This item was crossed off long ago and wasn’t even added to the list until later on because I forgot about it. I’m also not 100% sure if I’ve told this story before, but if so I apologize. This actually happened the first time I ever ejaculated in front of anyone and that someone just so happened to be “J”.
Now let me start off by saying this was a huge step in my sex life. I don’t remember all the sex that lead up to it – I’ll try my best – but I do remember that exact moment quite vividly. For those of you who are new or just missed where I talk about my issues, here is a refresher. My doctor put me on medication years ago to help my anxiety and though it has helped my anxiety tremendously, it has one interesting side effect. I realized one day when masturbating that I had to put in a bit of extra effort to get off and what used to be enjoyable felt like work. No matter how hard I tried, I was no longer Quick Draw McGraw – I’m not saying I woke up with super powers or anything, but I’m also not, not saying that.
It has its pros and cons; the major pro being that I can last quite long without the worry of cumming. My stamina is superhuman-like. However it would be nice to have that satisfying feeling of someone getting me off without me having to finish myself off. I explained this to “J” when we first met because everyone takes it as a challenge, but in reality it is just a forewarning. As I’m sure you can imagine, whenever I had sex it never ended with me experiencing an orgasm.
When I first started talking to “J” I knew she liked seeing a guy cum. I base this on the fact she told me the type of “porn” she would watch and some of the videos she had me send in the beginning. I was disappointed that I couldn’t do that for her in person until this particular day.
I remember “J” was on top of me riding my cock when she came; her legs quivering and thighs clamping shut around my body. After a few breaths she rolled off me and laid next to me. Still trying to catch her breath she wrapped her hand around my shaft and starting stroking me. It always felt good when “J” would play with my cock; despite knowing it probably wouldn’t end with climax.
“I want you to cum,” she said.
I remember thinking, “yeah good luck with that,” because it seemed like an impossible request. However she asked me to do something that none of my previous partners asked me to do.
“Masturbate for me,” she said.
It was a strange request to me because I had only masturbated alone. It brought me back to an old Dane Cook bit where he talks about how all men put on a show masturbating compared to sex as opposed to the way they masturbate alone. She was staring deep into my eyes and I knew I might as well try; I wasn’t that far off.
I wrapped my fingers around my cock and started stroking. I was doing it softly and seductively, trying to make it look appealing. Suddenly without warning “J” reached down and began squeezing my testicles; leaning over and kissing my neck. It felt overwhelmingly good – especially the way she was squeezing and massaging my testicles. I stroked faster and for the first time “J” saw how much effort I had to put into cumming; stroking so fast you could call me The Flash.
Then to my surprise I felt it building, I knew this was going to happen and because it was happening so fast and unexpectedly we never had a plan for where she wanted me to cum. I just assumed all over my stomach would suffice. I whispered “here is comes,” and “J” immediately moved down my body. The next part was kind of funny; I couldn’t hold it any longer and cum shot from the head of my cock. It shot past my head and hit the pillow beside me; narrowly missing my face. “J” was a bit startled and let out a small chuckle, but quickly wrapped her lips around my cock.
It felt amazing as many more pumps of ejaculate filled “J’s” mouth. It was an intense orgasm and she sucked my cock and squeezed my testicles until she got every last drop. Then to my surprise she swallowed it all and I knew then that I may have met my match. The two of us cuddled and joked about how I nearly took my own eye out. It was by far one of my favourite sexual experiences.
Until next time, happy cumming!