First Time With Dad’s Boss

by Katie

What’s your gender? Woman
How old are you? 20
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Miami
Highest education received: Some college (currently in college)
What’s your occupation? student
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? free spirit
How many sexual partners have you had in your life (including oral sex)? >30

First Time With Dad’s Boss

How long ago did this hookup happen? 2 years ago

What was your relationship status at the time? In a relationship (open)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For more than 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? He’s been a friend of dad’s for as long as I can remember and has been my dad’s boss for over 5 years. He’s tall, in his mid 50’s, slim with a fit body, confident attitude and a major player.

I was 18 and it was the summer after I graduated HS. He was in the early stages of a divorce from wife #2 and didn’t have time to find his own place. My dad told him he could stay with us for a couple of weeks. His schedule is crazy like my dad’s, so he only needed a place to crash a few days a week and planned to find an apartment when his schedule rotated to the long break.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My friend Beck and I met some hot guys at the beach and got invited to a party. My bf, at the time, had to work, but he didn’t care if I hooked-up with a guy as long as I shared the details with him later. Beck couldn’t stay out too late cause she had plans with her bf the next day and agreed to drive so I could smoke pot. We went to my house to shower and change clothes. I put on a navy blue ribbed mini tank top dress with heels. Beck wore a pair of my denim shorts with a VERY tight tank top.

At the party, Beck and I held hands and gave each other a peck on the lips then went separate directions. As expected, Beck was getting checked out and a hot guy started talking to Beck. The guy I met at the beach took me outside to smoke pot. I smoked a couple of joints and got super horny. His hand was rubbing my leg and his thumb was rubbing my wet panties. He’d pulled them to the side and was rubbing my clit when I stuck my hand down his shorts. I could feel he was small, soft, not groomed, & had lots of hair (yikes!). I asked if there was a place we could go have sex, but he was nodding in and out. His breath smelt like smoke and alcohol. He admitted he’d been drinking all day. In his current state I knew it was going to be a lot of work for me to get him hard if we decided to fuck. Beck came outside and I told her I was ready to leave. Beck felt bad for needing to leave early because she thought I was having fun, but I told her what happened.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? At home, I heard a TV and I remembered Dad’s boss was staying with us. I had a slight buzz and was super horny when I went in the theater room. He was drinking beer and watching a game. I asked if he needed a refill or anything and loved the way he looked at me! I can’t explain why, but I got on my knees and pulled his cock out. It was long, thick, & semi-hard. I licked it up and down to get it wet. Then started sucking him. He got hard quickly. My panties were soaked and I wanted him to fuck me. I straddled him, pulled my panties to the side, and guided him in. He felt amazing entering me. He pulled my dress and bra off.

We kissed for the first time while I went up and down on his hard cock. His large muscular hands squeezed and pulled my ass open as his cock slid in and out. He picked me up, I wrapped my legs and arms around him, and he carried me to his room. He laid me on the bed, pulled my panties off, got on top, and started pounding. I was relaxed and fully submissive. He found my spot and was making me gush! I had a much needed orgasm. WHEW! He pulled out and unloaded a large warm load of thick sperm on my stomach. A few loads even landed on my tits. I remember telling him ‘wow! you came a lot!’ then I quickly ran to the shower. He went back to the theater room.
I got out of the shower and put on a loose tank top with shorts. I got him another beer then changed his sheets because of a large wet spot. LOL

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? The next morning, I made coffee & cut up fresh fruit. We had breakfast and talked. He started out saying he didn’t want my dad to know. I giggled and said ‘no worries our secret is safe.’ I told him I’m VERY willing to have sex with him as long as he stayed with us. We had sex many times the next few weeks.

He got an apartment on the first of the month, but I still met up with him anytime he messaged, mostly for booty calls. He loved my Mediterranean pasta salad, so I’d make a fresh one and we’d meet up after he’d traveled for work. We’d have dinner & sex. Mostly it was sex, dinner, then sex again. LOL

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Marijuana, hashish

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My BFF Beck of course. I tell her everything and she doesn’t judge. Also my BF at the time. He was so cool and enjoyed hearing details. My ex-bf’s favorite fetish was having sex with me soon after I’d had sex with someone. I was ok with it, but my ex-bf REALLY liked that so I’d go along with it.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Having sex and getting a much needed orgasm. Getting a new fuck buddy too!

What was the WORST thing about this hookup? He moved out a few weeks later. It was convenient to have sex with him when he lived with us. LOL

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve always been open to casual sex and I think people can enjoy having sex but still be friends too.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Age doesn’t matter when it comes to having good sex. I wish society was more open and accepting to casual sex.

What do you think about the Casual Sex Project? I love it! It’s a great place to read other people’s experiences.

You have a hookup story to share? Submit it here!