I did not have many conquests in high school. I had exactly one long term girlfriend and then right at the end of senior year, I hooked up with another girl who I had been friends with for a while. In college this started to change. Even though I moved about 2 hours away for college, I kept in touch with some people from high school. Eventually, the conversations with one girl (Samantha, or Sam for short) turned a bit more relationship-y and sexual.
Fast forward a couple of weeks and we were informally dating. I had returned to my home town for a weekend and of course we decided to meet up. After hitting the movies and dinner, we went back to her home in town – no drinking or partying, we weren’t 21 yet so alcohol was something that had to be planned, rather than easily acquired.
Sam was very pretty. Her body was curvy, 5’6″, alabaster white soft skin, dark almost black wavy hair, gorgeous blue eyes. She had large, soft, milky breasts. Her hips were wide and her ass matched the rest of her. She wore more makeup than I usually like, but she took great care in it and honestly did a very good job.
Back at her house, things went about as you’d expect from two horny 19 or 20 year olds. We started by making out on the couch in her living room. Hands roaming everywhere, with me running my hands all over her body. She was pulling me into her and running her hands through my hair. My hands drifted to the button and zipper in her jeans and then fumbling under her shirt. As I reach the first of her boobs, she suggest we go to the bed in her room. Deal!
After closing her bedroom door, we resume making out and we waddle over and fall onto her messy, but comfy bed. She takes off her top and bra, revealing her lovely boobs to me for the first time and they fall with a little jiggle, but somehow defy gravity. I straddle her and kiss down her neck, being way too impatient to get to her nipples. I grab her left boob with my right hand. It’s so soft and jiggly, like a water balloon. I take her right nipple in my mouth and start licking, biting, playfully tugging. She is moaning softly and subtly squirming her legs. After focusing on the other nipple for a bit, I continue to kiss down her stomach and then play with her jeans waistband the top of her underwear.
She helpfully lifts her hips off the bed and I slide down her jeans and panties together. She clearly groomed herself ahead of our meetup – she trimmed and shaved in a few places, but still had a fair bit, which I ended up loving. Now, I start to tease her a bit by kissing and biting her inner thigh, then the top of her vagina, then I dive in. Licking her clit up and down, occasionally drifting farther south to lick up any wetness and push my tongue in as deep as it will go. She raises her legs up, initially so her knees are off the bed but then eventually so her legs are in the air with her back arched, giving me great access.
After a few minutes of tonguing, I slip two fingers in her while continuing to focus on her clit. Moving faster and faster as her moans increase. I curled my fingers upward to make sure I was hitting her g-spot. Eventually, my hand was moving back and forth so fast, I couldn’t keep licking, so I kneeled next to her to be able to get more leverage and go faster. She was very wet at this point. Her pussy making a delicious slurping sound as my fingers rubbed inside. Everytime my fingers came out of her, I could see them being coated in her somewhat clear, somewhat milky ooze. Faster and faster my hand and fingers went, her moans turning into low screams until finally she tensed up, said some words I didn’t really understand or care about, and then collapsed. I slowed down my pace, but kept my fingers in, slowly and gently massaging the inside of her. I kissed her, then her neck, then her breasts again while my free hand squeezed and pinched her nipples.
I let her calm down some more and then started to pick up the pace on my fingers again. This time, I slipped a third finger in, so now my index, middle, and ring finger were in her. Faster still, more wetness, more juicy sounds. Never done more than three fingers at this point with any girl, her moans were making me bold. I slipped my pinky in. She had a brief look of surprise on her face when she looked at me, but quickly went back to eyes closed and lip bitten, moaning and breathing heavy. I am not quite sure how it happened, but one of of the thrusts of my hand, her pussy took my whole hand past the knuckles only stopping when my thumb brushed up against the outside of her pussy. Her moans turned into short little screams. She looked at me with a more intense look of surprise and nearly demanded that I keep going. I forget exactly what she said, but it was something like, “oh my god, don’t stop!”. Stop I did not – my whole arm into it now, thrusting in and out of her, stretching her pussy. I could feel her loosening up. Finally, I decided to go for it, having only seen what it looks like in a porn, I put my thumb in her and moved in an out as best I could. She could only take a couple minutes of this before she writhed and squirmed and screamed out in a big orgasm. I slowly pulled my hand out of her and laid next to her while we both calmed down a bit.
I don’t remember how the rest of the night went. We probably had sex. It was probably uneventful and pretty standard. She did ask me later whether I had my whole hand in there to which I replied with a playful, “yep!” I never asked her if that was her first time, or if she had any larger toys that she likes to play with. No idea what she is up to now and whether this was the begging of a long line of fisting she has had. I’ve had the pleasure of doing this with a few other women at this point, but it was that first time that made me realize the exhilaration of it all.
Source: reddit.com/r/gonewildstories/comments/mz90mh/the_first_girl_i_m_fisted