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What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many hookup stories have you here posted before? 1

First MFM Threesome

How long ago did this hookup happen? 3 months

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

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? 38, MILF, cute face, chubby, enthusiastic and passionate.
My friend and I had never met her in person before. We had discussed earlier about going on a business trip together and informing our wives that we’d be out. This was arranged, three days of chilling out and bar hopping.
On the first day, my buddy told me he had this girl he’d been flirting with online and she happened to be available that day to meet up.
We had booked a two bedroom suite and believed it was a large enough space and safe environment in case one of us did something silly. We met the lady, she seemed okay, and joined us for a few drinks.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few hours in she wanted to go to the room. So my friend takes her and I get back to drinks and other company I met earlier.
Some time passed and I get a call from him asking to meet up in the room.
Reluctantly I agree and head over, wondering why he asked to hurry.
When I reached the room, I knocked on the door a few times before opening it with my card.
I enter the common area, and noticed the lady sitting on the sofa. I smile and asked where my buddy is. She said he’s gone out to get some things. (She did look a bit shy than before.)
I called my friend to ask why and I hear him enter the room with a few items in a bag.
He enters in bluntly asking me “need your help, you have experience in bondage…help me prepare her” I was a bit taken back, but was tipsy enough not to think too much into it.

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 asked her if she had done this before, to which she said no. So I told her to open the items my friend had brought and I shall slowly get them into it.
He had brought rope, a few vibrators and a whip, she agreed to be positioned in partially doggy style and bended over on the flipped chair.
While getting in her place, my friend went and put his cock in her mouth. As I was finishing up, her cunt was oozing out. I asked my friend to put his tool in before she burst out, and jokingly remarked “wish I’d get a thank you for my service?”
My friend at this time takes his cock out from her mouth and goes to her pussy to enter. The lady takes a breath in and as he enters asks if she can suck me.
I paused, already horny watching that oozing pussy, I asked my friend if I could and he replies only if we can tag team her.
So our night began. She was very obedient, as we moved her into different poses she was just begging to get her holes filled, which made both of us even more horny.
In the midst of it, we began doing it without a condom, the sensation on its own was even more thrilling, especially when she started giving remarks while we were doing her. Saying things like, I wonder who will get me pregnant, who can fill me up the most. We spent the whole next day romping.

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? A bit guilty

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

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? I don’t know

How wanted was this hookup for you at the time? Not at all

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? no-one

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? I felt guilty for cheating on my wife, and that too on a lady older and not of ideal shape.
Felt even worse when I found out she was still married.

What was the WORST thing about this hookup? Got interested in threesome 

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? found that older women are also open minded and have needs

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

Anything else you want to add about this hookup? She contacted us later for another round. I was reluctant to go especially without my friend, she contacted us again shortly after with a proposal neither my friend nor I could refuse.

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

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