That time I bought a sex toy with [M]y [F]emale boss

Long ago in another time and place, I worked nights in a crappy retail job. I say it was crappy, but in reality I enjoyed it. The work was easy. The hours were reasonable. I got along with my coworkers. And, I was the only male night shift employee.

I worked with the same couple of women, including my boss, for several months. We fell into a relaxed relationship and felt comfortable talking and teasing each other about practically any subject. Many of our conversations became sexual, though not overtly, about sex. We would dare each other to flash the others or talk about our sexual prowess or tease each other about how much they would enjoy having sex. Like I said, we had an easy and relaxed relationship.

My boss was an attractive woman only slightly older than I was at the time. I was mid-20’s. Michelle (not her real name) was around 30. She was tall, almost 6′ and had an athletic build. She didn’t go to the gym but had played sports throughout school and stayed active enough to stay in decent shape. Michelle had nice, smallish breasts that didn’t need, and frequently weren’t, to be constrained by a bra. Her ass, however, was awesome. These were the days before Kim Kardashian, so her ass wasn’t huge, but it filled out her tight fitting jeans very nicely. I always tried to sneak a peak when I thought I could get away with it (and sometimes when I knew I couldn’t).

I was in my mid-20’s. I have always been pretty average in the looks department. Not good looking enough to be desired by the hot women, but not repulsive either. At the time I enjoyed the decent weight and build that comes with youth.

I would follow Michelle to the bank for our deposit when we closed the store together. For several months we had been teasing each other. I, like most young guys, had been telling her how much she would enjoy having sex with me. I told her several times how she would be screaming my name and not be able to walk straight the next day. For her part, Michelle told me that I couldn’t handle a woman like her. She said I would never be able to satisfy her. She told me how she would tear me apart.

One fateful night, Michelle stated rather matter-of-factly that she wanted to buy a strap-on dildo but wasn’t sure which one to get. This was the early 90’s and I was fairly naive about sex, especially sex toys. I asked her what a strap-on was. As she described it to me, I must have had a curious look on my face. After talking about it for a few minutes, I volunteered to help her find the right one (like I had any idea about such things). She seemed relieved and asked if I was serious. I assured her I was serious. I suggested that we go after work to the adult toy store less than a mile from our store. She agreed.

We decided to ride together to the toy store so neither of us would chicken out. We sheepishly browsed around the store until we found the section with strap-on harnesses and dildos. As the selection wasn’t vast, it didn’t take long before we both decided that the right one for her was just a simple harness and a beige, non-realistic dildo about 5 inches long and fairly thin. I “expertly” advised her that it fit her frame the best and looked like it would be her size if she had an actual dick. She didn’t seem to be as convinced as I was so I told her the only way to be positive would be to try it on at home and return it if she wasn’t sure. I thought, naively, that this would finally be my big chance to see her ass outside of those jeans. If only I knew what was to come.

I drove us to her apartment. Not wasting any time, I suggested that she try on her new toy so we could verify that it looked right for her. I waited anxiously on her couch while she went to her bedroom to put it on. I’m sure my jaw hit the floor when she returned. She had teased out her hair and changed into a form fitting t-shirt and her strap-on harness and nothing else. She looked beautiful and sexy as hell standing in front of me with one hand on the door frame and the other at her side like Kelly LeBrock in Weird Science.

I must have stared and been speechless for too long for her confidence. She looked disappointed, insulted, and turned to go back into her room. I finally found my voice. “Holy shit! You look amazing,” I told her.

“Really? You aren’t just saying that?”

I told her I thought she looked sexy and asked her to come closer so I see it up close. She came to me and held it gingerly with one hand. I could tell she was excited by the moisture dripping down her leg. I asked her if I could touch it. She said yes, but I told her I was only used to seeing and feeling dicks from behind them. I got up and stood behind her, my hard on pushing into her ass through my jeans as I reached around her waist to grab the first dick other than my own.

“It’s perfect,” I said. “Just the right size and shape for you. I like it.”

“I can tell by that thing poking my ass that you like it,” she told me. “Why don’t you show me how much you like it and take those pants off?”

I quickly undressed and must have looked utterly ridiculous. I was standing in front of my sexy boss staring at her new dick with my shirt unbuttoned, jeans on the floor in a heap, one sock, and tighty whities with my rock hard cock straining to get out.

“Nice. Now take the rest off so I can get a look at you. After all, you’ve already seen mine,” she said.

I finished undressing, and she reached out and grabbed by hard dick. I almost came right then. She told me, “hold on cowboy. I’m not finished with you yet.”

We started kissing and grabbing each other like two sex-crazed teenagers. We stumbled into her bedroom and fell onto the bed. Before I knew it, she had climbed on top of me. I couldn’t take my eyes off her as she slid my cock into her wet pussy. We fell into a nice rhythm. I was pushing, trying to get as deep as possible. She was grinding me with her head flung back in ecstasy, still wearing that sexy, black, v-neck t-shirt.

I finally came to my senses and grabbed her by the hips. I flipped her over onto her back and pushed into her. As I did, she wrapped her long legs around my waist and pulled me close and tight. We fucked like that for a few minutes before I felt my impending eruption.

“I’m going to cum,” I panted, expecting her to release me.

“As long as you don’t stop until I do,” she replied.

With that, I shot my load into her but didn’t stop thrusting for more than a couple of beats. As I continued pounding away, she finally tensed up and clutched the sheets like in a white knuckle death grip. I started rotating my hips as I ground as deep as my cock could go and didn’t stop until she quit shaking.

As I collapsed on top of her, she whispered in my ear, “next time, it’s my turn.”

Sadly, there was never a next time. We continued to work together for a couple of more months before the store closed and we lost contact with each other. Working together after that was still comfortable and not the least bit awkward. Looking back, I wish I had pushed for our “next time,” but the timing was never right for another night together. I will never forget that night with my boss or how incredibly sexy she was with that strap-on and t-shirt.

Source: reddit.com/r/gonewildstories/comments/8x9exu/that_time_i_bought_a_sex_toy_with_my_female_boss