I Set Up and Let it Happen Pt. 01

Author's Note: This is my first submission. If people like this story, I will keep adding to it and turn it into a series. Thanks to Soma for editing and adding to this story.

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Looking back now, I would not have gone through with it that night. That night changed things between Kelsey and I forever. The night I'm referring to, of course, being the night my sweet innocent girlfriend had sex outside the relationship for the first time.

This is the part where I describe ourselves. Kelsey was a 21 year old blonde at the time. She has pretty greenish blue eyes to go with perfect DSL's (dick sucking lips). She is quite a sight at her small height, just about 5'4 standing wet. She could best be described as curvy. She is right in the sweet spot between petite and overweight. Those curves are never more apparent than in the fantastic posterior she carried. Yeah...she has a big fat ass and I, along with many others, can't keep my eyes off it. I at the time, was no slouch either. With my tall, athletic build, and handsome features, I had little problems attracting women. Together we had been dating nearly 2 years and had few lovers quarrels to mention.

I know what you're asking yourself, why, if things were going well, did I allow my curvy girlfriend to sleep with another man? My response- it had long been a fantasy of mine. The idea of watching my girlfriend getting fucked by another man turns me on like no other. Or at least, it did, before it happened. And then happened again and again and...more times than I could count (or know of). It was this fantasy that led me to staying up late at night and browsing cuckold erotica. Over time, my fantasy grew as I continued reading. I started egging Kelsey on to pose for suggestive and naked pictures-so that I in turn could post them online and jerk off to the nasty, degrading responses they received.

Kelsey, being the innocent and naive girl she was, had no idea strange men on the internet were getting to see her most intimate spots. If only she knew that men from all over the world were stroking their cocks to her and cumming to the thought.

After pushing this fantasy further and further towards reality, one day it took a huge leap. Inspired by an erotic story I had read about a man setting up his wife for a threesome, a plan to make this a reality took shape. From our dirty talk in bed and role playing, I knew what Kelsey would want in another man if she ever went for it. The speculations were pretty vague but gave me a good starting point. In fantasy, she wanted a man that was between 20-30, hung (or what she thought was hung), and white or black.

The plan stewed for a while until one night after a particularly nasty session in bed in which I was able to goad Kelsey into providing a graphic picture of what exactly she would want if she ever did it. Hearing the type of guy she had in mind made our roleplaying so much dirtier and hotter. With this information in hand now, a couple days later I mustered up the courage to pull the trigger and give her this fantasy for real.

The question then was where would I find her fantasy stud? None of our friends or acquaintances fit the bill and I couldn't ask them anyway. I couldn't just walk up to random people and ask. Which left me with Craigslist. Anonymous and filled with horny guys looking to fuck a girl, I knew I would have little trouble finding her fantasy man there.

The ad was brief, basically outlining the type of guy wanted and that only serious responses with pictures and bios would be considered. I made sure to include a beautiful picture of her ass before I posted it. At 10:27 that night I published it. By midnight I had received nearly 200 responses. I took that as a good sign.

After a day of looking through the responses I wasn't even half way. Deep down I wanted all of them to fuck Kelsey , but I knew to make this work I needed to find a guy she would be hot for. It was so hard trying to figure out what EXACTLY she would like, beyond the detail she had let slip. Between thinking about her ex boyfriends, things she had said during role play and what I wanted to see I needed more time. I called into work sick the next day.

With a full day to concentrate I narrowed the list down to five finalists. I had asked that they include at least one picture, and it was a bit disconcerting how much I enjoyed looking at these men's bodies. I tried to pretend it was just to make sure it made Kelsey happy but I hadn't totally convinced myself. After a few emails, I eliminated two of the guys, they seemed overly aggressive and didn't seem to understand the idea of what cuckolding really was. The last three all seemed like really strong candidates. I could not figure out how to decide, until it dawned on me, Kelsey deserved a monster cock. Mine was fine, but how could I ask her to fulfill this fantasy of mine if I wasn't going to give her a life changing piece of meat.

It took me almost an hour to figure out how to word the email asking strange men to send me pictures of their dicks. Eventually I just went with the straightforward explanation. I asked for one flaccid and one hard.

The feeling of seeing those email come up in my inbox was hard to explain. I had gotten nudes from girls before, but I was much more excited for these cocks. The first one would not do the job, it wasn't bigger than mine, and it didn't look that hard in the picture. The second guy was a possibility, his cock was definitely longer than mine, but maybe not as thick. Then Brandon's email showed up. His soft cock was longer then mine was when it was hard and the picture of it hard was breathtaking. It was at least 4 inches longer than mine, and it appeared you could drill holes in drywall with it. It was as thick as a beer bottle and had veins running up and down the length of it.

I pictured it slamming in and out of Kelsey's wet pussy, but without warning I also wondered if I could fit it into my mouth. After a moment to make myself believe that hadn't happened I emailed him back to set it up.

I informed him that he was the pick and told him the whole plan I had in mind. Brandon went from friendly and reserved in his emails to delighted and arrogant. Of course, he was playing the part but it made me anxious and admittedly, very hard. I shared more pictures of Kelsey and made sure he knew the details as we started texting. Condoms are a must, this would be a one time thing, and he would be respectful to whatever Kelsey told him.

The days went by like this as we continued to text and he became more and more dominant, making requests and so on. The requests started innocently enough, asking for more pictures of Kelsey but only got riskier from there. He would ask me to go through her closet and send him pictures of the various bras, lingerie, and panties she had. Another request (demand) he had was sending him pictures of my own cock.

After he got them he replied with two questions:

1- Are you sure you want to do this? She isn't going to want to have anything to do with your little twig after she gets an adult sized cock? I wasn't sure he was serious about this, but it made me feel pathetic that for a moment I really considered it.

2- When our girl sucks cock, where does she like the load to go? I assume you have hit puberty and are able to cum with your girl, but if you haven't I'll ask her directly, that would explain the size of your penis . At this point I should have hated him, mocking me about my dick, talking about cumming on my girlfriend, I should have called it off. Instead I went to the bedroom and furiously masturbated.

The days went by like this as we continued to text and he became more and more dominant, making requests and so on. The requests started innocently enough, asking for more pictures of Kelsey but only got riskier from there. He would ask me to go through her closet and send him pictures of the various bras, lingerie, and panties she had. Another request (demand) he had was sending him pictures of my own cock. He would reply to what I thought were good dick pics by joking about how small I looked and assuring me my girlfriend would love his humongous cock. He questioned whether Kelsey would even want me inside her after she got to feel a real cock. I honestly didn't know the answer to that question but I didn't want him to have the satisfaction. His final request before we picked the night was to purchase her a large dildo for her to unknowingly practice with before she tried his. Kelsey and I had toys that we occasionally played with while making love, but Brandon made it clear none of those would do. The 6" pink vibrator we had was already larger than my own penis but Brandon insisted I purchase a dildo that measured at least 9". When I brought it home, Kelsey instantly fell in love with it (as Brandon told me would happen) and asked for me to use it on her every time we had sex over the next couple of days.

Finally it was the Friday that we had chosen to be the night. I made sure to pamper Kelsey throughout the day, and into the evening. We went out to a nice dinner and had plenty of drinks. When we got back to the apartment, Kelsey was clearly tipsy and horny. She nearly pulled my clothes off getting through the door. As much as I wanted to take her right there, I knew I had to hold her off and work her up further. I went to the closet and pulled out a sexy lingerie set I had bought the day before (at Brandon's request). She was more than willing to please and went to the bathroom to change. I grabbed some more wine and poured it and came back to the sight of my girlfriend dressed in a black mesh bra, red lipstick, stripper makeup, stockings, heels, and the absolute tiniest g-string thong to top it all off. If I wasn't hard yet, that put the nail in the coffin.

Again, I could have called the thing off and taken Kelsey right then and there. Unfortunately, my inner cuckold kicked in and I instead asked her to lie back on the bed. I walked to the nightstand and texted Brandon to make sure he was here. Then I pulled out the dildo that I had recently bought. I got between her legs and pulled her tiny thong fabric to the side and used my other hand to rub the dildo along her slit. As I had predicted, the wine and pampering that day had already worked her up a bit and the dildo glided along with ease due to the wetness. I placed my tongue on her clit and licked away before she finally begged me to stop the teasing and fuck her with the dildo. Aiming it at her tight little hole, I rammed it to the hilt in one push. I rammed it in and out of her for the next ten minutes until she was ready. It was now or never. As I slam the massive dildo in and out of her wet hole she is panting and moaning louder than I have ever heard her before. It sounds like she is trying to say something but she might be drunker then I realized as her speech sounds slurred. It takes a moment but I finally figure out what she is murmuring.

"It's so much bigger, so much bigger, so much bigger." Over and over again.

It takes me a moment but I realize she is talking about how the dildo is bigger than my dick. At first I feel excited that she will want Brandon's cock, that this plan might really work.

"Ya baby, you like that big dildo? Does that fill your cunt up the way you want?" I'm starting to really get into the dirty talk.

"Yes, it's so nice to finally have my cunt feel full."

It takes me a minute to realize that my drunk girlfriend just admitted my cock didn't satisfy her. Everything seemed to slow down, like I was underwater. I felt terrible; Kelsey was the perfect girlfriend, so perfect that she had faked enjoying my dick for the last two years, never letting me feel inadequate.

I asked the question-the question I had asked so many times while we were roleplaying before. "Baby, imagine if this dildo was another guy. Do you want another guy to come in and fuck you like this?" I continued our typical roleplay as if nothing was different.

The only response I got was moans. The idea was obviously turning her on so I pushed further. "Do you want a man with a big cock like this to walk in and fuck you right now?" This time she looked me in the eyes and through her drunken, horny stupor, she said yes. "I want it Griffin, I want him to come in right now and give it to me. Oh baby, yessssss. I need a huge cock inside me."

That was it. I left the dildo all the way in her and walked out of the bedroom and to the door. Brandon, following my previous instructions, was there when I opened it smiling with a menacing grin. He had only a tee shirt and athletic shorts on, which I assumed were for quick access. "Take me to your girlfriend" was the only thing he said before I led him in and he followed me to the bedroom.

The walk seemed to last an hour although it really only took moments as I could feel my heart beating rapidly and my cock growing painfully hard. Then we were there, barely inside the bedroom and I saw Kelsey's eyes bulge when she learned we had a visitor. She was lying spread eagle in the center of the bed, covered only by her black mesh bra and the tiny g-string. She quickly covered herself with the blanket"Griff, who is he?? Why is there a strange man in our room??" Without saying anything, Brandon approached the side of the bed. "Baby, this is Brandon. He's here to make our fantasy come true."

With that, Brandon began removing his clothes as Kelsey looked on at me, dumbfounded. "No, no. Griffin it was just a fantasy. Just something we do in bed together. Seriously. We can't do this." "Kelsey, you just admitted you aren't satisfied with my dick, I want you to have this, you deserve it. Think of it as a present you can enjoy totally guilt free. We should be young and wild." It was then I saw her eyes move from me to Brandon until she saw the gigantic stick pointing through Brandon's briefs. She stopped arguing as she just stared in awe.

Brandon noticed her looking as well and moved in closer to the bed until his covered dick was standing just within Kelsey's reach. He reached his long muscular arm over and grabbed Kelsey's left breast through the bra. She pulled away, just a bit, but not totally out of his reach. Brandon continued to squeeze her breast and finally spoke. "Come on you slut. You want this. You can't take your eyes off of my cock. Go ahead. Pull it out and touch it."

Kelsey looked at me. "Griff, do you know him?"

"Ya, we have talked for a while, this is our chance for our little fantasy to come true. Let's do it babe."

I wasn't sure what she would do next. Just when I thought this had been a bad idea and about to fail, Kelsey bit her lip, looked quickly over at me, and reached out and grabbed Brandon's cock through his briefs. Even though I had hoped and planned for her to go through with it, it was still quite a shock to see her touch another man with my own eyes. It was that simple reach of her hand that began to bridge the gap between fantasy and reality.

"Go on Kelsey. Pull my cock out. See just how big it is for yourself. You're little boyfriend over there set this all up for you. He told me about how much he's wanted to watch another man with his girlfriend and how you've fantasized about experiencing a big cock for once."

Kelsey glanced over at me again, this time with a questioning look in her eyes as if to see what I would do about this. When she that I did nothing but watch what she was doing she turned back towards Brandon and used both hands to pull the briefs down. Brandon's cock instantly sprang up towards her face and both Kelsey and I let out a tiny gasp. I had seen a few pictures of Brandon's cock in his emails, but it was far more impressive in person. I had figured him to be 8 or 9 inches but in person I could see it had to be at least 10 inches, and thick too. A sudden tinge of jealousy washed over me and I began to question whether it had been a good idea to provide her with such a tremendous dick. Kelsey was in awe and wasted no time in further inspecting the monster. She brought her cute little face to the head and slipped just enough of her tongue out to taste the tip. She must have tasted something she liked, as she then held the tip with her hand and ran her tongue from the base of the cock up. "That's it slut, worship my cock. Show me how much you appreciate having a real cock to play with." Brandon took the back of her head and pushed her in slowly until his cock reached the back of her throat. Kelsey gagged, having never had anywhere near this much hard throbbing dick in her mouth. Her only practice over the last 2 years was on my smaller than average penis. Brandon sensed this as he started pulling her head into him again and again. "Mm, suck that cock Kelsey. You may have only had pencil dick over there to play with, but I can already tell you'll be a great cocksucker." Kelsey could only moan a response as she greedily tried to swallow Brandon's manhood. She looked like a starving dog getting its first food in days she tried to gobble every inch.

Hearing Brandon so blatantly insult my manhood should have infuriated me. Instead, my own cock ached to be touched and I began to rub it through my pants as I stood watching the scene unfold. Kelsey slowly worked into a rhythm as her face was continually impaled on the mammoth of a cock. It seemed to go on for ages and I had to stop touching myself so as to not cum too soon. Brandon finally let go of her head and pushed her to her back as he stepped out of his briefs and got into bed on top of her. He quickly made his way to her g-string and just tore it off in one motion. He inspected my girlfriend's pussy for a few moments before looking back towards me and saying, "Well. there's the proof right there. Griffin, come closer and look at your sweet girlfriend's pretty pussy. See that?" Brandon used his fingers to pull apart Kelsey's labia for me to see. "That is a tight pussy. I knew you were small but just look at that. You've barely stretched her at all." My cheeks grew red in embarrassment looking at how wet my girlfriend was and hearing Brandon's humiliating statement. Brandon laughed and made his way back up Kelsey before leaning down and locking her in a passionate kiss. They made out like lovers for a few minutes then I saw him whispering something to Kelsey and her whispering back. "Tell him" Brandon ordered her. Kelsey looked on to me standing at the foot of the bed and said something I will never forget. Kelsey looked me in the eyes sorrily and said, "I'm sorry baby, but it's true...sex with you is fine but a big cock is something I need. Please don't be mad."

Brandon laughed. "Mad? He loves this. Look at that wet spot in his pants. You want me to fuck your girlfriend, don't you bud?"

I tried to speak but no words would come out. Brandon positioned himself over Kelsey and pointed his cock at my girlfriend's tight pink pussy. "Answer cuck. Ask me to fuck your little girlfriend here like she wants. If you don't ask me right now, I'll stop and you can be the one to fuck Kelsey. But if that's not what you want, just say the word and I'll ruin her pussy for you forever."

This was the last moment to turn back. I could just tell him no and try to salvage the whole thing and pretend it never happened. If I asked him to push in instead, I would forever be a cuckold. I would have to go on knowing another man not only had his dick inside my own girlfriend's mouth, but he had placed his member in her most intimate of places and pleased her like I would never be able to.

Kelsey looked to me, almost saying "please" with her eyes. I should have said no and I nearly did. Instead, my own horniness and need to fulfill my sick fantasy completely took over. Somehow I pulled the following words out of my own deep submissiveness. "Brandon, please fuck my girlfriend. I know I can't give her what she needs and I want her to have the experience of a real cock, not just a small dick like I have."