Virginity

So something I’m sure I lied to many people about was the first time I inserted my penis into a woman’s heynanunanu. The year was 1995 and I was on Spring Break in Cancun, Mexico. I was 18 years old and a freshman in college. I went with 4 or 5 guys I just became friends with at college and one of them Glen(who is still a good friend, good dude) invited 3 guys and 3 girls from his hood, which is East Boston.

I remember arriving at sunrise and walking with Pete, who was my freshman year roommate, to the nearest seller of corona. We bought a case and the owner asked if we wanted to use his bottle opener to pop one in the store, this was the first thing I did in Cancun…fucking awesome….and I’m 18!!!! We walked back to our hotel corona in hand and watched the sunrise, got drunk and went to bed. After waking up the day was somewhat of a blur but I do remember going to the hotel pool and noticing that one of the girls who came with us, I’ll call her Kate, had her nipple skin peeking out of the side of her bikini top. The weird thing about this is that her nipple skin(I think its called areola) were huge, the diameter must have been about 5 inches, if her bikini top moved at all it was showtime. It was truly amazing, I wish I could draw you a picture. Anyway, after that we walked the beach and I remember one hotel had tequila volleyball in their pool, its basically volleyball with a guy pouring tequila in everyones mouths. Really fun stuff. Thats all I remember about that day. Now to the Night.

This night is one of the funnest times I’ve had. All 8 to 10 of us first went to a small bar/club where not many other spring breakers were at. We started drinking and dancing and just having a blast. Glen was throwing his money around and actually ended up renting a random local mexican guy for the time we were at this one place. That actually sounds kinda creepy and almost wrong but it just consisted of the guy dancing with us jumping in a small creek of water running through the club and having a good time. I don’t remember that guys name but I loved him. Next we went to a bar called Carlos and Charlie’s(I think), It was like walking into a movie, everyone was dancing and drinking. People were on tables, everyone was so happy and friendly, it was amazing. I wish I could explain in words the beauty of my dance that night but it is impossible. I ended up dancing with one of the girls that came with us to Cancun, I think her name was Shannon. We danced for a while and ended up making out. It must have been my awesome dancing that aroused her. Hours later we all started walking back to the hotel and Shannon came back to my room. Now let me explain the setup of out hotel room. When you walk in there is a bathroom to the left and a kitchen to the right, straight ahead was 2 steps down to a square room with beds/couches on each of the walls except the wall straight ahead that was a sliding glass wall to the outside, right on the beach. There was a master bedroom on the right of this room(right if you are facing the window to the beach), the master bedroom had a half wall, so if you stood on one of the beds in the other room you could see into the master bedroom. Ok I hope thats not too confusing, the one thing I’m trying to say is that the master bedroom is not private, but back Shannon.

We got to use the master bedroom because we are hooking up. We start kissing and such, I start taking off her clothes. At this point I’m scared, I mean real scared, I’m a virgin for Christ sake. She starts giving me pleasure(maybe for the first time, I forget, but probably, damn thats sad), I start going downtown, I could have been licking the bedsheets for all I know. Then I start hearing giggling from my friends who are peeking over the half wall. I guess they didn’t know this was going to be the wonderfully special time that I lose my virginity. After a few minutes I start negotiating to myself if I want to be a virgin anymore. I could abort mission right now. But I was already embarrased enough that I was a virgin at 18. It seemed that noone I knew was a virgin, either that or they were lying like I was. I decided it was man time. I needed a condom. The only one I had was a condom that was in this keychain I carried. I don’t think it was supposed to actually be used, I think it was kinda like a joke keychain, break in case of emergency sort of thing. I ran naked in the other room(where it was), my friends probably saw me but I forget. I applied the Condom and proceeded to have some bad sex. I don’t remember too much about the actual poking, but it seemed like she liked it, which is cool. Now here is another mini confession in this big confession is that I never orgasmed, I think its kinda embarrassing because that might mean I didn’t technically lose my virginity. So thats that.

Now to wrap this up let me just say after this night I completely ignored her. For the rest of the week she followed me into men’s rooms, she broke into my room, I would literally run away from her and HIDE places. She said she wanted to leave Cancun early, which I kinda felt good about not because I couldn’t stand her but because it was flattering that my lovemaking could ruin this girl. Let me just say I didn’t do this because I hated her but because i didn’t know how to deal with her or any of this stuff. I think this happens alot, and girls think that the guy is just a jerk. Some of the time(not all) the guys just not mature enough to deal with the aftermath of sex. I know I was.

I just wanted to let you all know I’ve had lots of sex since this, and I’ve been handling it a little better.