(M22) (F30) (Proposition) Desperate Coworker

While I was in college I worked for my dads company. I filled in wherever I was needed, especially in the summer. I was working in the scheduling department one summer until they got a backfill for the position. When they finally hired someone they brought her around to my desk to introduce her. Holy shit, she was hot. Her name was Val, she was about 5’10 and around 30 years old. She was well dressed and wearing an appropriate length skirt for the office but it still showed off a lot of her legs. She had a desk but I told her I would train her for a few weeks at mine.

The following Monday Val found me, pulled up a chair and sort of snuggled in. She seemed to have a nice personality and did not appear to be shy. She had the vibe that she was slightly rough around the edges.

After letting her work on a task by herself, she became frustrated when she messed up a couple of times and let out a “Oh Fuck Me !!” Her face turned as pale as I had ever seen. She was already intimidated that I was the owner’s son. She started apologizing. I laughed and said “Don’t worry about what you say around me, but I wouldn’t let anybody else hear you.” That seemed to loosen her up and after that she wasn’t as nervous.

Over the next few days we got to know each other, she told me about her recent divorce and that she was left high and dry. She went back to school and this was the best position she has ever had. That’s why she was so worried about getting in trouble and losing the job.

One Monday she was acting off. Val wasn’t in her usual upbeat mood. Although the ringer was turned off, her phone was blowing up. I asked her if she needed to answer it, she said “No it would do any good anyway.” I asked her “Is everything okay?” She responded in almost a tearful voice “Not really.” I said “Let’s take a break and go get some lunch. I forgot to buy your onboarding lunch anyway.”

She looked pretty stressed so I took to my favorite dive bar not far from my apartment.

I ordered a beer and told her to get whatever she wanted. She ordered a drink and told me she is not doing well financially. She said she felt comfortable around me so she told me that she previously had worked as a dancer at a strip club but thought she was getting a bit old for that. Since she got the position at my dads company she was really trying to get her shit together to keep a good job. But her bills were coming faster than her new paychecks were and was afraid of being evicted.

She said she would go back to the club but was too afraid of someone from work recognizing her. She sadly chuckled and said “I might have to start selling my ass on the side of the road.”

I almost choked on my beer! I said “If you do, you better call me first!!” She halfway laughed and ordered another beer. On the way back I told her “Look, for some fucked up reason I believe you are really struggling and that you are really trying. If you need to borrow some money for a while I will loan it to you.”.

A couple of days later she asked if I was serious about the loan. I said “Of course.” She asked “What if I can’t pay it back in time?” I said jokingly “I know how you can pay me back.”. She said “Oh I bet you do.”.

A few weeks after I gave her the money, we were at my desk and she said quietly “I’m not going to be able to pay you back when I said I could. If I do, I will be back in the same boat.” I said “Well take a little longer, or make some payments.” She said “I’ve owed people money my whole life, I don’t want this hanging over me like everything always does.”. She asked “How else could I pay you back?”.

My jaw dropped. I laughed and said “Ok then, show up at my place naked a couple of times and we will call it even.” Right then of course someone walked up to the desk with a question and interrupted the conversation.

The following Saturday afternoon there was a knock on my door. Val was standing there wearing a typical t-shirt and tight jeans. She looked even better away from the office. She barged in. I thought to myself, she isn’t naked so she must have gotten some money.

She strolled in and asked “Do you have anything to drink?” I got her a glass of bourbon, she downed it and said “I was thinking a couple of quickies and one really good fuck should cover the debt. Ok? Plus you have to swear no one at work finds out about this!” All I could get out was “Um, Ok.”

She headed to the bedroom and started undressing. She pulled the t-shirt over her head and some firm B-cups bounced out. She kicked off her shoes, pushed her jeans and panties off. She laid back on the edge of the bed resting on her elbows. She put her feet up on the bed and spread her legs. She said “All yours.”.

I have never gotten undressed so fast in my life. My dick already hard, sprang out of my shorts. I put my hands on her knees and followed her thighs all the way to her tits. Rubbed her nipples between my fingers, then followed her torso down to her pussy. It looked like she had just shaved it clean. I trailed my fingers from her clit down to her asshole. She closed her eyes and sighed softly. I got on my knees and put my face on her inner thigh and followed it to her pussy. I had to taste it. I licked from her ass, between her lips, into her vagina as far as it would reach and up to her clit. She gasped and moaned a little. I licked and sucked on her delicious clit. She grabbed the back of my head and pushed my face deeper into her pussy. In just a couple of minutes she wrapped those long legs around me and convulsed, squeezing me with her fit thighs.

I stood up with my cock sticking straight out. She brought a foot , still wearing her socks, up to my balls. She placed her foot under my balls, and worked it up massaging them slightly. She then trailed her foot along the length of my cock. She smiled and said “Oh you like that.” She pulled her sock off and worked her beautiful painted toes around on my balls. Again she went up the length of my shaft and swirled pre-cum on her toes.

My cock had never been harder. I took her feet and put them up on my chest. I rubbed the head of it on her clit. She didn’t ask for a condom so I didn’t mention it. She took my cock and guided it in. Her pussy was as tight as any college girl I had been with. I worked my cock in until it was balls deep. She stretched her arms above her head and I thrust in and out for about five minutes. Her beautiful tits were matching the motion.

Val pushed me off of her and turned over. She stuck her ass up in the air and my cock found its way back into her pussy by itself. To my surprise she started thrusting back and forth on my cock. It was such a sensation like I had not felt. I couldn’t take much more.

Moaning with the thrusts, she looked back at me. She could tell I was about to cum. She suddenly flipped around and sat on the edge of the bed. She stroked my cock with one hand and massaged my balls with the other. As I started cumming she leaned back on the bed, spread her legs and milked my cock and balls for everything they had.

I lay on the bed beside her catching my breath. She lay there for a minute covered in cum. I had blasted it from her pussy, up her belly, and all over her tits. Even a little on her face.

She stood up and headed toward the shower. She said “Holy shit, I wasn’t expecting to cum.” then she asked “How was that for the first payment?” Once again in all my smoothness all I could get out was “Um,Ya.”.

As she was leaving she said, “We’ll do something really fun next time.” I thought to myself, if this is how she’s going to pay me back maybe I will up the credit limit.

Source: reddit.com/r/Erotica/comments/10k9ru7/m22_f30_proposition_desperate_coworker