Since my last story turned out to be such a success, I was inspired to write a few more of mine, starting with this one from a few months back. Fair warning, it’s going to get wordy. I like to write.
Samantha was technically my boss according to the company org chart, but for the most part I was hired so that she didn’t have to deal with the things I was going to be handling anymore. We operated more like peers than supervisor/employee, so work-wise everything was great. Personally, we hit it off pretty well. We’re about the same age, we’re both married, she was pregnant with her first kid when I was hired several years ago, so we would often talk about that.
Physically, she’s like a 9.5 out of 10. She’s big into fitness and running. She’s about 5’8″, very athletically slim with a nice set of what’s maybe B cups, and an ass that is an HR violation waiting to happen.
Anyway, this spring the company decided that I would be going to a conference with Samantha as representatives of the company. At the time, my wife and I had been in a bit of a bedroom drought for some unsexy reasons that would definitely detract from the story and she’d been stronger and stronger hinting that I should maybe find someone to take care of my needs since she wasn’t able to. Before I left for the airport, she told me that I needed to find someone to take care of my needs while I was out there. I talked it down because truthfully, it’s always felt like something that would be more fun in fantasy than reality. But she insisted that I should and that I shouldn’t feel guilty about it. I said I’d think about it, said my goodbyes, and was off.
The first day of the conference went great. After a day of meetings and sessions and small talk, Samantha and I compared notes over dinner at the hotel restaurant before heading back to our separate rooms for the evening. I flipped the TV to ESPN or something like that and began mindlessly wasting my time on the Internet. My phone buzzed. “I hope your dick is deep in some conference slut bunny right now,” read the text from my wife. I was like, damn, who is this woman? I texted back that I wasn’t and had no plans to be. “I’m disappointed,” is all she texted back. I rolled my eyes and tossed my phone over on the bed.
A few minutes later though, my curiosity got the better of me and I downloaded Tinder. Swiping through and I think the fourth or fifth profile I came to was Samantha. My jaw dropped as I processed A) why she would be on it and B) what I should do. Do I swipe right and maybe match or do I swipe left and maybe she swiped right and gets mad. Either way looked like a possible L. So I turned the phone off and decided a shower was in order.
After a nice hot shower, I threw on a tshirt and some boxers to prep for bed and took a look at my phone. In my notifications was a text from Samantha. “Hey… Awkward, I know, but I think I saw you on Tinder. Aren’t you married?”
I replied, “I am. But so are you.”
She replied, “Yeah, but hotels make me horny. Tinder was a no go though.”
I replied, “Hotels are the worst for that. And your secret is safe, I won’t tell your husband.”
She replied, “He knows. Hell, half the time he watches. Does your wife know?”
I replied, “Wow, really? It was actually her idea. We’re in a bit of a dry spell. But I don’t know.”
She replied, “How long?”
I replied, “About four months now.”
It went quiet on the other end, so I returned my attention to my laptop. A few minutes later there was a soft knock at my door. I got up and peeped through the hole to see Samantha standing there.
“Hey, got a minute to chat?” she asked when I opened the door. I invited her in and we made small talk for a few minutes. She also looked ready for bed with her hair up in a pony tail and wearing a white tank top and some gray shorts, which left very little about her body to the imagination. After some random work related question she finally got to her point in a run-on sentence kind of way. “So, I know we work together, and that could be awkward, but I won’t be awkward if you won’t, you handle things well, I like that about you, well not like like that but like, and it sounds like we both want to get off, so how about we just take care of each other and move on?”
The thought of it flashed through my mind and straight to my dick as it jumped to life against the fabric of my shorts. It caught her eye and she started laughing. “That looks like a yes to me!”
She laid out some ground rules and asked if I was good with them. I agreed and she motioned me to sit on the edge of the bed. At this point she took her time getting undressed. Slowly pulling her tank top off which really showed off her muscles. The girl was in really good shape for having had three kids. I didn’t have abs that good when I was playing baseball and working out every day. She turned around as she started to slide her shorts to the ground. Once they fell to her ankles she bent over slightly and stuck out her ass.
I reached out and gave it a grab. It was so tight while I squeezed it. I think “Damn,” is what I muttered under my breath.
“Yeah, I’ve caught you looking a few times,” she said.
“Sorry,” I said sheepishly.
“I work hard on it, I’m glad you noticed,” she said. With that she dropped to her knees in front of me and began playing with my hard dick through the fabric of my shorts. If I hadn’t just jerked one out in the shower 15 minutes ago, I probably would have blown my load right there. Before long she stopped teasing, pulled my shorts off, and wasted no time getting to work on my thick six inches.
This woman knew what she was doing with a dick. Licking the shaft, bobbing on the head, swirling it with her tongue, playing with the frenulum, playing with the balls. I was in heaven. I laid all the way back and just enjoyed as she worked on my dick. She slowed down the pace a little bit and I looked up and our eyes met. At that moment she went all the way down. The corners of my eyes started to go blurry as I felt my dick push against the back of her throat. She took me all the way.
She came up for air several seconds later and had a long string of drool that reached from her chin to the tip of my dick. She had a big grin on her face as she quickly did it again, came off and bobbed on the head for a moment or two, and then did it again. It had been a very long time since I’d had someone effortlessly deepthroat me like she was.
She kept it up and I began feeling the urge to cum building. “If you don’t stop, I’m going to cum,” I said. She went down all the way once more and then pulled off. She wiped another string of saliva from her chin as she gave me a devilish smile.
“How do you want me?” she asked.
I thought about it for a moment before I led her into the bathroom and quickly positioned her bent over the counter and swung one of her legs up onto it as I entered her from behind. I paced my thrusting initially as I began to explore her body. Running my hands down her back, grabbing her ass, and down her leg. I reached up at one point and grabbed a fistful of hair and gave her a light tug as our eyes met and she moaned. I reached around and played with her breasts too and gave a pinch to her right nipple as her eyes half rolled back as she moaned again.
I moved her a little further upright to get a better look at her breasts in the mirror when she suddenly gasped. “Oh, fuck, right there. Fucking right there.” She started getting more and more vocal as I continued my thrusting. “Yes, there! Yes, there!” she whispered as I could feel her pussy contracting around my dick with each trust. She put a hand on the mirror as I could tell she went over the edge into an orgasm. Her pussy contracted so hard that it pushed my dick out and in that moment she squirted all over the floor.
I wasted no time as I lined back up to slide back in as she reached a hand back against my stomach to hold me off as she laid on the counter catching her breath. “I need a minute.” I cleaned up the puddle from the floor as we laughed about it. She suggested we go back to the bed where she climbed back between my legs when we did with my dick back in her mouth. After a minute or two she popped off and asked, “Forward or reverse?”
“Reverse,” I answered almost as quickly as she answered it. She laughed as she spun around and positioned herself and slid me right in reverse cowgirl. I wasted no time getting my hands all over that perfect ass.
“Go ahead and spank me,” she said. So I gave her a firm spank. “Don’t hold back, let me have it.” So I gave her a much harder spank and she moaned in a way that I don’t even have words to describe it. “Yeah, like that, more,” she said as I began mixing in some hard spanks with my squeezes as she rode me. Before too long her ass was visibly red from the pounding I was giving it while she rode me.
She picked up the pace on my dick and I could tell she was playing with herself as well and as my hands went to her hips, I could feel us both building up to orgasm. Her pussy was tightening and my urge was building. I was groaning trying to hold off with everything I had. “I’m not going to make it,” I said as I admitted defeat.
“My face! Cum on my face!” she said. She hopped off the bed and to her knees as I jumped up next to her. She quickly grabbed my dick and began jerking. A few moments later I unloaded two or three good spurts of cum across her face.
I tucked a strand of hair behind her ear as we looked at each other with grins ear to ear. “I thought that was a against the rules,” I said to her, referring to cumming on her face.
“I kind of lost track of what the rules were when you made me cum earlier,” she replied.
As she got up to go to the bathroom and clean off her face, I sat down on the bed, expecting her to get dressed and head back to her room after she was done cleaning up. Instead, she climbed into bed next to me and I didn’t miss the opportunity to quickly slide down between her legs and get to work.
She was so wet and turned on, it didn’t really take very long for the combination of my tongue and fingers to find her second orgasm of the night. Afterwards she asked if she could stay the night. I said yes and we fell asleep next to each other.
I’d like to say we fucked a dozen times the rest of the night and then in the shower the next morning, but in reality, she woke up around 6 and got dressed. Before she left she gave me a quick peck on the cheek and thanked me. We had one more night there, but nothing happened then either. Or since. The topic hasn’t even been brought up since we returned home.
It was a fun way to spend the evening and I definitely enjoyed it, but there’s a reason I chose my wife.
My wife on the other hand was very interested to hear every detail after I confessed what happened. She later confessed that it had long been a fantasy of hers to “loan me out” and she was too embarrassed to admit it to me. She also said she wants to try it again sometime with her in the next room overhearing, but there are no plans.
I guess 2019 has been the year of both of us crossing some fantasies off the list.
Source: reddit.com/r/gonewildstories/comments/cxrutn/mf_breaking_the_rules_with_my_boss
Wow, that was awesome! ???