As always, I had my regular meeting on Friday with Steve. However, there was going to be a new addition this week: a chap called Andy. Steve has known him for a good few years and had played with him on a regular basis, but apparently they got out of touch after he moved down to Birmingham and got heavily into the BDSM gay scene. In recent months Steve started playing big-time with my arse, stretching it out, but the plugs have now got bigger — up to 2.75 inches. With this in mind, and Andy having touched base, Steve thought it would be fun to bring him along to a Friday lunchtime meet-up.

Steve introduced Andy to me through WhatsApp, and we set up a group. There were a few video calls and lots of sexual content. I even put on a show for the pair of them one evening, or played with my arse for them both.

Needless to say, we all got fresh, updated health screening checks which came back clear, as the only way to have this sort of fun is bareback.

Knowing what was going to happen on Friday, I took some laxatives on Thursday morning — some quite strong ones as well 😂. I started douching Thursday evening and again Friday morning. Having not had any breakfast, my arse was going to be squeaky clean for them. Along with the douching, I also started stretching my arse that evening. I managed to get up to my 2-inch plug and even slept with it overnight, which was a first for me.

The next morning, final round of douching. As I went into the bathroom I initially found it hard to get my 2-inch butt plug out — all the lube, as you could imagine, had gone. I had to ease my finger (with lube on it) around the base, eventually popping it out and leaving behind what could only be described as a big gaping hole. It wasn’t quite 2 inches, but when I got the mirror down (as it felt like there was still something in my arse) I could quite clearly see a good inch-and-a-half opening that didn’t want to close up. This was a big turn-on for me, as I knew that now my ring could stretch to a point that would make it easier for the guys later to stretch it even more.

We agreed to meet up at lunchtime. He was going to go to Steve’s house and then they were going to head over together. I was super excited about the events, and knowing what Andy was into from our conversations on WhatsApp and FaceTime, I bought a thick leather strappy outfit that had a cock ring and straps that pulled my arse cheeks apart. I put it on in the morning and wore it under my clothes whilst I did some work first thing. I’d even put my 2-inch butt plug back in as well.

My cock had remained hard pretty much most of the morning, getting even harder behind the silicone cock ring built into the leather strapping. When I got a message from Andy in the WhatsApp group chat saying that they were on their way over, I quickly had a mouthful of tea and went back into the house, unlocking the front door (which was the normal case when Steve was coming round) and made my way upstairs to the bedroom, knowing that it is less than a 10-minute journey from Steve’s house to mine.

Sure enough, I could hear the car pull up on the drive and the Ring doorbell go off at the same time. A few moments later the front door went, and I could hear Steve telling Andy that I’d be waiting upstairs.

I heard some shoes come off, then it took a few moments before they started to come up the stairs. Steve was the first one into view in his polo shirt and jeans, but Andy came round the corner dressed in a similar outfit to myself, with a massive raging cock, to which he commented, “Snap — we’ve got the same outfit.” We both laughed and chuckled. That was my first proper glimpse of Andy’s cock; I hadn’t even seen it up to this point as I was normally the play toy on FaceTime, but I was quite taken aback. I thought I had a big cock at 9 inches. At first glance I thought it must have been nine or ten inches, but it was the pure width of it that took me back. Not gonna lie — it must have been the same size as a beer can, but 9 inches long as well. I thought those things only ever appeared on coloured men 😳. Needless to say, I complimented Andy on his massive cock, which he thanked me for, and I did say to Steve he could’ve let me know — to which he was quite flattering, letting me know that my arse would easily take it.

Andy wanted to know if I was going to suck it, which I absolutely agreed to. He quickly got on the bed, up at my end, let me take his massive cock in my mouth, and wrapping my hand round it as best I could. His helmet was just huge, but I managed to get it into my mouth and started going to town on it. There’s no way I was getting that deep-throated; I was looking forward to having it in my arse.

With that, Steve went straight in to playing with my arse, pulling my butt plug out, then commenting, “Jesus, that’s the most open I have seen your arse.” I told him that I’d had the butt plug in from 3 o’clock yesterday afternoon all the way through the night, apart from douching as the only time it would be out. Steve got the lube and started playing with my arse. Three fingers went in quite easily. Next step, I could feel him grouping his fingers together and trying to work his fist inside me. I paid some more compliments to Andy’s cock. It was just absolutely amazing — a lifelong dream, you could say.

Steve carried on playing with my arse for several minutes until eventually I felt a bit of pain and then a sudden sense of having a full back passage, with Steve confirming, “Fuck me, that was easy. I’ve got my whole fucking hand inside you.” I felt Andy’s cock suddenly tighten up inside my mouth, and Andy telling me that they need more guys like me down at his scene in Birmingham. I stopped sucking his cock to agree to his request that I’d love to.

Steve, now with his wrist inside my arse, I could feel him rotating it and starting to pull it back in and out. I was trying to relax even more into the fun, and sure enough I could feel his hand come out and then my relaxed hole let his hand back in again.

With that, Steve took his hand back out and went straight in with his cock, telling me that it probably wouldn’t even touch the sides now.

I could feel it going in, but yes, it was a much more relaxed sensation around his cock this time compared to normal. Steve built up a quick, firm rhythm while Andy grabbed hold of my cock and started wanking me off. As always, Steve doesn’t last very long, and only 40 seconds in he grabbed tight round my thighs and pulled my hips right into him as he firmly rammed inside me, cumming. He did this over about eight or nine deep pushes against me, giving me a pat on my thigh and telling me that I’d been a good boy.

Andy then exclaimed that it was his turn, and how did I want it — on my back or on all fours? I told him I was quite happy on my back so I could watch his excitement.

Steve pulled himself out of my arse and I could feel his cum instantly run down the crack. Putting my legs together and desperately trying to close my ring, it just wouldn’t; I could still feel it coming out. Andy was straight between my legs, lifting them up into the crease of his elbows and pushing them apart, just as Steve got onto the bed next to my head on the opposite side. As I turned to take Steve’s cock in my hand and mouth, all I could see between my legs was Andy grabbing the lube bottle and squeezing a huge amount onto his palm, then starting to slather it all over his massive cock that was still in full view between my legs. As I could see Andy about to start guiding his massive cock inside me, I relaxed into it, with Andy exclaiming, “Fuck me, you’re opening up even more for me — that’s one fucking epic man-cunt you’ve got.” With that I could feel his cock touch my ring and start to spread me. It wasn’t painful, though — that would be down to the work that I’d done the day before and Steve earlier with his fisting — but sure enough I knew he was going in. There was a very tight sensation and I could feel it run over his helmet as he slowly guided it in; even the veins on his cock I could feel as it stretched me. Then a sensation I’d never felt before: his cock hitting the back of my rectum. I looked down and sure enough he was all the way in. I’ve never felt so full in my life before, but it was absolutely amazing. He started off slowly, building up, pulling his cock back out to the tip again and then pushing his helmet back in, and complimenting me on my man-cunt and how easy it was to be fucked. My cock was absolutely rock hard at this point and I had Steve’s now-clean cock in my mouth, with his cum and my own man juices in my mouth, giving him a deep clean.

Andy must have spent nearly 10 minutes (or at least that’s what it felt like) just slowly sliding in and out, every single time feeling absolutely amazing, with pre-cum just constantly oozing out of my cock. His cock was so big that every time he pushed in it was like he was milking my prostate.

It was amazing to watch as he pulled his cock out almost entirely apart from the helmet and then would slide back in. You could literally just see cum oozing out of my cock as if I was almost cumming. He started to build a bit of a rhythm but reassured me he wasn’t one of the pounding types. His rhythm built up slowly to about two or three penetrations every 10 seconds — it was heavenly. He asked me where I would like him to come, and I told him just keep pumping it inside me. Along with Steve’s load, he had been nearly 15 minutes with his cock inside me and I was loving every minute of it, but then he told me he was about ready to come now. With that, he gave a big deep thrust. I could feel his hips meet my butt cheeks and his cock suddenly tighten up inside me. Sure enough his load filled my arse. About seven or eight more deep pumps, trying to get deeper and deeper inside me each time. Luckily years of play and more recent extreme stretching meant my arse comfortably took it.

He then pulled his cock out and all I could feel was my hole left gaping wide open. Steve’s cock was now gone soft. As I saw Andy’s monster finish coming out of me I could feel more of both his and Steve’s cum dribble between my arse cheeks and onto the bed.

Next, Andy started to play with my now-gaping hole with his fingers and worked several of them in, squirting more lube on his hand as he did. He even leant forward and started to suck my cock as well as he was fisting my arse.

At this point Steve had now got off the bed and was getting himself dressed. Normally Steve would probably already have gone by now, as it’s only his lunch break that he utilises when we meet up on Fridays. Andy was quite enjoying himself playing with my arse and sucking my cock. One thing I noticed: his cock hadn’t really reduced much in size. It had gone a little bit softer at this stage, but it was still quite sizable.

Steve asked Andy how long he was going to be, to which Andy replied, “You need to get back off, mate — you do that. I’m gonna hang around here for a little longer. I’m having too much fun with Dave.”

I smiled and chuckled. Sure enough Steve agreed and said to drop him a message when Andy was done and he’d try and pop back later to pick him up.

Andy didn’t even come back up off my cock to acknowledge; he just grunted a yes to him.

Steve made his way out of the bedroom, downstairs. I could hear him putting his shoes on and then out the door, all while Andy was still sucking my cock and fisting my arse. I’d never really been in this situation before with somebody carrying on using me after they’d finished. I was quite enjoying it.

Andy started to build up a bit of pace with his fisting and even getting his hand further out so he was around the widest part of his knuckles. I was so relaxed — it just felt absolutely amazing.

He then came up for air, so to speak, and asked if I wanted to do a sideways 69. I agreed. Still with his hand inside me, we repositioned ourselves top-and-tailing so I could get hold of his cock and start sucking it. It was still big, but I think it had reduced in size to probably about 7 inches, but was still really fat and wide as I took it into my mouth. His cock started twitching as I carried on sucking; I could feel blood almost rushing into it and feel it growing exponentially inside my mouth again.

We carried on our 69 for several minutes. I was used to holding on from my own years of being forced to edge and sit back and get cuckolded by Chell.

He then came up from there again and asked if I wanted to ride him, and I absolutely agreed. Andy pulled his hand out of my arse, which was now feeling like the opening to a large tunnel. I could feel the gape. He laid himself on the bed and I asked him if he wanted me front way or back, and he said front so he could get hold of my cock.

I straddled over him and grabbed hold of his rock-hard cock again, started to guide it into my gaping arse. Sure enough it felt amazing as his helmet, now engorged again, slid past my ring. I could feel his whole shaft ripping through my ring as it entered me. I eventually came to a complete rest with my butt cheeks pressing against his hips, having swallowed up his whole entire cock. I started to build up a riding rhythm on top of it. Bearing in mind he had already come just some 25 minutes earlier, I didn’t think he was going to come any time soon. Sure enough I thoroughly got into the role of it, sliding up and down on his cock. At one point I even got into a squat position and started really sliding up and down on his shaft.

We tried several positions after that, with me turning my back on him and eventually ending up on all fours with Andy off the bed standing up, sliding his cock inside me. It was this position, from half an hour to 40 minutes after we’d started round two, that was the final position. After sliding him back and forth for several minutes — nice two or three thrusts every 10 seconds — he called out he was going to come again. With that he grabbed my hips and pulled me back against his cock, pushing deep inside me as he unloaded for the second time. Four or five thrusts inside me and he was done, really squeezing in tight around my hips then releasing. I could feel him pull his whole cock slowly out of my arse as his helmet cleared my ring. I could feel his fingers running around it as he then slid his hand back inside my arse and pumped it a couple of times before whipping it back out quite speedily.

I complimented what an amazing time it had been and reiterated that I needed to go down to Birmingham to meet up with some of his friends, as they would thoroughly enjoy me as well. I offered him a shower as we’d got quite hot with it being a good hour-and-a-bit session from when Steve had arrived with Andy first off to now.

Andy declined it but definitely said he would be back up soon and would add me into a couple of group chats with some of his other friends. He got himself dressed; I put on my jogging bottoms and T-shirt. We carried on chatting as we got dressed — a lot in common to be fair when it came to the sex scene.

I offered to run him over to Steve’s house as well, which he accepted as that was where his car was. Now, with cum running out of my arse and my ring still not closed up, I got into my car and drove back to Steve’s. On the way there he kept reaching over and putting his hand inside my joggers to play with my cock, and it was still hard. I told him I’d finish myself off later on, to which he asked could he watch it on FaceTime later, so we scheduled the 8 pm slot.

Can’t wait to see where this now takes me on my exploration of fun.