gay” as he hadn’t been hard or climaxed in my mouth.
I was good. But I knew then, that I wanted cock and there was no going back.
Back at home, I frequented a couple of local Adult Books Stores whenever I could get away. I always had meetings for various organizations and clubs, so my coming and going did not raise any eyebrows with my wife. I liked to check the bulletin boards, and scrawled messages in the pep show booths, thinking that I could hook-up with someone. Once, I even tried. I went to a hotel room posted, knocked, ready for I don’t know what. No one answered. I was saved from myself, not for the first time, or the last. I did purchase video porn tapes that I would watch whenever I got a private moment at home. I didn’t think that I could convince me wife to watch porn with me, although the idea was exciting to consider. We enjoyed a normal sex life.
I was getting bolder. We had two Porsche’s, traveled the world, and enjoyed the consumption of dual incomes. I felt entitled. I started a longer term, more emotional affair, with a young girl in my office. Julie was nice, knew I was unhappy in my marriage, and okay with having secret sex. I don’t know how I pulled this off over a period of months, but if my wife suspected, she didn’t acknowledge it. I would go out to a “meeting” in the evening, and end up at Julie’s apartment. We would have sex, and I would clean up and go back home. I wondered if I smelled of sex, but my wife never said anything. As to be expected, as the flames of our sex dwindled, Julie and I finally drifted apart.
This was dangerous, and exciting. I was obsessed with sex. Probably good that this was all pre-Internet, or I could have gotten even more carried away.
I had built up my lingerie collection again, hiding things in plastic hotel laundry bags in my drawers at home. I don’t think that she knew about my collection, but she had allowed me to keep some porn magazines in the house. I wouldn’t “read” them in front of her, and perhaps she herself read some of the stories. I had a half dozen magazines at any one time. I still loved to shop for panties while wearing panties under my clothes.
The feel of the soft, sheer panties on my cock and the thrill of looking at all of the sexy panties and bras would cause my erect cock to leak clear pre-cum, wetting the panties. When I returned home, or to my hotel room if I was traveling, I would watch myself in the mirror as I masturbated. The feel of my cock being restrained in the sensuous material of the panties, and the sight of jerking off while wearing panties, a garter belt and stockings, was a thrill. I loved it!
My wife didn’t know about my addiction to panties, and I don’t think I really considered what I was doing and why. Then one day, I boldly, and drunkenly, asked her if I could wear one of her thongs during our sex act. She agreed, and wearing her red thong, my rock hard cock protruding from the elastic waist band, we had passionate sex. I loved the sensation of the soft panties on my hips as I fucked her. So, I started wearing her panties on special occasions when we had sex. I was the director of all of this, but she did comply. I don’t think she suspected that I enjoyed wearing panties. She thought it was just a kinky way to spice things up when we were having sex. I loved it!
In my browsing of the local Adult stores, fascinated by the large rubber cocks on display in the cases, I purchased, over time, several vibrators to use on my wife. I started with a traditional white one. She was reluctant the night I first introduced her to it, but after sharing the bottle of wine with me, agreed to my using it on her.
She loved it. I slide down between her open legs as she watched with her head on her pillow.
Her pussy smelled great and she easily became wet as I kissed and licked her hairy, glistening pussy lips. Switching on the vibrator, the humming noise seemed loud. I gently began touching her sensitive area with it. As she got comfortable, her hips began to respond. Glancing up, her eyes were closed, enjoying the sensations. I gently drove the white, vibrating monster deep inside of her wetness, and she moaned. Lying between her open legs, my hard cock under me, watching her pussy swallow-up the vibrator, was so exciting! It was all I could do not to cum myself.
I moved the vibrator in and out of her pussy and her hips began to move as if they had a mind all their own. With a cry, her body shook and her hips thrust up hard! She came! Reaching down to pull me up to fuck her, I pulled out the vibrator and, still buzzing, tossed it aside. I entered her warm wetness and our hips thrust together violently. I came quickly and filled her climaxing pussy with strong spurts of my sperm. Exhausted, we collapsed. I switched off the humming vibrator and he snuggled together without a word.
Based on this first adventure, I started buying other styles and colors: purple, pink, and a large realistic cock-shaped gyrator. I can vividly recall lying between her open legs, working the large cock vibrator in and out of her wet pussy. My face was inches away from her bush as I stretched her pussy with this monster. She loved it! So did I. She would buck and climax like a champ! Me getting my rocks off inside of her was just icing on the cake for both of us. I suspected that she used these sex toys when I was away traveling and masturbated herself. I found the idea of this exciting.
I had a business convention come up in 1992 that was being held out in Las Vegas. I was away from home, and enjoying the drinking and signs of sex everywhere. I found an adult book store and purchased a nice, think glossy publication of cum shots.
Then, one night, I did something I had never even considered before: for the first (and only) time in my life that I hired a prostitute. I had scanned the free publications you could find on every street corner, picked a woman who looked good in a garter belt and stockings, and called for her to come visit me at the hotel. I was drunk, but I knew what I was doing. The first indication that my fantasy fuck was not going to be as I had imaged was when she came to the door wearing pants. No skirt or stockings! I was disappointed. We talked price and I gave her my last $100.
I told her to lay on the bed and masturbate for me. She did a lame job of that. Then, I told her that I just wanted a blow job. She wouldn’t let me kiss her, and she had me wear a condom to give me that blow job. It was over in a flash. I suffer from premature ejaculation and this was no exception. Within 2 minutes, I came. She looked at the sperm filled condom, looked at me, and asked “so, are you done?” I felt like a fool. She stood and left. After she left, the cum filled condom remained. I started looking at porn using the dial-up connection on my laptop. This was early on with the free Internet porn sites, and slipped on a pair of panties I had brought with me.
Enough time had elapsed since I had cum that I was feeling horny again. I saw my used, sperm-filled, condom lying on the sheets of my hotel bed. What the heck! On a whim, I put the used condom in my mouth and then quickly, without thinking any more, I sucked it inside-out, releasing its load of my sperm into my mouth. I swallowed my sperm load and licked the condom. Wow! I was thrilled and I liked it. It was just a slippery liquid and didn’t have much flavor. This was my first time having cum in my mouth and swallowing it. Finally! There was no going back now.
I continued buying stuff and dressing and looking at porn and masturbating, all the while still having sex with my wife once per week. She would dress for me and allow me to fuck her while she was wearing stockings and a garter belt.
I also worked to keep her well filled with my sperm. Although she wouldn’t consider giving me a blowjob, I initiated oral sex on her. I think she liked me going down on her more than me fucking her.
But, things weren’t good with our relationship. Through work, I met, and I fell in love with a new woman in 1993, who is now my current and final wife. We started dating before either of us was divorced. We didn’t have sex for several months until we booked adjoining rooms at a historic bed and breakfast. That night, after dinner, drinks, and a hand-in-hand stroll around the village, we ended up in bed together. I think that this was the night she made up her mind to leave her husband. After this first time, we found ways to secret ourselves away in B-and-B’s and enjoy romantic, loving sex.
When we were secretly dating, and we were both still married, we fucked in her house one afternoon. We were returning from one of our joint business trips and I was just dropping her off. Her husband was at work and I went inside with her to say good by. One thing lead to another and we ended up in each others arms. We tore each others clothes off and had sex on the floor of their family room. I got carpet burns on my knees, but it was exciting thinking about doing another man’s wife in their own house!
My 1st wife then found a woman’s sweater in my car, and discovered some hot email notes I had printed that I had sent to my new lover. Confronted, I told her that I wanted a divorce. It got very messy. I moved out and the legal battles began.
Fortunately, I had by collection of sexy items when I moved out to a townhouse in the city. In the divorce, the property was split with my first wife. What was fascinating was that she evenly divided the vibrators, choosing the ones she wanted first, and then giving me the remaining ones! She did catch me with bags of lingerie when I was attempting to move out. She inspected the trunk of my car and discovered them. Although she asked me about it, I never divulged their origin and use. I think she believed that they were trophies from my “other women”.
Alone now, I even purchased an inflatable “woman” and, while dressed myself, would dress and fuck this submissive blow-up doll in the quiet of my new apartment. I tried to have oral sex, or to kiss her mouth, after I had filled one of those openings with my sperm, but again, the drop of my post-orgasm passions just didn’t allow me to do so effectively.
Besides regular sex with my new Love, I continued to wear sexy women’s outfits, look at porn, and masturbate. But, I knew…I wanted a cock in my mouth.
Love of my Life (1993 => )
I dated my new Love, was married in 1995, and remain so now.
In the beginning, my new bride wore the sexy outfits that I would buy for her. She looked great: slender, petite, narrow hips, nice butt, small perky breasts! When she finally moved out on her now ex-husband, we had sex in her new apartment (I remember the red outfit she wore for me one morning), or in my townhouse. It was always straight sex, although she allowed me to go down on her and she definitely enjoyed that! She was having intense orgasms and I felt great helping her.
After we were married, our life, and sex, shifted into a more normal, comfortable mode. We had children and resultant obligations to tend to.
Sometimes I would go through her things in her lingerie chest, wear her panties, cum in the soft cotton crotches and then wash out my sperm stain. I particularly enjoyed cumming in the off-white silky string bikini panties that she had worn on our wedding day. It was dangerous to dress at home, with my wife and numerous children around, but I enjoyed the thrill. I frequently looked at porn and fantasized about what it must be like to be a woman, at least sexually.
I wanted to be a woman badly and my dressing helped me deal with it. I was lucky that I never got caught while either dressed, masturbating or going through her lingerie drawer!
The Internet was in full bloom now. Adult magazines weren’t needed any more. I liked to look at websites that showed a woman sucking a man’s cock, particularly when he would cum in her face. I learned that this was called a “facial”. I fantasized about being a woman, on my knees, sucking cock…better yet, cocks!
I still continued to buy outfits, including skirts, heels, jewelry and make-up. I hide my multiple bags of clothing successfully for a number of years, ten to be exact.
My first time of getting “caught” came at work in 2000. I was looking at porn on my company laptop, in my office (this was before they had ways to block access to such sites), and a woman colleague came into my office. I never knew if she saw my computer screen, but I suspected that she did.
She was a bitch anyway, but she was even “colder” towards me after that. Within six months, my boss came to see me un-expectantly. He said that he had gotten an IT report that my computer had accessed forbidden porn internet sites and he wondered if my son had access to my computer. He was giving me a way out of the situation and I appreciated it. I wondered if the office bitch had ratted on me, but I never used the company system to do this again!
But, I did continue to dial-in to the Internet and view porn sites. I discovered how I could download photos onto CDs, and I started doing so. I would spend hours cataloging the photos by their content. I would group together photos by groups such as: cumshots, fucking, lingerie, Lookers-Blond, Lookers-Brunette, Group, and so on. I could watch them and masturbate whenever I wanted. I shifted jobs, continued to collect porn, dress and fantasize.
I would travel with my outfits, dress, look at porn in my hotel room and masturbate. I loved it! I had some great outfits and mind blowing orgasms! I did my best to taste my own sperm, but it was still difficult to accomplish.
An insight into a crossdresser’s collection
Over the many years of crossdressing, and throughout the many purges of my things, I can still recall some of the highlights of my lingerie collections:
Frederick’s of Hollywood
- Shiny, silky garter belts with thick elastic garters – black, white, white with pink lace
- Lace garter belts – white, black, red
- Silky, shimmering hose – white, black, red, pink, pale blue, and nude.
- Lace topped stockings for garter belts, and with elastic tops as stay-ups
- Crotch-less black panties, white lace panties with blue tie bows on the sides
- Bras – black, red open cup, white with pink bows
J C Penny’s
- String bikini panties – pink, red, white, sheer red w/black lace trim
- Red lace garter belt
- String bikini panties – pink, red, white, sheer red w/black lace trim
Kmart, Target and Walmart
- Stockings – nude, black
- Tight black stretch low cut top
- White and black bras
- Black pleated short skirt
- Baby doll nighties
- Necklaces and brackets
- Clip-on ear rings
- Black/white plaid pleated short skirt
- Black snug Halter top
- Blouses – sheer pink, white cotton, sheer white
- Black A-dresses
- Black sandal spike heels
- Dark blue flats
- Lip stick – pink and red
- Eye shadow – silver
- False eye lashes
- Make-up remover
- Perfume – although I had to stop this as it was too easy to detect
- Condoms and KY jelly
Adult Book stores
- Magazines – cumshots, stockings
- Tapes and CDs
- Anklet socks
- Fish net and colored hose – black, red, white tights
- Vibrators – white, purple and pink hard plastic, flesh large “real” cock
- Sex dolls – I had three over the years
- Dog collar necklace
I would frequently wear sexy things under my business clothes when I went to evening functions. I could get away with panties, garter belts and stockings, but wearing a bra was tricky. I could do this only when I had on a winter coat, and or sometimes, even just a sport jacket. I would then sit at the desk in my hotel room, dressed, and masturbate while looking at porn. I enjoyed many rock-hard cocks and gushers of my cum!
I did go through my purging stages. One of my favorite routines had me leaving panties and such in the dresser draws, or under the bed, in my hotel rooms. Sometimes, I would stuff one of my plastic bags filled with lingerie in a hotel trash receptacle in a common area. I always regretted doing this afterwards, and within months, I would repurchase lingerie. The one benefit was that I did enjoy the shopping trips!
I wanted more. To be a real woman!
Real Life Story submitted by: Erica Lane
About the Author:Hi, I’m Marcy Simpson, founder and creator of Crossdresser Society. I have been a crossdresser for over 2 decades and I am also an author, photographer, entrepreneur, and admirer of the feminine realm. I currently work and live in Los Angeles, California.