My coworker’s daughter

I’ve had some interesting experiences over the years. I’m not sure how many I want to post yet so I’m starting with this to gauge the response. Also new to writing stuff like this so lmk if more/less detail would be preferred. In hindsight this ended up quite long. The text messages I quote aren’t exact, it happened a while ago so I’m going off of memory and filling in the details knowing the general spirit of what happened.
I’m in my 50’s now, but this particular experience occurred about 10 years ago. I was a director in a tech-type corporate job (keeping details limited). I had a team of 6 managers working for me, with about 5 employees each. We usually hired a few interns over the summer to do the shitty work no one wanted to do, but we mostly used it as a way to screen for potential new employees. Because of that we took it seriously since the goal was eventually to hire one or more of the interns. We usually got quite a few applicants, so when one manager under me, Jim, mentioned his daughter was looking for an internship, I was hesitant to waste a spot on someone further away from graduating than we typically took (we preferred grad-level students, Jim’s daughter Ali was in between her freshman and sophomore years of undergrad, she was 19 at the time). I figured why not at least give her the interview experience, Jim had been working a lot of hours and I wanted to keep him happy. I didn’t interview any candidates, but to my surprise Ali was pretty clearly in the top tier that the interview team recommended. I was extremely hesitant but they advocated for her so hard I decided to give her a shot. There was always the added bonus of keeping my best employee happy too, so why not.
On the interns’ first day I had a welcome meeting with the entire team to make sure everyone knew each other and felt comfortable. As the four fresh faces nervously introduced themselves, I was impressed Ali didn’t sit next to her dad or mention him. She wanted to get by on her own work. She was extremely formal when she spoke. Her black suit pants, black top, and thin black jacket were slightly more formal than the other women in the office, just enough for it to be obvious this was her first day. Ali was a beautiful young woman, long black hair, dark olive skin, smiling a lot, very skinny, though it was hard to tell much about her body beyond that. When she smiled at you, you instinctively smiled back. In contrast to the other female intern she wasn’t showing any skin and was not wearing tight pants, so the men who thought they were being sly were all checking out the other intern.
I didn’t interact much with the interns on a day to day basis, but about a week into the job she stopped in my office and thanked me for the opportunity. I think she wanted to make sure I thought highly of her because of her dad, but I think she also realized she was at least 3 years younger than the other interns and was genuinely thankful for taking a chance on her. It was a professional conversation, just letting me know she was willing to work on anything the group needed help with. Two things stuck out though, she definitely laughed a lot more than my first interaction with her, and she was wearing a lower cut top. No cleavage, but there was a tattoo visible that caught my attention. I’m not sure if it was intentional, there was nothing inappropriate, but I love tattoos on women and that combined with the extra skin was just enough to catch my attention.
I’d see Ali a few times per week in the halls and around our offices. Typically very professionally dressed, but showing just enough skin to catch my attention some days. She was beautiful, and much younger, though not the type that I’ve typically found myself with. I forced myself to stay professional despite the fact I was definitely starting to notice her more. I made a point of walking by her desk more often, even including her in meetings more often.
One morning about two weeks into the internship I got a text from a number that wasn’t in my contacts. It was Ali and she got a flat tire on the way to work. She must’ve gotten my number from her dad, which impressed me that she hadn’t just told him to tell me. Of course the flat wasn’t a big deal, but that opened the door to her texting me more and more often. It started mostly logistical, “can I take Friday off” type messages, then became comments about the office or meetings, all professional and innocent. I did notice more emojis from her, and she switched from using my last name to my first name. After a meeting where it was obvious I was disappointed in the work coming from the team she was on, I got a text “hey B, let me know if you have a minute.” Unsure of why it was a text and not an IM, I told her she could stop by my office after 4. She popped in around 4:15 looking dejected and immediately apologized. I smiled for the first time that day, maybe because she looked so pretty, maybe because she had zero fault in the her team having a bad meeting earlier but still apologized. I got a call after a few minutes of small talk so I stood up and walked out of my office. When I walked back in that’s when I stopped dead in my tracks. She was sitting in the same spot, in the chair opposite my desk, facing away from me, and I noticed the tiniest, thinnest pink g string I’ve seen in my life, just sticking out of her pants. In reality it was nothing, I’ve seen a thousand images more revealing in my life, but something about this girl that was so much younger, who I had control over at work, whose father I had control over at work, who rarely wears anything remotely revealing, having her g string just poking out. I felt something come over me, animalistic, that I had only felt a few times before. I kept it professional, but as she walked out of my office a few minutes later I couldn’t help but think about what her ass was like, and what it would look like in that tiny g string while walking away from me. I definitely thought about that image a few times that night, each time getting slightly more embarrassed I was thinking about her sexually. At the very least I wasn’t worried about the shitty meeting earlier anymore. Two beers, a few instances thinking about Ali and I was starting to fall asleep when I got a text. “Hey B, hope your day got better ‘wink emoji’, see you at the office tomorrow.” I was up for an hour wondering if the wink emoji meant anything, I felt like a teenager again reading into every comment.
I tried to avoid her the next day so I didn’t say anything stupid. But she walked by my office about a dozen times, way more than normal. It was especially noteable because she was wearing a skirt for the first time. Her legs were incredible, long, smooth, tan. It stopped me in my tracks every time she walked by. The last time she walked by I noticed her look back at me as I was stealing a glance. She was completely in my head.
That happened on a Friday. The following Sunday I got a text from Ali “hey are you in the office tomorrow?” This was not typical so it definitely got my attention. I replied “hi Ali, yeah I will be, do you need help with something?” She replied “actually yeah, maybe I can show you something when you’re done with meetings?” Unsure of why she just didn’t set up a meeting, I replied “of course, I’ll let you know when I’m done.”
Ali was wearing a skirt again on Monday. The first time she walked by she said good morning to me and gave me the prettiest smile. I was thinking about her all morning, wondering if she was wearing a g string again, wondering what she wanted to talk about. The next time I saw her, she was walking back from lunch with her dad. I hadn’t seen them even acknowledge each other before this, it seemed like she was wanting to make it on her own which I really respected. I was behind them and when they got to the front door of the building she stood on her toes and gave him a kiss on the cheek before walking in the building. It was innocent but I felt that animal urge inside of me again. She was just daddy’s little girl, and he had no idea I was getting hints of interest from her. I was even more distracted that afternoon. When my meetings finally ended I needed a break. It was a long day and I was fighting thinking about my intern’s legs and what she was wearing under her skirt all day. I definitely had a bulge forming but I’d be behind my desk so I was safe. I IM’ed her and she came in my office around 5:15. I don’t think it was intentional but she didn’t cross her legs right away and I immediately got an answer to one of my questions. She was wearing some sort of lacy black lingerie. And she saw my eyes move from her 19 year old legs to her eyes. I got nervous for a split second but her smile made me feel better. She talked about work and complained about a friend from school that canceled living plans at college for the next year. I just listened and gave advice. We started smiling more, less work talk, more laughing. At one point she got up to pour a cup of coffee that was in the back corner of my office. I still don’t know if it was intentional but she dropped her cup before filling it up and bent down to pick it up. She could have bent at the knees, or faced me to bend over, but without hesitating she bent over straight legged, back slightly arched. The black lingerie was another g string. The image of her almost naked ass bending over will be burned in my brain forever. As she stood up and the skirt started to cover everything up, I noticed how firm her ass was. She was hiding an incredible body. She left without further incident but I was addicted. Was that intentional? Is it ok that I feel this way about someone so young? Should I feel bad that I like the power dynamic? What if her dad found out? If she was hiding that ass this whole time then what else is she hiding?
I decided to text her first for once, I was finally feeling bold enough. “Hey Ali, thanks for stopping by, not sure I helped you with what you needed but you made my work day a lot more fun.” I got nervous immediately after. What was I doing? I’m in my forties, she’s less than half my age. We were both single but i was still nervous. I needed to take the edge off my nerves so I opened a beer, which turned into three by the time she responded. “Hey B, you made the day more fun too ‘wink emoji’ maybe we should hang out at the end of the day more often?” I had just gotten off for the second time to the image of her tight little ass bending over in my office, but the thought of her coming back, and what would happen next, made me hard immediately.
I had an easy day the next day, but thinking about Ali was driving me insane. I often hung back at meetings to make sure no one saw my bulge. Around lunch I realized I hadn’t seen Ali yet. Weird, but maybe she was just busy. Around 4 Jim stopped over and apologized that Ali couldn’t make it into work, she hadn’t been feeling well and he made her stay home. Not a problem at all, though I was bummed for reasons Jim would never guess. We chatted for a while, we talked about his project, golf, but eventually Ali came up. He talked glowingly about her and I said how impressed I was with her work so far. All I could think about was how she flashed her ass to me right where he was standing about 25 hours earlier.
I got a text on my way home that day “sorry I didn’t make it in today, my dad made me stay home. I’m feeling fine though and I definitely didn’t forget about you, can we keep our date for tomorrow?” …date? Prob just a funny comment from a teenager… “hey no problem, hope you’re feeling better. And you know you’re welcome in my office anytime you want ‘wink emoji’” I got a smiley face and a halo emoji in return.
The next day was a long one. Full day of high level meetings. I couldn’t wait for 5. Since I was in meetings I hadn’t seen Ali, so I was pleasantly surprised to see another skirt and those gorgeous legs. She crossed her legs immediately so no sneak peak, damn. We immediately started joking and laughing. She complimented my suit, that was the first time she had seen me in one. She even mentioned she was familiar with the brand (it was high end) and always tried to get her dad to wear that specific brand, to no avail. It was the first time she had compared us in any way, not sure why but it was a turn on. I felt myself getting hard. We kept talking but a few minutes later she asked me to look at something on her desk. I think she knew what I was hiding under my desk. I kind of panicked but stood up. She didn’t notice right away but when she turned around her eyes went straight to my bulge. She didn’t flinch. She stopped in her tracks and asked if I was ok. She bit her lips and looked up at me. (I’m slightly above average, thicker than most but maybe around average length). I stopped just short of her.
“Yeah just distracted”
“By what”
“The cute girl in front of me. Wondering what color panties she has on today. Wondering what else she’s hiding under those clothes”
She smiled, shut the door, walked towards me, and we kissed. It was passionate immediately. Without saying a word she grabbed my bulge and felt it get harder. I kissed her neck and she took that as a sign to pull off her top. She was wearing a leopard bra, with her beautiful tits spilling out. Damn, she’s been hiding an amazing pair of tits too. We kissed more and I grabbed her shoulders, guided her towards my desk, and sat her on it. We kissed more and I let my hands go under her skirt. No underwear. As my hands slid up her smooth thighs it got warmer. Then wetter. She was soaked. Her hand undid my belt, then my pants. I hadn’t even processed what was happening, it was just total lust. I undid her bra and I’ll never forget the image. I prefer smaller tits and had definitely tried to imagine hers, but these were beyond anything I imagined. Firm, round, perfect size nipples, no tan lines. They bounced once as she removed the bra before I had to have them in my mouth. Apparently they were super sensitive bc she started moaning immediately. I wanted to suck and bite them more but there was something else I wanted more. I wanted to know how good this 19 year old intern tasted. I wanted to know how tight my employee’s daughter’s teen pussy was. Her hand was pulling down my pants. My cock jumped out and I’ll never forget the look in her eyes when she saw a man’s cock for the first time. From our convos I knew she had broken up with her last boyfriend who was “older” at 21 years old. As she started wrapping her fingers around my cock, her dad’s boss was sliding his thumb up and down her slit. Her back arched, she wanted more. I laid her down on the desk and kissed around her thighs and stomach, circling around her tight little teenage pussy. By the time I got there she was begging. I found the tongue motion that made her squirm and made her cum in under a minute. She gave me a look that I’ll never forget, lust and passion and a desire to do nothing but make me cum. She got on her knees and wrapped both her hands around my cock, kissed the head, licked the bottom from the balls to the tip, looking me in the eyes the entire time. I was her dad’s boss, but in that moment she controlled everything about me. To this day that is the best blowjob I’ve gotten. I blew a huge load down her throat and she didn’t hesitate to swallow every drop. I sat down in one of the chairs, I didn’t even know what had happened but it felt amazing. She wasn’t done though. She straddled me, took my cock in her hand and kissed me again. After I got hard again I threw her back on the desk and went down on her again. I needed more of that pussy. I made her cum twice this time. I stood up, looked her in the eyes, rotated her around, and slid my cock in her tight wet pussy from behind. We were in the office so I was refraining from anything that would be loud, but she loved me pulling her hair and playing with her nipples. I asked her where she wanted it and she said inside her. I knew that probably wasn’t a great idea but I blew my second load deep inside her. We both collapsed. Her on the desk me back in the chair.
Afterwards we both agreed we wanted more, but finding time and place was going to be a challenge.
I have some other stories with Ali, we stayed close all summer. I also have some other experiences with other women if there’s demand for this sort of thing. This was on the long side, but open to any feedback or questions about Ali.