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How do you "break the ice".....

I'd suggest not talking about tickling, getting to know them instead of jumping straight into the tickling.
 
I know what you mean. Just because you know someone doesn't mean the first session is gonna be without awkwardness.

When I met someone for our first session, he came over and we just kind of sat around and talked for like an hour. We knew one another fairly well already and had had several conversations so we had a good idea what kind of topics would yield comfortable, easy conversation. After that we went out to lunch, and spent another hour or so at the diner, talking more - almost all non-fet related stuff. Giving ourselves that time to get comfortable in eachother's presence was really helpful for me, and made me feel more like I was getting ready to play with a friend, not just have a pervy session with some stranger.

When we got back to my house we kinda sat around for about 5 minutes or so, and it was like the elephant in the room. As usual, my inner smartass solved everything 😛 I said something to the effect of, "Do you want to let your belly rest before I destroy you? I don't want you throwing up your lunch or anything," and that was it 🙂 The next few hours were super awesome and not awkward at all.

Basically don't be in a hurry to get down to business. If we had jumped right into it as soon as he got here I don't think I would have had nearly as much fun. Get comfortable with eachother. Your session will be better for it.
 
I'd recommend meeting and hanging out for a bit. Go out for a drink, or if you're not into drinking, maybe a coffee or something. Being in a public atmosphere helps loosen things up because you don't feel like you're totally one on one with the person if other people are around. If you do stay with the person alone, maybe throw in a dvd or something and watch it and try to strike up conversation. Immediately talking about tickling comes off kind of strong, like basically you have nothing else of interest but the fetish.
 
I met my only tickle buddy at a bowling alley. We of course had been talking for a long time so we had things to talk about other than tickling stuff. We had made a bet over who gets tied and tickled first and that helped break the ice.

Just think of them as new friends! That's why I never have any interest in meeting up with someone who I have no interest in talking to about things outside of tickling. It allows you to far more easily become comfortable with the person. Hell, by the next morning, me and my lil tickle friend had an actual tickle fight on my bed (and NO we weren't on the bed because we had shared it the night before! It was completely innocent 😛)! It was the funnest experience ever. She did later admit she wasn't exactly trying hard to get the upper hand on me (she's a lee mainly 😉 ) but it was still just amazingly fun.

To me, it's just no fun to meet someone who you haven't talked to enough and gotten to know enough and just plain ol like as a person enough that you cant lay on the ground or on a couch or bed with them smiling and trying to catch your breath from a tickle fight!
 
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