That time I banged (M)y bosses girl(f)riend while at work

Names have been changed to protect other identity.

When I was around 19 years old I got a job under the table answering the phone for an escort agency. I worked for a guy named Frank who owned the agency, all I did was answer the phones and dispatch the escort from where ever they lived. The phones were operated out of his personal home. He was married to a woman who, I'm fairly certain was more lesbian than anything else. But he had money and life was kushy. He also had a girlfriend named Laurie who stayed with them.

First Time [anal] [mf]

Background:

 

I have been obsessed with anal for as long as I can remember. The first porn I ever watched with anal was a VHS copy of "Debbie does dallas" that I snuck from my dad's stash when I was about 14, I was blown away (pun intended). I'd say about 90% of the porn I watch is anal related and although I do enjoy vaginal sex I fucking love anal! It's so hot and dirty that I just can't help myself.

 

Here is my story:

 

My girlfriend and I were teenagers when we lost our virginity to each other after being together for about 5 months. With the milestone of our virginity gone I was eager to take things to the next step and finally try anal. Problem was I really didn't know how to approach it. We really never spoke about it except in passing one day but really discussing other people, regardless of who we were talking about the sheer thought about discussing it was a massive turn on. I didn't even speak openly about it with my close friends and it felt a bit like too taboo and a hidden desire.

Then-Girl[F]riend’s First Time Flashing a Stranger Was in [M]y Car

Circa 2005: I had been dating then-girlfriend Eve (Yes, same Eve as described in “Then-Girlfriend Masturbates On Train at My Direction”) for a few months. She was 19 years old with dirty blonde hair and blue eyes. Eve was a runner in high school and had a very sexy body. She had perky breasts with small pink nipples that fit into my hands.

This was Eve’s first time as an exhibitionist, and it was by accident. It was the summer and we were both home from college. We had just started dating a few months ago. So, naturally, we were having a lot of sex. Since we were both staying at our respective parents’ homes having a lot of sex involved resourcefulness, creativity and, more often than not, my car.

On this particular weekday afternoon we were driving around looking for a place to park and have sex. We couldn’t go to anywhere public (like a park) and we couldn’t go anywhere with a lot of foot traffic (like a mall or supermarket) because we didn’t want to get caught. We decided to park in the lot of an office building. I think it was an insurance or other corporate office. We thought it was a good find because at this hour everyone who had to be there would be inside working. It didn’t get foot traffic.

[F]irst ti[m]e after her overseas trip.

This is my first post here, but my girlfriend and I love to lurk around here and send each other our favorite stories. So, to return the favor, I thought I'd post one of our recent escapades in hope that maybe some of you will do the same with your SOs.

First off, let me give some background info about us. We've been together for four years now, but a majority of our relationship has consisted of being separated by a couple hundred miles as we went to different colleges. In May, however, that changed as I graduated and decided to move in with her. It's an exciting time for us, a time that we've been looking forward to for years. But, the last obstacle before we could have what we've pined over for so long was her three week trip overseas.

I dom’d a guy (and I liked it). [F/M]

So I originally posted this as a storytelling/re-enactment type thing to /r/gonewildaudio but after only 24 hours I was so mortified by my acting skills that I took it down. It's a story I often chuckle to myself about though so I think worth sharing. And I can explain so much better in this format.


There's a long backstory to this one that gives it context. If you're just looking for the sex get to scrolling.

This takes place while I was still in grad school, after my epic summer away that started with The Rugby Player I'd decided to try to settle down, stop having random sex, and if I recall "He's Just Not that Into You" was really gaining popularity. The movie had probably just come out and all my girls were locked into the lessons in the book. So when I met this guy, let's call him Colin (not his name), I was resolved not to play the silly dickmatized girl. It also helped that I was salivating over a completely different guy at the time, a singer in a band, so I wasn't all about hooking up with Colin, at least not in the beginning.

True Story. (m)e taking her (f) shopping

This was last Summer, so I need to try this again….

I put an ad on Craigslist looking for someone to take for some sexy shopping. The idea is I would meet her at the mall, we would shop as if we were boyfriend and girlfriend, which means I would pick out skimpy outfits for her to wear, maybe feel each other up while we shop, etc.

A few responders were asking what I would buy for them. This was not an invitation for prostitution. I was not looking for a professional, but I would possibly purchase some sexy panties etc. for fun.

I finally had a real non-working woman respond. She was a little bit older, but looked pretty good in her picture.

When we met, she told me to let her know where I parked because she had a surprise for me. I thought this would mean I was actually about to meet a guy or was being setup by a guy who would drive by to see me waiting and somehow get a kick out of it. This has happened to me often.

Settling the Score [MF] [Tickling] [Oral] First post – would appreciate feed-back

He'd been working on the Jones estate for a few weeks now as a laborer, landscaper and handyman. It paid decently well, and Mercedes Jones was in the habit of making sure the people who worked for her husband were well fed on hot days. She often fixed them lemonade or coffee and brought pastries out on breaks. Mark liked her well enough (more than well enough, really, which was a distraction), but her husband was another matter entirely.

Short-tempered, picky and very much a micromanager while he was at the house, he didn't seem to believe that anyone he'd hired could do the job he wanted of them. Mercedes (or Merry, as she preferred to be called) always tried to talk him down if he was being nasty, but he didn't seem to listen to her much either. Mark never saw him raise a hand to her, but his biting remarks often left Merry shaken. She put on a brave face but Mark could see she wasn't happy while he was home. Fortunately, he was often away on business trips. Mark detested him, but not only for those reasons.

[f/m/m/m/m] Four blowjobs, a bitch, and one finished relationship

Someone asked me in a PM how my weekend was and I ended up writing enough to make a mild-ish story for you all. Sorry the writing's kinda shitty, I didn't mean for this to be posted here and now i'm too lazy to fix it. Well, here's my weekend:

I just hit up a few friends for some fun on Sat. night. I went to a friend's house to watch a movie. There was him and 3 other guys there, and one of them had his girlfriend with him. Something in the movie got us talking about blowjobs for some reason and one of the guys said he never had one before. The guy with the girlfriend said he had some good ones before, and his gf flipped the fuck out. Apparently she never would blow him, and the only other girl he dated was a friend of hers, who told her she never did suck his dick. But now the guy's saying his last girl sucked it all the time and she was good at it.

I [M] was used for sex last night by a woman and it was incredible.

Stereotypes pave the way of men to be thought of as the ones who pick up a girl, use her for sex, and send her packing. Typically their pleasure is all that's on their mind instead of the girl's.

I got to experience the other side of that for the first time last night and it makes me feel so used and dirty that I can't stop thinking about it. But in a good way. A really hot way.

So I went to a friend's birthday dinner last night. We ate, had some drinks, and relocated to a hookah bar for more drinks and some hookah, clearly.

A friend of his wasn't able to make dinner, but came to the hookah bar. I'd never met her before but when she walked in I was floored. Incredibly sexy brunette, in a short shirt with a killer body. Her ass was a thing of beauty, and she has curves in all the right places. Think Adrianne Palicki. Damn.

Anyway, I had an empty chair next to me so she sat there.

We flirted through the night, we bought each other a drink and as the night wound down we drunkenly started telling each other dirty things.

My First Threesome/Swap (m/m/f/f)

This is my first post here but I felt compelled to share what I feel is probably the hottest sex story I have or at least the one I was thinking about a lot tonight.

My girlfriend Anna and I have been together pretty steadily. We were on again off-again through high school and got together again for good when i was a sophomore in college. She is pretty much the perfect woman in my eyes. She is blessed with a naturally curvy body, 36D/28/38 and has an amazing large ass that fills out all the fancy lingerie nicely. Needless to say she look amazing in a thong. She likes to dress punk/emo/hipster with the big glasses and the flannels and her hair is always dyed a bright red. Anyway, on the surface the two of us have one of the most boring relationships you can think of with the whole high school sweetheart thing but as we've gone through college we have gotten more adventurous and into more interesting things and it all started with this story.