The Day I've Been Waiting For
Hello, My name is Austin and I am a closeted who is also a virgin. I always had the biggest crush on my roommate and also friend Anthony. We met freshmen year in college and hit it off ever since. Anthony however is straight and just recently broken up with his girlfriend of 2 years. I always had the biggest crush on him but it wasn't at first sight. It just happen one day, I looked over at him and thought to myself damn your fine.
So me and Anthony been living together 4 years and I have yet to come out to him. I was afraid he would leave me and so I always acted if I was straight. I grew very tired of this so on one rainy afternoon we were talking and I told him that I think I am gay. He smiled and said he figured because how I would always look at guys more when we got to class and stuff. I was relieved that he took me being gay so well. Anthony played football in college so he was your average jock. I seen him nearly naked countless times and always just wanted to see well you know his dick. I also have an athletic build from working out 5 times a week.
Well on the weekend of Memorial day, we decided to go to the beach that weekend. Like I said he just got out of an relationship with his girlfriend so he was kind of ready to find something new and fresh. When we got to our hotel, there was a problem with our reservation. Instead of having two queen bed, they gave us one king bed. I said I'll just get another room but he said no it would cost way too much and we're like brothers so we will be alright. So I agree and when we got to our room it was magical. They gave us a room with an ocean view on the 21st floor overlooking the Atlantic. It was breathtaking.
Anthony was ready to hit the beach so he went into the bathroom and change into a bathing suit. Since I already had one on, we left and spent the entire day at the beach. It was nice taking in the view of the ocean and of course the eye candy. Anthony went off with some girl he met. Now if I was straight I would have to she was a sexy girl. When he came back a few hours later he had a grin on his face. I asked what happen. He didn't really wanted to tell me but I bugged him until he said she gave him a blowjob. He then said to me "she can probably give you a few pointers." I laughed and told him I need all the help I can get since I never did that before. He then went on to ask the famous question "Are you still a virgin?" I shyly said yes at 22. He then said well we're going to find someone and fix that this weekend. I said I want it to be special and not with some random but he said just get this out the way and I'll find someone special later.
After spending pretty much the whole day at the beach we were hungry so we went up the strip for some burgers. At dinner he went on to ask me some more questions. He ask me what kind of guys I prefer and why I never told him I was a virgin. I said well it was kind of easy because I thought he wouldn't want to hear me discuss sex with guys so I never mentioned it. He said we been through too much and even though it would be weird at first sex is sex and he would have gotten through it. The last question he asked took me by surprise.
He asked if I was a top or bottom. I nearly chocked on my burger but I admit to him I knew in my mind I am a natural bottom. He asked me how I knew I was a bottom. I said with no regret that I would the feeling of a juicy up my . He chuckled and that was the end of that.
That evening we decided to go out but first he wanted me to be safe so he told me to you know clean yourself (down there) and get ready to get fucked because I'm losing my virginity tonight. I laughed because its funny how well he was taking this. So I hopped in the shower and took the longest shower I ever took. When I got out and dress we went to this club. The vibe was good and this at the bar kept staring at me. Anthony told me to go over there so I did. The guy name was Clive and we hit it off. We talked for hours but it was getting kind of late and I wanted to leave so me and Clive exchange numbers and said we were going to meet up sometime that weekend for lunch.
I texted Anthony that I was leaving since he was on the dance floor dancing with guess what the same girl who in his words blew his brains out. I got back to the room, change into my pjs and turned on the tv. An hour later Anthony got back. He didn't say much but went straight to the bathroom, to shower and change his clothes. He got out and said lights out. He asked me about Clive and why I didn't let him ride my brains out. I told him that we hit it off and was going to lunch. He laughed and said if he was Clive he would have not wasted the opportunity to pop my cherry especially since I got such a great ass.
I said stop playing around but he said it's true. I was like so what I should do call Clive up and fuck. He said no I already fucked up. That's when he looked at me and said he was going to take my virginity. I said what and he said it makes perfect sense. I known him for 4 years, I trust him and since I was a bottom he wanted to know I was taking care of right. I said no because it would mess up our friendship but he said he knew I always wanted him and I could live out a fantasy no strings attached. And plus he said he was a little bi-curios so this is a win win for him too. I was someone he trusted who would go tell a soul and since he dabbled in sex before its nothing new but just a dick is there also and chuckled.
Its college, we are allow to experience different things. I agreed. So he took off his shirt and I took off mines. We looked into each others eyes and that's when he kissed me. I was in heaven and that's when things escalated quickly. He took off his shorts and there it was in all its glory. The perfect dick. I say it was around 7 inches with girth and circumcised. I was nervous but he said try it so I put my mouth around his mushroomed head and started sucking it slowly. As I build up confidence I got a little ahead of myself and started to take the whole dick but I gagged. He said take it slowly because I'm doing pretty good.
He asked if I wasn't lying about giving head. I felt him tense up and he said its his turn. So he took my shorts off and started on my 6 inch dick. It Felt wonderful. He was good and he said he heard his mouth game is on point. He knew how to work his tongue. Then I gave out a scream of Ecstasy. I cummed right in his mouth. He didn't mind and got up and said he would of felt insulted if I didn't cum. He told me to turn over and prepare for the final deed. I was ready. He put a finger in. He saw that it went in with ease I told him I've been fingering myself for years now so I'm ready for the dick.
He told me to lay on my back because he wanted to see my face when he enter me. So he got some lube in his bag and lube me up he was looking for a condom and stop and asked can he go into me raw. At that moment I didn't care so I agree. He assured me he was tested and clean so I told him to fuck me already. He laughed. He straddled me and finally put his head into my ass. I winced but It didn't hurt because I been figuring for years now so it wasn't that intense. He slowly put inch by inch in me until he was completely in. He looked at me and said how good it felt.
I agreed and he slowly started to thrust in and out and began to build up speed. I knew I was in heaven. He felt good and we both smiled looking at each other. It was better than my dreams and thats when he said he was going to cum and a few seconds later, I felt spurts of cum inside me. After he was done he kissed me and puled out. We were both sweating and tired by now so we turned off the lights and went to bed. That was the best night of my life.
I hope you enjoyed this first attempt of my very true story of my first time. I got a few more stories that I will share about the weekend with Anthony and Clive up until present day of Anthony's bachelor and the night before his wedding coming at a later time. (5 stories in all)
I had a sex experience with my gay neighbors...
- Locker Room
- Jack Off
- Teen Boy