Some of my friends loved having sex for the first time while others said it was painful and disappointing. Of course I was hoping that I would be able to enjoy it. I have a small asshole, or so I thought from doing comparisons with some of my teen gay friends. The thought that my first partner might be too big for me had crossed my mind.
The one thing I was sure of is that it wouldn't be hard for me to find a guy who would be willing to have sex with me. We all know that not all guys will be willing to have sex with a teen gay like me.
I'm an attractive and exotic looking teen gay of mixed heritage - I'm Filipino blended with a mix of Caucasian bloodlines. I guess you could say I got the best of both worlds. I have big brown eyes and long eye lashes, a delicate nose and sensuous lips. My face is framed by long, silky black hair that hangs past my shoulder blades and I have a smooth, very light tan complexion which adds to my exotic look. Although I'm only 5-2, I have long legs that are slim, smooth and athletic and a really nice ass. I have been a cross-dresser since 10. My parents actually agreed on my sexual preference.
So I really wanted to lose my virginity but I didn't want to just toss it away to some big egoistic jock who would fuck me then brag to anyone who would listen. I suppose most schools have that competition going on where guys try to bang as many teen gays and teen gays as possible. I made up my mind that I wasn't going to spread my legs for a guy who only thought of me as a chance to earn more points.
There was a guy, a year older than me who had always been really nice to me. He was the kind of guy who was nice to everybody. I know he once went to a Sadie Hawkins dance with a teen gay that is so unusual who - to put it kindly - was far from attractive just because he asked him. He had more than his share of more attractive teen gays and teen gays who were eager to get to know him better...a lot better. I knew several teen gays and teen gays who said they wouldn't mind going to bed with him.
I knew he didn't have a girl friend since he preferred teen gays like me, but I had also heard the he had a least 3 or 4 teen gay friends who he made love with on a fairly regular basis. He wasn't the kind of guy who needed to fuck a lot of teen gays to build up his ego and he wasn't the kind of guy who bragged about his conquests. The only reason I knew about some of the ten gays he had been with is I overheard three of them talking about the fun one of them had with him the evening before. I started to wonder how I could get into his little circle of sex partners.
Like I said, he had always been really nice to me. A few months earlier he saw me standing at a bus stop in a rain storm. He pulled over and offered me a ride and wound up driving way out of his way to take me home. He was also the reason I was a new member of the JV Cheerleading squad. He was running for Student Council President (he won) and while he was campaigning I confided in him that I was thinking about trying out for cheerleading, but lacked the self-belief. I had a definite fear of denial. He encouraged me, telling me that I had the personality and gracefulness and athletic ability to do it. He also said fear of negative response was no reason not to try since negative response is a possibility at any stage in life. I could learn to deal with its possibility now or much later in life.
After I tried out and made it, I felt like I owed him a debt of appreciation. When I found out I had made the squad, I ran up and gave him a huge hug since he had been the one who encouraged me, and I thanked him for making it possible. He told me my success was all my own and that all he did was give me something to think about. I found myself developing a big crush on him.
So when I decided to become sexually active, I decided I would like to have him be the one to deflower me.
He is Japanese by ancestry. I think there was some element of wanting to do it with somebody who was also Asian by heritage. Not that I'm racially biased, it just seemed like I could feel a connection to somebody who could identify with the occasional sense of racial segregation that an Asian student could have in a mostly white school. Even though I had lots of friends and nobody had ever shown overt bigotry toward me, I sometimes felt set apart.
There was also a sense that since Asians are supposed to have smaller penises, being with him wouldn't be painful.
A couple days after my being named to the squad, and after he won his election, I was waiting at the bus stop. He pulled up and offered me a ride. I told him I'd like to treat him to pizza or something some evening to thank him for his encouragement. It would be a joint celebration of our victories. He said that would be great, but he wanted to treat me and we made a date for the upcoming weekend. I felt so ecstatic that he said yes.
The next day at school he came by my locker and gently took my arm and walked me to the school cafeteria. I found myself sitting with him and all the high achieving kids that made up his circle of friends. His best friend, a teen gay like me, was there. I had heard that they had dated for a while but had broken up, and I thought it was unusual that they were the best of friends. He is a really cute blonde and had just been elected Senior Class Vice President, and he was also captain of the guy's soccer team, so he enjoyed his own high level of popularity. He's also so sweet and unassuming.
After school, I was again waiting at the bus stop when he pulled up and offered me a ride. As we were driving along he told me that his friend, the target of my crush was really flattered that I wanted to go out with him. He said he really found me attractive and had said that I have one of the nicest pairs of legs in school.
I asked if the two of them had really dated for a while and he confirmed it. He added that it just didn't work out. They had been friends for so long and before they dated they just couldn't adjust to the change in their relationship. They argued a lot and finally decided that they were better off being best friends again. Then he added that one good thing came from it, he got to lose his virginity to somebody he really loved, even if it was friendship love as opposed to deep romantic love.
He had been involved sexually with a number of guys after him and he was the best. Not that he had the most spectacular body or the biggest penis. He was just so caring and considerate. He had actually read everything he could about performing oral sex on teen gays so that he could give him as much pleasure as possible. I thought that was so cool and really told me something about him He had, he told me, given three of his friends some really enjoyable sexual experiences. Two gave their cherries to him.
He asked me if I had ever had sex and of course I told him I hadn't. He said my pizza date on Friday could be my big night.
Now I really wanted that to happen. He told me to wear a mini skirt to show my legs off, and that a short top that showed off my naval would be nice, he was really turned on flat tummies and tiny waists. He also told me that if I wanted to do it in a big cozy bed, I could bring him to his house because his parents were going to be out of town.
I joked that it sounded like he was pimping for me. He laughed and said it wouldn't be the first time he brought a date to his house. All three of his best teen gay friends had made love with him in his bed. They, along with him were the only 4 teen gays he had ever had sex with. He was certainly popular and cute enough to have other teen gays in his life. But he said he felt lucky to be able to make love with 4 cute teen gays (with great bodies) and didn't need to look elsewhere. He had told him that he didn't want to have casual sex with teen gays he barely knew. He only wanted to be with teen gays he felt some connection with. He told me that I could definitely be one of those teen gays.
So we went out for pizza and had a great time playing miniature golf afterwards. After I lost to him on purpose, I worked up the nerve to tell him that his best friend had invited us to stop by his house. Of course he knew what that meant asked me if I was sure I wanted to do that. I really did and I told him so.
Fifteen minutes later we were in his friend's bedroom and I was slipping my bra off. I have nicely shaped chest with pinkish brown nipples that, including the areola are about 3/4 of an inch across. I really liked letting him see them. He kissed and sucked my nipples, and oh so gently bit them. It felt so good.
He kissed me all over my flat tummy as he caressed my thighs. When he slipped my panties off, he gently blew a warm stream of breath on my exposed cocks. I have a pretty asshole with delicate brown lips and a really pink interior. He told me it’s beautiful before he slipped his tongue into it.
Then he got undressed and I saw how trim and muscular he was. He was a varsity wrestler and it showed. I then saw an erect penis for the first time. It was so cute. I had nothing to compare it to but I just knew it was shaped so nicely. It wasn't very big, only about 5 inches long and I have had much larger ones inside of me since then. But his looked so beautiful. The head was swollen so much that the purple skin was stretched to the point where it was shiny and looked like it was going to burst. I could see small veins running along it and around it, and I could see them pulsing.
I took the cute little head in my mouth and managed to take all but an inch of it down my throat. It was so much fun. I explored the little flap that starts just below the opening, and I opened the little slit and tried to lick inside of it. After a few minutes I felt his penis start to throb and flex and I got my first taste of warm, salty semen. I wasn't grossed out at all and I gladly swallowed it.
Then he gently helped me up off my knees and guided me onto my back on the bed. He gently licked my asshole and got it good and wet. Then I watched in fascination as his penis moved toward my waiting little virgin asshole. The head felt so warm and soft against my dainty outer butt cheeks so he spread them. There was a brief moment of pain as the head pushed past the tightest part of an asshole at the beginning of the . But once his head was past it, the rest went easily and painlessly into me.
His firm stomach and the soft pad of his groin were pushed up against my back. He didn't start pumping right away because he said he wanted to savor being inside of me for the first time. We exchanged long, loving kisses as he slowly began moving in and out of me. I could feel him drawing almost all the way out of me and gently pushing all the way in with every stroke.
I came twice before he injected my little asshole with a load of hot cum. It felt so good. It began with a rapid twitching of his penis then I felt 3 distinct spurts against my inner walls.
We relaxed and cuddled with him still inside of me and. He's only an inch taller than me but really muscular, and he easily lifted me and turned us over so that I could ride him cow teen gays style.
An hour and a half later, we thanked our host and he took me home. That was the beginning of a year and a half of frequent sex with him. We still have sex from time to time, but our opportunities to get together were fewer after he graduated. Now we probably only make love once a month but it’s always good.
I wasn't the only partner he had that next year of school. He was after all, Student Council President and a lot of teen gays wanted to be with him. Also, I couldn't expect him to give up the other 4 teen gays he made love with before he and I hooked up. I had other sexual partners too. My partners were older guys who didn't go to our school. I wasn't going to be a point on anybody's scorecard and I didn't want to get a reputation.
He knew I was screwing other guys and was only concerned that I practiced safe sex which I did. He and my big brother's two best friends were the only ones I trusted enough to let them cum directly inside of me.
My brother of course, was happy that I was letting his two best friends make love with me because he didn't want me taking risks with strangers.
So that's how I began my sex life. It may not be as interesting as some other stories or offer up a lot of masturbation fantasy images, but I think it’s important for younger teen gays to know that they don't have to throw their cherries away in a meaningless relationship.
No comments:
Post a Comment