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Tickling my crush while massaging her

Iggy

1st Level Red Feather
Joined
May 11, 2001
Messages
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Hello everyone.
I've written a few stories here and there. I did a fiction one a little while back on a KTLA reporter, and I've done a few true stories in the past. For whatever reason, I decided to do one more for the heck of it.
I was in my 20s at the time, and I had a crush on this girl--let's call her Gillian. She was one of those platonic friends that one hangs out with a lot that turns into a crush (you know how it goes). I knew Gillian was ticklish since her friends had tickled her, and I was able to get in a poke here and there. I never got to give her a good tickle, but I always had the mix of hope and fear since I didn't want to mess up my chances with her (you know how that goes too).

One day in the summer we were alone at my place. We had done some kind of activity, and we were chilling out afterwards. In the past I'd given her massages, and I was pretty decent at it. She jumped at the opportunity. In a previous time, she allowed me to unhook her bra and have access to her whole back, so I asked her if she wanted that again. This time she said no. So it was just through her t-shirt this time. I massaged her shoulders and up and down her spine while I straddled her thighs, and she relaxed immediately. It was then that the thought of tickling her thoroughly occurred. Now if I didn't have a crush on her, I likely would have done a thorough tickling on her already like I did to my friend Marie (which is another short story maybe in the future), but because of the crush I had always been hesitant. This time, while I don't know why I did it, I decided to take advantage.

The whole time I was having a small talk with her as I massaged her. In the conversation, I was hoping for an excuse to tickle her. I don't remember exactly she said, but it was something sassy from her--perfect. "I can't let you get away with that." I could see her smile since her head was to the side. "What do you---aaaaaaah!!" At that point, I dug my fingers into her ribs. Instantly, she clamped her arms to her side trying to squeeze my fingers in a vain attempt to stop the tickling. Now, those of you who know me know that my favourite target is the female armpit, but there was no way I could get to hers. So I continued to tickle her ribs. She rocked her upper body back and forth in another vain attempt to stop the tickling, but all that did was to push my fingers into her ribs more. While I like it when the women I tickle try to say something while the ticklish laughter impedes their attempts, there was nothing like that here. All she did was laugh. It was a musical laughter that I just thoroughly enjoyed. I noticed that when I slid my fingers to her waist, her laughter took on a different cadence almost like in a different musical key. Her struggles started to decrease, and she couldn't squeeze her arms as much. At this point, I considered getting her armpits, so I moved my fingers toward her upper ribs near her breasts. At this point, her laughter shot up in volume to the point of a near scream. At the time, I'd never experienced that. It was mostly laughter but the scream was there (think the tickle scene with Anne Hathaway in Love and Other Drugs). I loved it, but I also noticed her face was getting red. At this point, I figured I should stop, so I did.
She had the residual giggles as I rubbed her back while she just continued to lay face down. When she got the energy to sit up straight, she punched me in the arm. "You jerk!" She wasn't mad, but she was pretty tired, so I didn't do a follow up tickle. In fact, I refrained from tickling her for a while.

A year later (after I had tickled her a few times in small ways), I asked her which was the worst time. "It was that time at your house when you massaged me. That was the worst. I couldn't move, and toward the end, I started to panic." I figured that was the time that I tickled next to her breasts with her face turning red, so I was glad I stopped when I did.

I never was able to turn that crush into a relationship, though she did give me a nice kiss once. We still keep in touch, but we've built our own lives in different parts of the country. It was a fun tickle, I must admit.

I hope you all liked the story.
 
Great story! :tickle: Thanks for sharing your experience here. 😀
 
We had done some kind of activity, and we were chilling out afterwards. In the past I'd given her massages, and I was pretty decent at it. She jumped at the opportunity. In a previous time, she allowed me to unhook her bra and have access to her whole back, so I asked her if she wanted that again.
For the record, I'm quite certain she was into you especially with the kiss part you mentioned at the end. But maybe you tried it and it didn't work out for other reasons.

Great story, of course 😉
 
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