Conditioned Part 2

It wasn't until a few days later when I was headed back to his place for more conditioning that it dawned on me. We never actually exchanged names. I only knew him by his screen name, takingudeep, which was at the same time weird, a little uncomfortable, and kinda hot. I had met a guy online and was having him build associations in my brain between sexual pleasure and getting fucked, but I didn't actually know his name. There was definitely something hot about that as part of the transformation fantasy, staying relatively anonymous even though we were doing it in real life. In the meantime, he was just in my contacts as takingudeep.

When he texted me about what time to come over, he also asked if I could bring him a latte from the coffee shop we had met at and he'd pay me back when I was at his place. Considering the coffee shop was on the way between our apartments, it was no trouble for me to grab his drink for him. I knocked on the door when I got there, and he cracked it open a few inches to beckon me in. He greeted me in nothing but a towel, his torso slick with the sheen of just having showered. He wore that towel well. I handed him his coffee, trying not to stare too intently at the bulge under his towel. Or his abs. Phew. It was getting hot in there.

"Thanks man!" He took a sip. "Mmmmm, this is great. Oh! I should probably dry off before we get started."

I took that as my cue to get ready for this bottom conditioning session and stripped, waiting patiently on his bed once I was in the buff. He came out of the bathroom naked but less shiny, and he had the same 6" dildo from last time and a bottle of lube in his hands. When he saw me lying on his bed, already in position, he laughed.

"Someone's an eager bottom boy," he teased, popping the lube open and coating my dick. Once I was rock hard, he started coaching me through the process, same as last time. "Ok, now just close your eyes and focus on your ass. Just think about how good it feels to get filled up."

I thought back to the dildo filling my ass and hitting my prostate. As I did, his lubed up finger hit the spot and dick jump.

"Yeah, you remember how good it feels being full, getting fucked. You want that dildo back in your ass again. It'll feel just as good as the first time. Better even."

It was true. Last time was so surprising how good it felt having my ass pounded by that dildo that the memory stuck with me really strongly. I really was getting eager for him to upgrade from fingers to the dildo.

I didn't have to wait very long. He seemed to be moving a bit faster, and part of it might have been the way I was spreading my legs to loosen up my ass a bit. The discomfort when he went from one finger to two was almost nothing, so he only went a minute or two before he grabbed the dildo and started sliding it in and out of me. I groaned when I felt it, that fullness hitting me and triggering a memory of my last orgasm at his hands.

"Yeah, it's ok to moan. You know having your ass filled is like nothing else you've ever felt. Getting fucked is pure pleasure. You need your ass filled. Say it with me."

"Getting fucked is pure pleasure. I need my ass filled."

I felt a sort of dirty thrill saying it, but he changed his stroking technique slightly when I did, and it sent a new sexual rush through me. He had me repeat it several times, and with each repetition he manipulated my cock the same way, sending jolts of pleasure through my cock and ass. I was starting to really love getting fucked by that dildo. And then he pulled it out. I hadn't even cum yet, and he was taking my dildo away from me. When it was gone, I felt this odd sensation of emptiness, like my ass had gotten so used to the dildo that it felt wrong not to have it in there. I was about to complain, when I felt something else pushing its way into my asshole. It felt like the dildo, but it was warm and fleshy. And it was bigger. Fuck was it bigger. I opened my eyes and saw him starting to fuck me himself. The dildo was to my right on the bed, and he had the tip of his cock inside me.

"Fuck! How big are you?"

"Nine and a half. Maybe twice as thick as that dildo. Just relax. Close your eyes and keep telling yourself how getting fucked is pure pleasure. You need your ass filled."

I took his advice, and at the very least the mantra took my mind off being stretched wider than ever before. After maybe a minute, he had my cock back to full mast and his cock all the way in my ass. He just stood there for another minute, letting my ass get used to the increased size, and then he began to thrust in and out. Between his constant ministrations on my cock and the feeling of a much larger object ramming into my prostate, I really started getting into it. I started moaning again, which made me even harder when I thought about it. Until this week, I had been a total top, and now here I was on my back on another man's bed, getting fucked and moaning in pleasure. Well, getting fucked IS pure pleasure, I chuckled to myself.

I couldn't really keep track, but I think he fucked me for another twenty minutes before he got me to the very edge of orgasm. My cock was throbbing and pulsing, and we both knew I wouldn't come down from it. I was going to cum. One second before it happened, he took his hand off my cock and just buried his own cock to the hilt. I had a nine and a half inch cock all the way inside me. Fuck. I came really hard then, with that thought still etched on my brain. I'd been fucked by a nine and a half inch cock. And after I started cumming, he pulled out and blew his own load on my stomach along with mine.

I lay there panting while he wiped all our cum off me. I had had plenty of really good sex, but this was an entirely new experience. I could feel myself growing to enjoy it more and more the more I thought about it, and my ass was starting to send signals to my brain asking to get fucked some more. This guy was good.

Finally clean, I put my clothes back on and we sat on his couch to talk about the conditioning so far. I told him I was enjoying it, and he smiled.

"I have a surprise or two in store for you, if that's alright. We can go full disclosure if it's not, but I always liked the idea of taking a guy to new places that he didn't know he'd enjoy."

To be honest I was a little worried about the possibility that I wouldn't know everything he was planning for me, but I did ask him to help change me without any specifics in mind. And on top of that, my transformation fetish was screaming at the rest of my brain to just let him do his thing.

"I think we can just see where things go," I told him. "Everything so far feels fantastic, so I'm sure you can manage a hot good transformation."

"Awesome! You want to come back next Tuesday for another session?"

"Yeah, that sounds good to me. Although, I don't know if I can bring you coffee next time. You still owe me for today," I teased.

"Dude, I totally forgot!" He pulled his wallet out of his jeans and pulled a bill from it. "All I have is a ten."

I accepted it, reaching for my own wallet to give him back the difference, but he stopped me.

"Keep the change. Seriously, you've been awesome always coming here for our sessions, so just keep it. It's what, like four bucks? Not a big deal."

I pocketed the ten, not wanting to push the subject, and then headed out with the promise to come back for more on Tuesday. Maybe I'd get my own dildo in the meantime. Although I had to admit to myself that his cock felt a whole lot better than the silicone substitute.