How I Became a Crossdresser

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I’ve always loved everything about women. I love their curvy feminine features, their long painted fingernails, the high heels they wear and their silky smooth clothing. When I was young, I liked the women I dated to be flashy and slutty looking. I never had much trouble getting the sex I was after from these women either.

I got married in my late twenties. In spite of the fact that my wife and I had a great sex life, I always seemed to have a woman on the side in those early days of my marriage. I just couldn’t help it. I loved women and sex too much to turn down an opportunity for sex with the pretty coworkers that would come and go to whatever factory that I happened to be working at.

Then around the time I was 40, my wife reached menopause and her interest in sex completely diminished. After a couple months of celibacy I was really sexually frustrated and needed some relief. Not wanting to start up with an affair I turn to online chat rooms for help.

One thing I found out right away is it there’s not too many women showing skin on online chat rooms. There are however many rooms dedicated to just crossdressers. Pretty, frilly crossdressers too, looking more feminine than most women do. I found their strip teases on cam to be great masturbation aids.

Then one night it was dead in the chat room. No crossdressers just a bunch of horny guys strokin it on cam. I saw my wife’s nail polish on my desk and decided to liven things up a little bit. So I painted my toenails on cam. The men in the room went crazy. So many of them were trying to watch my webcam that it temporarily crashed my computer.

When I logged back on, I limited the amount of viewers and proceeded to paint, wiggle and move my toes and feet. My viewers started shooting off their hand cannons like a 21-gun salute. The whole experience had me aroused like never before.

Now up until then I never had a gay thought in my life. As a young man I had more than one offer to do something with a guy (teenage sleep overs, roommates etc.) and I always ran from it explaining to whoever was pursuing me that I just didn’t swing that way. So I was surprised at how hard my cock was from me watching other cocks shooting off due to my body, actions, and words. Surprised or not I was addicted to it after the first time I did it. I kept going back to the chat room, more of me showing each time I started my webcam.

Since my feet were so popular, I started with toe rings. Next it was pantyhose. Of course I shaved my legs so they would look good on cam. Anklets and high heels purchased on line topped off my leg show accessories. After about a month had passed there was a sexy woman looking back at me on my webcam image I couldn’t believe it was me! With a wig, earrings and makeup I actually looked pretty damn sexy. What really seemed to motivate my efforts though was that I had a following of men who were crazy about my webcam shows which I was now doing almost nightly.

Two things bothered me at this point. I worked swing shift so my wife was sleeping upstairs while I was doing my chatroom show. I figured it was just a matter of time before she woke up one night and caught me with my panties down. The second thing that bothered me was how obsessed I had become with cock. Seeing such nice ones nightly I now wanted to suck one and make it explode in my mouth so very badly. And I wanted to do it as my female self only. It was all I could think about. That’s when I got an idea.

I had never been to an adult theater or bookstore. In fact I had only recently read about what went on in them. But I knew there were a couple of them between work and home. Furthermore I shut down the plant I worked at on denizli escort Friday night and I was the last to leave the building since I was the shift foreman. So I made up my mind. I decided to make my first visit to an adult theater as a woman.

I packed a gym bag with my shortest skirt, highest heels, makeup and accessories and put it in my car that morning. Later that night, after the last employee clocked out and left, I ran out and grabbed my bag of goodies and brought it back into the plant. I decided to change in the women’s restroom because the mirror was bigger and the lighting was better. After about an hour I was ready and very nervous.

My high heels clip clopped down the long cement hall as I walked towards the employee exit . It was the farthest I had walked in heels and it was not easy to do. I found that I had to keep it slow and steady. No fast walking for me at least not yet. I cautiously peeked out the door. If even one coworker saw me in my female form I would just die from embarrassment. After seeing that it was clear, I turned on the burglar alarm and walked to my car. As I drove to the adult theater my nervousness worsened with every stoplight I stopped at. I pulled into the parking lot and turned off my headlights and engine.

As I glanced around the theater parking lot I saw several cars were occupied by men. A man in a nearby car had seen me and was staring my way. I wondered if he could tell from that distance, in the dark that I was really a man or if he even cared. After all men come to places like this most likely because they are single, or in a sexless marriage. They are there to receive a hand job or blow job from another man. However 90% of them would prefer a woman and are just settling for what they can get. Someone like me is definitely going to be an added bonus. When he opened his car door and started walking towards my car, I lost my nerve, started the engine and got out of there!

Well I was very disappointed with myself as I drove towards home. All that anticipation, an hour getting ready and I chickened out. What a disappointment! I stopped at an RTD Park and Ride and before changing back into my men’s clothes and I took some selfies. I love my fem photo collection of selfies. That made me feel a little better before going home empty handed.

The next Friday I did the same routine again but I smoked some weed while I put on my makeup in the women’s restroom at work. I was much more relaxed but really got carried away with the eye makeup. I had also bought some glue on french tip acrylic nails which I meticulous glued on each finger. They looked great when I was done and I found their semi-permanence very arousing too. By the time I was finally ready it was about 90 minutes that I had been dolling up putting the time around 1:30 am as I drove towards the theater.

There were less cars in the parking lot than the previous week but I could still see that several vehicles had men sitting in them. I felt that nervous feeling coming on and I parked fairly close to the entrance this time (the week before I was a ways from the entrance). Stalling I looked in my visor mirror, applied a fresh coat of lipstick and gloss to my lips. I then put some cash in a small handbag along with my ID and the lipstick. Taking a deep breath I stepped out of the car.

I was so nervous it was hard for me to breath. It felt like there were 100 eyes on my backside as I walked to the theater entrance. I am 6′ tall without heels so I am sure I looked like a man in drag with great legs, entering an adult theater at 2:00 am on Saturday morning.

I went to the ticket window and although I wanted diyarbakır escort to use a gurly voice, words came out in a rather deep voice. “One please” I said. The man asked for my ID, looked at it and then me, rolled his eyes and explained that I could go in theater

for $8.00, straight porn only. $13.00 for all 3 theaters included the
theater that only played gay porn. I paid $13 and went to theater

I found a seat near the center of the theater and sat down crossing my legs, skirt hiked up towards the main aisle.

I was probably there 30 seconds when a handsome young man asked if the seat next to me was taken. I said no, sounding very girly this time and he sat down next to me.

He asked if I wanted to make out with him and I said yes.

It felt weird and different at first to feel his rough razor stubbled face against my fresh, smooth makeup covered cheeks as he kissed me passionately. I got over the weirdness quickly and was immediately overcome with lust! He unbuttoned my shirt without me even noticing and sliding a hand into my bra cup, began fondling my boob and pinching my nipple all the while kissing my face and lips like an animal.

My right hand found its way to his crotch and I started rubbing his already hard member through the pleasantly thin material that his slacks were made out of. My fingers found his zipper and as I went to pull it down he stopped me saying that we should move into a booth.

“I didn’t know that there were any booths here” I told him. He explained that they were on the bookstore side of the building and we would have to completely exit the theater side, go outside, around the building, and back in on the bookstore side. I agreed to follow him.

I got some looks from both men and women customers as I walked through the well lit bookstore. Women usually giggle, laugh or smirk when they see me dressed. Men either look at me lustfully or hatefully. Being tall with masculine features and new at walking in heels I did not feel passable or comfortable in this public place on my first trip out as Chrissy.

I was trying to keep up with my new found stud as he walked towards the arcade sign in the back of the store. I followed him into the 2nd booth from the left and we began making out passionately like we left off back in the theater. It was much better being face to face. As we kissed he expertly stripped my clothing off and within a matter of a couple minutes I was down to bra, panties, thigh high stockings and heels and he was still fully dressed! He pushed me down into a metal folding chair that was in the booth and then took a coke vile out of his shirt pocket and held a big spoonful in front of my face. I snorted it like a good slut should always do. Then he did one and we both did one more. After that he positioned his crotch in front of my face. I could see the outline of his hard penis pressing against his slacks right in front of me and I knew what I was expected to do next.

I unzipped his pants and to my surprise he wasn’t wearing underwear. So I carefully pulled his hard on through his fly. He had a bigger cock than I was expecting. It was much thicker than mine and about 7-8″ long. I was thrilled with his beautiful tool and proceeded to make love to it with my lips and mouth.

When I needed to catch my breath I would lick up and down his shaft and then finding the tip of his head with my tongue I would commence to sucking him as far down my throat as possible. He started to breathe heavily and that’s when I realized that he wasn’t the only person that I could hear breathing heavily.

That’s when I saw, out of the corner antalya escort of my eye, I saw someone watching through the gloryhole from the next booth over. I wasn’t able to do or say anything after that moment though because my handsome stranger grab the back of my head and really started to fuck my face with vigor. He got a little bit rough with me but I really liked it even though I gagged a couple times when his nice big cock would hit the back of my throat and trigger my gag reflex.

I felt him swell in my mouth and he began to moan. I knew he was close. I took a deep breath before taking as much of his shaft as possible into my mouth and stopping once his puvic hair was tickling my nose. I held my mouth there on the base of his shaft for a couple seconds. That was it! He grabbed the back of my head even tighter and closer to his crotch than he was already holding it and began shooting his load in my mouth. It was such a wonderful feeling as his cock twitched, drained, and slowly went soft in my mouth while he held the back of my head the whole time not wanting to let go until he was completely drained.

I was so proud of myself! I finally had sucked a man’s cock to completion. And it was a beautiful cock attached to a handsome man at that, all while I was dressed like a slutty woman. The best part of course was that I successfully made him cum. Of all the blowjobs I had received from women over the years, only about 30% of them resulted in an orgasm for me. Only the orally talented women I had known had done that to me. So I thought to myself, “You’ve got skills girl!”

He then thanked me, zipped his pants and exited the booth quickly.

I was still catching my breath in my panties and bra when to my surprise, the door opened. There stood a bald, pudgy, not so handsome man with his hard dick in his hand and a smile that looked somewhat evil on his face.

He locked the door behind him and moved towards me. That’s when I realized that he was the guy who had been watching through the gloryhole. Well sitting there in my panties and bra with a man that knew I was a cock sucker waving his hard penis at me, I didn’t feel I was in a position to resist anything he wanted from me. I had no choice but to suck his cock now too.

I don’t know if I was real horny, real high, or turned on by the fact that I kind of had no choice but to give this unattractive man what he wanted. But this guy had me even more turned on than the first guy. I think it was the forced factor personally but all I knew was I needed him to fuck my face now! My own dick was harder than I have ever felt it and I thought I might cum without even touching it.

I took his cock in my mouth and went up and down on it sucking and licking it like a hooker with my newly trained hot little mouth. He came within 3 minutes and I gulped his cum down like it was maple syrup.

Then he got on his knees, pulled off my panties and sucked me right in that chair. I wrapped my legs around his waist and pulled him into me while he sucked me with a mouth that had definitely sucked a cock or two before.

I came real fast due to his expert abilities and my own state of mind. Like the first guy, he exited the booth rather quickly after putting a smile on my face. I then got dressed too and left the booth.

It was almost 3:00 am when I got to my car and there were only about 3 or 4 more cars left in the parking lot. My make up was smeared and I looked like some of the women I used to pick up at the club when they woke up in my bed the next morning. I took off my makeup while driving home. I changed in the garage and managed to sneak in my house without waking my wife and crawled into bed without getting caught.

It was the first of several Friday night, adult theater adventures. The week after I was almost gang banged by a group of men in the theater After escaping with my virgin flower unscathed my wife was awake when I tried sneaking in the house with all my female attire still on my body. But that’s another story.

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