These are some of my most memorable masturbation sessions. I hope you can enjoy reading them and perhaps reflect on some of your best experiences. Please share them if you do!
This is one of my more memorable experiences that I had with my girlfriend at the time.
Chloe and I had been together for roughly a year at the time, and had been mutually masturbating each other for most of that time. All the sexual stuff happened at my house since we had no privacy whenever I went to her house. She would arive, we'd head to my bedroom and within an hour or two we'd both be well into exploring each other all over.
About a week before this particular experience, Chloe had rung me to chat over the phone like we did every couple of days. Except this time she was a little more excited as she had something to tell me. Since I had known her, she'd never masturbated by herself. I was the first to give her an orgasm, and she relied on me for her masturbation purposes for that first year together. I was encouraging her often to try masturbating by herself so she could enjoy the pleasure on a daily basis (we were only seeing each other weekly.)
She told me over the phone that she'd successfully masturbated to orgasm the night before. She'd apparently been trying all week and finally managed to bring herself off. I was excited to hear the news as the thought of my girlfriend masturbating really turns me on.
She came around to visit me a couple of days later. We locked ourselves in my room and laid down on my bed as we usually did. She climbed on top of me and we started kissing heavily, making out. I could tell she was getting horny as she started grinding herself into me as we kissed more and more passionately. After a short while she broke away and asked me if I would masturbate myself for her. She also apparently was turned on by the thought of watching her partner bring himself off.
I agreed to do it, but only if she'd show me her newfound talent and masturbate in front of me too. She was shy about it initially, since she'd taught herself to masturbate in an odd way (so she thought.) But she was so horny she eventually agreed to it.
So I took off my boxer shorts and shirt as she stripped off her jeans and top leaving her panties and bra, and leaving me naked. She climbed on top of me again momentarily as we made out and she ground herself into my exposed penis, making me fairly horny. She eventually broke off the kiss again and gave me a cheeky smile before sliding off to lay next to me on my right.
I grabbed my lube and asked her to lube me up. She rubbed it all over my penis and gave it a few quick strokes to get me going. I started masturbating myself as she watched on. She was entirely focused on what I was doing, so I had to remind her to her part of the bargain. She again shyly told me she was embarassed, but I just told her that she wanted to masturbate, and she blushed and agreed.
It turns out the way she taught herself was to lie half on her stomach, and reach her hand into her panties to rub her clit. That way she had room to rub, but could also half-hump the mattress at the same time. As she reach down into her panties and started rubbing her clit, I was almost all ready to cum. She let out a small moan which didn't help my condition. As she masturbated next to me, she had her eyes entirely focus on what I was doing to myself.
After only about 5 minutes I told her I was ready, she told me to wait so we could cum at the same time. As her breathing got heavier and she started giving out short gasps, I could tell she was getting close. She then gasped out 'N.. now.' And I gave myself a few quick strokes as I started shooting my cum onto my chest and stomach. This set off her orgasm and she gave out a sharp gasp and started pressing herself into my side as she rubbed her clit to what I can only deem as an amazingly powerful orgasm.
Once we both calmed down a bit after laying there for a few minutes. She climbed on top of me again (with my cum still all over my chest) and just gently kissed me as she slowly humped her body into me. We stayed there, kissing softly like that for about 10 minutes before she told me how amazing that was, and how she was still embarrassed about masturbating herself in front of me.
I told her how awesome she looked doing it, and how horny it made me feel. She said a similar thing about me. Eventually we both stood up and cleaned the cum off our chests and hands. That remains one of my favourite masturbation experiences and memories. It was so hot watching Chloe masturbate next to me, and I miss those early experiences a lot.