The Bet The Maid

by Mykal

What’s your gender? Woman
How old are you? 33
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Denver, Colorado
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Business sales
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity?
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 1

The Bet The Maid

How long ago did this hookup happen? Last year’s Superbowl

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

How would you best classify this hookup? Short fling

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? Chad is tall 6’6″ tall, with a rugged yet smooth face, and piercing green eyes. He is funny, well built, strong and muscular. He is from South Africa and he is the manager of the country club were my husband works as a chef.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?  It started with a bet. I was going for the Rams along with my husband. Chad had placed a few bets and I told him to put me down for a small bet blindly. The Patriots were up, but I had faith and wanted to watch them lose. It was in our small talk that Chad made a joke of how his maid would be mad at the mess from the snack buffet. I was feel a little self conscious coming from a work conference to meet up with my husband and Chad. Most of the people had left by time I got there at half time. I was wearing a black, business casual skirt with three inch mary jane heels, thigh high stockings, and a buttoned blouse.

The game ended and I learned the sum of my blind bet was three grand. I began to freak out a little knowing I could only cover five hundred dollares. Chad said if I would be his maid for three months every Saturday than he would cover the other two thousand five hundred of my bet. All I had to do was clean like his maid already did. After discussing it with my husband, we decided it was the easiest thing to do.

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? It was late, almost midnight, and my husband had to work at 5 am. We had driven our own cars, so I was going to stay a little while and clean up after the party. I did not have to work the next day, so time was no bother in my case.
I gathered the dishes, rinsed them, and put them in the dishwasher. Then I swept the floors and vaccumed the living room. The whole time Chad and I made small talk. At the time, my husband and I were new to Denver, and his boss was fun to talk to. He paid me alot of attention and even gave me some compliments.

As our small talk ran on, Chad became flirtatious and complemented my body several times. I became a little flirty while I was dusting his living room. “I pay my maid extra…” Chad began to say with a stutter. Nervous, he stopped and found his voice. “I paid my maid for sex on Saturdays. It started with me watching her masterbate. I only get laid by her once a week,” Chad said while looking at me. He then told me his fantasy was to have me now.

I stood up as I let him undress me. He kissed down my body as he played with my pussy, fingering it. I sat on the couch as he kissed all over my body, stripping my clothes off. Sucking on my breasts and fingering my pussy, we sixty-nined on the couch. After a long while and a few orgasms later, Chad pulled his cock head out of my mouth and lined it up with my slit. He entered me and pounded my pussy. I was on the couch on my back and his arms were holding my legs open as he took deep hard thrusts into my pink slit. I rocked my hips back on his thrusts. We were kissing and he eventually came in my pussy. He kept fucking me and put me in doggy style and pouned me hard. About fifteen minutes later, he came again. I got dressed and left. I the drive home, I absent mindedly rubbed my clit, feeling his cum running out of me and into my underwear. I looked forward to my Saturday’s with Chad now.

Every week we had two or three hours of sex on tables, standing against the wall, in his pool, and even in his back yard. I miss it some days. It was a great sexual experience and Chad gave my husband a three dollar raise on his hourly pay.

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? After the hook up my husband and I stayed friends with Chad, still going over to his house.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Intoxication, Submission / Relinquishing power, Making new friends

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

What substances did you consume? Alcohol, 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, Marijuana, hashish

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

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? Somewhat

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 husband

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? A little bit

Why do you regret this hookup?

What was the BEST thing about this hookup? The intense secrect

What was the WORST thing about this hookup? The guilt

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really

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

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

Anything else you want to add about this hookup? No

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? In general it’s been a way to move my relationship to a slightly more open status.

What do you think about the Casual Sex Project? Its a good place to vent.

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