Getting to fuck my boss's 18 year old daughter

Back when I had just turned 21, I worked as an intern/junior sales guy downtown. There was a bar in the lobby of the big building that we worked in, and it was a routine for some of us to go down there after work on Thursdays and Fridays for a few drinks before going home.

I had been working at the company for close to a year and my boss liked me enough to join me and some friends that worked nearby for drinks every so often. Friday came around, and Dan (my boss) asked if I was planning on getting drinks after work. I said I was and that my buddy Kris who worked nearby would be joining as well. Dan mentioned that his daughter would be joining us because she was spending the night in the city to go to a concert with some friends.

5PM rolled around and we headed down to the bar. Kris was already there waiting for us and we got a table outside. I remember it being really nice out. We got our first round of drinks and had the usual talk about work stuff and what our weekend plans were. I noticed a girl that walked around the corner to the outdoor seating area and was scanning all the tables looking for someone. She was extremely attractive. She was on the shorter side, maybe 5 foot, 5"2 or something, tan, brunette, wearing a pinkish/purple summer dress that showed off her cleavage. Her hair was in a pony tail, and one thing that struck me right away was that she had really big, pretty puppy-dog eyes almost.

I didn't put two and two together and right before I was going to say something like "check out that girl" my boss said "Anna!" and waved at her. Phew. That would have sucked if I had actually said something. She smiled and walked over to our table.

"Guys, this my daughter Anna" Dan said. Me and Kris smiled and introduced ourselves as she sat down. She had a gorgeous smile as she said hey to us. We all made small talk and ordered some finger food as we finished our first round of drinks. I didn't feel like having another drink for whatever reason that day. I was planning on just heading home after and playing some video games. Dan finished his drink and checked his watch.

"I need to catch the train guys. I'll see you Monday. Anna you know where you're going right?" He said.

"Yeah, the hotel is right down the street, I'm meeting up with my friends in just a little bit". She replied.

Now that Dan had left, it was easier to have a conversation with Kris and Anna, since the boss was gone and he was also probably 30 years older than the rest of us. I asked her about the concert and her weekends to make some small talk. She was going to meet up with her friends in a little bit then head to the concert. Kris had another beer and was mostly on his phone texting his girlfriend. This lasted for a little while until Kris said he had to head out. His girlfriend was already back at his place and wanted to get dinner started.

We said bye to Kris and he left. I asked for the check and asked Anna if she knew how to get to the hotel and everything.

"Yeah I know how to get there, but my friends aren't coming down to the city for a couple more hours. Want to do something in the meantime?" She said, looking at me with those puppy dog eyes and a smirk on her face.

I wasn't sure if I was reading her right, but it kind of seemed like she was a little into me or hitting on me. I only lived about a mile away at the time and I really didn't plan on doing much that night.

"I don't have any plans. I was just going to head back to my place and take it easy tonight." I replied.

"Would you mind if we hung out until my friends get down here? I thought they'd get here earlier, I'm sorry! We can just hang at your place, I wont bother you." She said with that little smirk again.

I was more sure now that she was at a minimum at least into me. I wasn't going to say no. She was too hot. "Sure, its only a few blocks away and you can probably walk to the hotel from there once your friends get here."

I paid the check and we walked to my place. We chatted about the concert she was going to and how nice the weather was (it had just warmed up for the summer) on the way. We got to my place and thankfully my roommates weren't home. They were a messy bunch and usually hogged the living room when they were home. I didn't really know what to do when we got there, but she pretty much immediately made herself comfortable on the couch. I gave her the remote to pick something on youtube or netflix to watch and I went to the kitchen to grab us some waters.

As I came back into the living room, she was sitting in the corner of the couch with her knees up, browsing on the TV. Her dress was up over her knees a little bit, and I glimpsed down and noticed she had no panties on. Her pussy was on full display! I looked back up at her hoping that my glance didn't get noticed. I didn't think she realized that with the way she was sitting that everything under her dress was totally visible. As I darted my eyes back up to her face she definitely realized what had happened and said "oops" awkwardly and pulled her dress back down over her knees.

I sat down next to her and handed her a water and a coaster. I felt pretty awkward from what just happened and asked her if she found anything to watch. "No, I can't get any of these apps to work, they won't connect to the internet," She said. I tried restarting the tv a couple times and it wasn't working. I didn't have board games or anything else to really do in the apartment.

 

"I have netflix on my computer in my room, but theres just a bed to sit on" I said. She smiled and said that was fine, we could make it work. So we went into my room and she sat on the bed while I sat at my desk booting the computer and logging into netflix. My bed was wedged into the back corner of my room and she sat with her back against the wall while I looked for something to watch. My back was turned to her while I was a the desk. As I was scrolling through movies she said "Did you um.... see anything earlier?"

I kept scrolling through movies nervously, and didn't know what to say. I didn't want to turn around, it was too awkward. "Maybe just for a second" I said with a nervous laugh.

"Well did you like it? Did you get a good enough look?" She replied. I felt the back of my neck get hot, what the hell was going on? I still didn't want to turn around.

"I'd be lying if I said I didn't like it" I replied, scrolling faster now, not looking for anything at this point, I had no idea what to do.

"How about this?" She said, obviously wanting me to turn around now. I spun around in my desk chair to face her and the bed behind me. She was sitting at the back of the bed, with her back against the wall and her knees up again just like she was on the couch. She looked at me with a devilish smile and slowly pulled up her dress over her knees again. Once her dress was up she slowly spread her knees a little bit. I looked down and saw her pussy, but this time her hand was down there, massaging her clit.

Her eyes didn't leave mine. She wanted to see what my reaction was. I think I just said "Fuck". I just stared at it. It was perfect. Completely shaven except a little landing strip above. I was frozen. I watched her touch herself for a few seconds. My face was probably red as an apple.

"Are you going to come here?" She asked.

I got up and made my way over to the bed. I stupidly asked "What should I do?"

"Do you want to taste it?" She asked. I nodded and got on the bed, laid on my stomach between her legs and put my mouth on her pussy. She was still playing with her clit. She tasted so good. She let out a sigh as my tongue first touched her. After a few licks I could tell she wasn't going to take her hand off her clit so I started tongue fucking her while she did the work of trying to make herself come. I grabbed her hips and held her in place while I pushed my tongue inside her over and over. She let out a few moans and sighs and then started to tense up as her orgasm started to build.

As she started to come she took her free hand and pulled on the back of my head, grinding her pussy on my face as she squirmed and twitched, moaning loudly at this point. I could feel my throbbing cock pushing against the bed under me as she came. "Fuck that was so good!" She said as she relaxed after finishing her orgasm.

"Did you like that? Do I taste good?" She asked, looking down at me with her hand still on the back of my head. "Fuck yes it did, I loved it" I replied.

"Can I taste you now?" She asked, smiling down at me. I nodded. "Good" she said as she got up and laid next to me. She flipped me onto my back and got on top of me. She gave me a kiss full of tongue as she straddled me and felt my cock through my pants. I helped her take them off and she moved lower so that her face was over my dick. She was still in her dress, and I had the best angle ever looking at her cleavage straight down the top of her dress.

"I saw you looking at them earlier" She said, smiling. She pulled the top of her summer dress down so that her tits fell out of the top. They were absolutely perfect tits. I grabbed one with my hand as she held my cock up to her mouth and put my head in her mouth. She sucked really slowly, working from the base of my head all the way down to almost the base of my cock. I let out a loud moan and I could tell she was smiling with my cock in her mouth. She worked my head and shaft perfectly with her mouth, and tugged at my balls with her hand.

I pushed my hips up in motion with her sucking. Lucky for me, my bedroom mirror was right behind her. Her dress was still hiked up and I had a perfect view of her bent over ass and pussy. She was small enough where I could grab her ass as she sucked me and it made my view even better. There was no way I was going to last very long. I felt the pressure start to build and I told her I was close.

"Good" she said as she took her mouth off my cock and moved her tits right above my throbbing dick. She pumped my cock hard and within seconds my cock was pulsing and erupting cum all over her tits as she said "fuck yes". It was a really intense orgasm. I was loud. When it ended her tits were dripping with cum and so was my whole groin area.

I went limp post-orgasm. It was a huge release and felt so good. But it wasn't over. She moved up closer to me and straddled me. She grabbed my still somewhat hard cock and held it upright, slipping it into her pussy. Her cum covered tits were hanging right in my face. I think she knew it was going to take a minute or two for me to get fully hard again, so she sat all the way down on my cock and gently moved her hips back and forth.

She asked me again if I liked what just happened and I of course said fuck yes again

"Good. I've always wanted to make a guy cum twice" she said as she continued to rock her hips back and forth. She pulled her dress up and all the way off. Some of my cum dripped off her tits while she did and landed on my check and neck. She leaned forward and sucked on my neck, cleaning some of my cum off of me.

My cock got hard again just from her saying that and I started to thrust my hips under her, showing her that I was ready again. Her pussy grinded on the base of my cock so easily since my whole groin area was already wet from my cum, and probably more so now from her wet pussy. I grabbed her ass with both hands and started fucking her really hard. She moaned and whispered in my ear "fuck me as hard as you can".

I slammed my cock into her as hard as I possibly could and pulled on her ass. She put her hands on the wall behind me and told me to fuck her even harder. Her tits were bouncing right above my face, and every few seconds a drop or two of cum would hit my face. I thought that was hot as fuck. I told her I was close again.

"Good, cum inside me daddy" she replied.

"Are you sure?" I said, not sure if she was cool with that.

"Fuck yes, cum in me!" she said again. I pulled her ass down onto my cock hard, pushed my hips forward and felt my cock explode in her. She grinded her hips hard on me as I came. It felt like her pussy was squeezing every last drop out of me. She could tell I had cum, and looked down at me with a smile.

"Looks like some of your cum ended up on your face" she said as she leaned down and licked my cheek and ear clean. She then leaned back and laid down on her back so that her head was on the opposite side of the bed. Her legs laid wide open with her pussy sitting right in front of my cock. She let out a sigh as I watched my cum drip out of her pussy.

There's more to the story but this is a good place to cut it off. She didn't end up going to the concert though, she ended up staying the night at my place and met up with her friends in the morning. I'll write the rest another time.