Dear Diary Ch. 03

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More sweet fantasies for masturbation.
1.6k words
4.1
2.8k
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Part 3 of the 10 part series

Updated 06/12/2023
Created 12/15/2022
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HenryApril
HenryApril
22 Followers

Dear Diary,

For me, the peak of sexual pleasure comes when I feel a man bring me to orgasm by massaging my prostrate with his erect penis. A matter of expression, never more personal: As he voids his balls inside me, I void mine into the air, sharing with him a joyous spasm that leaves us both drained.

All these tales take place in a bathhouse about an hour from where I live; all of them actually happened much as I describe.

The first time I took another man's cock inside me began in a half-assed maze. It was not much more than a couple of benches and a curtain around a kind of glory hole. (It has since been converted into a lounge. There's a plush pleather chair in it that I hope to recline in while masturbating someday.)

I enter and sit next to a Latino man about my age. We're close to each other, but not so close that our thighs touch, and masturbate together a while. I work up my nerve and place my hand on his cock; he clutches mine. Perhaps a minute passes as we masturbate each other.

. . . The memory is sweet: As I sit at my computer, naked now, as I was then, pumping my cock, it still makes me hard.

All this while I had been working up my nerve. At last, I pop the question. I whisper, "Would you like to fuck me?"

"Sure!" he says.

We stand. I help him don his condom, which I lube before lubing my own passage. I turn away from him and bend over slightly.

I feel the tip of his cock at the bud of my asshole. Before coming to the bathhouse, I fingerfucked myself in the shower so I will be ready for this. It takes little time for my lover to penetrate me. For the first time in my life, I feel a man's cock slide all the way in and out of my rectum!

I stroke my own cock as I feel him thrusting and grinding inside me. I'm new to this: more than once I straighten my back, and my lover gives me a playful shove so that I bend over and he can force his cock deeper inside my ass.

Minutes pass before I feel him jerk and shudder as he comes in me. As wonderful as my experience has been, I'm nowhere near coming myself. I ask him to masturbate me, and he cheerfully brings me to orgasm that way.

We go our own ways after that. Later that day, I run across him again, and he gives me a little nod of the head, and a not-quite-wink, of complicity.

After that first time I fuck for many men. Among those occasions, sweet all, a few stand out.

I sit naked on the bed in the small room I've rented. This one has no video to play porn, as I recall. It's daylight, and I leave the light off. I stroke my cock gently while watching potential lovers pass by my open door and watch me jerk off.

One enters the room. I look up at him as I continue masturbating. He reaches down and takes my cock in his hand. I grasp his. For a minute or so we jerk each other off.

"Would you like to fuck me?" I ask. "Sure!" he says.

I lie on my front while he puts on a condom and lubes us both. It takes little time after I first feel his tip pushing against my asshole for him to be all the way inside me. His hips rotate back and forth as his cock slides in and out of my asshole. I surrender to the pleasure of feeling him plow me.

To my surprise, he stops short of his orgasm, and well short of mine. He pulls his cock out of me and lies down beside me. I roll over to face him. He runs his hands up and down my backside before taking my cock in his mouth.

It's some time before I realize I'm not wearing a condom, that his mouth and tongue work over my unprotected, naked, cock.

Up to now, I've always worn a condom for oral sex. That I just let a man take my bare cock all the way inside his mouth is a surprise as dismaying as it is pleasurable. "I broke a rule!" I cry, before it feels too good to stop. "I always wear a condom for this!"

My lover lets me pull out of his mouth, taking my repentance in his stride. I put my hand on his cock and masturbate him until I feel his orgasm, and his cum coats my hand. During his afterglow I use it as lube.

I don't remember what I do after he leaves, but I know I find another lover to relieve me of the tension I built up during this episode. Never leave the bathhouse without at least one orgasm of my own!

Next is a guy who fucked me more than once. Colombian. He's short and muscular, and has a thick muscular cock. His response to my safe-sex worries about unprotected oral sex during foreplay is to lick the shaft of my penis without taking my mushroom tip into his mouth. I love the feel of that!

He lets me run my tongue over his shaft. That's how I acquire the taste for running my tongue up and down a man's cock.

After foreplay of that nature, he fucks me with his short hard cock while I jerk myself off. Orgasms all around!

It's on a later visit that I masturbate naked while sitting on a side bench in the large video room, the one with a bed in the center. Across the bed from me are other men, also naked. Also masturbating. It's not quite an orgy. We watch each other a long time.

I spy a wiry Asian guy, about my age, or a bit younger. He pumps his cock with an expression that says "what are you looking at?" This has an appeal. I rise and walk across the room, taking a seat next to him, but not too close. I resume stroking my cock, and enjoy watching him stroke his at close quarters.

It's a subtle business, deciding when to shift a hand from my cock to someone else's. In a bathhouse, one expects that sort of thing to happen. For me, however, it's still a delicate calculation: Grab him, or wait?

The spirit moves me, and I take his cock in my hand. I guess the same spirit moves him, as he starts pumping my cock on the spot. We stroke each other a long while.

There are several other men in the room, men who watch us masturbate each other. That adds extra spice to our play. To this day, I find it makes gay sex even better when other guys watch me and my lover pleasure each other.

Thinking back on it, I can't tell if it's my own mounting arousal, or my judgement of my partner's arousal, that prompts me to ask him "Fuck me?"

"Suck my cock first!" he commands. This time, I'm ready for it. Aching for it. Knowing it will feel wonderful. I kneel between his legs and wrap my mouth around his cock. I suck on it, waggle my tongue on the bottom of it, and move my head back and forth so he fucks my mouth.

All the same time I masturbate furiously. I know what we look like—more than once I've jerked off while watching other couples do exactly what I'm doing now—and the knowledge other men masturbate watching me suck my lover's cock while I jerk off makes me even harder than before.

After I've blown him a while, I'm more than ready for him to buttfuck me on the bed in front of everyone else in the room. Working over his cock with my tongue makes me completely shameless. He has other ideas, however. Next to us is a curtained area used as a glory hole. He wants us to fuck in there, without an audience.

I'm not disappointed at all: I'm about to get assfucked! We go behind the curtain. There's nothing inside but a stool. I place my hands on it and lean forward, while my lover prepares his condom and lubes us both.

My heart pounds and veins in my head throb; I feel the hard slender cock I just sucked so sweetly push against my entrance. It takes a minute, but I feel myself yield. During this, my hand never ceases jerking me off.

Once his cock is all the way inside me, we fuck like minks! I feel him thrust in and out of me. I make my hips gyrate in and out. The pleasure in my asshole and in my cock reinforce each other. My arousal goes through the roof!

Only one thing can make this better. "Grab my cock!" I cry. My partner replaces my hand with his and masturbates me as we fuck.

Things now take a rhythm of their own. My asshole alternately relaxes to take my lover's cock freely, and clamps down to sieze it. Over time, my asshole squeezes his cock longer, and harder, than ever. His hand pumps my cock furiously.

Reader, I cannot say which of us has his orgasm first. All I know for sure is, it leaves me drained; I expel every last drop of cum from my balls.

. . . As I do now, eyes closed to enhance my focus on my memory, head thrown back, last drops of my cum fountaining over my fist.

Not going to have any difficulty falling asleep after this!

HenryApril
HenryApril
22 Followers
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