What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? Bay Area
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? DBA
What’s your sexual orientation? Heterosexual

Dare And Prank

How long ago did this hookup happen? Last week

How would you best classify this hookup? Dare & prank

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? The female (F) and I have been FWB for a couple of years. She’s petite but with nice big C breasts. She has a very pretty face with an HWP sexy body. She is 5’1 & 110 lb. Over the years, we’ve done threesomes, with another man. I’ve pranked her several times when we meet for sex. She really enjoys threesomes that I’ve arranged and my pranks because it adds an extra thrill to our sex and she trusts that I’d do it only in a safe manner.

The male (M) in this incident is a good friend. M is tall, dark, and handsome. Not quite AF model level, but close. However, M is quiet and has a shy personality, especially towards females. However, I know M is just as horny as most men and he’d be happy to fuck if a woman is proactive enough with him.

F and M have never met and they don’t know each other. When I showed M the photos of F, M was very envious of me having such an attractive female as my FWB. This is when my prank was inspired.

I ask M to act like a stranger who happened to sit at a coffee bar in the hotel lobby where F and I meet up. Then, I’ll casually ask F to check out M to see if F thinks M is good looking and whether F would fuck M. If F likes what she sees, I’ll then dare F to try picking M up for a quick fuck.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On the day of meet up with F, I got the room first. I told M to sit and sip coffee at the coffee bar in the hotel lobby but I instructed him not to look at F and me. When F arrived, I told F that I needed some coffee drinks first. F and I sat at a nearby table and I intentionally let F sit in a chair so she could see M directly. After some chats, I pretended to notice M and I asked F if she thinks M was good looking. And I started to talk sexual and probe F’s take on M.

When the timing was right, I dared F to go & flirt with M. F didn’t take my dare and she just said that she’s never the one who initiates a flirt with a guy so she wouldn’t know what to say. I asked F if M comes over and flirt with her, would she consider sleeping with M. She replied that she’d do it since M is tall, dark & handsome.

So I proposed my next dare to F that I’d go over to chat up with M and ask M to come to F. To my surprise, F also rejected my dare.

By then, I’ve already sensed that F’s sexual interest in M is actually quite high. So I made another dare to F. I took out the room card, wrote the room number on the card. I told F to walk over to M, say nothing and smile. Then, slide him the room card and just head to the room.

F thought about my last dare for a few seconds and decided to do it. She went over to M, gave him the room card and head back to the room. Once F was in the elevator, M walked over to me and I told him that I’d wait in the lobby.

A bit over an hour later, M came down to me and gave me a thumb up. And it was my turn to hurry to the room.

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? When I entered the room, F was lying in bed under a blanket with a full smile on her face. I pulled the blanket off and she was fully naked. I got naked, jumped on the bed, pulled F’s legs far apart to expose her pussy, which was clearly wet & sloppy. (There is a puddle of wetness on the sheet.)

As I fingered her pussy, I suspected there was cum inside. I asked F if M came inside her. F replied “yes…twice”. A sudden feeling of jealousy shot through my mind because F has always been very adamant about condom use. But I just laughed and joked that handsome men get to do more with women.

F tried to explain that she was really nervous as soon as M came knocking. M took her by surprise because M was fast & furious in getting her naked and she didn’t have much time to react. By the time she realized, M’s hard cock was already inside her pumping away. And F said that his bare hard cock felt so good that she didn’t want to ask him to put on a condom.

F’s description of what happened with M was got me really horny. And I decided to slip my cock into F’s sloppy pussy without using a condom. I stared into F and told her that she’s getting two men’s cum inside her whether she likes it or not. F didn’t object and just started moaning, much louder than usual, as I fucked her hard to secretly vent my jealous feelings.

It only took a couple of minutes for me to shoot my load inside F. I lied next to her and asked her more details on how M and her fucked. After about 15 minutes of hearing that, I was hard again and I fucked F bareback again.

As I was fucking F for the 2nd time, someone knocked on the room door. I acted very surprised and F was truly surprised. I already knew it was M because that’s our plan. I kept up the prank and took a look through the peephole. I went back to tell F that M was at the door. Probably wanting to have another fuck.

F was somewhat nervous and didn’t know what to do. I offered that I’d hide in the closet and F just needs to get rid of M fast. Without F agreeing, I grabbed my cloth and went into the closet.

F went to open the door & tried to get rid of M. But, M insisted on coming into the room (as M and I planned). As soon as M came into the room, he got naked again. I could hear F trying to tell M in a worried tone that she has no time for more sex with him.

Of course, M didn’t budge and he continued to bend F onto the bed, took her panties off, and semi coerced F to start fucking from behind her. As soon as I hear M and F were having sex again, I quietly opened the closet door and slip out into the room. Initially, F didn’t notice me because she was facing away from me.

I walked up next to M, tabbed his shoulder, and waved him to step aside. As soon as he pulled out of F, I rammed my hard cock right into F’s pussy. That’s when F felt something was off and she turned her head to look. Both M and I busted out laughing hard. F realized it has always been a prank and she also started laughing hard.

After we three settled down form laughing about the whole prank, we all went into the extreme horny mode and we spent the next 2 hours doing a real threesome. M and I fucked F in almost every imaginable threesome position like DP, DVP, spit roast, etc. We both came another two times in F’s pussy & anus because F doesn’t like cum in her mouth.

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? Since the prank, M, F and I have done a few more threesomes. Furthermore, M and F have also met & fucked several times without me because I couldn’t go to make it a get-together. F is really fond of both M and me that F is willing to let M and I fuck her whenever and wherever. Furthermore, F has decided to go on pills so that M and I can fuck her without using condoms.

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