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My First Threesome

"Brad hooks up with an FWB couple"

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Author's Notes

"90% True."

Craigslist was a hookup treasure chest of opportunity back in the early 2000s. Personal ads from men and women were freely listed for No Strings Attached (NSA) hookups. Remember, this was before today’s many dating apps.

I had placed a few ads and replied to a few as well and did pretty well, hooking up with various women in my area. I was very careful, however. I used a fake name, had a secret Yahoo email, and never sent a clear photo of myself since I was still married. I loved my wife, but due to two bouts of cancer, we had a nearly sexless relationship. Maybe two times a month, and even then it was a fifteen-minute robotic quickie from start to finish. There was no passion and zero intimacy on my wife's part.

One ad read, 'FWB Couple seeking a straight male third for afternoon delight. WF 40, WM 43.' That was the entire ad. I took a chance and sent a short reply.

A couple of days later I received a reply from the guy. He told me that he and his “cum slut” FWB were both married, they worked together and would hook up every Thursday afternoon at a local hotel. He said he wanted to meet me to screen me first, then we’d meet at the hotel the following week.

I wasn’t wild about jumping through the hoop of a first meeting, but figured, What the hell, why not?

I met Ken at a restaurant bar. We talked, shared a few hookup stories over a couple of beers, and traded phone numbers so we could text.

The following Wednesday, he texted, indicating he wanted to talk to me, and gave me a specific time frame to call him. Later that night I learned the scenario for the next day. His cum slut had a fantasy of being tied up and blindfolded. She, Jill, and Ken are having a sex session and at some point, another man sneaks into the room and the two men pleasure her together and take turns with her.

I learned that they were into some kinky shit: handcuffs, leg spreaders, floggers, ball gag, big black dildos, butt plugs, etc., etc. Ken made it clear that at no point would she see my face; she’d wear the blindfold the entire time. He only had one rule: I must wear a condom when I fucked her.

As he paused, I asked, “What are the ground rules? What CAN’T I do?”

“No rules other than the condom,” Ken said.

**

I arrived at the hotel at the scheduled time and texted Ken. About two minutes later he sent back the room number. As he opened the door he put his finger to his lips, indicating that I needed to be quiet. He whispered, “Follow me into the bathroom.”

Once in the bathroom, with the door closed and the loud fan whirling, he told me that she was primed with a wet pussy as he’d be eating her for the past half hour.

I went back into the room and got naked. I looked at Jill on the bed and found her tied-down spread-eagle style. She had a blindfold over her eyes. On the nightstand, there was a bottle of lube, condoms, a couple of dildos, handcuffs, and nipple clamps.

Ken returned to eating her pussy, so I figured I’d start with a few simple kisses, letting her know I had arrived. I moved to her large saggy tits next. Jill was a BBW with a big belly and big floppy-looking tits, and not a woman I would have fucked had I seen her photo beforehand. As I sucked on her tits she moaned.

Ken tapped me on the arm and pointed to her pussy as he stood up. I walked over and looked at her small, trimmed bush. She was really wet and had an unpleasant odor. I thought to myself, there is no way I’m licking that nasty dark cunt, so I fingered her for a bit as he sat down at the small table and took a big gulp from his can of Budweiser.

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As I surveyed the situation, I decided this was not the experience I had in mind for my first threesome. I figured, Get a blowjob, bust your nut, and go home.

I climbed on the bed and straddled Jill’s shoulders. She had a couple of pillows behind her back and neck and was sitting up a bit as if watching tv. I’m sure she knew what was about to happen but kept her mouth closed, so I slapped my hard cock on her lips.

Jill opened her mouth, and I slowly slid my dick between her bright red lips. As I slid back and out, she said, “That is a nice cock.” I pushed it between her lips and went all the way into her mouth and stopped. After a few seconds, I thrust hard into her mouth, causing her to gag.

Ken told her, “Your new lover has a nice six-inch cock with a big mushroom head. As you probably know, she’s shaved clean too. He wants you to suck his balls.”

Jill shook her head up and down and tried to say, “OK” with my manhood in her mouth. I pulled out and leaned forward so she could lick and suck on my ball sack. She had a magic tongue as she licked and flicked my boys. I moved again and put my dick in her mouth.

I began slowly going in and out of her mouth. Again, she knew what to do with her tongue, and she’d place it against my shaft. When I was all the way in she’d stick out her tongue and slightly lick my balls.

Now remember, Ken had said I could not talk to her, so I moaned softly, letting her know I was enjoying her oral skills. The longer I went, the better it felt. I was lucky if I got a twenty-second blowjob from my wife half of the time we’d have sex.

My hips started moving faster and faster. I knew I was close to orgasm, and I thought about pulling out to cum on her tits, but I was worried I’d get her or the sheets dirty with jizz. I was not breathing heavily and had my hands up against the wall behind Jill and was face fucking her throat. She had to know I was close.

As my first large load exploded from my manhood, I let out a primal grunt. “AAGGHH!” I had buried my dick in the back of her mouth and another gusher of spunk painted her throat.

At this point, somehow, Jill was able to spit out my cock and started yelling, “I don’t swallow! God damn it, Ken! Untie me!” She was pissed.

As I jumped off of her and the bed, I noticed more of my man milk on her chin and upper chest. “I was told only no anal,” I pleaded as Ken removed the blindfold.

“No anal and no cumming in my mouth,” she said sternly.

I apologized and Ken took the blame, admitting he forgot to tell me about cumming in her mouth. As he finished releasing her legs Jill sat up on the edge of the bed. “I’m sorry, it was just such a surprise.”

“Really?” I asked. “I was going so fast and breathing heavily.”

“Ken always cums on my tits, so that is what I expected,” Jill said.

He passed out beers from his ice chest and the three of us talked for about fifteen minutes about Craigslist, our random hookups, and their FWB situation.

I quickly hit the bathroom, washed my face and cock, and got dressed. As I was leaving, Jill said, “But you didn’t even fuck me. I want that cock.”

I looked at Ken, “We’ll have to set something up in a month or so.”

About five weeks later I received a text from Ken, Same place, same time, same day.

I replied, Found my own cum slut. Have fun with Jill.

The End.

Published 
Written by Taco4x4
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