A girl I was casually dating (no sex yet) asked if she could masturbate my cock.
She’s not really my girlfriend but we just like to do stuff together. Yeah, I admit I would like to have sex with her, and it did actually happen, but not like I expected.
We had casually dated three or four times and I had been working up the balls to make a move on her. Then she totally surprised me.
“Ken,” she said, “ I know this is totally out of the blue and we really don’t know each other very well. I know you would probably like to get into my pants, but that’s not going to happen. But how would you feel about letting me jerk you off?”
I couldn’t believe I actually heard her correctly. She wants to jerk me off? I really didn’t know what to say although of course I would welcome a hand job. Who wouldn’t?
“I must say I am a bit shocked by your question, but I would never turn down getting wanked by somebody as attractive as you. But I am curious. This request seems a bit strange.”
“Yeah, I know,” she replied. “The thing is I really want to be a virgin when I get married. But I have to confess that I am obsessed with men’s penises. I look at photos and videos of men’s cocks on the internet and I just have an overwhelming desire to wrap my hands around a hard cock and make it spurt.”
That’s all I needed to hear. We were at my apartment watching a movie on TV. I asked her if she wanted to do it right now and she was all for it. I quickly got my pants and underwear off and my cock immediately started to get hard just knowing what was coming. I sat down on the sofa and gave my dick a couple of tugs to get it to full hardness.
“Oh Ken,” she exclaimed, “I was hoping you would have a big dick. I guess you could call me a size queen. How big is it?”
“It’s not that big,” I replied. “Just short of seven-inches but I guess it is thicker than normal.” As I looked at Jill’s eyes, I could see she was totally focused on my cock. There was a gleam in her eye and I could tell she couldn’t wait to get her hands on it.
“Can I touch it?” she asked hesitantly.
“Of course, that’s the whole idea. You can’t jack me off without touching it.” We both laughed and that kind of broke the ice.
She grabbed my cock with both hands and started jerking me off. “Ken, I’ve never done this before so you need to give me input on just what to do to make it feel good for you.”
I proceeded to give her tips and input on what felt the best. She was an outstanding student and within just fifteen or so minutes she was expertly jacking me off.
“Ken,” she breathlessly said, “you’ve fulfilled my greatest fantasy. I really love jerking off your hard cock. I could do this all day.”
She said she wanted to make it last as long as possible so I explained how any time I got close, I would tell her to stop for a couple of minutes and then resume. The whole time she was jerking me off, her eyes never left my dick. She was truly focused. Finally, I really couldn’t take it anymore and told her I had to cum. She was excited to see that happen so I told her to increase her grip on my dick and to speed up. Which she did and a few moments later the semen started spurting out of my cock.
Due to all the buildup, the spurts were not only super powerful, but just kept cumming. I don’t remember ever pumping out that much cum before. But she had been jacking me off for over an hour which was what allowed it to happen.
She squealed in delight as I shot stream after stream of jism all over both of us. She didn’t care. She loved it.
This set the stage for a steady stream of hand jobs. She was jacking me off four or five times a week. Then she threw another surprise at me.
“Ken, don’t take this the wrong way. I love jacking you off and have no intentions of stopping. But I keep seeing all the different cocks on the internet and I am curious what it would be like to jack off some other guys. Could you line up some buddies that I could masturbate.”
I was bit taken aback by this request. But despite her jacking my dick on a regular basis, our relationship was still pretty casual. There was no actual romance going on so it didn’t bother me that she wanted some more jack off partners. I knew a couple of guys who I was sure would be up for it.
I called my buddy Vince and told him what was up. At first he thought I was pulling his chain, but finally realized I was serious. Of course he was on board.
When he arrived at my apartment, Jill took over and told us what she wanted. All three of us would get totally naked. She would take turns jacking both our cocks but reiterated that no other sex would be involved. We could feel her titties but her pussy was off limits.
So we got started. As I expected she spent more time with Vince’s cock than with mine, which was to be expected. I had no problem with it. Then she surprised me again.
“I saw this video on one of the XXX-rated sites where a girl put two guys cocks together and then jacked both of them at the same time. I want to do that.”
So Vince and I got on the bed, sitting facing each other. Vince had to put his legs over mine so we could get close enough that our nutsacks were touching. Then Jill poured lubricant over both cocks and wrapped her hands around them and started jerking. This felt amazing. But the trick was to enhance the feeling that Jill was giving to our two pricks. To do that, there had to be some friction where the underside of our two cocks were touching. That underside, where the frenulum exists, is the most sensitive place on a man’s dick. As Jill gripped our cocks, first she would push them toward Vince and then back towards me. She continued this back and forth movement. This movement caused our two pricks to slide up and down against one another and felt amazingly good.
From time to time she would grip each cock separately and rub them together. Feeling our two cockheads massaging each other was fantastic. From time to time she would let go of our shafts and grip our cockheads, massaging them with her fingers.
Any time either of us got close, she would stop a bit before continuing. This went on for at least thirty minutes before she decided she wanted us to cum. I was hoping that we could somehow achieve a simultaneous orgasm because I knew it would be hot as hell to see both cocks spurting fountains of semen at the same time.
Somehow luck was with us and when my dick started spurting, so did Vince’s. Jill was in seventh heaven with two dicks ejaculating fountains of cum at the same time. Clean-up was a bitch, but well worth it.
The three of us continued to get together regularly and then Jill wanted me to bring on another guy, And then another. The peak of her masturbatory fantasies were achieved when I got four other guys involved. The five of us stood in line, naked, with our erect cocks standing proud, as Jill worked her way down the line jerking each of us off to a great orgasm. She would aim each dick at her tits and after getting us all to orgasm, her tits would be dripping in semen.
(This is, of course, a fantasy.)
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