Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a slim build, shaved body and long brown hair and eyes, with a 5 inch clitty cock.
I had never had sex with a man before, especially dressed up, or even really gone outside, but I did experiment playing with my ass with different home made toys like an electric toothbrush or part of a cucumber.
This time however I had gone to a city in the United States which was a fair drive since I lived in Canada. I decided to take my sexy clothes with me in an attempt to try to get fucked. I had kept my male clothes and sexy clothes separate in case I felt like surprising someone I had just met, and stored the two suit cases of clothes in my closet.
Once I was settled into my hotel room I couldn’t help but notice the large metallic pipe going from the ceiling to the floor. It was pretty clean but obviously not the pole dancing rod I had imagined, as I moved closer to touch it and see what it was like. As I moved my hand around it I felt how smooth and clean it was. I started to get sexy ideas as I grasped the big metal pole, slowly walking around it, dreaming of what moves I could perform in front of the big cock I would be bringing home.
As I moved my hand up and down once again I couldn’t help but feel aroused by the thought of performing for a hot guy, thinking of how I should move and what I would wear made me soo excited. I decided to get dressed and spend the day in my sexy clothes and wait till dark since I was still embarrassed about wearing feminine clothing. I decided to change into my black thong with pink mesh and matching bra with fishnets, before locking the door and laying in my bed and taking a nap before that night.
Once night came, I woke up instantly aroused from the thought of going out. My face turned red as I looked through my assortment of sexy clothing that I had brought. I decided to wear a sexy tube top that said "queen slut" on the front, a tight latex skirt that barely showed off the bottom of my ass, a thong and 6 inch heels to complete the outfit.
I couldn’t believe what I had chosen so easily as it seemed pretty slutty for going out, but then again I was looking to get fucked that night. I decided that since it was not completely dark out and it was still early I would get my courage up and walk to the sex shop just down the street and buy something erotic. Maybe an expensive dildo, or just a large one in place of the cucumber I normally used to masturbate, or maybe a vibrating cock ring to hold in my cum because I usually liked it when I came only using my ass instead of touching my little 5 inch clitty cock at all.
As I walked to the store I noticed people glancing over at me which made my face turn red. I couldn’t help but wonder if they were looking at me because I was dressed so slutty or if it was because they knew I was really a man.
Once I got to the store I walked in and closed the door. It wasn’t overly big, but it wasn’t small either. There were what seemed like thousands of toys and adult movies. I thought I must have died and gone to heaven.
I looked at some of the sexy clothing they had on mannequins. I had never worn too many roleplay outfits but I couldn’t help but think what I would look like in the sexy French maid outfit that was set up in the middle of the floor; it had always been my favorite roleplay. The thought of serving someone then servicing a big hard cock got me soo hot I could almost not control myself. I wanted to moan right there in the store and grab the closest biggest dildo and start sucking it, not caring who saw me.
I was barely able to control myself as I walked away from the stimulating French maid outfit and walked toward the toys I had thought about buying in the first place. There was a big white cock that had a suction cup to it and must have been 7 inches. I couldn’t help but think it was bigger than me and wonder how it would feel in my ass. I decided to buy that one plus an inflating butt plug and an extra large black dildo that was 10” long and maybe 3 inches in diameter.
I know you're not supposed to rush these things but I couldn’t help it, my lust took over my common sense. I kept my head down as I bought the toys and couldn’t help but wonder if the store clerk had noticed yet. After I bought my toys I went to walk out but I dropped my bag and had to bend over, revealing my ass as I picked it up. The store clerk whistled like “hey there sexy” and I was so embarrassed I ran out down the street back to my hotel room.
Once I had a few moments to relax I felt aroused and excited as I had noticed that it was now pitch dark out and time to go out on my mission for cock. Still in the same clothes, I decided to put on my black lipstick to help hide my identity. I grabbed my purse, with lube, some money and a flask of cherry whiskey.
I walked out of the room, locked my hotel door and started on my adventure of the night. I decided to walk in the opposite direction of the adult store and try to find a bar for someone such as myself. I continued to walk and saw another person dressed such as myself walking into a building that had a big sign that said “The Hole”.
My heart started to beat faster as I got up the courage and walked to the door. They asked for an entrance fee but other than that I was able to walk right in, seeing others such as myself dressed and some guys dressed in normal clothing.
After a while and some socializing and some drinks I decided to explore a little as I eventually came across a series of small cubicles, I entered one with some graffiti written on the walls. It wasn’t very big but seeing the giant holes on each side and on different heights I knew what it was and decided to lock the door.
I figured it was the perfect spot to start as it allowed for me to play with cocks and still let me do it in secret where I couldn’t be seen (as well as sucking a cock in a glory hole had been one of my many fantasies). I sat there with the clitty cock ring I had bought earlier and put it on, making sure I did nothing more then leak precum that night as it made me hot and so much more like a woman.
As I sat there with my clitty ring on I fantasized about what kind of cock would show up first and what hole it would come out of. I kept feeling like I was getting hard and horny but the clitty ring kept it down but made me focus on my ass more. I started moaning and kept standing up, sticking my ass out and slowly swaying it around, feeling naughty and sitting back down. I started to feel so horny as I waiting for a nice big juicy cock to come in. I started getting edgy, hoping, almost begging and screaming for someone to come in and let me suck him.
Suddenly I heard a click next to me and someone unzipping their pants. I couldn’t help but peek through the hole as I saw a limp dick that was a good 6 inches at least. He was not a super muscular man but who was I to be picky? I couldn’t help but notice by the way he was moving and rubbing his cock that he was trying to get hard, 'cause he wanted to have some fun as well.
Without thinking I said out loud, “I can help you with that.” He saw I was peeking through the hole. At first he was surprised he was being watched as well as I that I had said that. I felt embarrassed but soon he smiled and pressed his limp yet now semi-aroused cock through the hole pressing up to his thighs.