Author: jackmac415

[MF] Catching My Professor in the Act

I can easily say that my attraction to confident, intelligent and self-empowered older women traces back to a single moment when I was in still in school, studying as an undergrad at NeverTelling University.

I was 21 and feeling fresh and confident back from a semester studying abroad and “finding myself” in South America. In retrospect it’s honestly cringe inducing to think about the time I spent trying to impress all the underclassmen with my expanded world view and Not-fake ID.

Professor Robinson was in the Gender Studies department and up until that semester, had barely crossed paths with her, but I knew her by reputation as one of the best and most sought after teachers in that department. Her classes filled up quick, but I was able to grab a spot in one due to its cross-over with my Film minor.

She lived up to the hype and more. She was one of those teachers that no matter your interest in the subject, her command of both the classroom and the material made each class electrifying. She made the space open for free discussion but was able to challenge opinions and assumptions in the way that actually helped shape positive growth. Read more »

[MF] Giggles and Fucks in the Great Outdoors

Just got back from a nice little weekend in the national forest.

A group of 6 of us paddled out to a nice secluded spot on the far end of a lake in the middle of the Colorado wilderness and just posted up for the long weekend; fishing, hiking, building campfires and just general debauchery.

Jesse was the only other single person in the group. She was a 28 year old cousin of my friend who was in town visiting from the west coast for a couple of weeks. My first reaction was: “damn, Terry’s cousin is pretty fucking cute.” My reaction after singlehandedly paddling us across the lake while she exclaimed at the scenery and took photos was: “damn, Terry’s cousin is pretty fucking annoying.”

After literally pulling both of our weight the entire first day, I was pretty cold to Jesse on Friday night. But after I had some food, I remembered that she doesn’t do stuff like this ever and maybe I was being a bit hard on her. And all Saturday, I was more patient and instructive when helping her through some of the camping basics like how to filter your water, find good firewood and how to get into a canoe without immediately flipping us into the lake. By Saturday night, we’d become fast friends. Read more »

[MF] Alice’s Bunny Ear Toy (A Part 2… Kinda)

I posted earlier about my first sexual experience with Alice, the attractive widow whom I had accidentally walked in on while masturbating while at her house to walk her dog. A few people requested “updates” and though this all happened a few years ago and there is not much to actually update, I thought you all might appreciate hearing about another steamy time that we spent together.

Since that day when she had invited me into her bedroom to witness her shaking orgasm and cum on her chest, we had hooked up a couple more times. Her schedule was so erratic that usually I walked up to her front door with no idea what to expect. Sometimes I’d find a completely empty house, sometimes she’d be briskly pacing around the living room on a business call, and sometimes she’d greet me enthusiastically at the door in a tank top with no bra and tight jean-shorts and we’d fuck before I took Barkley out on his daily walk.

She was too busy with work and her kids for a real relationship, and I soon found that I was her only real outlet for quenching the thirst that built between her legs that comes from being human. Read more »

[MF] Caught my Dog-Walking Client Masturbating

Back when I was 27, I worked as a dog walker to make ends meet. I had a lot of wealthy clients with more money then they knew what to do with, so they usually spent it on being lazy. The best paying clients were always the ones that like having a dog, but didn’t like doing any of the work required to keep them happy.

Alice was different. She was 42 year old single mom, who entirely supported the family after her husband had died from illness when her son was still an infant. She made good money, but was entirely too busy to spend time exercising the puppy, Barkley, that her 14 year old son had “promised he’d take care of”. She was a good looking woman with a warm smile and a body kept in shape as much from the chaos of her work as much from the regular exercise classes that she refused to skip. Read more »

[MF] Receiving End of A Revenge Blow-Job

Emily was pissed off.

In the three years that we had worked together, I had never seen her in this state. I had seen her stressed, frustrated and annoyed. But nothing like this, positively trembling with anger and scanning the restaurant as if she was assessing which of the objects nearest her would be most satisfying to destroy.

We were traveling together on a business trip to meet with a few potential clients in a neighboring state. The trip, so far, had gone mostly without incident; us both managing to secure a handful of new commitments before meeting up to recap the day over a pleasant meal at the hotel restaurant. Then a text came in to her phone and I saw her expression change from joy, to confusion, and then to pure fury.

When I started at the company, I had been immediately attracted to Emily with her sleek brunette hair, dark eyes and runner’s body. But I had shortly learned about her long-standing boyfriend and – though I still nursed a slight crush – I had never tried to bring our relationship beyond a middle-ground between professional kindness and platonic friendship. Read more »

My Favorite Annual Tradition Cums in June [MM]

*Disclaimer: everyone is over 18 in this post*

It’s my one of my favorite times of year. The days are getting longer and warmer, the rivers are running and Lucas comes to town.

I met Lucas 6 or so years ago when craigstlist personals were still a thing. He had posted an ad looking for a “Slight Young Man for Free Erotic Massage”.

The post detailed that he was a (mostly) straight married man who was vacationing at a family house in the area, looking for a younger discreet guy to give a free sensual massage with no reciprocation necessary, but appreciated. I was hard immediately.

As an in-the-closet bi guy in a small town with little outlet for my gay side, it seemed like the perfect arrangement to satisfy some urges long neglected.

He replied mere minutes after I had sent my age and stats and a little about my strong fetish for “normal” massages that turn erotic with older men. We exchanged a couple messages and photos and eventually had a time and place set and a beautiful yearly tradition was borne. Read more »

[MM] Throat-fucked in the Campground Restrooms

Just got back home from a two week long road trip. A little spring adventure to get some fresh air and enjoy some solo time. For the majority of the time, I really focused on myself tried to keep it in my pants while I took the opportunity to reconnect with nature. But last night, the horniness took over and I broke down.

I never got his name, but his cum is likely still settling somewhere inside me.

I – a 33 year old slim redhead – was spending the night in a group campground, laying on the makeshift bed in my car and scrolling reddit, when I passed a NSFW post that gave my cock a little twitch. And then another, and then another. Soon, I was rock hard and slowing stroking.

Sometimes when I am really in the mood, I’ll just hop over to Grindr and scroll through the “options” imagining what it’d be like to be with each one. It can work better for me than porn, something about being actually within grasp makes the fantasy hotter. Read more »

So… I Fucked My Dad’s Friend This Weekend… Again [MM]

It’s hard to top getting teased and pushed to the edge and then finally climaxing to knee-shuddering completion while watching a live feed of yourself get pumped with cum by a hot older gentleman. Or at least that was what I was thinking as I sprawled out – naked from the waist down – on the deep-set plush wrap around couch in the dimly lit home theater of Henry’s vacation rental. I was absent-mindedly playing with my still-sensitive cock and tugging slightly at my recently-drained balls as I thought about the events in the night that had a led to this feeling of pure satisfaction and relaxation.

I had been at a fancy cocktail party feeling completely out of place and was just on the cusp of bailing with the one person there I knew, when Henry had stepped out of the crowd. He was an old friend and co-worker of my dad’s whom I had jerked off thinking about during my early years of discovering my bi-sexuality. At the time, he was one of the only gay men I knew that completely fit my favorite ‘type’. (My first introduction to that side of me had come at the hands of a ‘daddy’ and even to this day, I harbor a special weakness for confident, experienced older gentleman.) Read more »

So… I Fucked My Dad’s Friend This Weekend. [MM]

*So this happened two nights ago and I attempted to do a short ‘update’ on what happens at the end, because it was new and exciting to me. But, in trying to properly set the stage and circumstance, I wound up taking nearly a day and half and writing way more than I intended, so hope you all enjoy!*

Last night I was at one of those parties where at some point you look around and think to yourself: “why the fuck am I here?”. I had been invited by a co-worker of mine (f) whose wealthy family was putting it on. She had been dreading going because she never gets on with her parent’s friends and wanted someone she could talk to. I didn’t really have anything else going so I thought at the very least it’d be free food and drinks and maybe even a chance at getting a fire lit between me and her (I have always fostered a bit of attraction for her). But 1 hour into the night – though me and her had been getting along nicely – we both quickly realized that were essentially set dressing to these other “higher end” guests. Read more »

[MM] Meeting Primal Needs with a Stranger

This happened yesterday and I am still buzzing with lust thinking about it. So instead of fighting it or quickly releasing with a quick wank, I’d thought I’d just lean into it and prolong the final satisfaction by reliving it with you fine people. Hope you enjoy!

In what I am sure is a relatable situation, I was sitting at work on a sunny spring Friday afternoon, and I just completely lost interest in everything I had been engaged with. My thoughts had been drifting for hours and I could only focus on two things: spending some time outside in the blossoming spring weather, and fulfilling the deepening horniness that had building inside me all week (months really). It had been a long time since I had had a random hook-up and I was finally two weeks post-vaccination and wanted to celebrate my restraint. 

I clicked off my computer and leaned back in my office chair, grabbing my phone from the desk and opening up Grindr. Scrolling through the prospects, I could feel the hard-on building in my pants, thoughts of what I wanted to do with each filting through my brain as I sent out my feelers.  Read more »