Roommate to Sissy

Disclaimer/Author's Note: As always, this is completely fictional. I'm just trying to write the little fantasies that go on in my head. If you enjoy them, please comment, I leave hearing from people enjoying it.

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After the encounter with Amy, she barely said a word. She cleaned up, changed, and went back to work. I wasn't sure what to do, so I tried to go about my day normally. I actually did the laundry this time and I worked for a while, trying to distract myself. That said I kept the panties on like Amy had ordered. I would go for bits of time without realizing I had them on until I had to adjust. Then I would blush, a little embarrassed when I felt them on me. If I was honest, though, I liked how they felt. Sure they were tighter than boxers, but the material was so soft that it felt good. For some reason, the thong didn't bother me either, which really surprised me. That I absolutely expected to hate. As the day went on though it phased me less. Once or twice I did notice however that I started to get a hard-on just from the silky fabric rubbing my cock. Each time this happened I would adjust and try to focus on work. Fortunately for me, there is literally nothing sexy about my job.

Despite how positively my adventure with Amy had gone earlier, I kept expecting to get a call or a message telling me to leave and never come back, which did lead to some nervousness throughout the day. It was the silence that was killing me, she hadn't said a word before she left and I hadn't heard from her all day, so there I was, left with my thoughts running wild. Finally, around 2 in the afternoon, I received a phone call from her. When I saw her name come across my phone screen I fumbled for it and nearly dropped it. I picked up and wasn't able to get a word in before Amy began.

"I've had some time to think about this morning John and I must say, I think you handled yourself rather well. I enjoyed myself quite a lot. Did you?" she asked.

"Yes, of course," I rambled quickly. "It was so good."

"Well, I'm glad you enjoyed yourself. If you keep doing as you're told we'll get to do a whole lot more." She paused for a moment and sighed happily. "I'm going to be getting out of work shortly, then I have a little shopping to do. I expect you to be ready and willing when I get home, is that clear?"

"I'll be here," I replied. I wasn't really sure what she meant by ready and willing, but this didn't seem like the time for me to question her.

"You do remember the promise you made me, right, all the things you said you would do?" she asked me.

"Of course I do, I'll do whatever you want," I said so eagerly that I was a bit ashamed of myself. I couldn't help it though, what had happened earlier was the best experience I'd ever had. Even just talking to Amy right now was giving me an erection in her panties.

"Good girl... That's the right answer, you will do whatever I want and if you don't, you'll be punished," She said and then hung up.

I sat there and felt my heart racing as I put down my phone. Why did I keep promising her whatever she wanted, why was I being so obedient? I just couldn't say no to her. My mind swam with all sorts of different thoughts as I lost track of time. Had she actually just called me a good girl? Amy was just trying to mess with me, right? Regardless of how confused I might be I knew one thing, I was incredibly turned on right now. I had to fight my urge to masturbate. I wanted nothing more than to stroke my cock and cum right then and there, but I knew Amy had said she wanted control over my cock, so I resisted the urge. Despite this, I knew I had made a small mark of leaking precum on Amy's panties.

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The next few hours blurred by as I worked frantically trying to focus and struggling badly. I couldn't wait for Amy to get home. My phone pinged a little before 6 with a message.

"I expect you to wait, only the thong on, when I'm home in 5 minutes," was all it read.

I did what the message said without another thought. I made sure I was ready for her, cleaned myself a little, and stripped down to only her thong and then I waited at the door. That's when I ran into an odd question, how was I supposed to wait? Did I just stand there, should I be sitting, or kneeling, what was I supposed to do? I decided just kneeling next to the door seemed like the correct move. So I kneeled and waited for the next few minutes. Even though it was only a few minutes, they seemed like an eternity. I was excited to the point of giddy waiting for Amy. I heard her car pull into the driveway and the engine stopped. Then I heard the click of her heels getting closer to the door. My heart began to race as I saw the doorknob turn. Amy opened the door and stepped in, locking eyes with me.

"Good, you're exactly where you're supposed to be," She said with a smile on her lips. Amy's arms were full of bags from various stores. She hadn't just done a little bit of shopping. "Follow me," she said as she closed the door and kept walking.

I stood up and did as I was told, following her up the stairs and towards the bedrooms. I don't know what I was expecting, but so far this wasn't it. Her tone so far was upbeat, but very serious. She opened the door and walked into my bedroom, placing the bags on my bed.

"I took care of getting you some things that you're going to need from now on. After all, things around here are about to change for the better.," She said as she turned back to me. "We'll have to try everything on and make sure it fits first though."

She took a bag and emptied it on my bed. I blushed immediately after seeing what was in it. There must have been at least a dozen different sets of panties, different colors, and styles all now in a heap on my bedspread.

"Since you're going to be wearing panties almost exclusively now we needed to take care of getting you some. I can't have you wearing mine all the time. Besides, we have to find out what colors and styles suit you the best. As much as you have a nice ass, it's a different shape than mine and your complexion is very different," Amy said, smiling at me and holding up one of the pairs of panties.

She was right of course. She was gorgeous and well-tanned and well, I have the complexion you'd expect from someone who works on a computer all day long.

"You can keep that blue thong though, it'll be the first full set you own, make sure to take the rest when it finishes in the wash. For now, though, take it off, you have to try these on."

I did as I was told, slipping off the silky blue thong and placing it on the bed. I hadn't even processed what she'd said about the full set until I noticed that most of the panties in the pile did have a matching bra to go with them. For some reason this made me hesitate, something about the bra seemed like an infinitely bigger step than the panties.

Almost as if she were reading my mind, Amy responded, "You're not getting cold feet on me, are you? I'd hate to think that we can't make this work. It's just that everything looks better with a full set. You can't tell me that the lace and silk didn't feel good on your cock today. Just imagine how that'll feel caressing your nipples?"

She reached out a hand to me and ran her finger around my nipple. I shuddered from the feeling of her touch. I was caught off guard by how good that felt. This was more than enough to get me out of my head and put me back into the obedient mindset as I imagined that sort of feeling.

"Try this one first," Amy said, handing me a black lingerie set.

I slipped the panties on first. They were very lacy to the point where you could see my skin through them everywhere, the dark black making quite a contrast. Then, slightly hesitantly, I took the bra and started to figure out how to put it on. After a few seconds of watching me struggle, Amy stood up.

"I'll help you this time," She said, stepping behind me. Her hand gently took the clasp from me and fixed it, making sure the straps were on my shoulders and adjusted correctly. "But you're going to have to learn how to do this on your own soon. I won't always be here to play dress up with you," She said, whispering it right into my ear.

A chill went up my spine as her lips touched my neck, leaving a small lipstick mark. Amy stepped back around me, appraising me with her gaze. She smiled wickedly and then licked her lips.

"Well don't you just look tasty," she said.

Amy then unbuttoned her blouse, tossing it on the bed before shimmying out of the skirt she was wearing. She sat down on the bed, spreading her legs wide. I stared at her, transfixed just like I'd been earlier in the day. This time she had on a lacy black lingerie set that wasn't too far off from what I was wearing, the main difference being the garter belt and stocking that she had on.

"We're basically matching, isn't that cute?" She teased me. "I think you should bend over and crawl toward me. After all, I do need to get a better view of how those panties look while you're on your knees."

I dropped to my knees and crawled over, staring up at this amazing woman who was playing me perfectly. I stopped just short of her, not wanting to assume what to do next.

"You may kiss me, but only on the parts of me that are covered. I want you to start at the very bottom and work your way up," she said, placing one of her legs directly in front of me.

I bent forward and gave a small kiss to her stocking-covered foot. I slowly worked my way up, just guiding myself an inch or two before the next kiss.

About halfway up her calf, Amy spoke, "God that does look so good on you, your ass just looks so fucking hot in those panties." She reached forward and gave me a spank.

I couldn't help but let out a whimper, maybe even a moan, before I continued kissing her. When I was most of the way up her legs, Amy put her hand on the back of my head and guided me to her crotch, pushing me in. I kissed the panties covering her, taking in the small and the heat coming from her. I wanted nothing more than to pull her panties aside and to lick, but I didn't want to disobey her. After a second kiss, she pulled my head up and put it in between her breasts, pressing them tightly to me.

"You are being so good right now, holding back and doing only what I let you. I think you've earned yourself a small reward," she said. She moved her arms back and undid the clasp on her bra, taking it off. She pulled me back in, burying my head in her tits. "You can suck on them," She said playfully.

I moved quickly, putting my mouth on her breast, and began sucking on her nipple. She had such magnificent tits, well more than a handful, that there was plenty there for me. Amy began to moan as I sucked, reiterating to me that I was doing exactly what she wanted. After a minute she pulled my head back, the slight tug of my head exciting me a little.

She panted and said, "Come on now, can't play favorites," as she guided me toward her other breast.

I eagerly sucked and did the same, enjoying myself endlessly as Amy moaned and shuddered. Finally, she pulled me back and she fell back onto the bed. I sat there on my knees, catching my breath. With how much I was enjoying myself, I was starting to think this whole day had just been one long, very detailed dream.

After a minute of panting, Amy sat up and looked at me. "Well, I suppose I should show you the rest of the things I got you." She let out a soft moan, "As much as I would like you to model each piece of lingerie, I think I'll get those viewings as the days go on, for now, let's move on to the other clothes.

I admit, I'd lost my head there for a bit and had forgotten about the other bags. By the time Amy finished dumping out the lingerie sets and panties I figured that was everything she'd bought me. She slid another bag toward the edge of the bed.

"Go ahead, you can take a look at this one, you'll be needing it tomorrow morning," Amy said with a grin.

I looked at the bag, it was one of those lifestyle brands that all the fit gym girls wore. Whatever worries I had came to light when I pulled out what was in the bag. There were three outfits, each one matching yoga pants and a tight sports bra. They were all the trendiest and frankly, most showy and maybe even slutty versions I'd seen of such things. This wasn't just plain gym clothes, this was the kind that begged people to look at a gym bunny's ass as they worked out. One was a bright almost neon pink, the next an electric blue, and the last one a bright purple.

Amy grinned, holding up the pink set, "I did tell you that you were going to do yoga with me, didn't I? I couldn't have you doing that dressed wrong. After all, your program is going to be designed to get you nice and stretchy so I can bend you all sorts of different ways while I fuck you. It just seems right to have you dressed in pink then, doesn't it? All the other girls wear pink when they're trying to work on their asses."

There it was again, she'd said it so clearly, calling me a girl again. I was deliriously horny, but even I noticed. Honestly, though, I didn't care. Amy could dress me up however she wanted, if everything was this good, it didn't matter.

"Try it on," Amy insisted. "I'd rather find out now if I got the wrong size, though so far I seem to have a pretty good idea of what fits you."

Amy helped me and undid the lacy black bra I had on and placed it back on the bed. I slid the yoga pants on, the material tight and stretchy across my skin, and then I slid on the sports bra. It was so tight I could feel it rubbing my nipples each second I had it on. The whole outfit was that kind of tight on me. If I hadn't already been hard, this would have done the trick in a matter of seconds.

Once I had everything on Amy reached for me, flicking one of my nipples through the sports bra. "My my, someone is very excited by all this. I'm so glad though. If you love it, it'll motivate you when we're doing our morning yoga and workout."

I caught the "and workout" part and decided to let that go. I was far too horny and enjoying myself too much to have other concerns right now. Then Amy's hand wandered down to my crotch and began rubbing the fabric against my cock. I was straining against the fabric quickly, forcing it to stretch more as my cock grew. Then just as quickly as she'd started, Amy stopped. I moaned out, my body yearning for more contact and for a release.

"Not yet," Amy teased, "There are two more bags to go." She slid the next bag close to me. "This one's for nighttime."

I looked down and saw a dainty little nightie, it was frilly and was pink like many of the other things Amy had gotten me.

"When it's bedtime, you'll wear this to help remind you that you're mine." She looked at me, grinning, it was clear that she was enjoying herself, that she was getting what she wanted. "This last bag is the most important one," she said, sliding the last bag toward me. She reached in and pulled out a small box. "You already agreed to this, so no backing out on me now," she said as she showed it to me.

There in her hand was a chastity cage. It was small and it was a bright pink to go with everything else. It had a little lock on it and two keys. Amy took the keys quickly and undid the lock. She looked down at my cock and tilted her head out the side.

"Well that is a problem though," she said. "Right now you're just too hard for me to fit this cage on you. How are we going to fix that?" she asked playfully, knowing how I would respond.

"If I just cum we can fit that on me," I said, already beginning to beg her. I must have been quite a sight at that moment, kneeling in front of this divine-looking woman while I was dressed in bright pink yoga clothes, my panty line clearly visible, my cock straining against the fabric, a leaky spot already forming.

"Stand up," Amy said. I did so quickly. She reached out for me and cupped my balls, slowly applying pressure. "Until you've proven that you are going to follow everything you've agreed to, you don't get to cum again. I think a day or two proving you're a good girl seems like a fair exchange."

Amy held my balls tighter, making me tense up. It wasn't to the point of being painful, but it was an overstimulating sensation I wasn't used to. Then she released me and I fell back to my knees quickly.

"I think you need to go have a nice cold shower when you come out, we'll take care of caging you," she said as she stood up. "I'll be waiting," she said before leaving the room.

I sat there for a minute, catching up to everything that had just gone on. My heart was racing, my head was swimming and I was so turned on. Despite all this, I did what I was told. I went and showered, cleaning myself and letting my cock return to normal. When I came out Amy was waiting for me in her pajamas, or what passed for pajamas for her. It was a dark black teddy that left little to the imagination. She motioned for me to sit on the bed and then put the cage on me, clicking the lock on with satisfaction. She stood back up and I saw something that made me instantly start to strain against the cage. Around her neck was a simple chain, which now held the key to my cage.

"I know, I know, it's a cliche, but what can I say, some things just work. Besides, you seem like you're already having a hard time not staring at it," she said. Amy then squeezed her tits together so that the key was resting in her cleavage. "I think you'll enjoy knowing that your salvation is sitting right here, always touching me like you wish you could."

She wasn't wrong. I was imagining my cock being where the key was. This caused me to try and get hard in the cage, the feeling of rightness overwhelming me and I groaned.

"Oh, is someone trying to get hard," Amy said, teasing me. She grabbed me by the cage and leaned in, planting a kiss on the very tip. "Well too bad, you only get hard when I allow you to now." She stepped toward the door. "Now put on your nightie and get to bed girly, we have so much fun ahead of us."

Amy shut the door and left me standing there, confused, aroused, and most importantly caged. I put on the nightie, the lacy cloth teasing my skin and only making the cage issues worse. I had an incredibly restless night of sleep, spending much of it in a state of absolute lust-filled yearning.