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.
It was an uneventful night and I had dinner with friends that followed with drinks at a bar that was packed with 20 somethings. Nothing special, just a bar after 11PM on a Thursday night.
In ordering drinks through the crowd, I was bumped into by a beautiful blonde. She was cute, all decked out in a tube top and short skirt so I immediately asked her what she needed and got the bartenders attention. Just trying to be a gentleman, I said “I’ll grab your round”. She handed me her card (which I didn’t put on her tab) and placed my order while she darted back to a table against the wall away from the crowed in front of the bartenders well.
**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.
Full disclosure: Brittany and I are dating and decided to make this account. Pic is from another night. Enjoy!
It was a warm Friday night at the beginning of the summer, and the night of my friend’s 21st birthday. As much as I wanted to join the celebration, I had an important certification exam the next morning, and I was determined to show up without a hangover. However, my friends are very persuasive, and eventually I agreed to “one drink and one hour.”
Since I was only there to see a few friends, the kind of friends you have long since stopped trying to impress, I went to the party in my well worn study clothes. I had been at the party for about a minute when I saw her.
Shit. It was Brittany, a gorgeous girl I had matched with on Tinder and been talking to, but had not met in person yet. Evidently she knew that I would probably end up at this party and made hints about it, but I somehow missed the memo entirely. She was wearing a little black outfit that accentuated her thick little ass. She was 5’ 2”, Asian, and a rising senior (in college) like myself. She was wildly confident and had every reason to be. For context, I’m 5’ 9”, white, and thin but muscular.
[Part 1](https://www.reddit.com/r/gonewildstories/comments/7ppp3y/mf_a_much_anticipated_meeting/)
She had stripped from her black outfit and was wearing a lacy lingerie set. The black stockings matched her tiny and soaked thong and her bra was see through and showed off her gorgeous breasts. The best part was seeing her sittin on my chair with her legs spread. Her hand rubbing her clit furiously with a glazed look in her eyes. She apologized but she couldn’t wait to be touched she said. I told her to keep
Going and took a seat in front of her and watched as I stroked my hard on.
At this point it was all carnal desire. She knew how badly I wanted her and she teased me on purpose cause she knows how I get. I savored the sight of her rubbing her wet pussy on my chair while wearing the sexiest lingerie. As good as she looked, I knew she would taste better. So I dropped to my knees and tossed my shirt to the side.
When I was 20 years old I moved into a townhouse on campus with 3 other friends, 2 guys and 1 girl. Her name is Ashley and she was in a horrible on/off relationship with one of the other guys whose name is Ben for a few years. It didn’t take long after us all moving in together that she ended it for good.
Ben had another girl in a couple weeks that was coming over all the time until Ashley told her she wasn’t welcome there. So then he was gone all the time at her place and my other roommate was almost always working or gone for some other reason, leaving Ashley and I to start spending a lot of time together.
So I’ve never been pregnant, but my wife has.
I love anal sex. I think it’s a combination of putting my penis somewhere it doesn’t often get to go and also just how God damn well it squeezes my cock. We’d tried anal a number of times previously and despite how much I like it, it’d never progressed very far because it’s a pretty tight hole and I’m too damn conscientious to just ram it in there. It’d always be a slow process that usually ended in my just rubbing my cock up and down her ass crack (still hot). Then she got pregnant. About half way in to the pregnancy and a few minor problems that resulted in us not being allowed to do PIV sex, my lovely wife (knowing how much of a sexual creature I am and how blue my balls were getting) let me try the hole that’s usually reserved for when my begging has worn her down and she just wants to shut me up.
I think it must be about 10 years ago now that I [f]irst went out wearing a butt plug. I wanted a new frill and come up with the idea. I had use a butt plug a few times during sex but never actually wore one for any length of time. At the time I only had a pink silicon one with a suction cup on the bottom. Not the most attractive but it was all I had.
I stuck it on the bath and lubed it up. I was wearing a flowing skirt which I lifted up to expose my bare ass and guided myself onto the 6” long phallic. It took a few attempts to line it up with my tight hole. I was tempted to just push my pussy down on it and fuck myself but resisted and eased the slippery probe into my arse. The top slipped in easy but the bulbous stretched me hard and I had to take it gently. I lifted up and down a few times to help the lube spread around before finally sitting right down on it.
After getting my 1st blowjob from my close friend Jessica I was on on top of the world! Although I was being delusional with the idea that I was something of a player now it did help me lose my virginity with Melissa. Who’s Melissa? Well, Melissa was the Hispanic girl everyone in school would stare. I never admitted it to Jessica that the guys would talk about her much more than her! Jessica and Melissa weren’t exactly friend…I’d call it frenemies, so she wasn’t really into the fact that I though she was hot. Like I said she was hot, In my school she was a Goddess. Melissa had those succulent Hispanic lips and big hazel eyes. Melissa had brown shoulder length hair and large tits. She was average height with a plump butt and she would always wear high waisted jeans and tight shirts tucked in accentuating her figure.
I hope you are all enjoying the saga so far. The first two times my wife Jane, her best friend Stacy, and I were together were each special fantasies come to life, but they still happened in a “one-time-thing” kind of mindset. After the 2nd night was over, we realized and acknowledged that this was an incredible experience and we couldn’t get enough of each other.
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This is another long one. Skip down for less buildup and more details
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Since we all worked together, the next few weeks were even more sexually charged and it took every ounce of control I had not to eye-fuck Stacy every time I saw her in the halls or when she would walk by my desk. Our teaser game of “I don’t believe you” when she would tell me she wasn’t wearing panties on a given day escalated to her sending proof to me and Jane. The group texts were full of innuendos and building anticipation of the next time we could be together. In individual texts Jane and I would take our own approach and showing Stacy just how much we liked her and what we wanted to do to her. While I wasn’t privy to their private conversations, I would hear second-hand about the sexual buildup and the discussions of sucking each other’s tits and their desire to lick each other’s pussies again.