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My First Tickling Session at 23 (F/M, erotic)

Anyone/M Lee

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Joined
Feb 17, 2013
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5
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Hey guys. I wanted to share my memories of my first tickle session ever. I had my first tickle session when I was 23 years old, and to this day, it remains one of the most memorable sessions I’ve ever experienced. [Jump to the asterisks for the juicy details, and be warned, there is some NSFW stuff towards the end.]

For context, I was living alone in a big city and had just gone through a tough breakup. Even though it was amicable - she’d gotten a job in London we both agreed was too good to pass up - it still hurt and left me reeling for a month. After weeks of Adele on repeat and sobbing into takeout containers, I pulled myself together and realized I needed a good laugh to shake me out of my blues. So I did something I’d always dreamed of doing but never had the courage (or the singleness) to do before - I scheduled a session with a dominatrix.

I’m sure many of you have looked for a domme before, but at the time I was a complete novice at it, so I was really going in blind for what I was looking for. I knew I wanted someone independent, totally legal, affordable but well-reviewed, organic/grassfed/free-range/all that jazz. Finally, I found a woman named Nancy who advertised massage and fetish services. She seemed nice, friendly, and most importantly, utterly unlike my ex. Instead of a petite, slender Asian in her early 20s, Nancy was a buxom full-framed 40-year-old with flaming red hair and killer nails. I sent her an email, got a reply, and scheduled an appointment for that Thursday. Rubicon crossed.

My heart pounded in my chest as I stepped up to Nancy’s door, palms and soles sweaty, toes curling in the black dress socks I had worn just for the occasion. Not because I was worried about being tickled to my limits (well, not ONLY that), but because I was standing in front of an office building. Not a house, not an apartment, an honest-to-goodness WeWork-esque space with listings for startups, design firms, and the occasional candle factory. I buzzed her number worrying I had got the wrong address, but after a flicker of light from the panel and a click-whir from the door, I was in. I kept running my hands through my long brown hair in the elevator, adjusting my glasses and tugging at the sleeves of my button-up, I guess worried I wouldn’t be a good enough ticklee or something? I needn’t have feared.

I left the elevator and nervously walked down the fluorescent-lit hall until I came to a half-open door with soft amber light emanating from the room within. I gave a cautious knock and Nancy opened the door smiling. “Are you Lee?”

I nodded, stuttering in the affirmative as I looked her up and down. She was probably a few years older and a few pounds heavier than her profile picture, but still an attractive, sexy older woman. Her red hair hung in curls around her sharp features, and freckles spotted her shoulders and breasts, barely contained by the lavender teddy she had on under a black lace dressing gown. She quickly ushered me before any tech bros could walk by.

The door clicked shut, and I tried to take in the room as my eyes adjusted to the dim light. The room was small, but covered wall-to-wall with carpets, pillows, beaded wall hangings, and a sturdy massage table in the center of the room. A TV and CD player sat in the corner on a table, and I couldn’t help but notice that a variety of feathers and brushes lay next to them.

“Have a seat, honey,” Nancy whispered as she led me to the edge of the massage table. As I sat, she smiled and began playing with my shirt collar. “Can I help you get comfortable? What would you like?” She clearly knew she was dealing with an amateur.

I mumbled something about leaving my boxers and shirt on, but taking the rest off would be fine. She proceeded to strip me down, unbuckling my pants, unbuttoning my shirt, leaving my torso exposed, pulling off my size 14 shoes one at a time and peeling off my dress socks, exposing the warm pink soles. Gently pushing me onto the massage table face-up, she tugged my jeans until they slid off, leaving my lower body clad in nothing but a pair of black silk boxers.

“Oh, do you mind if I put on some music?” she asked.

“Not at all, whatever you want,” I stammered, thinking she would put on some R&B or soothing New Age music.

No, instead she goes to her DVD player and, I shit you not, puts in a copy of the 1973 movie adaption of Andrew Lloyd Weber’s Jesus Christ Superstar. So this is now the soundtrack of my session.

* * *

Returning to the massage table, Nancy is ready to begin. Even though I’m unbound, I feel utterly trapped in the best way possible. She stands over my head, her pendulous breasts directly in my line of sight, and proceeds to gently tickle my torso with the soft tips of her fingernails. Even this light touch tickled, though, and I struggled to hold in my laughter as she grazed my chest, my collarbone, my neck, and behind my ears. Already, my stomach was clenching and flexing, struggling to keep in the giggles that are building inside me.

She opened my shirt more and began to explore my upper body more. Her nails traced over my ribs, drifted over my flexing belly, and skittering on top of the sensitive skin of my love handles, a super-ticklish spot that caused me to let out a short cackle and clamp my arms down to my sides.

“Ooh, I’ll have to remember that for later,” she laughed.

She started circling me, clearly having fun with such a sensitive novice. She dragged her nails in her wake, down my sides, along my hips, and down my thighs. Here she gave a few exploratory tickles on the outside of my thighs, which elicited little reaction, and the inside of my thighs, which elicited a much bigger reaction in more ways than one. I cackled again and squeezed my legs together as she continued her exploration. She finally landed at my feet, and I knew from the moment her nails touched my ankles that this would be a hot spot for her. Her fingers danced over the pale tops of my feet, then over the toes to softly caress my trembling soles. Unable to remain both still and silent, I finally let out a stream of embarrassingly unmanly giggles while struggling to keep my quivering feet in place.

“Aw, looks like I found a little treasure trove!” she exclaimed teasingly. She pressed down on my ankles with one hand - not enough to make me immobile, but enough to know she meant business - and started walking her fingers up and down my soles like she was flipping through the yellow pages. My laughter became louder and louder now, and I periodically tried to cover my mouth lest a passing marketing executive knock on the door and ask what the racket was. Nancy’s fingers were homing missiles for my feet, finding every ticklish nerve ending and taunting and teasing them until I could barely stand it.

The rest of the session was a bit of a blur, notable for moments more than any specific arc, so I’ll call out a few highlights.

At one point, Nancy straddled my stomach and leaned in to tickle my upper body, her breasts pressed against my chest, her red locks tickling my face. I remember squirming and writhing under her, especially as she snuck her fingers under my arms and scritched and scratched the soft sensitive skin of my pits. Though she was on my stomach, when she leaned back she would grind against me and I could feel myself becoming incredibly excited.

Later on, we moved to the carpet where she had me sit against the wall with my feet out. She wrapped her legs around me in an ankle lock, immobilizing my feet and giving me an incredible view of her plump bare tootsies. She raked her nails up and down my soles and under my toes while I guffawed with abandon, though I tried to keep her feet in view even through my laughter.

Towards the end of the session, Nancy has an idea to tickle my upper body again. At this point, I’ve removed my shirt, now dressed only in a pair of boxer shorts that are growing tighter by the minute thanks to my erection. She laid me down on the rug and had me stretch my arms high up overhead. She then proceeded to sit on my elbows and inch her way up until my head was resting in her lap. She stretches her legs out so her feet are in full view, beautiful toes with crimson polish resting on my hips.

In this state, I was absolutely immobile. I could not budge my arms an inch. Nancy began swirling her devilish nails through my armpit hair, and for the briefest of moments, I tried to hold in my laughter before succumbing to a bout of frantic titters that hit a register few people other than professional opera singers can hit. Something about my captive arms, her fingers teasing my sensitive skin, the sensation of her feet resting on my body, and the feel of my silk boxers rubbing against my erection, were driving me absolutely wild. So wild, in fact, that after just a few minutes of this, I realized that I was going to cum. I tried to fight it, to keep still, to stop the rubbing and brushing, but nothing could stop the dam from bursting.

I let out a loud gasp and felt my cock spurt and pump, the sweet release from an hour’s worth of teasing and tension. But then I realized something - Nancy had no idea what had just happened. She continued her tickling, which had flipped from tantalizing to downright torturous in a matter of seconds. Her teasing fingers suddenly felt like ticklish jackhammers on my skin, and the friction of my boxers felt like the world’s most ticklish belt sander. The sensations were so intense my eyes started to blur and I was incapable of blurting out my safe word for a full 30 seconds (though it may have been 30 hours for how long it felt.)

Nancy finally realized that I enjoyed our session much more than she realized and stopped tickling me. She giggled and passed me a box of tissues, which I blushingly accepted. We made small talk as I quickly get dressed, and as I handed her the money, she planted a kiss on my cheek and scribbled her nails across my belly one last time.

I walked down the hallway sweaty, bedraggled, shirt untucked, my skin fizzing with excitement…and a smile plastered on my face.

Oh, and for some reason, “I Don’t Know How to Love Him” stuck in my head.
 
Wonderful story! 😀
I wish that I had had your courage at age 23.
 
I love stories where the lee orgasm's without anyone knowing and continues to get tickled! Guy or girl lee doesnt matter, wish there were more. Recommend others if you know any!
 
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