Cougar Rock Show Pickup, Busted While House-Sitting



What’s your gender? Man
How old are you? 30’s
What continent do you live on? North America
What country and/or city do you live in? Austin
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? None

Cougar Rock Show Pickup, Busted While House-Sitting

How long ago did this hookup happen? 4 years

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a week

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? Let’s call her Miss L. L is about a foot shorter than me, thin, and in great shape, with the Austin cookie-skin tan, short hair, and thick glasses. She’s cute, chipper, and perky like a squirrel with the extra flair of glasses and loving music. We both were there for a particularly famous classic sideman player’s residency. She was in her early 40’s. I was in my late 20’s.

She crashed into a conversation with a friend of mine and a few other acquaintances. I’m still not sure how it happened. It felt natural, but she had a plan which she told me about later. She was with a friend of hers but dug me all night long – my tone of voice, my apparent boldness and the pleasant way I am with everyone, period. So, she came over to me and said hi and started talking to me, asking questions and just talking about the night. It was genuine and I dug it. She said she wanted to sing with me, and gave me her number. I literally thought that’s what she wanted to do. I’m a sweetheart. I had just had a break in my then long-term relationship (2 years) and wasn’t looking for a hookup. I had never actually hooked up or had anything casual before Miss L.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I called her and we met up to hang out more. She came over to my place, wanting to take one car, and also she just straight up told me when she came over after a little talk – jumping me on the sofa in the process – that, yeah, she didn’t want to sing, though I was hot, and that she specifically had a thing for young guys, and we could take it from there if I dug her. She hopped off, a bit red-cheeked leaving me a bit stunned. We hung out for the day and went to her place, too, and also got hot and heavy on her bed, but she stopped short. Her housemate was there and the walls were thin. It was also only about 7 pm or so.

Two days later, she told me that she was housesitting for a friend of hers and that he wouldn’t be back until tomorrow. We found out he had a mirror on the ceiling of his bed. We got super stoned and hung out a bit. She initiated the rubbing and petting. All of the grinding and groping led to ‘are you ready?’, and she had prepared lingerie underneath what she was wearing.

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? She started and loved to vocalize everything that was going on. She also knew how she got off and led me straight to it. She was a clit lover. Grind the clit, beat the clit, fuck her hard but make sure you bang against her clit hard. She said, “keep my legs together and pull them up and do what you want – but bang me hard on my clit.” It was hot and also hilarious. I dug it. We went twice. We both came at least once even though we were super stoned, and decided to crash the night and leave the next morning.

We woke up early and decided to have one more good fuck fest now that we had learned a lot about each other the previous night. We decided to do it on her housesitter’s bed since the mirror was there. A good 20 minutes into it, the front door opens. We were definitely being loud. It was obvious that he (the guy whose house it was) heard us and was being quiet on entry. We stopped, and then he said “Hey L, you need a few minutes?” We both froze, and she said, “I’m going to go freak him out!” – she grabbed a towel, wrapped herself in it, and leaned out of the door and replied to him, face to face, with her face red from cumming hard and embarassment. His reply? “Awesome! This is kind of exactly what I would hope would happen! Nice one, Miss L!”. We both showered. I said hi and bye on my way out. I can tell that he cracked this huge smile when he saw me – keep in mind, I’m about 15 years younger than her.

We hooked up twice after, but honestly, the physical sex wasn’t all that good. We dipped a little bareback after we both talked about being tested and clean. Overall, the whole initial chemistry didn’t truly follow through to the act.

How sexually satisfying was this hookup? A little

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 stayed in touch as friends/acquaintances afterward. She wanted to talk to me about a future pickup or two she did, and I dug the lurid details and also being her past fuck friend that was ‘different’ in many ways. I think not being just a horny fucker and being present and a person from the get go ended up having her want to talk to me about herself. She ended up finding her love of her life not but a year later. She made it a small point to run into me and introduce him to me. Full circle closure.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Exchanged recent STI test results

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, I was feeling lonely, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Marijuana, hashish

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Marijuana, hashish

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

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? Never told anyone any details. I ended up getting back with my ex after the fling. She got some details, since she wanted to know, and that propelled us into another year and a half relationship of rocky fuck-fests that got her wondering about an open relationship. We never did finish working all that out, and we broke up.

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

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? Somewhat

Why do you regret this hookup? She lied to me at first. That was why I was stunned. I didn’t like that but it doesn’t matter. Getting caught is a hilarious story to tell, but it wasn’t particularly exhilarating. I would have liked to cum instead.

I siked myself up a little bit for the whole thing. That was probably an indicator that the sex wasn’t going to be unhinged and great. The chemistry either flows or it doesn’t, really. So, I just end up having long term relationships with fucking-off-the-WALL bombastic sex. This was the one casual thing I had, and it was blah.

Now that I’m happy, in a relationship, and actually married, I totally want to have no frills casual sex – WITH my soul partner – with some likeminded fucking turned-on folks.

What was the BEST thing about this hookup? In retrospect, funny as shit. Clit-banger. Mirror on the ceiling.

What was the WORST thing about this hookup? Time and effort and the regrets mentioned above.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? If I’m siking myself up for something, I’m not being true to the vibes. Be real.

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

All things considered, how NEGATIVE was this experience? A little negative

What do you think about the Casual Sex Project? This site is fantastic. Hoping that I can play with my soul partner with others. Eye opening to a wide variety of stories. Taking notes on how a lot of people are just fucking risky and wild, which is honestly a bit fucking frightening.

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