Well here's a conversation you probably don't have every day. I reached out to friends, which immediately became much closer friends, and asked them about the strangest thing that's ever done the job for them. Honestly we all went through that weird phase where everything is kind of sexual and you're just a big ball of horniness at all times. If anything, this should make you feel a lot less embarrassed about your own little, private adventures.
![What's The Strangest Thing You've Ever Masturbated To]()
1. "Remember water snakes? Those toys that were like squishy tubes filled with liquid that you could stick your finger in? I made love to one of those. It was like a junior Fleshlight. The best part is that it was my friend's little brother's toy and I never told him what I did with it."
2. "Ok, this is weird, and I'm only sharing it because my name isn't going with it. My parents bought a camcorder, for what I assume was to make sex tapes of their own. I assume that because it was set up on a tripod in their room. One day when no one else was home I took the camera and set it up in my room and recorded myself masturbating. Then, and here's the really weird part, I wait a little bit and jerked off to the recording of me jerking off from earlier. After it was over I recorded over the tape and obviously never brought it up to anyone ever again."
3. "Back before you had the internet to be your instant smut provider, we had to be creative. I got off so many times arranging Barbies and action figures together in sexual positions. I was like a tiny pornographer for plastic models."
![What's The Strangest Thing You've Ever Masturbated To]()
4. "The very first time I ever did it, I actually didn't know what I was doing. I didn't realize THAT was what masturbating was. I was lying on the floor in my room going to town on myself to a scene on "Mad About You" where Helen Hunt was brushing her teeth. I'll never forget that moment."
5. "Once when I was 12 I was on a trip with my grandparents in a cabin in the middle of nowhere. I had my own room and was constantly dealing with boners, so I used the only sexual stimulant I had; the small, somewhat sexual moans Shania Twain made during her hit single "Any Man of Mine." I had it on tape and just listened to it on my walkman over and over until I finished. Certainly not my proudest moment."
![What's The Strangest Thing You've Ever Masturbated To]()
6. "Petroleum Jelly was a stereotype of things you'd use to masturbate with, but we never had any in my house. So on a trip to my grandma's house I noticed a jar of it in the cabinet. Instead of putting some on my hand and using it that way, I just turned the can sideways and started thrusting into it. I'm sure she was puzzled by the random pit in the middle of her ointment, but thankfully no one ever mentioned it to me."
7. "I don't have anything weird that I masturbated to, but one time a guy convinced me that we could use ketchup as lube. Let me just say that I do not recommend using ketchup as lube. I'll leave it at that."
8. "One time I stayed up until 4am because there was a movie on HBO where a woman was talking and her dress came down just a little, so you could see her nipple. I stayed up hours just to be able to jack off to that. You kids had better be thankful for what you have now. Those were dark days."
![What's The Strangest Thing You've Ever Masturbated To]()
9. "I don't think I ever actually masturbated to it, but man let me tell you, as a teenager in the late '90s you could easily find some seriously messed up stuff on the internet. I would use IRC to exchange pictures with these server bots and I saw so many things that PornHub couldn't even fathom today. I don't want to go into detail, but I've unintentionally seen way too many animals having sex with people."
10. "I used to do it all the time to my VHS copy of "The Little Mermaid," but not to Ariel. I would do it to Ursula. There was something about those big, busty naturals that really did it for me."
11. "I can jack off to someone's Instagram even if there are no sexually suggestive pictures whatsoever. You know how those detectives on TV can visualize how a murder went down without actually seeing what happened? That's what I can do, except with visualizing boobs. It's a gift and a curse."
![What's The Strangest Thing You've Ever Masturbated To]()
12. "For me it's probably the Tonya Harding sex tape. I deserved better than that. It was not a good performance by anyone involved."
13. "So this isn't a weird thing I masturbated to as much as it is a weird path I chose to get to the masturbating. I was going on a road trip with my dad to my uncle's house for the weekend to watch the Super Bowl. On the way there he stopped at a gas station and bought some dirty magazines. He thought I didn't see them, but I saw them. So when he wasn't looking I took one and put it inside the lining of the sleeve of my coat. I put it down on my forearm so you couldn't really tell anything was there unless you touched it. I hid that thing in there for THREE WHOLE DAYS! I don't want to be a drug smuggler, but from that experience, I think I'd be a pretty good mule."
14. "Princess Lolly from the Candyland game. We didn't have a lot of options back then, ok?"
![What's The Strangest Thing You've Ever Masturbated To]()
1. "Remember water snakes? Those toys that were like squishy tubes filled with liquid that you could stick your finger in? I made love to one of those. It was like a junior Fleshlight. The best part is that it was my friend's little brother's toy and I never told him what I did with it."
2. "Ok, this is weird, and I'm only sharing it because my name isn't going with it. My parents bought a camcorder, for what I assume was to make sex tapes of their own. I assume that because it was set up on a tripod in their room. One day when no one else was home I took the camera and set it up in my room and recorded myself masturbating. Then, and here's the really weird part, I wait a little bit and jerked off to the recording of me jerking off from earlier. After it was over I recorded over the tape and obviously never brought it up to anyone ever again."
3. "Back before you had the internet to be your instant smut provider, we had to be creative. I got off so many times arranging Barbies and action figures together in sexual positions. I was like a tiny pornographer for plastic models."
4. "The very first time I ever did it, I actually didn't know what I was doing. I didn't realize THAT was what masturbating was. I was lying on the floor in my room going to town on myself to a scene on "Mad About You" where Helen Hunt was brushing her teeth. I'll never forget that moment."
5. "Once when I was 12 I was on a trip with my grandparents in a cabin in the middle of nowhere. I had my own room and was constantly dealing with boners, so I used the only sexual stimulant I had; the small, somewhat sexual moans Shania Twain made during her hit single "Any Man of Mine." I had it on tape and just listened to it on my walkman over and over until I finished. Certainly not my proudest moment."
6. "Petroleum Jelly was a stereotype of things you'd use to masturbate with, but we never had any in my house. So on a trip to my grandma's house I noticed a jar of it in the cabinet. Instead of putting some on my hand and using it that way, I just turned the can sideways and started thrusting into it. I'm sure she was puzzled by the random pit in the middle of her ointment, but thankfully no one ever mentioned it to me."
7. "I don't have anything weird that I masturbated to, but one time a guy convinced me that we could use ketchup as lube. Let me just say that I do not recommend using ketchup as lube. I'll leave it at that."
8. "One time I stayed up until 4am because there was a movie on HBO where a woman was talking and her dress came down just a little, so you could see her nipple. I stayed up hours just to be able to jack off to that. You kids had better be thankful for what you have now. Those were dark days."
9. "I don't think I ever actually masturbated to it, but man let me tell you, as a teenager in the late '90s you could easily find some seriously messed up stuff on the internet. I would use IRC to exchange pictures with these server bots and I saw so many things that PornHub couldn't even fathom today. I don't want to go into detail, but I've unintentionally seen way too many animals having sex with people."
10. "I used to do it all the time to my VHS copy of "The Little Mermaid," but not to Ariel. I would do it to Ursula. There was something about those big, busty naturals that really did it for me."
11. "I can jack off to someone's Instagram even if there are no sexually suggestive pictures whatsoever. You know how those detectives on TV can visualize how a murder went down without actually seeing what happened? That's what I can do, except with visualizing boobs. It's a gift and a curse."
12. "For me it's probably the Tonya Harding sex tape. I deserved better than that. It was not a good performance by anyone involved."
13. "So this isn't a weird thing I masturbated to as much as it is a weird path I chose to get to the masturbating. I was going on a road trip with my dad to my uncle's house for the weekend to watch the Super Bowl. On the way there he stopped at a gas station and bought some dirty magazines. He thought I didn't see them, but I saw them. So when he wasn't looking I took one and put it inside the lining of the sleeve of my coat. I put it down on my forearm so you couldn't really tell anything was there unless you touched it. I hid that thing in there for THREE WHOLE DAYS! I don't want to be a drug smuggler, but from that experience, I think I'd be a pretty good mule."
14. "Princess Lolly from the Candyland game. We didn't have a lot of options back then, ok?"
