This is a true story from high school years.
I was very smart when I was 16, extremely articulate, and was a champion of the debating team at my all-boys prep school. I joined the Model UN club at 15, and was a star. I liked it because we got to go away for three or four days without parents around.
I had never had a girlfriend, had sex of any kind, or seen pornography. I don't remember the first time I saw a Playboy, but that was pretty much my knowledge of naked girls. Up to this age, I had no access to any more detailed pornography. I didn't figure out how to masturbate until 14. Once I did, however, I was generally doing it two to three times a day.
My first experience with a girl was at Model UN. My school was representing China, I think. Curiously, this memory is hazy but the details to follow are crystal clear. We were at a nice hotel in Boston; the Copley Plaza, maybe. Two other boys and I shared a room facing the hotel loading dock. We were hanging out with some girls from a private school in New Jersey in a hallway filled with people our age and no chaperones, who attended some kind of reception that night.
Never one of the 'cute' or good-looking guys, girls were generally uninterested in me. But a nice girl my age struck up a conversation with me in the hallway of the hotel. 'Do you have a view from your room?' she asked. I was so lame that I couldn't figure out a motive for this question.
'No, we face the loading dock.' What an imbecile. You can already see where this was going.
'We have a great view of the skyline from our room. Want to see it?' Seriously, I thought this was stupid. I didn't care about views and wanted to stay with the group and hang out. I wanted to be polite, however.
I said, 'Sure.' She led me to the elevator where we went to one of the high floors. She opened the room and I followed her in. There was girl stuff everywhere, clothes, blow-driers, bras. I wasn't embarrassed, but I still didn't see the point.
She said, 'The view is best with the lights off.' She turned off the lights and sure enough, the skyline of Boston lit up outside the window. In the dark room, lit by the streetlights far below, she stood next to me. I was looking out the window at the lovely view, completely oblivious to being alone in a dark hotel room with a nice girl. That innocence didn't last long, however. We looked out at the skyline in silence for a couple of minutes. 'I heard,' she said out of the blue, 'that you can milk a boy just like a cow.'
I kept looking at the skyline. I may have been naive, but I was a great debater and didn't claim not to understand what she meant. That doesn't mean I had any idea what to say. 'Uh, I never thought of it that way.' At least, I hadn't until she said it. Before the words had left my mouth, my penis was as hard as it had ever been.
'Would you show me?'
'Huh?' This from a guy with a Model UN trophy.
'You know,' she said, 'in the bathroom.' My heart was beating faster than I thought it could but I was still looking at the skyline.
'OK.' She went into the hotel room bathroom and turned on the light, which seemed very bright after looking out at the view in the dark. I followed her, having no idea what would happen but still being excited by the situation. She closed and locked the bathroom door.
The hotel bathroom was fairly large, with two sinks. To the right of the sinks was a toilet, and to the right of the toilet was a bathtub. Above the sinks and toilet was a mirror covering the whole wall. For boys at least, this meant they could watch themselves go to the bathroom. She sat down on the edge of the bathtub next to the toilet, and motioned me to stand in front of her. She had me standing in front of the toilet. Again, I didn't see a purpose for this, but in retrospect she must have assumed that boys ejaculate like they urinate. My mouth was dry and I was literally shaking. I certainly couldn't talk. 'Show me,' she said.
I undid my belt and trousers and let them fall to my ankles. My erection must have looked garish in my briefs. I looked at her staring at them. 'These too?' I asked nervously, with my thumbs in the elastic waistband. She looked up at my face for just a moment and nodded. She looked nervous, too. I pulled the front part of the elastic away from my body so it wouldn't catch on my penis, and in one motion pulled the briefs down to my ankles. I just stood there as she stared at my penis from about a foot or two away.
'I never saw one before,' she said in a matter-of fact way. She looked at it closely, moving her head around so she could see it from different angles. At that age, my erections were bone-hard and absolutely vertical, with my penis hovering parallel to my abdomen. The hole in my penis-head would point directly at the ceiling, and if I looked down I would look directly at the hole. 'Can I touch it?' she asked, and this time it was my turn to nod. At first, she touched it very tentatively. She seemed particularly interested in my penis hole, which after just a few moments she gently tried to spread open and look inside. Of course, she couldn't see much. 'Is there a bone in it? It's really hard.'
'No, I just get really hard.' I was also breathing pretty hard at this point.
'Where are your balls?' she asked curiously, moving her head down to where she thought she should see them between my legs. She seemed like she was doing a science project now, already comfortable feeling the different textures. She gently squeezed the head of my penis and the rim around it, noting without saying anything that it was different than the shaft. I breathlessly explained that when very erect, my scrotum tightened and pulled my balls close to my body. Without thinking too much about it, I reached down and stretched my scrotum a bit to show her my balls. 'Interesting,' she said, and comfortably felt each testicle, rolling it around in her hand. 'Does this hurt?'
'No, but it would if you weren't gentle.'
'OK. Let me know if I hurt you.' Methodically, she felt and examined every part of my genitalia. She ran her fingers through my blonde pubic hair, felt the head a lot, and touched and kind of stroked the hole. After several minutes of this, she simply wrapped her hand around the shaft. She experimented with holding it gently and squeezing it harder and harder. She squeezed quite hard and asked if it hurt, but it didn't. 'Show me how,' she asked. I knew what she meant.
At this age, I had no idea any boy could orgasm without a lubricant, and made none of my own (I didn't find out that some boys could do this, indeed, make a lot of lubricant, until many years later). I asked if she had any hand lotion. She did and I told her to put some on my penis. She rubbed it in like putting cream on a rash, with one finger. I explained how she should put her hand around my penis and use the lotion to lubricate her hand. She did this, but she was new to the idea and the timing just wasn't right, despite my arousal. 'Just do the head,' I requested.
'Is that this part?' she asked earnestly, touching the glans of my penis. Again I nodded. She put lotion on the head of my penis and held it in her moving hand. Now I could feel that it was going to happen.
I faced the toilet, though since my penis was pointing straight up, I know that my ejaculation wasn't likely to hit the bowl. I didn't want to squirt sperm on her, and it was astounding watching this unfold in the mirror. She was completely focused on the opening in the head of my penis, so I watch her looking at it like a true voyeur. 'It's going to come out soon,' I said. I had never heard the term 'coming.' 'Keep going. Don't stop.' With my left hand I braced myself on the sink, and I stood on my tiptoes as my muscles tightened with orgasm. I grunted once and a stream of thick white semen shot out of the hole in the head of my penis and onto the mirror in front of me. It clung there heavily and then another stream spurted out of the hole and onto the mirror. It hung in the air as if the head of my penis were attached to the mirror. Two or three more spurts came out of the hole and covered her fingers, dripping to my underwear and trousers at my ankles.
'That was unbelievably cool,' she said. I thought I was going to faint. My penis didn't soften much, as she stared wide-eyed at surges of thick white semen still emerging from the hole. Just then, we both heard a key in the lock of the door to the hotel room. Without saying a word, she dashed out of the bathroom and closed the door behind her. I got the idea, flushed the toilet and ran the water in the sink as if washing my hands, and left the bathroom. Her roommates had returned.
'Thanks for letting me use the bathroom,' I said.
'Sure. I'll see you around,' she said, and I knew that she was ready for me to leave. I returned to the party hall, and a classmate commented on wet spots on my pants. I said that I had spilled a drink.
Nothing more happened at that time, and I wouldn't have another girl touch my penis for several years after that. Although I have masturbated thinking of that encounter, only recently have I recalled that I never cleaned off the mirror, which had semen dripping down it when I left, collecting in a thick pool at the base. Did the other girls see it? Did she tell her roommates? She didn't wipe her hands, what happened to that stuff?