Jerking off together but "Just Friends."

I have a fantasy about masturbating with a friend when I was just a teenage. Actually, the fantasy is about how I should have - but didn't. A gay friend was to be my guide to fulfilling my fantasy.

When I was about twelve, I had been a frequent reader of lusty stories and would get a dirty magazine whenever I could. I hadn't yet masturbated but had played with myself even poking my stiffening cock onto any hole I could find, mattress, rolled towel-anything to try it out but ejaculating was a mystery.

One day the mystery ended when I took playing with myself to a new level and came for the first time. I was astonished and terrified. I thought I'd hurt myself. But practice makes perfect and soon I was jerking off to as many big-breasted women in magazine as I could.

This fantasy began when I was about thirteen, when a friend stayed over at my house. We shared a bed and once under the covers he pulled out his cock and started stroking it. He asked if I had jerked off yet and being embarrassed, I said no. He offered to help me. The offer wasn't exactly refused but I chose not to join him. Instead we talked about his s****r and whether she had seen his " 10 inch cannon." Seems she had be didn't care much.

He had a large cock. While maybe not ten inches it was enormous to me. It lay heavily on his belly and as he played with it, it rose up, a drop of precum on the tip. He would probably have stroked himself off except that I rolled over and pretended to sl**p. Without me joining him, I guess the fun was gone so he went to sl**p.

The morning was awkward. I was a bit ashamed and had a hard time talking to him. We became estranged after that. I had wanted to jerk off with him and tell him about my own experience but, I had other secrets that I didn't want to share so, I stayed away from him.

Today, in my retirement, I still have a fantasy about jerking off with another man and sharing experiences but felt it very unlikely to happen until recently.

I have a very good friend who's gay. We go to bars together and he's always teasing me about what I'm missing by being straight. Gay bars are exciting. It's lovely to have a man make a pass at me or see someone looking me over. At my age, I qualify as a "bear".

We were walking back to his place one evening, after many beers at a bar featuring male strippers with cocks on steroids and he asked me if I'd ever had a gay experience. I didn't tell him about the gay and tranny porn I often stroked off to but told him about my experience with a friend when a teenager and expressed mild regret that I hadn't jerked off with my friend those many years ago. While I was ashamed at the time, I never saw what we might have done as homosexual.

My gay friend said, "Well, maybe it's about time we helped you fulfil your fantasy and get on with your life. Sounds like you have a bit of sexual baggage to unload. Come back to my place. We're friends. We can jerk off together. Nothing more."

I had enough beer in me and had been turned on by the way the strippers swung their oversize dicks so I said yes, quickly, before I changed my mind.

We had another drink in his apartment and then we both stripped down and lay on he bed. His cock was long, thick and circumcised. It lay semi-hard on his belly. Mine was more timid, a noodle trying to hide. "That won't do." he said, "Start stroking it or I will." Him touching me wasn't what I had intended so I started to stroke and soon, I was getting hard. He complimented me on the length of my dick which, never seemed to be as long as it was now. Soon, we were lying there in our own worlds, eyes closed, stroking.

I looked over to sneak another look at my friend's cock. It had grown a bit and the helmet was an angry purple. He was stroking it slowly, pulling it a bit at each tug away from his body. And his cock responded. I noticed that I was getting harder as I watched him. A drop of precum had dribbled from my cock tip onto my fist. He turned and remarked "You have been holding back a lot eh! You should come huge." At this, I stroked with renewed vigour keeping my eyes on his lovely penis.

"Have you ever touched another man's cock?" he asked. I snapped a quick "No" to ensure myself that I was in control. "Take my cock in your hand." he ordered.

Without hesitation, I wrapped a fist around his meaty cock. I was breathing heavily and gasped when his cock leapt in my hand. I was in some shock over what I was doing but I was doing it anyway. I took time to examine the head, the tip with his own precum, the hardness of the shaft and then the roundness of his ballsack that had shrunk up tight against his body.

He moaned appreciatively and rolled over slightly so he could watch me better. My cock was jumping around, with a mind of it's own.

"Take your cock in the other hand." he said and I did. Interestingly, I've always jerked off with my left hand when I wanted to feel like it was someone else doing it. Now I was doing that while stroking another cock with my right hand.

I admit that I liked this. His cock had a real heft to it and it was constantly jerking as I moved my hand around. My own cock was about as engorged as I'd ever seen it and at my age and this was a delight in itself. I wanted this to go on for long while because coming would end all the pleasure of the sexual tension. I was also anticipating, a fantastic, full-body orgasm.

Now that I was doing all the heavy lifting, my friend laid back. He gave instructions from time to time. "Rub my precum onto the tip. Long slow strokes. Grip by cock harder. Now faster." I obliged because he responded very well to what I did and my own cock was staying very hard with every order and every stroke of my left hand.

I lay back with my eyes closed, and soon felt his hand on my cock pushing mine away. He had large hands and they pretty much covered all my cock except the tip. He stroked gently, moving occasionally to massage around the helmet and cup my balls.

"Are you ready to cum?" he asked. I was and said so with a thrust of my hips. "Oh yes, we are ready.' and he pumped me harder emphasizing each stroke. I tried to match his pace and soon, we were on our way to coming together.

Our orgasms were strong and shook our whole bodies. We each moaned loudly and thrust our hips as cum shot onto our chests. Some of mine, which was thinner and almost transparent, reached my face while his larger amount of cum, white and milky, flowed over his fist, pooling in his belly button.

Like all masturbation, when it ends, it’s too sudden. A few more strokes and some playing with our softening cocks and we were ready to roll over, get up. and get clean. He had towels ready and in no time, it seemed, we were at the front door hugging goodbye.

"So there's some old baggage unpacked." he said. "It looked like you were holding back a lot from the amount and the f***e of your cum. Next time, maybe I can help you get over any feelings you have about getting your cock sucked by a guy," he k**ded. I knew we would keep our relationship friendly and never go back to what happened this evening. It was good. I felt great.

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Categories: Masturbation
Posted by smallfurrycreature
2 years ago    Views: 891
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3 months ago
I as you had the opportunity to jerk off with a friend and said I didn't to it. Now after 60 years wished I had. It may have opened the door to 69 and anal--will never know
1 year ago
Nice story, thanks!
2 years ago
When I was a kid 13 thru 17 My best friend and I use to jack off together. We never touched each other but was great fun.
2 years ago
My story is the same as the one below. It was over twenty years later before I sucked a cock again. Glad I got over that baggage....Excellent story, thanks.
2 years ago
As a teenager I started off with a friend learning to jerk myself off,then jerking each other off.Eventually we sucked each others cocks,taking turns for 1 min. at a time.As we became more comfortable with sucking cock,we both started to enjoy sucking as much as being sucked.Evan learned to like having him cum in my mouth and swallowing.Did it for about 3 years then found chicks and never have sucked another cock, but still think about it and sometimes fantasize about it.
2 years ago
I actually got a slight bulge reading this. Sounds like something I might try with a another crossdresser, transvestite or she male. Not sure about a guy unless a woman stroked us both off.
2 years ago
It seems most men jerked off with a friend when they were teenagers. I missed out so I wrote this story.