Page 33 of Sorry

My wish to have someone to curl up with me while reading my books on the couch was granted by the universe. Neither of us knew how to act in a relationship. We haven't talked about it but we were both enjoying each other's company. Nothing was awkward at all. If I was scared of separating from my loveless marriage, losing this thing I had with Sam would destroy me. No matter how new it was.

I couldn't help but feel incompetent when it comes to intimacy so I was spending some of my nights in my room with my laptop, reading up on all things gay. Everything sounded so exciting apart from ‘the prep’ or ‘douching’ but it seemed like an important step.

If Sam and I ever got to be intimate all the way, I wanted to know what I needed to do. I probably should have that conversation with him because I didn't even know if he was a bottom, a top or a verse. Look at me learning all the terms. Am I a top? Well I knew I liked being a top with women but that's because that was kind of a given. Could I be at the bottom? I got to figure it out. I don’t want to embarrass myself.

Two days ago, I took a bus to the next town over because there was a bigger variety of shops, and bought all the ‘supplies’ for my journey to learning if I like being fucked. From the reactions I was getting while imagining things at night, I’d say there is a big chance I'd bend over for Sam before he could even say ‘bend over’. Christ… I’m fucking nervous though… I've never had anything up my ass.

I was sneaking a douche into the bathroom. I didn't want Sam to see it because I didn’t want him thinking I was putting pressure on him to do anything, more than we were already doing. But I needed to figure myself out.

Well shit! I thought, coming out of the shower. That was an interesting experience. Not a very pleasant one but it had to be done, because I bought the lube and a small vibrating butt plug that I read was the best for beginners.

I laid on my bed fully naked and thoroughly… douched. I squirted a generous amount of lube on my fingers then bent my legs at the knees placing my feet flat on the bed. My cock was flaccid. Not even a twitch. I felt so anxious about touching myself back there, that I wasn’t getting hard at all. Taking a deep breath, trying to gather the courage I slowly reached between my legs and placed my fingers on my entrance. It made me jolt because the lube was so cold, I needed to make sure I warmed it up next time.

It was such a strange feeling but I didn’t hate it, so I started circling my finger on and around my hole and closed my eyes. It started feeling good, and I got a bit braver and put some pressure testing the feeling of my finger, almost breaching the entrance. My dick started thickening and I pressed my finger further, slowly sliding all the way inside. Fuck… I like it. It's strange but a good strange. I started moving it in and out and my breath caught.

I grabbed my dick with my other hand and started stroking myself, in the same rhythm as my finger pumping in and out of me. I wanted more, so I added more lube to my other fingers and some to my hard cock, and resumed stroking my dick that was now rock hard.

I placed two fingers at my entrance and pushed against the resistance, when I felt it give in and slid both fingers in, feeling the burn of the stretch but it was not as bad as I thought it would be.

Picking up the speed fingering myself, while jerking my cock, I imagined Sam being the one with his fingers inside of me. I groaned louder than I should.

He was just on the other side of the wall and was hopefully sound asleep. If he heard me, would he find it weird or would he want to come and join me?

In my head, he was two fingers deep in my hole while touching himself at the same time. It was easy to imagine. I have seen his face while experiencing pleasure. I saw him cum twice so far.

“Fuck... Sam…” I moaned quietly. That thought alone made me go faster, just thinking of how beautiful he was when he let go.

Taking my fingers out, I grabbed the plug and coated it in lube and went back to stroking my throbbing cock. I turned on the vibration on the plug and pressed it inside me. It wasn't any bigger than my two fingers, so I didn't feel any resistance at all. Oh fuuuuck. The vibration felt so fucking good. The plug, even though small, was making me feel so full and I was loving the feeling. I started fucking myself with it and I felt myself getting closer to the edge, fast.

Squeezing myself harder, rubbing my thumb over the head of my cock smearing precum with the lube, I went back inside my head to think of Sam and imagine him bending down and taking my dick into his mouth while he fingers my hole… and that was all it took. My balls drew up and I started cumming, my stomach tightens and an orgasm barrels through me, taking my breath away. I came with the image of Sam swallowing my cock looking up at me with his beautiful big eyes. Shit… I got my answer… I am definitely up for being bent over.

CHAPTER 37

SAM

All of the paperwork had been finalized. The house was now in my name, I was the official houseowner, same with Baka’s savings. Jake and Matt were coming over this evening, after they finished work to make plans about what needs to be purchased for the renovation and to just hang out.

Now would be a great time to unbox the beanbag but it's huge and vacuum sealed. I didn't know how I would manage to do it all alone but I didn't want to bother Alex. They were still hard at work downstairs, so I would have to figure it out.

Dragging the huge box to the middle of the living room, wondering how the fuck did the delivery guys bring it up the stairs. Managing to open the box with the box cutter, I disposed of the cardboard first to make room and ended up standing there and staring at this ginormous cylinder, wrapped in the clear plastic so tight I felt like if I touched it it would explode. It looked angry, wrapped so tightly, the same way as when they rolled and wrapped mattresses to ship.

I'll be fine right? It's just a bean bag for Christ's sake. “OK!” I squeaked out loud to myself, “Just cut open the plastic and it will just unroll.” Making a small cut I felt the whole thing move a bit. “Yeah, piece of cake.” Gathering some courage, I cut some more. I heard a hiss of air coming out of the package. When the plastic wrap ripped it just flew open knocking me on the floor. My fucked up ankle that Kyle broke that one time twisted, lancing pain shot trough my foot up my leg…

“Shit! Shit! Shit!” that fucking hurt like hell. Looking at my attacker, splayed on the floor like a rag doll and scowling at it I cursed myself for attempting to do this on my own. Damn it. It is not even close to where I needed it to be.

Getting up I placed the weight on my right foot and screamed in pain falling forward directly onto the cursed bean bag. “Motherfucker!” I grabbed my ankle. It hurt so bad, it felt like someone was pushing a hot poker into my foot. Pain radiated all the way up to my knee. How the fuck am I supposed to get up and make food for the guys now? They were meant to be finishing up any time now. Just as I thought that, I heard them walking up the stairs.

“Oh! That bean bag is huge, man. Look at that!” Jake exclaimed, being his rambunctious self.

Matt approached me and noticed I was holding my foot. “What’s wrong Sam!?”

Alex appeared out of thin air, concern written all over his face, almost knocking Matt off his feet to get to me. He climbed onto the bean bag on his knees looking over me assessing me from my head to my toes. “What happened Pup? Are you hurt??”

Matt and Jake looked at each other and I saw out of the corner of my eye Jake handing twenty bucks to Matt. That was weird.

“I think I twisted my ankle pretty badly. I don’t think it's broken but I can’t put my weight on it.” I said, gritting my teeth.

“We need to get you to the hospital right now. Tell me what you need me to do.” Alex said, looking panicked.