I’m not quite a “bear” of a man but I’m 5’10 and 200lbs with an average enough dick. So, I’m not tiny. But she was. 5’3 on a “good day,” as she says.

A waist that can be wrapped around twice over with a tailor’s measuring tape and still have some slack to spare. But tits and ass that were perfect. Shapely, plump, soft, and very, very comfortable to rest on. If not for nothing, she was a perfect compliment to my frame. And that’s why i enjoyed being dominant for years. It just made sense. Me having my way with her. Two pieces of a puzzle that fit ideally. Why question it? Neither of us did.

Until one day, she decided to switch it up. I’m a curious man, I like to experiment, so why not?

There I sat naked in her bed after round #3 of furious love making when she said “I want to try something.”

“Oh? Tell me babe.”

“I want to eat your ass. I want to fuck it with my dildo. And I want to handcuff you.”

My initial reaction was literally, “LOL, WTF?!” But I couldn’t deny my girl, you all know that. So that’s why the experimental part of my brain kicked in, and I relented.

“Sure. This doesn’t have anything to do with that prostate orgasm we were talking about earlier right?“ She smirked. I knew the answer. She was reading some article her friend later about how the male orgasm isn’t in the penis, but in the prostate. She linked it to me earlier, but I just quickly glanced at it, not giving it a second thought. Perhaps, I should have…

As I was pondering, she got up, made sure to thoroughly clean her dildo, and asked if I was “prepped“ down there. Since I’m usually the one eating and fucking her ass, I had no idea what this meant. She shook her head, and told me what the “prep” process entailed. Luckily, all I need to do is wash up. And within a few minutes, I was back in her bed.

I cuffed myself, because I wanted an easy way out in case things got too intense. And then there I sat, in the candlelit hues of her big city apartment, bent over on my knees with my ass up as I’ve seen hundreds of porn stars do before. As if on cue, she started dripping some cold liquid down my ass crack once I indicated I was ready. The sensation was jarring, and I winced.

“Just some lube babe!”

uh-huh. What the fuck did I het myself into?

But I’ll be honest. As much as I seemed apprehensive, my warm skin was cooled by the gelatinous material. It felt very pleasant, almost soothing… And when she started fingering my asshole and slowly slipped her thumb in, my eyes start it open like that famous Lisa Ann gif. But instead of the pleasure, I felt pain.

“Ow..OW!!” She immediately stopped. I explained to her that she was poking me straight ahead. I needed her to push her finger towards my belly button, almost like an enema. At the time I was in the second year of my medical school, so I put that training to use. Hilariously, except instead of a digital rectal exam, I was instructing somebody on how to give me a rectal orgasm.

“Oh, I’m so sorry babe. I’ll do it better.”

And do it better she did. Over the next 10 minutes, she was sucking my asshole, massaging my balls and my taint, and being such a good fucking girl. I can’t believe how my ass opened up to her. And doubly so, I couldn’t believe how much I was enjoying it. I loved giving up myself to her. For once, I let up control, and followed her lead. It felt magical letting somebody else dictate my pleasure, instead of… Taking somebody else’s? If that makes sense?

Eventually she found her dildo and started slowly easing it in. By the time the bulbous head pushed through my asshole, I forgotten how it was already a little bit loose. Yes, it was my first time getting fucked like this, but she was doing such a good job that it felt so natural. She kept driving it in and out, like a piston. Starting out slow, and eventually picking up the frequency, as well as the depth. I felt parts of my ass starting to almost “pop“, and I was starting to worry. I was hoping she wasnt going to give me a fistula of some sort, or perforate my colon in any way.

And then suddenly, as I was lost in the pre-diagnostic stage of what could potentially go wrong, I felt something leak out of my dick. It wasn’t piss, but it wasn’t cum. It was almost as if my body jettisoned some air through my urethra, making sure that the tunnel was working. And all of a sudden, I clenched up and my hamstrings started to cramp, and I felt warmth over my taint. And my legs, they start to shake uncontrollably, but I felt… Pleasure. Not pain, not a cramp, but pure bliss. I gripped the bedsheet through the handcuffs tightly. And I just started moaning out loud and gyrating back-and-forth. And, she took a step back and watched me do all this. Losing her self in my own pleasure.

“Yes baby… Yes… Fuck yes!“

She echoed the my swears in my mind as she saw me, uncontrollably pulsing, having a conniption from my cock over this orgasm. Watching a man like me shake like that from the power a tiny girl inflicted over me must’ve been a sight. And I just collapse in a heap. Still gyrating into the bedsheets because it just felt natural again, but very much exhausted after what I think was my first ever prostate orgasm.

She then crept over to my ass and started licking my asshole again, like a cat licking paws after a meal. As I flipped over and she put my cock in her mouth and sucked off whatever cum was left on my foreskin. She was beautiful, and this moment was beautiful. I’ll never forget it. I copped her cheek and brought her face to mine, and tasted myself off… Spent the next hour loving her tenderly.

It’s been years since this happened but we know how I felt that night. And she does too. She knows every time I look at her when we talk on the phone that my lust for her permeates thru the screen. Because when a woman makes you feel things like she did to me that night, she isnt somebody that’s easily replaced. Trust me, my ass and prostate can vouch for that.