Teacher Conference

by Sandy

What’s your gender? Woman
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Teacher
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Wife and mom
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? 0

Teacher Conference

How long ago did this hookup happen? 1 month

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

How would you best classify this hookup? Group 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? They were two male teachers of African American descent. The first time we met was that night at a teacher conference. There were groups of teachers hanging out at a round table after the conference was over.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Everyone in the group headed back to their respective rooms after a while. We were the last three people on the elevator. They invited me back to theirs for a nightcap. It was still early and so I accepted. I wasn’t expecting anything except a nice, fun weekend away from the kids and hubby. There were no plans to hookup from either myself or them, I don’t think.

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 made the drunken mistake of talking about the whole big black cock stereotypes. They offered to provide evidence. Both of them whipped out their cocks, they were huge and extremely thick too. I was shocked. I couldn’t believe how big they were. I started giving them handjobs to begin. This led to blowjob on the one who was thinner and easier to blow. I tried oral on the other thicker one with little success. I was wearing a modest dress. The thicker one pulled my panties off while I was sucking his friend and he began fingering me. Soon I was naked, and the thinner one was eating me out to orgasm. When he stopped eating me out, he started having full intercourse with me, while the thicker one straddled my chest and I jerked him off onto my breasts. It was a huge load. While other was having sex with me, the thicker one recovered and I gave him oral and handjob. I made decision to straddle the thicker one and ride him later on. It took a lot of effort to accept his size. Unbeknownst to me, the thinner one found lube and wanted to penetrate my anus at same time. I hadn’t done anal in maybe 10+ years. Both men were penetrating me simultaneously, and it was extremely satisfying. I had 2 more orgasms and both of them climaxed inside me. I didn’t stay the night and left soon after.

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 met for breakfast in the hotel the next morning. I reminded them I was married and not to tell anyone. They didn’t know my last name but knew where I taught. I felt very guilty; my husband adores me and treats me well. I don’t think I want to hook up again, but the sex was best I’ve ever had. I even squirted which I didn’t know I could do.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, I don’t know if my partner was on any (other) method, I was fixed after last child.

What were your motives for this hookup? Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Somewhat

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? Somewhat

Why do you regret this hookup? I cheated on my husband with two male strangers at once.  He is a great dad and husband and I feel terrible and slutty.

What was the BEST thing about this hookup? The sex was absolutely incredible. I’ve never had so many orgasms during sex. The size of their penises were huge.

What was the WORST thing about this hookup? I cheated and didn’t even use protection. I did get tested though and was luckily still clean.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I still feel guilty. I can’t get the size of their penises and quality of sex out of my mind.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? Cheating is terrible.

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 would like to confess to my husband as I think he might be okay with it. He’s encouraged a threesome before, but with him participating.

What do you think about the Casual Sex Project? Writing this makes me feel better because I get to tell someone and get it off my chest.

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