My Roommate Made Me a Sissy

"He-ey," Ashley said as she opened the door.

"Hey," I said back without nearly the amount of enthusiasm I wanted to show.

"So, what are we doing? Where are we going?"

Up to your room to fuck, I thought to myself. It was the only thing I wanted to do at that moment and while Ashley seemed into me I didn't think it would go over well if I blurted that out before we had even gone on our first date.

"I don't know. Are you hungry?"

I wasn't really hungry but I figured that was a good thing. After everything with Aaron before I left my entire mindset for the night was thrown off. The only thing I wanted to do was purge it and so I wasn't so distracted.

"Um, yeah. I can eat. Where do you want to go?"

She looked at me while twirling the end of her hair in her finger. I knew this look. Every guy knew this look. Ashley was into me and if I was any kind of charming we would be in her bed before the night was over. All I needed to do was be cool.

"I'm good with whatever. What are you hungry for?"

Please say dick. Please say dick.

I looked at her and she smiled at me and bit her lower lip. It was basically the same as saying what I was thinking but playing coy about it.

"What about Burger King? I can get us a discount," she smiled at me.

"Yeah, sure. I can do a whopper."

"Tristan," she stood and stared at me awkwardly, "I was joking. I'm not going to fucking Burger King."

I shook my head and stammered to try and play it off.

"Yeah, yeah. I know. I was just calling it on you."

She looked at me oddly again and shook her head slowly.

"You can be a bit of a spaz, you know that?"

I sighed and didn't answer. We had been standing in the doorway outside of her house for a couple of minutes now and things were getting awkward. My mind was a single track and I knew if I could just show her an okay time we would be back at her place riding that track.

Fucking Aaron. Fuck him.

Everything was fine before he grabbed me as I was slipping out of the room. I'd have been fine. We would be laughing and having a good time. I wouldn't be tripping over my tongue right now. Fucking hell. I figured I might as well try for a hail mary and see what happens because this is going down fast.

"Look, honestly, all I want to do is get you out of that dress and see what that ass feels like in my hands."

I stared at her and her eyes widened as she stared back. My eyes locked onto hers and didn't waver. If this was all going to hell I was going to go out in a blaze of horniness. As she was opening her mouth to respond the door opened.

"Ashley? You're still here? Oh, hi there. I'm Ashley's dad."

An older man, gray hair and taller than me stood just inside of the door. My entire body went stiff. How old was she? Did he hear what I just said to her? She didn't live alone? Fuck!

"Oh, hey. Hi. Yeah, hello."

"Oh my god, Dad. Can you go back inside? We're just trying to figure out where to go eat," Ashley grabbed my hand and squeezed it very tight. She pulled me down the walkway to the street and to my car. Her dad disappeared back behind the door after calling out for us to have a good time. I squeezed her hand back and she returned it tighter.

That's good, right?

We moved around to the passenger door and I opened it for her and she slipped inside. I hurried back over to my door and got in, closed it and looked at her as she reached her hand between my legs and grabbed at my crotch and squeezed tightly. My hips flung up to meet her grip and she lunged into me to kiss my lips. I kissed her back but the force of her pushed me back into my door and I had to break our kiss to push us out of the street light.

"Just a min, Just a minute," I was panting trying to catch my breath.

Ashley had a hungry look in her eyes from the other side of the car as if she wanted to devour me right there. I had to deter her from lunging again and pushing me back against the window of the car.

I laughed a little, smiling at her eagerness.

"Ashley. Ash. Girl, slow down."

She shook her head from side to side.

"You said you wanted me out of this dress and to feel your hands on my ass. There's only one way for that to happen."

Her hands went down and balled her dress up her legs, exposing her hips and her black panties as they hugged her tightly. They even looked too small, digging into her skin as it puckered around the lace fabric. She was so fucking thick that even if her hand wasn't kneading my cock I'd still be rock hard.

"Yes, I do," I couldn't stop smiling at her eagerness. I don't know why though, it's not like any of this was funny. It was most likely because she was into me and barring a complete catastrophe we would be fucking tonight.

"But," I couldn't believe that I was trying to get her to stay in her clothes, "we need to get the fuck away from your house. Your dad is probably in there looking out of the window at us. If he sees you pining me up against the window, or we sit here for too much longer he's probably going to come out and see what's going on. Let's go somewhere and we'll see what happens."

She flopped back into her seat and pouted like a spoiled child, but in a cute way.

"Fine. Go. Drive. But I'm taking my hand back," she removed her hand from my crotch and folded her arms in her seat.

"No, you aren't. That's the one thing you're going to keep doing," I grabbed her hand and put it back between my legs. I smashed her palm against my hard cock so I knew she felt it and then started the car and drove off.

We drove away from her house and all the thoughts of dinner, food, anything where the night had been going had disappeared. The only thing I had on my mind was trying to think of a place to take her to fuck that sweet pussy of hers. I was getting antsy as she continued rubbing my erection. My breathing was heavy, although I didn't realize how heavy but she could tell how turned on I was.

Night had settled onto the sky and it was dark enough that headlights blinded anything going on in the other cars on the road. The only way anyone was going to see what she was doing was if we were stopped right next to them at a streetlight or stop sign.

"My hand is getting tired, would you mind if I used my mouth?"

She smiled at me as I flicked my head her way with a shocked grin smeared across my face. Ashley had such a pretty, innocent face that the words were surprising despite what her hands were currently doing. I could tell she used that innocent look on her face to her advantage and she was in full control despite me being the one who is serviced.

I wanted to play it cool and not seem too eager, but also wanted her to drop her face down over my dick and not come up for air until morning.

"You aren't concerned your mouth's going to get too tired though? How will we talk the rest of the night?"

Ashley smiled wickedly while dropping her head down into my lap, "you don't want to listen to me talk."

Her words droned quieter as her face disappeared downward. My eyes left the road and watched her until it was only the back of her head I could see. The dark hair falling over my lap blending into the darkness. The next sensation was her warm breath and wet tongue running along my shaft. My fingers gripped the wheel tight.

A horn blared through shining headlights and I jerked my head upward and veered the car back into the right lane. Ashley flicked the tip of her tongue along the slit on the tip of my cock.

"You're not supposed to lose control of the car until you cum. This doesn't bode well for you Tristan. You're very weak. I could have you wrapped around my finger if this is all it takes," she was being a brat. I loved it.

She didn't give me a chance to respond and dropped her lips over the head and slid most of the length of my erection into her mouth. I groaned loudly and my foot pressed into the gas. I could almost hear her chuckle against my cock as the engine whirred faster with my foot pressing into the pedal. I needed to find somewhere to stop so I could enjoy this.

"Fuck, that feels so fucking good, Ashley," I moaned.

One hand gripped the wheel as the other rested on the back of her head. There was a slow force, slightly more than gravity that pushed my hand down on the back of her head. I wanted to feel it all in her mouth and I wanted her to hear her gagging on it. Choking, messy sounds and strings of saliva and cum stretched from my cock to her lips were running through my head. Every porn I had tried to masturbate to in the last few days was what I wanted this to turn into. She was my cumslut. She was my whore.

"My god it feels so fucking good finally having a girl's lips on my dick."

The words were innocent enough but Ashley's brattiness caught them and swatted back.

"Why? Have you had a man's lips on your dick recently?"

She pulled up off of my cock and smirked at me. Her answer was so playful and cute. A proper answer by any sort of dominant, top, master, sir would have told her to shut up and shove her face back onto her task and then hold her there to make her choke and gag for a few moments. But that's not what I did.

All of my insecurities rushed into the forefront of my mind. Every second with Aaron had wiped the incredible feeling of having Ashley servicing my dick out of me. My face turned red, as if someone injected me with dye and it spread across from cheek to cheek, forehead to neck. She noticed immediately and her wide, playful grin faltered.

"No!" I had said this way too forcefully. It came out much harder than I had intended.

"Why would you say that? When would I have ever had a man's," I paused, not able to continue the sentence to finish it and instead repeating myself.

"Why would you say that?"

The look on my face was anger and confusion. Of course I knew why she said it and I knew why it was bothering me so much, but she didn't. If she didn't know why it would bother me so much then why would she even bring it up. These were questions for the universe and its sick fucking game it had me in. Why couldn't it just let me have this night to be happy and forget?

Ashley stuttered an apology and pulled back from hovering over my lap to sit back in her seat. She used the back of her hand to wipe the saliva from her lips. My cock was softening and left exposed. She pulled her dress down over her knee. The silence sat heavily in the car as we drove aimlessly.

"I'm sorry. God, Ashley, I don't know why I said it like that."

She shook her head indicating it was okay while also indicating she was feeling awkward and it was clearly not okay.

"No, Ash. It's not you. I wasn't even really talking to you. When I was younger, as a kid, I was teased. A lot. I was just kind of like I am now. Wirey. Slim."

I started rambling, but with a purpose. Most of what I was telling her wasn't a lie. It all happened. I was teased and called names. I wasn't good at sports and some of the bully, jock type guys would call me a faggot. That wasn't what was happening here though. I was lying through my teeth to smooth over the moment, trying to back everything up to try and salvage the night.

"I was called gay because I didn't have a girlfriend and because I liked video games. They, the guys, the jerks, they would spread rumors that I spent my entire weekend taking turns being on my hands and knees with the other losers. I'm sorry, I just, I guess trauma comes up in the most random places sometimes and you didn't have anything to do with it. I just didn't expect it to come up there. I've been pretty good at being able to forget it but it was so unexpected that I slipped up. Ashley, I'm really sorry."

She doesn't respond. I continued driving.

After a few minutes of aimless driving I consider turning around and taking her home. The night started off bad and was saved by some bizarre left turns on my part, but maybe it wasn't meant to be. Maybe I needed to get my head straight before I could actually be with someone who isn't using me for sexual gratification.

"Why are you like this?" She speaks up at last as I turn my signal to go left and start to drive her home.

"Like what?" I hold my voice of any resentment and try to keep it purely a question.

"We haven't known each other very long but you're so hit and miss. One moment you're cool and hot and I want to get to know you more. Then, within the same five minutes, you're awkward and weird and I don't know why you're acting the way you do. I think you're into me and then I have no idea what you're thinking. I thought maybe if we went out-," I cut her off before she goes on too far.

"Ash, stop. No it's," I sigh and consider telling her the truth. I let the moment in time run like a flash through my mind. I'd tell her that I like her and it's what is causing all of this strangeness, or part of it. Then I tell her about losing my job and Aaron and how he wouldn't let me go for a month until I found something. After that I tell her about his offer, rejecting it, meeting her and then not wanting to find a new place or move and making a rash decision in accepting his offer.

But I don't tell her that. Why would I? What kind of bizarre situation would ever warrant me telling her about the deal I made with Aaron? Yes, I've sucked my roommates huge fucking cock three times now. He even sucked mine and I masturbated and ejaculated while sucking his one of those times. In fact, I sucked his cock right before coming to see you, did you taste it when you kissed me? To think, it's all I have to do and I don't have to pay rent. What a deal, huh?

"I'm sorry. I'm really sorry. I don't mean to trauma dump on you like this all on our first date."

Trauma dump? Where the fuck did I come up with that? I must have seen it scrolling Twitter or something. I could see in her face that it had some merit though. She wasn't hard-faced and staring out of the window, but looking at me as I talked. I tried to turn to meet her gaze every few moments to try and convey a connection.

"The truth is that it's been a long time since I've been with a girl. Off the top of my head I can't remember when I last got broken up with and finding another girl that was worth risking being hurt again was a lot. It wasn't until you that I thought it would be worth trying."

I let the words sink in and stop talking for a moment, then I have an idea, "and on top of that I have my damn roommate threatening to throw me out. I lose my job and go right out and get one and he threatens to throw me out and all of my stuff onto the street if I don't pay him right away."

"That's why you're trying to get a job at Burger King?"

Her voice had an inquisitive realization in it, as if she was piecing together her own questions about me. I looked over at her and the upset look on her face had melted away.

"I'm sorry, Tristan. I didn't think you might be going through some stuff also. I guess a lot of people don't really think of things like that. That other people have issues and their own lives. I hope I haven't made things more difficult for you."

"No. No, baby, no. You've been amazing. Honestly you've been the only good thing the last week. The idea of taking you out has been the only thing that's gotten me through all of shit I've been dealing with."

Okay, so that wasn't necessarily a lie. Thinking about getting with Ashley has been the only thing that has allowed me to have Aaron's dick in my mouth multiple times. Tonight has been a rollercoaster but it's trending upward and she is still the only person I want to be with right now.

As I'm taking another turn at an intersection the air in the car pushes towards me. Ashley's hand is rubbing across my thigh and has engaged my deflated penis. She begins tugging at it gently, stroking it as it flops about in her hand. Her fingers dive deep below my jeans and rub the seam leading to my anus. I tense up and whimper, which causes her to smile with an audible satisfaction, "find somewhere to park."

There's a shopping center up ahead and as it's getting later in the evening most of the spots are empty with a few cars peppered throughout the parking lot. I pull in and park towards the outskirts of the shopping center under a dimly lit area due to one of the light poles not working. I put the car in park and turn off the engine. That's all it takes for Ashley to lunge across the car again, this time mounting me and driving her tongue into my mouth.

Ashley's hips grind against me. I can feel the soft cotton of her panties. The zipper to my jeans is causing me to twitch awkwardly so I reach down, loop my thumbs in the waistband of my jeans and underwear and shove them both down below my knees. Her panty-clad bottom settles nicely against my waist and she continues grinding her panties against me. It takes very little time for my cock to grow fully erect. She's hiking up her dress and pulling it over her shoulders. Our kiss breaks and she tosses the dress in the backseat.

Her tits are magnificent. They are spilling out of the gigantic black bra that is desperately trying to hold them in. With each thrust of her hips she grinds her waist down in a twisting motion to coax my dick into the hardest erection it's ever felt, while at the same time causing her massive tits to bounce and ripple in my face. Her hot breath floods down over me and I can't wait to fuck her anymore.

My hands move like wildfire. I grab ahold of my erection with one hand and grasp her panties between her thighs with the other. With her panties pulled to the side I position my tip to her waiting, dampened pussy and she sinks down onto me with a flush of steam pouring from both of us. Our mouths, our bodies and our tension all let loose as I entered her. She drops her mouth open and a pained expression pours over her face. She screams out.

"Oh, GOD, Fuck!"

That was the most intense thing any woman has ever said the first time we had sex. It's driving me wild and I've eagerly started thrusting my hips up into her, pushing deeper into her tightness and causing her to bury her face in my neck after another pained expression and seething gasp.

I was all of the way inside of her now, I could feel her uneasily settled against my thighs. Her movements were short and uneasy. She was trembling and muttering the same combination of curse words.

My weight shifts, trying to get a better angle to be able to push inside of her but nothing feels right. Though, with each movement Ashley is slowly bouncing more and more eagerly. Her hips are rocking back and forth and she pulls down the cups to her bra, pinching and twisting her nipples as they spill out gloriously.

"Mmm, fuck, Ashley," I begin as I'm readying to ask her if we can move to the backseat as I can't quite get comfortable, but she cries out louder as I push my hips and slide along the seat.

"Oh FUCK, Tristaa-aan," the words growl from her chest and her mouth drops open. She slams herself down on my waist and then her body lets loose into an intense orgasm. Her legs are shaking and she starts to erupt. I can feel her gushing between her legs onto me. I've heard of female ejaculation but never had experienced it or even really watched any videos of it aside from comically overblown ones. It turns out they weren't comically overblown.

I'm thoroughly soaked. The seat of my car is drenched. Both Ashley and my waist and thighs are stained from her sexual explosion. She is laying flat against me, panting. Every few moments her body has an intense shiver, like an aftershock and she moans into my shoulder as if she's having another orgasm along with it. The car now reeks of musky sex.

"Oh my god. I am so sorry. I never," Ashley is whispering weakly into my neck now.

"No. No, its okay. It was amazing. Don't worry about it."

I'm quick to try and ease any kind of embarrassment she might be feeling. I don't want her to feel like that. I'm flattered that I was able to cause that kind of orgasm in her actually and it makes me feel better. It gives me a sense of manliness.