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My (hypothetical) first session (f/m)

Ticklish OH Guy

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Aug 18, 2008
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This is my first story about what I envision my first tickling session might be like. Sorry if I missed some typos or things like that, I'm not much of a writer. I hope you enjoy it.

Nervously I enter your house. You can immediately tell I’m not quite sure what to expect since this is my first real tickling experience so you offer me something to drink. After some small talk I begin to feel a little more at ease, no longer wondering if this was a mistake. Almost at the very second I begin to relax and let my guard down you ask me if I’m ready for the real fun to begin.

I sheepishly nod and follow you to your room where I see your bed with the Velcro straps already out at each corner. We both begin by taking off our shoes, but you tell me to leave mine on. You want my feet to stay warm and sensitive until you are ready for them, plus as I’ll realize later, you enjoy slowing teasing and tormenting me by removing my last bit of protection yourself.

So I lay down as you strap my ankles spread out at either side of the bed. Pulling them tight, you ask me if I’m comfortable, I say I am. As you fasten my wrists above my head the reality of my vulnerability begins to really sink in. I test the bonds and realize I can move a little bit, which helps, but you tell me that just won’t due and make the adjustments accordingly. Now I am truly immobile, truly your ticklish little play thing, there for the taking.
You lean in close and say reassure me one last time that you promise to respect my safeword, and ask me to trust you. You promise not to push me to far, but still give me the tickling of my life.

You then take your position on the bed, straddling my waist, and place your fingers gently on my ribs. As you do, you lean over a little, careful not to put any pressure on me so not to tickle, and whisper to me, “Now just try and relax…. This is going to tickle”

With that I close my eyes and brace myself for the attack…. But it doesn’t come. Afraid to open my eyes or speak I just lay there for a second, 10 seconds, 30 seconds go by but nothing. Finally the anticipation becomes worse than the actual tickling and I look up and meet your eyes staring down at me.

“Boo” Is all you say and begin your ticklish assault on my ribs. I was wrong, the tickling is so much worse than the anticipation. I am a laughing, blabbering fool in a matter of seconds. You work your way up my ribs and to my armpits, which only makes it worse. I begin to beg and plead for you to stop, offering to do anything and everything you could ever want for a break. You tell me that my ticklish body open for you to play with is everything you could ask for and continue your assault on my ribs and armpits.
After what feels like an eternity you decide I need a chance to catch my breath, but you don’t want the fun to stop all together. So as I’m trying to suck in as much air as I can you decide to throw an old tee shirt over my eyes so I can’t see and playfully, randomly poke at my ribs. No enough to make me full out laugh, but enough to keep me uncomfortably squirming under your fingers as I try and recover from my tickling you gave me.

After a much too short break you decide it is time for the “fun to continue.” You reach up, remove the tee shirt so I can see again, give me a kiss for good luck, and once again begin tickling my sides. But this does not last long, you tell me its time to see if my hips are ticklish. You ask me, “What do you think? Do you think your hips will be as ticklish as the rest of you has been so far?” Still giggling and trying to catch my breath I answer that I feel like, at this point, its no longer a matter of if, but how much.

You seem to enjoy my somewhat defeated answer because you laugh and respond, “Very well, let’s discover how much then.” And away you go, digging right into my hips. Now having not ever been tickled there I wasn’t exactly sure what to expect, and I definitely wasn’t prepared for the torture that came next. I thought it was bad before, this was the definition of tickle torture. It tickled more than anything I have ever experienced. I let out a couple cried for mercy, mixed in with a couple, “please, no more”s before I was overtaken by silent laughter. I felt even more helpless, unable to beg for you to stop I was forced to try, unsuccessfully, to buck you off, even for a second to get a short break.

You realize that I’m quickly beginning to lose it and you stop, promising that if I’m a good boy for the rest of our time together you will leave my hips alone. I try and say thank you but I’m still laughing and catching my breath so I just nod at first.

You offer my some water which I gladly drink. I begin to relax again, thinking that this was one crazy experience, but one that was done now. I thank you again for somehow finding a balance of being gentle and pushing me further that I thought I could go. You chuckle a little to yourself and tell me that you’re glad I felt this way, but we weren’t done yet. You haven’t had a chance to explore my feet yet.

I, of course, knew this too, but I also knew that my feet were my most
ticklish spot. I’ve never let anyone tickle my feet for more than a second or two because I couldn’t handle it, it was just too much.
You make your way down to the foot of the bed where a chair waits for you to sit in it. You ask me which I would prefer, to have my feet tickled separately, or at the same time? I must have taken too long to answer because as I was trying to decide which would be worse you decide for me. “Well since you don’t seem to have a preference I think I’ll do both, I wouldn’t want to disappoint you.” I quickly say that it wouldn’t at all be a disappointment and that it would be more than enough if she just tickled them both at the same time (I never thought I would actually ask someone to tickle my feet). But you insist that it wouldn’t be fair if they didn’t get the individual attention the each deserved.

You then place yourself in front of my right foot, and slowing untie it and loosen the laces. This anticipation is so much worse than the beginning, I nervously move my foot around once the shoe comes off. You tell me you don’t want to be fighting me the whole time, so you make me a deal. “If you try your very best not to move your foot while I tickle it and you do exactly what I say when I say it, I will go easier on you and I won’t go back and tickle your hips again. Does that sound fair?”

I really don’t know if I could handle you tickling my hips again after this foot tickling I’m about to endure so I really don’t have much of a choice. I agree to your rules. You then slowly peel the sock off my foot, allowing the cool air to touch it. Even that slightly tickled me during this heightened sense of ticklishness this anticipation has built.

You tell me to hold me foot still and try not to laugh. You promise to begin with some really light tickling to start with. You place just one right underneath my pinkie toe and slowly drag it underneath all my other toes and then down my arch to the heel. While this tickles terribly I manage to hold my foot still and fight back the laughter. You say you’re proud of me and you want to try it again. You do, but this time your finger doesn’t stop at my heel but swirls its way back up my foot. It somehow tickles more the second time, but I again manage not to move or laugh. You tell me that I must not be as ticklish as I thought so this time it would be two fingers and they won’t stop until I start laughing, but you want me to hold out as long as I can. While this seems like a game I can’t win, I know it is far better than the all out tickle assault that you could launch against my feet at any time so I play along.

I make it about two more times of you just slowing dragging your fingers up and down my feet before the ticklish sensations build up and are more then I can handle. I start laughing, but manage to hold my foot still. You applaud my efforts, but this time don’t stop. In fact you now have all four fingers slowing dragging their way around my foot and I no longer can handle it and try to move my foot away. This must have been the moment you were waiting for because once I moved my foot you went nuts and attacked with everything you had. Both hands tickling the top and bottom of my feet. Then to be even crueler you held my toes back and attacked under and between my poor toes. This was by far the worst tickling of the day. I was in no condition to beg for you to stop, I probably would have said my safeword if I was able to get anything out, but I once again had fallen into silent laughter.

You stop and make sure I’m ok, once I’ve caught my breath I say I am and you repeat the process with my left foot. Seeing I have taken about all I can handle for the day you tell me that how well I handled my first session and begin to untie me. As I lay there collecting some strength, you tell me that next time you’ll start with my feet so you can really go to town on them. You tell me stories of how you’ll tie my toes back so I can’t struggle as much and that next time you’ll bring some fun tickle tools to play with like brushes and pipe cleaners and a few other tricks I’ll just have to wait and see.
It all sounds terrible and exciting at the same time. It was quite the day, more torturous and fun then I ever could have guessed. I thank you for making so enjoyable for me and you promise that the pleasure was all yours. We agree that we’ll have to do it again someday soon.

Until we meet again…
 
Great story. I liked the first person perspective, and I hope your first (real) experience is as much fun as this!
 
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