Getting A Special

by The Bad Guy

What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? STL
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Office Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 25
How many hookup stories have you here posted before? 3

Getting A Special

How long ago did this hookup happen? Five years

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Paid sex

How long did you know the person before this hookup? Just met that day

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? Attractive blonde. 5’8. Perfect body type to me – thin, soft/untoned, large breasts proportional to her body, round ass. Sweet round face, big blue doe eyes. I did not know her at all, ran across ad on CL. I met at her place at 1 am.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My family was out of town for a week to visit in-laws, I stayed home for work. About halfway through the trip, I got “peckish” and it was the weekend. I spent an afternoon at work scrolling through CL ads and reaching out. I set up a meeting with this provider for 10 pm. I showered and prepared myself, making sure not to have anything of much value with me. When I went in search of her place it was hard to find and she was supposed to meet me outside. She didn’t come out. Trying to contact her was difficult. I spent hours driving, parking, texting, waiting. If I had been smarter I’d have gone home but I wasn’t doing the thinking. Finally, we connected, I was directed to her place and she met me at the door. She was very warm, greeting me with a hug.

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 led me upstairs to her apartment. She was wearing tight jeans shorts and during the climb up the stairs I stared at her ass. When we got in her place it was dark except for a nightlight in the kitchen and the glow of a tv coming around a corner from a living room. I could tell someone was in there. But she led me to her room and closed the door quickly. It was sparsely decorated. Big soft bed, unremarkable furniture, bare walls. She politely asked about a gift and I handed it to her. She sat it on her nightstand and turned to me with a grin. At that point, I could tell she was tired or high, not entirely there. Wasting no time she stripped out of her shorts, panties, and tight tee shirt (no bra). I undressed as well. When we were both nude we embraced and she started kissing my neck and stroking me. My hands explored her breasts and ass. When I was hard enough she got on her knees and started going down on me. I had been with a few different providers specifically for oral sex and most have been adequate. She was amazing. Deep long strokes, a lot of saliva, no gag. At one point she told me to hold her head and use it…so I gripped the back of her head and around her neck and fucked her mouth.

At this point, I’ll mention that when we arranged things I came over for a 30 minute bj. I had only ever been with providers for oral sex thinking I minimized risks and I love oral. Things were perfect.

After a few minutes of face fucking her as she played with herself, she stopped me during a break and stood up. She walked over to the bed and bent over. We weren’t going to fuck. I didn’t have a condom and she didn’t get one. I also didn’t think about it. I positioned myself behind her and took her. I was aggressive after oral, so I went harder than normal. She kept playing with herself and got very loud. I could feel her legs tremble in front of mine as the rest of her body convulsed with some gaspy moans. I assume she came, but given its paid sex it could have been performative. I stopped after her seeming climax and she climbed up on the bed and got on her back. As I joined her she was already spreading for me. As I entered again I asked how she wanted me to finish. I’m snipped and given how far this had gone I hoped she would say I her. But she told me to pull and cum on her. By this point, I was really worked up and couldn’t believe what was going on. The rest of sex was very quick. I put myself inside her and then pinned her arms above her head. I slowly plunged in her with deep strokes, again wishing I could fill her. As I held her biceps I looked her deep in the eyes. Her face scrunched in a believable throw of enjoyment. I watched her breasts bounce as I thrust until I wanted to hold them. She kept her arms above her head when I had let go. When I came I pulled out and stroked it over as much of her as I could. She had streaks from her navel, to her breasts, chin, and cheek, even in her hair.

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? Once I finished I climbed off the bed and got dressed in my shirt and shorts. She got up slowly and stretched once she was off the bed. I blatantly watched as cum dripped down her body – off her tits onto her thigh, glazing her abs and parts of her face. She remarked that it was a lot with a laugh but didn’t quickly try and clean off. I sat back on the bed as she eventually wiped some off before putting her shorts (sans panties) and top on. Slipping on her sandals she opened her door and ushered me down the stairs. I saw whoever was in the living room, a guy, getting something in the fridge. When we were outside, she gave me another hug and let me fondle her one last time. Not one thing was said about my gift versus what we had agreed and what had happened. It’s run through my mind a long time. Was she high and forgot? Did she just get horny? Did I fuck up some etiquette thing I don’t know about? But she was very laid back. She instigated the sex, without protection. I think if I had just cum without asking she wouldn’t have cared. Who was the guy? Roommate, pimp, extremely laid back boyfriend?

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Sterilization, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), I was feeling lonely, Boredom

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? I don’t know

What substances did your partner(s) consume? I don’t know, she could have just been tired. But she seemed high in some respect.

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? A friend I talk to occasionally and this.

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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? I cheated on my wife.

I caught myself up in the minute so much I didn’t really think about having had unprotected sex with a provider I wasn’t familiar with. I was uncomfortable and nervous until I got tested.

What was the BEST thing about this hookup? She was amazing. Oral sex, bending her over, missionary, taking a cum shot….it was all perfect.

The fact that we had planned oral but she wanted to fuck.

What was the WORST thing about this hookup? Guilt and fear over STDs.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s put a crimp in my experiences with providers. I KNOW what happened is not the norm and I NEVER expect that again. But the experiences obviously don’t compare. Plus she was the best at oral I’ve experienced I this manner.

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? In case anyone is wondering, the next time I got peckish I tried to reach out. It was after CL/BP shut down. Her number didn’t work form years before so I couldn’t find her.

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