Hooking up with my boss’s Mom. [MF]

I checked out this sub-Reddit a few weeks ago after hearing about it from a friend and have enjoyed the stories so much that I was inspired to share something that I’ve kept under lock and key for over a decade, circa 2011. I have not told a soul, not even my wife.

Let me start with the setting and backstory, then I will share everything else (****), down to the granular details, as memory serves best. It’s a bit long, but it gives context to the event. All the names used in this story are changed to prevent someone from being recognized.

By the end of summer of my Senior year, at a state college in south Texas, I was dealing with the heart break of being dumped by my girlfriend of two years. It happened over Skype a few days after I helped her move to Austin, to attend a more “prestigious” university. I was quite smitten with her and in total denial that the relationship would end after she decided to transfer. I thought she was THE ONE, but life had different plans. I’m sure some of you can empathize.

At the time of this story, I was working as a waiter at a family owned TexMex restaurant and was halfway through my two weeks notice. During these days, shit was hitting the fan at work. There were rumors that the owner’s dad Pablo, who was the financier for the shop, had been getting a little too flirty with the hostesses. To make things worse, a few months before, a server told the owner’s wife that her husband Dylan was having an affair with a cougar that would periodically visit the joint during Happy Hours. For those of you that have never worked at a restaurant, when something happens, the news spreads like fire on gasoline.

As I write this, the memories of the day in question are all flooding back, here is my account as I best can remember…

So there I was, on a Saturday afternoon, clocking out after working lunch hours when my manager asks me completely out of the blue to run an errand for Dylan. In the days before, a landscaping company had redesigned the front of the place and I was asked to take the few left-over bags of sand and pebbles to my boss’s house. It was kind of on the way back to my apartment so no biggie. I didn’t know it yet, but it was my LUCKY day.

Let me tell you that house was beautiful, not a mansion but pretty damn close. Alma, Dylan’s mom, answered the door and asked me to leave the bags in front of the garden. She was attractive for an older lady, a light skin woman of probably mixed European background and Mexican heritage. She stood about 5 foot 8 inches or so, she had a strong, beautiful face and a mature woman’s body with amazing legs, those caught my attention immediately. Probably between 60 and 70 years of age at the time. She offered me some water, and I went in the house. At some point I made my way to a small table with some photos. There were a bunch of old family photos, but one that caught my eye was of Alma. She was a stunner in her youth. It was a photo of her in a sundress, with long brown hair, smiling in front of a small brick house. I think I must have stared a little too long because Alma surprised me as she walked to my side with the water.

I told her she had a beautiful family and we talked briefly about some of the places in the photos. At some point I brought up her photo and told her how beautiful she looked in the photo. She didn’t say anything back, just smiled and gently brushed my arm. Now I don’t know what got into me, but I turned right at her and told her “you still are a very beautiful” in a blunt manner and checked her out from head to toe. This I remember crystal clear.

After a few months of being in a funk, lonely, low in confidence and no motivation what so ever to get laid, I was picking this moment to hit on someone…I guess that small amount of contact is all it took to wake me up. The mind is a weird place. Up to that point in my life, I had never really gone for cougars or the milf types. Yes I found some older women attractive, but my attention had always been on girls my age. As best as I can recall my emotions of that particular time, I must have thought I was standing in front of a goddess. I guess it was all in her dark brown eyes AND those amazing long legs.

She must have read the moment well, to diffuse my horn dog mood Alma asked me to sit with her. We moved over to the living room and sat on a sofa as I sipped on my drink. We conversed about my plans after the restaurant, but in my mind I wanted her. I took a chance, scooted over next to her and placed my hand on hers as I told her how attracted I was to her and that I wanted to fuck her. In those exact words.

For a brief moment she just starred right back at me, she was shocked I’m sure, I was being very forward and perhaps it had been a long time since someone told her that. Alma slowly got up, walked away down a hallway and opened a door. As she entered she looked back at me and then disappeared from my sight. In that moment I can tell you in all honesty that I thought she was either going to call Pablo, Dylan, or even the police. Time was moving at a snail’s pace and I started to panic a little and the thought crossed my mind that I should just slip out the front. I was frozen to the couch. Maybe 2 to 5 minutes had passed. As I had decided to dip out, I see Alma take a few steps out of the room in the green blouse she was wearing earlier and her panties. That was it. She locked into my eyes for like 5 seconds and then walked back in…

**************

At 21, I was somewhere between a skinny and athletic build, I frequented the gym, but was not at all jacked. Actually, the main focus was my core. I had a solid 6-pack (recently traded in for a keg) and high endurance for physical activity. I am about 5 foot 9 inches, mixed race – hispanic & white – and fairly good looking. That version of me must have floated into that room, because I don’t remember walking in there. I do recall now as if it were yesterday, Alma was standing next to the bed in what must have been a guest room, with this look I did not quite comprehend at the time.
At my current age and experience, I would recognize that look, she was THIRSTY, but my 21 year old self just gravitated to her without a second thought.

I made the first move and kissed her, but she stopped me, guided me to the bed and we began to undress each other. She began unbuttoning my shirt and unbuckled my pants, I unbuttoned her blouse and let it fall to the floor. Once I was in my boxers she began caressing my erection. She pulled it out through the front slit and began slowly masturbating me. We were still sitting on the edge of the bed when I began kissing her shoulder, then her neckline, around her ear and then her mouth. I have always been big on foreplay. At some point I began rubbing her clit over the panties and eventually slipped my hand inside. I remember her declining my request to eat her out, but we eventually laid down, removed all remanence of clothing, and continued fondling each other until I moved on top. She grabbed my ass and pulled my torso in as she opened her legs.

At the time, my MO in bed was to restrain from cumming as along as possible. I tightened my groin or pulled out at the first sensation to ejaculate, which at the time helped me last a lot longer during the first fuck. I know this sounds weird, but that’s how I did it back then, and I was in considerably better shape than as I write this (I’m more of a sprinter now, don’t judge).

With Alma, I was in total control. Missionary is how I’ve always done my best work, and I labored for her. Some of you may know the feeling of being in flow or in the zone, and in that moment Alma and I were there together. I would move her legs into my favorite positions; both legs upright and close, knees bent and over her stomach, one leg on my shoulder, classic missionary, and both legs up and wide apart. At some point I hit a sweet spot. With one leg over my shoulder and the other wrapped around me, I clamped my hands around her ribs and felt an incredible sensation as I thrust into her dripping vagina.

The sweet spot I found had me in a spell and I began a more rapid pace and violent thrust. I have no idea how much time had passed, but I know she had cum her fair share and I was ready to give in. Alma was breathing heavily at this point, both hands gripping the sheets at her side, with her eyes closed and teeth gritted. The unmistakable sound of pounding wet pussy had me motivated to go all out until the end. As the warm sensation of the release began forming, all I said was “I’m going to cum”. Alma replied, “cum inside”. That was all 21 year old me needed to hear.

At that point I had never cum unprotected in another woman. Sometimes with a condom on, but mostly with a condom and pulling out with my girlfriend stroking me to ejaculation. Take no chances, right?

I shot ropes deep into that abuela’s pussy. We both let out some moans, nothing crazy or overtly load, but we came together. Her legs shook as I pushed as deep as possible. I was so turned on I just kept on humping and feeling out my sensitive cock in her. After a few minutes, I went limp and we just laid next to each other, staring at the ceiling, breathing like we’d just ran a marathon.

I remember getting up, walking over to the guest bathroom to relieve myself, looking down and seeing my dick crusted in her fluids. Alma had just gotten a proper fucking. When I walked back, I shared my water with her and laid back down, I turned over to her and began kissing her shoulder and neck again. It was an intimate moment. I remember Alma turned and smiled at me, she was drenched in sweat. We chilled for a few minutes before I got hard again.

I have a less vivid memory of the second time, but I can recall her cursing a few times as I pounded her, and within give or take 20 minutes she tapped out. I guess her mature pussy didn’t have another pounding left in it, and there was no lube, so that was it. We laid next to each other for a short while, she may have even apologized for stopping. Looking back now, maybe I should have asked her to give me head, but as odd as it may sound, I felt it may have been disrespectful. By the time I walked out dusk was settling in and I was on my way home.

For the rest of my time at the restaurant, I was a nervous wreck. I didn’t want to deal with the blowback of someone (which in turn meant everyone) finding out I fucked the owner’s mom. My last day at the restaurant I’ll never forget. As I was saying my goodbyes I ran into the hostess that I mentioned previously. She inquired if I had heard the rumor. For a second I thought she meant about Alma and I, but it was about her issue with Pablo. She mentioned that she had come in to quit and she was thinking about pressing charges…well there’s that I thought. After a few more words I walked away and found myself making eye contact with Alma. I was surprised to see her, apparently the family was having dinner at the restaurant that night. We met each other at the bar, she gave me a warm embrace and told me “we are going to miss you here at the restaurant.” I told her I would stop bye to check up on them sometime. I never did visit the restaurant again. She was glowing that last day I saw her, I think she just needed a good release from the stress of the rumors running around the place.

As I approached the front door, the owner’s wife was walking in with her kids on each arm. I opened the door for her, we made eye contact, I sent her a smile which she did not return. Shamelessly I checked her out and she looked away as they walked by. I wonder if Alma told her something. I just let the door close and walked away.

I kept this event out of my mind for so long, now there are some reflections I’d like to share with you all.

First, the encounter with Alma at Dylan’s house might have taken around 2 hours overall, but not once did I think to check with her if someone else was at the house or due to arrive. She obviously knew we were in the clear, I’m sure, but it goes to show how careless the 21 year old horn dog version of me could be.

Second, as we were getting dressed, I remember that Alma never went to the restroom. She put her panties on and got dressed before we parted ways. I wonder if she walked around the rest of the day with my cum in her pussy?

Source: reddit.com/r/gonewildstories/comments/td9xob/hooking_up_with_my_bosss_mom_mf