Fooling around with [M]y Mom’s [F]ormer Boss Part 1

I think I was 22 or 23 when my mom switched jobs but stayed really good friends with her now former boss Alex. She was a corporate type A woman married to a slightly less successful man (I’ll call him Bruce) who had a bit of a Napoleon complex. She was a petite brunette in her mid 40s, probably 5’3 or 5’4 with almost no tits but a toned little body I made no secret of checking out when I saw the opportunity. You could tell she had always been pretty but wore conservative style clothes to be taken seriously at work. Bruce was only a couple inches taller than his wife and made up for his stature by being a complete asshole whenever it suited him. The type of douche who rode a $5000 bike for exercise and wore absolutely every piece of equipment you could buy. Anyway, if you couldn’t tell, I disliked every single thing about him even before he got caught cheating with a girl my age and moved out of their beautiful house to be with the sugar baby obviously looking to take his money.

Our whole family was a bit surprised when Alex was devastated only because she had always seemed to sort of barely tolerate him like the rest of us. Now I guess I should mention she had always teased Bruce and my mom by flirting with me in front of them. She would make comments about my height or deep voice, on more than one occasion saying something like “What a lucky girl Kate is!” in reference to my girlfriend. I always just laughed it off as more about the awkward reaction she enjoyed getting from them rather than actually finding me attractive.

I remember it was a really nice day out when she called my mom and asked if I could come over to help with a house project she was sure Bruce had screwed up before he left (I’m in the trades). My mom knew I was always looking to make a little bit more money as I was still just an apprentice at this point so she agreed to send me over. They lived only about a two minute drive away but I took my beat up truck so I’d have all my tools incase it really was as bad as she thought.

When I got to the house I parked against the curb so I wouldn’t block her BMW in and climbed the five or six steps, knocking on the front door. She must have been either walking past or waiting at the door because she opened it almost immediately, “Hey sweetie, thanks for coming!” She stepped towards me and stretched to give me a hug with one arm, “I swear you get taller every time I see you!”

We went inside and she showed me what she wanted fixed and explained angrily the way in which she thought Bruce had probably screwed it up. She was so angry, not only about this one thing but it seemed like absolutely anything to do with him… you could tell it took everything she had not to scream every time she said his name.

“It’s not as bad as it looks but I’m glad I brought tools. I’ll just grab them from the truck, shouldn’t take more than an hour.”

“Really? Well I guess that’s how it goes when you know what you’re doing… I’ll grab you a beer. Want a sandwich too?” She asked standing behind me and putting a small hand on my shoulder as I crouched.

“Nah I’m okay for food, a beer sounds great though.”

“Are you sure? I’m making one for myself anyway? I don’t want you to tell your mom I didn’t feed you.”

I laughed and turned back looking up at her, happy to see her smile, “Actually I didn’t have breakfast.”

She skipped away to the kitchen while I went back to my truck and grabbed some gear but when I came back inside, walking past the kitchen, she had disappeared upstairs. I started working without thinking much of it and after about ten minutes I could hear her chopping something on a cutting board in the kitchen behind me over the sound of my drill. Hearing her walk into the living room I put the tools down and turned around to see her standing there in an incredibly small orange bikini with white polka dots. I couldn’t take my eyes off of her toned tan stomach and the low hem line of her bottoms.

“I’m going to sit out back and tan if you want to take a break?” She asked through a satisfied grin, clearly having had the effect on me she was hoping for.

I forced myself to look up into her eyes but couldn’t wipe the smile off my face, “Yeah, that sounds good.”

We sat outside on two patio loungers with the tray of food on a matching table between us, “know anything about hot tubs?” Alex asked glancing over at it to her left through her dark sunglasses.

“Not a thing, but I’m sure I wouldn’t hurt it to take a look? Hasn’t been working?”

“I don’t think I’ve turned it on in two years.” She laughed looking back at me and making a playful wincing face at me.

We ate and sipped bottles of Corona while she asked me about work and if I was still playing hockey. Eventually the conversation inevitably led to my girlfriend, “So why did you break up?” She asked having clearly already gotten information from my mom.

“Uhh… things were going okay but she’s definitely not that into me emotionally. I think her parents were pressuring her a lot to find someone in the corporate world. They can’t picture her with a guy like me and I think she was starting to feel the same way.”

Alex’s face became visibly annoyed, “Yeah because that always works out,” She reached across the table and put her small hand over my rough one, running a finger along one of my many small scratches, “Whatever you do, don’t settle, make sure she checks every single box and appreciates you.”

The conversation had gotten so serious so quickly I just smiled back and quietly replied, “I will.”

Fortunately the tension was broken by a neighbour from next door in one of those ridiculous rich lady hats, “Hi Alex! Beautiful day finally!”

“Sure is!” She replied having to turn all the way around to face the woman who must have been standing on her deck to see over the fence.

“Oh sorry, didn’t see you had a guest!” She called out raising her hand in a little wave.

“No problem, we were just having a little lunch,“ she squeezed my hand, “This is my new boyfriend Jay!”

I had to bite my bottom lip to keep from laughing when the woman stuttered a bit in response clearly being close enough to see my baby face, “ohhh… uhhh.. yeah… that’s so nice…. Nice to meet you Jay.”

“Nice to meet you too… probably be seeing a lot of each other.” I responded playing along. Alex turned back to me and mouthed “Oh my God!” While stifling at least the sound of her laugh as her shoulders shook a little.

“Well… time to uhhh…” Alex could barely get though the sentence as she was trying so hard not to burst out laughing at her neighbour’s expense, “time to get this stud back inside.”

She stood up and took me by the hand, we must have looked quite the pair, her in her tiny bikini and bare feet and me in my dirty jeans, chalky black tshirt and work boots.

“Oh my god that was amazing,” she laughed biting her lip as I closed the patio door behind me, “I really hope that gets back to him.”

I smiled back and laughed, the idea of that asshole ex husband of hers hearing about us sitting out on the patio having lunch together was good enough but if her neighbour had been convinced of our story that would be even better, “you think she bought it?” I asked standing in front of her.

“She would if she saw what happened next.” Alex responded while trying to put her short arms around my neck but not quite able to reach past putting her wrists on my shoulders at the same time standing on her tippy toes planting her soft lips on mine. She tasted like Corona and cherry chapstick. I was absolutely shocked thinking that we had just been messing around. I definitely hadn’t been expecting this but instinctively put my hands on her almost naked body. My big left hand was just above her ass while my right was just above the tie of her bikini top, using both to pull her into my body as we started to make out. I started walking towards her without ever breaking our kiss, pushing her back against the marble counter of the kitchen island. I put both hands on her waist and picked her up and set her down on it bringing our heights at least a little bit more in line. Her little hands quickly clenched the bottom of my shirt and she furiously lifted it over my arms and head, our kiss breaking.

“Fuck.” She almost growled as she used a finger to trace my young abs before running it along my treasure trail. I exhaled hard wanting to make sure she knew how good it felt to have her touch me.

I think it was at this moment she started to question what she was doing and whether any of this was a good idea. She put her hands on either side of my waist holding me by the belt as she took a deep breath and looked my upper torso over as if to save a mental image for later.

“We should probably stop.” She almost whispered as she looked up into my eyes giving me the sense that she wanted me to be the one to push things further.

“I don’t want to.” I replied lustfully, my voice about as deep as it gets. I leaned in and started to suck on her soft neck, her chin just over my shoulder.

“You really want me?” She asked through quick breathing wrapping her arms back around my much larger frame.

“So fucking bad it’s starting to hurt.” I growled into her neck as my throbbing cock strained my tight boxers and dirty jeans. I slid both of my hands under her perfect little ass and picked her up while she wrapped her legs around my waist. I carried her down the hallway and paused for a second at the stairs as she glanced behind her.

“Set me down.” She whispered kissing me on the cheek just next to my ear.

“No.” I replied carefully climbing the stairs with her wrapped around me while she let out a little concerned squeal. We passed the kids bedrooms and I turned and walked through the double doorway of the master bedroom, laying her down softly on her back at the foot of the bed.

“That was so fucking hot.” She groaned as I positioned myself over top of her and she pulled me into another sloppy kiss. With my arms still wrapped around her I pulled her bikini top string and used my mouth to pull the fabric off her chest, immediately sucking her tiny nipples one at a time. Even though her tits were A cups they matched her toned body perfectly and I loved the reaction sucking on them was producing out of her. She was writhing on the bed and grinding her barely covered pussy against my abs. Alex wasn’t wet, she was SOAKING. In my limited experiences at this point I had never known a woman to get so aroused and I found it intoxicating knowing I had helped do that to her.

“I wanna ride you.” She whispered pulling me tight to her body, her hard nipples against my own chest. I flipped her over in one motion so that her legs stayed on either side of me, my stomach glistening from her juices between us. She reached down and undid my belt before unzipping my fly. Scooting her ass down my thighs a little she gave herself enough room to tug at both my boxers and jeans and all at once freed my big young cock that slapped heavily against my stomach. I’m just under 8 inches in length with above average girth and in her small hand it made me look enormous.

“I knew it.” She groaned as she squeezed the base of my shaft just above my well groomed balls. She held me up vertically and gave me a couple slow strokes, seeming to enjoy how easily my skin moved being uncircumcised. Next, Alex pulled her bikini bottoms to the side revealing a small tuff of dark public hair and her dripping lips. She grinded along the underside of my length a couple of times, soaking me before leaning forward over my chest and guiding my thick head to her entrance. When she slipped me inside and immediately took most of my length I gasped and clenched both her asscheeks under her bottoms with both hands.

“Fuck. Don’t move for a sec.” I managed to stammer. She sat still, straddling me with her hands on my chest while I took it all in. Her pussy was so wet and felt so different from what I was used to. I don’t know if it was her having already had two kids or the fact that she was more experienced but with my size I had never been so deep inside someone. I bit my lip and nodded at her and she immediately started to grind her pussy down onto me, her juices flowing down each side of my hips along her soft legs. She bucked up and down on my cock that was a little more vertical than I usually liked it to be but that actually made me happy because it was going to keep me from cumming too soon.

“That’s it, ride me!” I encouraged her as I slide my hands up her flat stomach and put my rough palms over her hard nipples. She responded with a whimper and a quickening pace, the sound of wet slapping starting to fill the room each time her thighs hit my hips. I’m pretty sure I was laying in a massive puddle on her bed and I loved every second of it.

It wasn’t long before she was clenching her teeth and her eyes were fluttering as she stopped bouncing and went back to just grinding with my entire length inside of her. I sucked on my thumb a little to get it nice and wet before pressing it to her clit and rubbing softly sending her to orgasm. Her legs quivered and her muscular torso clenched as she let out a few uncontrollable groans before laying down against my chest to catch her breath, “That… that was unbelievable.” She stammered while I brushed her hair to the side out of my face.

“You feel so good.” I answered kissing the top of her head. We stayed like that for a few minutes, just enjoying being wrapped up in each other while I throbbed inside of her.

“How do you want to cum?” She asked using her hands to raise her self up and look down at me again in the same position she had been riding in.

“Lay on your back?” I suggested and she raised herself up just enough that I could watch my cock slide out of her. She rolled closer to the side of the bed so I picked her up and recentered her so we were in the same position we were in when I had carried her upstairs. I wrapped my hand around my thick slippery shaft and guided the head to her lips, running the tip the length of them.

Wiggling her hips at me she playfully acted stern, “Don’t you dare tease.”

I slid back inside her while she held her head up off the bed to watch. I was just as impressed by her as she was by me as inch after inch of my long thick shaft disappeared into her warm wet cunt until my balls were against her asshole. She had winced just a little with the last half inch or so but assured me she wanted it, “I love how big you feel inside me.”

I am extremely turned on by dirty talk but up until this point in my life had had to encourage it from the young women I had been with but that was definitely not the case with Alex. As I started to move my hips back and forth a change came over her…

“Fuck my wet married pussy.”

“You’re twice as big as my husband.”

“Break me with that fat young cock!”

I was in heaven, I honestly don’t have any clue as to how I lasted as long as I did the first time with her but it was a few minutes later that I was putting everything I had into thrusting myself as deep as I could inside of her. Our bodies slapped together as I laid over top of her pounding myself down into her petite body while she wrapped her arms and legs around me.

“I want to make that big young cock spurt!” Alex whimpered underneath me sending me past the point of no return. I pulled out as quickly as I could, but the first rope of thick cum escaped and hit her pussy before I could raise my aim and shoot the rest up her perfect sweaty body. I had never cum so hard up until that point and I admired the mess I was making as she had ropes of sticky cum up and down her body from her nipples to her tuff of pubic hair. While I tried to catch my breath she ran her thumb along the cum dripping slit of my cock head and then put it to her lips to taste me without saying a word, instead just sighing exhaustedly and laying her head back down flat on the bed.

I laid down beside her on my side while she laid flat on her back and turned her face towards me, “I needed that,” She laughed her small chest still heaving, “Wanna shower?”

Source: reddit.com/r/gonewildstories/comments/u0j8dh/fooling_around_with_my_moms_former_boss_part_1