Dear Craig,
With so much change to come our way, I thought I would take some time to reflect on our long friendship and suggest a new tradition to keep us from drifting apart. I’ve always believed that we would stay friends forever. We have been through everything together–first steps, first day of kindergarten, first fight, first boner, first kiss–and now we are off to separate colleges to experience a whole bunch of firsts. Perhaps by the end of it we will have grown into totally different people, no longer a good fit for each other. With this possibility in mind, I need you to do me a favor.
Can you think back with me on some of our best moments this year?
My birthday. You said that we were both adults now and that I needed to get laid. But neither of us have any game so we watched porn in my basement instead. You may not look back on this as anything other than normal, but I remember. You wanted to show me your older sister’s nudes. I was shocked and delighted seeing my old babysitter with her legs wide open, her crotch splayed and glistening in her bedroom mirror, her A-cups sitting perky beneath her taught chin. That one failed to turn me on, though, as did the one of her sitting on a dildo, and the one of her masturbating by the pool. It sure turned you on, though, and when I saw that, saw you hard, it flipped a switch in my head.
Remember also the time that I asked you to look at that bump for me. You got hard then, too, and I couldn’t tell if it was for me. You knelt right in front of me and slipped two fingers into the waist band of my gym shorts. You told me not to worry, that it couldn’t be anything bad, and then took them off. I wondered why you were being so gentle, but I was glad. Then you took my dick in your hands and looked. It was probably a pimple, you told me, but it would be easier to tell if I got hard. So I started to pull at it, right there, next to your calm, strong face, under the warmth of your breath. You were right, it was just a pimple.
Some people say that you’re not best friends until the people around you question if you are a couple. We have often joked about being secretly gay, and then you met Sarah. I was so happy for you finally losing your virginity, disappearing for days, it seemed, to have sex with her, but I missed you. And when you sent me those videos and told me to jerk off to them, I knew you were joking. But I did jerk off to them, especially the one where she held the camera.
You have a beautiful body, Craig. You look good. You can see it all in that video. You stand tall, sweat lighting up your muscles. Your chest bobs up and down as you look at her, at the camera, figuring out how you are going to take her. Your lift your cock and lay it on her wet sex. Her legs squeeze a little, and you slowly run it back and forth over the top before entering. Your abs squeeze as you pump at her pussy. Your arms hold your body just over hers. Your hair dangles just a little to the side. For some reason it’s the hair that brings me to completion every time.
We may be friends forever, or we may lose each other. Either way, I needed to come out to you. You’re the only one I trust. I am gay, and I know this thanks to you and your videos.
My favorite memory of this year, and my life so far, happened last night at the pool. We were sitting out there alone when we heard some noise coming from your sister’s room. She had a boy over, and had closed the shades but forgotten the window. We heard the moaning, the rhythmic thumps, and you started to get hard. You pulled out and started jerking, and so did I. When you had your eyes closed, fantasizing about whatever, I was looking at you. By now I knew that I was gay, and my first gay crush was my best friend, who was stroking his throbbing cock right in front of me. When I grabbed yours and started stroking it, it wasn’t new for you. We’ve experimented together plenty, and you got right to pumping into my fist like you always do. But it was new for me because this time it was more than exploration. This time it was gay.
I’m sorry if this letter is the reason we lose our friendship. But I can’t imagine going off to college trying to lose my virginity to experienced men. I want you to be my first.
It doesn’t have to be gay for you. It doesn’t have to be cheating. We are both men, good friends who can pleasure each other and not have to feel some way about it.
We can do it like we know how. You can put on a porno–a straight porno. You can start touching yourself, and I can touch you too. I can take your throbbing cock in my hands and stroke. I can make you feel good. I can take you in my mouth, like the girl in the porno. I can lick all up and down your shaft, run my tongue around your tip. I can get on my hands and knees and turn around so you watch the porno while you fuck me. I can try swallowing.
I know this must be a lot to take in. I don’t want to be your boyfriend. I’m don’t think you are gay. I think only that you are a good friend. You can trust me to never tell anyone as I am trusting you to never tell anyone about this letter.
We have many secrets and many pleasurable moments to cherish. I hope that we have many more.
I love you as only a best friend can.