This is a true story from a few years back regarding a particularly adventurous night I had with my girlfriend at the time, Alison. It’s without a doubt the kinkiest situation I’ve ever taken part in, and I thought it would be worth sharing here.
Whenever I go a few weeks without sex, and a few days without masturbating, it can lead my brain to end up in a very horny and perverted state. This night in question ended up being a result from one of those such instances. As best as I can remember, it all started while I was at work, but with me hopelessly lost in the various sexual fantasies running through my head. I was sitting at my desk, staring blankly ahead at my computer, but I couldn’t stop thinking about Alison. In situations like this, I would start daydreaming about all sorts of ridiculous sexual scenarios involving Alison and me, but my horny brain would try to justify them as somehow plausible. In this instance, I was focused on something specific Alison had mentioned to me a few months prior, that until then I hadn’t given the attention it rightfully deserved.
Alison and I had been dating for roughly a year and a half at this point. I was a pretty typical 26 year old guy, while she was 25 and awesome. Describing her in one word was easy, she was the definition of cute. She was on the smaller side, but not ridiculously petite. She was probably 5’3″ and 120 lbs. She had shortish natural blonde hair that came down to just above her shoulders, and an extremely cute face. She wasn’t very curvy, as her boobs were just B cups, but she did keep herself in decent shape. She did have a little bit of pudge, but I felt that only enhanced her cuteness. She also had the sweetest personality and was just an extremely nice person. You add it all up and she was the perfect girl-next-door type that I had always found extremely sexy.
Alison was also a lot of fun when it came to sex. I didn’t think of her at the time as super kinky, but she did have a little naughty streak. Sometimes for no reason, she would flash me when we were out in public. It would only ever be for my eyes, but she might pull down her dress quickly to reveal a nipple before immediately covering back up. In terms of sex, she was usually willing to give most things a try. We had even had anal sex a couple of times, and while I got the sense it wasn’t her favorite, she still suggested it as something adventurous for us to try.
One thing she wasn’t a fan of though was getting her ass licked, which was too bad because I found it so appealing. Sometimes she would be on all fours and I would have a chance to admire her ass crack, and it was gorgeous. She would have a few scattered blonde hairs around her asshole that would feel so good touching my nose as I hovered my face in there. She was convinced though that licking an asshole was just too inherently gross that no one should ever subject themselves to that. And it didn’t matter how many times I tried to tell her that I was willing to do it so badly, she never could get past her own grossness factor. Normally, if a girl told me she wasn’t into some aspect of sex, I’d have no problem completely respecting that, but I definitely struggled with this. It was probably because her reasoning seemed like she was trying to needlessly protect me, but either way, I definitely asked her way too many times, but every time I would get denied.
Anyway, back to my sexual daydreaming at work… A few months prior, Alison and I had been discussing some of our own sexual fantasies. During this talk, she had mentioned that she had always had what she referred to as an “intruder fantasy”. Obviously, when I heard this, I had to ask for more details.
She went on to explain that as crazy as it sounds, she found the idea of a guy breaking into her bedroom and “having his way with her” (her exact words) to be a huge turn on. She clarified that she didn’t want to actually get raped for real, but that it was simply the make-believe fantasy that she found appealing. Alison then added that in her fantasy, the guy breaking in would have to be really good looking. She loved the idea that it would be a guy who was very capable of finding other girls who would willingly have sex with him, but that he was so unsatisfied, that he would be willing to go so far as to commit a crime to have sex with her instead.
At the time, I definitely remember thinking it was unbelievably hot that Alison had such a kinky fantasy. Now normally, if a girl I was dating described a fantasy of hers to me, my first instinct would’ve been to make it happen, no matter what it was. The sooner the better too! But in this case, for whatever reason, I didn’t even consider this was something we could actually attempt. There was no doubt I was hugely turned on by her fantasy, but I must’ve just thought it was such an unrealistic and unobtainable scenario, that I didn’t even consider it in that way.
Fast forward to my day of extreme horniness while at work. Not only did the thought of Alison’s fantasy cross my mind, but it was literally all I could think about. It was basically a perverted epiphany. I’m thinking to myself, “Holy shit, Alison has a fantasy about getting pretend-raped, and I NEED to make this happen. How do I make this happen?”
In about an hour, I went from never having considered this fantasy in real life, to being completely obsessed with pulling it off. I quickly realized that if we’re ever going to do this fantasy justice, it pretty much has to involve another guy. I’ve never been much of an actor, so trying to pull off some purely role play scenario involving just the two of us almost certainly would’ve been a huge letdown. It might’ve been high in comedic value, but it would’ve been very low on the sexiness scale. So in order to make this work, I was forced to ask myself one key question: Could I really handle seeing Alison with another guy?
Again, it doesn’t seem to matter what the scenario is, it won’t be any match for my horny state of mind. I find myself thinking, not only could I handle watching Alison fuck some other guy, but it sounds downright amazing. Part of the appeal is in the idea that the two of us, mystery guy and me, would be acting as a team working together to enjoy Alison as much as possible. Supposedly it would be her fantasy, but how could it not be ours as well? I start to just love this idea. There are still so many potential details to work out, but I decide right then and there in my office that I need to at least bring this scenario up with Alison and see what she thinks.
I got home that evening before Alison, and normally if I was this horny, I wouldn’t think twice about jerking off to relieve the build-up. In this case though, I was worried that if I came and cleared my head, I’d immediately lose interest and no longer have this urgent need to talk to her about the fantasy. I’d probably end up convincing myself that it could wait, and who knows, later on I might just chicken out completely. I didn’t want that to happen, so I couldn’t possibly let myself cum until after I had gotten the courage up to tell her.
By the time Alison got home, I had dinner for the two of us ready so we immediately sat down to eat in front of the tv, like we normally would. A few minutes in and I start the conversation with, “So I’ve been unbelievably horny today.”
Alison quickly responds apologetically, “I know we’re overdue for sex. I’m sorry, I’ve just been so swamped lately.”
“No, no, I’m not complaining about that at all.”, I try to assure her. “I know you’ve had to work way later than you normally do these last few weeks. It’s totally fine.”
I decide to just jump right in. “Listen, I know this is so random, but I was thinking a ton about the intruder fantasy you had mentioned awhile back.”
With this, Alison just kind of laughs and goes, “Oh really? What brought that up?”
I tell her I don’t know what initially made me think of it, but that once I did, I starting obsessing over the idea that we should try and make it happen.
Alison interjects, “You know I said it wasn’t a real fantasy, I just like the idea of it, so it’s not something I would even want to happen.”
“I know, I know.” I respond. “But what if we could do something that seemed real, but was totally safe?”
“You’re gonna put on a ski mask and climb through our window?”
I respond, “Ha. I thought about that, but I decided that would just be kind of lame. I was trying to think of a scenario that would be totally safe, but also really fucking intense. And so now I have this idea, and it just turns me on beyond belief just thinking about it.”
Alison is obviously quite curious now and says, “Ok, go on…”
“So picture this… you’re asleep in bed. Meanwhile, another guy and I both sneak into the bedroom, wake you up, and force you to have sex with us. Both of us.” Before waiting to even see her reaction, I try to explain it a bit more, “We would have a safe word so you could end it at any point, no questions asked. But there would be no need for pretending or acting, it would actually be me and this other guy just doing whatever we wanted to you, and you could react however you wanted. The whole key is involving this other guy, though. If it’s just me, then it’s obviously going to feel consensual because we’ve had sex a hundred times before. But if there’s a stranger there, then fuck it’s going to be intense. And I would make sure the whole time that we weren’t being too rough, so it never became painful or anything, and like I said if it ever started to be too much or too uncomfortable, you could always stop the whole thing at any point.”
I finished my speech and waited for a response. Meanwhile, Alison just looked at me with a totally blank expression. I break the silence with, “I assume you’re not onboard?”
Another few seconds pass and Alison says, “Yeah, I don’t know about this. First off, the huge question you didn’t even address… Who’s this other guy?”
“Ha. Excellent question.” I answer. “Short answer? Anyone you want. I mean either it’s a friend of ours or a stranger? My vote would be a stranger, but then there’s the question of how do we find this stranger? I know this whole scenario is ridiculous, but god my heart is pounding here just discussing it with you. Doing something like this would be the ultimate adrenaline rush, I can’t even imagine.”
“Wow, I don’t think I’ve ever seen you this worked up before.” Alison points out. “You seem really nervous right now too.”
“Yeah I’m definitely nervous.”
“Ok, well there’s no need to be nervous just talking to me about this. I’ll tell you right now, it’s not a hard no. But, would you really be ok watching another guy fuck me?”
“If we’re both fucking you, then definitely. One thousand percent. And if you add in the forced aspect, then holy fuck yes.”
Alison pauses to contemplate what to say next, and then goes, “I’ll tell you what. Let me think about it some. And while I’m doing that, why don’t you come up with a hypothetical plan with how you’d find this stranger. I agree there’s no way we could involve one of our friends in this so it has to be a rando.”
Hearing this is way more than I was expecting so I’m pretty psyched. And then Alison adds, “And remember, this new friend of yours who is going to rape me has to be hot. Really hot.”
I purposely had not used the R-word the entire time discussing this with Alison, and I’m pretty sure she hadn’t either. I avoided it mainly because I was worried it would make the whole idea sound too extreme. So when I heard her use the phrase, “rape me” my heart just about skipped a beat.
I was so overwhelmed and turned on by the possibility in front of us that after we finished dinner, I acted like I had to go take a shit, but instead went into the bathroom to finally cum. I was so paranoid about leaving the state of things exactly where they were, that I didn’t even want to chance things by asking Alison for sex after our conversation. Instead, when I got into the bathroom, I promptly took a seat on the toilet and replayed Alison’s words “this new friend of yours who is going to rape me has to be hot.” in my head. The sound of her voice saying those words was just unbelievably exciting. I immediately started pumping my cock, pointed it straight down, and then started cumming into the water below. I held it there until my squirts were all done, and then I cleaned up the tip with a single piece of toilet paper. I felt so much better. I went back out and could finally relax after that huge buildup and release. Going to bed that night, I felt so content that the conversation with Alison had gone well, but I still had plenty of nerves and excitement about what was to come next.
That next day, I started coming up with our plan to recruit this mysterious stranger. This was quite a number of years ago, so there was only one obvious place to start the search for this guy, and that was Craigslist. I ran the idea of posting a feeler ad online with Alison, and she gave me the go ahead. I told her I was going to keep it completely anonymous and just mention the bare minimum of what we were looking for. It basically said we were a couple looking for an intelligent and attractive straight man to take part in a consensual non-consensual scenario. I didn’t post any pics of us, and I even asked for them not to send pics until we had chatted a little. I finalized the post, submitted it, and then waited.
Over the next day or two, plenty of responses came in before it started to dry up. The problem was that quality responses were few and far between. I only had two simple criteria a response had to have to be considered. First, it had to include at least a couple of complete sentences, and secondly, it had to not have a pic attached to it. I mean, that was explicitly in the instructions. For such basic requirements, it was pretty disappointing to only have like two responses pass this test. I followed up with both, and after a couple messages with one of them, I asked the guy to send a picture.
I won’t go into a detailed description of the guy, but upon seeing his pic I was pretty confident it’d be a no-go with Alison. And sure enough, when I showed her contestant #1, she looked at him for half a second and said simply, “Nope.”
I was a little disappointed at our initial attempt on Craigslist, but I wasn’t about to give up. I waited a week and then reposted our request again. For whatever reason, this time was a lot more promising. I probably got 4-5 leads where it was worth having them send a picture. I definitely had a favorite among them from our brief conversations, as there was a guy named Jason that seemed both comfortable with the scenario and was also able to crack a few jokes that showed he had some personality. I waited until I had pictures from all the guys in this round and I showed them each to Alison. I probably would’ve ranked this Jason dude as second best by appearance, but what do I know? As luck would have it, Alison went through them one by one, and gave them all no’s except for a single yes, this Jason guy.
“Oh really?” I said. “I actually like this guy the best based on his messages too, so maybe we’re onto something here.”
“Yeah he’s cute. He looks like an assertive guy too.” Alison added, whatever that means.
“Should I send him a pic of us?” I asked, thinking that was the step where all of this would become pretty fucking real.
“Go for it.” Alison said, with a look as if she was calling my bluff on this whole adventure.
And that was that. We were about to take the next big step forward and blow our anonymity. I found a pretty benign picture of the two of us where we were dressed nicely, but nothing that was too revealing of Alison. It did have a clear shot of both of our faces though, so there was no hiding who we were. I replied to Jason and mentioned that Alison loved his pic, and included the picture of us as well. Only a few minutes had passed before we got a reply that simply said, “You guys look great!”
I was in the process of replying back to start going over our proposed scenario when a follow up email came. In it, Jason asked if the three of us could chat briefly on the phone. I checked with Alison and she was fine with that, so I abandoned the email I was working on and instead sent our cell number back.
A minute later we got a call and it was Jason. We put him on speaker and Alison and I just kind of looked at each other like, what are we doing?
Jason was perfectly nice on the phone. He started off by saying, “Hey, thanks for taking my call. I know I’m paranoid but I figured before we go any further on this we should probably just chat to confirm we’re all actually real people.” And then he laughed.
In hindsight, it made sense that he wanted to talk to us as he had only been chatting over email with me to that point. Not only did he need to make sure that Alison was a real person, but he probably was most worried about confirming she was fully aware of this whole scenario and it wasn’t some sick stunt I was pulling without her knowledge.
So with the three of us all on the call, we were able to assure everything was above board. Jason was easy to talk to and he and Alison actually had a number of back and forth exchanges that seems to go well. Since we were already chatting, I figured I would go into some details about how I envisioned the night going.
I proposed that he and I would meet later in the evening at a bar a few blocks from our place. At this point, Alison would head to bed like she normally does. While she was falling asleep, Jason and I would get to know each other, have a few drinks, and plan out how we think the scenario should go. I warned him there was a very real possibility that while I was at the bar, I could get cold feet and decide to call the whole thing off. He was very understanding and even mentioned that I should be prepared for him to back out just as well. For whatever reason, him saying that put me at ease even more. I then explained that after discussing everything we needed to, if we were both on board, we would head back to our place together and begin the fantasy.
We all agreed on the plan, and we decided to do it this upcoming Saturday night as that worked for all of us. We ended the call and Alison looked at me and said with a kidding / not kidding demeanor, “I don’t know about you, but I’m kind of excited!”
I responded nervously and honestly, “ha ha ha, I’m also excited, but mostly terrified.” And then I took Alison’s hand and put it on my chest so she could feel my heart racing.
“That’s just from talking to this guy on the phone? Holy shit, are you going to be able to handle this?”
I told her I had no idea, and boy was that the truth.
Fast forward a few days and Saturday evening had arrived. It was a little before 8pm and the plan was for me to meet Jason at the bar around 10. Alison and I were having some last minute discussions, when I noticed I got a text from Jason that said, “can I give you quick call?” So I dialed him up.
Jason answered and apologized because he had a last minute request. He asked me if I could have Alison call his cell and leave a voicemail, just so he could “cover his bases” as he put it. In this voicemail, he asked that Alison state the current time and date, and then give her name, my name, and Jason’s name and mention that we all were going to partake in a consensual non-consensual sexual role play fantasy this evening. And then finally, he wanted her to state that Jason had her full consent to have sex with her, but that the consent could be withdrawn if a particular safe word was mentioned. And then he asked that Alison state her safe word in the recording.
Again, this whole scenario was totally new to Alison and me, so I had never thought about how things could go wrong for someone in Jason’s position. I totally understood where he was coming from, but more importantly it made me realize that Alison and I hadn’t even agreed on a safe word yet!
I told Jason it was no problem and then relayed what he had asked of Alison to her. She was totally fine leaving the message like he wanted, but first we had to settle on what our safe word would be. After talking it through, we actually decided on having two easy to remember safe words, “yellow” and “red”. If Alison said the word “yellow” that would mean there was no need to break character and shut everything down, but just that whatever we were doing, or about to do, we shouldn’t. But if Alison ever said the word “red”, then it was time to halt everything immediately.
I then asked her to clarify what sorts of things she wanted the two of us to do to her, and what sorts of things she didn’t want, just so I would have a better idea going in.
Alison kind of took issue with the question and said, “It’s not supposed to be my choice, right? We have our safe words now so I can use them if I need to, but otherwise you guys can feel free to try to do anything you want.”
At that point a rush surged through my body as I started to realize what might lay ahead this night. When she mentioned that we could try anything we wanted, there was only one thing that immediately popped into my head, licking Alison’s asshole. I had craved that for so long, and I thought maybe tonight would be my chance. Even if she calls “yellow” on it and shuts me down, it still would’ve been worth the shot. But I figured if there was ever a situation where she’d be ok with it, this was probably it.
We finish going over the last few details and Alison calls Jason’s phone and leaves the detailed message like he wanted. Afterwards, we get a text that says, “perfect. Thanks!”
Alison then mentioned that she was going to go shower and shave before bed, which is something she never normally would do at night before going to sleep. So that was hot just thinking she was prepping herself for us. By the time she was done, it was almost time to meet Jason at the bar so I gave Alison a kiss and joked, “Don’t wait up!”
I head out to walk to the bar and I’m pretty fucking nervous. To this point, both Jason and Alison have seemed so nonchalant about this whole affair, while I’m scared shitless. And it was basically all my idea! I get to the bar a few minutes before 10, and I text Jason that I’m there.
He must’ve gotten the text and seen me standing at the doorway because he gives me a small wave from the table where he’s sitting. I walk over and he stands up to shakes my hand. How very professional of him, right? I’m immediately struck by the size of his hands, as they seem abnormally large. He wasn’t extremely tall, but he was probably 6 feet, which was certainly taller than my 5’8″. He had short dark brown hair, and looked to be in very good shape. He was well dressed and well groomed and overall just very similar to the picture he had sent, so all good and no surprises there.
He offers me the other seat at his hightop table, and I sit down. He’s already got a pitcher of beer and two glasses so I help myself and pour a glass. I thank him for the beer and we start with a little small talk. Thankfully, he’s just a nice and genuinely easy to talk to guy, because otherwise I don’t know how I would’ve survived the situation.
Eventually he concludes the get-to-know-you conversation and breaks the ice with, “So Alison’s in bed?”
I respond that if not yet, she should be getting into bed any minute now and mentioned she was just showering and getting ready. Jason then asks what she usually wears to bed, and I tell him that normally it’s just a t-shirt and shorts but I wasn’t sure if she’d wear something different tonight or not.
“Good, I like the surprise of not knowing.” He said with a smile. He then followed up, “I have to say, Alison looked adorable in that picture you sent. And on the phone she sounded like a really nice girl!”
“Yeah, she’s awesome. I still can’t believe she’s up for doing something like this.” I responded.
“You hit the jackpot there.” Jason boated. “There is simply no better combination than a sweet AND kinky girl. Fuck, man. And then you add the fact that she’s a blonde too! I love blondes.”
Something about hearing Jason go on and on about how lucky I was certainly was a nice ego boost. Who doesn’t like hearing that? And then thinking of Alison back in bed while the two of us were talking about her started to get me quite hard. I could feel my cock growing in my pants and almost reaching full boner.
Next, we start discussing what we’ll first do when we get back to the apartment. We decide that we want to be as quiet as possible so hopefully we can get all the way into the bedroom without waking her up. I mention that I would also like to blindfold her right at the start, and I suggest we use a long sleeve t-shirt that I purposefully left out to tie over her eyes.
Jason agrees and then asks something I definitely hadn’t thought about, “Should you and I get naked before we wake Alison so we’re ready to go immediately?”
I never played organized sports in high school or as an adult, so despite being a grown man, I’ve hardly ever been around other naked men in any scenario. I figure if we’re eventually going to be having sex with Alison in front of each other, there’s going to be nothing to hide, but even the thought of standing naked next to this stranger has me nervous. But at this point I just don’t want to rock the boat so I’m willing to go along with anything, and I respond, “If you want to, sure?”
Jason laughs and says, “We can play that one by ear.” He then follows up with another question, “So is your girlfriend going to be acting like this is an actual rape, like is she going to be saying ‘No, No, Stop’ and everything like that?”
I honestly don’t know how Alison is going to respond, so I tell him I have no idea. I mention that we’ve never done any sort of role play before and Alison isn’t a big dirty talker either, so I’m guessing she might be pretty quiet? I then reiterate that this is all totally foreign to us and I have no idea if we will even last five minutes before calling the whole thing off.
Jason stresses that that’s totally fine and he has no problem abruptly halting as soon as anyone mentions the safe word. After clarifying that, Jason then points to the empty pitcher and asks if we should get another?
I think two pitchers between the two of us seems like the perfect level of inebriation, so I say, “Sure, one more and then maybe head out after that?”
“Sounds fucking great.” Jason replies.
I get the second pitcher from the bar, and when I get back Jason continues on with the questions. “So what does Alison like? What does she not like?” And then adds, “Basically, what are the limits here?”
“Ha. Yeah that’s an important question.” Then I go into some more detail. “She’s fine with all the normal stuff, like blowjobs and everything. We also discussed and since she’s on the pill, we’re ok if you wanted to go condom or no condom, either is cool with us. She and I have had anal sex a couple times, so I think that’s in play too?”
“Oh wow, nice!” As that clearly excites Jason. “I’ve never really had anal sex so I may have to take you up on that.” I didn’t know exactly what he meant by “never really” as I thought that was a weird way to phrase it, but I didn’t bothering asking him about that.
“Yeah, if you want to have anal sex with her, go for it. Just be listening for a ‘yellow’ or ‘red'” I stress. And then I figure I would bring up the part I was most excited about. “Is there any chance you’d be up for licking her asshole before you fuck it?”
“Yeah, definitely!” Jason answers and I immediately feel his response in my cock. I know some guys find ass licking inherently gross and have zero interest, but then others like me find it so damn appealing and sexy. I’m psyched that Jason is like me in this regard. I had strategically thought that Alison would be more likely to be ok with him doing it than me, so if he can go first and get her comfortable with it then there’s probably less of a chance she’ll stop me if I try.
The second pitcher winds down and both my excitement and nervousness begin to build. It’s roughly 11:30 so I’m pretty confident that if Alison was going to fall asleep, she would have by now. I decide that everything with Jason and this meeting has gone as well as I ever could’ve hoped, so it has to be a go.
“What do you think, should we head back to my place?” I ask and I swear my voices cracked just a little bit making me sound like such a tool.
“Let’s do it.” Jason says as he immediately gets out of his chair showing he can’t wait.
“Alright.” I say and we start walking out. It’s a little chillier than usual outside and I’m so nervous walking out that I actually start to shiver a little. I casually mention that it’s a little cold and hope that Jason just ignores my shaking. As we start walking the couple of blocks, I do start to calm down a little, and by the time we get to our apartment I’m ready to head up.
“Ok, so once we get inside, no talking until it begins?”
“Yep.” Jason confirms. “And you’ll make the first move?”
“Yep.” I respond. And with that I open the front door as quietly as possible and we silently head back towards our bedroom. The apartment is all dark, but there’s a fair amount of ambient light so we can still see reasonably well. As I lead us to the bedroom, I motion for Jason to stop right outside of it. The door is 90% shut and so I quietly open it up a little more and listen. I can clearly hear Alison’s rhythmic breathing, so it’s safe to say she’s actually asleep. I’m simply amazed that she was able to know what was coming tonight and not have it affect her falling asleep. How awesome is that, I think.
I poke my head out the door and mouth the words to Jason, “She’s asleep.” I think about how I really don’t want to wake her up before we’re ready, so I motion to my belt and start to unbuckle it, signaling to Jason that we should get undressed out here.
Jason seems totally fine with that and we both start undressing as silently as possible. I put all of my clothes into a small pile outside our bedroom door and once I get down to just my boxers I look over at Jason. He’s apparently a faster undresser than I am because he’s standing there completely naked and ready to go. I obviously can’t help myself and immediately look right at his penis.
Penis size was one thing that didn’t come up in our conversations beforehand, but based on the size of his hands during our handshake, I though there was a decent chance he’d be big. At this point though, the jury was still out. His cock looked to be an average size, but it also clearly wasn’t hard so I had no idea if it was close to its full size or not. I figured I’d know soon enough though once things got started.
With Jason naked, I had no choice but to join him, so I dropped my boxers and kicked them atop the small pile of my clothes. My cock was no longer semi-hard, as instead I was rocking a full-on-sticking-straight-out boner. And all 5 and 3/4 of an inch of it were embarrassingly pointing at this random dude standing next to me. But there was no need to dwell on that embarrassment as it was time for the two of us to go on in and get this party started. I led the way, quietly pushing the door open and we entered into the room. I picked up the t-shirt I had left out in my closet and then we both moved to opposite sides of the bed. We stood there for a second, just two buck naked dudes in my bedroom, as Alison slept peacefully on her back on our king sized bed. I grabbed ahold of the shirt’s two sleeves ready to use them as a tie and then I gave Jason a small nod to let him know I was about to begin.
In one motion I got up on the bed and placed the body of the t-shirt over Alison’s sleeping face. She woke up with a jerk and seemed legitimately confused.
“What are you doing?” were the first words out of her mouth. As she said that she also struggled to sit up, but I kind of forced her back down to the bed on her side. With the t-shirt still covering her face, this gave me a chance to tie the sleeves in a knot behind her head and secure the blindfold pretty well. I then reached up and grabbed her two hands and held them together.
“Jason, come get her shirt.” I instructed to my partner in crime as he came over and started lifting up the shirt she was sleeping in.
“What the fuck? Who the fuck is Jason?” Alison then said.
At this point, it became clear Alison was going to try her hand at role playing, as she was certainly awake and aware by now but acting like she didn’t know what was going on. In her first initial comments, she sounded fairly convincing but wasn’t quite authentic in her fear. But honestly, that was probably a good thing because if she was actually flawless in her rape victim role playing, I probably would’ve started to doubt whether we were still role playing!
Jason and I get Alison to be sitting up on the bed enough that while I’m holding her hands he’s able to slide her shirt up and off. After that, we set her back down on the bed and I ask Jason to hold her hands.
As Jason holds her two hands above her head, I get off the bed and head over to the doorway. I realized there was no need to be doing all of this in the dark so I flipped on both sets of lights in the room, and it’s now completely lit up. As I come back, I see Jason is holding both of Alison’s hands together with only his left hand while he’s using his right hand to grope her tits. His giant hands make her boobies look tiny and it’s such a sexy sight to see him manhandling her. He’s not being extremely rough, but he’s not being that gentle either. He’s cupping her tits and pinching her nipples as if he’s doing it solely for his own enjoyment. Alison’s face is completely covered so I have no idea what kind of expression she has, but she is moving her hips and legs around in a sort of struggling motion. I don’t know if she could’ve gotten out of Jason’s grip if she wanted, but it looked like he had total control over her.
“Jason, let me hold her arms.” I suggest. We transition our positions so I now take control of both of her arms and Jason moves towards the foot of the bed.
I lift up the t-shirt covering her face and adjust it so it’s now only over her eyes and we can see her mouth and nose. After taking care of that, I lean in and quietly start speaking into her ear. I say it loud enough though that Jason can hear too.
“Babe… So this guy in our bedroom is my friend Jason. I happened to meet him at the bar tonight and he was going on and on about how lame the girls he’s been fucking are. He just wouldn’t shut up about it. So I started talking about you and I even showed him a few pictures of you and he said that you were exactly the type of girl he’s been dying to fuck and just how jealous he was of me.”
I’m doing my best to role play around what I thought Alison’s fantasy was all about, and it seems to be working as she’s not saying anything but her breathing starts to pick up in intensity.
“I really wanted to help this poor guy out so I told him that he could come back with me and fuck you as much as he wanted. And when he asked what would happen if you didn’t want that, I told him we weren’t going to give you a chance to say no.”
“But I don’t want to fuck some stranger.” Alison adds meekly with her best attempt to play along.
“Well you clearly don’t have a choice now, do you, so it doesn’t really matter.” I say as I make eye contact with Jason, who has a pretty relaxed and amused face on. I then give him a sheepish I-don’t-know-what-the-fuck-I’m-doing look before finishing with, “Jason, I think you should take her shorts off.”
“With pleasure!” He responds.
Jason takes his fingers and slides them inside the waistband of Alison’s shorts. When he does this, Alison takes an intense deep breath in, so much so that I can see her rib cage for a brief moment. As Jason begins to move his hands down, it’s clear he has the waistbands of both her shorts and her panties underneath, so when he starts sliding them down off her ass, Alison’s naked pussy is exposed. He then lifts her legs up in the air and slides the shorts and underwear up her thighs and off her already bare feet.
He tosses the clothes aside and now all three of us are completely naked. Jason wastes no time and uses his hands on her thighs to spread eagle Alison, and which point he goes “Fuck, yeah.”
He immediately goes in and gives her pussy a big wide lick. With this, Alison lets out the first small sign of pleasure I’ve heard from her with a quiet but noticeable exhale. With the lights on, both Jason and I have a full view of Alison’s vagina now. After the lick, her inner lips are nicely parted and her vaginal canal is easily visible. There’s also a noticeable shine all over her inner and outer lips that couldn’t have just been from Jason’s mouth, so she’s clearly quite aroused.
“Nice job shaving, Alison.” Jason says as he moves his head closer to her crotch to inspect everything down there. Alison usually keeps her pussy bare and today is no exception as she’s completely bald above her pussy. Jason then pushes her legs back towards her face which tilts her ass up. Meanwhile, I’m up near her head still holding her arms pinned to the bed watching intently on everything Jason is doing.
After giving Alison’s pussy a couple more licks, Jason stands up and switches to holding her legs pinned back over her head with just one hand. His other hand is now free to roam her pussy and ass. After running it along her lips and then ass crack, he comments, “It looks like you missed a few hairs here.” And while he says that he’s running his finger gently across some of Alison’s very fine hairs close to her asshole. He then leans down and says, “I don’t think I’ve ever seen such blonde pubes, or in this case, ass hairs, before. I love it.”
At this point Alison is pretty silent and not responding to Jason’s commentary, or at least verbally she isn’t. I’m right next to her face, so I think I have a decent sense of her mindset even though her eyes are covered. She seems genuinely turned on and into it, but slightly on edge too. Jason then continues on with his finger running it up and down her ass and pussy until totally out of the blue he plunges his index finger all the way into her asshole. I had no idea he was going to do this and I’m sure Alison didn’t either.
Alison instantly reacts with a strong grunting “uuuuggh” signaling some serious discomfort with Jason’s finger all the way in her butt. Again I’m totally caught off guard, so my immediate thought is it’s game over, and the only question is whether Alison says “red” or “yellow”. But shockingly, she says neither. Instead she catches her breath and says, “Not my ass! Fucking take it out!”
Here I’m genuinely torn as I think there’s a chance in the heat of the moment that Alison wants him to stop but forgot the safe words. I can’t decide whether I should break character and either tell Jason to take his finger out or maybe just ask Alison if she remembers she can use the safe word. But at the same time, I’m terrified of being the lame one of the three. So far, Jason has been rougher and more aggressive that I was expecting him to be, but Alison surely must remember those easy safe words, so is it possible they both just know exactly what they’re doing and I don’t? I can’t make up my mind so I take the easy way out and do nothing.
Jason ignores Alison’s plea to remove his finger, and instead I can see his third knuckle moving slightly as if he’s circling his finger around inside of her rectum.
Alison continues to look really uncomfortable and begs, “Jason, please take it out. I hate that feeling.”
Jason actually complies and says, “Ok, Alison.” as he removes his index finger from her ass. He then immediately sticks the same finger right into her pussy, and I can clearly see he’s moving it all around inside. I can tell he’s again being kind of rough as I can see Alison wince. He doesn’t keep that finger in long though, as soon enough Jason extracts his finger and proceeds to bring it up to his nose and takes a big sniff.
“Mmmmmmm. I love the smell of pussy and ass all mixed together.” He says.
I certainly can’t argue with him there as I know exactly what he’s talking about. And I also understand when next he takes that same finger and sucks the flavor off of it into his mouth. He then pops his finger out and simply says, “So good.”
Jason now lets Alison’s legs come down a bit and they kind of rest on the bed with her knees up. He walks around to the foot of the bed and grabs her hips and pulls her whole body down towards the end. And for the first time, I get a good look at Jason’s erect penis as he stands at the end of the bed and rests his cock on top of Alison’s pussy mound. There’s no longer any doubt, it’s definitely bigger than mine.
It’s clearly thicker than mine has ever been, and it’s at least a full inch longer, if not more. Alison of course is still blindfolded and has no idea what’s to come. I can see Jason is getting ready to fuck her and Alison probably starts getting that idea too as he presses up against her and lays his cock across her pubic mound and towards her belly button.
I instinctively abandon my position holding Alison’s arms down so I can get a better look. At this point, she’s kind of stopped with the fake struggling anyway so there’s no real need to keep pinning her down. As I stand up, I can see how far Jason’s cock extends over her belly and it gives me butterflies just thinking about that thing stretching her pussy that far.
With Alison just laying still on the bed, Jason slowly lifts her legs up slightly and places the tip of his cock at her opening. As he does this, it becomes clear that he’s perfectly willing to take us up on our offer of not using a condom. He starts to guide it in, and as he does I can see Alison notice it’s larger than what she’s used to.
“What the fuck is this?” She asks.
Neither Jason nor I say a word as he continues to push it in further. He slowly and methodically slides the whole thing in until his pelvis is completely pressing against her. Alison’s only defense is using her hand to hold his abdomen back, but it’s useless to stop him from completing his first full thrust. After a slight delay, Jason begins his second thrust, and then a third.
I’m pretty overwhelmed by seeing Alison actually getting fucked, so I distract myself by leaning down right next to her face and whispering, “His penis is a lot bigger than mine.”
“No. shit.” Alison responds in a weak and breathy tone with a pause between the two words.
At this point Jason starts actively fucking her by bringing his cock all the way out before sliding it all the way in, over and over. He’s doing this at a somewhat slow pace, but each thrust is met with Alison making a grunting noise at the moment he hits the back of her vagina.
I’m watching this still a few inches from Alison’s face and I continue on to her, “Jason was complaining that a lot of girls don’t let him push his entire cock in, but I promised him you could take it.” This off course is total bullshit as Jason and I never discussed anything about his penis over email or at the bar.
But Jason seems willing to play along as after hearing this he starts fucking her even harder and says, “Ahhhh, it feels so good to finally be able to do this. Thanks, dude.” Alison continues to struggle to take each thrust, but Jason seems in no hurry to either stop or to cum. In fact, he then offers up a suggestion.
“Why don’t you have Alison suck your dick while I’m fucking her?”
I’ve barely done anything so far in this supposed double team, so I’m certainly not going to say no to that. I climb up on the bed and Alison obediently turns her head towards my cock and I place it into her mouth. It’s not a great angle though, so between that and the fact that she was distracted by the largest penis she’s ever had inside her, she wasn’t able to do much with my cock. But soon enough she started to get a rhythm going and was actually sucking me off.
It doesn’t take much of that though until I start worrying I’m about to cum, so I casually pull myself out of her mouth and suggest to Jason that we switch places. My thinking was if I’m fucking her, I’ll have a lot more control over whether I cum or not so I should be able to delay that process. I’m deathly afraid of cumming too soon in this whole adventure. Jason agrees and extracts his cock from her pussy and trades places with me.
As soon as he climbs up to put his penis into Alison’s mouth, something else pops into my head. Alison has NEVER been a fan of her own taste. So much so that not only would she never suck me off after I’ve been inside her, but she wouldn’t even kiss me or let me near her face if I’ve been licking her. So I realize that she’s probably not going to be a fan of Jason’s cock that is noticeably glistening from her pussy juice.
But in what starts seeming like a pattern, Alison’s reservations that I thought I knew, are nowhere to be found as she eagerly uses her hands to feed Jason’s cock into her mouth. In fact, in doing so she even turns her body making it hard for me to have an angle to fuck her. She definitely can’t get his whole penis in her mouth, but she’s improvising by licking the sides and even rubbing it all over her face. All of this is brand new to me as I’ve never seen her give a blowjob like this before.
I almost forget that I’m supposed to fuck her and find myself just watching the show in front of me. But eventually, I’m able to adjust her lower body and reposition her pussy towards me so I can slide my cock inside her. Normally, our process of starting to fuck would take a minute or two of gentle adjusting to let her get lubricated enough for me to slide in easily. This time was nothing like that though. Not only was she ridiculously wet, but her canal was wide fucking open from the brief but intense pounding she just took, so I slid in so easily.
Jason sees me inside and gives me a little encouragement, “Nice work… keep fuckin her, man.” This fucking and sucking goes on for another couple of minutes until Jason decides to pull out of her mouth. Again, Alison is still blindfolded but has turned into a pretty willing participant at this point. There’s definitely no need to hold her down anymore. But I guess Jason wanted to put that to the ultimate test, because the next thing I know he’s climbing across Alison and starts pinning her arms down with his legs. But as he does this, he’s facing me and basically straddling her blindfolded head while on his knees.
He then says, “I have a new idea.” and as he says that he begins slowly spreading his own legs wider and wider which lowers his body closer and closer to Alison’s face. It’s at this point, I first realize what he’s doing. He’s going to sit on her face and try to have her eat his ass.
Up until this point, Jason had certainly pushed a number of boundaries, and every time I was surprised to see Alison go along with it. But this time, I knew there was no way she would be ok with what he was trying to do. This was the girl who found it too disgusting to let someone ELSE lick her ass, so there’s no way she going to be up for licking some guy’s asshole. The only question now is whether it led to her calling “yellow” or straight to a “red”.
Jason got his hips lower and lower until he was inches away from Alison’s face. After that he took a look at the positioning of her head and moved himself up a few inches, until he seemed to be satisfied with the alignment. And then finally, he uses his two hands to spread his ass cheeks totally apart, and he finishes by sitting down right on Alison’s nose and mouth.
Alison hadn’t said a word while Jason got himself positioned for this supposed ass licking. I’m pretty sure since she was blindfolded, she had no idea what was coming. She also was pretty immobile having her arms pinned down by his legs, so there wasn’t much she could do to stop it anyway. But the moment he sat his ass on her face, she immediately started struggling to break out of the position. Her legs starting kicking around, so much so that I had to take a full step back to avoid getting hit. I could also hear some muffled noises coming from her mouth, but since she was smothered by Jason’s ass, it was impossible to hear what she was saying. I couldn’t tell if she was trying to say yellow or red but I’m sure it was one of them.
At this point, I realize that things have finally gone too far, especially since Jason is just laughing while Alison is clearly panicking as she’s stuck underneath him. I decide I need to do something, and rather than just telling him to stop, I start moving around to the side of the bed so I can help lift Jason off of her instead. But in the split second it takes me to get into position, I hear Jason abruptly go silent for a second, before half-moaning “Gooooood giiiirl. Oh yes.”
At the same time I hear Jason say that, I see Alison calm down and stop thrashing around. As I’m right at their side now I have a pretty good view, so I look down where Alison’s head is and I can see it moving up and down ever so slightly.
So there you have it, this fucking guy has my girlfriend licking his asshole. What the fuck is going on? If I hadn’t seen it with my own eyes, I never would’ve believed it. My head is exploding with a combination of disbelief, amazement, and a huge rush of sexual energy from seeing Alison do something so fucking degrading.
I’m close enough that I can even see her tongue, and she is making full licks from Jason’s taint all the way up his ass crack, over and over again. He’s a pretty hairy dude, so his ass is like a forest and it looks like Alison must be tasting a ton of these hairs with each lick. I’m guessing some of them are coming loose and ending up in her mouth too. It obviously doesn’t seem to matter to her though as she is working hard to hold her head up enough to keep licking him. Jason is clearly enjoying his end of this experience as he just keeps moaning and telling her not to stop.
After a minute or two of what looks like pure enjoyment for him, Jason starts leaning all the way forward and lowers his head on to the bed in front of him. In doing this, he arches his back and exposes his asshole nice and wide, but it also lifts his ass off the bed a little more. This makes it even harder for Alison to reach him, but it looks like she’s still trying.
It’s at this point I decide to get involved, so I place my hand on the back of her head and lift it up, pushing her mouth right into Jason’s now clearly visible asshole. I’m now able to witness this event in extreme detail and I’m mesmerized. Alison is frantically running her tongue all over and around his asshole as Jason’s moaning increases to an even higher and louder state. Every so often I’ll use my hand to press her head forcefully against him and each time Jason responds with a “yessssss”.
Eventually, Alison starts to tire a little and slows down her licking. I decide she’s probably had enough of this and I allow her head to fall down and rest on the bed. Jason takes a deep breath and says, “Fuck, that was amazing.”
I’m left to realize that time and again, I’ve completely misjudged how Alison was going to react in this whole scenario. I’ve spent a good portion of this escapade worrying that she wasn’t ok, or was going to call the whole thing off, but all my worrying was for naught. It’s pretty clear now that she didn’t need me looking after her at all.
At this point, Alison had also stopped pretending to fight back in this whole rape scenario. She didn’t necessarily seem like a totally willing and enjoying participant, but more like a sex slave who is doing what is required off her. She had pretty much ceased talking once the sex actually started, too. In the beginning, she was saying things to play along with the scenario, but as time went on the only sounds she was making were non-verbal ones related to the sex. The bottom line was I didn’t really know how Alison was feeling about anything, but after seeing Jason get his ass licked by Alison, I started to feel more selfish about getting what I wanted out of this.
“Get up, Alison.” I say somewhat forcefully. As I say this, Jason climbs off the bed and gives me a look as if to say, go for it little buddy. After Jason has gotten out of her way, Alison responds to my command and sits up on the bed.
“Get on all fours facing the head of the bed.” I now command, and Alison does as I tell her. I then motion to Jason and say, “Why don’t you sit against the headboard.” So he moves up and is sitting on the bed in front of Alison with his cock out right in her face.
“Alison, get your ass up and start sucking Jason’s cock.” I say as I’m now directly behind her.
And with that, she starts sucking him while leaving her ass completely wide open for me. I have no time to focus on the blowjob Alison is giving Jason as instead I’m 100% zoned in on the asshole I’m finally going to get to eat. It’s completely exposed, lights are on so I can see every detail, and she’s busy focusing on sucking a cock, so I can finally have the one sex act I’ve desired with Alison since the night we first hooked up.
I can’t wait any longer so I dive right in, spreading Alison’s ass cheeks with my two hands. I start going to town on her sweet asshole as if I’m a starving person presented with a delicious meal in front of me. I immediately start with circle after circle on her rim. I’m quite a bit rougher than I normally would be because I have this mindset of fuck it, I want this and I am going to have it. I start mixing it up with long licks from her pussy all the way up her ass crack, and pretty soon the entire region is sloppy and wet. As I take a second to pull back and admire the view, I can see her vagina still has a noticeable gap from the pounding it took from Jason’s cock. I can also detect more of a musky smell than I’m used to with her which I’m sure can also be attributed to Jason’s junk. I’m not sure if that turned me on more or less, but it certainly didn’t stop my licking.
One of the reasons I had always dreamed of licking Alison’s ass was because I did have experience doing that to other girls. But the fact that Alison was so sweet and cute, and blonde for that matter, made me desire her asshole most of all. And now that I was finally getting my chance, I was able to draw from my past experiences. One thing I always found helpful when tonguing a girl’s asshole is to have her play with herself while I’m doing it. So not too long after I started, I reached forward and took one of Alison’s hands and moved it right to her pussy.
This meant she was now down to only one hand to help with Jason’s blowjob, but what the fuck did I care at this point? Alison took my suggestion and started rubbing her clit while I licked and licked. I continued to spread her ass apart with my hands and this allowed me to start fucking her asshole with my tongue. There was no doubt I was getting inside of her now, and I absolutely loved the thought of me tasting that part of her body.
I could tell she was loving the combination of my tongue and her hand because her breathing started to change. For the first time all night, she seemed to be genuinely enjoying what she was feeling and I realized she might cum. Despite having my tongue in her butt, my eyes were high enough I had a decent view what was going on in front of me. And at one point, I see Alison stop focusing on Jason’s blow job and just rest her head to the side on one of his legs. Jason seemed fine with this as he starts running his hand through her hair, and as he does this, she starts cumming.
I know her orgasms well and she lets out her classic moaning sound that signals one. I close my eyes and stick my tongue as deep as I can get it inside of her asshole. I feel her hand moving around furiously until all at once it stops and holds tight against her pussy. A few seconds later she lets out a huge sigh and collapses to the bed as I remove my face from her ass.
I absolutely love the fact that she just came. It makes me feel so good. It’s mainly the fact that Jason had been in total control for most of the night, and then as soon as I took the initiative, I made her cum. It was such an ego boost.
While Alison had just cum, both Jason and I were still all worked up. I was riding high on confidence, so I kept my assertiveness going and said, “Jason, I think her ass is ready for you.”
Alison was still lying on the bed, still blindfolded, and still not saying much about anything. Jason got up from the spot where he was getting blown and moved over to where I had been eating Alison’s ass from. As soon as he gets there, he uses his two hands to hoist Alison’s hips up until she’s back on her knees again. He doesn’t waste any time as he takes a finger and plows it right into her asshole. Alison grunts, just like the last time he did this, although this time I’m sure there was a lot more lubrication in the area. Jason does a few in-and-outs with different fingers until he’s satisfied with the state of her asshole. He then lines his huge cock up, looks at me, then looks back down, and then starts pushing it in.
It slides in without too much trouble, at least for him. He pushes all the way inside and as he does Alison let’s out a huge “uggggggh”.
Jason let’s out a “Holy fuck.”
Alison doesn’t say anything but she’s clearly uncomfortable. Jason starts to slowly go out and back in and as he does this, Alison starts breathing heavily. She’s not making any noticeable sounds but she’s just taking huge inhale after exhale during this fucking, which to Jason’s credit is still pretty slow and gentle. I’m taking it all in from the side view, still as hard as ever. Alison continues to struggle and look in legitimate pain, so for the first time all night I can’t help myself and I ask Alison about her safe words.
“Babe, you remember the safe words, right?”
Alison can’t see me because of the blindfold, but she lifts her head up as if to look at me.
“I remember…” she says, and then she pauses before grunting in pain. “…the colors.” She then says to complete her sentence before grunting again as Jason fills her ass to its limit.
“Fuck, it feels like a cock ring.” Jason then says as he’s loving every second of what’s apparently his first real anal sex experience. I can’t help myself, so I come over and get a good look at how his cock is stretching Alison’s butthole. It looks incredible as I can see his cock getting squeezed so tightly by the ring of her asshole, and I’m still amazed to this day that it fit.
Yet again, I realize Alison is not going to give in and admit defeat, so fuck it, I figure I might as well play along. I make my way up on the bed and position myself in front of Alison’s face. I lean back, put my hand on the back of her head, lift my legs over my own head and I guide her face right into my ass. If Jason is going to get his ass licked, then I want to get mine licked too.
Now despite my past experiences with ex-girlfriends and licking them, I’ve never actually had my own ass licked. Alison seems to realize what I’m doing right away and doesn’t fight it. She goes right in with her tongue and gets to work. Initially, there’s no doubt the first sensation is pretty weird. But soon enough any weirdness gives way to a very pleasurable feeling. On top of that, the psychological aspect of knowing this sweet, precious girl is doing something that ordinarily she’d consider as foul as can be, is a huge turn on. She keeps licking away and doing a great job. There’s no half-assing (no pun intended) either as her licking intensity and dedication is probably close to how I had been licking her a few minutes before.
Jason sees us and comments how hot it is, and then I start jerking my cock and fully enjoying the moment. Not long after I started touching myself, I hear Jason warn us that he’s about to cum. And sure enough his thrusting turns into a couple of really hard and satisfying pumps and he lets out a “Fuuuuuuuck…” to signal he’s cumming. I can’t help but imagine his cum exploding into Alison’s rectum, and that image combines with my ass getting licked and my own jerking of my cock, and I explode.
Cum goes shooting out of my cock and up towards my head. I think the first rope goes clear over me and onto the headboard, but the subsequent cum shots land both on my face and on my chest. I don’t give a shit though as it’s such an awesome orgasm and incredible release.
Both Jason and I retreat from our huge orgasms and just enjoy the relief. He pulls himself out of Alison’s asshole and just stands at the foot of the bed to collect himself. I drop my legs down, rest my arms at my sides, and close my eyes to savor in the moment too.
Alison also collapses onto the bed from being on all fours but lifts her head up a little. She decides to finally take her t-shirt blindfold off and start looking around the room, taking in the scene. Before saying anything she looks over her shoulder at her ass to survey the damage there by gingerly examining it with her hand. She winces a little from the touch and also reacts to Jason’s cum that is starting to work its way out of her. While doing this, she looks at Jason and says, “Nice to meet you, Jason. I’m Alison.”
Jason smiles and responds, “You have beautiful eyes.”
Alison gives him a sweet “Thank you.” and then turns her head, looks at me and says, “You goober, did you cum on your face?”
“Ha ha ha, maybe I did.” I say mockingly. “I’ll get us both some tissues.”
I grab some tissues from the bedside table and hand a bunch to Alison. She turns herself over and starts wiping up her ass right there on the bed. While she’s doing that, I’m cleaning my face off as well.
“Eeewww” I hear Alison say as she takes the wad of tissues and notices a fair amount of blood mixed in with the semen.
Something about the sight of Alison’s blood and the thought that we caused her a significant amount of pain instantly makes me feel horrible. The fact that I just came and am no longer horny also contributes to the shame I’m now feeling. Either way, I have a mini panic attack and all I can think of it’s time for Jason to go. As soon as I’m done cleaning my face and chest off, I walk over to just outside the bedroom door and grab Jason’s pile of clothes.
I bring them over trying to be as non-awkward as possible about having him get the fuck out, so I hand them to him and say, “That was awesome man, thanks for doing that with us.”
Jason seems a little surprised that it’s such an abrupt end to the night, but he’s a good sport and seems to get the message. He asks if he can use the bathroom, so he goes in there with his clothes.
I look over at Alison with a concerned look and say, “Are you ok?”
“I’m fine.” She says. “Really. I swear.”
“Ok. I’m really looking forward to falling asleep next to you.” I say. “Just the two of us, obviously.”
“Me too.” Alison responds.
Jason comes out of the bathroom fully dressed, looks at the two of us and says, “If you ever wanna do this again, hit me up.”
“Yeah, definitely.” I say as I kind of start walking towards the door to leave.
“Later on, Alison.” He says, and then he and I head out of the bedroom. I walk him to the front door, him clothed, me completely naked, and I show him out. I’m so relieved once the door closes and I come straight back to Alison in bed.
“Oh babe, I’m so sorry, that was way over the top.” I say as soon as I lie down next to her.
“Stop, stop. It was fine. Really it was.” Alison says.
I can tell Alison doesn’t really want to talk about what just happened, so I put my arm around her and close my eyes. I think I fall asleep pretty much instantly. I have no idea if she laid awake recapping everything that had just happen in her head, but my guess is she didn’t fall asleep nearly as quickly as I did. When we woke up the next morning, we briefly discussed what had happened the night before, but didn’t ever go into much detail. I still felt pretty terrible about how we treated Alison, but she always claimed it was exactly what she signed up for, so there was no need to keep apologizing.
So that’s the end of the story of the kinkiest night of my life. Thinking back on it, some parts were pretty fucking hot while others I still to this day feel guilty about. And some moments were definitely both. There was one huge plus that came out of that night, the ass licking. After never having done it before, it became a regular part of Alison’s and my sexual routine. And amazingly, she was into both ends of it, giving and receiving.
While we kept dating a while after that, ultimately we ended up going our separate ways. Our sexual chemistry was certainly never the problem. We eventually realized we had a difference in opinion on whether we wanted kids and a family one day, and that was just too much to overcome. Our breakup went better than most though, so we did keep in touch from time to time.
There was one evening a few years after we broke up when I got a pic over text from her. It was kind of a grainy shot of random people at a bar, and it said, “I don’t think he’s spotted me, but the infamous Jason is at this bar!”
After I read that, I took a second look at the pic and could see there was a guy that looked just like him.
I texted back, “Impressive since you only saw him for like 30 secs that night.”
She texted back, “LOL. Should I hook up with him?”
I texted, “Go for it!” but then got radio silence in return, keeping the mystery alive.
I’ll be honest, I think I spent that night jerking off imagining the two of them going home from the bar and him fucking her in the ass again. But who knows if that actually happened. Knowing Alison, she probably was already dating someone else, because I couldn’t imagine her staying single for long.
What I do know is what happened that night with all three of us. That night taught me a bunch about how weird things can get when you involve a stranger in your sexual adventures. It also introduced me to a number of wife-sharing or cuckold type feelings as well. But most of all, it made me appreciate Alison for being sexier than I ever could’ve imagined.