📚 my roommate made me a sissy Part 8 of 11
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My Roommate Made Me a Sissy

My Roommate Made Me a Sissy

by Ahuizotl
20 min read
4.65 (14000 views)
gayhomosexualm4mstraight to gaysissification
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The next week was kind of strange. Aaron and I didn't really talk. Actually, thinking about it we didn't talk at all outside of a handful of words and most of those were casual greetings before I gave him a blowjob. It felt weird to be in a relationship like that where I didn't talk to someone but was sucking their dick on a daily basis.

I would have loved to not do it, but the message he sent was loud and clear. No matter what was going on I wasn't to forget about our deal. After feeling his massive cock slide all the way down my throat, and then some, I didn't want to feel what it was like pushing into my ass with no lube.

So, I continued to give him blowjobs every day. Mostly they were in the morning. I didn't have anything to do and he didn't have anything to do so I figured I would get them out of the way and show him that I would keep my word. It was kind of awkward the first couple of days though. I knocked on his door or saw him in the living room and said hey. He nodded or said hey back.

"Um, do you want to," I never wanted to say it. I always hinted around the word but couldn't bring myself to ask him if he wanted me to give him a blowjob now or if it wasn't a good time. It sounded too fucking weird.

"What?" He didn't look at me. I don't know if he was being difficult or actually didn't know why I was coming to him, but it was annoying and embarrassing. It made me feel like I was asking permission to come suck his dick and he needed to give it to me. Even worse, the alternative seemed to be to just walk up to him, pull his pants down and start deep throating his cock, although he probably would have preferred it that way and there was no way I was ever going to put that in his mind as an option.

"I just was wondering if you wanted to like, you know, get today over with or whatever? Unless you got something going and this isn't a good time?"

This time he actually did turn to look at me. There was surprise on his face.

"Oh. Shit. Yeah. Naw, right now is fine. I didn't think you'd want to go first thing in the morning but, shit, yeah. Come're."

Him telling me to come to him seemed weird, but I don't know why. I didn't let it affect anything though, I just walked over and got on my knees. He reached for his pants but my hands were already on their way and they banged into each other. I gripped his waistline, pulled his pants down and took his cock in my hand. There was no hesitation, I took it deep in my mouth and found it slid easily to the back of my throat and then further. Only a few moments later my lips were pressed against his waist and he was moaning how incredible it felt.

The entire blowjob didn't actually last that long. He wasn't degrading or demeaning at all and didn't make me strip or jerk off while I sucked on his cock. The worst part was the end though, when he did cum with his cock deep in me. Although, oddly, he apologized when I pulled back and coughed and cum ran down my chin. I told him it was fine and got up and went to the bathroom where I had all of my stuff ready for a quick shower after.

The next day went similarly to the first. I awkwardly asked him if he wanted to get the day over with. He smiled, but didn't turn to me this time. All he did was throw the blankets off as he was laying naked in bed on his phone and told me to get at it. I walked over and crawled onto his bed, laying between his legs and sucked him off until he came in my mouth. I only deepthroated him a couple of times, instead bobbing up and down and playing with his balls to coax his orgasm out.

When he did finally cum he groaned deeply and held my head in his hands again, brushing my hair out of my face again immediately after. I looked up at him, his cock still in my mouth when he asked if he could get a picture of me like that.

"Uh, no. I'd rather not," I laughed nervously, wondering if he would insist.

"Really? Fuck, fine. I mean, if you ever change your mind let me know. This is almost over and I'd love to have something to look back on to remember and jerk off too at night."

I gave a nervous laugh and then got up, wiped my lips with the back of my hand and left the room. It was the first time I didn't run to wash my mouth out and brush my teeth, and I didn't even shower before I left the house. Instead I threw clothes on and went to meet Ashley for an early lunch and to hang out for the day with the smell of Aaron's cock in my mouth and I didn't even realize it.

Ashley looked good today. She always looked good to me, but something about having a cock in your mouth and swallowing cum when you're not actually gay makes a girl look that much better when you know there's a good chance you could be fucking her soon. I kissed her immediately, leaning over in the car when she got it. My hand went between her legs and was rubbing my palm firmly before she pushed me away.

"Calm down Tristan," she said with a laugh.

I couldn't help it. She was wearing faux gym clothes, the kind of outfit girls wear to look cute and sexy as if they're going to workout at the gym but have no intentions of actually working up a sweat in them. The way they hugged her body and made her ass look like she was naked got me so hard. All I wanted to was take her back into her place and fuck her until her bed collapsed.

"Fuck lunch, babe, lets go back inside," I was leaning over into her seat and kissing at her neck.

"Ba-abe," she whined and pushed me back with a soft laugh.

"We can't. I told you. My parents are home and if you want to keep being able to handle these goods you're going to have to keep your hands off when management is around. Okay?"

She leaned in and gave me an overly sweet peck on the cheek.

"Now let's go, I'm hungry anyways. I don't suppose Aaron is gone and we can go hang out at your place after?"

I shook my head no.

"Nah, I swear he never leaves anymore. I'm not sure what he does but I rarely go home and have him not on the couch in his underwear or naked in his bedroom."

"What?" Ashley's voice sounded extremely confused.

"What? What did I say?"

"You said Aaron is in his underwear on the couch or naked in his room? Why is he only wearing underwear in the living room and how do you know he's naked in his room?"

Fuuu-uuu-uuuck.

Aaron had slowly started to adjust his clothing habits around the house the further we got into our deal. While he used to just wear sweats and a t-shirt nearly every day he had slowly moved from that, to t-shirt and underwear and then in the last week he'd walk around in only his underwear. Yesterday he had actually spent the entire rest of the day after I gave him his morning blowjob naked. When I left after my shower he was still sitting in the living room with his underwear pushed off his ankles, and when I came home later that evening he was standing naked in the kitchen. He had asked if I minded and I just rolled my eyes and said no.

"You're paying rent, I guess you can dress however you want," I said to him.

He laughed and responded, "careful how you say that. I might tell you how you can dress too."

I had gotten so comfortable with our new arrangement that it felt normal to me. Him walking around in his underwear didn't seem like a big deal, but as I was looking at Ashley with her face screwed up and her looking strangely at me I can see how with two guys living together it would be weird.

"I mean, like, he fuckin does it all the time and I gotta run back in my room and tell him to go put clothes on. I swear he does it just to fuck with me. And he's always yelling at me when I'm in the hallway to not come in his room he's naked. I always tell that I don't give a shift if he's naked and he can stop telling me that shit."

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"Oh," was all Ashley said. She sat back in her seat with her face still twisted a little. Still, thinking the whole thing sounded kind of strange but the excuse I had made enough sense to distract her.

"Oh, guess what!" She turned around enthusiastically.

"What?" I thought maybe she was going to tell me her parents were going to be out of town this weekend or something. I felt my dick get hard again.

"My boss said that your approval finally came through. They're going to call you any day now to start immediately, and you'll be working with me! We can see each other every day!"

"Shit, no fucking way! That's amazing!" I reached over and hugged her.

This was incredible news. I had started to get a little worried as rent was coming due really soon and I needed to be able to pay Aaron for next month. I don't know if he would be as kind to let it slide another month and I'm not sure I'd survive being straight with another month of dick in my mouth.

"So, is there always a manager during the day or can we like, go fool around in the back when nobody is around? Maybe we can fuck in the break room or something?"

"Tristan, oh my god shut up. You're going to get fired after working there for like a day if you say shit like that."

I was joking, of course, but only partially. But she did trigger a thought in me to make sure I was on my best behavior. I needed to make sure I kept this job and the money. I needed to find something better but the motivation hadn't been there. There were so many distractions with the shock of losing my job, making this fucking deal with Aaron, meeting Ashley, waiting to hear back on this job. It was all so overwhelming that I couldn't deal with another thing on top of all of that.

"Alright, where we goin to eat, babe? Not to be too stingy but try to make it fast food. I'm runnin' real low on funds before I start working with you."

She smiled at me playfully, "I want to go to a restaurant though. Don't worry though babe, I'll get this one. I get paid on Friday and since we been hanging out I haven't really spent much money. It's my treat."

A big smile spread across my face at the mention of being paid on Friday.

"Seriously? So if I get the call tomorrow we get paid on Friday? Fuck, that's awesome. I might be able to sneak some overtime in and get Aaron his rent money early."

Ashley stopped me, "no. No it don't work like that. I get paid Friday, not you. You can't get paid in the same week you work, what if you work on Friday, or Saturday, how're they gonna pay you for that day? Come on, babe, you're smarter than that."

She swatted at my arm and laughed as she leaned back in her seat. The smile dropped from my lips. The hunger completely evaporated from me as well as any semblance of horniness. I wasn't going to get paid until the end of next week, which was when next month's rent was due. If I didn't get started working right away I was never going to have enough to pay Aaron. How the fuck was I going to get around this?

The rest of the afternoon was a blur. I let Ashley go on about all of her friend drama and make plans for us for the foreseeable future. I could only offer the occasional head nod or cursory comment, although they were nothing of note. Thankfully she didn't mind and just felt like spilling all of her thoughts while thinking she had someone's attention. My mind was trying to think up a plan.

I couldn't ask him to give me a break, I knew he wouldn't. He would be pissed off and offended and who knows what he would do. Now that we had it out and his rules were set in hard, thick and pulsing reality I knew better than to try and get out of something. The only thing I could think of, the only option that continued to circle back into my mind was coming to him with an offer. Showing him I put thought into it and cutting off his anger by giving him something he wanted.

When I got back to the apartment in the evening Aaron was sitting in the chair completely naked. His legs were spread and his massive cock was resting like a snake along this thigh. The full length hidden behind his foreskin and I could tell from experience he wasn't really close to being hard yet.

"Hey man," he said as I closed the door.

I gave him a quiet nod and stood around the couch along the back wall of the living room. It was the kind of hovering where anyone who was observant could tell a person had something to say but didn't know how to say it, but Aaron wasn't always the most observant person.

I wanted him to ask what was up. I wanted him to say something to pull the words out of my mouth so I could lean back on the crutch I had used so often that it wasn't me wanting this, it was him. He asked me to do this and I had to go along with it. If I start offering up deals and suggestions then it's me asking for it just as much as him.

"Hey man, I uh, was wondering," I kept pausing and stammering as I talked. This was torturous, like when you break something when you're a kid and have to fess up.

"What's up, what're you thinking? You looking to get tomorrow over with tonight, because I'm game?"

Aaron turned to look at me and ran his palm underneath his massive dick, stroking it slowly while eyeing me with a familiarity that made me shiver.

"Come on, bring those DSL's over here and do some work."

"Uh, no, that's not," I stuck my hand up to get him to stop. Him getting turned on and then denied would not help anything for me.

"I, uh, well first off I want you to know that's its alright okay. I thought of something but like, it's not all bad news."

He stopped stroking and leaned back in his seat, "alright, spill then."

"Turns out I fucked up and I don't get paid until next week and I haven't officially started working yet."

I didn't see what I expected. There should have been a furrowed brow and tense lips, but he just continued staring at me and not saying a word.

"Ash said that they're gonna call me any day now to start. That they said they would hire me but I'm just not sure if they don't call soon, that, like, if they don't, like, I'm not sure if," I couldn't say it. I didn't want to know what he was going to do if I did.

"Spit it out, fuck, man."

"I'm not sure I'll have enough to cover rent next week if I don't start soon."

The silence sat over us as he started right through me. I felt weak and couldn't keep his gaze and dropped my eyes to the floor.

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"So you ain't got rent again for next month?"

I shook my head no.

"But you said you got a plan? What is it? And it better not be nothin about being able to pay me half or part and the rest later. You know I ain't about that shit because it's been a month already and you haven't contributed fuck all but your throat."

The last part stung. I felt filthy, like a street whore.

"No, I just, I just thought maybe we could just continue this. This agreement maybe but for like, two more weeks. Until I have it. And you could just, you know. You call it when you want it and I swear, I swear I'll not make a problem. I'll do whatever you ask, I swear."

I felt myself talking way too fast. The words were jumping out of my mouth and I couldn't stop them, as if I was trying to convince myself as well as him and a group of other people. I could do this. It's been almost 4 weeks, what's another 2, right? Then it'll be over. Then I can go back to normal. Right?

Aaron let out a long sigh and leaned his head back, running his hand down his face.

"Man, I ain't never had more problems with a chick then I had with you."

I couldn't lift my eyes from the floor and I fidgeted back and forth where I stood.

"But fuck if you ain't got some amazing fucking dick sucking lips and they worth the wait in pay. So, fuck, a'ight. We can keep this going, you bein my little dick suckin slave for rent money," he let out a laugh and I couldn't believe the sense of relief that washed over me. My heart was racing. I caught myself smiling.

"But that ain't it though T," he caught me and I froze again, staring at him.

"W-what?" I stuttered in response.

"Like, yeah you suck good dick and I ain't exactly bored of it but I need something else. I'm gonna need you to be flexible."

My head tilted slightly and I stared back at him confused. What the fuck could he mean by that?

"I need some variety, man. I love the way you suck my dick but, like I said at the start, the only reason I been doin this is because I ain't had a girl in a while and, I don't know if you see where I'm goin with this but, the more you suck my dick the more I want to feel how tight you are bent over."

Everything in me dropped. My face sank. My mouth fell open and I stared at him in shock, "no, you don't mean?"

Aaron nodded.

I shook my head, "Aaron, come on."

"Sorry, bro. If you're gonna keep this going I'm going to need a step up in what you're offering."

"Fuck, dude, come on. You know that's not cool. It's two more weeks. I fuckin said I'd give you blowjobs for two more weeks, your rules. Come on, dude."

"Don't fuckin say that shit to me, man," he sounded angry but not rageful. Aaron was frustrated and went on explaining himself, pointing at me and laying it all out so I understood what this was.

"Don't forget I'm doing you a favor. I could throw your ass out on the street any time but I was kind. I was forgiving. I let you stay here for free and all it took was a few minutes out of your day. Do you have any idea how expensive those blowjobs you're giving are? Do you realize the rates you're giving me? That's premium fuckin dick suckin, T. Only the best get those rates, so you better stop acting like such a prude and give me some of that ass too for what I'm paying you. Because, make no fuckin' doubt, DUDE, you're my personal whore right now and I'm giving you a roof over your head. So you tell me you're game or start gettin your shit together."

He wasn't yelling and he didn't sound angry, but the sternness in his voice was ringing in my ears. This wasn't him asking me if he could fuck my ass, this was him telling me I was gonna get fucked whether I like it or not. I was either out on my ass or having it filled, it was my choice even if it was the last one I wanted to make.

"Well, whore, what's it gonna be?"

I didn't have any fight left in me. He had beaten me down so thoroughly that I couldn't say no. I reasoned it, the same way I did all along, that it would be over soon. I told myself that he was forcing this on me, so I wasn't gay. This isn't something I would ever choose if it wasn't the only option. All I could do was look down and nod.

"Let me hear you say it," he told me in a calm, yet demanding voice.

"I'll do it. You can do it. Whatever, it's whatever."

"No, it ain't whatever, T. It's shit that you caused and now you gotta reap what you sow. And don't worry, I ain't gonna be a prick about this shit. I'm not gonna be all up in you night and day, but you're on my terms now until you pay up. We ain't re-upping or signing no new contract. You're my whore until you drop down some stacks for rent. When I snap my fingers you're gonna come suck my dick. When I tell you to grab your ankles you're gonna let me squeeze up into that tight ass of yours. And don't act like you don't like it either, the way you was moanin this morning you gonna take to it just fine."

The only thing I could do was nod and look at the floor, until I heard him snap his fingers. I looked up and he was standing, hands behind his head, fingers laced, cock dangling between his legs.

"Come on, now. Seal it with a kiss. Well, and then finish the job."

I shivered, but didn't hesitate. I walked over and he snapped his fingers and told me to stop.

"Crawl," he ordered.

I dropped to my knees and crawled across the living room until I'm on all fours in front of him. His huge dick was dangling above my head.

"Now be a good whore and make me cum."

His cock slid perfectly into my mouth and I sucked on it for the next few minutes. He grabbed the sides of my face and fucked my throat and called me dirty names. When he finished he pulled out and shot his warm jizz across my face, then grabbed his cock and told me to stick out my tongue. He proceeded to slap it up and down on my tongue and across my face a few times. This was the most degrading feeling I had ever felt, even if it was one of the most straightforward times I sucked his dick. He wanted me to feel like a whore this time and no matter how much I brushed my teeth and tongue and washed my face I couldn't make that feeling go away.

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