I knew I was gay all through high school, but growing up in a town of eight hundred in West Virginia I never really had a chance to explore my sexuality with others. By the time I moved into the dorms at a small art school in Boston I was ready to do some experimenting!
My roommate in the dorms was another Midwestern boy who played lacrosse on the schools team. He was cute and a bit jockish but he seemed very aggressively hetero and I didn't really think he was the best person to come out to for the first time. After the first few days of moving in we settled into a routine where after class he would go to workouts and practice and I would watch DVDs or waste time on the internet before dinner.
I still had my old family AOL account and I would sometimes linger in the gay Boston chatrooms. Unlike home, there were a bunch of different chatrooms for gay guys in Boston, and I was amazed at how many men must be around the city. I started trading IM's with a man named Tennisfan36 who had noticed a picture of me on my high school tennis team in my profile. He asked what I was doing in the Boston room seeing that I live in West Virginia and I told him that I had just moved into town to go to college. He sent me a picture of himself and I must say that I was impressed with the way he looked. He appeared to be in his early 40s, wearing an impressive suit with a strong jaw and dark brown eyes. I thought he looked a bit like Pierce Brosnan.
After a few more minutes of chatting he asked what I was doing later that night. It was around 6pm and I was about to go eat dinner in the schools dining hall before coming back upstairs to watch TV. He asked if I would like to go get a drink with him at a bar near the school. I told him that I didn't have a fake ID and I'd learned that Boston bars are notorious for carding anyone and everyone.
Tennisfan36: If you dress hot and come with me, i can get you in
I told him I'd think about it and that I had to go get dinner, then I shut off my computer and went down to the dining hall.
While loading my tray with gross looking pizza and tater tots down in the dining hall I started to think about the chat. He really was amazingly handsome and I thought that he would be gentle with me. I had never done anything with another man and while I was ready to experiment I was still very nervous about my first time. I ended up throwing out the pizza without taking a bite and going back upstairs to my room.
Upstairs my roommate had arrived home from practice and was watching TV. I said hello and then nonchalantly opened my laptop facing away from him. I muted the speakers and logged onto AOL while pretending to watch an episode of Pros vs. Joes. Tennisfan36 was still online!
WstVkid: is your offer still good? Tennisfan36: absolutely, i know a place we can get a drink WstVkid: can i call you?
He gave me his phone number and I quickly punched it into my cell. Then I logged off and closed my laptop. I told my roommate I was thinking of going to see a movie and quickly slipped out of the dorm room.
Outside on the street I called the number nervously. Tennisfan36 introduced himself as Charles and I told him my name was Tim. He gave me his address and told me to just take a cab and call him when I got there, he would pay for it. I quickly flagged down a cab and nervously told the driver the address, I chewed my nails as we drove through the brisk Boston evening.
When we arrived at the red bricked townhouse in the Back Bay, Charles was standing on the curb looking dashing in a dark blue suit. He paid the driver and shook my hand formally introducing himself. I sort of blushed and followed him up the stoop and into his townhouse. The townhouse was a gorgeous three story affair with hardwood floors and cathedral ceilings. I was amazed at how expensive everything looked, Charles led me into the kitchen where he gestured for me to have a seat at the table.
"It's very nice to meet you Tim, I'm very happy to be able to escort you out to have a drink tonight."
"Thanks a lot Charles, to be honest, I've never done anything like this before." I looked down at the table sheepishly.
"What sort of thing? Be with a man? Or go to a bar?" Charles' voice was soft and reassuring.
"Everything actually. I've never been with a man, I've never been to a bar."
"But you are gay right?"
I looked up into his dark handsome eyes and felt myself flush with lust and attraction. "Yeah, I'm definitely gay." I smiled up at him.
There was a twinkle in Charles' eye. "Then I know the perfect place to go tonight!"
"Are you sure it will be ok?" Charles reached across the table and held my hand.
"Yes Tim I promise, you'll love it. Let me just go get changed." He stood up with me and kissed me lightly on the cheek which sent goose bumps all over my body. "Feel free to look around and help yourself to anything in the fridge, it will only take a few minutes." Charles left me and I watched him walk upstairs. I looked around the kitchen and then wandered into the foyer where there was a bedroom. Flicking on the lights I noticed the walls were pink and posters for the Pussycat Dolls and various bare-chested hip hop stars adored the walls. A pair of black pvc pants. I picked up the hanger and inspected the shiny material.
"You could probably pull those off you're so thin." Charles was standing in the doorway in jeans and a white button down shirt.
"You scared me!" I blushed " I wasn't snooping, I just didn't know who's room this was!" My cheeks were hot and I felt like I had been caught committing a crime.