Tag: Prostate

[FM] Meeting McDaddy, A Story of Unexpected Connection and First Date Anal

In early July of last year, I’d made a commitment I wanted to make good on, and then get off my plate.

For weeks I’d been casually chatting with a suburban Ohio dad I’d met via the r/affairs subreddit. At the time I replied to his ad, he was married living at home. By the time we were scheduled to actually meet, he was separated, living in an extended stay hotel experiencing FOMO watching the migrant guests partying in the parking lot each night.

As a person in a relatively stable open marriage, the separation/divorce thing made me uneasy from the start. Men in this situation have a reputation of being the opposite of stable.

But this guy seemed nice and a little bit funny too. And so in June I casually mentioned meeting up for a drink the next time I was in his city for work. From that point on, he was pretty much a digital Stage 5 clinger.

So on a hot, humid Monday night in July it finally happened. Going into it, I thought to myself “this is strictly a courtesy drink and then right back to my air conditioned hotel room for shut eye.” Read more »

Discovering My Love of Pegging [M29/F29] [Married] [Pegging] [Anal] [DP] [Toys]

I never thought much of anal sex for the longest time, in any form. I’m a cis-male who was generally always into your standard, run of the mill porn. Heterosexual, lesbian at times, some other different fetishes but nothing ever involving anal and definitely not pegging.

I didn’t even really know it was a thing until I watched a video of my favorite pornstar at the time where she was pegging a guy. The description of the video had nothing to do with pegging and the thumbnail images never showed it either, but it made up a good portion of the video. Anyways, it was Remy Lacroix pegging a guy with a pink strap-on dildo (a bit of a deep cut for you porn fanatics).

When it first started showing the pegging scenes, I was obviously confused. But I found that as I was watching, I never lost my erection and was actually sort of turned on by it. Remy taking control of the situation and fucking the guy in the ass was super hot to watch, and it made me question for a brief moment what I really wanted to see. The rest of the video was back to standard stuff (at least as far as I remember), so I kind of forgot about it for a few years. Read more »

Judgement part 2 [F-M] [femdom] [medical] [prostate play] [dildos] [full-body restraints] [orgasm denial] brief mention of [breathplay]

Read part one [here](https://www.reddit.com/r/Erotica/comments/10ukgcy/judgement_fm_femdom_medical_prostate_play/)

Kathy reached into the cabinet and pulled out several large, phallic objects. I stifled a gasp. She was going to put those… inside me?

“These start at six inches and reach nine inches,” she said with a devilish grin. “I would try to stay relaxed but, let’s be real, this will hurt a little either way…” Kathy began lubing up the smallest dildo as my ass began to quiver in anticipation. I was never like other boys but this was…

“Alright here it comes!” Before I could finish my thought, Kathy plunged the dildo deep into my waiting hole. I gasped. It hurt but… I felt a deep sensation cutting through the pain.

“H- hard- harder!” I couldn’t believe how something that hurt so bad could feel so good! As she worked the dildo in and out, hitting my prostate faster and faster, I began to lose control of my moans.

“Oh, are you close to cumming again sweetie?” She said with a playful tone. “Well get used to the feeling!” Kathy suddenly yanked the dildo from my ass, leaving me near tears.

“Please Kath-” Read more »

Judgement [F-M] [femdom] [medical] [prostate play] [fingering] [full-body restraints] [orgasm denial]

I walked through the doors of the Male Health Clinic on my eighteenth birthday with a mixture of fear and anticipation. Today was the day every male knew he would be judged, measured, and given his place in society. A smiling female doctor led me to a waiting room, where she gave me my last few moments of privacy before the main event.

“Nervous?” She asked, walking into the room again. “It’s normal for boys to feel discomfort before the judging. Just know you’re in capable hands here at the clinic!” Her toothy grin did nothing to ease my nerves.

“I’m just worried I may not like the outcome…” At my words, her grin changed to a pitying frown.

“Aw poor boy. It’ll be okay no matter what happens in there. The Male Classification Act was put in place to protect you boys from trying to fit into a role you were never going to be able to fill. Our judges are fair and just. You’ll grow into whatever they decide you should become!” For just a second, I could swear her grin became a smirk. I had heard it all before, but minutes before the actual judging, I couldn’t help but shake. Read more »

[MF] I had this woman that was an orgasm machine. No matter what I did she enjoyed it.

I’ve been with a few women, not that many, but most of them have had particular things they needed to get off and I would always oblige them obviously, but it definitely made me realize that intercourse alone would not get most women to orgasm. No big deal though, still had good sex, but I had this naive thought that this is just how things work, women don’t orgasm from penetration. In addition, I‘m slightly above average in size and sometimes with some women it was just uncomfortable for them in certain positions, so intercourse was kinda getting a bad rap in my mind. This did make me much more aware of everything around intercourse and once I got the hang of all that everything was cool, but for a long while after I first started having sex I hadn’t really met a woman that had orgasms from intercourse and I was starting to think they didn’t exist. Read more »

Sail Away [M19/F19/NB19] [Bi] [Oral] [Anal] [Threesome] [Work in progress]

The gray skies were starting to clear as Billy expertly piloted the boat to rest alongside the dock. Cutting the engine, he quickly tossed lines to Toby and Ali. They pulled the boat in against the dock and tied it to the waiting cleats. The bumpers Billy had put out squeaked as the low waves in the harbor gently lifted and lowered the sailboat, their home for the next week, up and down. His parents had graciously offered to let them borrow it for the trip, a vacation for the group of the childhood friends, reuniting after another year away at different colleges.

Ali and Toby had arrived on the island on the same ferry the day before. They met up at the terminal and spent the whole crossing talking non stop about what we’d been up to for the past year and their upcoming adventure. The conversation was just starting to slow when the ferry docked and they disembarked, walking off with their bags and scanning the waiting crowd for Billy. He waved them down and greeted them warmly then led them to the car. On the way to his parent’s vacation house they stopped in the little town to get dinner and supplies, Billy leading them to all the best shops and avoiding the tourist traps. Ali and Toby followed along, remembering some of them from previous visits. Read more »

Another Play Night Pt. 4 of 5 [M/F] [20s-40s] [GFE] [Fdom] [Msub] [Bondage] [Paddle?] [Pegging] [Denial]

[Continued From](https://www.reddit.com/r/eroticliterature/comments/10n2wd4/another_play_night_pt_3_of_5_mf_20s40s_gfe_fdom/)

Another Play Night Part 4 of 5: It’s a Hard Lesson to Learn (She Sure Has You Pegged)

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I was about to apologize again when she began to speak in that I’m-not-angry-just-disappointed voice. “I even put my titty in your mouth, and at the first sign of push back, you pulled away. Did I use the safe word? Did you yellow light and ask what the deal was? I really thought we were making progress…”

At this point I would honestly rather go back to the slapping. At least then I had something to distract from the turmoil of doubt and guilt brewing inside. She wasn’t happy and it was, of course, my fault. Just like when I accidentally found the stethoscope, it seemed I’d developed a penchant for ruining things.

The ashamed look on my face only seemed to make her irritation worse. “Nothing else to be done for it, then. I’ll just have to lead by example. Go fetch the footstool while I get things ready. You know the one.” she ordered. Read more »

Fun in a MFF threesome (real)

I’ve (F) had fun with my female friend, and we have both had our own fun with her male friend she introduced me to. So naturally we wanted to all have fun together. Our schedules finally aligned!

To start with, she and I made out a lot and started to play before he got there so we were ready to go. He came in, stripped, and joined right in. We sucked him off together for a while, both taking turns on his cock and then her sucking him while I sucked his smooth balls and licked his shaft. He was loving it as he held both our hair back hard, away from our face, pushing us towards his coco. She pressed a toy against his ass (he’s into prostate play) while I scratched my nails down his legs, grabbing each others’ arms and hands as he moaned out in pleasure.

Eventually he told her to fuck me, so she did with her strap-on while using a vibrator against my clit, while I sucked him. I came SO hard and she kept going till I came again and basically just collapsed. Then she laid in front of me on all 4’s, bent down sucking him while I fucked her with two fingers and rubbed her clit. She came incredibly hard all over my hand while he lightly choked her and kissed her neck. Repeat and she got off again, really hard. Read more »

My Yearly Checkup [M44/F33] [Femdom] [Anal]

Some time ago it was time. The time of of the year. Time to something I never was looking forward too: My yearly physical. Once a year I head over to my doctors office to give myself a proper checkup. To see if my body is still up and running. And to please my insurance.

The last years checkup was the last one with my old doctor. He was an awesome physician, he had humor, we got along with each other when we were dealing with each other. But on our last get together, I was visiting his office for a few stitches, to close op a cut, he told me that he had enough of the daily grind. He loved his job, but he was retiring.

It didn’t really took me by surprise, because he wasn’t the youngest anymore, but it still bothered me. Because finding a good doctor, it is a tough thing to do. But after he told me that he’d retire, he also told me that his daughter would take over his office. And that I might give her a try. I followed my doctor’s advice. Read more »

EARLY MORNING THROAT FUCK [mf] [puke] [facial] [piss]

I woke up late and when I went downstairs, my boyfriend was making coffee and reading over something on his phone.

“You aren’t gonna believe this,” he said. “The meeting I’ve been planning for all week just got rescheduled to TODAY at 4pm.”

“Shit,” I said as I opened the fridge and started chugging crystal clear Gatorade.

His eyes narrowed as he eyed me. The Gatorade was there for one thing and one thing only. Watery puke blowjobs.

“I guess you’re pretty angry,” I said as I wiped the Gatorade from my chin.

“You could say that …”

“Pretty stressed out, too?” I asked.

He nodded.

I looked down and could see his cock get hard before my very eyes. Within literal seconds there was a nice large bulge in his boxer briefs. I gulped with anticipation.

“You know,” he said as he faced me. “I haven’t blown a load in like … three days. Maybe four?”

“Oh yeah?” I asked as I lowered myself to my knees.

“Yeah. Weirdly preoccupied with work and this damn meeting.” Read more »