This story happened quite recently. It was around Christmas, to be precise. Let me start by saying that I work as a junior associate at a local law firm in a relatively small town. We were going on a collective vacation at our firm for the holidays, and our bosses decided to mark the occasion with a little celebration at a local country club.
I and some coworkers got lost on our way to that place but finally made it there. We sat down and started to chat with each other while we were having lunch. I wasn’t very invested in everything that was going around. All I was looking forward to was finally being on vacation after a very long and stressful year. The restaurant where our little party was taking place was nearby the club’s pool, and it was there that something or better someone caught my attention.
Walking by the pool, there she was. She was about 5.5 or sum like that, white-pale skin tone, short blonde hair, wearing jean shorts and an oversized buttoned blue shirt, and I was mesmerized looking at her. Even tho the shirt she had on her was oversized, you could see that she was hiding something big underneath it.
Anyways, after she caught my attention, my mind got back to the party. It was time for the Christmas presents. Every one of the firm’s employees got something. Some of the oldest employees got a tv as a reward for their loyalty. I decided to walk one of my coworkers to her car and help her carry the TV there. We were all set and done, and to my surprise, I ran into the girl I’d seen earlier by the pool. She was picking up something from her car. I being the dork I am, decided to try to break the ice by commenting on her car. She politely replied and said it wasn’t hers but her mom’s, it was a Volvo SUV. We walked together back from the parking lot to the restaurant/pool, chatting a bit.
In our little chat, we got to introduce ourselves. Let’s call her Anna. She told me she and her family were from out of town and were here only visiting for the holidays. We eventually reached the pool area. I said my goodbyes and went back to the firm’s party. Our bosses told us the bar’s tab was open so we could have whatever we wanted, so you better believe a bunch of overworked stressed-out lawyers were getting drunk there and then.
I made my way to the bar, and asked for a beer, and who should I run into again but sweet Anna, she said hello again, and asked me what was up with that bunch of drunk attorneys, I did my best to try to explain to her that we were on a mission to get the bar tab as high as possible to try and piss off our boss, and I asked her if she wanted in on our little plot, she laughed and said yes, so I ordered a drink for her.
I sat down with her at the bar, and we chatted a bit more. She told me she was 21, and that she was attending business school. Although the conversation was good, and she had a pair of beautiful blue eyes, and couldn’t help myself and ended up constantly staring at her breast, fantasizing about them, imagining what they looked like, trying to take a glimpse of them. We finished our drinks, and she went back to her family, and me to a party that seemed boring when I could be just staring at her shirt.
Eventually, the firm’s party was over, and I was heading towards my car in the parking lot, I walked by the pool to say goodbye to Anna and her response was “oh you leaving? it’s still pretty early”, so me, trying to tease her and see if I could take this any further said to her “I don’t know, give me a reason to stay”, she immediately picked on my message, giggled and said, “First round it’s on me”. We went back to the bar, sat down, and started to have beers together, while we chatted about everything and nothing at the same time, you know, that kind of conversation.
As the alcohol levels in our blood started to rise, so did the heat of the conversation. We started to tell each other lewd stories about past experiences. I told her about the time I fucked an ex-girlfriend in a law school empty classroom, that story seemed to turn her on, because she told me about how she blew up a guy on a vacation trip, and I took it as a sign.
I decided to rise the stakes and proposed to her we play a truth-or-dare game. whatever restrictions were in place before had gone out of the window. It started mostly as a truth game, but as we move on with the question, I felt something on my leg, I took a look under the table, and wouldn’t you know it, it was her trying to tease me, at a point, she stopped playing with my leg, leaned towards me to ask a question, with the perfect angle so I could take a sneak peek at her tits. Add that to the conversation we were having and It was hard as a rock.
The first dare of the night came, I told her “I dare you to unbutton your shorts”. She gave me a cheeky look and told me to look below the table; she was wearing beautiful blue panties that matched perfectly with the shirt and shorts. Her turn, she laughed and told “I dare you to unbutton my shirt”. I was confused, not like I hadn’t been thinking about doing it the whole time, but she caught me off-guard, but I’m not one to not take advantage of an opportunity like that, so I stood up, took her by her hand, and walk her to the parking lot. She still had her shorts unbuttoned, once where are there, I asked “yours or mine?”, she seemed confused, I just repeated the question, and she said “mine”, so I took her to her car, I put her against one of the doors facing me, and I slowly unbuttoned just one of the buttons of her shirt, we were close to each other, so close I could hear breathing. I lean towards her and give her a gentle kiss on her lips.
Next thing you know, we’re full-on making up. She has her arms around my back, while I have mine at the top of her shorts. I softly bite her on her upper lip, and she lets out this little cute moan, she then takes one of her hands to the front of my pants and goes down on me till she found my cock, and gave it a little stroke. We stopped kissing, take a look at each other and I ask her if she has her keys on her, she franticly searches her pockets, until she finds them, she opens the door, and we went in. I took a seat, and she proceeded to sit on my lap, facing me, we started making out again, but now I take it a little further and start kissing her neck, what was before a soft moan, grows louder, I stopped kissing her neck for a moment, and look at her unbuttoned shorts, and can see a little wet spot.
I told her to turn around, so it is her back against my chest, and she obliged. As soon as she was settled in this new position, I started to kiss her neck from behind, while going down her body with my hand, I caressed her belly, as I made my way down her body. I finally reached her panties and started to rub her pussy very gently, while still kissing her neck from the back. I could feel her getting more wet as the minutes passed by, so wet that she got my fingers wet too, so of course, I made her lick them.
She got up, turned around, unzipped my jeans, grabbed my cock, and started to give me some head. I tried to be gentle, so I was kinda caressing her hair, she seemed like she knew was she was doing, but I had to stop her because I was getting close to cumming, since we’d been fooling around for a while. Read more »