I was 18 on leave and was out in San Diego California. Had a month off and didn't really want to go home to face an Ohio winter, so I went and visited a friend, Jay, in San Diego.
Jay and I had met and became friends in middle school and hung out a LOT! Spent the night at each others house and even slept in the same bed a few time. Camped in the same tent. We even went on double dates. He dated a few hotties in High School.
So went out there to take advantage of his couch and walking distance to the beach for a couple of weeks. Figured I was in for a couple of weeks of fun in the sun and some intense party time.
So our first night hanging out, he tells me he is into guys and hoped that didn't bother me. I said, for how long? He said for a LONG time. And asked if he ever thought that about me while we were hanging out? He said oh hell yes and that he even jacked off a few times after I had fallen asleep and even once dripped cum in my mouth to stop the snoring.
So he asked if I had ever thought about a guy or been with a guy. I told him about my one big gay encounter while hitch hiking and a bath house. He laughed and just said cool and kind of blew it off. The next night we went out to a gay/drag bar by Pacific Beach and met up with several of his friends that were regulars there. We all went to an after party at one of the drag queens house. My first time trying pot brownies! Yummmm!
After a lot of drinking and smoking, people started sort of pairing off and it became almost like a free form orgy. I saw a lot of different dicks and asses in a short period of time.
I and several others were having a deep conversation with a different drag queen. Who in the hell knows what about. Soon enough, things turn to sex. The drag queen tells me that she is in to fucking young boys, which blew my mind. I figured, look like a woman, take it like one... Not so much. About 4 of us on the couch and she starts by playing footsy with my crotch and ass and then leans in and starts kissing me.