The Envelope

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His girlfriend has a threesome with a wealthy couple.
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"You are a lucky guy, let me tell you..."

I couldn't help but feel uneasy as Chester laid back in the beach chair in front of me, sipping his drink as he pushed his sunglasses against his face. I looked at my watch. I had only been there for a few minutes, and I already wanted to leave. It was one thing to be in the presence of a wealthy couple, but it was completely uncomfortable to be in the presence of a couple that had just fucked my beautiful girlfriend the night before. I stared at the envelope. It was all there. All twelve-hundred. I cringed as I thought about it, so I took another drink. Chester and Susan stayed in their seat as we glazed outside by their swimming pool.

"Is she coming?" I asked, trying to push things forward. I wanted the entire situation to be over with as soon as possible. Chester and Susan were friends of a couple of friends of ours. They were attractive, charismatic, and wildly popular. People basically bowed to them, as had I in a sense. They met Alyssa one afternoon without me and were immediately smitten. Their friendship with her bloomed very quickly and they soon revealed to her that they had been looking into finding a participant to help them in "rekindling" their bedroom behavior. She was their choice. Although I thought she was immediately sketchy about the situation, Alyssa admitted later that it both excited and flattered her, but she told them that she couldn't do it because she had a boyfriend. Then they came to me. At the time, I was a little strapped for cash, and a little confused by the entire offer. They asked for Alyssa for one night...sexually. They told me that she was against it solely because of me, therefore they maturely decided that they would ask me for permission. In addition, they offered $1200 and any favors down the road from either of them, including a job at Chester's father's company. I said no.

Alyssa and I had been together for 5 years. Our relationship had been all over the map. The incident that always stuck in my mind however, had occurred just three months into our relationship, when I regretfully cheated on her with my ex-girlfriend. The incident was completely circumstantial: My ex had come over because she was having personal problems. She was vulnerable, Alyssa had just moved away a month before and our "long distance phase" was beginning, and the situation took a hold of both of us. To apologize and show my devoted love to her, I moved to where she was living and after a few months, we were back together and solid. Unfortunately, my guilt never truly subsided despite Alyssa's constant forgiveness and undying love toward me. Although she never said it directly, I could tell that in a way, this experience would make us even in a sense.

Alyssa and I talked about it for days, finally deciding that it would be okay. Then, along with the pitted fear in my stomach, came the excitement. Alyssa had never had a threesome before. She had been promiscuous in her youth as well as with me, but in addition to never being with more than one person at a time, she hadn't been with anyone except me for 5 years. My own thoughts were kicking back and forth between discomfort toward the situation to extreme excitement at the thought of not just another man, but a girl touching my girlfriend's soft flesh.

Alyssa met with them the night before, giving me just a quick peck before I dropped her off at their gorgeous mansion. I paced for the rest of the evening, drank a little, tried to watch some TV, and eventually decided that it was no use worrying; I went to sleep. When I awoke, I drove to their place once again to pick her up, which led me to the current moment.

"She's still asleep," Susan smiled. I half-smiled in response, upset that I had to spend any more time with them. I wanted my girlfriend back. I wanted to know how she was. Was she crying in the bathroom? Had she been fucked like never before? I shifted as the questions crossed my mind.

"Do you need another drink?" Chester asked. "I know it's kind of early, but it might calm you down while we're waiting for her."

"Yeah, sure..." I accepted. Susan got out of her chair to fetch another drink.

"Sandwiches too, darling," Chester added. He watched as his wife walked away, then he shot a look to me accompanied by a smile. "Man to man, now that she's away, that little Alyssa is one hot thing."

I continued to squirm at his words. His cock had been inside her just hours before I arrived. "Yeah," I agreed, blocking out visions of the attractive man pounding into my girlfriend's gorgeous pussy.

"I mean it. She, Susan, and I fucked the night away in ways I will never forget. I just wanted to thank you for the opportunity."

"Anytime," I blushed.

"You mean that?" Chester asked, excited.

"No, it was just an expression," I told him quickly, unaware of what I had instinctually said. We sat in silence for a couple of seconds. I could tell on his face that he had been left completely satisfied by the experience. "She's okay, right?"

"Alyssa!? She's fine! Oh I assure you, she's fine! I told you we'd take care of her last night and we did."

"Did she...have a good time?"

"Darling, we all did," Susan responded, placing a platter of sandwiches on the glass patio table. "If you don't mind me asking, where did your Alyssa learn to eat pussy like a professional?"

My heart skipped a beat. I stammered for the words until I finally found them. "She had a roommate in college who she used to experiment with. Right before I met her."

"Well they must have really gotten into it sometimes," Susan giggled. "I remember this one point where...you don't mind if we talk about it a little, right Bret?"

I thought for a moment and with the excitement rushing to my cock at the thought of Alyssa eating Susan's blond pussy make me spit out a yes. I almost would have rather heard it from them than from Alyssa herself, who may not have even shared the experience with me. It was one of those experiences you had to know, but didn't necessarily want to. Nevertheless, they continued.

"I remember one point when Chester, you had your cock in her little hairless pussy from behind while she licked me clit wildly on the floor."

"Hairless!?" I asked. Alyssa's pussy wasn't hairless; it had a brown tuft that covered it perfectly.

"She suggested it!" Chester cried. "We had mentioned something about it and she suggested it, so we shaved her!"

"You should see her now, honey! Her pussy is so smooth."

"And believe me, fucking a bald pussy was more thrilling than I imagined."

"You fucked her?" I asked, knowing that he had, but I still couldn't quite grasp it.

"He did," Susan responded. "All of us fucked each other. Every which way. I want to thank you Bret, because before this, Chester and my sex life was basically switching from me him on top to me on top every other week. Adding Alyssa to the equation made us try so many things we had never done before."

"Mmm!" Chester blurted to Susan as he sipped his drink. "Anal! I finally found that I love anal. I never thought about it before, but when your legs were wrapped around Alyssa's head when we were in the bed and she was tonguing your pussy while I watched, she grabbed my cock, unable to see it..." "Not that someone needed to see to grab your cock last night," Susan teased. She turned to me. "It was huge. At least 7 inches last night, I've never seen it that big. And the way it dripped made me squirm like a little school girl, I'll tell you."

"She grabbed my cock and led it to her pussy, which I had already released a load into once before, and she led it to her asshole, her legs spread. She lifted her ass and then just began begging with it. It was one of the hottest things I have experienced in my entire life. She loves anal, doesn't she Bret? I can tell."

"She does," I shifted. He was right, though my imagination the night before hadn't done justice compared the stories I was hearing. I imagined Chester fucking his wife while Alyssa basically watched. I didn't really consider her being a very active participant. As they spoke, I became more comfortable with the situation, however. My cock was raging inside my shorts as I waited for more. I could feel the pre-cum seeping through the fabric.

"Are you sure you're okay with us talking about it?" Chester asked. "We can stop. I just figured we'd pass some time while we're waiting for her. She should be up any time, though I'm sure she's exhausted."

"No, it's fine!" I forced a smile. "It's fine. It's kind of relieving actually, to hear about it."

"He's getting turned on!" Susan sneered. "You little fox! You're getting turned on hearing about your hot little girlfriend's first threesome, aren't you? I bet your cock is hard in your shorts right now!"

"Leave him alone!" Chester chuckled. "I'm sorry about her. When she gets frisky, she lets go of all her inhibitions, including verbal."

"I do not!" Susan protested.

Chester's eyebrows rose. "You're kidding. Last night, the first time I was fucking you while Alyssa licked us, you were calling her everything from your bitch to your fuck-whore. Not to mention when she ate you out when you called her...what was it...your cum-licking-slut-fuck?" He turned back to me. "After I came into Susan the first time, Alyssa ate her out, eating all of the cum that dripped out of her pussy. It was all over her face: my cum and Susan's juices. And she had the biggest smile."

"So sexy," Susan moaned. "And she would scream like none-other!"

"As did you!" Chester cried. "Both of them screamed whenever they were being fucked. Sometimes at the same time. Imagine how hot it would be having your cock in this sexual little brown-haired, bald-pussied vixen that isn't yours. She's screaming like a banshee while she begs you to fuck harder and your wife is masturbating next to you, screaming that she's going to cum and that she wants to cum on the girls face."

"I did...and she drank every last drop."

I gasped at the thought. "Are you surprised?" Chester asked.

"No, I just...its interesting hearing about it..."

"Interesting? That's strange choice of wording. I'd consider sexy maybe," Susan teased with a smile. I could help but become turned on by her teasing, not to mention that she was a very attractive blond woman with large breasts and an erotically voluptuous body. I could almost see her with her husband's enlarged, dripping cock in her ass while my own girlfriend flicked Susan's clit with her tongue I shook the thought and brought myself back to reality.

"The hottest part of the night was fucking her ass, by far," Chester admitted. "So fucking tight, but she know exactly how to use it. I blame you for that, Bret. The way she controlled herself it was if she knew exactly when she wanted to make me cum. And she did. Cumming into Alyssa's ass what one of the most intense orgasms I've ever had. I had already cum thrice before during the night: once in my wife's pussy, once in both of their faces, and then once in your girlfriend. Even though this one should have been short and unsatisfying, inside Alyssa's puckered asshole, I came buckets. Her eyes went wide and she ate Susan until Susan juiced all over her face again."

"I thought I was going to drown her," Susan giggled. "But that wasn't the hottest part for me. Besides the numerous sixty-nines we had while you were rejuvenating..."

"Believe me, if you want to see something erotic, try watching my wife and your girlfriend eating each other's pussies. That rejuvenated me faster than I could ever imagine."

"I came four times just due to those sixty-nines over the course of the night. Ten times in all," Susan claimed proudly.

"How many times did Alyssa cum?" I asked, curious as my cock throbbed. Chester and Susan looked at each other.

"I'd say at least 10," she said. "At least. Maybe she was keeping count, but I know she came every time I hate her out and at least twice every time she was fucked. And once when I was fingering her. The hottest point in the night for me though was either when she ate the cum out of my pussy – which might I add, I did not expect, because that was very early in the evening – but I also loved when you came in her pussy and she had me eat it out. She fucked my face so hard while Chester fucked my pussy from behind. When I came I soaked the bed with my juices. I was swallowing his cum and then when she came, she started to squirt it into my mouth along with her juices. And she tastes so good, Bret. I still get wet thinking about it."

"She was an orgasm machine," Chester admitted. "It came to the point that when you touched her, she said she was going to cum."

"Well I'm glad she had a good time," I grunted.

"We made sure of it," Chester smiled. "She saved a sex life that we thought was beyond repair. And she's welcome back anytime. With your blessing, of course."

"As are you sometime, if you'd like, Bret," Susan added. "Chester's never had a cock in his ass."

"Honey!" Chester cried in embarrassment. "Nor do I intend to!"

"He does," Susan whispered to me with a giggle. "But first he has to take my ass...I was thinking tonight..."

"I'm a little sore," Chester laughed. "But if you insist."

"I mean it about joining the two of us, though," Susan said to me, biting her lip a little as she shifted in her seat. I couldn't help but feel extremely attracted to the woman who had just licked my girlfriend's pussy. Her tongue probably still tasted like Alyssa's wet crotch. "Even without Alyssa. I've never had two cocks before." Her hand was under the table, touching her clit. Chester watched her for a moment with a satisfied smile and then became preoccupied.

"Here comes your girl," he told me pushing the envelope toward me. I turned around and watched as Alyssa waved from the door, a smile on her face.

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ohioohioover 17 years ago
hoping for a sequel

This is a very sexy story. And there are so many places you can take it, beginning with Alyssa and Bret exploring their feelings about what happened--how it affects their relationship, and what they feel should happen next.

i hope you'll continue it!

ohio

AnonymousAnonymousover 18 years ago
Fantastic!

Really nicely done. Very hot and sexy, a nice new twist on a somewhat standard plot.

Very nicely done!

AnonymousAnonymousover 18 years ago
Indecent Proposal

I didn't think of it as a "hooker/pimp" story, but more of an Indecent Proposal scenario in which Robert Redford wants to give Woody Harrelson a million dollars for a night with Demi Moore. Not necessarily a pimp situation, but a proposal (as the title suggests).

As for the story, it was well done - a little fragmented, but the point was for it to be hot and it was. Continue it - I'm anxious to see where it goes

Jerry WalfellJerry Walfellover 18 years ago
NIce job

Appreciated the device of having the couple telling the boyfriend about their menage with his girlfriend. Although it wasn't terribly realistic, it was effective.

NiceGuysDontGetLaidNiceGuysDontGetLaidover 18 years ago
Please follow up with the girlfriends pov.

Why does he need a job? He already has one as a pimp. All he needs are serveral more whores and he can sit back. Being with a woman that would still have respect for a man that allowed that to happen would be a living hell.

Still well written although the subject needs much more writting to cover all the feelings created.

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