[M]y Office MIL[F] experience

A little background: I'm 26, tall, decent looking half-Indian guy, who went to college around Philly. I know everyone thinks all the stories here are fake, so I am keeping it as honest and detailed as possible. A few years ago, after my junior year of college, I had an internship in the city.

There was a pretty hot receptionist/admin lady at this firm, let's call her Rachel, who helped us with our paperwork and general stuff around the office. She was about 28-30, blonde shortish hair, 5'5 or so, with a great ass and big B cups. Not exactly an hourglass figure, but not too far off either, and very friendly. As a 20 year old, I never really thought I had a chance, and though we flirted and talked a little bit, nothing really happened apart from smoking together with other people a couple of times.

I actually became FWBs with one of the other interns, finished the internship and went back to school. More than a year later, after graduating, I was working at a different place in the city and went out for after-work drinks with a few colleagues. We had knocked back a few cocktails when I see Rachel and a couple of her friends come into the bar.

It is pretty crowded at this point, and they are waiting for the bar pretty close to our table, so I go over and say Hi to her. She was wearing a black dress that made her look pretty curvy, and we began talking. She recently had quit the place where I had interned, and was working Admin at another place close by. I was drunk and a little over-familiar, asking about colleagues we both knew and so on and asking her to come join our table.

After getting drinks, they come and start talking to some of us. One of her friends knows a girl from my office and everyone is getting along great. Rachel sat at the other end of the table from me and I tried not to act disappointed, telling myself it was stupid to think she would be interested in a 21 year old. When some other people get up to get drinks, she comes and sits next to me, and we keep talking.

I am wondering whether she was just friendly or whether I should make a move, and pretty drunk at this point, so when the colleagues close to us are absorbed in the conversation, I decide to go for it. Embarrassingly enough, the best I can think of is 'I don't want to be weird, but I always thought you were so hot', and after drunkenly blurting it out, I am terrified she is going to just get up and walk away. Instead she laughs and says thank you, then brazenly asks why I didn't do anything about it. I look around but nobody at the table is too focused on us, and my tongue is absolutely in knots.

I mumble something incoherent and she puts her hand on my pants and starts stroking through the fabric, all the while staring at me. I guess I must have smiled because she did too, and I put my hand on her thigh and started moving upward, careful to pretend we were still in conversation and make sure nobody saw. After a minute of this, she whispers into my ear saying 'I'm gonna go to the bathroom then walk outside, come out in a minute.'

So she leaves me sitting there with almost a full hard-on, shocked and tipsy, wondering if this is some grand prank or dream. I calm myself and make some excuse about a cigarette, literally counting the seconds, then go outside, half expecting her to have changed her mind or disappeared. But there she is outside, and she pulls my hand and gets us to a cab at the corner. She asks if I have a place and I say yes, about 10 blocks away, so I tell the guy where to go.

In my head I'm a little worried that people maybe chilling with my roommate or at my apartment, but he had planned to go out, and anyway Rachel started kissing me in the cab so I stopped thinking about it. We got to my place and sat down on my bed, kissing furiously. She unbuckled my pants and started stroking through my boxers, while my hands roamed all over her body.

The boxers came off and she put her mouth around my cock, bobbing up and down then teasing me with her tongue. I thought I was going to come in a micro-second, so after a couple of minutes I pushed her onto the bed, pulled down her panties, pushed up her dress and started eating her out. I could feel her wetness on my tongue, and I kept flicking in and out till her moans got louder and my cock recovered a little. Then I turned around so that my cock was above her face, and she sucked as I went down again, both of us almost shaking.

After a couple of minutes of this, she pushes me around and says I want your dick in me. I am lying down now, her hand on my chest, and she turns and climbs on to my hard cock, slipping on a condom I hand her and sliding it inside her easily. She takes off her dress in one smooth motion and then pulls at my shirt and takes it off while slowly riding me. She pushes me down again and goes faster and faster, moaning and getting wetter. I am trying my best not to come instantly, and somehow manage for a few minutes while she rides me till she starts coming. I breathe heavily and tell her I am going to come soon.

She slides off me, wetter than a water park, then turns and bends over, pulling my cock into her doggy style. I barely last six thrusts and blast inside her, grabbing her ass while my cock shakes uncontrollably. She moans and keeps fucking back after I have come, and I think she came again as I finally pulled out and went soft.

Already this was amongst the best sex I ever had, and after cleaning up a little and smoking a bowl, I thought she would want to leave, since I remembered she was a single mom with a 2 or 3 year old. Instead she starts kissing me again and says 'I want you without a condom', and we go at it again, fucking twice till I finally dropped her home 3 hours later. We hooked up a couple of times that month, and then I went to New York and we fell out of touch, but it was definitely one of my favourite affairs.

Source: reddit.com/r/gonewildstories/comments/2z7tq9/my_office_milf_experience

9 comments

  1. > single mom with a 2 or 3 year old. Instead she starts kissing me again and says ‘I want you without a condom’ DANGER DANGER DANGER….

  2. Yes it wasn’t the best decision in hindsight, but I was drunk, horny and stupid, I don’t know many guys who would resist after round 1. Luckily I didn’t catch anything and get tested more or less regularly, but you’re right it could have turned out not so great

  3. I think the concern was also the possibility of adding onto her incoming child support payments.

  4. I would love to read some more. But try and be more descriptive with the sex part, it didn’t captivate me like these stories usually do

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