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[This is a fictional story, written as a commission.]

Hi, I’m Jessie. I want to tell you about the time that I tried to arrange a threesome as a surprise for my husband, Harry. This all happened years ago, now, but I still love thinking about it.

A couple of years after we got married, Harry and I started experimenting with our sex life. We weren’t bored, we just wanted to add some extra fun into the bedroom. We did all the usual things that you’d expect. We tried toys, some light BDSM, and a little bit of awkward role play. I’m not especially kinky, I’m perfectly happy with typical sex, but it was fun to try some new things.

Eventually, it was Harry’s birthday. We spent the day celebrating with a couple of friends at a pop-up food festival. It was great. We ate and drank and watched a few local bands play. Later that night, once we were home alone, Harry and I started making out on the couch. Things got a little hot and heavy and he started rubbing between my legs. I was way too full of food and booze, though. I gently let him down and he agreed that maybe now wasn’t the best time. Instead, we started drinking again.

A few whiskey and cokes later, and the topic of sex came up. We’ve all the time had a pretty healthy sexual relationship; communication has all the time been essential to us, especially in the bedroom. We talked about what we were enjoying in our experimentation and what we’d like to try out. I suggested that I’d like him to be a bit rougher with me, which he was slightly hesitant at (he’s a sweetheart, really), but he agreed to try it out. I asked him if there was anything he wanted to try and he went a bit quiet. After a little pushing, he let the truth out. He wanted a threesome. I was a little shocked, I’d never heard him mention anything like this before, but I let him explain his fantasy. Basically, he wanted to fuck me with another guy. Specifically, a well-endowed guy. I’d never been interested in bringing another person into our bedroom, so after he was finished talking, I broke the news to him, softly. He was definitely bummed out, but he respected my feelings and we left it at that. We spent the rest of the night drinking and predictably passed out.

As the weeks rolled by, I’d occasionally think about Harry’s proposition. It wasn’t really fantasising, more like prospecting. I wondered about the logistics of it; what the bedroom dynamic would be like, how it might affect our relationship, where we’d even discover another guy. I’d never been against the idea of a threesome, it just wasn’t something I was interested in. I was happy with the status quo. But the more and more I wondered about it, the more interesting it began to seem. At first, it was exciting to imagine fulfilling Harry’s fantasy. I’ve all the time wanted to please him and I love how enthusiastic he can be when we try something new. It made me feel good, thinking about giving him what he wanted. But the more time that passed, the more I began to consider what it would be like for me. I imagined what it would be like to sleep with someone new, what it would be like to get fucked by someone else in front of Harry, and what it would feel like to take a bigger dick. I’d all the time been happy with Harry’s size, it definitely did the job, and I’d never fantasised about having bigger. I was more interested in what it would feel like to have two guys inside me at the same time. At this point, it was safe to say that I was curious.

I began to roll the idea around in my head, daily. I’m quite a self-actualised person, so I quickly realised that I was, indeed, interested in having a threesome. Once I was decided, I went into planning mode. I wanted to make up for Harry’s sexless birthday, so this was gonna be a belated sort of present for him. Most importantly, I wanted it to be a surprise. Who doesn’t love surprising their partner? I was gonna plan it on a night where Harry had the next day off work. That way, we could relax alone the next day and reminisce about the previous night’s fun. I was so excited, I knew Harry was gonna love it. I couldn’t wait to see the look on his face.

After a long search, I found a free website for people looking for casual hook-ups. I set up a user account, explaining that I was looking to surprise my husband with a threesome. I wrote out all the conditions I could think of; single, no bareback sex, no means no, be respectful and courteous, good hygiene and clean STI test, and they had to be well-endowed. I was set.

All week long, Harry would watch TV in the evening and I would sit on my laptop in the kitchen, reading the unexpected influx of messages. Boy, there were many. Most were from guys who didn’t meet my stated criteria, but were still trying their luck, anyway. Deleted. A lot of them just wanted to sleep with me, and tried to encourage me to meet them alone. Deleted. Some were from married guys, looking for an extra-marital affair. Deleted. As the week progressed, I managed to put together a short list. I had three guys. Number 1 was almost perfect, except that he was almost a decade younger than us (we were in our early thirties, at the time). Number 2 was also nearly perfect, but he was a busy man and wasn’t sure he could meet me when I wanted (the following week). Number 3 was my last choice, mostly because he messaged me too often, which I found a little needy.

Towards the end of the week, I had decided to settle with number 1. I could deal with the fact that he was in his early twenties, it wasn’t a complete deal-breaker. I just hoped that he wasn’t inexperienced. Once I was certain of my choice, I sent him a photo of Harry and I. I also sent him a very flattering picture of myself, to seal his interest. I was in a fairly revealing summer dress that I wore to a friend’s wedding. It didn’t take long for him to reply and, Christ, he was enthusiastic. We ironed out some of the finer details and I reiterated that it was to be a surprise for my husband. We arranged it for the coming Saturday. We were set.

As soon as I agreed, my nerves set in. I started running doomsday scenarios through my head, imagining all the methods this could go wrong. The last thing I wanted was to disappoint my husband. On Thursday, a couple nights before the dreaded day, Harry was once again watching TV. I decided to go onto the website and delete the profile, as I had number 1’s phone number and didn’t need the profile any more. I sat in the kitchen and logged on. Hundreds of messages again. I wasn’t really interested in watching TV with Harry, so I decided to just browse the rest of the messages before I deleted everything.

Once again, there were just so many crazy messages. One that stood out was from a guy who wanted to wear a furry costume at the meet, which I found hilarious. I was definitely gonna tell Harry about that one, eventually. I had deleted most of the messages, when I came across one from a guy in his fifties. He was a looker, despite his age, and he had a body to match. The fact that he was older was definitely more appealing. He was polite, straight-forward, charismatic, and he had a gigantic dick. It was easily longer and thicker than number 1’s. The stars were seeming to align. I poured myself a glass of wine and mulled it over. Everything was already arranged with number 1 and I didn’t really want to disrupt the plan we had laid out. I decided to send the new guy a message. If he replied while I was online, I’d consider changing the plan. If he didn’t, number 1 was the back up. He replied in minutes.

We started talking and I felt like we instantly clicked. I could just tell that he was more experienced and better suited to our needs. Also, I won’t lie, his dick was an exciting bonus. As we were messaging back and forth, Harry told me he was gonna get some sleep, as it was getting late. I told him I wouldn’t be up too much longer and he walked upstairs. When I heard the bedroom door shut, I poured myself another glass of wine. I was enjoying talking to this new guy. He asked plenty of questions about what I wanted to happen and even made some suggestions, based on his previous experience with hooking up with other couples. I was only a few sips into my second glass when I decided this guy was the one. I filled him in on the finer details and he agreed to everything. Perfect. I sent him a photo of Harry and I, and a few extra ones of me. We exchanged numbers and agreed we would talk further on Friday. I deleted the user account, cancelled number 1, finished my glass of wine, and went to bed with a renewed excitement for Saturday.

On Friday, I got a message from the new guy, Jake. He confirmed all the details again and told me he was looking forward to the meet up. I eagerly replied, telling him I couldn’t wait. I don’t know exactly when it changed, but I had started to get more excited about sex with Jake than giving Harry the threesome that he wanted. I forced that wondered to the back of my mind, though. This was for Harry, not me.

Saturday came and I was a bag of nerves. I got up shortly after Harry left for work and headed into town. After a couple of hours shopping around, I had found a sexy, crotchless bodysuit. I went home and kept myself distracted, cleaning the house in preparation for the evening. The plan was simple: Jake would get to our house at 5pm, an hour before Harry got home, so that we could chat and have a drink, to break the ice. Then, we would both get changed and wait for Harry in the bedroom. Harry would come in, see a note on the kitchen counter that said to go upstairs for some crazy sex, and join Jake and I. He would walk in and see me on the bed in my sexy outfit and Jake sitting in a chair by the bed. Despite the simplicity of the plan, I was still so nervous. I really, really wanted everything to go smoothly.

At about 4.45pm, I was ready. The house was clean and I was showered and in my new bodysuit. I sat in the kitchen, in silence, listening to my heart thudding in my chest. A part of me wanted to call the whole thing off. I’d never done anything like this before and it was wild. But before I knew it, there was a knock at the door. I took a deep, controlled breath and approached the door. I opened it and there stood Jake. He looked so much better than his pictures. He gave me a warm smile, held out his hand, and officially introduced himself. I shook his hand, smiling like a giddy teenager, and offered for him to come in.

We walked into the kitchen and I asked if he’d like a glass of wine. He accepted and I rummaged through the cupboards for some glasses. I sat them on the counter and tried to keep my hands steady, as I filled them up with wine. I passed him a glass, we toasted to the night ahead, and we took a sip. My mind was racing; everything had suddenly become so real. Jake mentioned that he hadn’t expected me to be all dressed up, so early on. A rush of embarrassment coursed through me, and I apologised for not being dressed more appropriately. He quickly put me at ease, telling me that it was a nice surprise, not a shock, but inside I was scolding myself for not being in typical clothes before everything got going.

For the next half an hour, we talked about the evening. He was so laid back and genuine, it really put my nerves at ease. At about 5.40pm, I left a note for Harry in the kitchen, and Jake and I headed to the bedroom. He stripped down to his boxers and sat in a chair, while I laid on the bed. I tried out a few poses to wait in, quickly shuffling around, but it felt a bit forced and silly. As I was trying to discover the perfect pose, Jake mentioned that I looked incredible and Harry would be thrilled to see me in any pose. I thanked him and decided to just lay on my back, facing the door. There was silence for the next few minutes, but my mind was anything but quiet. Nerves, excitement, fear, and anticipation. I literally counted down the seconds until 6pm. After what seemed like an eternity, the bedroom clock ticked over to 6.01pm. I knew Harry must have hit a little bit of traffic on the way home. I decided to fill the remaining time with thoughts on what was to come. I knew that within the hour, I’d have two dicks inside of me. Christ, it was a thrilling wondered. I was also excited to see how happy Harry would be, once he walked through the bedroom door.

It got to 6.15pm and he still hadn’t got home. I was getting impatient, the waiting was absolutely killing me. Eventually, Jake asked if Harry was usually late home from work. I told him that it happened sometimes and that I was sure he wouldn’t be much longer. I waited, listening to every car that drove passed the house, expecting it to be Harry. It got to 6.30pm and he still wasn’t home. I was beginning to get irritated, I wanted the waiting to be over, already. Jake suggested that I message him, to check if he was held up for some reason. I agreed and sent a quick text to Harry, asking when he’d be home. I apologised to Jake, but he insisted that I would be well worth the wait. He just seemed to ooze confidence, sitting in the chair, half-naked with seemingly not a care in the world. I, on the other hand, was wildly impatient. I wanted to get going. I half considered getting started without Harry, but I didn’t want him to feel like I was cheating, by starting without him.

After another half an hour, I was getting far too annoyed. Harry had rarely ever been this late home from work. I let out a deep sigh, venting my emotions. Jake asked if I was okay and I told him that I was fine, just frustrated and willing to get the evening in motion. Once again, he said he was okay with waiting. After a couple more minutes of waiting, Jake asked if I’d mind if he removed his boxers. I didn’t really think much of it and told him that he was welcome to. My eyes hadn’t really left the clock, but in my peripheral vision, I paid close attention to Jake, who was now fully naked. I desperately wanted to look over at him and admire his cock, but I was too nervous. It was silly, we would all be fucking before long, but the nerves were there, nonetheless.

Before long, I could tell that he was gently playing with himself. I could also tell that he was really hard, now. I battled with my nerves and decided to subtly look over at him. Sure enough, he was slowly stroking himself. His dick was unlike anything I’d ever seen. It was as thick as my forearm and probably as long. I caught myself biting my lip and staring for a little too long. My eyes darted from Jake’s dick and met his gaze. We just stared into each others’ eyes, as he continued stroking himself. My eyes fell back to his dick. He started stroking it with more strength, gripping his shaft tightly. It was one hell of a sight to behold. I began thinking that, if Harry’s dick satisfied me, what on Earth would Jake’s be like?

I found myself not waiting impatiently, any more. I was fully consumed by the little show that Jake was putting on for me. He must have been able to tell that I was under some kind of dick-induced spell, as he calmly but firmly told me to come and get a closer look. I didn’t hesitate for a nanosecond. I got off the bed, approached, and knelt down before him. He carried on stroking his cock, looking down at me. I felt like this was bordering on cheating, but as long as I didn’t touch it before Harry got home, it was fine. I was just taking a look.

By now, I’d completely forgotten about the time. I just marvelled as Jake worked himself. After watching for a little longer, Jake stopped stroking and pushed his cock in my direction. My first instinct was to just stick it in my mouth, but I felt bad. I didn’t want to betray Harry, I was doing this for him, after all. I looked into Jake’s unfaltering gaze, then back at his dick, which was still pointing in my direction. I was filled with indecision, looming guilt, and wavering resolve. I was fighting a battle that I knew I was gonna lose. I decided that I would just have a little taste before Harry got back, and stop when I heard him get home. I had made Jake wait for ages, it was the least I could do.

I nervously reached out and took hold of his cock, I could barely wrap my hand around it. I felt a rush of exhilaration, nerves, and naughtiness run through me. I knelt up a little and guided his dick into my mouth. I instantly let everything go. It was a strange feeling. I’d been so nervous before, but now my mind was empty. I took hold of his shaft with both hands and stroked it, as I swallowed as much of his gigantic dick as I could. I’ve all the time been a confident and head-strong woman, but as I sucked away on this older man’s cock, I lost all of that. I felt like an inexperienced schoolgirl, giving head for the very first time. I wasn’t doubting my abilities, I just felt like the power dynamic had changed. He was a hot, older guy and I was now a submissive girl, who would do anything to please him.

I stroked and sucked and licked his dick like my life depended on it. I pulled out all my tricks; I played with his balls, twisted my hands as I stroked, looked up at him with innocent eyes. In that moment, I would have literally done anything he asked of me. Then, I heard my phone vibrate on the bed. Everything came rushing back. I quickly took him out of my mouth and looked back at my phone. I looked back at him, guilt across my face. He made a quick gesture for me to check it. I got up and rushed over to my phone, pulling up a message that Harry had sent me. As I read it, I fell onto the bed, deflated. Jake asked what was wrong. I explained that Harry had to stay at work for the night shift, as the new IT guy hadn’t shown up for his shift. I looked at the clock, 8pm. How long had I been sucking his dick? Jake asked if he should go. I knew he should, I knew it. This was meant to be a gift for Harry’s birthday. I didn’t answer. Guilt just washed over me, as I realised I’d just been sucking another man’s dick for the better part of an hour. This wasn’t a threesome, any more. It was just me cheating. I held my face in my hands.

I heard Jake moving and took my hands away from my face. He was standing in front of me, his fully erect cock hovering over me. I wanted nothing more than to carry on sucking it. I told Jake that I couldn’t, that Harry wasn’t gonna be home, so it wouldn’t be right. He said nothing, nor moved. I told him that we should just arrange it for another day, that it would still be great, next time. Still, he said nothing. Again, I told him I couldn’t, that I didn’t want to cheat and if we carried on it would just be cheating, not a threesome. He continued his silence. Once more, I told him that I couldn’t betray Harry, I loved him and felt guilty, I couldn’t cheat, I couldn’t…

I reached up, grabbed Jake’s thick cock, and took him straight back into my mouth. With a renewed vigour, I stroked the length of his shaft and slid my tongue around its big head. I let out loud, muffled moans as I swallowed as much of him as I could. It was incredible. I felt like such a dirty slut, anyway, but the size of his dick just made me feel even dirtier. Before long, he pulled out of my mouth and moved me into the middle of the bed. I watched as he crawled between my legs and held them aside with his big arms. I felt his tongue melt into my pussy and I just lost it. I swung my head back and started moaning. As good as his tongue felt, I loved the feeling of his big, powerful hands gripping my legs. My moans escalated into light screaming; he was hitting all the right spots, and much quicker than Harry usually did. I was getting lost in pleasure. It wasn’t long at all before I felt an orgasm building. Jake anticipated it, and slid two fingers into me. It drove me over the edge and an orgasm burst out of me, accompanied by a symphony of my screaming.

Jake let the orgasm reach its course and then came up for air. Our eyes locked and he rose over me until our faces met. As soon as our lips touched, I just lost control again and kissed him wildly. I could feel the tip of his cock gently pushing in and out of me, as we kissed. I started to feel nervous again, but a great, amazing sort of nervous. Would I be able to handle him? As if Jake could read my thoughts, he began pushing into me properly. I broke off our kiss and moaned loudly, as I felt him going deeper and deeper. Eyes closed, I was almost holding my breath as he was filling me up. I was thinking that he must be fully inside me, by now, but he just kept pushing. Finally, I felt his balls against me. I opened my eyes and they rolled back into my head, as he slowly drew out of me. I kept letting out loud cries, whimpers, and moans. Once I was empty again, he began pushing back in. I kept saying “Oh, God,” over and over again. I’d never been able to imagine this sort of fullness before. It hurt a little, but it was this weird, great pain. Plus, I was super impressed with myself for taking a cock this big.

After maybe twenty minutes of slow in and outs, Jake clearly felt that I was ready to take what he had. He held my legs wide aside with his strong hands, looking down at me. We didn’t break eye contact, as he thrust into me. I let out a loud scream. It was a shock to take him inside me so quickly and powerfully. He knew I could take it, though, even if I didn’t. He began fucking me like I have never, in my entire life, been fucked before. I came in the first minute, but he didn’t relent or slow down a single bit. I am pretty sure that I was screaming, at the top of my lungs, the entire time he was railing me. You just can not imagine the pleasure.

After, who fucking knows how long, he pulled out of me and told me to get onto my knees. I felt a little dizzy, but slowly managed to turn over and get onto all fours. His hands spread my arse cheeks aside, then I felt him slide into me again. By this point, my pussy was well and truly stretched, and I took him with much more ease than before. He began pounding me, without mercy, and slapping my arse. I continued my whorish moaning. If the neighbours had never heard Harry and I fucking before, they were definitely hearing this. I reached in between my legs and started rubbing my clit. It was instantly too much. Another Earth shattering orgasm ripped through me, and I shook all over as Jake continued to fuck me.

After more heavenly fucking, Jake pulled out of me and got up. He walked over to the bedside table, where I’d left condoms (that we never used) and some refreshments. He opened a bottle of water and took deep gulps. Once he was done, he walked over to the chair and fell into it, breathing heavily. I bit my lip, smiling. It was so hot, seeing him exhausted from pleasuring me. I crawled off the bed and walked over to him. I straddled him, reached behind me to guide his dick into me, and began to ride. He needed a break and I was more than happy to take over. I started slowly, gently bobbing up and down. He reached his big arms around me and gripped my arse cheeks, helping me with my ride. I was happily moaning along with the rhythm, letting out louder screams once he was fully inside me.

Even though I was in love with the hard fucking he had given me before, I was enjoying this slower pace. Eventually, he looked into my eyes and asked me if I liked his dick. I let out a little laugh, in between my moans, and nodded. Then, he asked me if I regretted starting without Harry. In hindsight, of course I regretted it, but in the heat of the moment, I was Jake’s.

“Fuck, no.” I said, and carried on riding him.

From his reaction, he was definitely enjoying being more vocal. He asked me if I would prefer if Harry was there fucking me, instead. His questions were turning me on.

“Fuck, no!” I said, again.

He asked me if I was enjoying cheating on Harry. Yes, these questions were definitely turning me on. I started riding Jake’s dick harder and faster.

“Yes, I fucking love it.” I replied.

Then, he asked me if I was a dirty, cheating bitch. I bit my lip and basically growled at him that I was. We were both clearly loving the shit out of this. We carried on, back and forth, with filthy questions and answers. Eventually, Jake had one of my breasts in his mouth, as his strong arms were lifting me up and down onto his dick. Once again, I was screaming the house down. It was coming, another orgasm. I started demanding that he fill my cheating pussy up and I’m pretty sure it sent him over the edge. He started moaning loudly, which in turn, spurred me on. I started coming as soon as I felt him unloading into me. I watched his face, as he orgasmed, which was just the biggest turn on. We kept up our rhythm until he had completely emptied himself into me. I leaned in towards him and we began to kiss. It was the perfect end to the fuck session we just shared.

After we were done, I peeled myself off of him and went into the en suite bathroom. Jake followed. We took a hot shower together to soak our muscles and clean off, making out with each other a little, as we did. Afterwards, we both got dressed and finished off our evening with a glass of wine, downstairs. Once he had gone, I burned the note that I had left for Harry. Then, I went upstairs and did my best to tidy up and cover the smell of sex. The whole time, I wasn’t really present. I was just reliving the crazy sex I had just had. I was on a real high. Once I was all done, I slipped into bed. It was a little after midnight. It took next to no time to fall asleep.

In the morning, I was woken up by Harry, gently shaking my shoulder. The most intense guilt and shame and fear came flooding in. I felt like he had just caught me in the act, somehow. I tried to play it cool, pretending to be half-asleep, but I was instantly awake. He apologised for not making it home the night before and asked me how my evening was. Still feigning tiredness, I told him it was just a boring evening alone. He took a quick shower, then jumped into bed with me. I was terrified he would try it on with me; I was way too worn out for more sex. Luckily, we just spooned until he fell asleep. Once I got up, I felt really, really terrible. I had meant to arrange an amazing surprise for Harry, but instead I’d been a cheating slut. Needless to say, I messaged Jake and told him it couldn’t ever happen again, then I deleted his number. Over the next few months, I massively overcompensated for my guilt, buying gifts for Harry and putting out as much as I could. Even now, all these years later, I still feel awful about it all.

But, God, that was the most incredible fuck of my life.

NSFW: yes

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