I Caught Her And It Changed My Life, Part 1

I was a wild kid and got in trouble a lot at home, school and some minor legal things that put me in juvenile detention a couple times. 

My mom was an alcohol and drug treatment professional then and hired a new counselor who had a daughter my age. Her daughter had also been in trouble a lot. I had mostly pulled myself together at 17. I started college a year early, had a job and a car. My mom and her colleague thought, because of our similarities and how I had pushed through my troubles that I would be a good influence in her daughter’s life.

She was cute and cool and our similar past made us quick friends. We spent a lot of time  together at each other’s houses, going on hikes, drives in the countryside, hanging with my friend group, sharing music and other 18yr old things.

It took about 4 months for us to start dating.. At 18 I’d had 5 sexual partners. They were all short lived and different but equally great experiences for a teenage boy.  I thought I was worldly but this girl, ( let’s call her Jean) ,was on a whole different level. 

I was used to pursuing a girl and  it taking a lot of time to get into make out sessions, clothed petting , possibly leading to get a hand up the shirt and feeling a bra or touching breasts. Being a teenage boy, hoping each step could eventually lead to sex. 

Jean's mom was a sex positive person and had always been open with her about sexual pleasure. They had discussed masturbation and orgasms, alternatives to intercourse with a partner that still fulfill the need of sexual release and safe sex practices. Sexual expression was normal for Jean so she didn’t waste any time. The first time we had privacy for a heavy make out session she put my hand up her shirt and showed me how to unhook her bra with one hand. It didn’t take much time after that until we were sexually active whenever possible.

One afternoon we were at my mom’s house with some of my friends. We were all going to a get together at a different friend’s house and I wanted to shower. Jean and my friends thought it would be funny to prank me so she quietly snuck into the bathroom with a pitcher of ice water and poured it over the shower door  on me as I’m obliviously shower singing with my eyes closed. It was a shock and funny to me and everyone else. I didn’t forget though and was patiently waiting for a revenge opportunity.

A couple weeks later we went to a dance at my community college. Her and my mom were out of town at a conference for a couple days so we had her house to ourselves that night. We danced every slow dance with our bodies pressed together, talking about what we could do when we got home. We left early in anticipation of our evening alone. As soon as we got home we slow danced without any music in the empty living room. Standing behind her, gently swaying with my arms wrapped around her waist, I started to kiss her neck and ears. Jean tried to turn around but I held her there, enjoying the feeling of her ass pressing against me. I let my hands wander up her shirt, loving the way it felt to cup both of her large breasts in my hand from behind. She let out a soft gasp and I reached my right hand between her legs. Her outer labia had spread in arousal and I could press the seam of her jeans between them to put gentle pressure on her clit. She moaned at the touch and her hips shifted, pressing her ass insistently against the erection trapped in my pants. I let her turn and she said she’d never been so turned on with her clothes still on. Neither of our clothes stayed on for long. She took me to the floor, climbed on top of me and guided me inside her. It didn’t take long for us to cum together. 

We cuddled in the afterglow for a while and she said she wanted to shower. I put on some clothes, went to the couch and turned on the as she grabbed her pjs and headed to the shower. I heard the shower running as I got up to get something to drink. I remembered her prank and knew she wouldn’t be expecting retaliation. I filled a glass of ice water and headed to the bathroom. I quietly opened the door and saw her, naked, lying on a towel on the floor, legs spread, knees bent with an electric toothbrush on her clit. It could have only been a second or to till I apologized and closed the door but, the image burned into my mind. I can still see it vividly all these years later. I went back to the couch and drank the ice water thinking about what I had just seen.

I knew women had orgasms but, I had never considered that they have the same desire to masturbate as I did. I felt weird, we had just finished having sex so it wasn’t long enough for me to have another full erection, but I felt something happening. I pulled myself out of my sweats to quickly look. I was so thick and the head was swollen and purple. When I touched it I was immediately filled with an ache I didn’t understand and almost hurt. I pulled my sweats back up and sat there confused,  trying to process everything.

It seemed like forever until Jean came out of the bathroom and sat down on the couch by me. I apologized again. She was clearly embarrassed but told me I didn’t need to apologize. She was more concerned about reassuring me that her masturbating wasn’t because our sex wasn’t satisfying and didn’t want me to feel insecure about my performance. That had never crossed my mind. I was still stuck on the epiphany that girls have the same need to masturbate boys. 

She explained to me that women can have different kinds of orgasms. That her orgasms during sex had a different feeling than clitoral orgasms and vibrator clitoral orgasms felt different as well. I technically knew that women have the ability for multiple orgasms and that men have a refractory period that usually prevents that but had never wrapped my head around all the implications of that knowledge. She told me that the orgasms during sex were deeply satisfying and flowed through her whole body but sometimes they made her want the super intense vibration orgasms that light ever nerve ending of her clit on fire, filling every part of her genitalia with pleasure until her clit bursts in an orgasm that shoots pleasure straight into her brain. She told me that no one had ever seen her masturbate before, that although her mom was open about it and taught her about electric toothbrushes, talking about the actual personal experience isn’t something you share with your mom.

I was still aware of the ache in my pants but, I was so fascinated with every word that came out of her mouth, that feeling was just in the background. I assured her I was ok and deeply interested to talk about this more. She asked me if we could go lay down in bed. I was overwhelmed and more than ready to cuddle.

We climbed in bed, she put her head on my chest, her leg over me and kept talking. She told me that she was 100% sure that I masturbate. She asked if I had ever been caught. I told her I hadn’t but my mom always knew the missing wash rags were under my bed. She asked if I’d ever let anyone see me masturbate. I hadn’t. Then she asked if I’d be willing to let her watch me sometime. I was ridiculously embarrassed but I agreed I would at some point. As soon as those words came out of my mouth the ache in my genitals came to the forefront and I got hard fast. She noticed my erection pressing against her thigh and put her hand on it and told me to relax. She pulled the front of my sweats down and grasped me. She asked me how long I’d been masturbating, as I answered she started slowly stroking me and told me when she first started. She asked how often I did it and told me how often she did. She had so many questions, the closer she got me the easier it was to answer them honestly and she would reciprocate with her own answers until I came.

That opened a wonderful door of dialogue, communication, arousal and pleasure that changed my life sexually.

The next parts of this story will be the individual experiences this day lead to.