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Breaking My Tickling Cherry...How It Started for Me

TickleBoy314

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Oct 4, 2010
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Everyone has a story of how it began and why they came to like tickling. Some see it as a sadistic means of torture, some see it as playful touching where you can't really get hurt. I mean, you are laughing after all, right?

My story dates back to college when I was dating Katie. Katie was pretty much my favorite girl and the first one I really enjoyed exploring myself with. However, Katie had a jealous roommate in her sorority, Alex. Alex was quite pretty and I never understood why she didn't have a boyfriend. Instead, she seemed to like to get all the boyfriends in trouble of her friends. I happened to be the unlucky one dating her roommate.

One night Katie was gone to an intramural practice and Alex told me to come over for a social hour, that Katie wanted me to be there when I came back. I has suspicions of Alex, but decided to anyway.

It wasn't much of a social, but girls were breaking the on-campus (never enforced) rule of drinking in the sorority houses. Alex wanted to have a serious talk with me and told me to come up to her room. I didn't want to, because how awkward would it be if Katie came back and Alex and I were in their bedroom. Plus, as I said, Alex had a reputation.

I had quite a few drinks for what had to be 2-3 hours and lost track of time. Alex started talking about other guys I knew and asked if they liked her. Since most of my friends would love to date a girl like Alex, let alone do everything else with her, I said, "Yeah, all my friends want you, Alex. Look at you!"

Alex was about 5'5 with long dirty blonde hair, a cute smile and a somewhat athletic build with a bit of the freshman turning to sophomore 15, but after seeing all the girls in the sorority house at the pool, Alex definitely had a great bikini body.

Alex pressed on and said, "Do YOU want me though?" and had this sad, "If you say 'no' to me voice, I'll cry" look on her face.

I hadn't see her like this and to be honest, the alcohol was having a strange effect on me that night.

I said, "Where's Katie?" and went for the door. Alex started to cry and started saying that she was 'fat' and 'unattractive', two words no guy would ever use, but she was playing the part well, whatever it was. I felt bad and went to sit next to her. I kept drinking and told her that I thought she wasn't fat nor unattractive and then leaked that I had seen her in a bikini and she looked fabulous...better than most.

How quickly her mood changed. She smiled, which was more evil than happy and said, "Really? Because I just got a new bikini for Spring Break. Let me try it on for you and tell me what you think. Just lie over there on the bed." She didn't bother to go in the closet. Off came the denim mini-skirt, and her t-shirt and before you knew it, she was stadning there in her bra and string bikini panties. She saw I was a bit embarrassed and said, "It's not like you haven't seen me like this before. Just like at the pool." So she turned so as not to show me her breasts and put on the top, then shimmied off her panties and put on the bottom. Turned around and said, "What do you think?!" I thought she looked great, but also totally forgot that Katie could come back at any second.

I told her she looked sexy and her legs were stunning. You could tell her confidence was growing, but I didn't notice because I was getting drunk and feeling the effects. She sat by me and said, "You don't look good. Are you drunk?" I said, I wasn't and then she tried to kiss me. I was going to pull away, but she felt good and smelled good with her perfume so I had to have a taste, even though I knew I shouldn't.

She said, "You look tired, just sleep over there in Katie's bed and when she comes back, it'll be a nice surprise for her."

So I did. BIG MISTAKE!

When I awoke from being passed out, I could barely feel my hands and I went to wipe open my eyes, but my hands wouldn't come down. They were being restricted by something. I tried to adjust my eyes and then realized I was handcuffed to the top of a bed and my feet were tied by something to the bed or something. My clothes were off. I thought I must have taken them off, but why would I be stripped down to my underwear.

Then I heard Alex's voice, "Katie knows what you did and she's upset. She's downstairs crying and doesn't want to see you. I can't believe you tried to cheat on her with me!! All you men are scum, but this is going to be the last time you do it in this house!"

I tried to argue, but that's when I felt the tickling sensation under my nose. When you can't brush it away with your hand, it's very irritating, not to mention annoying. It wasn't Alex, but one of Katie and Alex's friends, Chelsea. A miniature version of a girl, maybe about five feet tall on a sunny day and she was using a feather to tickle under my nose and smiling at me.

Then Alex and another girl, Dana, who was on the soccer team, got on top of me facing away from each other. Alex still had on her bikini, which I was probably wondering how she explained that to Katie, but I found out later she said that's when I 'tried to cheat on her'.

"It's time you learned your lesson," Alex growled as she grinded her thighs into mine. Before I could say anything, I felt Dana tickling my feet. I don't usually admit this, but I am extremely ticklish and I couldn't imagine how these girls thought tickling was a punishment that would be suitable for a guy.

I started laughing uncontrollably from Dana's tickling. Fortunately, she didn't have fingernails, but it didn't matter. Alex, on the other hand, always had fake nails in a French cut and started into my ribs. Chelsea went right after my arm pits.

I was laughing so hard, I didn't realize how bad I was thrashing and my wrists being bound by metal were hurting. I was getting hard and Alex realized this and scolded me, "You boys don't quit, do you! I feel you getting hard." And she reached her hand back and slapped my cock through my undies as hard as she could.

I begged, "Please stop! I won't ever do it again!"

I wasn't sure what I wouldn't do again, but it sounded right.

I figured begging would make it stop. All the thrashing over just 30 seconds to a minute not only had me tired, but I felt like I could pass out.

Alex wouldn't have it and yelled, "Beg some more, ass hole! That's my best friend you tried to cheat on me with!"

I had to admit, I was really turned on by the fact that Alex chose to stay in her bikini to tickle me. Dana and Chelsea weren't wearing much either, but I remember them laughing the entire time, smiling at me and saying, "Isn't this fun! I know you're having fun because you're laughing, so we'll keep doing it!"

Their pleasure from my pain was keeping my erection and I was just begging and begging for them to stop.

Alex turned her mean look to an evil smile and kept at it. Then she told Chelsea to go into her bathroom suite and get her toothbrush. I had about five seconds to breath before Alex started into my armpits, but this time she was laughing loudly up in the air, smiling and laughing at me as I begged and said, "It's not even close to being over!"

Chelsea came back with an electric toothbrush and that's when Alex told her to start on my feet and Dana to switch to my inner thighs and belly button.

It didn't strike me then, but it does now; Alex totally had tickled people before and knew how and all the areas. She got so much pleasure out of torturing someone and making them under her total control.

I couldn't take it anymore. It had to only be three minutes, but it felt like and eternity. She kept going and going, while I kept thrashing and begging.

Minutes went by, they switched positions, but fast, so that I could barely catch my breath and started again.

Alex was the most skilled at it, but the cute touches of Chelsea and Dana and their inexperience and cute touches with their smiles made Alex the enemy I was fighting, while they were doing playful stuff that drove me over the edge.

I must have begged for a good 10-15 minutes during their entire exchange. It was the only way I could breath. I know I passed out at some point or fell asleep. But I woke up outside their house on their front swing in nothing but my undies. My clothes were soaked right by me and I had to make it back to my dorm by myself late at night.

I ran into Katie later, but she would have none of it. In fact, their entire sorority pretty much excommunicated me, but there were several others on campus, so I wasn't totally left banished from the social life.

I did run into Dana a couple years later at Homecoming. She laughed about the experience, told me that the handcuffs I was wearing actually had a level that I could have pushed and escaped to maybe fight back, but I didn't know.

She also said that Alex hated everyone's boyfriends and tried to seduce several, including having sex, but I was the only one who ever passed out, so she made the most of it. Both her and Chelsea were drunk and thought the idea was great, so they participated.

Although Dana offered that she loved the fact that her being such a small girl (even though she was athletic and toned), could overpower and turn a 'big strong guy' into a blubbering, helpless toy just by tickling was a total turn on and she'd love to do it again.

As for me, from that point on, I was a bit embarrassed, but at the same time, every time I was tickled again by a girl, I totally went closed up and tried to avoid it at all costs. One girl even caught a backhand by accident, but later admitted she deserved it. I told her if she wanted to make it even, I'd let her tie me up and tickle me. She thought it was strange at the time and declinde, but later approached me about it and I was her fingers' toy for a nice session of fun.

That's how it all started and since then I have had a few experiences, but it's all been worth it.

It's one of those things that's a love/hate, but really the hate makes you love it oh, so much more even during those times you're begging pleading and don't want to... (as I was told once by a woman 'ler'), "It's for your own good."
 
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