Once or twice. I was in the shower and had been stroking for nearly 20 minutes without ever even approaching the "boiling point," as I like to call it. For most of the time, it just felt like a mildly pleasurable tickle. Ultimately I gave up.
- age 14, Oregon
Two years ago I worked part-time in a convenience store that wasn't very busy with customers. I would usually skate in the parking lot when things got really slow, but it was raining that day. I was very bored and bothered by an erection, so I decided to go in the back room to entertain myself. Everything was fine at first. I thought how cool it was getting paid to do this on my time. But about 2 seconds before I was going to ejaculate, I heard a customer walk in and yell, "Anybody here?" It wasn't that they saw me or anything, but it really ruined the moment. I was too paranoid to finish, but later I found I could get away with locking the front door.
- age 24, Pennsylvania
I can't recall exactly when it happened, but it was like my 5th session for the day (a particularly horny day for me) – and it really felt uncomfortable and made my testicles hurt afterwards. The session lasted nearly 30 minutes, but there was hardly any pleasure. I lost my erection several times, and it was just a huge effort to achieve a very pitiful orgasm. I guess that just came from overuse. Everything was back to normal after a good night's sleep.
- age 16, Australia
Only once – I was in the hospital after I had broken my leg. I had a lot of pain and was woozy from all the drugs, but nonetheless I was wildly horny! My mind wouldn't stay concentrated on masturbating (because of the drugs), and I couldn't get in a comfortable position as I neared orgasm (because of the cast) – but the need for release won out over everything, and I finally ejaculated. Though I can't say I enjoyed the session, I've never been more thankful for the results!
- age 26, California
I was about 12, and I was way into the "pillow humping" thing. One day I decided to hump my bed quilts. I was totally naked except for my socks. So I humped and I humped and I humped – it felt so good I just couldn't stop! I went for about half an hour and was sweating like a pig. About an hour later I looked down at my penis and found that I had kind of grazed the skin a little. It hurt whenever I took a pee, and I sure didn't hump my bed sheets again!
- age 14, Australia
I learned to masturbate at a very young age (6 or 7), and from the beginning I enjoyed delicious orgasms but without ejaculating any semen. At age 14 my somewhat delayed puberty began, and just at the time of my greatest hormonal horniness, something went terribly wrong. Every time I tried to masturbate, as my climax approached and I was aching for release, my ejaculatory spasms would begin just before my orgasm. The result was a few drops of clear juice, but no orgasm! This left me more in need of release than when I started. This dreadful condition plagued me for one full year. I was too afraid to discuss it with anyone, but at last I had a properly timed orgasm and produced a ton of thick, white semen. Sex and masturbation has been great ever since, but for one year it was torture.
- age 51, California
Once, after my girlfriend dumped me, I tried masturbation as a stress reliever. Unfortunately, at the moment of orgasm, I pictured her face and got really depressed, thus ruining the orgasm and the whole session.
- age 16, Massachusetts
When my wife and I were dating, we decided not to have sex until after we were married. However, we did masturbate each other. On one occasion, I had masturbated so much before we got together that my penis was sore. Later that night we started petting, and she decided to masturbate me. I wanted it so much, but at the same time I was sore. Eventually I ejaculated, but I never did tell her how much it hurt.
- age 27, Maine
A couple times when I first started masturbating. I felt really guilty, because I didn't understand that masturbating is okay. It had nothing to do with my family; I just had a few really bad teachers (I go to a Catholic school) who taught that anyone who masturbated was evil. (And no, this isn't the view of all Catholics, thank you very much.)
- age 14, Canada (female)
Although I can't name a specific session, it seems whenever I masturbate more than I normally do in a day (my average is 1 or 2 times a day) I get a dissatisfying feeling after I ejaculate...not like guilt, but more of an "Okay, what was the point of that?" feeling.
- age 17, California
My girlfriend and I masturbate while chatting in our private chat room. We tell each other what we're doing and get very graphic. The other night we were both getting aroused. There were several periods where she wouldn't type anything, and I did the same. I would type a few words and then stroke for a while. I assumed she was doing the same thing, typing and then massaging herself. I was just about to ejaculate when she came onti the screen saying, "I'm sorry, honey – I was looking for a pattern on how to make potholders out of old washcloths." That killed it for me! I'm looking for a new girlfriend.
- age 70, Georgia
I had to sell my chihuahua recently and the day he left, I was very sad. That night I was also very horny. So I masturbated and cried, and when I finally ejaculated, it was very unpleasant. It felt like a chore.
- age 15, Missouri
Once I was masturbating on the stairs. I found it quite exciting at first, as our front door is just at the bottom. Anyway, as I ejaculated, the orgasm was so strong that I actually fell down the stairs, spraining my wrist and ankle. I wouldn't recommend this method to anyone – it's DANGEROUS!
- age 19, United Kingdom
When my ex-boyfriend told me he had cheated on me, I turned to masturbation for a sort of comfort. I was so upset, crying and shaking, that I took no pleasure from it, only sadness.
- age 18, Illinois (female)
Once – during my orgasm, I heard a loud crash of thunder. I was scared, and the orgasm turned out kind of weak.
- age 17, Massachusetts
I wanted to taste my sperm. I tried my "pre-cum" before and I liked it, so I thought sperm was going to be the same. I always said to myself, "Okay – I'm going to do it this time," but after ejaculation the desire was gone. So one time I aimed my penis to my mouth, and when I ejaculated I had a mess in my face and the taste was awful. I hated that session.
- age 20, Dominican Republic
One time I didn't enjoy a session because it was taking forever. It was particularly enjoyable for a while, but then my arm started hurting. Afterwards I found out why – I had created a blister or sore of some sort because of the friction, and it was very tender. I couldn't masturbate for a week. I found afterwards that it was a godsend, because when they went away I did it and it was the best orgasm I had had in a while. Went all the way to my toes, and I must have emptied a gallon onto myself before I was done.
- age 16, Ohio
I didn't like one masturbation session because I used soap, and it really burned the inside of my penis.
- age 17, Arizona
I went through a phase in my life where I would masturbate and as soon as I ejaculated I'd get a migraine headache. I would just sit there, semen all over myself, holding my head trying to make it go away. But it's always better than nothing!
- age 18, Georgia
While masturbating with my girlfriend.
- age 26, Maine
"My sister walked in on me when I was using a can of dog food.
Now she thinks I'm a freak."
Just last month my older sister walked in on me when I was using a can of dog food as a masturbation tool. I heard a joke about it at school and couldn't get it off my mind, so I tried it. It was really bad – the meat had a nice feeling, but it reeked. Now my sister thinks I'm a freak, and I don't know what to do.
- age 15, New York
I had some kind of infection, and it hurt when I ejaculated. It went away pretty fast, but it was scary. The doc said it was non-specific urethritis (not sure of spelling) from bacteria getting up my urethra. He suggested I should not masturbate with spit.
- age 20, Washington
I made a bet with myself that I was going to try to masturbate 7 times in one day, and if I lost I would not be able to masturbate for a month. I started that day with pleasurable sessions – the first, second, third, and even the fourth were quite nice, but the fifth, sixth, and seventh were terrible. I was so sore and chafed I thought I was going to die!
- age 16, Ohio
One day I had a slight headache. I thought masturbating would make me feel better...at least in one area of my body. But when my ejaculation hit, BAM! It was like someone hit my head with a sledgehammer. My headache intensified when my muscles tensed for orgasm, and the pain was blinding for a couple of minutes before it began to subside back to a dull ache. That was the worst orgasm of my life. Now I never masturbate if I have even the slightest headache.
- age 36, New Hampshire
My boyfriend, whom I totally trust, really likes to masturbate me – but it always seems like no matter what he does it's totally unenjoyable for me. I can barely even get aroused, even when I tell him exactly what to do.
- age 15, Canada (female)
One time I began masturbating all horny and ready for a good session. I decided to take my time. After about 20 minutes my older brother walked in on me. I was lying naked on my bed with penis in hand. He said, "Have fun," and walked out. I was a little embarrassed, but I kept on going. I decided to use some lube, and it kept evaporating, so I'd refill. The last refill was a little too much and made quite a bit of noise. I sped up the tempo right before ejaculating, creating more noise than I thought. My mom walked in right after I ejaculated and said "keep it down, we're trying to sleep." It wasn't the session I didn't enjoy – it was the embarrassment.
- age 18, Illinois
When I was younger, an older male cousin and I masturbated each other. When we were finished I felt guilty and ashamed of what we had done. I don't feel this way now, but at the time I think it was to much for me to handle.
- age 16, Ontario, Canada
I can remember one time during the school year when I woke up a little late in the morning. As if that wasn't bad enough, I was also very aroused for some reason. I didn't want to go to school with an erection, so I figured I would masturbate really quickly. This was the most unpleasurable session I've ever had, because my orgasm was not even noticeable. I would say that's the only session I really didn't like, and only because I was rushing myself.
- age 18, Connecticut
When I had mono...mainly because I had mono.
- age 17, Iowa
All I'll say is that earlier in the day I had been chopping jalapeno hot peppers, and my hands must have still had some of the "heat" from the peppers (even though I washed them), and it really burned. By the next morning everything was fine.
- age 21, Canada (female)
I'm about to be able to laugh at it, but a couple of years ago I was talked into masturbating in front of 2 girls. I did it hoping to see them do it, or at least to see them naked. I was really getting into it – I had my eyes closed and was making faces. They started laughing watching me. At first it didn't bother me all that much, but I watched them making faces and making fun of me. I had it and left before I orgasmed. I got home, embarrassed and all, but I had to finish masturbating. It felt terrible, but it was relief. I still catch sh*t from those girls and some others they told.
- age 16, Texas
Once while I was masturbating my dog walked in the bathroom. She just stared at me as I was beating it. I chased her out, but the masturbation was no fun.
- age 14, Michigan
These sessions are few and far between, but they do happen. For me the most distinct time was when I first began masturbating. The guilt and disgust I felt after masturbating was enough for me to shy away from wanting to do it. Thankfully JackinWorld came along and taught me there's nothing to feel bad about.
- age 15, Idaho