Connie at an Adult Bookstore Ch. 01bycmorehead©
Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures.
Let me start by introducing myself. My name is Connie and I am a 40-something transgender woman. I live part of my life as a man, but I enjoy spending most of my free time practicing the art of female illusion. To me there is nothing more exciting than taking a long bubble bath, shaving from head to toe, carefully applying makeup, selecting the right outfit for the day/evening, and going out to take on a new adventure.
I first discovered the joys of cross-dressing in my early teens, trying on my sister's clothes and pantyhose. As I got a little older and moved on to college, I was able to explore my femme side even further. It was here that I started dressing completely and practicing with makeup. I also discovered my fondness for pleasing men and I was fortunate to have some great experiences in those four years. But college still didn't give me the complete freedom I needed to be Connie, so I couldn't wait to finish school and get my own place.
I had a job lined up when I graduated and found an apartment not too far from work. When I wasn't working, I was either out with friends or at home playing dress up. I tried to balance my social life with my time expressing my femme side. Sometimes I would spend the whole weekend dressed up and trying on different clothes. But something was missing from my life. I tried to date some of the women at work or someone I met at a bar, but it just didn't feel right. I realized I wanted to be with guys again, but I had no idea where to meet someone interested in a cross dresser. I had heard of a few gay bars in the area, but I was too afraid of running into someone I knew.
Then for some reason, I thought it would be cool if I got dressed and went to an adult bookstore. I had stopped by a couple bookstores close to the airport after I was out drinking with a group from work. Seeing all the magazines and sex toys was a big turn on. I was especially turned on by the gay and shemale magazines. This was before the internet became popular, so this was my only form of pornography to help me jack-off.
So one night I got all dressed up in a nice blouse and denim skirt. I did my makeup fairly sexy, but not too sluttish. My eye shadow was a couple different shades of blue, black mascara, black liner, blush, and pink lipstick. I wore some mid-heel pumps so that I could walk easily. I filled my purse with my makeup, drivers license, and some cash and off I drove towards the airport. I decided to try one of the cleaner looking ones first, so I pulled around to the side of the building and parked my car.
I took a few deep breaths, trying to calm my nerves, and looked in the visor mirror making sure my makeup was ok. I quickly got out of my car and entered the store. There were a few customers that acknowledged my presence, but they turned their attention back to the magazine racks. I started looking at the selection in the gay and shemale section, taking my time to find something interesting. I could feel my hands shake as I looked at the front and back covers, but I was also turned on. As I was looking around, I noticed a few guys entering and leaving the arcade area. I had checked it out once, so I knew there were movies back there, but I was too nervous to watch them. The whole idea of entering a booth was a little odd to me at the time.
After choosing a couple of magazines for my reading pleasure, I went up front to the clerk to pay for them. He was a middle aged man who just smiled and asked me how I was doing. He put my magazines in a brown paper bag and asked me if I needed anything else. I wasn't quite ready to go yet, so I decided to get some tokens for the movies.
I walked to the back of the store and entered the arcade. I had to let my eyes adjust before looking for an open booth. As I walked up and down the aisles, I found most doors were closed and there were a few guys just standing around. I finally found an open booth and went inside, locking the door behind me. The selection of movies included straight, group sex, oral sex, gay, and a shemale movie. I deposited a few tokens and chose the shemale movie.
This was the first time I had seen anything except a straight porn film and I was really enjoying it. My dick was starting to get really hard inside my panties. After watching the movie for a few minutes and rubbing myself, I pulled up my skirt and pulled down my pantyhose a little. I continued to stroke myself through my panties and was really getting into the movie.
It was pretty dark, except for the light from the movie, but I thought I noticed something on the wall about waist high. I got a little closer and realized someone was poking their finger through a hole in the wall. I had no idea what a gloryhole was, so I bent over for a closer look. The finger disappeared, so I looked through the hole and saw someone on the other side watching a movie and stroking their cock. I was mesmerized so I just continued to watch the show they were putting on. He must have seen me looking through the hole, because he bent over and whispered something. I couldn't understand him, so I backed up a little thinking I made him mad. Then I couldn't believe what happened next. I saw the head of his penis come thru the hole and stop when there was five or six inches on my side. I didn't know what to do, so I started to fondle his cock. He seemed to enjoy it and start to get harder as he moved it back and forth.
Then he pulled all the way out and I was wondering what happened. I looked through the hole again and this time he bent over and whispered, "Suck me, bitch!" Soon his cock reappeared, so I got into a crouching position and placed my mouth on his dick. It had been awhile since I gave head, so I savored the taste and ran my tongue all around the head. I could feel the cock grow larger in my mouth as I sucked on the entire shaft. My legs were starting to hurt after a short period of time, but I was really enjoying myself. I made the mistake of getting on my knees at one point and felt something wet soak into my hose.
It felt a little awkward only being able to suck part of his cock, but I continued to do the best I could. Normally, I like to lick and fondle my partner's balls, but I was just happy to be giving head again. Then without warning, my anonymous friend thrust forward as much as he could and erupted in my mouth. He shot a few times as I continued to suck, but I was careful not to swallow. When he pulled out of my mouth, I spit out a mouthful of cum onto the floor. I looked through the glory hole briefly and saw my new friend zip up his pants and leave his booth. I sat there for a few minutes, kind of embarrassed and just trying to take in the whole experience. Then I grabbed my magazines and purse and left the arcade area. I quickly walked to my car thinking everyone in the place was looking at me.
As I drove home I noticed the dried cum stains on my pantyhose and it made me feel all sexy and naughty. I had a hardon and was still feeling very horny. When I got home I spread out on my bed and masturbated until I fell asleep. I awoke the next morning thinking about my first time in an adult bookstore and I couldn't wait to go back!
To be continued...
I hope you have enjoyed my early attempts to share some of my memories. Feel free to leave a comment or send me an email.