Unexpected Coworker (M/F) | 2016

I had recently taken to working out at the company gym. I was able to beat traffic, it was free and most of all, it was part of my making changes. I had amicably ended things with my fiancee. I was offered a job in another state that was far too good to pass up. She had reasons why should couldn’t leave. That was the end of that. Few people took advantage of the gym and despite thousands of people working for the company, there were never more than a dozen people working out in the morning.

Sheryl was the girlfriend of a co-worker, Rob. She was there every singe day and while we were certainly were friendly before, we became even more so and often ate breakfast together, another company perk for our division. Everyone knew I was going to take the new job, but they didn’t know I wouldn’t be taking Paula, my now ex. Cheryl was one of the first people at work that I told of the break and she correctly guessed that it was the reason for my change in routine. She was permanently upbeat, a touch nerdy and genuine.

It was a Friday and as we left the gym, Cheryl said that we should get dinner. I said sure and didn’t think anything of it. We met that night and sat across from each other in an oversize booth in a popular pub. Rob wasn’t with her and that struck me but I didn’t say anything. We had some good conversation, she asked about Paula, the job and then told me that she and Rob were ‘up in the air’ following a ‘where is our relationship headed’ conversation. I was enjoying myself and laughing with her when the waitress came to close out, as the kitchen was closing and the place made it’s transformation to more of a bar.

I reached for my wallet and it wasn’t there. Somehow, I broke the tradition of phone, wallet, keys on my way out that evening. Cheryl really didn’t mind and thought it was funny. I was completely embarrassed. She played it up, jokingly accusing me of doing it on purpose. As she was signing the check, she gave me a smirk and said she’d let me work off my debt. Even at this point, I am on par with a rock for perception skills.

Until now, she was not someone I had a sexual thought about. I had been in a committed relationship and she was my co-workers girlfriend, at least until recently. She’s never given any indication of being interested in me and now my gears were starting to turn.

I walked her to her car, or more accurately, her enormous SUV. It was winter in Michigan and bitter cold. As we got to her door, I gave her a hug and said goodnight. She looked at me like I said something dumb. “Come here.” Walked back up to her and she reached out to hug me. I thought she just wanted to hug me goodnight. She hugged me and held me, whispering in my ear that it was time to work off my debt. Her hands slid to my neck and she kissed me. I kissed her back. We continued until the cold started to bite. “Get in.”, she said. As we did, she told me that for a smart guy, I missed all her signals.

We continued to kiss in the car and it quickly warmed up. We moved to the back and took off our jackets. After 3 years with my ex, this was the first person other than her I’d touched. I must have given some cue as she said for me to follow her lead. I kissed her neck and ran my hands all over her body. She loved to be kissed on the neck and moaned as I hit the right spot. It was nicely warm and she undressed me down to my underwear. She slipped out of her shoes and skirt. She pulled her sweater over her head leaving her in bra and leggings. It was in the dim light that I realized she has a fantastic body that she doesn’t show at all. Even in the gym, the sports bra and huge oversize shirt hid this from me. She’s 5’6” and smaller, but not tiny. The tights accentuated her waist and I couldn’t wait to take them off her.

20 minutes earlier, I was wondering what I should watch on Netflix when I got home. Now I’m about to have sex with Cheryl. As I continue to kiss her, I try to take her tights down. She stops me, but doesn’t stop kissing me. She pulls on me to slide to the middle of the backseat and she kisses her way to my waist. She takes my boxers down and off. I’m completely naked. My cock is hard and she grabs it, stroking very slowly.

“I wasn’t going to let you leave, you know.”

“i’m beginning to see that.” I said

“Do you miss fucking Paula? When was the last time you fucked her?” she asked while not missing a stroke and her eyes locked on me.

Paula was 25, two years younger than me and virgin. A very, very religious family, so sex was off the table until marriage. Even engaged, she wouldn’t. She offered up anal sex, but despite lube, prepping and positions, we only got my finger inside her. I literally only got the tip in when she made me stop. Her blowjobs were ok but she would tire quickly. Her go to was hand jobs. She loved when I came on her. That was the best part, I suppose. Almost every morning she gave me a hand job and she would finish me on various parts of her body and then get in the shower. But no sex. I told Cheryl all of this as she stroked me.

Cheryl put on a pouty face and said “Poor baby! Let me make it better”. She continued to stoke me and took my cock in her mouth. She used her mouth and hand in unison. She hummed. I was rock hard and in heaven. Her hand and mouth felt amazing. I felt I would come and told her. She took her mouth off and said to tell her before I come. The dash clock said she had been blowing me for only 4 minuets but I was going to come and I didn’t care. All I could muster was “Ok!” and Cheryl moved her hands to my ass and took me all the way in until her nose was in my pubic hair. She bobbed as I came. I came hard and it felt so good. She kept me in her mouth as I softened, trying to draw more come from my cock.

“I told you I have no gag reflex.” she said and noted another signal I missed. I kissed her some more then she took off her bra and leggings. She was completely naked and if I hadn’t just come, I’d have been rock hard again. How had she been hiding this body, I wondered. As I kissed her, I began to finger her pussy. I curled my finger and stroked the bumpy flesh on the top of her vagina. She liked that. I inserted a second finger and kept stroking. I kept my fingers in her as I knelt before her and began to suck on her clit, rolling it between my lips. I may not have been able to fuck my fiancee but I did go down on her - a lot. Cheryl liked the same things Paula did. Cheryl started talking dirty and I never knew it was such a turn on. She asked if I was trying to make her come, she asked how I liked her little pussy and it was all such a turn on. I licked fingered and sucked until Cheryl said she came 3 times.

“I want you to fuck me” she said. I was ready to go again. “Do you have a condom?” I didn’t, explaining again that I didn’t have sex with my ex. She didn’t have any and I was hoping for another blow job. She moved toward the front seats and grabbed something, telling me she’s got this. I couldn’t see what she grabbed and for a moment she looked like she might be inserting a diaphragm. She rubbed her hands together quickly and then grabbed my cock. Her hands were covered in lube and she was rubbing it all over my cock. She then told me this is really expensive hand cream, not lube.

“You are going to fuck me in the ass, ok?” “Uh, sure.” I said.

Cheryl had lubed up her ass and my cock, then she told me to sit in the middle. She moved in front of me and stroked my cock and then slowly guided it in her ass until she was sitting fully in my lap. She moaned and said to be still. My cock felt great in her ass and she began to move slowly up and down. She handed me the lube and told me to put more on the head of my dick and push in her ass. I complied. She was comfortable and we fucked faster and faster. I had never fucked a girl in the ass before and it was amazing. The sight of her great ass swallowing up my cock is something I’ll never forget. I reached around and rubbed her clit and she exploded in moans. “ Sorry I’m so loud”, she said. I kept fucking her ass and rubbing her clit. She moved my hand aside and said “Let me get in there.” as she played with her pussy.

This was more fun and exciting sex than I’d ever had with Paula and I felt an orgasm coming soon. I asked Cheryl if I should come in her ass or if she wanted it on her tits. She replied “ Are you going to come again? Right now?” I said that not right now, but soon in the next minute. She kept playing with her pussy but leaned back and her arms dashed toward each door, one than the next. She had opened the windows. Cold poured in the car. She said keep fucking me and played with her pussy and I fucked her ass. It was probably just 30 seconds before she put them up again. It was a great feeling to sense the warming up again from the cold as I kept pumping into her ass. “I wanted to buy us more time.” she said and it worked. It was so cold I though I was going to go soft but I fucked her for a while longer.

She told me to come in her ass. I pumped her as she played with her clit and I came. I kissed her and held her with my hands still roaming her body. I couldn’t believe this happened with her. I couldn’t believe that she had such a body under her conservative clothes and most of all I couldn’t believe that I had just had the best sex of my life with her.

As we cleaned up and dressed, I said we should do this again. If I didn’t live with roommates that worked with us, I’d have fucked her again. Indoors this time. We didn’t hook up again, as she and Rob were ‘kind of’ back together.

The annual spring party for our division was at a large waterside vacation home of one of the top executives. She was there and Rob was too. People knew us as work out buddies and that I was leaving in a few days for the new job, after several delays. So no one suspected that she talked dirty to me all night, grabbed my cock as often as she could get away with it. The sexual tension was enormous. She pretended to have a stomach ache so she could give me a blowjob in the garden. She told me she wanted my cum in her ass tonight. I was walking around a work party half erect. When a large group of people from the party went across the property to see the horses, Rob included, we had our chance.

She had lube this time and had already lubed her ass up, hoping we got a chance to fuck. I joked with her as she rubbed on my cock, “Go easy with that stuff, it’s expensive hand cream!” I fucked her in the ass in the bathroom and we watched ourselves in the mirror. I came and had to leave quickly so we didn’t get caught. I never saw her again but a few weeks ago, I got a text from her. It was a picture of the expensive hand cream bottle with a note, “ This is expensive hand cream. You should try it.”