My First MILF

It was a fairly large supermarket. I got a job there to pay for my travels six months down the line. I was the fruit and veg guy, in charge of doing the ordering and putting out the stock. Every so often I'd work in the bakery section but that was about it. I was a young lad at the time, 19. Single and pretty horny like most guys of that age. I had a fairly good build, by no means toned but I was still strong and in good shape. At the time I was about 5ft 9" with blue eyes and short brown hair which I always styled off to the side. I was broad shouldered with strong muscular legs and modestly endowed with an 8" cock. For what I thought I lacked in length, I definitely made up for in thickness.

There was this assistant store manager who was a fair bit older than me. For this story we'll call her Jess. She was 36 with a kid my age. You do the math... When I first met her, it was in the office, I was probably doing some menial job whilst she worked away.

She was a regular gym goer for someone of her age. She had medium length blonde hair that she always wore in a ponytail, blue eyes and stood at around 5ft on the dot. A nice slim physique with a fairly small but perky set of tits. She also had a great firm arse and toned legs. Nothing to write home about but definitely a milf, one that I didn't even dream of fucking until things got flirty between us...

I can't even remember how it started but we got chatting at some point at work. We would joke and have a laugh, either taking the piss out of each other or making flirty comments. I think we added each other on Facebook and then got talking outside of work through that. Again, at first it was harmless conversation, getting to know each other like friends but then things quickly turned sexual.

Bear in mind I was still pretty young and the idea of a milf was extremely attractive to me. I started to share screenshots of my conversations to her with my two friends in a small group chat we had going on. They were egging me on, telling me that she was up for it and generally encouraging me to carry on flirting with her.

A week or so passed of pretty intense flirting and the not so subtle hints of sexual innuendo in the middle of conversations. Again, I don't exactly remember how things unravelled but we decided to go to the cinema with each other. She was about a half hour train ride from me in a fairly busy town, contrasting my small village. She lived with her son at the time in a small flat in the town centre.

I remember the first time I got the train to hers, it was early evening time and starting to dim outside. As the train got closer to hers, I got excited and pretty nervous. Arriving at the station, I wandered outside of the gates and saw her coming towards me. We met up, smiled said hello and got chatting again as we walked to her flat. We still had a few hours until the film started so we decided to just hang around her apartment for a bit until we had to leave.

I remember wondering where her son was but just assumed he was with his dad, thankfully I was correct. Nothing sexual or physical happened before the cinema, we just chatted and I cracked jokes to make us relax a little. Either way you flipped it, contextually it probably looked a little odd, a young employee out with his manager at her apartment.

By the time we got out of the cinema it was pretty dark outside and the streetlights had already light up. She unexpectedly invited me back to hers which I didn't really think much of at the time, plus I knew that trains back to my village would run quite late so I was happy to stay a little longer. We made our way back to hers, up the stairs to her floor and through the door into her apartment. We sat down in the living room and again talked away through the evening. It was mainly just stuff about work or what we get up to out of work. After all, we didn't know too much about each other so it made sense to get a little closer.

Without knowing, we chatted most of the night away, to the point where I was starting to worry about missing my last train home that night. I was on the early shift the next morning so I was also pretty conscious about staying out too late. Although I was a young guy, I was pretty sensible and didn't like to be out too late if I had work the next morning. Either way, she noticed how late it was getting as well and casually offered me a bed and then would give me a lift to work the next morning. Fairly surprised by the blasé offer, I accepted.

I remember mentioning that I didn't had a toothbrush or change of clothes but she seemed to par it off casually. In hindsight, she was playing her cards very well, even writing this I'm starting to question who actually picked the other one up. I like to think that I was in control but she was a much more mature woman who clearly had a lot more experience than me.

As we turned in for the night, I began to settle down on the couch and she made her way to the bathroom. After a few minutes of her freshening up, she walked out of the bathroom and popped her head into the living room. She jokingly asked me what I was doing in there and told me to sleep on the other side of her bed with her. Instantly realising she intended on getting to know each other a step further, I lifted myself from the sofa and followed her into the bedroom.

It was a plain room with a double bed tucked into the corner with a bedside table next to it and a large wardrobe looming over the foot of the bed. She had slipped into some comfy pyjamas which I knew she intended on ripping off pretty quickly. I clearly didn't have anything to get into so stripped down into my boxers and got into bed with her.

She switched off the light and we laid there for a few moments on either side of the bed. Still chatting about random stuff, we seemed to naturally gravitate toward each other. I could sense her mouth just inches from mine as we had our heads on the pillow. My heart raced and we slowly leaned in to kiss for the first time. The first thing I remember was her mouth wide open, this wasn't a slow passionate kiss. This was a hot and fast snog. It turned me on.

Our bodies quickly intertwined and I soon positioned myself on top of her, still snogging and biting each other's necks, lips and ears. I was rock hard at the time and kept gently pushing it against her pussy. Grinding slowly to tease her into getting wet. Every minute that passed, she seemed to fully let loose and put all of her body into it. It was as if I had awoken something in her as she convulsed and moaned as I grinded myself against her.

As intended earlier, I quickly ripped those pyjamas off her body, starting with her top, I lifted it above her head. I seemed to do this pretty smoothly as she wanted to keep sucking on my tongue. Next was her trousers. I lifted her bottom half up slightly, using my domineering position to keep her in place as I pulled them down to her ankles. I then dropped her back down onto the bed as threw the trousers off into the darkness of the room. I remember feeling down for her pussy and I could feel the completely waxed area above her clit.

When my hand made its way even further down, I could feel how wet and tight she was, I knew it would be a struggle to get my thick cock inside her, but the prospect excited me. Whilst my right hand was adventuring the inside of her, I used my left hand to mildly choke her as I sucked and bit on her nipples. Alternating between both of her tits, I made sure to provide her with ample satisfaction that led to her body starting to intensify in its spasms. She was starting to cum over my fingers as I fastened their pace, she was clearly loving being with a younger guy. Her mouth opened as she began to let out passionate moans. The neighbours below must have had a great image of what was happening from both her moans and my deep commands.

Once she had finished cumming, I begun to position my pelvis in front of hers. She was clearly lusting for my thick cock and was begging for me to fuck her. I told her to stretch her pussy apart as I spat over my dick to lubricate it, she clearly didn't need me to spit on her as her pussy was already glistening from her cum and juices. I positioned the tip of my cock right by her hole and began to arch my hips and slowly push inside her. She was so tight I had to keep bringing my dick back and trying again. You could tell she was getting frustrated by being teased so much, she just wanted my cock inside her.

Soon, I was able to get another inch in and another, slowly my cock started to disappear inside of her as she let out the most incredible moans you could imagine. It made me want to start fucking her as hard as possible but I knew I would hurt her if I did. Knowing I was firmly inside her, I brought up my hands and grabbed both of her wrists and placed them above her head so I could pin her down, at the same time I resumed making out with her. Her lips were eagerly awaiting mine as I sucked and bit her tongue.

My hips began to find a fast rhythm as I pumped her, with each sexual release from her, it spurred me on, motivating me to thrust into her further and harder. Her tits began to jiggle up and down as I fucked her relentlessly. The beauty of the missionary position is the ability to see their reaction to each thrust as you hit the right spot.

After a little while in this position, I decided to slide my cock out and bring her on top of me. I collapsed next to her, sweat dripping down my forehead and back. Using what strength I could muster, I grabbed her hips and pulled her up on top of me. All the while she maintained the intense snogging, raising her pussy above the top of my shaft. She grasped the bottom of my raging erect cock into her stretched pussy. She managed to slide herself all the way down until I hit the back of her pussy and her body recoiled in pleasure.

She managed to push through the convulsions that seemed to halt her and start bouncing on me. Her gym days seemed to come into their element here and she furiously rode my dick as if her life depended on it. Rocking back and forth, she hit her G-spot, making her pussy tighten around the thick base of my dick. It was covered in her cum and about to be drenched by a wave more. I could see the globules of her white cum begin to stream down my dick, creaming all over my hairy balls.

I decided it was my turn to take over here and pushed her ass in the air slightly, holding her mid-air with both of my hands, wrapping my big hands around those firm ass cheeks gave me the ability to control her every move. I started to thrust my hips upward, hard and fast. Taking the entire length of my cock, repeatedly hitting all the rights spots combined with my balls smacking against her tight arsehole seemed to make her cum immensely quickly this time.

Within seconds she was screaming in an ecstasy of pleasure as the rolled off my dick and onto her side. I paused briefly, deciding it was my turn to cum and as I pulled her ass into the air and positioned her legs and back into the doggy position.

When I decide to cum, it usually takes me seconds, I stiffen my legs and let all inhibitions loose as I go wild. I decided to start slow, then I pulled both of her arms behind her shoulders with both of my arms, meaning I was the only thing holding her up on my dick. Without warning I quickened my pace and systematically pummelled her pussy with my hard strokes.

She was taking my dick so well, pretty quickly the feel of her pussy around my dick was too much. The sight of her body made me want to shoot my load inside her and watch it drip out of her hot cunt. However, I knew that would be risky as I wasn't wearing a condom. Releasing her hands and letting her upper body slump into the bed, I pulled my dick out and aimed it just above her ass cheeks. With just a few small strokes, I streams of my hot cum blasted out over her ass. Jet after jet seemed to continue coming until my balls were completely empty and my cum was running down over the top of her pussy and dripping onto the bed. I thought she'd be mad that my cum was all over her bed sheets but she didn't seem to care, instead she turned round, sat down and pulled me in for more kissing and nipple sucking.

We must have fucked three or four more times into the early hours of the morning where we got dressed and ready to leave. For a few more months after that, we met up, fucked and carried this on until I went travelling. I have plenty more stories and encounters like that with her, which I might publish on here depending on the reaction of this one. I hope you enjoyed my first proper erotic story, stay tuned for more!