My First Cock

This story is my first experience with a man dressed up as Monica, my slutty alter ego.

Like, most Cross Dresser’s, I started young. I grew up with plenty of women, all family members, and I remember trying on panties and strutting around at a very young age. I especially, liked wearing my Aunt’s business suits, women in business clothing has always been hot for me.

However, like most things with kids, I stopped dressing and moved on to something else. I wasn’t embarrassed or anything, I just “outgrew” it? I starting growing up and doing what young guys will do, drinking and chasing after girls, I lost my virginity and just loved sex! I had has much as I could, with as many girls as I could but soon another craving came about. When the urge came and I was alone jerking off, I had feelings of wanting to be the girl in the porn video.

Dressing sexy and slutty and being the object of some strong man’s desire. The urge came and went and since I was in high school at this time, I started sneaking my Mom’s clothes again but I never acted on my fantasies.

The school years went by and I got accepted to the college of my choice, I was excited to be away from home, I was told it would be a an awesome time for me, my uncle’s kept telling me about all the “awesome young pussy” I’d be getting and I wanted it too but there was something else I wanted as well. Just thinking about it now, I get a snug smile. The secret whore within that was yearning to be free.

My freshman year started and I was instantly overwhelmed with school and life, before I knew it, I had tests, and study groups, and dorm drama to deal with and if you’ve ever lived in a dorm, there’s plenty of drama!

I was having the time of my life but because of my lack of privacy I had to hide my urges, I took a pair of panties from a friend of mine as she moved out mid-semester, she’d had to leave school for “family reasons”, the black bikini bottom, was brand new, it still had a tag on it! It was the least of her worries and even though, I should’ve felt bad, Monica needed something to make her feel sexy!

I put them on most nights after that; they were smooth and very comfortable. I would rub myself under my sheets at night, I was scared that my roommate would catch me but after I got those panties, something had been released and I couldn’t contain it. I made the decision to buy more and to eventually play out my long time fantasy of being with another man.

I bought more and more clothes, a skirt here, a blouse there; I was even able to find a wig with black streaks in it. Monica was getting closer and closer to her first night out.

As the year drug on, I started strolling online looking for a hookup. Was it the best way to go about it? I don’t know but I knew that I wasn’t ready to just go out dressed up. Eventually, I found a nice enough man; we met through an ad I had placed on one of those classified pages. We started to email each other on a semi regular basis. He said his name was Tom, I never did find out if that was his real name, he was an accountant in a small firm in town. He was in his mid-forties and said he’d always been interested in a CD, I told him that I’d always been interested in hooking up with a man.

The emails continued. They were usually short and perhaps a little naughty, always asking me if I was wearing my clothes, I would lie and say yes. I did however, dress up one day to take a pic for him, I asked to exchange pics and we did, he was a handsome man, with salt and pepper hair and broad shoulders. After I saw a picture of him, I told him that we had to meet; he said that we couldn’t meet at his house. I wondered if he was married, it didn’t matter, Monica wanted him.

We agreed to meet at a hotel on a Friday night; it gave me a week to get ready. I told him that I wanted him to come in his work clothes, a business suit and that I would be dressed as a slutty secretary, he LOVED the idea. I had my work cut out for me, I searched the local thrift shops, after all, I was on a freshman budget. I found the outfit, a short black skirt with a red satin top and a blazer. I went to the local adult shop and got stalking’s and fuck me heels were surprisingly easy to come by. As I tucked my outfit away in my closet, my anticipation grew!

That Friday, was one of the longest of my life! I skipped my classes to get ready, I shaved and made sure my body was smooth. I practiced my best girl’s impression and I tried to keep myself from cumming every second, but it was hard! Pre cum hung on my cock, the entire day.

Finally, the night came. It was dark and for the most part, it was an average Friday, kids running everywhere getting ready for a party or whatever. My plans were slightly different; I would go to a local park to change in one of the bathrooms and then drive to the hotel. It was dirty and I liked it!

A while later, I peeked out of a dingy bathroom, overlooking a hopefully empty park, I quickly made the walk, even though I was scared, the thought of getting caught made me excited and horny, I imagined what I would say to local or even a police officer, “Please sir, what can I do so that I can go on my way?” I was a slut for the night and I loved the thought.

I made it to my car, just a little disappointed. I instantly got excited again as I looked in the rearview mirror, I was Monica, a slut with a itch that needed to be scratched!

The time flew by and soon I was knocking on Tom’s door, he opened the door and I walked into a semi lit room, he wore a simple black suit, he was about six feet tall, with dark green eyes and short salt and pepper hair. He was in shape and you could see it in the way his clothes fit. “Monica?” He asked. “Do you want a drink? I was sipping on Tequila.”

I was instantly glad he’d said that! “Yes. Please, two shots.” I said back. I was all of sudden a little nervous and I hoped the Tequila would soothe my nerves. He handed them two me and in a moment they were gone and so were my inhibitions! My body got warm and I started to walk over to the bed. I called him over as I crossed my legs.

He sat down, with an awkward smile. “Nervous?” I asked giving him a reassuring smile. “Yeah, a little bit.” He said laughing. “Is it that obvious?” “A little bit.” I whispered softly. I was nervous and overwhelmingly horny. We were like two teenagers not sure of what to do. I smiled and I started to slowly caress his leg. He held his breath as I got closer to his package, I gave him a squeeze and he exhaled. “Kiss me, Tom. Kiss me now.” I said.

He leaned in and soon we were kissing, slow at first but soon, his instincts took over. He darted his tongue in and out of my mouth. His scent was manly but clean. I could feel the stubble from his five o’clock shadow as our tongues began to wrestle. Then suddenly, he was over me. My skirt was hiked up and my neck was turned, his strong hands were all over my body and my legs, touching and squeezing. He pushed me down and put my hand together over my head. I was in heaven!

“Yes, Tom! I’m yours, take me, fuck me!” He kissed me all over and then sat up, I was upset that he wasn’t on me but he was taking off his shirt. I sat up and started to help with the buckle. His cock fell out in front of me and I worked his pants down. It was big and cut; it throbbed as pre cum slowly dripped out.

I grabbed it and started to stroke him. He moaned and then I had him in my mouth. I started to moan loudly as I worked his shaft. He moaned loudly. He pushed me off and held on to my shoulders as he lowered himself down onto the bed. I crawled down and got in between his legs. I started to stroke his cock with both hands. His breathing got heavier; I started to suck him off. Short strokes and then started to take him in deeply into my mouth. His cock tasted great, I would look up and I could see him moaning. As a slid him out, I would twirl my tongue around his head. He grunted and put a pillow over his face. I got up and I could see him pushing the pillow into his face, I grinned wildly. I was Monica, brand new cock slut and this man was putty in my hands!

I lost all abandon and went back to work on his shaft, bobbing furiously on his cock. I twirled my tongue around his cock head, as fast as could, his body started to shake! Both of my hands were on his thighs, I kept licking his head and then taking the length of his cock, then his toes curled and his legs, tightened, he shot a load into my mouth. I was stunned but I swallowed all of it. It was salty, but it was my payment for a job well done. I sat up and cleaned around his now limp cock with my tongue. I looked up and saw him looking at me, was too shocked to say anything. I smiled and gently kissed his cock. I slowly slid up to his mouth and kissed him deeply.

He breathed heavy, “Wow, Monica, that was, that was wow!” He said.

I put my fingers to his lips, “Sshhh, baby, take it easy. I’m expecting a round two…”