19 yo. Male Virgin Seeks Older Female for Sexual Mentoring
I hit Enter before I could change my mind, my finger trembling over the keys of my laptop. It was stupid of me to be so embarrassed. It was a Craigslist Ad, not a confession over a bullhorn on the corner of a busy street. No one would reply anyway, and I would be exactly in the same place. I thought college would be different and I would be able to slide out from under the label of ‘Nerd’ wretchedly bestowed upon me in high school, but as I eased into the hustle of academic life, I realized that I might be destined to be alone forever. I had no confidence, no skills, no game. I’d never asked a girl out on a date, never held hands or kissed a girl on the cheek. I felt invisible, but more importantly, I felt completely unprepared.
As a typical Type A personality, I was a planner, a researcher, someone who liked to know about a subject before getting my feet wet. This was a subject I spent countless hours researching. My poor pink cock could attest to that, sore from hours of jerking off to porn in my room, a mountain of used tissues stuffed discretely in the bottom of the garbage can. I didn’t really think that porn was the best way to find out what I wanted to know. The contrived storylines, the fake moaning, the slap of skin on skin as a ridiculously endowed man plowed ferociously into a tiny woman, all too happy to take every inch, it just didn’t fit my expectations of reality.
I wanted to explore the female form, not for my own benefit, but to find out exactly how to touch, lick, suck and pinch. Without someone to practice on, I felt that I would never be any good, and my chances of finding someone were slim. It wasn’t that I wanted to be some kind of playboy, moving through women like a snowplow. I just wanted love. I wanted the kind of love that you feel deep down in your bones, storybook love. I wanted a partner, someone to eat with, and watch tv with and laugh with. I thought a nerd like me wouldn’t find someone without a certain set of skills, and, I was determined to learn somehow. The Craigslist Ad was my final effort. If I didn’t get a response, I was going to give up trying and focus on my studies. I didn’t have much of a plan after that.
A week later, I’d almost forgotten about the ad, busy with classes, papers, and a group project in which I’d taken on most of the work. My email pinged on my phone, and it was a response to my ad. I was nervous to open it, wondering if it would contain some sort of malicious content, someone making fun of me or worse. I didn’t expect the eloquently worded email from a Miss Diana Blackstone saying that she wanted to meet me. The date was set for next Friday evening at a quiet restaurant downtown. She would be sitting at the bar wearing a red coat.
To say I was nervous was a complete understatement. I was sweaty, I could barely focus on my school work and my thoughts spiraled in all different directions about where this was going to go. Was I being catfished? Would she make me into a joke to share with her friends? Would she turn out to be a guy? It took every bit of my will power to drag myself out of the apartment that Friday night and walk the mile or so from campus to the restaurant.
I stepped into the dimly lit bar with candles flickering in glass jars on the table tops, and the din of quiet conversation accompanied by soft piano music. It was not the sort of place I’d run into any classmates, a posh older crowd inhabited the space, elegantly perched on their barstools, cocktails in hand. She was there at the bar, just like she said, a red coat draped over her shoulders, straight dark hair fell halfway down her back. She sat erect, as if an invisible pole was holding her in place, her legs were crossed and I could just barely see the curve of her calf, sheathed in black stockings. Her long red nails drummed on the edge of her wine glass, the pinging sound reached my ears and I froze in place, scared, my breath caught in my chest.
As if she could hear the deafening beat of my heart, she turned towards me, her eyes squinting as she took me in. I was just a scrawny college kid with messy hair wearing khakis and a striped shirt, and I suddenly felt as if my awkwardness was displayed on my forehead for everyone to read, a large sign displaying all my shortcomings. She was elegant and poised and beautiful and I almost turned and ran, but she stood up and walked towards me. Her hand reached out and took mine, soft and warm, and she smiled at me. She was saying something to me, but I couldn’t hear. I shook my head.
“Thomas, it’s nice to meet you! I’m Diana. I have a table waiting for us if you’re hungry?” She gestured to another room and ushered me in that direction, her hand on my arm.
I found my voice as we made our way to the back of the restaurant. “Diana, thank you so much for meeting me.”
I could feel the heat creep up towards my face. I hadn’t thought about the fact that I would have to talk to her about the ad, that I would have to say the words. I want you to teach me how to have sex. I’d imagined this scene over and over in my head, but I’d only focused on the negative possibilities. I never once considered that she would be real and strikingly beautiful and nice.
“I’ve pre-ordered our meal so that we have more privacy to talk. I just picked a few things that we can share and nibble on, I hope that’s okay!” Her voice was sweet, a melodic trill that hit each word like a song, and her eyes sparkled beneath dark lashes in the candlelight.
“Um, yeah, that sounds great. I’m not picky or anything,” I mumbled, hiding my hands in my lap. I suddenly didn’t know what to do with them, as though I were wearing mittens and couldn’t function properly.
“I know you’re nervous, and that’s okay!”
She put her hand on my arm again, and her touch was soothing. I breathed deeply, trying to relax, trying to find myself inside the lump of awkward teenaged male sitting before her. Surely, I had something to offer, intellectually at least!
“I am nervous, I’m sorry,” I blurted, “I want to learn how to have sex! I mean, I want to know how to do it right.”
She smiled at me. Was that pity in her eyes? Or did she look like she was about to devour me. I couldn’t quite tell, but something inside me stirred. I lurched, an involuntary twitch in response to the power she already had over me.
“You want to know how to please a woman?”
I nodded stupidly, swallowing the lump in my throat.
“Just ask her what she likes!” Diana laughed, her pale chin glinted in the dim light as she threw her head back.
I laughed nervously, mirroring her body movements like a puppet. She put her hand on mine and squeezed. I squeezed it back and for the first time that night, the nervous energy buzzing inside of me calmed. I took a deep breath. I can do this.
Part Two here!