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

“Sorry that was weird. It’s just I kind of want it to be more intimate than chilling on the couch and you whip it out.”

I laughed and so did she. Whatever mood there was before turned light and playful. “Fair enough.”

She started to play with the ends of her hair, “Umm jay?”
“Yeah”

“One more thing”

My mind started to race. What more would she ask? “What’s up?”

“Can… Can I… You know… Touch… It”

“You want to play with it?”

“No, just touch it. I want to know what another person feels like.”

Almost instinctively I stood up. I pulled down the waistband on my shorts and out sprung my dick. It was fairly average. Maybe 6 1/2 inches depending on the day. It stuck straight out infront of me. She looked surprised that I did it so quickly. She readjusted herself looking a tad uncomfortable. Chloe’s hand slowly reached out, trembling slightly. Wait. Did she say another perso- Chloe’s hand touched the underside of my dick and it jumped. My mind went blank. Her hands were soft. I looked down and saw her pale hand slowly exploring my cock. She was lightly dragging her hands across every inch. Her eyes were locked on to my penis. I saw her biting her bottom lip while her hand tucked in between her legs seemed to slightly move. Her hand slowly wrapped around my dick. I let out a moan and that brought her back to earth.

She retracted her hand and started fanning her face. “Woah that was sexy”

I felt disappointed nothing more happened. I tried to put my dick away but all it did was make a tent so I sat down.

“Jay… This may sound weird but… You…you have such a nice dick. It’s pretty close to what I would make when I would draw penises.”

“Haha thanks, your hands are soft” what the fuck was that line.

She looked at her hand that touched me and stared at it. “Thanks no one has told me that before.”

Haha good line Jay. I nodded. As if right on cue, my stomach growled. I thought about food and realized I haven’t eaten anything other than take out in this dorm since her pizza. “Do you want to go to that store with me?”

Her eyes lit up, “yes that sounds fun” now it could just be me, but I feel like I broke some sort of wall down. The shy soft spoken girl I knew a week ago seemed to feel way more comfortable in being herself. I liked Chloe before but I really like this Chloe too.

I got up and went to grab some shoes. While my back was turned it saw her go into her room to change. When she came out she was still wearing the same top, her hair was up on a messy bun, she was wearing sneakers and she had some black shorts on. The contrast between her skin and her shorts was so sexy as was her hair all done up. I felt a boner come in again as she walked towards me. It didn’t help that her nipples were hard and poking through her shirt, she definitely didn’t have a bra and frankly didn’t seem to need one to make her breasts perky.
We drove to the store and the car ride was mostly silent other than the music playing. It was weird though because it wasn’t a bad silence, just a comfortable one. We parked and she got out of the car first. She turned around and leaned back into the car, “Come on hurry up, i’m hungry” her tits hung and apparently so did my jaw because she looked down at her chest then back at me and smiled. She giggled and closed the car door

This girl was freaken adorable. Not only was she sexy as hell but she had a childish joy to her as we walked around the store picking out food for a few weeks. Standing in line at the self checkout, she dropped her card. And when she bent down to pick it up her cute tight ass was right there in front of me. To this day I don’t know why I did it but I placed my hand on her ass and did a fast squeeze. She let out a tiny yelp and shot right up. Some of the other customers looked at us wondering what the sound was. She looked at me and her eyes shot daggers but her face was bright red with a tiny smile.
We buy our stuff splitting the bill and head back to the car. I wasn’t sure if I should have felt bad about what I did but I got my answer when she was putting the bags in my trunk and spent way too long bent down. It may have been my imagination but her shorts seemed to be hiked up a little more exposing more of that glorious pale ass. We get in the car and make our way home.

The sun sets as we get home. After putting everything away and making dinner I asked when she wanted to do it. She responds telling me she needs to get ready. I sat in my room waiting impatiently. Minutes went by and it felt like an hour. She called for me. And when I turn the corner I see something I’d never seen while living with Chloe. She was wearing a sexy night gown that was all black. It shaped to her body and hips then loosened up down to the knee. The little light coming from her room added a sort of soft lining to her body. She had small hips and a slender body but at 5’2″ it made sense. The dress formed to her boobs showing the curve and still letting them jiggle with each little movement. She saw me staring at her, “Do… Do you like it? Is it too much?”

I stood there with my mouth open and all I could do was shake my head no.

“It’s probably too much”

“NO” I blurted out startling her. “Sorry, its great”

“I don’t wear stuff like this alot but I had this and figured since you were so accommodating, I figured this was the least I could do.”

I just nodded again

“Weeelllllll….”

“Oh… Yeah sorry I was… Distracted”

She giggled. “Come on.” I followed her into her room, she had cleaned up and there were some candles lit. The TV she had was moved to the foot of her bed. She stood in the middle of her room looking amazing. “So….”

“How do we go about this?”

“I don’t… Sorry I just got really nervous”

“It’s okay” I went over and hugged her for some reason but it seemed to work as I could feel her relax in my arms.

She lightly pushed away, “Sorry, thanks.” She wiggled her hips a little as if she was a tad uncomfortable in what she was wearing. “Okay… Haha… Umm lay down”

I went to lay down when she told me to stop and to strip. I do so and now I am naked in front of her. Chloe’s eyes are locked on my dick again and her gaze is hardening the rest of my dick as I’ve had a semi since I saw her outfit. Now fully erect, she motions for me to play down. I lay on her bed with two pillows under my head. I looked down and she was farther down the bed still looking at my dick.

“So umm, do I just start”

Chloe was breathing harder now as she cleared her throat, “Oh yeah umm what kind of porn do you want to watch?”

“I.. Uhh.. I don’t know I could probably just look at you” you could see the redness even in the dim room. She had a tiny smile, “How about you decide.”

Chloe thought for a minute then turned on the TV and connected it to her phone. She quickly navigated to a video called ‘Vicats Compilation’. She put her phone down as the video started. I started Masturbating as the video played and quickly realized what kind of porn we were watching. Chloe’s eyes were glued to my dick watching me intently like she was taking notes or trying to memorize what to do. The feeling of being closely examined while at my most vulnerable is a sensation unlike any other. I felt my climax building very very quickly and tried to slow down but my body wanted me to speed up. I wanted to cum for Chloe, I wanted her to see me bust all over her bed or her face, I needed her to see me climax. It was no longer something that was about to happen, it became a desire. I needed her to see me cum. She was fiddling with something under her bed as she watched. Her face grew closer and closer as I could feel her heavy breaths against my precum creating a cooling sensation that was driving me even crazier. I turned to the side and my dick was now staring right at her i picked up speed and she started to whisper, “Mmm, please” he breathing became harder, “please please please” I could feel it building up when she moaned, “mmm Jay for me”

I can’t remember the least time my body twitches while cumming. I shot my semen on her face and glasses and then the rest was on her bed. She stopped whatever she was doing. And sat back on her heels looking at me and breathing heavily.
“Wow”

I wanted to say something but I could barely catch my breath.

“Do you…nevermind”

Between my breaths I could manage a quick, “what”

“Do you always cum like that”

I waited for my breathing to slow before answering, “Its usually pretty powerful… But there was a lot…more that time” it was still hard to speak for very long.

She just said okay and kept looking at me
“Was that okay?”

“Yeah” she nodded.

“So what now?”

She looked to be in thought again and looked around her room. She reached down. Under her bed and got the dildo she kicked there last week, “Can I?”

“Right there?”

“No I… Can i… You know, sit next to you?”

“You want to masturbate next to me?”

“Is that okay?”

“I’d love too watch you masterbate”

She was about to stand up but then said, “I know it might not be fair but can I do it under the covers.”

Without delay, “Yeah!”

“You’re okay with not seeing my… You know”

“Can I see your boobs?”

She looked down and squeezed them between her arms, “I’ve never shown anyone.”

I couldn’t help but smile. I was about to see what could be my favorite pair of boobs in all their glory. Chloe climbed in her bed under the covers with her stomach and torso exposed. We propped the pillows against her headboard and sat next to each other. She pulled down the dress and it was as if the world slowed down. My stomach actually hurt a little with the amount of butterflies in it.

When the top of her gown passed her nipples the room seemed to lighten up. The glow of the TV hit her ivory chest and accentuated the smoothness of her skin from the soft curves of her collarbone to the way the edges of her tits came down from her shoulder, under her nipples and back towards her sternum. I swallowed to help my dry throat. Her nipples were hard, small with pink almost ghostlike areolas that were no bigger than a quarter. Their shape blended in with her soft creamy 36B boobs. I reached out for one and she kind of turned away.

“Sorry,” she turned back, “no one has touched them,”

“I’ll be gentle” I continued to reach out and cupped her left breast. She let out a heavy sigh. I lightly squeezed it and she closed her eyes. She quickly re adjusted herself moving my hand away. She brought the dildo under the covers and shifted some more. Than she reached under her blanket and pulled out the panties she was wearing. They had an immediate smell to them that filled my nose. It was sort if musky but oh so intoxicating. She threw them on the floor, looked at me and Chloe mist have started to masturbate because she started to softly moan. I saw her hand move under the covers and watching that along with her boobs moving with every movement made me instantly hard. Chloe quickly took notice as her focus switched from the TV to my dick. She was biting her lower lip as her tiny moans became more audible and higher pitched. Her chest rose and fell quickly as her hand started to speed up under the sheets. I started to jack off next to her and she let out a sexy groan right when I started.

It took a little longer for me to build up but I didn’t care because I now had this beautiful girl next to me topless and enjoying herself as much as I was.

Suddenly she leaned her head on my arm and tried to snuggle up as she played with herself. My dick jumped in my hand and I slowed down some to prolong the enjoyment. She seemed to like the bigger longer strokes since she let out a -mmmm- when I did so. I looked down and saw her hand moving in an odd pattern. I’ve watched a lot of porn and know that the motion of her hand was off. It sorta looked like she was jacking off a dick. Must have been the way she was using the dildo. Some girls use it at different angles. But that didn’t stop me from pretending. My eyes locked onto her and I started to imagine her with a dick.

“God Jay you have such a nice cock”

“Thank you. And you Chloe have such nice boobs, they are perfect.”

She looked down and started playing with one. She pulled on her pink nipple and let out a cute moan. She kept lightly pulling on it while she continued to masturbate. I went back to picturing her with a dick and started to wonder what it would feel like to touch hers like she touched mine. I wanted her imaginary dick to jump to my touch. I wanted to see her cum all over the bed, herself, and even me. I started to speed up and announced that I was getting close.

I didnt get a response from Chloe so i looked and she seemed very focused and they she broke the silence by letting out a huge “Oh fuck!” Her breathing instantly became loud and deep as she moved from a seated position to a laying one. Watching this amazing girl cum definitely put me over the edge. I came too but I didn’t realize I was pointing at Chloe. One rope of cum came out and nearly reached her nipple but the rest were a lot weaker since I just came not 15 minutes ago. Still the look of this girl coming down from an orgasm with the slightest bit of my cum on her left boob was surely a sight to behold. The glow from the TV added a slight blueness to her pure skin as her chest rose and fell with each breast.
She comes to and looks up at me with a shimmer in her eye. I’ve never had a girl look at me like this but I swear I could have kissed her right then and there. Why I didn’t, I have no idea. She looked at me breathing a little heavy too and then she looked at my dick that was still hard but was starting to get soft.

She reached out and touched it. “I can’t get over his dick jay, I… Umm… Can i… Suck it?

This girl was insane. Hell yeah she can suck it. But her touching it was making it feel a tad raw. I thought about it and realized I probably wouldn’t enjoy it after having came twice. I looked at her and said, “That would be nice”

She licked her lips slowly and got up to readjust herself.

“But I’m really sensitive and don’t know if I’d be able to enjoy it to its full extent. She didn’t seem to mind that answer as if she knew exactly what I meant.

“Tomorrow?”

“Yeah”

“Thanks Jay”

“Yeah it will be fun”

“No not that”

“Huh”

“Thanks for everything” She paused and sat up straight, “thank you for how you’ve been, not judging my art or requests, being patient with my mishaps of living with a guy. I know I’m not the perfect roommate but you’ve made it really easy to live here. Granted I was gone for a few days but I’ve generally felt content living here and not stressed about hiding my interests and my art from you.”

“The pleasure has been all mine Chloe” I meant it, “Other than worrying about you while you were gone. I’ve liked you as a roommate….so far” I winked at her

She nicely elbowed my arm. “Hey!”

“I’m joking… But seriously, this year is going to be great.”

She looked down at her lap fiddling under the sheets and pulling out her toy which was dry, “yeah hopefully. Hopefully you can be even more accommodating”

Not realizing the state of the dildo, I looked her in the eyes. “Hey” I reached out my pinky and smiled, “you can be who you want to be with me, remember… No judging”

She smiled but had some doubt on her face, “If you say so,” she reached out and we pinky swore.
The bed we were in was really small and I’m a stretcher when I sleep so I excused myself, she seemed more than okay with that. I got up and grabbed my clothes while she remained under the covers. She smiled at me and waved good night. I walked to my room feeling light and happy.

As I got in bed I started to really think about what it was like living with her. We’ve only known each other about a week and we have already watched porn together but none of it felt forced or unnatural. My mind started to wonder what it would be like to be in a relationship with her and then it got really weird as far some reason I wondered about whether or not she had a dick. I don’t know why I thought that but you know how late night thoughts can be. Could I be with someone who had one? Did I want to be? Did that matter? I came to the conclusion of crossing that bridge when i got there. But then I realized what i was thinking. What are the odds that this perfect girl that I got along with had a penis? There’s no way she actually had a dick… Right?

Source: reddit.com/r/Erotica/comments/12hnors/chloe_the_roommate_4_tfm20s