collection of stories you shouldn't read at work
BACKGROUND:
Me and Caitlin have known each other since high school. We’ve maintained a close relationship even during times where we haven’t gotten to see each other often. Coming back home after a tough week of exams, she was one of the people I was looking forward to seeing during my Christmas Holiday.
Jennifer stopped by my place on the way home from work and just barged on in. She had taken to doing this, not knocking like a normal guest. Today she was wearing shorts and a tank top, not a normal outfit for her to wear to work. “What’s up?” I asked her. She told me about how her and the other secretary, a married mother of two a couple years older than me named Tanya, had served drinks at a charity golf tournament for the day. She laughed when she admitted that the tips weren’t good until they took off their bras and poured water on their shirts. Her story had its intended effect, and she smiled her devilish grin at my noticeable reaction. “Can I ask you for a favor?” she asked.
Jennifer was one of those girls who had always been around the family. When I was growing up, her family’s picture had been hanging on our wall, her parents being close friends of mine. As a kid, I had seen her and her brother a couple of times, on holidays when our parents went on motorcycle trips and we hung out together while they were gone. Her family lived about 30 minutes away, in a rural area. She had always been kind of cute, but with a healthy dose of baby fat.
When I was in college, my parents got the crazy idea to buy a farm and get horses. They ended up buying the farm right next door to Jennifer’s family farm. Those farms were small, both about fifteen acres, so the houses were within view of each other, almost at shouting distance.
**TLDR:** I’ve spanked seven different women in the backseats of five different vehicles over the past 23 years.
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**Mazda 626**
The first time I gave a backseat spanking, it was in my Mazda 626. My girlfriend and I had already experimented with spanking, but when you’re in high school, you have to make do with what you can. I distinctly remember parking at a park near her house and turning her backside bright-red. I won’t go into detail beyond that because of our ages, but it did happen more than once.
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**Toyota Prius 2G**
You’d be surprised how much room there is in the back of a second-generation Prius — you know, after they stopped looking like Tercels but before the taillights started looking ridiculous.
How could I forget June 14th? Just seeing the date written out makes me start to lose myself in the memories.
I had taken the week off work to use up some vacation days. My wife was at work and I was enjoying entering into an alcohol-fueled stupor in the backyard. Elle was next door, goofing around in the pool after having graduated from high school the previous weekend.
It felt like August came early. The beer bottle and my forehead had the same beads of moisture clinging to their respective surfaces.
If I turned just right I could see her through the fence–running around in a little pink bikini with the cutesy skull designs on it. She was not remotely close to a curvy girl, but it was a flattering swimsuit. The boys over there with her certainly acted quite stimulated by the skin she was showing off.
Going into the second hour, I had grown tired of listening to those dopes fawn over Elle. The three of them had no subtlety at all. She pretended to enjoy their flattery, but it was obvious even from where I was sitting that she was not impressed by their overly effusive praise. She saw them for what they were: clueless teenage boys saying anything to try to get in her tight pink bikini bottom, but they had no idea what to do if they got that chance.
Please see [my first Millie post](https://www.reddit.com/r/gonewildstories/comments/7pgbeg/angry_fucking_my_ex_in_the_park_next_to_her_house/) for a description of Millie and our relationship. The long and the short of it is that I dated Millie through high school and one year of college, that Millie is great, and that she had small tits, a beautiful round ass, and a hairy pussy.
Millie and I were on a nerdy academic team in high school. It met two or three times a week, but practice never started within 2 hours of the end of classes. Even though we both had cars by senior year, it didn’t make too much sense to go anywhere. So, we got creative with that extra time.
Millie and I were always tearing at each others clothes. Our need to explore each other’s bodies was insatiable, but we rarely had time alone. Even though her mom was almost always home, Millie’s basement was the place where we fooled around most. Basically we would pretend to watch TV, but one of each of our hands would be in the others’ pants. If we heard the door close or the shower start, we’d assume we had enough time to fuck. She wore skirts when she could, and I’d pull just my dick out of my fly so I could quietly penetrate her while her parents were milling about upstairs. Her mom would often come down to do laundry when I was over, so we often had to suddenly sit up and act normal whenever we heard the telltale squeak of feet on the first step.
[Intro] I dated a girl through most of high school and the first year of college [2012]. Lets call her Millie. We were crazy about each other and had a very active sex life. While we remained friends after we broke up, we found it hard to stop having sex with each other. The last time we saw each other was in 2016. We were both in town for winter break and both single[ish] so we fucked and sexted incessantly. I’m afraid that I ruined our relationship/friendship this time around, or her new boyfriend is [understandably] concerned about our getting together, because she politely blows me off whenever I try to get a coffee with her when we both come home for breaks from grad school. Maybe that rejection is what is fueling my need to put my sexy memories of her into words? Anyway, onto the smut.
I sat in my garage for a few minutes after Joe dropped me off. With some strategic placement of my jacket that I was holding after we dropped Amy off, I was able to disguise the mess his daughter forced me to make in my pants. The next trick was getting my pants and boxers washed before my wife, Karen, spotted the evidence of my afternoon delight. Thankfully, she was busy preparing for a party we were hosting that night and I was able to slip past her to get to the laundry room off the garage.
My phone buzzed as I was changing into some workout clothes, but before I could grab it my wife opened the door to the garage. “There you are–I thought I heard you come in the front door. Why didn’t you say hi? And why are you doing laundry?”
“Hey babe–we had to take Joe’s daughter to pick up some stuff for school and she dropped her frappe-whatever as she got in the car. It got all over my pants, so I wanted to wash them before the stain set.”
“Hmmmm…did you remember to put the stain stuff on it?”
In part 1, I had just broken up with my high school boyfriend, Todd. My freshman roommate at college, Kelly, decided to spend the night in with me to cheer me up and we ended up playing a drinking version of Truth or Dare. Picking up where we left off:
It’s my turn and she picks truth. I ask her the same question she just asked me, if she had ever done anything with another girl. She tells me that a couple times when she was younger, one of her friends sort of showed her how to masturbate. She explains how they would sleep over each other’s house and just do it in the dark in different beds in the same room. “It was sort of how I learned to do it,” she says with a little laugh. “Okay, Katie, truth or dare.”
I pick dare and she tells me she is going to step up the stakes a little. She dares me to open our dorm door and flash my boobs to the hallway whether there is someone there or not. I’m hesitant at first, but at this point, the alcohol starts taking over my judgment. I go to the door, open it and lift my shirt up, flashing a completely random guy walking down our hallway. Kelly and I both crack up laughing and I close the door and go back onto the bed.
I enjoyed all the feedback and kind words from my first post. I had a lot of fun sharing, so figured I would try it out again. As I’ve mentioned, I enjoy actual real stories so all of mine are 100% authentic with nothing made up or embellished. Only the names have been changed to protect the (not) innocent. This one will be told in 2 parts. Part 1 will contain most of the back story whereas part 2 will have more of the action if you feel the need to just skip ahead.