That I lost my virginity.... Warning: This story contains documentation of drug use and underage drinking. Please do not read on further if you are bothered by these topics. Year Five - Chapter Seventeen This is the story that lead up to the demise of the friendship between my best friend and I. We were inseparable for years, and it slowly faded, after this night the decline was significant the friendship is now beyond repair. A First Time Never Forgotten It has been exactly one year since the weirdest night of my life. Who in the right sanity would have guessed that I would have sex with my supposed gay best friend on grad night. Although it was amazing it still has caused permanent damage, maybe not from the sex itself, but the friendship is no longer existent. This is a partial dairy entry for the night, and the rest has been filled in. It started getting good after the dance when the anticipation of illegally carrying alcohol in my vehicle. We were all underage, and we knew there were cops everywhere that night. Kristen, Garrett and I checked into the hotel that we rented a room at and asked the front desk to allow no one to know we were there. Which wasnt smart because they didnt even let Sarah and Travis know we were in the room. Brandon was supposed to arrive at 11:30pm so I went down to wait in the lobby for him, hotel key and vehicle keys in hand. I waited intently for him to arrive, nervous at what he would think of me in a dress, makeup, and an updo. When he did arrive I was eager to get back to my house. He looked at me and told me I looked beautiful. Then after I shrugged my shoulders he asked me why I could never take a compliment. I drove to my house and discussed with him the details of the dinner and dance. He told me that he would probably leave halfway through the night, and when I complained he told me "Its not all about what you want." When I arrived at my home I picked up my duffel bag of water, booze, pop, and changes of clothes. Then the fun started... I grabbed a lighter and a joint. Brandon and I sat on my deck off the side of my house and got high. I had my bath robe covering my grad dress, and was more than eager to get the night going. My mom peered out the deck door with her mouth wide open, not believing what she was watching. My father was asked to join but since he had to drive us to the hotel. When we were done I packed my last few things including the 40oz of Red Sour Puss that was given to me as a gift for graduating. I was upset because my parents had refrigerated it. As we got into the SUV Brandon spilled coffee on himself, we laughed at random things all the way there. When my dad dropped us off at the front doors he said all but one thing to me after congratulating me and telling me to have a good night... "behave". When we got into the room I poured a drink, my friends were all sitting in bed watching TV. We ordered pizza and Brandon and I chilled in the separate room that had a futon, TV, and a PS2. When the pizza delivery guy knocked at the door I answered in my underwear and black bra. My friends ripped me away from the door, and handed my drink so I would be distracted. Everyone was eating and Brandon had the munchies. So as Brandon talked to Devon on his cell phone I was feeding him pieces of pizza. Brandon was making tons of random comments like "Lyndsays looking at me funny", "shes going to rape me help me Devon!!". Meanwhile I wasnt even on the top bunk with him. Brandon eventually had to let Devon go, and he was talking about sleeping in his car because he was too messed up to drive. I laughed and said "yeah ok Brandon, or you can just sleep on the bunk?" He thought that was a good idea as well. I invited him down to the bottom so that we could watch some porn that he and I had picked out the day before. He was eager to watch it as well as I wouldnt let him know what it was like. So I went to grab one more piece of pizza and brush my teeth, when I opened the door everyone else in the other room screamed at me to shut the door... I hadnt realized that they could see the TV, and Travis is the biggest homophobe I know to date. So I closed it, and my friends were asleep by 12:30am, leaving Brandon and I to our own boredom. The alcohol had really mixed with Brandon at first, but he had then calmed down. It started innocently enough, and we spent a few hours watching porn. I switched from playing with his hair, to rubbing his back, until he needed to roll over onto his side, and he proceeded to tell me that I didn't have to. So I sat up behind him half heartedly paying attention to the movie, and then to his body twitching, I was trying to pinpoint the exact sort of scenes that were setting off his twitching. He seemed to roll back and forth all right, but when the content got rough, he moved again. We tried to watch straight porn but it got too weird, he said that it seemed wrong to him because the girls were being used. I didn't personally like the awkwardness the straight stuff brought up, so we put the gay stuff back on, but because the remote wasnt working we had to watch all the scenes we had watched already, all over again. This only made me realize even more the parts of the movie that triggered his responses. When I asked him about it, he didnt really have an answer for me, so we continued to watching the movie. He brought up for some strange reason, wishing he had brought the strawberry flavored body oil he had bought the day before. I didn't really think anything about it this till much later, and what he might have been hinting at. Nearing the end of the last scene Brandon seemed to relax quite a bit, and looked really tired. So because he had decided he was going to wear his jeans, and shirt to bed, I crawled over him, and grabbed an extra pair of pj pants I brought incase I spilled booze on the ones I was wearing. When I undid his belt, he just kinda looked at me but lied there like he was playing innocently, I'll never forget the look on his face, of pure serenity. He didn't really make a sound or movement till I got to his fly, it was then that he grabbed his pants, and warned me that I was going to excite him, I didn't really listen because I didn't see anything sexual to it. I continued to pull his pants off, and he warned me once more before I got them off that I was exciting him, till I took them off, then he said in this adorable voice " I warned you, now I'm excited". I slipped the pj's on him, and took his socks off, folded his jeans and had him take his shirt off, and folded it as well. The movie ended soon after I got back into bed beside him. I got up to turn the PS2 off, and turn the TV off as well, I checked what time it was outside my door, and seen 4:30am on the clock, and everyone was more than fast asleep. I was eager to do the same, but when I turned around I found a cozy Brandon in my spot (the exact spot I told him to stay out of, because I have to sleep against a wall, and with my blanket) both of which he had done.... So I moved over to the bed ( it was completely dark). I asked him to move over, and then begged him to move, Then accidentally grabbed his crotch area, and shook him, but he wasn't moving. I then proceeded to sit on top of him, like I had done so many times, so many years ago. But there was something different happening. Brandon's crotch was twitching, and I had asked him if was doing it voluntarily, be he said he wasn't. I asked him if I was hurting him, but before he could answer, I slid off his belly, to his side. I re-sat myself in a position that I was kneeling between his legs. I decided to run my really long finger nails down from his ribs to the base of his cock area... keeping in mind he still had the pants on. I ran my nails down him repeatedly asking him in order, "pain, ticklish, or torture?" He said it hurt sometimes, but when I did it really gently and asked him if it was painful, he shook his head, no. I did it again and asked him ticklish? Again he shook his head, no. So when I did it for the final time, asking if it was torture, he nodded. His reaction had to be simple enough, his back arched badly, and he moaned softly. I sat back to the side, a million things going through my mind... I asked him what I had to do, basically telling him, that this was way too weird, that I was really scared, and clueless, I put my entire body over his, and hugged him, telling him that I didn't want to mess up anything, because he was the single most important person in my life, and I didn't want anything to change. I asked him to put his hand on my chest, and to feel my heart pounding. I asked him once more if this was really what he wanted to do. He replied softly "we'll do only what you are comfortable with, and if you want me to stop, I will." He was gently playing with himself, and then he was masturbating to make himself hard. I asked him repeatedly to stop masturbating, I reminded him of my weakness for boys who masturbated, and he was the one who created that weakness of mine. He stopped but continued to play with the head of his cock I could only assume, but he was trying to make himself totally hard by the looks of it. I told him that I was clueless about sex, and that it had been five years since I had even touched a cock, let alone played with one.