High School Buddy and Friends of Both Sexes

I was terribly shy in high school. I was a follower, definitely not a leader. Still am. That's why I'm coming to you [for counceling], of course. [I asked, "So in your high school days, who would you have been if you could?"] I would have been Jan Steinmann [not his real name]. Now, he was a real leader. I know the kind of stories you like to write up, and you can go ahead and publish this one. It's a real doosie. He was Jewish. Not so much so that he had to wear a little hat, but he was more Jewish than I was Methodist. I found that intriguing. But the real thing is that he was the best at everything. He was the pitcher on the baseball team. He got As in every class. He had a winning smile. He knew just how to talk with everyone, even girls. Especially girls. They were always laughing and carrying on with him. Oh, and he was tall and thin, with longish curly black hair. Yup, that's who I would have been. I never spoke with him. I watched from a distance, always fascinated. How did he do what he did? Why was life so easy for him? I'd see him leaning in a doorway, entertaining a girl with a story. I'd hear it. It wasn't that funny, but she'd laugh as if it was the funniest thing she heard all day. I'd see him get up in class and deliver a flawless report. Out on the field one day, a batter hit a low hard drive right at Jan. Right at his stomach. He caught it in his baseball mitt, as if that was an everyday occurrence. It would have killed anyone else. All the boys cheered him. They always did. One day in biology, I was paired up with Jan on a project. It was the first time I ever spoke with him. He had a smile for me, as if we had always been good friends or something. I was almost nervous when speaking with him. Like he was a movie star. For the first time, I noticed a slight accent. I think it was like Russian or something. During the little science project, at one point, he said, "Hey Ron, why don't you come over to my place after school?" I was flattered beyond belief. I was like, "Glad to," and put his address and number in my phone. I texted my mom to be sure it was OK, then put the phone down so the teacher wouldn't notice. I was figuring I'd walk over, or maybe take the bus. No, Jan had a car. Of course he did. It was a battered up old pickup truck. He drove me to his place. Jan's house was a typical two-story home. Nothing super-wealthy, but I did notice it was neat and clean, and there was a baby grand piano in the living room. "Do you play?" I asked. "I noodle around sometimes." "Can I hear something?" "Sure, if you'd like." He then sat down and played some sort of old-time honky-tonk piece that was so amazing it almost made my eyes water. We went upstairs to his room. "Do you like porn?" he inquired. "Who doesn't?" He unplugged his laptop, sat on the edge of his bed, and beckoned me to sit next to him. I sat about six inches away. He scooted closer so the sides of our butts were touching. I thought nothing of it, figuring he just did that so we could both see the laptop better. I felt a sort of thrill, too, since this was Jan Steinmann next to me. He was actually being  my friend. How cool was that? It would be a bump up in status at school if people would see me with him. We looked at some porn. I wished I could jerk off right then and there, but obviously that was out of the question. I wondered if Jan felt the same way. I didn't have to wonder for long. "Do you jerk off?" he asked. "I... um... well, yeah." "Me too. All the time." I couldn't imagine Jan Steinmann jerking off. Why would he? He had all the girls he wanted. Or boys, too, if he was into that sort of thing. "Let's do it." He said that as casually as he might have said 'Let's raid the fridge.' I was shocked! "What about your parents?" "They won't be home until 6." He didn't have any brothers or sisters. Before I could sort things out, his pants and underwear were down around his ankles. He sat back down on the bed, setting the laptop aside, and started fiddling around with his penis in its nest of curly black hair. He was already erect from watching the porn. So was I. So what does one do in such a situation? After a moment's hesitation, I pulled my pants down too. "Hey, nice dick" he said. "Um, your's is nice, too." I offered. It was nice. I suppose I was expecting something huge, something glorious to match everything else about Jan. But no, his was about the same size as mine. We sat there jerking off side by side for a moment. Then he switched hands so he could wrap his free arm around me. I have to say, that felt wonderful beyond words. In my whole life, I had never been hugged by anyone other than my parents and the occasional aunt. And never while naked. I felt the warmth of his whole side, against my side, his arm around my back. My penis started pulsing and cum spurted out. Jan laughed good-naturedly, "Wonderful!" He then kissed me on the cheek. I was a bit weirded out. No, I was very weirded out. The kiss, combined with that post-ejaculation feeling a guy can get was overwhelming. I wished I wasn't there, and the whole thing hadn't happened. After a moment of hesitation, I felt the sperm running down my lower stomach, over the top of my balls, threatening to flow down onto Jan's bedspread. I quickly got up, and took some Kleenex from a box on his dresser. Meanwhile, Jan was sitting there, jerking off like mad, and came with his own squirts of cum a minute later. "Spectacular!" he said. I made some sort of excuse, and left within minutes. Walking home, I kept running the whole thing over and over in my mind. I didn't know what to make of it. I was sort of scared and regretful, and at the same time, I knew it was a remarkable turning point of some sort. A couple of days later, found me at his place again. That feeling of dread I had felt after wanking with him had entirely evaporated. I was so looking forward to jerking with him again that I could barely focus in school. The day dragged on and on until we arrived at his house. This time, he immediately threw off all his clothes. I followed suit. We stood facing each other, stark naked, with raging erections. He grabbed me, and dragged me down on his bed. We rolled around, and kissed. This time, we kissed on the mouth. I kissed him back with absolute joy. On that day, I learned just how great blowjobs can be, both giving and getting. He and I repeated our afternoons many times. In school, he started hanging out with me. I had always been on the baseball team, but I was sort of an unnoticed outfielder. As if by magic, I became a really good hitter, and people started noticing. I liked it. I attribute my growth on the team to my friendship with Jan. He and I talked a couple of times about buttfucking. He said he'd love to do it, but won't. Too dangerous, he said. One can get diseases. Besides, as he put it, "It was too gay." That led one time to a discussion of sexuality in general. As usual, I didn't have much to contribute to the conversation, but Jan got on a soapbox, as if he was talking to twenty people, even though it was just naked me in the room: "I'm not gay. I'm not straight. I just like people. I like to wank with people. Masturbation is a very good thing. Especially at our age. It keeps us from going crazy. I feel sorry for anyone who thinks wanking is bad." He went on and on about the benefits, and how all of society should embrace jerking off. A thought occurred to me that hadn't popped up before: "Has he wanked with other people? Gosh, he probably has. I wonder who?" I was a bit jealous. But curious too. During school the next few days, I kept looking at the people Jan talked with, wondering, "Has he wanked with him? Did he do something with her?" One morning in Biology class, he said, "I've arranged a party of sorts. Kyle is coming over too. I was super-excited. Kyle was an Asian kid who I was sort of friends with. I had no idea he and Jan had jerked off together. The three of us did get together. Kyle kept insisting he wanted to get buttfucked by one of us, but both of us firmly said "No." Finally, Jan relented a little bit, saying, Kyle, I'll buttfuck you with my fist. Kyle was so excited he was shaking. Jan got some more cream, and instructed Kyle to get on his hands and knees on the bed. I had a plain view of Kyle's asshole, which I really enjoyed seeing. Jan approached with a greased up finger, and slowly twisted it into Kyle's butt. Kyle was in heaven. Then Jan backed out, then reentered Kyle with two fingers. I was practically orgasming just watching. Jan then tried three fingers. He went very slowly, but Kyle stopped him. "It's starting to sting." We all jerked each other off to crashing orgasms. Now, it was often the three of us. Sometimes just Jan and I, but it was at least two afternoons a week. One day, I walked over to Jan's house, knocked on the door, all ready for one of our usual sessions, and who should I see standing right behind Jan, but Liza Hartley! She was hands-down, the prettiest girl in the school. Blond hair, tall like a model, thin, big tits. Oh, my God! Were they doing something? Had I interrupted? No, they were fully clothed, and didn't look flustered. Then, I had the crushing thought that I wasn't invited. They were going to throw me out. Probably politely, but this would be just them. I was becoming devastated by the second. "Oh, good, Hello Ron." In a heartbeat, my emotions shifted big-time. Was this for real? It was so unexpected. Like a dog walking along the sidewalk, and suddenly someone's ice cream cone falls to the ground. What a treat for the dog! What a treat for me, if it was really going to happen. Maybe it wasn't. Maybe we were just going to do homework or something. But no. We got up to Jan's room, and Jan and Liza were out of their clothes within a minute. So was I, already sporting a huge erection. So was Jan. Liza was even prettier without clothing than I imagined. Her breasts were bigger than I thought. They swung back and forth when she moved. She had a neatly trimmed patch of brown hair over her crotch. Hmm, I didn't realize blond people could have brown hair down there. And what a butt! To die for. Maybe bigger than I imagined, but I so wanted to touch it. So, for perhaps the first time in my life, I did something bold. Maybe I had been learning boldness from Jan. I walked right over to Jan, put one hand on the side of her butt, and gently guided her to the bed. We fell on the bed immediately, and started rolling around. The feeling of her tits against my chest was something out of this world! Jan jumped on us, and all three of us were just hugging and rolling. Then, we started kissing. Mostly it was Jan and Liza, but then Jan took a break, and French kissed me. I wasn't sure I liked it, but I didn't not like it. In a minute, we switched positions. I French kissed Liza, and that was really something. Delightful! I could have done that all day, but there was even better stuff on the agenda, and I was super horny. There was pre-cum leaking out of my dick, which only happens in the best of times. There was something else. More pre-cum than made sense. I discovered it was something coming out of Liza. I reached down to discover what was going on, placing my fingers against her wet vagina. She immediately laid back, saying "Ummmmm." Her vagina was very wet. I twirled my fingers around the outside of her vagina for awhile, then started sort of inserting my first finger, just maybe a half inch into her slit. She seemed to like that, so I pressed further and further in. Pretty soon, I was outright fucking her with two fingers. I felt her insides convulsing around my fingers as she yelled in outright abandon. It was the first time I had ever felt a girl orgasm. Hell, it was the first time I had ever even been naked with a girl. Meanwhile, Jan had been playing with my penis, and as Liza came, so did I, all over Jan's hand. After my recovery, I decided Jan was due for a special treat, having let me and Liza play like that. I had him get on all fours, and slowly introduced a finger into his butt to his absolute delight. It was the first time I had ever done that. Liza reached under him at the same time, and started jerking him off. He came almost instantly. Jan and I became major friends all the way until graduation. We had a big group of friends around us including Kyle and Liza. They, and some other people, and Jan and I pretty much had something going on in his room after school at least twice a week. It would have gone on forever, except school ended. Jan went to college, eventually becoming a surgeon in Chicago. I joined my dad in the HVAC business. Liza married a nice guy and moved to California. I ended up marrying Kate, a wonderful girl I actually met in Jan's bedroom. She and I had sex of a sort even before I knew anything about her. I should say it wasn't actually sex. No one ever had sex in that bedroom of his. We had all decided it was too dangerous. No one wanted pregnancy or disease. Besides, those who did have intercourse with people (outside of Jan's room), reported that our masturbatory sexual play was actually better. So now, Kate and I have two small children. I hope they have an opportunity like I did as they grow older. I hope they both grow up to be successful and outgoing like my old friend Jan.