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Learning about myself with Holly

  • Author Author TickleBoy314
  • Create date Create date
  • Blog entry read time Blog entry read time 9 min read
I was at a wedding right after graduating college back on campus. I knew a lot of the girls at the wedding because many were college athletes there. One, in particular, caught my attention.

Holly transferred in the year after I graduated, so I didn't know her as well. She was a sweet southern belle with full long blonde straight hair and I sat next to her during the wedding.

She had actually put on a lot of weight since I remember her, but her body was like a plus-sized model and with her hair, her lips, the makeup and blue eyes, she really looked better than the other girls who may have been thinner or smaller.

Holly's southern accent and the way she liked to move her tan athletic legs and thighs around her dress was just teasing me. I think she knew I was into her, but she was going to play this one out.

At the reception, it was dry, so we left for a nearby bar. Beth was the mother hen of the group, a sarcastic tall brunette who was married to a professional athlete and she was trying to push me off onto Trisha, who she thought would be a good match for me as she was well into fitness, but didn't have much of a personality and wasn't drinking, so striking up conversation was very tiresome.

I was up at the bar getting another round when I heard Holly's voice, "Hey stranger, going to get me a drink?" I cocked my head over my right shoulder, playing her game and said, "What's in it for me?" She hugged me around my stomach and said, "Pleeeeease, sugar!" That 'sugar' in her voice pretty much sold me and totally took down my guard. So I agreed and got her what she wanted.

As she let go, her nails scratched along my abs and ribs and I shuddered, almost dropping the drinks.

Holly giggled and said, "I guess we know where you're ticklish," and pressed a finger to her lips in a sly smile, gently licking the edge of her nail as she turned away.

As the night went on, I kept getting closer to her, rubbing my hand on her smooth baby blue dress which complimented her perfectly. She reciprocated later on my knee and that's when she found ticklish spot No. 2.

At this point, when she recognized it, she whispered in the ear to a friend of her's who looked right at me and giggled and said, "Wouldn't that be something?!"

I had no idea, but I figured they were talking about me. The bar closed and we started to leave. Her friend said, "After party at our place!"

Holly said, "Let's go!" And grabbed my hand and pulled me after her toward her car. She had had a lot, so I told her I'd drive. Plus, at the thought of possible road head, I couldn't resist the chance.

She agreed, but said, "Let's stop back at my place to get some more alcohol. No one will be there tonight!"

I didn't get any oral pleasure on the way and I wasn't sure what no one being home had to do with getting alcohol, but I went. Once we got inside her house, she turned to kiss me, but pulled away and said, "I have a better idea!"

I was following her to another room where she pushed me up against the bed, came in close for a kiss, then right as my lips came close, she pushed me back on my back onto the bed and said, "Nooooottttt yeeeeet..." in a drawn out accent, shaking her head "no" and her finger at me.

The anticipation was building up. I was already hard, and she pulled off my shoes, then my socks and unbuttoned my jeans to pull them off. I didn't wait and tore off my shirt and tie.

She giggled and said, "Want to play naughty?" I was up for anything after the tease I had just been put through, so she grabbed my tie and said, "Up here!" and patted the pillows at the top of the bed. I quickly complied and scooted up. I had only been tied up once before and other than the hand-cuff experience in the sorority house, this seemed a lot more secure.

She started to tie my hands together behind the brass head rest and pulled the tie very tight. She asked, "Does that hurt?"

It kind of did, but I wasn't going to complain.

She said, "Wait right here, sugar. I'll be right back." Then she kissed her index finger and placed it on my lips.

She left the room and came back naked, except for her white shiny bikini panties and a sheer white bra.

Despite the fact that I said she was more on the side of a plus-sized model, she had me sold on them from then on. Her thighs were big, but athletic, her body shrunk from her torso and had a a little belly fat which was perfectly cute on her body.

She slowly crawed onto the bed and reached down and put a fingernail on the sole of my right foot and drug it up enough to get a squeal from me. From there, her finger nail made a back-and-forth squiggle line up the inside of my leg finding small ticklish areas until she got up to my boxers and she ran it inside only to find my inner thigh got me to kick my leg loose with a a deep breath from the tickle.

"Oh, that just will not do!" she said, and slid my boxers off, leaving a fully erect penis flapping in the wind.

She ran her finger up my stomach and scratched my abs and then the side of them only to get a ticklish reaction and a shaking from me.

"Wait," she said with a cocked smile. "Here", and she scratch the ribs where I belly laughed again. "...or here!" and her eyes beamed open as she reached inside my inner thigh with her left hand and I turned my whole body as my penis obstructed her fingers.

I thought it would intrigue her, but she got up from the bed said, "No, no, no," quickly and swift and went to a set of drawers.

I was so disappointed, but at the same time was glad she had stopped tickling me. I thought she was going for a condom. Maybe hoping...not quite.

What happened next changed me forever, at least when it comes to attire when I'm tickled.

"They're in here somewhere," she said. She pulled out something and swung it on her index finger.

"I will not have THAT getting in the way." It looked like she pulled out a pair of her panties, but it was a bikini-made brief for a guy and she said, "One foot at a time," and slid it up my legs until she snapped it on over my bulging penis which was now covered.

This was getting awfully strange, but I was now wear a pair of men's undies, I thought, that girls wore.

"There!" she said, and scratched my belly button with a finger nail, sliding it down to my new undies (I'm pretty suire they were some other guy's who slept with Holly before) and running her finger nail inside the waistband.

That's when I made the mistake of saying, "Please!" I don't know why or how that slipped out, but it was a mistake.

"Please? Please what?" she said, licking the inside of the top of her lips.

"I guess you want some more if you were polite enough to say "Please."

Holly sqautted her butt onto my thighs and squeezed her thighs and legs around mine as I could feel her silky satin panties rub onto me. She didn't grind, only constricted her legs which were VERY, VERY strong!

Her smile was gone, her stare was back and beaming and then said the three words that made my eyes bulge and me shreik out in terror...

"It's tickle time!"

She wiggled her finger nails and dug into my abs, I started to laugh uncontrollably and my back arched and my butt sprung into the air off the bed as if someone electricuted me with the paddles. But my lower body was paralyzed from her constriction of her athletically toned thighs.

This made her mouth form a close-mouthed smile as her fingernails worked up from my abs to my ribs and then up to my armpits where I really started to shake. I thought I could shake loose from the tie, but she must have practiced tieing people up before. I wasn't getting loose.

The whole bed shook, but she kept tickling and poking me. I tried to turn my body up between her thighs and started to get on my side when she said, "Oh no you don't!" and slid up where her butt was on my stomach and that's when the body shifting was over.

I was trapped.

She had full reign over my ribcage, arm pits, neckline and used her finger nail to lightly rub my the top of my upper lip, which was so irritating and ticklish that was forced to close my mouth between tickles and now I was starting to really lose my breath.

Holly saw this and shifted her body a 180 and now I was staring at the back of her panties resting on my chest and her maginificently big strong thighs jetting from her butt and squeezing my ribs, which was getting squeezed very tightly making it harder to breath. That's when she started tickling my inner thighs. My legs were shaking everywhere, but she had total control, working back and forth from the inner thighs to the back of the knees. My legs kept shaking, while my erection was full and I was losing breath.

I wasn't sure how much longer I could go, or she would try, and that's when she scooted her body up on my thighs and started going after my feet. I was done, wheezing and laughing. Begging her to stop. Bargaining, pleading, doing whatever. She would look over her shoulder every so often and shake her head "no", like I was asking for something ridiculous.

Holly finally waited until I was totally out of breath and got off for a second, while I rested.

"Oh, you're not done, sugar." She came back from her closet with a scarf and then tried to tie my feet to the bed rest. I tried to move them away, knowing I'd be done if I did, and she said, "If you try that again, I'll tickle you all night!"

Stupidly, I aggreed and she tied them together which was the dumbest move I made all night.

Holly then smiled, then lifted a finger nail from her palm facing the ceiling and tickled my right foot, then my left as I howled.

She kept doing it and doing it. My body bounced up and down on the bed like I was carrying an electric pulse. I'll never forget the way she looked and the different expressions she gave me while she tortured me through laughter.

Holly grew tired and I had nearly passed out, when she said, "You'll miss me" as she moved her face near mine for what I thought was going to be a kiss. Second stupid mistake coming up... I said, "Yes."

"Don't worry," she said. "I won't leave you alone without your tickles tonight."

I saw her leave the door as her sexy thighs swung out the doorway. She came back with a bottle in one hand and what sounded like a key chain rattling. Then, she took what was in the bottle and started rubbing it on my bound feet. That's when I noticed the key chain was what looked like a small golden retriver.

"Don't worry, sugar. Scarlett will keep you happy tonight," then laughed and left, closing the door behind her. That's when I saw the dog's head beyond the bed rest and then felt a cool tickling on my feet. I think it was worse than Holly's fingernails. I started laughing and don't remember stopping because at some point I either fell asleep or passed out.

I woke up to bright sunshine in my eyes in the bed, untied, the dog was nowhere to be found, and I was completely naked with my pants thrown on top of me. The undies were removed. I felt extremely lighter than the night before and had.

My shirt was gone and I found my socks and shoes.

Holly was nowhere to be found. I looked around the house. Saw another couple bedrooms where I guess she slept and then went out to my car and left. I had to be someone that afternoon.

I left that morning without every feeling a kiss, did not have sex or have as much as a blow job or hand job. She tied me up, put other underwear on me (the took them off...to this day when I'm tickled, I always have a pair so my tickler has a clear shot at my inner thighs), tickled me... let her dog tickle me, stole my shirt and left me without a clue in the morning.

It was one of the best nights of my life looking back, but as with all the rest, one of most terrifying, which made it that much more special.
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Author
TickleBoy314
Read time
9 min read
Views
48
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