Previously on me fucking my boss’ daughter: The guy who owns the ad agency where I’m working is a dick. His daughter works out of the same office. She’s 32 and I’m 23. We go for wine one night and end up fucking in her car. The next night, we go over to her house and have sexual gymnastics for most of the evening. She tells me she’s never had an orgasm. I have a mission.
***
Basically, the experience in part 2 repeats itself for a few months from early spring into the middle of the summer. Dee (boss’ daughter) and I are each in relationships with other people closer to our respective ages but continue to hang out regularly, basically as FWBs.
One day, Dee messages me at the office and tells me she’s going to a “pure romance” party at a friend’s house that night. If you’re not familiar, it’s where one girl friend signs up to a brand rep for a sex toy company, hosts all-girl parties where they explain different sex toys and how to use them with the goal of selling you a sex toy.
That night, Dee is messaging me at the party (I’m still at the office working on a pitch): “Holy shit, I’ve unlocked my orgasm ability and it’s amazing.” She proceeds to tell me how she was at this party with a 5-6 women and they’re sharing their sexual hang-ups. Dee tells the group about the fact that she’s unsatisfied with her boyfriend, but fucking this 23 year old (me) feels so good that she feels this pressure like she has to pee, but never fully orgasms. The host sells her a smaller vibrator and Dee goes into the bathroom by herself. Through the door the host helps bring Dee to a full squirting orgasm in her own bathroom. Dee tells me the women on the other side of the door were cheering for her, and she’s embarrassed because this woman’s rug is now soaked in Dee’s cum. She’s messaging me all of this while I’m at work and I can no longer concentrate on what I’m doing. The final straw was her asking me “Can I show you? ;)” There was no more work done that evening. I went straight home and messaged for Dee to meet me there.
At the time, I was housesitting for my parents: their house was big, had a pool and a hot-tub and was very private. More importantly, it was only about 10 minutes from Dee’s house. I throw a bathing suit and go out back, turn on the hot-tub, crack a beer and begin rolling a joint. I see Dee’s headlights pull in and meet her at the gate that leads to the pool area. We hug and she’s got this excited smile on her face. She goes back to her car and grabs a black bikini and her purse. She changes in pool house and we hang out on a chaise lounge by the pool. I’m sitting upright facing her, we light the joint and pass it back and forth, sipping on beers.
*Sexy time begins here*
She’s retelling the story about her sex toy party and my cock is making its presence well-known in my bathing suit. Dee sees this and leans in to kiss me. We begin making out on the chaise. I relax into the back-rest and Dee straddles me. Without breaking our kiss, she unties her bikini bottoms and exposes her manicured bush: a perfect triangle. She throws them to the side and immediately begins untying my suit. No sooner is the knot undone than my cock springs out. She yanks my suit down to my knees and expertly guides my cock into her waiting pussy. She sinks her weight down on to me and moans into my mouth as we continue to kiss. i reach up and pull the knot on her top, which falls off to reveal her perfect b-cup tits and tiny, light nips. I lay back and guide her hips back and forth across mine, grinding her into me. I can already feel her warm juices flowing down my balls, and into my belly button. I can hear the soft drops of it seeping through the chaise material onto the pool deck below. She begins to ride me faster, now resting her hands on my knees and leaning back, giving me a phenomenal view of her tits and frame. She reaches over into her purse while i’m still in her and pulls out a small black pocket rocket and begins to run it all over her clit. I take it in my hand and guide it myself. I can feel her begin to tense around my cock as her moans grow louder and her pace quickens. Suddenly, she stands up off of me, pulls the vibrator away from her clit and proceeds to drench me in a torrent of lady-cum. Holy shit. What the fuck just happened? No sooner is this done than she’s back on top of me, riding me again. A few quick bounces back on my cock with the vibrator running all over her clit, and she does it again. It’s like someone is popping a water balloon of warm water over my cock and stomach each time. I grab her taut thighs the 3rd time, trying to keep her from coming back down on my cock because I’m about to cum. “Ahhhn!” she moans “it’s ok, it’s not my time of the month. You can come in me” I. fucking. lose it. Now my boss’ daughter, after drenching me in her own cum, wants me to cum insider of her (and I know she’s not on the pill). Fuck it. I pull her down onto me and proceed to unload a massive amount of cum deep into Dee’s pussy. She moans and leans forward into my glistening chest, panting. “God that feels good” she says. “I’ve wanted that for awhile”. “Me too” I manage to get out.
***
The hottest part might be that any time I’m at my parents’ house with my wife, she always sits in that chair and I always get a bit turned on thinking about what went down that warm summer night.
Next time, I’ll post about the time we went to a sex-store for more toys :)
Source: reddit.com/r/gonewildstories/comments/612gwi/part_3_boss_daughter_and_i_take_things_outdoors
Amazing story! I loved how she wanted to feel you finish in her mid-orgasm