Boundary Pushed

by Jessie

What’s your gender? Woman
How old are you? 32
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? California
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10 – 20

Boundary Pushed

How long ago did this hookup happen? 4 years

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

How would you best classify this hookup? Group sex

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? My boyfriend and I have been together for 3 years prior to my very first 3some experience. The extra guy is 6’3, in excellent physical shape, handsome, and looks like one of the NBA athletes. I met him only briefly for a few minutes only once 2 months prior to the 3some. I thought he’s really good looking to a point that makes me feel nervous. My bf found the extra guy online and arranged the whole thing.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Prior to my very first 3some experience, 3some only crossed my mind a few times in my life. I’ve never thought about actually trying to make it real. My bf and I have done 3some a few times over the years after the very first 3some. He’s always the one who finds & arranges the extra guys. I just show up to enjoy it. It really excites him to see me being very slutty and promiscuous with strangers. By myself, I would have never done casual sex or anything close to what we’ve done together. I am too shy and risk-averse to have sex with a stranger by myself. My bf is my trust-worthy partner in crime and I’m adventurous to try anything sexual as long as he plans it. Once in a while, he likes to pushes my boundary and surprises me.

My very first 3some experience was the result of him pushing my boundaries. He told me it would be just a simulated 3some because all three of us would be fully clothed. The other guy would just cop a feel while my bf and I kiss.

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? After a few minutes of kissing, my bf stuck his hand underneath my skirt and found my dripping pussy already soaked through my panties. As he continued to kiss me passionately, he laid me down on my back and his hand pulled one of my legs high and wide to expose my crotch. I was both surprised and extremely aroused that my crotch was shown to a stranger in such a manner. The other guy needed no encouragement. He quickly dove between my legs to kiss my inner thighs and soon he was eating my dripping pussy. Soon after that, it turned into a full blow fast & furious 3some that gave me no time to think, react or resist. My bf only took off my panties. He and the other guy were switching quickly between fucking my pussy and my mouth. Then they put me on my hands and knees to pound me hard in doggie style. The other guy pulled out and splashed his hot cum on my butt chicks. My bf wasted no time and stuck his cock in me and pounded hard as well. Soon, he also pulled out and splattered all over my butt. The whole thing started and ended in under 15 minutes.

I didn’t have an orgasm but the whole experience was extremely unforgettable. Years later, I still masturbate while thinking about the details from that very first 3some.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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? I felt “sexually high” in the next few days. My bf and I had 3somes a few more times with the same guy within the next two years. Within the same period, my bf arranged a few other guys for 3somes with different play scenarios. Sometimes, I would just lie face down naked in bed waiting for a stranger. My bf would let a stranger into the room. Without seeing each other’s faces or saying anything to each other, the stranger would just get on the bed behind me, part my legs, and insert his cock into my wet pussy for a quickie fuck. Afterward, the stranger would leave immediately.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? Just my bf.

Do you regret this hookup? Not at all

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