"Like a virgin, touched for the very time..." echoes in the club as I'm pushed to the stage. At this point I'm beyond drunk and a couple friends have to hold me upright. My friend, Toni is on stage announcing to everyone that it's my 21st birthday, while pointing at me. More than half the people in this gay bar, in the middle of bumble fuck already know it's my birthday and that's why they are here. The few stragglers that had no clue, actually came over to say "Happy Birthday" and to buy "the 21 year old" a drink or shot. Like I needed more, but you're only 21 once. Why do people say that anyways? You're only any age once.
Most of the people at my party I knew from an online chat room called "Gay PA." (This is how I actually starting talking to my best friend James.) I had a WebTV back then. It was a DVD player-sized box that plugged into your TV and a phone jack to connect you to the Internet. I know it sounds retro and there was probably little gerbils inside the box, on a wheel making it work. WebTV had a remote control and a wireless keyboard you could use to surf around. It was perfect for chatting and for looking at nude pics of hot naked men in the middle of night while everyone else was asleep. I'm just saying, of course I never did that. (sarcasm)
Chat rooms were big back then and people from the Gay PA room occasionally all got together to party and to meet. I had met mostly everyone previously at a couple other events. The Gay PA chat room was actually my first real step into accepting myself as gay. I had people all over the state to talk too (most of them a lot older) and it helped to know I wasn't the only one struggling with their sexuality. It also helped I asked a lot questions about being gay. The older guys in the room took me under their fairy wings. Even though I hadn't known all these people long face to face, I chatted with them for months. I felt safe with these people. I knew their stories and for the very first time ever I felt accepted. They all knew me as the young, naive, nice, red headed virgin. Hence the reason "Like A Virgin" was playing. The guy I came with and who I was kinda dating, asked the DJ to play it.
As I sat there eating my red velvet cake that one of my online chat friends made for me, a very tall, very handsome man came up to me. I instantly knew who he was from the chat room. I have been talking to Alfredo for over a year, but since he lived in Erie (literally all the way across my state about 7 hours away.) I hadn't met him yet. He was around 29 when I first met him. He was very tall, but then again I'm not even quite 5'6 so everyone is tall. Alfredo had thick black hair and a nice lean, toned body. His background of course was 100% Italian, but unfortunately didn't have the accent. I only caught hints of it as he spoke. He looked very manly with his facial stubble, mustache and chest hair protruding out from the collar of his polo shirt. He was extremely polite and charming, which I assumed he would be from us chatting, but you never know. After opening my presents (Toni got me a pink kneeling pad she said I may need it some day. I actually still have it!) and tearful goodbyes we all parted ways.
2 years go by and yes I was still a virgin! Like some, I was waiting for the right one to pop my cherry. My mom like many mothers always said, "Nobody's gonna buy the milk if you're giving it out for free." I had only dated a few guys and none of them were Mr. Right. It felt like it was just a sea of men that wanted to hook up. Once they discovered it took a little more effort before I'd let them swim into my ocean (still does) they gave up the chase. I had this romanticized vision of how I wanted my first time to be, so I "saved it" like the Holy Grail! I didn't need to be in love, but I wanted to at least have some sort of emotional connection. I wanted to feel safe and look back on it fondly, not with regret.
Alfredo and I still kept in touch periodically through that two year span. His twin sister had moved out my way and he planned to stop by to visit me on his way back for a couple days. When I finally saw him again he still looked the same. Still tall, dark and handsome with puppy dog eyes and a beautiful smile. I had changed and he remarked how great I looked. I was about 110 pounds, tan, (thanks to the indoor tanning beds) with a nice six pack. (which showed because I was so small) I go-go danced at a bar in New Hope once a week and was a shooter boy the rest of the time. I may been naive when it came to the whole sex thing, but I had flirting with men down. Heck, that's how I earned my tips at the bar. Dancing on top of a box for 5 plus hours and working out every week did my body good. I couldn't put on weight to save my life but I was nicely toned. I was a Twink! A thin 26 inch waisted Twink! Alfredo was amazed by my transformation and he kept staring at me with a goofy smile.
Our plan for the evening was to go to the bar I worked at. It was a Sunday night and that was drag night. I worked there mostly Fridays and the occasional Saturday so I had no idea what Sunday's were like. Alfredo took me out for dinner and actually wanted to stay in New Hope. This way we could drink and not worry about driving all the way home. Plus at the time I still lived at home and he didn't want a bad first impression with my mom. There was a Best Western right before you actually got to the bar so Alfredo got us a room there.
The bar wasn't busy but I recognized a few faces. They came up to me to say hello and were shocked I had clothes on. After a bunch of vodka and Sprites and a few martinis mixed in, we stumbled back to the Best Western. The room was small. The bed spread had this ugly floral design. It looked like a florist threw up and the carpet was a dark navy color. There was a long dresser up against the wall and a TV sitting on top of it in the corner. It wasn't the fanciest room but hey it was a Best Western not the Hilton! I got undressed and climbed into the bed I remember I only had black 2xist briefs on. Alfredo had on a wifebeater and blue boxers. He cuddled with me and spooned me under the covers. I could tell he was turned on because it was poking my back. Alfredo was a very respectful type of person and I knew he never would make the first move on me.
I thought to myself, "Ok this is it! I've waited long enough. There isn't going to be anyone nicer than him. I've known him for awhile, I trust him and he is fucking sexy!" I rolled over so I was facing him. He pretended to be asleep already. "Stop pretending! I know you're awake" I said. He opened his eyes slowly, "Yes Kitten?" he replied. (Alfredo always had cute nicknames for me, Kitten was one of them.) I leaned forward a bit and kissed him. This was the first time we really kissed and his mustache tickled my face. I was trying to hold back a giggle. Once Alfredo got the green light his inner animal took over. My black briefs were taken off and thrown across the room to disappear into the darkness.
Alfredo's hot mouth felt great on my penis. He knew what he doing and he did it very well. He could have sucked the nails out of a board. I wanted to reciprocate, but he was more interested in pleasing me. He was right, he did actually get off more by making me squirm. Even though he wasn't into the whole anal sex thing we played "just the tip" he stuck his beef thermometer in just enough so I felt a sensation, but not in far enough to take my temperature. He had more fun digitizing my love hole than anything. Between the sensation of his fingers and him alternating between blowing me and jacking me off, I came all over my stomach. He finished himself off after watching me, then got us a towel. We got under the covers and he spooned me again. He whispered, "Sleep well Kitten" in my ear and I passed out.
I was hunting around the room for my underwear but couldn't find them. I picked the condom and wrapper off the floor, wrapped it in a tissue and threw it away. I didn't want the maid to get grossed out. Even though we didn't really have anal sex he still wore one to tease my hole. I looked around the room and saw a coffee maker next to the TV on top of the long dresser. I figured I'd attempt to make him coffee. It was of course the least I could do. He paid for the room, he blew me a few times. I owed him something. I put the grounds in the maker and poured the water in. When I flipped the switch nothing happened. "What the fuck!" I pulled on the cord and realized it wasn't plugged in. There was an outlet on the wall right behind the dresser. It must have been plugged in there. I grabbed the cord, but I couldn't quite reach the outlet so I attempted to move the dresser away from the wall a little. In my efforts, the dresser leaned forward too much which caused the TV sitting on it to fall forward. It was so heavy and knocked me on the floor.
There I was butt ass naked underneath a huge TV! I literally couldn't move! It had me completely pinned down and didn't even buy me dinner first! I didn't want to yell out in fear that someone else would hear me and barge into the room, you know like a maid or something. So I just laid there quietly waiting for Alfredo to come out of the shower. When he finally openned the door and appeared out of the corner of my eye he said, "What on earth are you doing?" I struggled a bit with the TV and said, "What's it look like? I'm making coffee!"
Having gotten to second base with a TV, my first gay sexual experience is one I will never forget. Alfredo and I hooked up a few more times after that whenever he came around to my area. I haven't seen him or heard from him in about 6 years though. The last time he was through I was dating someone else so we kept things on a just a "friend level." I liked the guy I was seeing and didn't want to mess it up. Plus I was starting to feel like Alfredo's out of town booty call. He was always very polite and very sweet. He never pressured me to do anything, but I wanted more and couldn't have that with him. The last time he was around my area I ignored the phone call.
To all the virgins out there: Know your limits and have a strong enough will to stop your partner from doing something you're not comfortable with. Some experts say that your first time actually sets the standard for your entire sex life. Hopefully it's one you remember fondly and not one you regret. By all means use a condom every time! If you are a late bloomer (like myself), try not to feel awkward. Hopefully your partner is sensitive to your inexperience and curiosity. If he doesn't seem that way then fuck him! (Not literally, get out of there!) You will most likely never forget your first time. I can still remember how his cologne smelt! Whether it's a hot one-night thing or the beginning of an ongoing relationship, you can still make the time sexy, fun and special. I hope that it will be a positive experience and you'll cherish the memory forever or at least learn something from it.
For more first time stories please see the post Touched For The Very First Time.
For tips on Anal Sex please see the post Bottomed Out.