📚 roommate to sissy Part 1 of 3
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Roommate To Sissy Ch 01

Roommate To Sissy Ch 01

by shesontop42
19 min read
4.54 (50300 views)
adultfiction

Disclaimer and author's note: This is completely fictional. I hope you enjoy it, please give me any feedback or comments you have.

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It all started with a roommate wanted ad online. I saw the location and price and assumed it was too good to be true. My current apartment was getting new ownership, and they would jack up the prices unreasonably, so I needed a new place. It put me in the unfortunate situation of going from a solo apartment to needing a roommate. So when I saw the ad online I jumped at it. The price was way less than what I was paying now and it was to split a small house with someone. There was even a two-car garage, so I could park my car in bad weather. I was determined that this would be the one. At the same time though, I assumed it had to be a scam, nobody would ask so little for what seemed like a sweet housing setup.

I sent an email to the address on the ad and heard back quickly. They replied within the hour, asking a few questions. The usual things were, what was my job, why was I looking at a new housing arrangement, how long had I been in my current one and what had I been paying. So I explained everything, hoping to get a bit of sympathy. I worked for an internet security company and mostly worked from home. Due to this, I would be around a lot, but that meant I could help with chores consistently. I explained the situation with my current apartment and that it bummed me out to have to leave it after the past three years. Again, within the hour I got a reply setting up a time to come take a look at the new place so that my potential roommate could meet me and see if the fit was good. One of the many reasons I was excited was because the ad said I'd have a bedroom and an office to myself, which would give me a little more space for my computer and work setup.

My appointment was set for a little after my usual work hours, but just in case I hit any traffic, I worked through lunch. I got in my car and drove across town to the address I'd been given. As I drove I started to feel like maybe the ad forgot a zero in the rent. The houses here were all so nice and so big. This was the nice suburban part of town where all the well-to-do families had their houses. There were plenty of well-maintained lawns and fancy cars in the driveways. I pulled into the driveway and honestly couldn't believe this was the place in question. The house was bigger than the one I grew up in and it couldn't be more than ten years old. It had a really modern, clean look to it. It was dark green with a black roof and a nice overhanging porch to the side that had bright red cedar making a contrasting color. The garage was attached and seemed way bigger than just a two-car garage as the ad had said. Needless to say, I already felt really out of place with my old Subaru and my comfy clothes. My concern that this was a scam only grew.

I sent a message to the number I'd been given and then got out of the car. By the time I reached the front door, a woman was waiting for me. She looked to be about my age, probably mid-thirties, and was dressed professionally though I'd still say a little provocatively. She had on a tight black business skirt and a black blouse that was unbuttoned a few from the top, which only served to show off her very ample cleavage. I made sure not to stare, but I did notice the faintest little bit of black lace peeking out. She was very fit and seemed very well put together, her makeup was just so and her dark brown hair was very taken care of to the point where it seemed like the large curls only swayed when she would have wanted them to.

"So, Hi," I began, "I'm John Timms, am I in the right place? I'm here about the roommate ad."

"Absolutely John," she put out her hand to shake mine, "I'm Amy Martin, nice to meet you." She had a firm handshake, but her hands were so soft. Her nails were also impeccably well-manicured, bright red at the moment. "Come on in and I'll show you around," she said as she walked in.

I admit, with her back turned I couldn't help but stare at her ass. The skirt framed it so well. You could tell she worked out just from how toned it looked. I quickly adjusted my pants a little as I realized I was getting hard. Trying to not get labeled as a creep and lose the spot, I moved my gaze and started to look around. It looked like a house from a modern home magazine. Lots of neutral colors offset with dark grays and blacks. The place was incredibly clean, the furniture was nice and the TV was huge. Amy brought me to the kitchen first.

"So, here's the deal," she said, looking me straight in the eye. She leaned forward on the counter, exposing her cleavage more. I tried not to focus on it, but I was thankful that the counter between us was above crotch height. "I know the rent I'm asking for is low, but honestly it's because I don't need the money. I just put the rent in the ad because I need to know you can take care of yourself financially. I'm looking for a roommate because I just prefer having somebody else here. I go a little crazy when there's nobody else in the house. My last roommate moved for a job about a month ago and the quiet is just too much. It's also nice to have somebody help out with the chores. I pay somebody to take care of the lawn, but I'm not the type to hire a cleaning service. I've always felt like the people who make the damn mess should clean it up, not that I really make that much of a mess."

"Yeah that makes sense to me," I said, trying to agree and get in her good graces. "It's a lot of house for just one person."

"You're not wrong. Honestly even with my hobbies I couldn't manage to fill up all the rooms. I do have one very important question for you though. In your replies earlier, you said you were fine helping out with the house chores, does that include cooking?" she asked with a serious look on her face.

"Yeah, no problem at all, I actually love to cook," I said. I wasn't lying, by virtue of working remotely I had the chance to cook pretty much every meal I ate, I never had to do leftovers or microwave food unless I wanted it.

'That is fucking fantastic," Amy said enthusiastically. "I can do a lot of things, but I am just a shit cook. Hell, you cook regularly I'll knock some off of your rent." She paused for a second, "Speaking of that, as much as the money isn't the big factor, You'd have to sign a contract and all that, are you still interested?" Amy asked as she opened a drawer and pulled out some paperwork. "I know you said you wanted to move in ASAP to avoid the rent spike, not like it's an issue for me, the two rooms are completely empty." She paused for a second and then put her hand on her forehead, "Duh, you probably want to actually see the rooms," she said with a chuckle. "Sorry, it's been a busy day at work, I'm a little frazzled and need a nice long bath."

Amy stood up and stretched, raising her arms and pushing her chest out. Again, forcing my view to her breasts, which at this rate I knew I'd be imagining in my dreams tonight, not to mention I was now picturing her naked in a bath. Admittedly I was now a little worried that I wouldn't be able to handle having an attractive roommate. Heck, I was surprised she was ok with a guy for a roommate. Either way, this whole situation seemed too good to be true. I followed her up the stairs quickly.

"This would be your room," Amy said, opening the door to a bedroom that seemed like it was the size of the apartment I was currently living in. There was a queen-sized bed in the middle of the room with large bedposts, it was significantly nicer than my own bed. "Bed's all yours if you want it, or if you prefer I can have it put in storage and you can bring your own."

"Are you kidding me, that's a hell of a lot nicer than mine, I'll gladly take you up on that," I replied.

Amy walked over to a door on the side of the room and opened it, showing me a walk-in closet. I stepped in, the closet was big, but there was one thing that caught my attention. Pushed back on a rack was a bright pink dress, the kind a girl in their twenties wore to go clubbing.

"Oh shit," Amy said upon seeing the dress. "Chrissy must have forgotten this when she moved. It'll be gone before you move in." She turned around and smirked at me, "Unless you want it?"

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I don't know why but I blushed slightly before laughing it off, "You know I really don't think that's my color, besides, I have a feeling I'm a bit too big for it." Don't get me wrong, I'm a pretty average guy, but I also wasn't going to see if it actually would fit me. I appreciated the fact that Amy was so calm and willing to joke already. I was a pretty sarcastic person, so it was going to make my life a lot easier if she had a sense of humor.

Amy chuckled, "I guess that's one of the only downsides of a guy housemate, not really going to be able to share clothes with you." She walked to the back of the closet and opened the door on the other side. "So here's the office that'll be yours. It connects through her but also has a normal door to the hallway. There's also a bathroom that'll be yours on the other side of this."

I walked in behind her to look at the office, again it was larger than I had any right to expect for the cost I'd be paying. I could easily set up my computer and all of my work here. "This is fantastic," I said happily.

"So you said you work from home a lot, right?" Amy asked.

"Yeah, almost exclusively. No point in paying for an office when my work is contracted out to companies all over the place." I replied.

"Makes sense, well I deal with business all over the place, so fair warning, I'll be in and out regularly and at all hours depending on what country I'm meeting with," she said.

I didn't ask further, but I figured somewhere down the line I would figure out more about what her job was. I didn't want to pry too much upon just meeting her. We walked back down to the kitchen where she'd left the contract.

"So, are you in?" Amy asked with a smile.

I couldn't possibly think of a reason not to say yes, so I said, "Of course." I signed the papers happily. "When can I move in?"

"As soon as you want, just give me a heads up so I can make sure I'm here to help out." She pulled a key from her pocket that was bright pink. "Sorry, I'll get a new key made soon, it's the one that Chrissy had, she was a bit of a girly girl." She handed me the key and I put it on my key ring. "I think this is gonna work out great," she said and then she grabbed me and caught me off guard, giving me a tight hug. I could feel her breasts pressed against me, the soft, silky material of the clothes on my skin, and her breath. I got hard instantly and only hoped that she didn't notice.

After a moment she let go and let me be on my way with a "Bye roomie," and a smirk. I figured the fact that I was still moving in meant that she hadn't noticed my erection, time would prove me wrong.

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A few days later I moved in and started to settle into a routine. Much like Amy had warned me, she was in handout all the time at the most random hours. Over the course of the first few weeks, Amy and I sorted out a lot of things. We came up with a cooking schedule, I cooked on certain days, and she "cooked" on others, meaning she would order whatever we wanted. We had a laundry routine figured out and helped each other out on that regularly. Honestly, I took care of a lot of chores, but I was at the house all the time, it didn't bother me.

The only thing that threw me off was how comfortable Amy seemed to be about herself. She walked around in somewhat revealing pajamas without a care of me staring at her. I appreciated how relaxed she was, but I'm only human. Half the time after I saw her I'd end up going to my office to masturbate thinking about her. I tried not to, but I just couldn't help myself. She was an absolutely gorgeous woman and It had been a while since my last girlfriend. Besides, my jerking off was better than me fucking up my housing situation by trying to sleep with her. I took care of my needs and she was none the wiser, at least that's what I thought. Amy was playful, smart, witty, and clearly good at her job, somehow I'd ended up living with her and I knew enough to stay in my lane.

The only times I really struggled was when she would get a little tired and flirty. She'd tease me a little bit and I admit I'd get flustered. Once we were watching TV on the couch and she fell asleep and ended up falling over onto my lap. Her head was only inches away from my cock. To prevent myself from doing something dumb I gently woke her up and she went to bed in her room. Every once in a while I'd walk past her door and it'd be wide open and I'd get little glimpses of her. She did yoga most mornings in the living room and I made it my mission to avoid being around that. It was just more than I could handle. She wore tight outfits that left nothing to the imagination and watching her sweaty, fit body just seemed like I was asking for trouble.

The closest I'd come to getting into trouble was one particular night when Amy had gone out for a "Business meal" as she'd put it. As she explained it she'd take a client out, flirt with them, get them drunk enough to agree to what she needed, and then send them on their way all hot and bothered. Despite her explaining this, I still had no idea what her business was. Well, this time her client clearly had a high tolerance cause she came back pretty drunk. I'd heard her come in.

"John, I need some help," she yelled as she started up the stairs. I was in my office, just playing a game.

I popped my head out and replied, "What's up Amy?"

"I'm too fucking drunk, I had to get a ride home, can you drop me off at my office tomorrow?" she said, slurring just a teensy bit.

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"Yeah, of course, no problem," I replied quickly. I admit I was curious to find out where she worked.

"Thanks, John, you're the fucking best," she replied as she staggered into her room, leaving the door wide open behind her. "God this guy could fucking drink, I don't think I've drank that much since my sorority days." She kept talking to me, So I moved toward the door.

"You sure you're not gonna be too hungover for work tomorrow?" I asked as I approached.

"I'll be fine, I'm not some lightweight who can't hold my liquor," she replied as she threw off her shoes. I saw her hand reach up to the back of her dress and begin to tug at the zipper. Her dress was tight and blue, just professional enough, but still forcing your gaze onto her. "Fuck me," she said. "Can you help me with the goddamn zipper, it's stuck."

My pulse jumped a little, but I walked in to help. "Yeah, sure," I mumbled out, trying not to be too excited. At first, I thought it was because she was drunk, but I was wrong. The zipper was absolutely jammed. I pulled and yanked at it for a few seconds, struggling.

Finally with one big pull the zipper gave way. The problem was I yanked so hard the whole dress just fell off of Amy. My breath caught as I saw her. As much as I'd imagined it, my imagination did not do her justice. She was absolutely stunning. She had one blue lingerie that matched her dress, the lace barely covering anything. The thong drew my eyes right to her ass, an image that is permanently seared into my mind. Then she turned around and I got the rest of the view. Her perky nipples pressed up against the fabric that strained to contain her large breasts. Her perfect large curls fell just over her shoulder against her skin. I was basically drooling, I couldn't get a normal thought through my head. Amy's voice snapped me out of it.

"'Well, I did ask you to help me with the dress," Amy said playfully. "You might have gone a little overboard though." She smiled, "Thanks for the help I suppose, now if you don't mind, I have a nice hot bath calling my name."

She turned around and walked to her bathroom door, opening it and going in without a second look at me. I stood there awestruck for a few moments, my cock throbbing in my pants. I immediately went back to my office and masturbated, finishing hard.

That night I went to sleep, still worked up. I couldn't help but picture Amy, the dress, the lingerie, her body, they all swam through my mind. I woke up expecting to take her to work but instead found a message on my phone.

"Thanks for the help last night John, I had to go in way earlier than expected so I got a ride from another one of the girls at work. It'd be a huge help if you could run some laundry for me" it read.

Honestly, that was ok with me, I was a little worried that things would be awkward for me after last night. Amy would be fine, hopefully, she wouldn't even have noticed how hard I got given how drunk she was. After a few groggy minutes still thinking about her body, I started on my morning routine. I took a shower, ate some breakfast, and did a little cleaning. I went to the laundry room to run the laundry Amy asked me to. I saw her laundry basket sitting there and opened up the washer. That's when I noticed, sitting right at the top of the pile of laundry, the lingerie Amy had been wearing the night before.

I stared for a moment. The blue thong that I'd seen the night before made me picture seeing it on Amy again. My pulse began to race and I could feel myself getting hard. I thought about it for a second. I was home alone, Amy was at work, and I'd been trying too hard not to make a mistake, but I was still a little sleepy and the impulsive part of my brain took over. I grabbed the panties and looked at them. They really were exquisite. This was not some cheap pair, this was designer stuff based on the material and quality. I couldn't help myself and pressed them up to my nose and took a sniff. They smelled slightly perfumed, still carrying some of the scent Amy regularly used, but they also had the scent of her body, of her pussy. It was like a drug. I was completely hard now and took a second sniff, letting Amy's scent completely fill my nostrils.

I was completely lost in the smell when I heard a sound behind me, turned around and saw Amy standing there, a big grin on her face.

"Caught you, you little panty pervert," she said.

I didn't know what to say. My mind was swimming, my heart was pounding and my cock was throbbing. "Amy, I, um...." I stammered, "I'm just starting the laundry like you asked."

"Last time I checked, running laundry didn't involve sniffing panties, did it?" She said, still smiling. She stepped toward me, "I came back because my meeting got canceled and I'm still a little tired, but I guess now we need to have a little talk."

This was it, I knew I was about to be thrown out of my housing situation and get labeled as a creep. I was going to have to move towns just to try and get away from this.

"If you want my panties you're supposed to have the manners to ask for them," Amy said. She snatched the panties from my hand and then pressed them against my face forcefully. "You've been naughty, that means you need some discipline. Things are going to change around the house and you're going to have some new rules to follow."

I couldn't believe what I'd just heard from her. Either way, I was far too turned on to be able to think straight or to realize the trouble I'd just gotten myself into.

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