I [M] Slept With My Boss’s Daughter [F] at Her Graduation Party

It was the summer 2021 (a few months before this was written) when Covid was dying down. Everything was opening up again but renting out venues were extremely overpriced, but that didn’t stop my boss from throwing her daughter her graduation party. (I know it was stupid on her part but oh well, what can you do) I’ve been working under my boss for about 5 years now and she would talk about her daughter, River, from time to time. I’ve seen her pictures before but never in person. She looked like a smart girl and very outgoing though I didn’t pay no mind as work always kept me busy. When 2021 came along and River graduated, her mom (my boss) wanted to throw her a party before she went to University in North Carolina (University of North Carolina – Charlotte I believe).

I decide to go as it would get me some brownie points for the promotion coming up the following quarter. So we get there and her house was pretty big for the city we lived in. It was a nice environment to be in. Met my boss and she introduced me to River for the first time. I was blown away by how pretty she was. The pictures in her mom’s office did her no justice. River was 18 (I checked), had long, soft, red hair, 5’02” and looked like she weighted 100 pounds, wet. She was pretty petite as she did cheerleading all four years of high school. She had on a rather modest white sundress on that didn’t show anything too revealing. To be honest she had that innocent look to her that told me she was going to be a huge slut in college.

Her mom went back to talk to the caterer while her husband went to greet the other guests. It was me and her in the living room just chatting now. We just talked about college, sports, and other small things. It was pretty awkward for a bit so I excused my self to the restroom. The first floor was packed so I asked River if there was one upstairs that I could use. She pointed me up to the one upstairs and I went in. I didn’t have to use it, I just wanted to get a break from it all. Washed my face before heading out and I see River waiting outside her room. She asks me if I wanted to see her cheerleading trophies, to which I hesitated buy said why not in the end. I was pretty amazed at how clean and big her room was. Trophies on the walls, pictures of the family on her desk. Nice little twin bed (don’t ask me why she had a twin sized bed, puzzled me too). After she tells me about her trophies, she tells me to sit on her bed while she show me some moves. She did a few flips and cheers and I was pretty impressed at that point. She decides to sit next to me and next thing I know her hands are running up and down my thighs with her eyes looking right at mines. I was pretty fidgeting at this point and told her it wasn’t right. (I know I sound like a total white knight lol) To which she didn’t care and said she wanted to have some fun before she left for college. At this point, I said fuck it, she was willing and I was too. Though I was confused why she picked me out of all people. (I’m a overweight 230 pound man who was almost twice her age) We started making out before I laid her on her bed and hiked up her dress.

She had on a pair of white panties on to which I pull off. She had the pinkest pussy I had ever seen with a small patch of red public hair above. I started rubbing her slit while she pulled down the top of her dress to reveal her small B cups. Her nipples were hard and pink too. I couldn’t resist myself from sucking on them. I felt her hands touching my crotch area, to which I was already hard. We switched positions to which she was on top of me now. (It was pretty uncomfortable being on her small bed). She unbuckled me and pulled down my pants and my cock popped out. She started playing with my 6 inches (more like 5 and a half but who’s counting) with her soft hands. It felt so good but her mouth was even more amazing when she started sucking. I felt like I was already going to blow at this point. I pushed her off and grabbed a condom in my wallet and she insisted on wrapping my cock herself. She was playing with it for a while before I told her to get on her back. We started off with missionary, well all we did was missionary but felt amazing.

Her soft moans as I was thrusting in and out of her, the way her small breasts jiggled. Her bed was creaking so loud that I thought the guest downstairs were going to hear us or that her bed was going to break. After about 5 minutes, I could feel her quivering under me. She laughed and told me she just came. I did try my best to hold on from cumming but could only last about 10 minutes because of how tight she was. I popped inside the condom before pulling out. I didn’t think I could cum so much when I saw that there was a sizable amount of cum in the condom. We were both pretty exhausted at this point but I told her to smile. I pulled off the rubber and poured the cum all over her braces, to which she was giggling uncontrollably, which was cute as fuck to be honest. She swallowed what she could before we cleaned ourselves up. We left one at a time to the party downstairs to avoid suspicions. We met up a few times that night and had some small talk. Apparently I was her 3rd guy ever. She only had 2 boyfriends ever. One of which showed up later that night with roses. They did kiss later that night which made me chuckle. If he knew how dirty her mouth was haha. Never saw River again since that night. Probably getting ready to leave for University right now. I don’t think I will ever forget her.

Source: reddit.com/r/gonewildstories/comments/of7ta8/i_m_slept_with_my_bosss_daughter_f_at_her