Dear Diary Ch. 09

Dear Diary,

Here I sit naked before my computer, yet again, fondling my penis to make it hard.

Yet again, I masturbate to real-life memories, instead of fantasies. What I am about to write actually happened to me.

What I'm about to write of, is the matter of getting caught masturbating. Or fucking.

It's something that kind of whipsaws me in the arousal department. It's something I dread in practice, but fantasize about in theory. For the record, it's something that has me hard now as I stroke my cock.

When I fantasize about something risky, it's because I desire it, and fantasies can lead to reckless abandon and a form of playing chicken with myself; of putting myself at risk of getting caught with my pants down because it's what I really want to happen.

Sometimes.

There was a guy I knew in high school. I later heard of an episode at college when the lights in the lecture hall were dimmed for some film or slide show, and when they came on again, it's fair to say those seated near to him were surprised to learn he'd been choking the chicken in the dark.

Didn't bat an eyelash. Saying not a word, he stuffed his cock back in his pants and zipped them up. I believe everyone was too astonished to react.

This was the silent wallflower guy I thought I knew in high school.

I don't have that kind of brass, and getting caught has been mostly aspirational for me.

Even so, I did get caught once in college. I was catching a quick afternoon nap between classes when it occurred to me it would be nice to pull my cock out and jerk off under the covers. I'd been enjoying myself for a couple of minutes when I heard the door to the room I shared opening. Naturally, that caused my cock to aim for the moon and hit--not London, certainly; not even the ceiling.

But it did leave me with a sticky front under the covers, and my roommate and a mutual friend from our hometown looked down on me obviously keeping my blanket away from my chest.

I don't remember who said what, or who was the more mortified, but my unwanted visitors shut the door and allowed me to clean up my mess while retaining a shred of dignity.

So. The experience wasn't traumatic, much less sublime. At most, it was mildly embarrassing.

***

There is one environment, however, in which I tilt at the windmill of getting caught. That would be the adult theater in the sex shop near where I live.

That I sometimes patronize to this day.

I pay the cashier, head to the theater door, and wait to get buzzed in. Once admitted, my eyes adjust to the darkness and, if I'm lucky, I see a number of men furtively adjusting their clothing, no officer, we weren't doing what you think you saw.

It only takes a moment to realize I pose no threat, and another moment for everyone to pull out their cocks and resume masturbating themselves or a partner, or sucking cock, or... and by this time I have my own cock out, looking for a partner, or, failing that, just jerking off while watching the show. Not the one on the screen; that's straight porn.

So, when the buzzer sounds a few minutes later with me cock in hand like the rest of the guys, I too hurriedly pretend I wasn't just engaged in gay sex, or, more deliciously shameful, solitary masturbation.

In the gay theater I sometimes take that game to another level. The times I've gone there I haven't seen much action. I do enjoy masturbating to the gay porn, however. After a while, when I'm hot and bothered, I take off all my clothes and jerk off naked as long as as I can last in hopes of someone walking in on me. It's the only place I've actually tried to get caught, in hopes the sight of my my naked body and visibly stiff prick would find an appreciative reception. Not quite getting 'caught', exactly, but exciting anyway.

Back to the straight theater.

Once I did get caught while being assfucked in the theater. Yes! My partner and I were masturbating each other when I asked him "Would you like to fuck me?"

"Sure! But suck my cock first!" he says.

I'm only to happy to oblige, and at that time, didn't worry too much about condoms. I kneel and lick his shaft. It feels like corded steel wrapped in warm flesh in my mouth. He swivels his hips to make his cock go in and out. The memory of his cock in my mouth makes me stroke mine as I type!

I stand, unbuttoning my shirt and dropping jeans and underwear to the floor. I'm now naked from the ankles up. He lubes himself and hands the packet back to me. I run my finger up and down my crack and inside my ass. When I feel my finger inside me, I long for the pleasure to come.

My partner positions himself behind me. I place my hands on a chair back. He brushes the tip of his cock against my bud, and I pucker. Next he exerts steady pressure on me; I push back. He presses again and again. I feel him working his cock into me, in and out, deeper each time, until it's all the way inside me.

I love how that feels! Brief intermission while I masturbate to the memory.

He pauses, deep in my ass, before moving in and out.

During this, I've been working over my cock. Now he's inside me, I can stay hard without stroking myself.

We fuck in earnest! I'm on cloud nine, but also feel a tension born of anxiety about someone walking in on us. The thought both frightens me and spikes my arousal even higher.

My asshole clamps down on my partner's cock. The sensations I feel from his cock moving in and out of me grow more intense. My cock rises and twitches.

Delicious dread and anticipation about someone walking in on us makes my pelvic floor contract and my cock to grow hard as diamond.

After a glorious time being assfucked, I feel inevitability mounting.

My asshole contracts around my partner's cock I'm about to lose control...

... And the door buzzer goes off, like a gunshot.

A couple, man and woman, come in the theater just in time to watch my no-hands prostrate orgasm. Streams of cum fountain out of my cock. It feels wonderful: I'm glad to have been caught buttfucking--and by a straight couple, at that--to feel that extra turn of the screw, that extra goose to my arousal!

That was a good time. Oh, yes!

On another occasion I don't hook up with anyone and, after a long spell of jerking off, I call it quits.

What happened next would have gone very differently if I hadn't decided I might as well have an orgasm before leaving the premises and masturbated in the men's room. I left the stall door ajar in faint hope of attracting a partner, but no joy: The experience of cottaging remains in my future yet.

Once I shoot my wad and clean up, I leave for the parking lot.

A car is parked next to mine, to my left. I'm fishing for my keys when I glance at it. I see a man in the driver's seat, and he has his stiff prick out of his short pants, and he's jerking off right there in the parking lot. I do a double take, even peer in the passenger-side window at him to make sure.

If I hadn't just had an orgasm minutes earlier, I do not doubt I'd have gone round to the driver's side and pulled out my own cock. I don't know if he wanted to suck me off, or do mutual JO, or maybe he wanted me to suck him off; all I know is I wasn't capable of anything like that just then.

Probably just as well, as I'm pretty sure I could see the sex shop security guard looking our way. So, I drove home.

***

As you can imagine, the experience found its way into my masturbation fantasies in no time.

It also led to an odd episode in which I did get caught, after a fashion.

There's a gay website I patronize, mostly to take part in webcamming circle-jerks and quietly seek new venues for anonymous hookups. It also allows me to upload photos and videos. I conceived the idea of taking a selfie of me masturbating in my car and uploading it. This is not as easy as it may sound: I have to free my cock and masturbate with one hand while trying to get off a good shot with the camera in my phone with the other, ordinarily a two-handed business. Without getting caught.

I try this more than once, and have wretched luck getting a good shot. Still, it feels hot to furtively masturbate, edging in the parking lot.

One day, while thus engaged, several things happen in quick succession. A delivery truck drives behind me. This distracts me from my edging, and I have an orgasm, right there in my driver's seat in the sex shop parking lot. Next, a car pulls up and parks next to mine. A woman gets of of the car as I frantically try to conceal my cock and the evidence of my orgasm.

Another car parks next to me on the right! The woman goes to that car and hands a package to the driver. It's gift-wrapped. She returns to her car, and both vehicles leave. I have no idea if they paid any attention to my mostly-exposed cock, which I could not have better concealed without drawing attention to what I was doing.

Once more alone in an otherwise unoccupied parking lot, I clean myself up, stuff cock in pants, and do up my fly. I exit the car to throw my soiled tissue in a convenient trash receptacle, hoping I'm not too obvious about it for the security cams.

I drive home, face burning, and give up on the selfie thing.

Even though I don't know if anyone saw me jerking off in the car, it sure felt like I got caught!