I had been crossdressing alone for many years but always in the safety of my own home. But I had always wondered what it would be like to actually meet with a guy. I had fantasized about how much I needed this and I had spent hours and hours watching videos of crossdressers pleasing sexy men. Now, the time was coming for that first adventure.
My wife knew nothing about those secret sissy desires, to dress as a sexy woman, to meet a sexy guy with a hard cock, and to please the lucky guy. So, when my wife was going on a 10-day cruise with a couple of girl friends, I knew this was the chance to do the things I dreamed about.
After driving my wife to the airport, I drove the hundred miles back to the small farm town where we lived. I had been collecting my sissy clothes for years: wig, makeup, sexy high heels, pretty dress, everything I needed.
I spent the next day shaving my entire body and getting my stuff laid out for the after-dark trip to try to meet someone. Just the act of shaving my legs was enough to make my cock rock hard. I really needed to do this.
As night came, I did my makeup, going as slutty as I could, with a lot of time spent doing my eyes, like the way that I had seen in the videos. I applied some long sexy eyelashes, then blended in my blush to my cheeks, then some bright red lipstick.
Feeling very satisfied, I slipped my wig on; it was medium-length brunette with cute bangs. Looking in the mirror I thought I looked very sexy. I decided that I would wear a pair of sexy black crotchless tights, a pair of sexy 5-inch heels, a black bra, and a sexy black mini dress with full transparent sleeves.
I checked myself in the mirror, wondering if I should actually go out in public like this. I was close to chickening out when I realized I had been building toward this adventure. So I carefully went out to the car, again thinking that I didn’t have to do this. But I knew, deep down, I had to, I needed to be someone’s slut, pleasing them with a nice blowjob, just like in the videos.
The closest spot around was 20 miles away at a rest area on the Interstate, a place that was on a list of gay cruising areas. As I drove, I admired the way my legs looked in the tights, the way the high heels felt, wondering if I had the nerve to get out of the car once I got there. I wasn’t sure.
I pulled off the Interstate and past all of the big trucks to the far end of the lot, away from the main bathrooms. I stopped the car and just sat there. Finally, once I decided there weren’t any other people at this spot, I cautiously got out of the car. The feeling of the cool air on my legs, the excitement of doing what I had dreamed about, was fantastic.
I walked carefully to one of the paths that ran to the various picnic tables. This was my first time dressing this way, in public. I enjoyed walking around, hearing my high heels clicking on the sidewalks. I hadn’t seen anyone else at this end of the lot but I could see people using the main restrooms and drink machines.
I walked closer to that area, leaving the safety of my car. Nobody had noticed my presence so I was emboldened to move closer to the soft lights.
Just then, a nice looking guy came up from one of the viewpoints and stopped right in front of me. I was startled by his sudden appearance and he apologized. I forgot my feminine voice when I said it was OK. He just looked at me and smiled.
He asked if I was on my way to a costume party and I decided that was a good excuse for my appearance. He told me I really looked good, very hot. I blushed. We exchanged some small talk and I was feeling fairly calm in the situation.
He was about to leave when I just blurted out that I wanted to suck a nice hard cock. He stopped, looked at me and just asked, “Really?” I nodded and told him I had dreamed of this for a long time.
He gently took my hand and led me down the path to one of the picnic tables and told me to sit down. I did as he instructed and he slowly let his jeans open to expose his very sexy cock, slowly getting hard right in front of my face.
He stepped forward and I found myself kissing the beautiful mushroom head, like I had been doing it my whole life. I let his warm cock slide into my mouth, enjoying the fullness as it filled it. I started sucking slowly but I was soon going faster and faster. I had bought some cream that deadened the rear part of my mouth, something I had seen advertised to prevent gagging. It was working as his cock went deeper and deeper into my throat until I was taking the entire length.
I could feel my sexy partner getting ready to cum, and he pulled his cock out just long enough for me to tell him I wanted to swallow his hot load of cum. He just smiled as he pushed his cock back into my mouth and told me, “OK, slut, here it comes, eat my cum, eat all of it.” He stiffened, his cock perked, he moaned, and suddenly I was awarded a huge load of his cum. I continued sucking him, trying to get every drop of his cum out of his cock.
Afterwards, as he pulled his jeans up, he said that was the best blowjob he had ever had and he thanked me. I felt so feminine as I sat in front of him. He pulled me to my feet and gave me a nice hug and I found myself needing to kiss this guy. He leaned forward with his lips inches from mine and we gently kissed. I felt so sexy, knowing I had pleased him as the woman I had dreamed of being.
He said he needed to get back on the road but he had loved the experience. He asked if I would want to meet again and I told him that would be fantastic. He said he drove this route every night and usually stopped while going through. I told him I’d see him the next evening. He took my hand and led me out of the darkness and out towards the parking area.
I watched him climb into his truck and leave. I had lived the dream, I was a sissy slut, willing to suck cock with a stranger. As I started to turn to go back to my car, two guys approached and one of them said they had accidentally seen me sucking cock.
One of them said it was extremely sexy watching me and it was too bad they had missed out. I don’t know what happened but I found myself asking if they wanted me to suck their cocks too. They looked at each other and said, “Sure.”
We went back to the picnic table and I just asked, “Who’s first?” I was soon sucking one of them while the other watched as I pleased his friend. When I finished with the first one, the second guy had me lie across the table on my back with my head hanging over the edge. He slowly pushed his hard cock into my mouth and started fucking my throat. He was pushing his cock deeply into me as he moaned about how good it felt.
The first guy was near my feet across the table. He gently stroked my legs as he lifted them up and asked if he could fuck me. My mouth was full, so I just helped him put my legs over his shoulders. He slowly pushed his cock into my well lubricated bottom. There I was, being fucked from both ends, enjoying the attention of 2 guys that knew what they were doing.
As they both finished by filling me with more cum, I noticed that we had an audience. There were 4 other guys watching me get fucked and I found myself inviting them to join in. I let them fuck me or suck me, whatever they wanted to do.
I drove home thinking about how it felt to be a real slut, filled with cum, pleased by what I had done that night. I’d be back for more the next night. I am a submissive cum slut and I want more.
