The Cuckold (Hint: not me)

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MY FIRST DEVILS THREEWAY?

If you remember my second post, I talked about a very fun devils threeway. True, I had a complete blast BUT, that wasn’t the first, nor the last. My first one happened a couple years back with a couple that, not only did I know them, I was involved with their wedding.

Story time.

So Sarah has been a friend of mine since college. We had gotten to know each other during a few group working sessions and hit it off right away. I’m not going to lie, I had the biggest crush on her. Here is the crazy part, she isn’t Asian! She’s white! White with a niiiiiiiice ass. We did a dance class together later on in college and I always strategically placed myself behind her when she wore yoga pants. God damn. I could stare at that thing for days. Now, I never made a move on her since she had a boyfriend of at least 4 years. That sucked but she was just a good person to be around so I didn’t mind just being her friend. (Friendzone, I know). Her boyfriend was a weird but cool guy so I enjoyed my time with them. Their wedding, a few years later, was completely amazing and I couldn’t be happier for the two.

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Fast forward a couple years past that.

I found myself bored one day and decided to cruise craigslist. I had begun to have a curiosity in threesomes, primarily male-male-female (MMF). I would think to myself, well, why not try it? Don’t knock it until you’ve tried it? On craigslist there are a lot of older couples and some super hot ones, but of course, a lot of them are fake. On that day I decided to check it out, I found a gem. I saw a title that caught my attention: “Fake! Fake! Guy is collecting pictures!” Bored, and without any reason not to, I clicked the ad. Sure enough, there was Sarah and her husband. Apparently, the husband had posted on there looking for pictures. I was in shock! But, I was also a little excited. Could this actually be a chance for me and Sarah to fuck? I had to find out.

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Me: Hey! How have you been?

Sarah: Great! I’m on my way back from Vegas.

Me: That’s cool, ummm, kinda have something I want to tell you.

Sarah: ?????

Me: Some one is posting pictures of you and James saying that he’s collecting pictures of guys.

Sarah: OMG WHAT?! WHY WOULD SOMEONE SAY THAT?!

Fast forward a bit

Sarah: Sooo, I have a confession to make.

Me: ….yeah?

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Sarah: We actually did post on there. We were looking for another guy to fuck.

Me: Whoa, how did this come about?

Sarah: Have a drink with me and I’ll tell you about it.

We meet up the next week for happy hour and she explains the whole thing to me. A few months back, her husband had come out to her as bisexual. This completely destroyed her world and left her in a bit of a depression. A few weeks after that, James had expressed that he wanted to watch Sarah get fucked right in front of him. Total Cuckold situation. She explains to me that it took her a week before she “manned up” and wanted to fuck a new guy. BTW, they had been each others first and hadn’t been with anyone else since. Completely new situation for them. Sarah tells me more about it. She explains that it was weird at first because her husband sat in a chair on the side and just jerked off while watching her get fucked from behind. She was a little surprised since the guy fucking her started talking down to James…AND HE LOVED IT!

Cuckold.

We ended the happy hour with a surprise make out session. She tells me that she was texting for permission to fuck me and he said yes. I’m surprised because I had expected a kiss at least but not fucking. Did I say no though? Lol, noooo. We made our way back to my place where I got the pleasure of undressing her. My Lord, her body was just perfect. Amazing tits after I took off her bra. Slowly taking off her pants, I was fixated on her ass when she turned around. She had the perfect apple shaped ass that most guys crave.

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The sex was great but I want to get into the kinky stuff. Fast forward a few months after a couple pay dates with Sarah. James tells me that he feels left out from the sex and wants us all to play together. In other words, I can’t fuck Sarah unless James is around. This makes me nervous because I had always wanted to try a MMF but seemed to be getting stage fright at the possibility of it. Total guy thing, always willing to try something but gets scared leading up to it. Because James is Bi, I had a legitimate fear: what if he wanted to play with me instead? I’m not that way so I didn’t want to get into “kill mode” if I was going to be harassed. Explaining my hesitation to Sarah, she just laughs and says to come over that night anyway.

Oh fuck here we go.

I find my way to their place in a decently looking apartment complex. The street looks run down and the inside hallway is a bit out of a 70’s horror movie but Sarah answer the door with a big smile. She leans into me and gives me a kiss. “Relax. Come on in.” Obviously, I’m really nervous. The hallway leads to a T intersection where to the left is their bedroom, to the right is the living room. We turn right to reveal James sitting on a sofa chair, beer in hand, smile on face…

James: Hey! Come have a seat.

Me: (nervous laugh) heeh heh, oh boy. How are you James?

James: (laughing) I’m great! Thanks for coming over.

Me: Thanks for having me?

We begin to chat about TV shows like Workaholics. Sarah brings us some beers and we continue to chat. I’m sitting on the couch while she sits on James’s lap. A few episodes of Workaholics later…

Me: Sorry guys, I gotta use the restroom.

I get up and do my thing. After finishing my epic piss from three beers, in front of me stands Sarah, butt naked. She looks at me with a smile and walks back to her room. I immediately look at James, as if I need approval still. He looks at me with a creepy approving smile, and gives me a wink. Fuck, it’s on now.

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Keeping the door open, Sarah pins me against the edge of the bed and tells me to take off my cloths. Nervously, I do so. We get to making out. I’m very passionately grabbing her ass and pressing my cock against her stomach. Pushing me back on to the bed, Sarah grabs my cock like a stick shift in a car and sucks like there is no tomorrow.

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She was really into it, I felt my cock was being jerked with each sucking motion. I was holding back as much as possible. Drunk, and getting my cock sucked, I was starting to get into it. Feeling more of that explosion building up, I grab the back of her head and pull her off me. Kissing her passionately, I turn her back to where I was just laying and throw her back. Spreading her legs to expose a nicely shaved pussy. I start going to town on her.

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Using the tricks Yumi taught me, I was making Sarah squirm. Unbeknownst to me, in the dark room with the only light coming in was through the door way, her husband was standing there just rubbing is cock. I was wondering if he was rubbing himself to the naked image of me or that of his wife being pleasured…maybe both?

I HAD NO TIME TO THINK! BACK TO ACTION!

With each squirm, Sarah moved her hips up and down more violently. Keeping the method of sucking on her clit continuous became a challenge. And God damn was it hurting my jaw. I tried keeping her motionless with one hand on her pelvic bone, the other pinching her nipples. This effort proved worthless as she moved more violently and shoved my head off her in a massive squirm and screech. I’m now standing, gathering my composure when Sarah motions with her hips for me to fuck her. Not, wasting a second, I reach into my pants and grab a condom, while putting it on I turn back and look at her husband. I do this for a last chance for him to say no, but, alas, he just smiles at me in a devious way and gives me a nod. Weird? What would you do?

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I take that cue and slowly insert myself into his wife. I could just slam my cock into her but I want her to feel every inch, so, slowly, I move in. I know I’m bigger than her husband because she said she’s never been with a guy as big as me. Normally a huge compliment (pun intended) but she’s only been with three guys including me. Not much to compare, but hey, what guy will turn down a compliment of their penis size?

With her ass at the edge of the bed, I’m able to pull her legs to line up with my chest. She’s basically a 90 degree angle on the bed, just so you know. Hold onto the top of her thighs, I start fucking her hard. The contact between her ass and my hips make a rather loud slapping sound. With each slap, Sarah let’s out another moan. Enjoying myself, I keep fucking away. A few minutes into this, I look back and see Sarah’s husband without pants and still playing with himself. Only now he’s fully erect. He’s not jerking it hard, just more like slow stroke up and down. Given that I was the guest in their house, I wanted to give him a good show. I pulled out and, grabbing a thigh, throw Sarah around on her stomach. She looks back at me puzzled, I respond, “get on all fours and face your husband.” She complies without argument. I figured I should give him a show since he’s a great host.

I mount behind her froggy style and slip my cock into her wet pussy. God though, her ass looked amazing. Just how I love, her has cheeks spread apart naturally showing off her ass hole and pussy. Bracing myself on her hips, I start moving to get a good rhythm. I didn’t want to look direct at him, it’s still weird to have a guy jerking off and looking at you. Focusing on her and building momentum, I grab the back of her head by her hair, jerk it back and fuck her hard. Sarah let out a long yell, arched her back and slammed a hand into the bed. Ohhh yeah, she was into this.

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I feel the burning in my thigh grow to a level that I couldn’t manage, so I moved back to doggy style. Now I get more aggressive and fuck her violently. The momentum is picking up and the explosion is building faster than I expected. No chance for me to avoid this one. Time to let loose! I could feel my body seizing up, from the top of my head, this electric surge shoots through my body in pulsating motions. Sarah, noticing my sudden collapse on her back, smiles and tells me I did an amazing job, gets up and walks into the living room. Her husband, had disappeared.

I lay down and take a few moments to process everything that has happened. Did I really just fuck my friend while her husband beat off to it? Or to me??

I compose myself and walk into the living room with Sarah and her husband talking and laugh.

James: (Looking at his wife) did you have fun dear?

Sarah: Ohh yeah, I enjoyed his cock in me.

Me: (nervous laugh) I had fun as well!

James explains to me that watching his wife get fucked is one of the hottest things in the world. I don’t know if I could do that in my future, but hey, live your dream. We chat for a bit and I learn that he wants this to happen more often. Partched, I grab a glass of water and take my leave. Sarah and James tell me they’re going to go for round 2. Usually, the guy that fucks her is bi and takes his turn fucking James in front of his wife. Once again, not sure how they can do that but whatever.

Another story for the books? Fuck yeah.

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The Devil’s Threeway

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I was bored one night and took a cruise through Craigslist Casual Encounters MF4M (Male, Female looking for Male). I saw one post about taming an Asian cougar slut and IMMEDIATELY got my attention. Opened up the link and found a pretty decent picture of the woman, a little older than what I’m used to, but I’ll deal with it for a chance at fucking her. In the description the guy wanted to tag team her since it’s been her fantasy to have two guys at once. I decided to go for it 😉 But with all craigslist ads you respond to, there is a huge chance that they won’t respond. To my surprise, they did an hour later.

Hey! Love your pictures! Wanna chat today or tomorrow, we’re certainly interested.

                -Donatello

Holy shit.  Game on.

So I begin to text on Sunday to get the details with Don. He tells me that she’s his slave and recently out of a divorce, hence why she needs some taming. I will not lie, I was nervous as hell about this. I mean, I’ve done a MMF threesome before, but this time was going to be with a couple I didn’t know. (The other couple will be a story on a different day). He tells me that if she gets out of line, he’ll tie her up for me to fuck her.

Don: I’ve trained her in deep throating and anal.

Me: Seriously? How did you do that?

Don: She was inexperienced because of her marriage and wanted to be trained in how to do stuff. So I turned her into my little slut slave.

Me: I’m impressed, perhaps I’ll see this soon?

Don: How does Wednesday sound?

Me: Game on brother.

Wednesday. All day I’m thinking about if I should go or not. Their hotel is located an hour from where my work is so I’m apprehensive to go in case they bail. Really, I’m just being a bitch and thinking about everything. “What if they aren’t real and want to rob me?” “What if the dude is gay and wants to rape me????” Yeah, I was seriously thinking all of that.  He sends me a text later to confirm that I’m going, I say yes and decide to go for it. I remember reading Swingland by Daniel Stern and he mentioned how it’s very rude to bail on a couple that wants to play, especially if they aren’t a real couple since finding time is hard. While in the city, we agreed to meet for drinks at a Spanish bar, I text my two friends (guy and girl) who happen to be hanging out together for a pep talk. On my way to the bar…

I get in there and I find Suzie and Don sitting in the corner of the restaurant/bar. Suzie is wearing a bright red dress, red lipstick, and fishnet stockings. For a woman who looks in her late 40’s she’s quite the hottie. Don, as I found out, is from Madrid and is here working in the tech industry while Suzie is a well-known doctor. The conversation is about me and getting to know who I am, really it was more of a polite interrogation. The more Suzie drank, the more she became more direct and a little harsh with questions. Don keeps apologizing to me but I didn’t care, I knew what I was there for. Come to find out, Don is currently seeing someone, a very hot Korean girl, and we can’t use his place for our fun since his roommates will get suspicious. I won’t judge, people live how they want. Don suddenly gets up from the table and uses the restroom, leaving the sex craved cougar and her prey (me) alone. She looks at me:

Suzie: What do you want to do with me?

Me: (nervous but taking some courage) I want to take you back to your place and fuck you in ways you only dreamed of.

Suzie: You should get my number so we can play without Don sometime.

Whoa. I’m stealing the slave??

After an hour and a couple sangria’s later, Suzie says, “Ok boys, it’s time we go back to my place.”

While on the way back, Suzie is still interrogating me. With each question, she grabs my beard and pulls very hard demanding that I answer her. I have no problem with pain but Jesus Christ that hurt. Don keep apologizing but whatever, I’m about to get laid.

We get back to her hotel and inside the room I begin to pour champagne while Don puts on music. Armin Van Buuren. This guy knows some good music! And just like that, it begins…

He starts by kissing her and removing her dress. Under is no bra, garter belt, and stockings. Dear lord. He lays her on the bed and starts going down on her. I decide to take initiative, and I kneel next to her head and shove my cock in her mouth. She sucks really hard but I can deal with it. She doesn’t use her hands at all, just lips and mouth to give me a fun blowjob. I make it interesting by grabbing the back of her head and slowly thrust into her mouth. I’m face fucking her. Don, on the other hand is enjoying the sight of this!

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Don: Do you like his big cock in your mouth?!

Suzie: mmmhmmmm (my cock still in her mouth)

Not that it matters in a devils threeway, but I did happen to see his package (hard NOT to notice when she’s taking turns deep throating us). I’m easily bigger than him by an inch and a half or two inches. Once again, not that it matters, but it’s a nice ego boost when you’re the biggest package in the room.

Don, grabs Suzie by her ass and throws her around to be on her fours. Now I’m kneeling and leaning back against the headrest of the bed and Don is fucking her from behind as she is violently sucking on my cock. After about 15 minutes of this, my turn.

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This is where the story gets interesting. Suzie, in a drunken stupor, lays on her back and starts kicking me in the chest. I stand my ground and flex about every muscle in my body, but God damn, she has some power. Don holds her down and says that she’s fine. Obviously not. Now I’m left with if I should continue or leave since this woman is crazy. Don starts whispering into her ear and Suzie calms down then gets on all fours. I begin to fuck her while she starts blowing Don. After a few minutes of this, Don cums. Which thank God I wasn’t the first, I’m sure it would have been fine if roles were reversed but still, another big ego boost haha.

This is something that, may not seem like much, but I found funny enough to add. While I’m fucking Suzie from behind and she’s blowing Don, I happen to look up at Don. He’s looking at me with a smile. Not a creepy pedophile smile, but one of accomplishment. He holds out he fist to me, while Suzie, completely oblivious to this, keeps blowing him. I recognize the sign he’s giving me. Giggling to myself, I hold my fist up and connect. He laughs and says, “Brooooo.”

Seriously. What the fuck lol.

I last another 20 minutes and finish. After which, Don goes to take a shower.

Suzie: Let me get your number, you are a lot of fun.

Me: Oh really? You seemed like you were enjoying yourself.

Suzie: Yeah, but I’d like to fuck just you sometime.

Score.

After another 15 minutes of chit chat, I politely leave. My conversation with my two friends from earlier is nothing short of a school girl meeting her celebrity crush. Don texts me later with the picture of the girl he’s dating, she’s easily a 9, Korean, and wanting either another guy or a couple. I told him we could plan later. Walking to my car in the city all I could think was, I can’t believe I just did that.

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