Following on from my previous story, a lot of people have asked what happened the second night, so rather than try to explain over and over, I figured I may as well post it. I didn’t include too many details about the second night before because the sex was a little more explicit than the first. But the response I’ve had to the first story has given me the confidence to be open and share with you all.
“A quick recap for new readers: My boyfriend and I hosted a friend during the lockdown—a friend who was stranded in the country after six years in Dubai, bouncing between temporary places until he could get a flight. He was supposed to stay a week. But on the last two nights of his visit, fueled by alcohol, the lines blurred, and we shared an unexpected threesome. The invitation was extended again on his final night with us. This is what happened during that second evening.”
Once again, we got into bed, and the scenario was nearly identical. Ryan was already going down on me when he paused and casually asked if I wanted to do it again. I said yes, but with one condition.
“Only if you’re more involved this time.”
We texted Matt, and he arrived in just a couple of minutes—his quick appearance making me wonder if he’d been secretly anticipating the request. This time, there was no awkwardness. Ryan immediately put me into doggy position and began having sex with me while Matt stripped and came straight over to my head. It was much easier to go down on him this time, and I made sure to do a better job than the rushed encounter the night before.
They didn’t just stay in one spot for long. We experimented, swapping positions as a group. The sensation of having all that focused, demanding attention on my body was amazing, totally consuming my senses. Ryan would pull out and grab my hips, twisting me around so Matt could take his place, or they would signal a transition, guiding my body from one man to the other.
I noticed the distinct change in techniques right away. Ryan’s movements were familiar, tender even in their force, while Matt was more raw. At one point, I climbed on top of Matt and, unlike the reserved, tentative movements of the first night, I rode him properly, exactly as if he were Ryan. I was confident and completely uninhibited, reveling in the friction and the sight of my boyfriend watching me on his friend.
Eventually, Ryan guided me off Matt and moved me into missionary. I started focusing on going down on Matt again who had positioned himself by head. That’s when I heard the clicking noise of a bottle of lubricant. I knew what this meant, and even though this was normal between me and Ryan, I hadn’t considered we might do it in front of Matt.
Matt knew that Ryan and I engaged in anal sex, as Ryan had over-shared it when we were talking about our sex life the night before. I wasn’t sure if I wanted Matt to see me like that, but then again, I didn’t expect to be having my second threesome with him in two days. If they had asked beforehand, I’d have probably said no, just to save some level of innocence or boundary in the act.
I felt him start to position his cock against my ass, confirming what he wanted to do. Part of me felt like it was a boundary too far, but in that moment, it gave me the same level of shocking excitement the first night had brought—being with someone else. As anxious as the idea made me feel, I couldn’t resist the urge to go along with that same buzz as before. To some degree, it was small relief for my vagina to have a break, as I was starting to feel overly sensitive after the last 40 minutes of two guys relentlessly competing to satisfy me.
Once Ryan started anal with me, I again felt as exposed as I did when Matt first walked in and saw me naked the night before. I couldn’t help but look up at him to gauge his reaction. I could see his eyes were fixed on watching me take it in my ass.
I tried my best to refocus his attention on me by pulling his dick closer to me to make it easier for me to blow him. It seemed to work, as when I looked up again, I could see he was once again focused on me sucking his dick.
It didn’t feel like long before Ryan pulled out of me and moved into Matt’s position as they swapped once more. This transition was different from all the others up until now. When they swapped positions, I felt the sharp buzz of anticipation, even though I thought we were past the point of shock after two nights of taboo sex. I was unsure what Matt would do. I thought he might be more conservative and put it back in my vagina. He didn’t. Someone I’d only met a week ago was now pressing his cock against my ass. As much as I should have grabbed it and redirected it, I was swept away by the situation again. Instead, I continued to focus on Ryan as he pressed his cock against my ass, a silent signal—I wasn’t saying yes, but I wasn’t saying no either. I was leaving the decision entirely up to him. He tried about three times; each time it slipped back into my pussy.
After the third attempt, I found myself reaching down to grab his dick and position it for him. I remember a tingle running down my body when I felt it eventually go in. I couldn’t help but look down to see it in my ass, a sort of shock and arousal at the same time. Then looking up at Ryan to see how he was reacting. I looked up to see my phone in his hand. Pointing the phone down at me while his friend fucked me. Yet another layer of control stripped from me. We had recorded ourselves multiple times, but the rules were that it had to be on my phone always. So I couldn’t At least delete it later if I didn’t like it.
Soon, I stopped concentrating on Ryan entirely, just holding his cock while fixing my focus on Matt. Ryan eventually pulled away, leaving Matt and me to it, similar to what happened the previous night. Matt then pulled me down the edge of the bed and closer to him, placing a pillow under my ass to tilt my hips up. Pressing my legs to my sides, he pushed in deeper than I’d had anything in there before, which I responded to with a breathless, “Fuuuck.” That was the first time I’d physically noticed his greater size over Ryan’s.
Anyone that has experienced anal sex will know that it’s not so much the physical feeling but the mental stimulation that comes with allowing someone to use your body like that. I’d only tried it once before Ryan, and it wasn’t a good experience. Because he was really into it, I learned how to do it and ended up being able to enjoy it. It’s something I’ve found can be so intimate with someone you really trust. Doing it with Matt was a completely different experience. It was the vulnerability of letting someone who hasn’t earned that trust gain access to you in that way. Combined with the heightened risk of your boyfriend watching you let someone do this with you, the whole situation was sexually overwhelming to the point it just took over my entire body, and I completely leaned into it.
Once Matt could see I was okay with it and Ryan hadn’t interjected, he let his ego take over and started to pick up the pace of our sex. The feeling of how deep he was in me and the transgression of the act made me feel the naughtiest I’ve ever felt in sex. It was filthy, deeply taboo, and I was secretly—or visibly and perhaps not so secretly—loving it.
I couldn’t believe how we had got to this point. Two nights previous, we were talking about how he met his girlfriend, with him showing me pictures from their last holiday before Covid hit. Forty-eight hours later, we were fucking for the second time, and now he had his dick in my most intimate place while my boyfriend watched from the side.
When I first met Ryan, it took him about six months before I’d even let him put his finger in there. Now, with Matt, he’d bypassed all my boundaries (consensually) to the point my body language was encouraging him to go further. I’d always been a sensible girl that enjoyed sex but wasn’t an easy lay. I’d never even had a one-night stand before, and I used to criticise my friends for such things and I used to hate the term ‘slut,’ but all of a sudden, in these moments, that’s exactly how I felt about myself. That feeling made everything even more arousing. I felt like I was performing for them both.
With my hand now free from Ryan’s dick, I tried to resist playing with my clit to continue to be as submissive and sexy as I could be. I managed to do so for a while before I ended up giving in and started playing with myself. I managed to limit myself to a few seconds before using all my willpower to put both my hands back above my head, gripping the mattress to show him he had full control of my body.
I’d only ever had one anal orgasm before without stimulating my clit. Usually because I couldn’t resist the urge to play with myself when we did anal. As I fell into a spiral of pleasure, pain, and a deep feeling of taboo, I could feel my body and especially my mind begin to get overwhelmed. Instead of fighting, I relaxed into it as I felt my legs start to shake against Matt’s grip. My back began to arch uncontrollably as my sensitivity increased down there, my body’s futile attempt to reduce the sensation. Matt, however, caught on to my situation and doubled down on the pressure, pinning my legs back to my sides to keep my hips tilted up towards him, allowing him maximum penetration into me. He switched to harder strokes, pausing as he pressed as far into me to create as much pressure as he could. It sent me over the edge, and all my brain could respond to every stroke was an exhausted “Fu**k,” as he released the pressure of his cock burrowing into me.
Once my orgasm had begun to subside, my mind flickered to the thought of how Ryan might be feeling at this point. Had I allowed it to go too far with Matt, and maybe now he was regretting it?
I managed to peel my eyes open and look toward him. As I searched his face for any hint of disapproval, Matt, still pounding relentlessly, forced my breath into ragged gasps.
His face was still lit from the screen he had pointing down at me.
“Wow!” he murmured, a huge grin spreading across his face.
“Did you like that?” I whispered back, my voice probably sounding strained and awkward, needing the confirmation that he approved.
“You’re amazing. Keep going.”
Suddenly, my feeling of dread vanished. He wasn’t upset; he was explicitly turned on by watching me being this naughty. He was the one who started the anal and then swapped with Matt after only a couple of minutes. Maybe this was exactly what he wanted to see. He was obviously turned on by it all. Maybe this was his way of reaching another level of excitement with me in our sex life. All of these thoughts happened so quickly that I went from dread to a relaxed, calming feeling that I was doing exactly what he wanted me to do.
With Ryan’s permission flooding me with confidence, I twisted my focus fully back to Matt. He was still deep inside, breathing heavily. For the first time, I spoke a command directly to him.
“Cum for me,” I demanded, gripping the mattress tighter and holding his gaze.
I started to tease him by tensing my ass muscles around his cock. He got the message instantly. Reasserting his control by pressing his dick into me with all his weight.
“Fuck me like that,” I requested.
He strokes had slowed as he pulled out then pressing back into me and pausing as he tried to make me submit.
I remember it taking maybe a minute before Matt’s body started tensing up, just as it had the night before, making it obvious he was about to cum.
In a surge of impulse and in this new frame of mind I found myself in, I knew exactly what I wanted. This was the first time throughout the two nights that I took complete control of the situation. I didn’t wait for a signal or an invitation.
I lifted my head up toward him and spoke with a commanding tone, “Cum in my mouth.”
He quickly pulled out, moving my leg out the way to move towards my face. I sat up towards him to make sure we caught the moment as I wrapped my mouth around the top of his dick. It took only a second or two before I felt the muscle in his dick start to pulse against my mouth as he began to cum. I distinctly remember thinking, “Was that it?” I didn’t feel much come out. After how much came out of him the night before I was expecting something different from the small amount I felt shoot into my mouth. I placed my tongue against his hole to tease him when the rest of it shot into my mouth, covering my tongue in his cum. The familiar taste, yet distinctly different from Ryan’s. Another boundary I usually kept only for Ryan, but this time I had violated it myself.
For the first four days, I was just another ordinary girl passing through his life, presenting a polite, friendly self that was entirely forgettable. In one moment, we were casually joking about how he hadn’t even been able to masturbate for the last six weeks due to being stuck in other people’s homes; in the next, less than forty-eight hours later, he was finishing in my mouth. He would never have guessed what lay beneath the polite veneer. I would never have guessed!. I felt a wave of guilt that he probably thought I was some sort of slut now and would always think that when he saw me
The instant the adrenaline faded, the secret we shared became heavy. I knew he had a girlfriend and a life back in Dubai, and It suddenly felt less like a crazy one-off experience and more like a potential liability. Our silence was suddenly broken, not by panic, but by Matt starting the post-sex banter.
“You’re a lucky guy if you get to do that regularly,” Matt said to Ryan, his voice still ragged.
“She’s incredible, isn’t she?” Ryan replied, clearly basking in the shared praise.
Matt then looked back at me. “Was that good for you?”
I gave him a tired, but genuine, smile. “It was fun.”
“You’re the only girl that has taken all of me in their ass,” he confessed.
I giggled, not sure if to be flattered or embarrassed by the shock in his voice. “Really?!”
“Yeah, that was unbelievable !”
I felt a little wave of embarrassment wash over me, instantly replaced by a weird sense of pride. “Thank you, I don’t think I’ve ever had anything in there that deep before,” I admitted.
Ryan grinned. “You smashed it, babe.”
I felt the need to interject. “We’ve never done this with anyone before.”
Matt then abruptly sat up, the casual conversation instantly replaced by cold reality as he looked toward Ryan.
“You didn’t get my face in that, did you?” he asked.
Ryan shook his head quickly. “Nah, you’re good. Don’t worry no one is ever seeing this.”
This instantly gave me an overwhelming feeling of relief. Ryan had no intention of any of this getting back to him or especially his girlfriend. And I was sure Ryan didn’t want it to get out that he let his friend have sex with me in such an intimate way. And I, of course, had no intention of anyone finding out. So I was happy everyone appeared to be on the same page without anything really needing to be said.
After Matt had gone off for his shower, I turned to Ryan.
“What did you record?” I asked.
He told me, “About four minutes of you moaning while Matt was pounding your ass.”
“Did you?!” I giggled fairly nervously
“Yeah, you were loving it”
I grabbed the phone out of his hand and we watched it back, and I couldn’t believe how turned on I was by seeing myself like that. I’d seen videos of me being fucked by Ryan plenty of times but I’d never seen it from the perspective of someone else recording. Knowing in this video was my boyfriend recording his friend fuck me in such an intense way was quite a feeling.
Watching his dick pulse on the camera as he came in my mouth reminded me of how this had happened only minutes ago and I could still taste him.
We never repeated that particular act, but the clip itself became a potent fuel, and we often watched it during sex as a huge turn-on for us both. When Ryan was working away, he occasionally asked me to send it, but I never complied, needing to keep that singular piece of control. This was hypocritical, I knew, considering I had certainly gotten off to it myself on the few occasions Ryan wasn’t there.
I never saw Matt again after that night. I deliberately stayed in bed until his morning flight to avoid any conversation about what had happened. I was relieved he never tried to add me on Facebook; I didn’t want any additional link back to that night. Yet, it always felt strange whenever Ryan posted pictures of us and I’d notice Matt had liked them. They seemed to have remained friends, utterly unaffected by the whole event, but I’m certain every time Matt saw my face, he was taken back to that evening.
Ryan and I mutually broke up over a year ago. We remain polite, checking in on each other now and then, but that single weekend will forever be the craziest of my life. Enough time has passed now that I felt safe sharing it here—it’s not a story you tell people in your everyday life.
And to be clear, Ryan and Matt are not their real names, for obvious reasons.
I hope you all enjoyed reading this as much as I’ve enjoyed writing and reliving it.