My Descent
by story1963writer
This is the first time I've told my story publicly. I wrote this maybe 3 years ago, and have shared it with one person.
I used to cross dress in my hotel room while away on business trips. I'm a fat bald 46 year-old who looks ridiculous dressed up in ladies underwear. When you're obsessed, though, appearances don't necessarily stop you from doing something. I'm married, but my wife doesn't know about my hobby. I never do it at home. It was something I only did when traveling. Fortunately, as a sales manager, I spent a lot of time on the road. But with airport security these days, it has become way too risky to carry a suitcase full of ladies undies and a dildo for pleasuring myself.
Even as a nine or ten-year old, I was the one who volunteered to play the girl role when we played games. Thinking back, it's funny how sexual some of our play was even though we did nothing overt, and didn't really know what we were actually doing.
I don't know how I got the idea to do it, but in high school, I began to dress up in my sister's or my mom's underwear and walk around in front of an open window. Then I would jack off. I don't think anyone ever noticed me. If anyone did, I never found out about it. My sister had a garter belt and my mom had this fabulous pink and black lace highly boned corset that I liked to wear. This was at the end of the girdle era. I carried on with this even into college, when visiting home for the summer. I stopped cross-dressing when I was caught by my father. I pleaded mental illness and he didn't punish me but he didn't try to do anything to help me either.
I saw my first picture of a transsexual sometime while in college. There was a spread in Hustler of a shemale. That wasn't revealed until the last photo of the spread, of course. I was absolutely fascinated. Yet men held no attraction for me whatsoever.
I had a roommate for the first year of college, during which my sex life revolved around masturbating to girlie magazines. Then I got my own apartment, and I made one of the great discoveries of my life. My anus. It welcomed many interesting objects ranging from vegetables to tools to furniture legs. My favorite was a hammer because the head was so heavy that I could squat over it and it would move in and out as I bounced up and down. At some point, the cross-dressing urge returned. I stole a few things from the washing machines in my apartment building. I went to clothing stores in run down areas of town where they would have big bins of panties on display and I would pick a few pairs and buy them. The anticipation, the planning, the actual selection of the panties, and bringing them to the counter to pay for them was painfully exciting, yet tainted by humiliation. In retrospect, maybe it was the humiliation that was the most exciting part of it.
I remember that I would walk past lingerie stores and admire the expensive satin and lace panties. They were so much nicer than the 99 cent, plain polyester panties I was buying. I had to own some. I staked out a store and went in as soon as the doors opened on some miserable Saturday morning, because I thought that was the time I was least likely to be seen. The owner greeted me nicely, and I asked her to show me some nice panties. She asked me what size my girlfriend wore, and I replied that they were for me. I shivered with delight as these words came out of my mouth. But the counter lady was appalled and she began to scream that I was a pervert, and I quickly ran out into the relative anonymity of the rainy street. It was many years before I went back to a lingerie shop.
I started traveling regularly for business in about 1998. I realized that I was totally anonymous in the cities I visited. I didn't know a soul. My hotel room gave me a place to be alone and uninterrupted. I started off traveling with one pair of panties. As the urge to dress became greater, I became more brazen and began to take more risks. I would go to Sears and buy nylons. I would go to the Maidenform outlet and buy panties. I was happy to learn that older sales help were respectful and served you without complaint. Younger sales girls are another story entirely. They laugh at you and sometimes make faces. I had no clue how to buy bras, so that was always interesting. They never fit. I would go to "Avenue" which is a "big woman's" store that sold lovely satin panties. I eventually acquired a garter belt and a Rado garter brief. I think I reached a point where I was carrying more lingerie in my suitcase than stuff for my business needs.
Upon arrival at a hotel, I would hang out the "Do not disturb" sign, lock the door, and strip down. I would open the curtains, pull out my lingerie, and dress up. I'd parade around the room, look at myself in the mirror, pinch my nipples, and begin jerking off. When I became aroused enough, I would lay down on the bed, keep pulling on myself, and begin speaking loudly saying things like "Oh, your cock is so big. Stick it in my ass. Fuck my ass. Ram it in me," in hope that someone in an adjoining room or in the hallway would hear me. This is how I would ultimately orgasm.
On one trip, while visiting the porn district, I just gave in and bought myself an 8" dildos with the rubber suction cup attached to the scrotum on the bottom. I was set. I fucked myself silly that night. I was afraid that I would become incontinent, I had stretched myself out so much. But ass muscles have a memory, and by morning all was right with the world.
Eventually, I was ready for the next step. It's not too hard to find ads for shemale or tranny prostitutes in most big cities. My first experience was Vancouver. The hooker had little tits, really smooth skin and was hairless from the neck down. I didn't know exactly what to do. I had never visited a hetero escort, let alone a transsexual, and I was scared out of my wits. Basically, I just lay there stroking this girl's thigh, looking at her uncut cock from a relatively close vantage point, but not daring to touch it. Eventually she asked if I wanted her to blow me. Her's was the first blow job that ever ended in my coming, even though I was covered. She gave much better head than my wife ever did.
Well, once you put your toe in the water, it's inevitable that you'll want to get fully immersed. I started visiting t-girl hookers wearing panties and stockings underneath my business suits. Eventually touching thighs went on to be touching tits and gentle carresses of the organ. Then the grip my obsession had on me began to strengthen. On maybe my sixth visit I finally took a cock in my mouth. It was one of the most exciting moments of my life. It was so much more fun than eating pussy, because you were able to see the effect of your work as that cock became hard in your mouth.
Then 9/11 happened, and travel with a suitcase full of stuff you didn't want to have revealed by the security agent wasn't so easy anymore. First I ditched the dildo. Eventually, I threw all my lingerie out. Since I never dressed at home, keeping it there just increased the risk of being found out. This didn't stop me from being obsessed with shemales, however, and I eventually knew that I was ready to lose my "virginity." It was with this ugly transvestite, again in Vancouver. She looked nice in the pictures on the web; a true testimonial to the skills of some glamour photographers. Well, despite her appearance, this creature had an incredibly seductive way of talking, and she suggested that we do all kinds of things, and the next thing I knew, we were naked and enmeshed. Her cock was small, and really wasn't all that sastisfying compared to that dildo I used to fuck, but my cock is pretty small, so I wsa not in a position to be that critical. In any case, it was nice to have something sliding in and out of my ass without having to provide the motion. I came.
Since then I have been with two more shemales. Once it was nothing special, but the other had fabulous natural-appearing tits and a huge thick uncut cock, maybe 18-19 cm long. I saw that thing and I immediately had to have it in my mouth. It was the first and only BBBJ I ever gave. She was a little rough, and she sometimes forced my head down on her shaft until I was beyond gagging. It gave me much greater respect for chicks and guys that can deep throat huge cocks in porno films. Well, I succeeded in my mission of making that tool hard, and she flipped me over, put on a rubber, greased me up, and plunged that monster into my ass. I thought I would die. I can't really describe the feeling but I'll try. It's like having to go to the bathroom for about an hour, but you keep holding it in and you feel that tremendous pressure building inside you waiting to be expelled, but kind of in reverse, and with rhythm. She did me for what seemed like 30 minutes, before flipping me over so that we were face to face, and finishing me with her hand simultaneous with her own orgasm. I came so hard I accidentlly squirted into my own mouth.
That was about 4 years ago. I finally understood why some men risk their life for the sake of a good hard cock in the ass. Common sense said quit, this is a dangerous game. I wish I could say that common sense was the reason why I stopped, but the real reason was that I didn't think I could ever have that intense a sexual experience again. Instead I began surfing internet porn sites of every imaginable sort looking for my thrills that way. I am a bit ashamed by what I have found turns me on, but then again, humiliation seems to be part of my sexual persona since childhood.
Prologue
On a recent business trip, I could no longer resist the old urge. I had to get fucked. I Googled "transsexual escorts" for the city I was visiting. The first escort I called sounded like a totally stoned junkie, with a deep man's voice. Not at all in keeping with the stunning picture provided. I found another ad for a shemale who looked pretty nice in the photo. You could tell the pic was real because she wasn't perfect. I could see that her boobs were silicon, and she had sort of a big ass, like a Brazilian, but her face was nice. I called her. She had a very feminine voice. I asked her if she was a "top." She replied "Versatile." After a few seconds she asked me "Do you want to get fucked?" I answered excitedly, "Yes." Then she asked if I liked to suck dick too. Again, I answered "Yes."
She said "Good." My cock was awakening and my heart began to beat faster. She said that she had a 7" long, very thick cock, and that some found it to be too big. I said that very big sounded very good, that I was ready to take all she could provide. We went through the usual negotiations, she agreed to come to my hotel, and I hung up. Maybe 5 minutes later, I called her back to call it off; I had chickened out. She made like she was very understanding and said "OK sweetie, maybe next time."
She may know me better than I know myself, because I'm already having fantasies of my next visit to that city, and of calling her again. But I think that next time, to help overcome last minute fears, I'll tell myself that I'll ask her to wear a condom when I suck her off.
If you like my story, please write me story1963writer at aim.com