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

With Dad’s Boss

How long ago did this hookup happen? a month ago

What was your relationship status at the time? Same as current status

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

How long did you know the person before this hookup? For 1 to 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 tall, 58 years old with a  slim & fit body. He has a firm ass & looks sexy in his uniform. He’s got an arrogant attitude and has been divorced a few times. I’ve hooked up him before, but not since his recent marriage. His current wife is 28 years old and is 6 months pregnant.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Lately, my dad was getting irritated easily, but he never opens up to me. After a long day of golf, my dad and his friends came over to watch baseball and have some dinner. I overheard dad say he was past due for a promotion and that he thought his boss was being forced to promote someone from another division. However, when I entered the room with refills, things went quiet.

Two days later, I took my dad to the airport wearing a short white sundress & yellow sandal heels. Once dad’s flight left, I sent his boss a text to meet me at the food court. I asked if my dad was up for a promotion. He admitted ‘YES’ but he was forced to consider 4 other people and unless he could do some ‘heavy’ convincing, the job would go to someone from the DC division. I placed my hand on his and told him I was willing to ‘do anything’ to make sure he gets that promotion. With his sexy evil grin, he placed his hand on my knee and the flirting began. It’d been a year since we last hooked-up and I know what he likes. He began squirming and adjusting his crotch. I said, “Since your wife’s pregnant, I bet it’s been a while.” He quickly replied, “It’s been too damn long.” I said, “You could go home to your pregnant wife, rub her feet then rub yourself off, or we can meet up and we could be rubbing together.” (I know that sounded silly but it’s the only thing I could think of) With a confident tone, he said, “Sounds tempting. What did you have in mind?” I said, “I’ll let you do anything you want.” He said, “anything?” I mouthed, “anything”. He said, “Can you meet me this afternoon?” I winked and said, “I was hoping you’d say that.” He asked me to spend the night while using an app to reserve a hotel room and we’d have dinner together too. He’d text me the room number when he checked in. I listened as he called his wife and told her he had to fill in on a flight and would be home the next day.

I ran errands for dad, dropped off & picked up suits at the cleaners, then went home. I packed my large purse I use for hotel hook-ups, shorts, flip-flops, & a tank top to wear home the next morning, & bikini if a hot tub’s available. I cleaned the house & ironed a dress. I got his text, put on my ‘go to’ LBD with red heels and left.

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? I arrived at his room and I wasted no time. I got on my knees, pulled down his pants, and gave him a sloppy bj. His cock is smooth, thin, long, well-groomed, and was already hard. He was enjoying as I started I slobbering. He grabbed my head and forced me down on him till I started gagging. (he likes that & I do too! lol) My eyes were watering as he gave my bj skills a compliment then unzipped my dress. He put on a condom and bent me over the bed. He’s tall, so I left my heels on so it’d be more comfortable for both of us. He grabbed my hips and rammed himself inside me. I was so wet so he went in easily with one motion and began with an aggressive pace that was hitting my spot and making me cum. I could feel an orgasm building. It’d been a few weeks since I’d been fucked this damn good. I couldn’t hold back any longer. I had an intense orgasm AND he knew it because I was pulling sheets and pounding on the mattress. WHEW! We both giggled. He gave my ass a smack as I kicked off my heels and we moved on the bed. He got on top and pounded me until he got off. We talked and kissed as I played with his cock. He got semi-hard then I spun around and gave him a foot job. He enjoyed. I started with cowgirl then switched to missionary until we both got off again.

We went to the hotel restaurant and I held his hand on the way. We requested a booth so I could sit next to him. He placed his hand on my leg and I held his other hand. I told our waiter we were on our honeymoon and he gave us a slice of cheesecake for dessert. We took turns feeding each other and the moment was HOT! Back in the room, we sat outside on the balcony and talked. He had a few drinks from the mini bar and I smoked a joint a friend had given me. I was relaxed & horny, &  I started sucking him. I pulled him inside and bent over so he could fuck me from behind. He started fast & hard, but then slowed and I felt his finger enter my ass.

He began pressing the head of his cock in my ass. It was dry and the pain was so bad I could see stars. I squirmed and said ‘ouch!’. The last thing I wanted was to buzzkill the moment. I was afraid he’d think I was a stuck up bitch, but the pain was bad. I felt comfortable with him, he’s not thick and I promised he could do anything. I don’t like anal because my first and only experience didn’t go well and I was totally embarrassed afterward. It happened after a strange party with my ex-bf. We were at his apartment and the experience is too weird to share. Afterward, I was freaking out in the bathroom thinking this was the break-up moment and he’d never want to see me again, but he was so cool, just like he was with everything. He was respectful and never tried it again. Sorry to ramble.

I turned around and said, “I’m cool with anal but it’s been a long time for me. Would you be willing to use lube, promise to go slow & easy and stop if I tap out?” He said yes. We both agreed a condom wasn’t necessary. In a polite way, I told him a few boundaries. NO cross over and NO blow job for the rest of the night. I got lube from my purse and went to the bathroom to prep (I know, TMI). I applied so much it was running down my leg. I rubbed some on his cock and laid on my stomach. Thankfully, the pot still had me feeling relaxed. It was slick and took him a few tries. He entered and went slow. It was a weird feeling but it didn’t hurt. I felt his wet balls press against my ass and I knew he was ‘all in’. He paused and asked how I was doing. Surprisingly, it didn’t hurt so I told him to continue slow. He began a slow and easy pace. It was feeling good so I raised up to my knees. His cock slid in easy this time and our bodies found a good rhythm. He held my hips and picked up the pace with long slow strokes. It felt good and I began grinding my ass against him. After a few minutes, he pulled me tight and unload warm cum inside me. It was a lot. I made the awkward run to the bathroom. Thankfully, the bathroom fan was loud enough to cover up the embarrassing sounds (I know, TMI). I turned on the shower and he surprised me by getting in with me. We kissed as I washed his cock. We went to bed naked and kissed until we fell asleep.

I woke up expecting my ass to be sore, but it wasn’t. He looked sexy in bed and I was turned on waking up next to him so I did a ‘good morning blow job’. We were out of condoms so he made a trip to the hotel store. We had amazing passionate sex and I had two orgasms! Then we went to a coffee shop for breakfast and I left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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? We’ve hooked up a few more times, no anal, just quick hook-ups. His wife is very pregnant and he asked if I’d be willing to hook-up after she gives birth too. I was flattered and told him I’d meet up with him anytime.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant, No condom for anal

What were your motives for this hookup? Material rewards (gifts, money, drinks, dinner…)

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? Very

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.
She thought it was a hot story and inspiring because I was confident and bold to approach my dad’s boss, agree to have sex with him so my dad could get a promotion. She said she would have done the same thing. She’s a great friend and I value her opinion on everything. She gave me a few tips and different positions to try during anal. She told me, with the right partner, it gets better with practice. She’s crazy and the queen of anal. LOL

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

Did you get emotionally hurt as a result of this hookup? A little bit

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? Getting to hook-up with him again. He is amazing!
Waking up next to him. Getting to experience and enjoy anal sex & nothing weird happened.

What was the WORST thing about this hookup? We can only have a physical relationship. He’s an amazing guy and I’d love to wake-up every morning beside him.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve always been open with having sex and trying new things with different people. I wish more people would try.

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

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

Anything else you want to add about this hookup? I’d be willing to do anal with him again, but the moment and timing must be similar. Not in a hurry and when I’m relaxed. I enjoy regular sex a lot! For now, I don’t plan on doing anal very often or with anyone else.

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? I wish society would view having casual sex as being a part of a regular friendship. Beck and I believe it shouldn’t be shameful for women to approach a guy first and ask to hook-up, but society thinks otherwise.

What do you think about the Casual Sex Project? It’s nice to read other people’s experiences. I think there are more people having casual sex but they don’t have a good BFF to share the story with. This is a great place to anonymously share stories.

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