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My Prostate & Me

Story Info
My anal awakening.
755 words
4.28
118.8k
33

Part 1 of the 4 part series

Updated 10/30/2022
Created 07/15/2011
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Well, it all started about 20 years ago. I'm not sure if you know how tech support works. For me, I had either 10 calls or none. One day—I had 15. This is why tech support people burn out so fast. I had worked my ass off.

I was tired, horny and had no girlfriend. So I went to a rental girlfriend place that I'd been to once or twice before. You walk in and there's a lineup of girls, and I, being in my 20s, picked a girl the way most 20 year olds did—the one with the biggest boobs.

Almost 20 years later, I don't remember her name. I'm sure it was a fake name anyway so I'll call her Trixie. After we took care of the financials, we chatted.

Trixie was a stripper from Ft. Lauderdale with a silicone set, visiting her cousin. I told her I was there for some relaxation, as I had a stressful day. Turns out too stressful, as my "party" didn't want to start, as it were.

She offered a back rub. So I got facedown, she pulled out some lotion, and gave me a fairly good backrub. Trixie had me get up on all fours to check the situation, and still not much. Back to the backrub.

Trixie began to rub my ass. I spread my legs in order to find some room for the lads, as they were getting squished. She began to massage my balls and my ass crack. I started to grow. Trixie noticed, and decided to keep on keeping on. She was rubbing my asshole, while playing with my balls. She asked if I was ready to go nuts.

I figured she was going to blow me so I said yes, and went to turn around, but her hand was on my shoulder. Unbeknownst to me, she had put a condom on her finger and covered it with lotion. She gently slid it in my ass. I went from semi-erect to hard enough to drive nails. I'd never felt anything like that before. It was incredible. She asked if I was okay, and I could only moan.

Trixie giggled and went a bit deeper. I rose back up on all fours. As I was thrusting back involuntarily on her finger, she explained that she was massaging my prostate. I didn't care f she was chanting for Cthulu, it felt GOOD!

She asked if I was ready for more. I was afraid she was going to whip out a penis, so I trepidaciously said, "Okay?"

Trixie put another finger in the condom. What I thought couldn't get better, got much better. She kept hitting that prostate, as well as stretching my hole. I was in heaven. I told her I was getting close to a big orgasm.

She had me flip over and lay on a pillow then put a condom on. She slid her finger back in, and began to suck me. When I came, I was pretty sure my brain melted, I'd never felt like that before. I actually passed out for a few seconds. It was the greatest orgasm I've ever had up to that point.

After Trixie woke me up, I was so embarrassed that I couldn't talk. I mean, she must have thought I was gay—I couldn't get it up for smoking hot blonde stripper with huge jugs, and I let her fuck me in the ass?

She must have sensed my inner torture, because she hugged me. Trixie thanked me for letting her to finger my ass. That broke my silence. "Thank me? You just gave me a gay orgasm, and you're thanking me?"

Trixie looked at me angrily and stated, "Hey, I have some very good gay friends. Don't insult them."

She then smiled, and continued, "What happens between a man & a woman sexually isn't gay if it feels good, and that felt good for you, right?" I hesitantly agreed.

She explained she had been taking night classes in nursing, which is where she learned about the prostate. Trixie had loved trying it out on me, so much so that she was masturbating while she did me. She said she came twice, and that she'd never come from a client before.

She begged me to come back, and offered me a discount to do so, as she was only going to be around for a few days. I went back, and, well... I guess that's another story!

*

Special thanks to my editor nancyallen

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4 Comments
AnonymousAnonymousalmost 13 years ago
A sensual treat

It/s good to read a story on this topic that focuses on the sheer erotic pleasure of rectal/prostate maassage performed on a man by a woman without dragging in domination or feminization tyhemes. Those things may work for some guys, but they're really extraneous. Rectal massage can be sheer sensual heaven,leading to an orgasm like no other.

BarbaraBarbaraalmost 13 years ago
Most men enjoy Anal stimulation greatly, asking for more length next time, as they recover by voting on erotica like this suspect one!

Gay Sex? Most mature guys don't care what anyone thinks, as long as they still ejaculate, afterward, whilst being milked of all their testosterone by an agile youthful totally naked fully shaved and well-hung young stud with his penis both painfully and erotically inserted into his elderly rectum, whilst older men writhe hopelessly bound to his bed post by silver chains around the man's blue coloured testicles! As a BDSM clothed 'Mistress' I normally oversee elderly subjects to ensure his erection capable of verile activity with NMCF ladies, largely for female entertainment on any given day! So maybe I'm cruel at times, yet no complaints from my dear eighty year old former 'Master' once he is milked by a lady afficianado of CFNM within my group the following day! Now I enjoy Geriatric sex more than ever, at Ninety years old! Now who mentioned Gay sex? Perhaps you want to E/Mail me, after reading my true but unusual stories regarding my sex life?

rsqman68rsqman68almost 13 years ago
Great story!!

Oh Hell Yes!!! Prostrate massages from a talented lady absolutely RULE.

peebudypeebudyalmost 13 years ago
exit only!

nothing like having your ass penetrated and your prostate stimulated during sex! that's not gay, that's heaven!

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