I’m back: Sex With My Boss’s Daughter

Some of you might remember me. I posted under a different ironman name up until recently. I deleted my account, because it got hacked. Some of the stories I posted over the last couple of years are gone forever from reddit, so I figured I would come back and start posting some old ones to make sure they aren't lost. I will post new stories as well when I have a chance. Here is an old one. Hope you enjoy:

Like I've said in previous posts. I figured it would be fun to go back to my promiscuous (man-whore) days and recall some of the stories from back then. I'm generally considered a really good-looking guy (used to model, 6’3”, dark hair, blue eyes, swimmers build, workout regularly), so that enabled me to have quite a fun sex life. These stories are 100% true and not embellished in any way. I think that a straight honest story even if not as exciting at times is a bigger turn on, so that is what I will continue to try to give.

I worked for a guy who had his own construction company for a while in college to make some extra money. The job was a pain in the ass, but I liked the guys that I worked with. We worked really hard, but would often hangout after work and have a few beers. Most of the guys were older than me. A few guys were in their 30’s, a few in their 40’s, and two other guys in their 20’s. The guy who owned the company was in his 40’s and had a wife and two kids. He was a pretty nice guy, but could be a dick at times. I think he meant well though and it was just kind of his way of trying to motivate people.

He would try to do little parties throughout the year for all of the guys where he would invite us over to his house and we would cookout and drink and just have a good time. I think he did this to build camaraderie between everyone and just show his appreciation for us. He had an amazing house in a really nice area of the city. The parties were always a really good time and we would often get really drunk by the end of the night. We would usually end up sitting around his fire pit telling stories and cracking jokes. His family was always there, but at some point in the night would usually head inside. I think he encouraged them to since he knew things would likely get more vulgar and rowdy the drunker we got.

His wife was extremely nice and was good looking for her age. I always imagined that she was probably smoking hot when she was in her 20’s. He had two daughters; one was 12 when I first started working for him and the other was 17. It always felt a little creepy, but the 17 year old was smoking hot. All of the guys recognized this and would give each other looks like, “fuck, how is that girl 17?” and just shake our heads trying to remove the dirty thoughts we were all thinking. She was the typical high school cheerleader and seemed like she was kind of wild. My boss would occasionally express frustration and we would hear stories about her getting in trouble for coming home too late or getting drunk etc. I always tried to steer clear of her at the parties, because I didn’t want to tempt myself and also didn’t want to give my boss the impression at all that I was trying to hit on his daughter. As we were around more she would try to involve herself in our conversations. Her dad would allow it, but would often ask her to go grab some food item or drink or something from inside to distract her and keep her away from the guys. I’m sure he was aware of how attractive his daughter was and didn’t enjoy the thought of all of his workers ogling her, but what could he do really.

I had been working for him for about a year and a half and another party was coming up. I was one of the first people to arrive and my boss asked me if I could walk into the backyard and grab some wood from behind his storage building for the fire pit. I head into the backyard and see his daughter standing out there moving some chairs around. She is 18 now and still obviously ridiculously hot. I say hello and head back to the storage building. She asked where I was going and I told her. She said, “I want to come.” Like I mentioned previously, I always felt awkward talking to her since I didn’t want my boss to get the wrong idea, but I said, “okay cool.” I will add now that over this year and a half I would catch her staring at me at the parties. I had only spoken with her in groups of other people though for the most part.

So, back to where we were, she jogs over and walks alongside me. I asked her how her weekend was going and she said, “Ehh, I’ve had better. My dad is kind of pissed at me.” I asked why and she said, “I stayed out too late last night and he freaked out. He is always pissed at me though, so whatever. He’d probably be pissed that I’m walking with you right now.” I kind of laughed and said, “really? Why?” She said, “he thinks I’m like some drug crazed sex maniac or something, so he probably thinks I’ll try to have sex with you or something.” I just kind of laughed uncomfortably and started having visions of her dad running outside and beating me to death.

We grabbed some wood and started walking back up towards the house. While we were walking she asked me if I had a girlfriend. I was obviously beyond uncomfortable at this point. I told her no that I did not. She said, “that’s hard to believe.” I just kind of laughed and didn’t respond, which I normally would if I were trying to get in a girl’s pants. I could tell she noticed how uncomfortable she was making me and I could tell she liked it.

People started arriving and the party got started. The whole night she was staring at me and would smile. I really hoped her dad wouldn’t notice and I don’t think he ever did. She was far more aggressive about involving herself in conversations I was in that night as well. The night was winding down and I was about to head out.

I walked inside the house and his daughter (Becca) was in the kitchen. She looked amazing and had on short jean shorts and a tight t-shirt (physical description: 5’6” super fit (cheerleader), really full C cup tits, nice toned athletic ass, face was a little like Rachel Bilson feature wise). No one else was around. She asked if I was leaving. I said yes and she said a playful, “nooo you can’t.” I said I really needed to and she asked where I was going, I told her I was headed home. She responded, “cool, I’m just going to do drugs and have sex the rest of the night” and laughed. She was obviously joking, at least I think haha. Either way I chuckled and left.

The next month there was another party and I won’t lie I intentionally showed up early hoping to have some more alone time with Becca. I couldn’t stop thinking about her and fantasizing about her. I didn’t want to cross any lines with my boss, but liked toying with the ideas. I arrive and my boss isn’t even there, but his wife and daughters were. He had run to the store to pick up a few things.

I walked out into the backyard and Becca followed. I asked her what she had been up to and she said not much, because she had been grounded for a couple of weeks. I asked what for and she said her dad found a condom in her room. Apparently it wasn’t a used one, but one in the wrapper that a guy had dropped and it was under her bed. I kind of laughed and said, “So he was right about you being a sex and drug maniac huh?” She just kind of laughed and said, “well maybe a little” and winked at me. She knew that I was interested in her and she also knew that I was conflicted. I quickly got uncomfortable again knowing her dad would be home soon. She continued toying with me, she asked when the last time I had sex was. I said, “ummm I don’t know if we should be talking like this.” She leaned in and said, “what’s wrong you scared of my dad?” and kind of laughed. I said, “yeah kind of.” She then decided to go off the deep end and really fuck with me she said, “have you thought about me before?” I again said, “we shouldn’t be talking like this.” She responded, “I bet you have. I have. I’ve thought about you doing all kinds of things to me.” She is saying all of this in a slightly joking tone, but also obviously serious. That’s when I decide to head inside and away from the situation.

I am beyond flustered and can’t stop thinking about having my way with her. Everyone arrives for the party and things get rolling. The tension between Becca and me was ridiculous that night. I tried everything I could to avoid being near her or looking at her. She did just the opposite and tried to make me as uncomfortable as she could. At one point I headed inside to use the bathroom that was down kind of a long hallway. I guess Becca followed me a minute or so after I went inside, because as I opened the bathroom door she was standing there and pushed me back in and locked the door. I said, “what the fuck are you doing? Someone is going to come to the door.” She just grabbed me and kissed me and as much as I wanted to resist I couldn’t help myself and we started making out. This lasted for about 20 seconds before my anxiety kicked back in and I said, “we should get out of here.” Then she pulls her shirt and bra up revealing her beautiful huge tits. I am in awe and just stop for a moment staring at them. I take them in my hands and caress her nipples. She closes her eyes and gasps a little. I tell her we have to get out of the bathroom and I slip out the door. Thankfully no one saw anything and everything was cool.

I couldn’t stop thinking about what happened after I headed back outside. I guess she really was sex crazed and holy shit it was awesome. I kept thinking my boss could tell something happened, but I was just being paranoid. Becca joined the party again at some point and we couldn’t take our eyes off of each other the entire time. She headed inside later on that night and about an hour later it was time for me to leave. Apparently she was watching from her bedroom window for when I was going to leave, because I headed through the house and out the front door and she was standing on the porch. I asked her what she was doing and she said, “let’s go.” I said, “what? What do you mean let’s go?” She said, “I’m going with you.” I said, Hell no you aren’t your dad will kill me if he finds out.” She said, “he won’t know I told my mom earlier that I was going to my friends house to stay the night. She thought I left like an hour ago.” I was ecstatic, but didn’t want to show it.

We ran and got in my car and headed to my place. She was beyond aggressive during the car ride. She was kissing up and down my neck and was whispering in my ear, “I want you to do anything you want to me.” I honestly couldn’t tell if she was always like this or if she was just that into me or if it was a combination of both. I said, “anything huh?” She said, “yeah anything.” She started rubbing my cock from outside my jeans as she kissed me. It took everything in my power to stay focused on the road. We got to my place and we start making out as we are walking through the door. I quickly take her shirt off and reach around unsnapping her bra. She takes my shirt off as well and we press our bodies against each other feeling bare skin on bare skin. I push her up against the wall and kiss down her neck and her chest and lick and suck on her nipples. She kind of had a high-pitched moan that she would let out and would say, “oh my god that feels good.” I pulled her shorts and panties down in one motion. She had the most beautiful soft skin, perfectly shaved, and such an amazing body.

I decided that since I was the “older guy” and she was so young I wanted be in control. I pushed her down to her knees and dropped my pants and underwear. She flashed a smile like she was glad I was controlling her. She seemed like she definitely knew what she was doing. She teased my cock, first licking and sucking on my balls and even licking back between my balls and my ass. She did this for a minute or so and then took my cock in her mouth and tried her hardest to take it all back in her throat. She took it all, but about an inch before she gagged slightly. She gave up trying to deep throat it and began sucking intensely. I couldn’t help but think about how this was the girl that everyone in her school probably fantasizes about. I was a late bloomer, so I definitely never got this kind of girl in high school. It was awesome having the opportunity now.

She sucked my cock for a few minutes before I led her back to my bedroom. She got on my bed and lay on her back. I began licking her thighs up and down and kissing beside and around her pussy, teasing her. She finally blurted out, “oh god, please just do it.” I gave in and started licking her clit furiously while I fucked her with my fingers. As I was fingering her one of my fingers was right up against her asshole. I remembered she said that I could do anything I wanted to her, but didn’t know if she truly meant it. In the moment I didn’t give a fuck I was in control and I was going to go for it. I slid one of my fingers in her ass while I was fingering her pussy and licking her clit. She didn’t miss a beat and let out a louder moan, but definitely not one of displeasure. It continues to get more intense and I eventually had three fingers in her pussy and two in her ass and she is screaming and moaning like crazy. I asked her, “do you want me to fuck you?” and she said, “yes, please fuck me.” I continued to withhold and just kept fucking her with my fingers. After a couple of minutes I gave in and grabbed her and flipped her over. I pushed her up onto all fours and licked her ass and pussy from behind to make her even more wet. I slid my cock in her from behind and started pounding her hard. She had me slow down for a minute, because she said it was too intense. I slid my finger in her ass while I was slowly fucking her from behind and she started saying, “oh fuck yeah baby.” This girl was way crazier in bed than any 18 year old I had ever known. I think part of her pleasure was knowing that her dad would want to kill her and me if he knew what was going on.

After a while I flipped her back over and put her legs over my shoulders and started fucking her with every ounce of energy I had. I don’t know why I was so worried about it, but I really wanted her to leave impressed with me. I think some of it was still the whole desire to be cool in high school thing. She was playing with her clit while I was fucking her and she had a really intense orgasm and shook until she had me stop for a minute. I took this opportunity to take things up a notch. She gave me the green light earlier to do anything I wanted, so I wanted to take advantage of it. I reminded her, “you said I could do anything I want. I want to fuck you in the ass.” She kind of smirked and asked if I had any vodka.

I went and grabbed some and she took a few swigs of it. I guess she needed some alcohol motivation to take the potential pain. I had lube that my previous girlfriend left at my place. I went and grabbed it and spread lube on her ass. I began sliding my fingers in and out until I had three fingers in her ass. She seemed to be really enjoying it and saying, “do you like that baby?” I think she knew how fucking ridiculously hot she looked in that moment. I got behind her and pressed my cock against her asshole. I pushed and the head of my cock was in. She let out a scream of pain and started breathing heavily. I was worried she was going to tell me she couldn’t do it. She said, “just wait and go slow you are really big.” I waited a few moments just savoring the amazing view and feeling of her ass clenched tight around my cock. I slowly start pushing in further. She is more relaxed and lets me start to slide in and out with small strokes. I eventually go as deep as I can, which still left about 3 inches of my cock to go. I start going faster and faster and she is moaning loudly with pleasure and saying, “oh yeah fuck me baby fuck me.” I only held out for about 3 or 4 minutes of fucking her ass before it was all just too much and too fucking hot and I started unloading my cum in her ass. She began moaning wildly when she felt my warm cum inside of her. I pulled my cock out and a little bit of cum dribbled out of her ass.

She lay down beside me and kept kissing me and kissing my face and neck. Somehow in that moment I could tell that she actually really had some sort of emotional attachment to me. She was being very sweet and lovey. It really took me by surprise. She slept at my place that night and I dropped her off down the street from her house the next morning. Her dad never found out about that. She became obsessed with me after that night though. She would call me every day and showed up at my place unannounced quite a few times. I’ll admit I didn’t discourage it, but I was surprised by how aggressive she was. She really wanted us to date, but I was always really worried my boss would find out. We had sex probably 20 times after that first night. We hung out for a few months, but she eventually went off to college and was a cheerleader at a major university. She still texts me and emails me to this day. We had another fling a couple of years later when she was in town, but that has been the extent of things.

Also, if you are a female and live near me you should send me a message. Might be a long shot, but would be cool/interesting to have sex with someone that enjoys my stories and then becomes a story haha

Source: reddit.com/r/gonewildstories/comments/3llpoe/im_back_sex_with_my_bosss_daughter