I hope this fits in here, it's a bit tame next to everything else but it did for me.

A bit of background: I'm single, I (33M) dabble occasionally in self-bondage, usually with toys and a little cross-dressing. I usually take some kit when I'm traveling because I always get in the mood and it's easier to play without getting disturbed.

I'd recently bought a new butt plug, that kinda undersells the thing, it must be about a foot long, tapers towards a narrow point and it's got a flared base. I hadn't used this new plug - which we'll call the tentacle, it isn't styled like one but it reminds me of one - because honestly I was a bit intimidated, I decided I'd bring it for this trip.

On the night I had been out for dinner near my hotel at Albert Dock in Liverpool and I was already in the mood when I got back. I laid out my toys on the bed: my new tentacle plug, a smaller glass plug that I had some experience with already, my favourite dildo (maybe about 8', with a suction cup and, oh yeah, it ejaculates), some rope, my cock cage and a change of clothes (a bra, shiny briefs which zip all the way around and fishnet stockings). Oh and a plastic sheet, I knew you'd was going to be messy. I had the necessary lotions too: lube, toy cleaner and fake cum for my dildo.

My first act that night was to practice my BJ skills (I'm heterosexual- but a good sub needs to be flexible, right?). I got set up with the glass plug and my cage and got dressed. I tied my torso in a simple karada, making sure it was nice and tight so I would feel every movement. The only place I could stick my dildo was the tall mirror on the wall, then I put the sheet on the floor to catch my drool.

I got on all fours (might have put the dildo a bit low) and started sucking, gently at first. When I play like this I set a random target for how many times I go down on the dildo, tonight it was upwards of 400. Slow, gentle sucks turned into faster, more forceful sucks and I tried to deepthroat a few times too, that just made me gag. But it was hot, and every time I pulled away I felt my ropes pulling at me and pushing on my butt plug. I wished my dildo would cum in my throat, but it was too early for that (and the fake cum is vile and I don't think it's suitable for oral - I use it more for glazing).

My second act: Blowjob completed I went on to the main event, my tentacle butt plug. I put the plastic sheet on the bed and got undressed (mostly, I was still wearing my stockings) I undid my ropes and took out my glass plug. I hopped onto the bed with the tentacle. I stared at it for a while, it's a rose gold colour, silicone, with a measure down one side, I guess so you can see how far you've taken it.

I tried a quick BJ on it too (rude not to), it was weird feeling it in my throat, that didn't last long before I gagged on it. I pulled out out and lubed it up; I was nervous and hard, I could feel my cock bulging against its cage. I slid the tentacle into my arse. It was a bit fiddly at first because it's really floppy but once it was in it was easier. I'd been warned not to try to take the whole thing on the first go but I was much too horny for that, I kept pushing, gently at first but harder as I felt more resistance.

Next thing I knew, it was all the way in.

I was a bit disappointed, I thought this was going to be a challenge, something I'd need a few shots of to get it all the way in, but there I was on my first go with the tentacle's flared base snuggly between my cheeks. I spanked myself a few times and moved around so I could feel it. It felt great inside me, but I wanted more. This is where I got carried away

Surprise third act: I wanted cock. I filled the syringe on my dildo with the fake cum solution, then I gently drew the tentacle out and cleaned myself up. I took my dildo back to bed and proceeded to fuck myself senseless with it.

That was the idea anyway, he's a big boy and it took me a few squirts of lube and and a bit of screwing to even get a little bit of penetration. But I kept going, more lube, more pushing, twisting and turning the dildo in my arse to get deeper until I felt his balls against my cheeks. More lube, longer, faster thrusts, I didn't want to stop! I kept going, harder and faster until I felt myself ready to cum, I reached around for the syringe and squeezed the trigger and filled myself with fake cum.

I lay there for a moment, trembling at that incredible experience, that was my first time doing anal properly and a cream pie too. It didn't take me long to cum after I took my cage off.

I cleaned my gear and tidied up before I hopped in the shower, still shaking a little, before settling down with a cup of tea (British, innit).

This has turned into a text wall, thanks for reading if you've made it this far. There is one more thing, I felt good until the next morning when I had a four-hour drive and I was still a bit tender from the night before. Whoops.