WHAT IS THE MOST DIFFICULT POSITION YOU'VE MASTURBATED IN MORE THAN ONCE?

[Notes: By far, the most frequently mentioned "most difficult" position, reported mostly by males, was the headstand. The object is to masturbate upside down with your penis positioned more or less over your face or mouth, so as to taste your own semen as it comes out. Apparently, many males turn on to the idea of eating their semen *before* they ejaculate, but afterwards, the desire fades quickly. So getting into this position gets the semen into the mouth as quickly as possible. A similar position is a kind of inverted somersault that places the penis and face into much the same relationship. Some males who have sufficient flexibility and penile length reported enjoying autofellatio, even if they can reach only their penis with their mouth. Other males reported masturbating while standing as their most difficult position, finding it difficult to achieve orgasm. Females mentioned the difficulty of positioning their genitals under a bath faucet or shower spray for stimulation. Masturbating in other positions where the clitoris is hard to reach was also frequently reported: on all fours, standing, and in public or semi-public places where movement is constrained.]

Why would you want to get into a difficult position to get the best experience? I wouldn't want to do that!
- age 25, India

I sometimes masturbate while sitting up straight, and then at the last moment before I climax, I stand up. It gives me a great weak-in-the-knees, light-headed feeling!
- age 17, Alabama (female)

My hardest position is to put my legs up in the air so I can ejaculate into my mouth. Most of the times I've done this, I've used the wall to hold my butt and legs up, but a couple of times I've done it without support. The advantage is the variety from my normal masturbation techniques and the anticipation of getting my semen directly into my mouth. That's a turn-on for me, since if I ejaculate onto my stomach, I am already done with orgasm before I can taste it. By then the excitement is gone.
- age 52, West Virginia

It would have to be masturbating in a phone booth. I get a thrill out of people being able to see me.
- age 15, Missouri (female)

I know this sounds weird, but it just shows what horny males will try at least once or twice. The position is sort of a lazy handstand against a wall. I was trying to see if I could give myself oral sex. I lack about an inch in either length or flexibility to be able to do it, and although it wasn't painful, it was so awkward and uncomfortable I couldn't keep it up. I don't recommend it to anyone.
- age 47, Arkansas

Standing up. It takes forever to finish, and I'm tired the whole time. I do it like that only when I'm in a situation where I cant lie down.
- age 14, North Carolina

About 5 years ago I did it while I was standing on my head because I heard it makes orgasms stronger. Well, I strained my darn neck muscle and ended up in the hospital because I passed out when all the blood went to my head. Now I have severe arthritis in my neck, but the orgasm was great — I think.
- age 73, Utah

My most difficult position is "The Little Mermaid" [JackinExpert] because my penis does not stay between my legs. It pops out. I think the lube makes it do this.
- age 17, California

I have masturbated more than once in the laundry room at my apartment complex. I remove my pants and boxers and get up onto the washing machine while it is running. I have the lid open and let the spinning drum rub, spin, and vibrate the area from my anus to my testicles. It's a difficult position to get into, but it gives me the most mind-blowing orgasms I have ever had. The added thrill of someone walking in and catching me makes the orgasm even better. Fortunately, the door to the laundry does lock. So I have a few seconds to recover if someone does rattle the handle to get in. [Warning from JackinWorld: DO NOT try this at home!]
- age 32, Canada

Mine is "doggie style." This is difficult for me because of the angle of my hand. I can't get my fingers into my vagina, and I find it hard to reach my clitoris. But it always feels incredible when I do find the right way to touch my clitoris, and I get an amazing orgasm every time I do it in that position.
- age 17, New York (female)

Hanging upside down from a trapeze. Try it! You might like it.
- age 35, California

On a pillow. I roll it into a ball and then lie on it and rub my crotch on it. It's strange because my hands are crossed underneath me to protect my breasts when I'm on the floor. It feels so good, so soothing. The best advantage is that it's not messy and that you get a great exercise — especially with your voice when you moan!
- age 16, Delaware (female)

When I was 18 I served aboard an aircraft carrier, the USS Forrestal. I spent 3 months doing skullery (mess) duty (12 hours on, 12 off), work related to feeding 6,000 guys at sea. Doing this required my transfer to a different sleeping area where other guys were around me all the time. So I had to masturbate without *any* visible movement (pumping) or sound (moaning)...quite a challenge. I developed a way of feeling myself to orgasm. It involved rapid touching and caressing using only my fingers. It worked well and felt great!
- age 55, Illinois

Whenever I start to get an erection at a bad time, I stand up to make it stop. This keeps me from having to stand up when I am fully erect and embarrass myself. I have found that whenever I stand up, my erection goes away. It makes it difficult to reach an orgasm when I am standing, so masturbating while standing up is the hardest position for me. The advantage to this position is I can do it in the shower, where I don't risk getting caught and I can clean up easily.
- age 14, Colorado

When I was a teenager, I used to go down in the basement and grab the banister from the other side of the staircase and do chin-ups while letting my penis (inside my briefs) rub against the wall. The orgasm was spectacular, but it was a lot of work. I would do it at least 6 times a week, and it kept me in shape.
- age 28, Ontario, Canada

That would have to be in the driver's seat of a car during a traffic jam. The seated position doesn't allow for much access to the vagina with a vibrator, and I can't do a lot of shifting due to my not wanting other drivers to know what I'm doing.
- age 19, South Carolina (female)

I was in the trunk of a car. My brother has always picked on me (playfully — it was only a joke). He locked me in the trunk of our car and said, "I won't be back for an hour!" I was kind of ticked off at first, but then — I don't know why — I just decided to masturbate. I unzipped my fly and ejaculated into my pants so I wouldn't make a mess. When he came back he said with a smirk on his face, "Did you have fun?" I said, "You bet I did." There is definitely no advantage to this "position" I just did it for the heck of it. [Note: The Question asked for a position you've done more than once, but good enough.... -Ed.]
- age 15, Oregon

On my stomach. I put a pillow underneath my belly and hips, and insert my dildo. It's hard to reach my arms underneath me to stimulate my clitoris, but from that position I can thrust my hips more, which makes me feel like I'm working to reach my orgasm. The harder I thrust the more my dildo moves and the more intense is my orgasm. I use this technique only every few months because I get exhausted afterwards. It's a nice release of tension.
- age 19, Massachusetts (female)

Sometimes I masturbate with my legs over the back of a recliner, so that my head is in the seat and my butt and upper legs are against the back of the chair. I think it's wonderful, because it limits my movements, forcing my penis to express all of the good feeling and intensity. It also lets me ejaculate without touching my penis, so that after I finish ejaculating, I can grab my penis and pump a few more times for a second orgasm!
- age 23, Texas

For me, it's most difficult to masturbate next to my wife when she's asleep. There is the added risk of getting caught. I pull the blankets off her, exposing her breasts when she's facing me, and seeing the outline of her buttocks when she's facing away. So, I can still get it when she doesn't want it.
- age 28, Iowa

At school, I did a handstand in the shower and leaned against the wall, supported by only one hand and the side of the wall. I pointed the shower nozzle over my vaginal area and masturbated at the same time. The orgasm was *so* intense.
- age 15, Ireland (female)

It can be very difficult, if not stupid, to masturbate while driving down the highway — but I have awesome orgasms and ejaculate large quantities of semen due to the thrill of it all.
- age 19, Canada

I suppose the most difficult and awkward position has to be the couple of times I've tried to stimulate my prostate and masturbate at the same time. I wrap one arm around my backside so I can work a finger into my rectum to massage my prostate while using my right hand to masturbate. It was difficult to do and uncomfortable, too.
- age 46, California

I begin in a kneeling position and then lie back with my calves against my thighs and back flat on the bed. I like this because it stretches my thigh, leg, and stomach muscles. Something about tightening my thigh and butt muscles just makes the orgasm more powerful and last longer!
- age 27, Canada (female)

It feels really good to suck on my big toe while I masturbate. My feet are very sensitive and sensual to me. I think the more places you stimulate, the better. After over 30 years of masturbating, I'm still discovering new things about my body.
- age 46, Colorado

Masturbating while standing on a stepladder, trying to be quiet, and peeking at my sister in her bedroom as she's getting dressed or walking around nude. I had started to peek in my sister's room when I was around 13 or 14 and just never stopped. That first time, I was in a tree outside and saw her in the nude by accident. We have an aluminum stepladder that can be noisy, so I must be careful with it. I get the ladder from the garage, go quietly to her bedroom window, and watch her as I masturbate. She is two years older than me and kind of chunky, but she has huge breasts and nice-looking pubes. I get horny just thinking about it.
- age 17, Maine

The only position I consider difficult is when I get the urge and try to masturbate while driving. I am a safety nut and always wear my seatbelt, especially on the highways, and it's tough to work around the belt when dealing with zipper, buckle, and johnson all at once. Okay, I know, it sounds strange — a safety nut masturbating while driving! But what can I say? When ya gotta, ya gotta!
- age 39, Ohio

I've found that on my knees with my legs about one-and-a-half feet apart, I can put my dildo on the ground and let myself control its penetration. It's a good position because it's very similar to the female-superior position during actual sex, which is my favorite.
- age 16, Oregon (female)

Probably standing. I have started practicing masturbation in the shower because I'm going away to a university soon. Since I will be living in a dorm with a roommate, I plan to take care of myself in the shower. I can't seem to get the hang of it yet. I'm so used to sitting or lying back that I start to hunch over in the shower so I'm in a position similar to sitting. The main advantage is that when I finally ejaculate, the orgasm is really intense as I let the water hit my penis!
- age 18, Canada

I have been blessed with the ability to suck my own penis, even if only the head. My back gets a little sore after a while, and I have never been able to reach orgasm on oral stimulation alone. So I usually have to masturbate by hand until I'm close to ejaculation, then roll onto my back and finish the job. Even though I can't get the shaft in, ejaculating into my own mouth is probably the best sensation ever. And to you jealous guys who say autofellatio is gay, I have this question: You masturbate with your own hand, right?
- age 14, Maryland

When I was in college I had large, boring classes and would sometimes get horny during the lectures. So with difficulty, I taught myself to achieve orgasm by pressing my textbook into my crotch in the area of my clitoris and just barely moving it. It took a long time, and I had to really be careful how much movement I was making, but it was definitely worth it. This difficult position had the advantage of letting me masturbate in public without anyone guessing the reason for the big smile on my face!
- age 28, Canada (female)

When I was younger, I masturbated upside-down in my garage by hanging from the rafters. The blood would rush to my head increasing the feeling.
- age 24, Massachusetts

When I'm having sex with my boyfriend, we like to do it "doggy style". Then I usually massage my clitoris while I'm on all-fours. That is pretty hard for me, since I'm used to lying on my back.
- age 20, Norway (female)

Why make it difficult to enjoy yourself? Masturbation should be fun and relaxing, not a damn math test.
- age 16, United Kingdom