CrispyWinter, Author at NSFW story

Chloe the Roommate 9 [TF/M][20s]

Chloe giggled with delight.

She laid there with a slight exhaustion to her breathing. I stood up and looked down at her. She laid there on our beds naked with a half hard dick and and a huge smile across her face.
I climbed back on the bed and crawled over her. Chloe’s arms were laid out and I took this time to explore her body again. I took one of my hands and started to trace shapes on her stomach. I ran my finger under her bob and outlined the shape of it. Her breathing picked up a little but she seemed to be more relaxed. I looked down and her penis was trying to get hard again. I looked back at her and smiled. Our eyes met and she smiled again.

“Jay you’re incredible”

“You too Chloe”

“I wasn’t expecting you to take this and run with it”

“Neither did I.” I continued to trace her collarbone and her shoulders.

“It nice”

“What is”

“Being yours.”

I had this feeling wash over me, “I like it” Read more »

Chloe the Roommate 8 [TF/M][20s][Oral][Foreplay]

My calm happiness shifted as I felt a soft warm breath of Chloe’s voice in my ear. “take off those clothes.”

Like a soldier in the morning after first call, I stood tall. I went to take my shirt off but was told by Chloe to go slower.

I tried my best to put on a show but I felt like I wasn’t doing much. Chloe however thought differently as she was rubbing the outside of her shorts. I could see the bulge.

There I was standing in front of a girl, my roommate, my girlfriend, naked and at about half mast. She looked me up and down and then stood up and pushed me back down. Read more »

Chloe the Roommate 7 [TF/M][20s]

“That would be awesome, yes I will be your boyfriend” Despite the weird aversion to touching her, everything in my body wanted something more with Chloe. I really did like her and I knew one day I would get over whatever wall was in front of me.

Chloe had a giddiness to her and hugged me really tightly, “Makes me so happy to hear you say that!” The position she was in was really weird so she moved up a little and hugged me normally. Now we were side by side and I could feel her chest against mine. Her heart beat was trying to match my own and our legs intertwined. Yes, our dicks were touching and as weird as it felt to have my penis against another it didn’t weird me out. It was kind of hot if i’m being honest, no different than my dick against a vagina. Like I would know but I don’t since Chloe is in fact the first girl I had been with since my high school crush. Read more »

Chloe the Roommate 6 [TF/M][20s]

Right as she said that I felt my asshole clench up. “I heard that right, right?”

Chloe nodded vigorously. “Yeah!”

The idea of that being a thing had honestly never entered my mind. For some reason, I wasn’t able to provide an answer at the moment. There wasn’t really any particular reason why I was hesitant. Maybe it was the idea of getting closer than just playing around.

“Umm… I don’t know. Can… I think about it?
She seemed a little let down but I guess it’s a little different from how accommodating I’ve been with everything else. Still though, I’ve never had my butt licked.

“It’s not a no, just it’s not an immediate yes.”
That seemed to put a little bit of hope back into her as she snuggled a little closer to me. Her boobs felt nice against my arm. Her finger starts to lightly trace my stomach sending tingles up my spine. I looked over at her and she was locked onto my lower torso. Her finger turns into two then to three. The area she is tracing becomes larger and it could feel the blood rushing from my body into a centralized point. Her hand on my body feels amazing and I started to feel my dick throb again.
She noticed and her hand made her way to my crotch. She lightly stroked it making soft noises of approval. Read more »

Chloe the Roommate 5 [TF/M][20s]

I woke up earlier than usual and had time for a nice breakfast before work. Last night was amazing and it almost felt like a dream. Part of me knew it was real but the other part had to make sure. I got up and put on some gym shorts and walked out of my room. What i saw surprised me but put a smile on my face
Chloe was making breakfast and humming to herself and then looked over my way and smiled, “Morning Jay!” She made her way over to me and hugged me real fast then planted a big one on my cheek.

“H..hey what’s up”

“Making us breakfast,” she made her way over to the stovetop, “I was going to bring it to you but since you’re up early we can eat it.”

“Oh nice, and the kiss?”

“I don’t know it just felt like somethi-…sorry I wont do it again”

“No no it was… Nice,” I couldn’t help but smile. I sat down on the couch and pulled the coffee table up close. We really should have a dining table if this is going to become a thing. “Hey Chloe, last night…” Read more »

Chloe the Roommate 4 [TF/M][20s]

My mind went blank. I wanted to be sure of what I just heard. I know I was pretty horny but there is no way she just suggested that she wanted to watch me masturbate. Sure it’s a lot of guys’ dream but given the opportunity, hesitation sets in.

“Did I hear you right?” I straightened up.

“I’m sorry… I… I shouldn’t have said that.”

“No its cool just making sure”

“I don’t know what came over me I just,” she let out a deep breath, “feel comfortable around you knowing you wont judge me.”

“That’s true… Umm just wasn’t expecting that”

“You don’t have to say yes I just-

“Okay”

“What?”

“Okay, you can watch me masturbate”

“Really?”

“Yeah”

“You sure you are okay with it.”

“It may be a little weird but it sounds fun”

“O…Okay then” she seemed to relax a little as a smile spread across her face. She brushed her hair behind her ear.

“Now?” I said starting to remove my pants.

“No not now, I want it to be special.”

A confused look came over me Read more »

Chloe the Roommate 3 [TF/M][20s]

“Shit shit shit” I whispered.

She stopped making noises. Crap. She probably thinks I could hear her. I lay there looking at the ceiling. My heart was pounding out of my chest and I didnt move a muscle. I heard no noise from her room for a little bit. I started to calm down when I heard a door open. I closed my eyes pretending to sleep. My heart was beating even faster now. Was she in my room? She must be seeing if I was asleep. Just try to breathe normal and Don’t. Move. A. Muscle.

Relief came when I heard her in the kitchen. I heard her tiny footsteps walk slowly past my door and then I heard a door close again. Maybe I was in the clear. I better just go to bed and not overthink anything.

I woke up around 8ish for some reason. I tried to go back to sleep but it was not happening. I thought about last night and worried about what she might say. I think the best idea is to just ignore it. I got up and peeked my head out of my room. Read more »

Chloe the Roommate 2 [TF/M][20s][Masturbation][Spying]

Thankfully since it was a busy day at work my little imagination mishap didn’t throw me off too much. However when I got in my car the image of her cute face, slender body with a nice looking dick on it took over my thoughts. My growing hard-on was getting increasingly uncomfortable. My first thought was to be honest but what would she think if this random guy that just moved in told her that he’s been picturing her small frame naked playing with a dick that doesn’t even go on her. So I scrapped that idea.

After racking my brain with what to do next I decided to just head back. The heavy traffic and music kept my mind from wandering too far. I parked the car and sat in there for a little while wondering what to do next. What have I got myself into? All I did was see a picture she drew and now I’m intentionally looking at similar porn and imagining her with different parts. This has never happened to me before. One time I saw my high school crush topless because she jumped in the pool the wrong way and when she came up so did her perky boobs with her reddish brown nipples pointing right at me. The next time I saw her, It was hard to picture her without a top. But this girl, Chloe, drew one picture of a fake person and suddenly it’s all I can think about. Hell it even has me kinda hoping that maybe one day I might be able to catch her in the nude and a part of me wants there to be a dick standing straight up looking at me. Read more »

Chloe the Roommate 1 [TF/M][20s]

I’m not sure what happened to my other account (Akix) but I’m not able to post on it. If you need proof that I didn’t steal this story then you can message me on my original account but I’m not able to post. I will be reposting the stories on multiple subreddits with his new account and it will end with the finale that has been completed Anyways without further ado… Chloe the Roommate

After coming back to school for my sophomore year at college I elected to stay in the dorms again. The dorms were split up by major so it was nice being around like minded people. While I made a lot of friends last year, they were more just classmates I came to realize as none of them “had the time” to chill over summer break. I decided to just focus on my Art major and hopefully get a new job as something close to that. Instead of befriending my new dormmate, I just decided to do the whole head nod thing when ever I see him. What I didnt plan on was that Him was a Her. Read more »