I haven’t written about tickling experiences in the past but here we go:
To start off I’m going to give a little backstory. So Madi (name changed obviously) works with my dad but being my age we hit it off pretty ok where I tease her and she teases me and this has been going on for maybe 2 years? She’s a short latina with tattoos and a beautiful laugh like Layla from the tickle room if you know who I’m talking about. Well I started playing imessage games and through that we decided that the 20 questions game will have a catch, where if you cannot guess the word in 20 questions you have a punishment. Now this started as you cannot be disrespectful to me in anyway for 2 days or you have to agree to whatever I say etc. But I knew what I was hoping for and found a list online of punishments that included what I wanted. So a few days after she lost she asked if I ever came up with a punishment for her to which I replied no and looked up some and told her pick between 1-7 (3 of the items on the list were not feasible) to which she picked number 5 the one I wanted her to pick: Get tickled on your feet for 5 minutes. I did not know if she was ticklish but upon revealing her punishment I got all the confirmation I could ask for with the “LITERALLY THE WORST ONE” and “YOU'RE TRYING TO KILL ME.” After a but of teasing we agreed to 2 minutes of foot tickling 1 minute prior to the hangout and 1 minute after.
Cut to when we finally hung out tonight. We went to a bar that has arcade games in the back that we both agreed would be fun. When we parked I brought it up along the lines of “don’t we have something to do first” to which she said she’d rather take it in bulk at the end. So we had fun at the bar and hopped from game to game when we found one we were equally good at and it was 2 all next point wins so I said hold on pause. “How about we place a wager on this point” since she was hyping herself up so much I thought it’d be a good idea to which she replied “idk how to punish you I don't know how to get you,” kind of paused as I replied it wasn't my fault she wasn't creative to which she gave me a side eye and a smirk I will not forget and asked “ wait are you ticklish?” I told her yes which in all fairness I am but I can hold it in if I want to unless it’s like my neck. So we agreed loser of this match gets tickled for 1 minute and if Madi loses it would turn her 2 minutes to 3. So we counted down and started the game and sure enough I won. So I paid off our tab while she went to the bathroom and then we walked to my car. My car has 3 rows of seats so I had her sit in the very back while I sat in the middle in order to make it easy to tickle while pedestrians cannot see what's going on.
I asked to test it out first and meanwhile she is trying to hype herself up saying things like “you won’t get a reaction,” “I’m not even ticklish anymore,” etc. As soon as I tickled her foot she covered her mouth and retracted her foot. So I instructed her to put her foot between the headrest and the seat. She had both feet in but as soon as I started tickling her feet were gone. Now her feet are beautiful. White painted toes, low arch unfortunately but she said she prettied her feet up for this. I set the timer for 1 minute and it was brutal for her I had to hold her feet but once I started tickling her toes and her arches she was giggling and snorting while also saying I’m evil and I hate her which was really fun to hear. She had 20 seconds left of the first minute where I said if she can keep her feet in the headrests (one foot in each) for the last 20 seconds I’ll forfeit that last minute and she can tickle me. She said no and said she’d rather me hold her feet and tickle and she’ll do that for the second minute. So I went all out for the last 20 seconds holding her toes back and tickling the area under till the timer ran out. Now its time for round 2 and the headrests hurt her feet but Madi agreed to keep her feet there and just not move them. Round 2 starts and she lasts 31 seconds which I was impressed. I finished the round which led me to be on the receiving end. I leaned back in the chair while she sat behind me and when I started the timer she tickled my sides for 30 seconds to which I stopped the timer and suggested a final wager. If I could not make a sound the last 30 seconds she tickled me I could tickle her again in order to find where her worst spot is. She agreed and I gave it my all to stay silent. After yet another victory she proclaimed I cheated but told me her worst spot is her sides and swapped seats with me. Now Ive been sneaking tickles in the whole time in the car, if her foot didnt move after the timer went off I kept tickling and while she was anticipating the timer to start I was testing different spots but I asked her if she was ticklish there first and she let me try since I did not want to overstep boundaries. I tickled her for 10 seconds before she couldnt take it so I paused the timer again, and she was able to last another 10 seconds before she stopped. I gave her the option if she wanted she could get tickled for the last 10 seconds anywhere she wanted to which she handed me her feet again which I was not complaining about. After the tickling was finished we discussed the future of the game and she even said that after I said there’s a chance the punishments from here on out will always be tickling related, since she said she will never lose again, added that every now and then she will let me win because she “feels bad” but knowing a loss means tickling her suggesting she’d throw some matches I could be reading too much but it seems like she might have liked it. She also said I’m the only one she let tickle her for this long. I already have another tickling game planned with her choosing to get tickled in a movie theater so hopefully that is as fun as this was.
To start off I’m going to give a little backstory. So Madi (name changed obviously) works with my dad but being my age we hit it off pretty ok where I tease her and she teases me and this has been going on for maybe 2 years? She’s a short latina with tattoos and a beautiful laugh like Layla from the tickle room if you know who I’m talking about. Well I started playing imessage games and through that we decided that the 20 questions game will have a catch, where if you cannot guess the word in 20 questions you have a punishment. Now this started as you cannot be disrespectful to me in anyway for 2 days or you have to agree to whatever I say etc. But I knew what I was hoping for and found a list online of punishments that included what I wanted. So a few days after she lost she asked if I ever came up with a punishment for her to which I replied no and looked up some and told her pick between 1-7 (3 of the items on the list were not feasible) to which she picked number 5 the one I wanted her to pick: Get tickled on your feet for 5 minutes. I did not know if she was ticklish but upon revealing her punishment I got all the confirmation I could ask for with the “LITERALLY THE WORST ONE” and “YOU'RE TRYING TO KILL ME.” After a but of teasing we agreed to 2 minutes of foot tickling 1 minute prior to the hangout and 1 minute after.
Cut to when we finally hung out tonight. We went to a bar that has arcade games in the back that we both agreed would be fun. When we parked I brought it up along the lines of “don’t we have something to do first” to which she said she’d rather take it in bulk at the end. So we had fun at the bar and hopped from game to game when we found one we were equally good at and it was 2 all next point wins so I said hold on pause. “How about we place a wager on this point” since she was hyping herself up so much I thought it’d be a good idea to which she replied “idk how to punish you I don't know how to get you,” kind of paused as I replied it wasn't my fault she wasn't creative to which she gave me a side eye and a smirk I will not forget and asked “ wait are you ticklish?” I told her yes which in all fairness I am but I can hold it in if I want to unless it’s like my neck. So we agreed loser of this match gets tickled for 1 minute and if Madi loses it would turn her 2 minutes to 3. So we counted down and started the game and sure enough I won. So I paid off our tab while she went to the bathroom and then we walked to my car. My car has 3 rows of seats so I had her sit in the very back while I sat in the middle in order to make it easy to tickle while pedestrians cannot see what's going on.
I asked to test it out first and meanwhile she is trying to hype herself up saying things like “you won’t get a reaction,” “I’m not even ticklish anymore,” etc. As soon as I tickled her foot she covered her mouth and retracted her foot. So I instructed her to put her foot between the headrest and the seat. She had both feet in but as soon as I started tickling her feet were gone. Now her feet are beautiful. White painted toes, low arch unfortunately but she said she prettied her feet up for this. I set the timer for 1 minute and it was brutal for her I had to hold her feet but once I started tickling her toes and her arches she was giggling and snorting while also saying I’m evil and I hate her which was really fun to hear. She had 20 seconds left of the first minute where I said if she can keep her feet in the headrests (one foot in each) for the last 20 seconds I’ll forfeit that last minute and she can tickle me. She said no and said she’d rather me hold her feet and tickle and she’ll do that for the second minute. So I went all out for the last 20 seconds holding her toes back and tickling the area under till the timer ran out. Now its time for round 2 and the headrests hurt her feet but Madi agreed to keep her feet there and just not move them. Round 2 starts and she lasts 31 seconds which I was impressed. I finished the round which led me to be on the receiving end. I leaned back in the chair while she sat behind me and when I started the timer she tickled my sides for 30 seconds to which I stopped the timer and suggested a final wager. If I could not make a sound the last 30 seconds she tickled me I could tickle her again in order to find where her worst spot is. She agreed and I gave it my all to stay silent. After yet another victory she proclaimed I cheated but told me her worst spot is her sides and swapped seats with me. Now Ive been sneaking tickles in the whole time in the car, if her foot didnt move after the timer went off I kept tickling and while she was anticipating the timer to start I was testing different spots but I asked her if she was ticklish there first and she let me try since I did not want to overstep boundaries. I tickled her for 10 seconds before she couldnt take it so I paused the timer again, and she was able to last another 10 seconds before she stopped. I gave her the option if she wanted she could get tickled for the last 10 seconds anywhere she wanted to which she handed me her feet again which I was not complaining about. After the tickling was finished we discussed the future of the game and she even said that after I said there’s a chance the punishments from here on out will always be tickling related, since she said she will never lose again, added that every now and then she will let me win because she “feels bad” but knowing a loss means tickling her suggesting she’d throw some matches I could be reading too much but it seems like she might have liked it. She also said I’m the only one she let tickle her for this long. I already have another tickling game planned with her choosing to get tickled in a movie theater so hopefully that is as fun as this was.
Thanks for sharing your experience here. 
