Late Night Masturbation Session

‘Millie’ and I would often talk a lot on the phone in the evening. She was my middle school crush. At the time I was 13, she was going on 14. We sat next to each other in science class which had a detrimental effect on my grades. By the end of the year I had plummeted from the top science class to 3 sets below! This, all because of a school crush. 

Anyway, one night, I was on the phone with her when, whilst readjusting her position in bed, she told me that her phone had fallen out of her hand and was now resting on her boob. At first I was more shocked at this detail, but it made my penis incredibly happy!

I laughed at this comment. She asked me why I found it funny, to which I replied that I had always wondered whether girls liked to sleep naked, and that her comment had just assured my conviction. 

The phone call had now changed from our light conversation to what we had probably wanted it to have been about all along: sex! 

I was still a virgin at the time, so I asked her if she was as well. She replied in the affirmative, but that she had had a boyfriend earlier that school year and, when she had visited him at home, that they snogged heavily and even petted each other, but that was it. 

She then asked me if I masturbated. I was an avid masturbator, but I replied rather sheepishly, that I did every now and then. I then mustered up the courage to ask her the same, to which she also answered in the affirmative. 

All the while, my cock was rock hard and I was stroking it gently up and down. I believe Millie was doing the same with her pussy, because every now and then I could hear her emit gentle “ooh’s” and “aah’s”. She was clever though, as they were ever so quiet and I could hardly hear them, but it was enough to keep me curious. 

She had quite a few questions about male masturbation, how long it took, whether I did it whilst watching porn or whether I fantasised about other people. This last question was clearly and precisely thought out, but much of the blood in my body was currently being pumped at high speed into my shaft. I replied: “Yes, I do…” 

She asked: “Do you think about me when you do it?” 

I gulped and then sheepishly replied: “Yes. I have done multiple times…”

This broke the ice. She let out a very audible “ooh” which made me pre-cum. “Are you doing it now?” I asked. (How stupid a question, obviously she had been doing it, all along!) 

“Yes… And you?”

“Uhu…” 

This was back in the days of cheap Samsung smart phones which could be had for a few hundred pounds. Mine had a front camera. In this horny moment, I had a sudden brain wave. 

“Millie, do you have a cam?” 

“A cam? Why do you want to cam?” 

“So we can see each other… We could, you know…”

“Yes! Now that’s an idea!” 

I hung up and quickly opened up my cam app. I was also listening eagerly whether my parents had woken up. By now - roughly 11 pm - they would be in bed. I quickly got up out of bed and slowly and silently opened my bedroom door. The landing was pitch black and quiet. There was no slither of light under my parent’s door, so if I kept quiet enough, I would be able to have some fun. 

I searched for Millie and then called her. It rang a few times and then she picked up. 

This was the first time I saw a living and breathing girl, naked, outside of videos on the internet. There, on the tiny screen, was my crush; naked and dimly illuminated by her bedside lamp. She was sat upright against the headrest of her bed, I sat down on the floor. I turned on my reading lamp which illuminated me well. 

“Wow, that’s big!” was the first thing she said. 

I smiled and commented on how she was even prettier without any clothes on. She was a thin girl, yet athletic. She had milk white skin and I had only seen her pretty face; freckles, deep brown eyes, dimples and a small stumpy nose. 

The rest of her body was new territory for me. She had a tall slim legs which were stretched out away from her body, revealing her beautiful pussy. She had a good deal of pubic hair, more than me. She had small lips which were closed tightly together. 

She had a small petite type body which led up from her waist to her chest. There, I was greeted by two perky boobs. They weren’t massive, but I’ve never been a large boob type. Her’s were small but nicely formed with large nipples, which she was gently rubbing with her fingers.

“You look amazing.” I uttered whilst I stroked my cock. 

She then ran her hand down to her pussy and parted her lips with her fingers, revealing the pink inside of her vagina. With her lips spread using her index and ring finger, she slowly started massaging her clit with her middle finger. She giggled and let out a pleasing sigh. 

I reciprocated this by stroking my cock slightly quicker, making sure she heard my intensified breathing.

After a few moments of rubbing her clit, she pushed her finger down until she was at the bottom of her vagina. There, she folded her finger in and started moving her hand back and forth, sliding her finger in and out. 

“Wow,” I said, “this is making me soo horny!”

“Me too…” she whispered in reply. “I’m imagining your penis inside me…”

“Hmm, I wish I could be inside you right now.”

The game was on and we were both infatuated with this experience, listening to the sounds we were making, occasionally an “ooh” and an “aah” whilst we rode our way up to a climax. 

A few minutes had passed and the muscles in my penis were fighting a losing battle. I whispered to her, “I think i’m gonna cum…”

“Hmm, me too…”

She started rubbing harder. Now she was using both hand, one fingering away inside her pussy, the other massaging her clit. She started to arch her back and let out more moans, slowly getting louder and faster. I too was now pounding my cock and loading myself for this special moment. I could feel my body slowly losing grip and that an orgasm was imminent! Then, she started. 

She leant her head back and arched herself even more, her tits jiggling away as she rubbed even more. Then, she arched forward with her mouth open wide, as she let out a squeal before spasming and pulling her legs together. I too, felt all the nerves in my body tingle, at first in my penis, then shooting down my legs. It raced up my spine making the hair stand up on my neck and arms. I spasmed too before shooting my load, first way up into the air, before a second shot landed on my legs and torso. A few breaths later and a third shot was spat out of my penis which landed in the crevice between my legs and ball sack. 

“Wow,” I said, breathless, “I’ve never cum that hard before.”

She giggled, “Neither have I. That was really fun.” She then proceeded to lick her fingers, which glistened in the light with her delectable pussy juices.

I watched in amazement before she asked me if I had ever eaten my cum. I replied in the negative, and started cleaning myself up.

She then asked me if I would eat it for her, but I found that genuinely disgusting. I picked some up with my fingers, and then sniffed it. It was the first time I had smelt cum, and I didn’t like it. I stretched my tongue out, but just before I touched the liquid, I dried it on a tissue and said that it smelt awful. 

She laughed and also started cleaning herself up. At the time I didn’t know what squirting was, but I don’t think she had squirted. I could see a dark patch on her bed, but I think it was just some of the pussy juice that had leaked out.

After we got cleaned up, I hopped back in bed and felt quite tired. Millie, too, was feeling quite sleepy and we quickly said good night. 

The following day, I saw her during the lunchtime break in the playground. She was chatting with some friends, so I sat on a fence and waited for her. Eventually her friends walked off and she came over to where I was sitting. 

We chatted a bit about her day. Possibly we were overly shy about what had happened last night. I tried to talk about it, but she kept changing the topic. Then, when the conversation was over, she got up and stood in front of me. She then lowered herself down and placed one hand on each leg and she stared into my eyes. 

“Thank you,” she said, and then she gave me a wet kiss on the lips. 

We chatted again on the phone but we never masturbated together after that. I do think that she did it whilst we telephoned, but she never asked if we could cam again. Maybe she was waiting for me to ask her… 

It will remain the best masturbation experience of my life, something which left its mark on my mind.