Many times, but one time the opportunity was a definite – and I chickened out. I was 16 or 17 and was at a buddy's house, just sitting on his bed shooting the breeze and listening to tunes with no one else home. I'd had "fun" with other boys before, quite a few times, but wasn't sure if my buddy had. Somehow, we started rubbing each other's thighs, going higher and higher, and giggling like little girls. Nobody can tell me we both didn't want it. I was hard as a rock, and I think my buddy was, too. To this day I regret not having gone further and just unzipped him (and myself) and started playing. There was quite obviously no reason not to, but I guess I was hoping he'd make the first move. Our "touchy" session ended with no further physical contact or talk about it, and that was that. You can never re-do lost opportunities like that, but I still fantasize about how hot a mutual session with him would have been had I not been afraid. I just chalk this one up to the "I was a fool" category.
- age 47, Illinois
This Week's Wackiest Response:
Well, considering that her hands were actually scissors, I think it's better that I didn't let her play with me.
- age 16, Ohio
I encountered this problem not long ago when I was partying with a friend and ended up staying the night after everyone else had left. We were both pretty drunk, and we ended up putting in a porn and relaxing next to each other on the sofa. As we watched the movie we obviously became aroused, and my friend started rubbing himself and talking about wanting a handjob, and he added that he didn't care who gave him one because he was too drunk to remember it. I sat there pondering about doing it, but I ended up just going to bed. I was worried that we would damage our friendship, and even though we're both straight, I thought that he would never see me the same again. In retrospect I wish I would have gone for it. But maybe it's better to leave some lines drawn in your relationship with people you really care about. Being horny will come and go, but life-lasting friendships come around only a few times in your lifetime.
- age 19, North Carolina
My friend and I would often watch pornography together, and he once told me he had masturbated with someone. This interested me (I'm completely straight, by the way). So after a few times of missed opportunities when we were masturbating together, I finally got the courage to try it. It was one of the best orgasms of my life. We've masturbated together a couple more times. For some reason, the experience is more enjoyable when you're in the company of someone else.
- age 17, Michigan
I was just out of high school and staying with a younger guy while his mother was at work – not because he was too young to stay alone, but because his mother didn't trust him to be by himself. She sold it to him like I was his "big brother." One night, we started talking about girls and stuff and he began to get a little too comfortable. I had messed around with friends before, but when I figured out what he was up to, all the flags went up and I knew that I had to change directions. Part of me wanted to satisfy my natural curiosity, but good conscience prevailed and got us involved in a "project" that led his mind away from what he wanted to do. A few months later, I learned that an adult had abused him when he was much younger and as a result, a few people faced criminal charges. I think fooling around and experimenting is a natural part of growing up, but when adults use their authority as respected elders or caregivers for their own sexual gratification, the line between what's acceptable and what's unacceptable becomes very clear. Had I gone ahead with what he wanted, I might have been seen as just as guilty as those who exploited him earlier.
- age 34, Indiana
My 12-year-old male friend came over one day. We watched porn in my room, both wearing just our boxers and both with erections. I wanted very much to masturbate with him and to masturbate him. (I am straight, but also a little bisexual.) He had come over several times before and we had done the same thing each time, but I never had the courage to ask him about masturbating together. I'm afraid he would think I am gay.
- age 15, California
About 4 years ago, I was hanging out with my best friend, who lived right across the street. We were talking about the usual stuff – girls, sex, girls, and sex. Eventually, the conversation drifted toward masturbation (including JackinWorld), and for the first time, I thought I might actually have a mutual experience. Our talking slowed, we couldn't find anything more to say, and I know I was pretty hot from the conversation we had just had. If he had suggested mutual masturbation, I'm sure I would have agreed because I was dying for some relief. But he didn't, and I didn't have the nerve to suggest it. I thought it would be weird, and yes, gay – but now, I wish I had pursued it, regardless of what it's considered, because it would have been a nice memory to share with one of my best friends of all time. He moved later and I've never seen him since.
- age 21, Connecticut
I have engaged in mutual masturbation before, but this time I was scared to ask. My friend and I were lying on the bed, watching a "movie," and were masturbating next to each other. It was the perfect time to ask, but I know that he is either extremely heterosexual, or if he has questions about it, he does not want to pursue them. I definitely would not mind masturbating him, but I don't want to risk anything because we have been friends since second grade. Maybe someday....
- age 16, Mississippi
I must have been 14 or 15 – I was in the basement at my neighbor's house, with a few friends. Then I didn't really know that I was gay, but was definitely aware of my curiosity and rather scared of it. One of my friends, call him Tom, went into a backroom with another, call him Dick. They didn't say why they were going, but upon their return they told me what they had done. Tom and Dick encouraged me and my other friend, call him Harry, to go and do what they had done. Harry was unsure at first, but eventually agreed. I went with him. He nervously began to unbutton his pants, as I stood frozen and watched him. His penis was so much bigger than mine that I was embarrassed and said it felt gay. Harry had already begun to masturbate, but I left.
- age 23, Minnesota
I was watching TV with a handsome foreign student in a shared house one night and a soft-porn movie came on. I started to get an erection but just said, "Enjoy," and then excused myself to go upstairs to my room to masturbate. I was curious, though, and peeked down from the upstairs hallway to see him on the couch. Sure enough, he was already rubbing the bulge in his jeans and soon unzipped to release his large, erect penis from his shorts. As he stretched out and began masturbating openly, my penis throbbed and I wanted to go back down to suggest joining him. However, I hesitated and then it was too late; he ejaculated quickly and left the room. Thinking about seeing his sperm shoot and what might have been, I masturbated 3 times that night to strong orgasms.
- age 50, Canada
When I was 14 and at summer camp, a friend and I dodged one of the 45-minute activities and went up to the 4th floor of one of the buildings (it's a school during the winter). We got onto the topic of masturbation and penis size. We both had erections and could each see the other tenting his shorts. We talked for a while, but at risk of being seen as *gay,* we didn't do what we both wanted.
- age 16, New York
When I was about 10, I spent a week with my parents at their friends' cottage. A boy about my age wanted me to take off my swim trunks when we were alone, but I refused. Judging from his behavior and the bulge in his swim trunks, I knew he wanted to engage in some form of sex play, but being a coward, I was afraid to comply. When he persisted, I told him that was something a good boy would not do. That admonition worked and he dropped the subject; apparently, he'd heard it from his own parents. Now, he was hearing it from his friend. Over 50 years later, I still regret that failed opportunity.
- age 62, Michigan
When I was 12, I was camping at a Scouting event and I had to sleep with a guy that was 16 and who was rumored to masturbate a lot. I wasn't really thinking of doing anything with him because of how much older he was. The first night, I woke up in the middle of the night to hear him masturbating right beside me, but I couldn't see because there was stuff in the way. I got very nervous and started to shake a lot. Nothing happened because I was so scared, but if that were to happen now, I would ask.
- age 14, Iowa
When I was in the Navy, I pulled temporary duty at another base along with my chief. He and I arrived there quite late. After checking into transient barracks, we went into town to eat, came back to the barracks, and showered. Just the two of us were there and he got an erection. It turned me on to see him. He said it was a shame to "let these good hard-ons go to waste; how about taking care of each other?" But I couldn't bring myself to do it. I still think about it after more than 40 years and wish I'd gone along with it.
- age 60, Canada
When I was in junior high school, I was at a friend's house while he was getting ready for a baseball game. It was the first time I had hung out with him and I noticed he kept talking about sex. He put on his athletic cup right in front of me and then kept readjusting his penis. At the time it wasn't that I was afraid, it was just that I didn't really catch on to his meaning. As I look back on it, I think I may have missed a good opportunity.
- age 20, Iowa
As teens, a friend and I masturbated together separately and mutually. Many years later, he was visiting near my city and invited me to join him for dinner and to spend the night at his hotel. When I arrived, I realized his hotel room had only one bed, which made me somewhat uncomfortable. The next morning, he made an overt statement that obviously indicated he wanted to revisit our teen experiences. I left the bed and suggested that if he needed, I wouldn't mind if he masturbated. On the drive home, I thought about what could have been. The thoughts brought back teen memories and did turn me on so much that when I reached my business, I headed straight for the bathroom and had an enormous ejaculation.
- age 61, Oregon
I have always been straightforward with what I want sexually. I go on and say it, and it has happened with both males and females.
- age 15, New York
My best bud and I were off for a few days of rest and relaxation at a cabin in the mountains. We were both in our mid 20s, very close, had discussed masturbation and sexuality issues for years, and at the time, neither of us was in a serious or sexual relationship. At bedtime, both of us had had a couple of drinks and felt pretty good. I started ribbing him about masturbation and was willing to have a mutual session but didn't know how he would feel about that. So, I got up to go downstairs to bed, threw him a rag, and told him to have fun. We laughed and I went off to bed. The next night, he did the same for me. Those are good memories of me masturbating in front of the fire with him downstairs knowing that he'd done the same the night before –, and to this day, I wish we had done it together!
- age 43, Vermont
About 4 years ago, I was swimming with my best friend in his pool. We had been wrestling in the water for about a minute when I got a firm erection. I'm sure he felt it because I had him in a bear hug from behind and all of a sudden he stopped wrestling. I let go and he turned around to reveal a hard erection of his own. We stared at each other for a minute or two before he started to take off his trunks. I freaked out and started to call him a homosexual because I was young and immature at the time. If I had the chance to masturbate with him today, I'd take it.
- age 16, Minnesota
When I was a 19-year-old sophomore in college a guy brought me back to the dorms from a beer and pizza date. The room was empty, so we started necking. He was a great kisser and we both got into it quickly. The kissing was turning to petting, but I held him back because I didn't know when my roommate would return. I could feel his erection hard against me and I wanted to rub him and have him rub me, but I was so fearful of company that I wouldn't allow it. After a while, he left and I never saw him again.
- age 31, New Jersey (female)
When I was 13 and staying at my friend's house, we stripped in the dark. We knew that his parents were watching TV in the living room and the rest of the house was dark, so we crept out past his sister's room and downstairs naked for a thrill. When we had crept around the house for a while and went back to his room he turned on the light revealing that he had been wearing his briefs, and he laughed at my erect penis. He switched the lights back off and started telling me how his penis was much bigger than mine. We both masturbated as we chatted in the dark and I was wishing we could do it together. He masturbated to ejaculation as he described what he was doing. I was yet to have my first ejaculation and I wish I had had the nerve to at least ask him to show me.
- age 26, Wales
Some friends of mine and I were at a Boy Scout camp and started to masturbate to some porn a friend had brought with him. We all took out our penises and started to stroke them, but then everybody just stopped because we remembered a court case having to do with masturbation at a Boy Scout camp and how all those involved were kicked out of Scouts for good. So we all stopped and rubbed ourselves privately.
- age 16, Indiana
When I was 16, I participated in a national orchestra program in Philadelphia where I was the only representative from my music preparatory school, so I had to share a hotel room with another member of the orchestra from a different school. That first night, we were lying in our beds and ready to go to sleep when he asked me if I masturbate. I replied yes, and then he then asked me to show him how I do it. I hesitated for a bit, but then I pulled the sheets back and showed him briefly how I do it (left-handed with my fist). He then asked if he could masturbate with me and I said no, but I'm not sure why. I had masturbated with a close friend in elementary and high school and really enjoyed it. I think it was that I did not know this kid at all and just didn't feel comfortable sharing such an intimate experience with a stranger. (I have never been a fan of casual sex, either.) It's curious that I had no problem showing him how I masturbate; my issue was in sharing the experience.
- age 22, Massachusetts
One night a friend was sleeping over and I awoke in the middle of the night, almost certain that he was masturbating. It was dark, but I thought I saw movement and I definitely heard something. At first, I wasn't sure what to do, but then I knew. I joined in, but we never spoke, and though I couldn't see him, he could see me a little. I wanted to speak up so that we could masturbate mutually, but I was afraid of how he would react.
- age 16, Vermont
When I was 15 or 16, I was at my friend's house after a shopping trip to buy clothes for a party. We were in her room trying them on in front of each other. All of a sudden, she said she wished she had breasts like mine. I felt uncomfortable and said hers were fine, but she persisted, said mine looked so firm, and asked if she could feel me. She did this and I did the same to her. She was the first person, male or female (aside from my parents) to touch me. I felt excited and terrified all at once. We looked each other in the eye, and to this day I'm sure that she wanted to go further as much as I did – but the moment passed, we got on with other stuff, and never did anything like that again.
- age 39, United Kingdom (female)
My friend (who is also 14) and I were play-wrestling in my bedroom and I was very horny. For a couple of seconds it was like I couldn't control myself – I felt his penis, and he was about half-erect. He giggled and gave mine a squeeze, too. We just looked at each other and started laughing and playfully calling each other "gayboy." Then we quit wrestling and he changed the subject. I was about to say something about masturbating each other, but I just let it go. That was about two months ago, and I sometimes regret not going ahead to ask him.
- age 14, Florida
I was going hiking in the wilderness a couple of years ago and a coworker's 18-year-old son asked to come along. On the second day out, we were skinny-dipping in a swimming hole in the middle of nowhere with no one else around. We lay on this big boulder naked, and I noticed that he got a big erection, which caused me to get one, too. I told him to go in the tent and take care of his business while I stayed on the boulder and did mine. We both said we had great orgasms. I would have loved to masturbate him, and I'm sure he would have masturbated me, but I didn't want to betray my coworker's trust.
- age 42, California
My first year after college, I roomed with a girl I'd known from my hometown, but hadn't contacted for the 4 years I was in school. My steady boyfriend was in another city and we wrote passionate letters, including descriptions of how we masturbate, but we didn't see each other often. One Friday, we were both home all evening and the air was tense with sexual frustration. She said my name rather haltingly and then was quiet; I was nervous and didn't reply. About 5 minutes later, she came and stood right next to the sofa where I was sitting and said my name again. I know that if I had hugged her, or even answered, we probably could have at least masturbated together; we both wanted to very much. But I was afraid – maybe because I thought it would change my attitude to my boyfriend. Now, I look back on that night as a missed opportunity to learn something valuable, because I've never masturbated with another woman and I think I'd like to.
- age 55, Missouri (female)
Once when I was 12 or just 13, I was on a camping trip with my Scout troop, tenting with a good friend. I had been masturbating for about a year, but wasn't sure yet if anyone else did it. One night, we both seemed to talk around the subject as we lay on top of our sleeping bags with just our underwear on. We both had boners, but neither acknowledged the other's. I was sure he was hinting about masturbating, but I was too scared to take it to the next step, so we ended up just going to sleep. I think he was just as horny and frustrated as I was. It was okay later, though, because on the next camping trip, he just blurted out that he wanted to masturbate; so we both eagerly got naked and did it. From then on, we were totally uninhibited together and played around a lot. It was great fun, and we did it every time we had a chance to be alone together.
- age 18, West Virginia
When I was about 14, I attended the bar mitzvah for one of my brother's friends at a classy hotel. Midway through the party, they were dancing, but I didn't like that, so I went to the restroom in the lobby. When I went to the stalls, I heard 3 or 4 girls that I didn't know (I think about 16 or 17 years old) moaning in the back, and when I went to check it out, they were all topless and some were masturbating. They looked as if they could have been on drugs and they asked me if I wanted to join them. I thought about it seriously for about two seconds and then just said no thanks and left. It was strange – in a way, I wanted to join them, but again, I didn't. Now, I would kill for that situation to recur because I would try it in a heartbeat.
- age 17, New Jersey (female)
When I was 12, my cousin (two years older than me) and I went to his house while the rest of the family was at our grandparents' house across the street. He showed me a couple of well-perused girly magazines he had stashed in his room and obliquely suggested we both take off our pants. I felt a strange tingling in my groin that was new to me, along with an embarrassing erection. Confused by all this, I got him to show me his video games, instead. Two years later, we walked along a railroad grade, talking about girls, and eventually, our masturbation habits. He said he needed to get off and was going to masturbate on the old railroad bridge, and then invited me to join him. My briefs were soaked, but I felt weird about doing it outside, so I left him to do his business. Every day since, I've regretted saying no.
- age 27, Illinois
When I was 17, I spent a summer working and living with my uncle, who was 28, recently divorced, and needed company as well as some help with his new home remodeling business. After 3 weeks of not ejaculating, I stayed up late one night to watch a porno video I had brought with me. Downstairs where I thought he wouldn't hear, I sat on the sofa and watched the video for about 15 minutes, which got me hard as a rock. Suddenly, my uncle just appeared in the room and I shot up, scared as hell, but he said, "Hey man, calm down – it's okay," and joined me on the sofa. As we both watched the video, he also became aroused and eventually asked, "You (masturbate) a lot?" I said yes, and he told me he had masturbated every day or two since he had gotten divorced. We were both so aroused that I just wanted to pull out my hard penis and do it then and there, but I still couldn't be sure how he would react. In about 10 minutes, he stood up with his penis standing straight up and said, "Well, I really need to get to bed, and I know you need to take care of some things, too." I wanted so badly to go up those stairs and at least listen to him as he masturbated, but I didn't – I stayed there and masturbated by myself.
- age 31, Pennsylvania
My friend was over at my house so that we could keep each other company. Our boyfriends had both worked late this particular evening. After 6 hours and almost as many drinks, our mutual confessions got steamy. We both proclaimed our attraction to each other, and when she said with a sly smile on her face, "So, do you want to try it?" I knew exactly what she meant – but I played dumb to cover my shyness. I could see the moment and the opportunity slipping away even as it was happening, and all I could hear in my head was me yelling at myself, "You IDIOT, why aren't you going for it! " If the chance ever arises again, I will not hesitate.
- age 27, Washington (female)
When I was 13, a friend and I would always shower together after gym class, with nothing sexual about it – just showering. Sometimes we talked about masturbation, but neither of us would admit to doing it. Then one day when we were talking, I got an erection. I think he had one, too, because he was hiding his penis in his hands, which he usually didn't do. We had just admitted to each other that we masturbated, and he had asked if we should masturbate together. But there was almost no time left until we had our next class and I didn't want to be late, so I said we didn't have time. Unfortunately, I started in another school not long after that, so we never talked about it again. I still regret that I said no, because I have only had one mutual masturbation session, and then we didn't touch each other.
- age 15, Sweden
My friend and I had rented some porn. Although we're both gay, neither of us is attracted to the other. When we watched it, I got highly turned on and I assumed that he did, too. I considered suggesting mutual masturbation, but I thought that might make our friendship weird, and I didn't want him to think I was sexually interested in him. Besides, how was I supposed to know if my feelings were mutual? Instead, we went out to my balcony for a cigarette and we talked about how I have phone sex all the time. When he left, I masturbated to the porn.
- age 23, Minnesota
I went over to my friend's house for a sleepover last winter. We were in our sleeping bags in the den, watching some movie on HBO that had naked breasts in it. It was late and his mom and dad had gone to bed, but just down the hall. My friend said, "Lets masturbate," and he even pulled out his erection and started stroking, but we got scared because just then his dad yelled and told us to keep the noise down. We've showed each other our erections before, but we haven't masturbated together yet. I really want to, but we can't find a place to do it where no one would bug us. When it gets warm out, maybe we can camp out in his backyard and do it then!
- age 13, Oklahoma
Several years ago, I was on a business trip and was talking about sex with my roommate. He went to the bathroom, and when he came back I could see he had a partial erection. I went to the bathroom and could see semen on the rim of the toilet, so I knew he had masturbated. At first, I acted as if nothing had happened, but finally, I asked him if he masturbated. He said that sometimes he did, and I confronted him with what I had seen in the bathroom. He admitted it and we talked about it, and how horny we both were. He said he was getting another erection and sure wished he wasn't intimidated by masturbating in front of someone, so I agreed and went to the bathroom to do the deed. I always wondered what would have happened if I had just suggested mutual masturbation.
- age 43, Oklahoma
Once in the gym sauna, I was alone with a man I didn't know. We both sat naked in full view of each other. The man got an erection and so did I. Then he asked something like, "What about a session?" and began stroking. I turned down his proposition, but still watched as he masturbated himself to ejaculation. I felt pretty stupid just sitting there watching with a huge boner.
- age 20, Sweden
Only once, when I was about 13, did I have a chance at mutual masturbation. I had been out exploring the woods with a friend I had known since I was about 5, and we were covered with dirt. His mother wouldn't let us into the house without a shower and told us to clean up together in the basement shower. Reluctantly, we undressed together and turned our backs to each other as we cleaned up. I was quite nervous about getting caught with an erection, but in retrospect, I should have let it get hard and turned to show him, just to see what developed.
- age 57, Ohio
I had a best friend that I met when we were 12 and 13 years old. He was not gay, but I am. When I was 50 and he was 51, he said, "I have never been with a man before, but I trust you enough as a best friend that I would like to try." I said that I had lost friends before by doing this and I didn't want to lose him; his friendship was too important and I couldn't do it. He died 18 months later. Now, I wish I had done it.
- age 54, California
Many times when I was in high school and college I had buddies who were interested in masturbating together. I wanted to also very much, but at that time of my life I still thought I was the only guy who wanted to do it together with a male friend. It was only years later that I was able to look back and recognize that their words and actions really were attempts to get the action going. How I wish I could go back in time with what I know now! I couldn't believe then that other guys actually did masturbate, too. You younger guys should go for it. Don't miss out on the fun.
- age 37, Hawaii