My Roommate Made Me a Sissy

CH 10

My mind was messed up from the way things ended with Aaron. It was worse than before when I wasn't the one who initiated it and I was going out to meet Ashley. I didn't want to think about it but it kept creeping back into my head the entire drive over to her place. Worst of it all was that I felt myself get hard whenever I started to think about what would have happened if he had followed me into the room.

Fuck. I need Ashley, man. I need her bad.

When I pulled up to her place I texted her that I'm here and that I need to see some titties, pronto.

Shut up, she texted back, I'll be out in a minute.

After a few minutes my phone dinged and I picked it up. It was Ashley in her lingerie she surprised me with earlier, but this time the top was pulled down and she was leaning forward, her tits were hanging and only covering her nipples with her fingers.

Fuuuuck babe, get your ass out here cause we gonna fuck, I typed immediately.

She lol'd me and said no, that was for tonight, dinner first, and a kissy emoji.

I was so pent up and frustrated I started rubbing my dick through my pants. Pressing my palm into the bulge I pushed down on it and slide my palm down the length. It wasn't enough, although I didn't want to pull my dick out and start stroking it in the car out in front of her house either.

My dick was hard and I felt so needy I pinched the shaft of it in my pants and began rubbing. I ran my fingers up and down the length of it as my dick stretched down my leg. It was only a few inches as I wasn't nearly as well as endowed as Aaron, but it started to feel really good. My mouth dropped open and I felt my heart begin to race, but the rubbing and slow stroking wasn't enough. The entire experience was just adding to my frustration and it made me want to pull my dick out even more and jerk off, so I pinched my shaft between my thumb and forefinger and began to rub it back and forth on my thigh. I was very surprised to find out after a few seconds it was working.

My eyes continually shot up to where Ashley's front door was. I was going to stop the moment I saw her but at this point the feeling was growing so intense I had to keep going until I absolutely had to stop. My dick was grinding into my thigh, the soft feeling of the skin of my inner thigh must have helped a lot because I was fully erect and breathing heavily. Soft moans started to stumble past my lips while I sat back in my seat and pushed my feet past the pedals of the car. I contemplated unzipping my pants and going for it a third time but somehow resisted.

The speed of my rubbing increased. My mouth dropped open and my eyes were closed. I told myself that I needed to stop but the need inside of me was winning. It's amazing the power an orgasm has over us and what we will do to achieve it. I needed to cum and I didn't care about anything else.

The friction between my dick and my thigh and the jeans being pressed into it was too much. I felt the release shooting through me and rubbed right through it. My orgasm shot out and I could feel it push through my shaft as I continued to rub. Fingers pinched and rubbed as I let it out all over my thigh. My body shuddered uncontrollably and I whimpered a deep, gratifying sigh as the post-nut serenity sank over me. I laid back, my fingers rubbing a few moments past ejaculation and then falling to my side, then jolted forward in shock as the passenger door opened.

"Hey," Ashley said, smiling.

My heart leapt through my chest and I felt like I was instantly sweating. Did she see what I was doing?! Did she see what I did?! Did anyone see?!

"I, hey, I, uh, hey, I," the words tripped out of my mouth.

"Here, let me give you a kiss, poor baby," she leaned across the car and placed her hand on my knee, then started to run it up my inner thigh. I jerked away from her before she reached the wet spot soaking my jeans.

"Uh no, no. Um. Later. Let's, like you said."

I couldn't form a sentence to save my life. She looked at me funny and then gave a little shrug before sitting back in her seat.

"I thought you wanted to see some titties and we gonna fuck right now or whatever?" Ashley slouched, looking out of the window.

"Uh yeah, I did. I want to. But then I thought about what you said is all," I reached out and grabbed her thigh and gave it a squeeze of reassurance, "I want to be able to give it to you hard and long tonight. All night. Not all squished up in my fuckin car."

"Alright, I guess," she said, somewhat convinced.

The drive to the restaurant was fairly quiet. I tried to start a conversation a couple of times but Ashley didn't do much to continue it. Her answers weren't dismissive and she didn't seem like she was mad, but she was usually much more of a talker than this and I could tell there was something wrong, so before we went in I asked if she was alright."

"You good, Ash?" I set my hand on her thigh and gave it a gentle squeeze.

"Uh huh," is all she said.

"You don't seem it."

"It's, nothing," she trailed off.

"Obviously its something. Usually you don't shut up the whole way when we're driving somewhere."

Fuck. That was a stupid thing to say, but I was kind of frustrated. Everything was going alright. I got out of the house from Aaron and didn't have to submit to him. I actually played him in a way and I was feeling really good about how the entire experience went. I left the house feeling good for the first time in a long time and now she's bringing me down. The night I'm gonna get to fuck that tight, sweet pussy and she's gotta pull this shit. I was getting annoyed and as much as I tried to keep it in I let it slip.

"So what, I never shut up now? You're saying I talk too much?" She was pissed.

"No, that isn't what I meant. Just, was saying, usually you talk the whole time and I'm just letting you say your shit."

"Right, because you ain't ever got shit to say Tristan. I'm always the one talking. I'm always the one saying we should do shit. I'm always the one trying to fuck you and you're always the one pulling away. You say you want me bad but then when I try to fuckin kiss you, you pull away like I'm a fuckin guy or something."

My mind went somewhere completely different as she said that last part, about if she were a guy. I should have corrected her or convinced her differently. There are so many things I could have done to try to convince her it was alright or that I was into her as much as she was into me, but the thing I focused on was wondering what I would do if Aaron tried to kiss me.

I started to reason with myself, no thinking it was something that he would do. He never made an inclination towards putting his lips to mine. What would I do if he did? Would it be worse than letting him fuck my ass? Kissing is so romantic and intimate, while fucking is just sex. If I kissed him did that mean I'd want it, all of it?

"See, nothing to say. Just staring at me with those big, dumb eyes," Ashley waved her hand in front of my face as I zoned out.

"No, Ash, come on. I'm sorry. I'm just not as good as you at some of this stuff. Like, I've always been quiet and never had a lot to say. I like it when you go on and on and shit because it fills the silence. If I was with someone like me I don't know what we'd ever talk about. I wasn't saying something was bad that you talked so much, just that I noticed you hadn't so it felt awkward."

"Well, that isn't even all of it though. You always make it seem like you don't want to touch me when we're together."

She was softening. The desire to be mad was there but it was waning. I don't think she wanted to start a fight but the way I brushed her off in the car must have really upset her. I can't believe I can't control my impulses enough to not jerk off in the car. My entire world was becoming about sexual gratification and I wasn't handling it well.

"Of course I do. Like I said, tonight. Tonight you'll see how much I'm into you and how badly I want to touch, and," I nuzzled my face into her cheek sweetly before smiling out the last few words, "fuck you until you soak your sheets like you did my car."

Ashley gasped, turned and smacked at me while laughing in disgust.

"Tristan! Oh my god, I can't believe you said that!"

I flung my hands up in defense and she continued to swat at me and called me perverted, disgusting and an ass.

"Yeah, but you love that stuff about me, don't you?" I leaned in for a kiss, reaching out to take her hand and lace my fingers through hers.

"Mmhmm," was all she said, but she leaned in for the kiss and squeezed our hands tight together as we laced our fingers.

We got out of the car and she immediately reached for my hand again, lacing fingers just like before and swinging our arms in sync as we walked in.

The dinner went well. Ashley perked back up tremendously and was her chattering self while telling me all about the gossip and drama going on in her friend group and at work.

"Did they ever call you to offer you the job?" She leaned forward with her arms resting underneath her breasts, propping them up on the table in full display. The scoop neck of her top made them stand out and look incredible. I was getting hard again and all I could think about was burying myself between them.

"Oh, yeah. Yeah they did. I'm supposed to start this weekend, which will be nice so I can get paid a full pay and not start off in the middle of the week."

That was the first question I asked when they called to offer me the job, "when can I start?"

I wanted to start right away so when I got paid I'd have a full week to give to Aaron and be done with this gay shit as soon as possible.

"Oh, nice. That'll be fun. I don't work this weekend but at least when we do finally start to work together you'll have a little bit of training so I don't have to show you everything," she leaned forward onto the table in mock exhaustion.

"You're quite helpless, you know," she smiled with a wink at me and reached her hand across the table to clasp mine, squeezing it again and smiling at me. Looking into her eyes, she really seemed happy and practically beaming and I started to feel bad that I didn't give her more attention. She really was a great girlfriend.

"You know," I said as I squeezed her hand back, "I heard Aaron say he's going away sometime soon. A guy's weekend or something. They head out into a cabin by the lake or something and drink and do all kinds of shit. Anyways, when they're away I'll have the place to myself all weekend. Why don't you come spend the weekend with me? You can walk around in your panties all weekend," I grinned and bit my lower lip while staring at her.

Ashley's eyebrows raised and her smile perked up. She pulled her hand from mine and clapped them together daintily, "oh my god, yes! That will be so much fun. Oh my god, oh my god. I can't wait. Do they have a date? I'll need to figure out everything I'm taking over."

"No date yet, no. But he said sometime in the next few weeks. I'll let you know as soon as I know."

The possibility of having her at my place for an entire weekend alone was making my head swim. It was going to be perfect because we'd be fucking all weekend. I could turn the place that I live from a reminder of all of the dick that I've been sucking into a place where I've fucked her in every corner of every room. A grin spread across my face when I thought of fucking her in Aaron's bed just in hopes she would squirt all over his sheets and have her musky scent soak into his mattress.

When the check came I grabbed it as she was reaching for it. Ashley had paid for so many lunches and dinners while I was off work I figured I could cover one since I'm going to start getting paid next week.

"Here, let me. You've been my sugar momma for too long," I smiled at her and took the check.

"Are you sure you aren't working yet? I really don't mind."

"Yeah, I got it," I handed the server my credit card, the last bit of money I had in my name would cover it. I could go paying the minimum for a couple of months until I got my feet under me.

"I mean, why not. I'm getting paid next week. Then I'll be a true gentleman and make sure I'm the one picking up dinner," I took her hand and gave it a kiss on the knuckles.

"Two weeks," she said, smiling back at the kiss.

"Huh?"

"Two weeks," she repeated.

"Two weeks what?" I looked at her, confused what she was talking about, thinking maybe she misconstrued when Aaron was going away even though I already told her I didn't know.

"You said you were getting paid next week, but we get paid bi-weekly. You won't get paid for two weeks."

"What?" My fingers let go of hers.

"We get paid bi-weekly, so I guess I'll be picking up lunch for a couple of weeks unless you sneak a bunch of french fries when it's dead," she smiled to herself as I felt the blood drain from my face.

"So I'm not getting paid this next Friday? Not today but a week from today?"

She merely shook her head and put a couple of the hard candies that came back with the receipt into her purse.

The drive home was a blur. I felt like I was on auto-pilot and I didn't even remember most of the turns and stops that I had to make, they were just done and when we got back to her place it felt like I blinked from sitting at the table for dinner.

"Come on," she leaned in and kissed my lips before running up the steps to her empty house.

I walk like a zombie up her steps and into her house. Even though the lights are out I can see her smile beaming through the darkness as she takes my hand and shows me to every room, telling me little stories about things she's done and memories she's had in each of them. Eventually she leads me to the stairs and stands in front of them, taking both of my hands.

"So, do you want to come up to my room and fool around?"

The smile on her face looked like it hurt, it was so big. She nodded up the stairs and started walking up ahead of me, slowly taking each stair and looking as if she was leaning forward so her plump behind was in my face and showing off with each step up.

When we got to her door she told me to go in and sit on the bed, that she would be right in but had to run to, "freshen herself up."

I was still stunned at finding out I wouldn't get paid for two weeks. What was I going to tell Aaron? Everything had gone so smoothly this morning and now it was all crashing down on top of me. All I could expect was for him to push me down on the ground and fuck me the moment the words came out of my mouth. No lube. No preparation. Just his massive dick shoving itself into my virgin asshole. I grimaced at the thought of it and didn't know if I was able to shake it away before Ashley showed up in the doorway wearing the lingerie that had turned me on so much via text.

She was stunning, like a Victoria Secret model. Although she was vertically challenged, being barely over five feet tall, every other aspect about her physically accentuated each other. Her curves fell perfectly on her frame to keep her from looking plump or squat, but at the same time they gave her body an incredible shape that would make my knees give just a little bit every time I saw her.

I think I corrected my face in time, as she never stopped or made a reaction and by the time I realized it my mouth was open in shock at her, but mostly in exasperation of not knowing what I was going to tell Aaron and how I was going to get out of a raw dog fucking when I did. She walked over and stood in front of me, reaching down to put my hands on her hips.

"You like?" She looked down at me. Her voluptuous bosom barely held in the cups of the one piece. When she placed herself down on my lap with a plop her chest rippled like disturbed water and I was stuck in a place between arousal and fear.

"Fuck me," she said, grabbing me by the collar and pulling me in to kiss her.

I muffled a response which wasn't a word but she never knew it as her lips hit me hard and pushed us both back onto her bed. My hands just happened to slip back onto her thighs as she pushed me back. Her lips kissed away from my mouth and down my neck, moaning as I laid there unable to escape the fog I was trapped in.

Ashley began to kiss down my body and reached for my pants. She lowered herself, unbuttoning them and then I remembered what happened earlier that night and the cum drying into my pants and boxers. It was most likely too dark for her to see but I didn't want to risk it. I reached down and grabbed her, flipping her over so she was on the bed on her back and I dropped down between her legs. She let out an "oof!"

I had to do something. My brain wasn't working and all I could think about was Aaron. Why?! What is so fucked up that I've got Ashley throwing herself at me and all I can think about is fucking Aaron and how he's going to pound my ass for not making rent again.

My lips touched her inner thigh and I heard her inhale sharply. I knew what I needed to do now, the same thing that I did to Aaron. If I was able to give her an orgasm, just like the one she had in my car, then she would be so exhausted that I wouldn't have to worry about fucking her with my mind so torn and stressed out. I just needed to make her orgasm and I could worry about fucking her for another time.

I kissed higher on her inner thigh. As my plan started to come into focus, at least my immediate plan of appeasing Ashley so she doesn't get more mad at me, and then I can figure out what I'm going to do about Aaron. She writhed on the bed and her heels dug into my shoulder blades while the heat of my breath crept up between her legs. I muffled a mock moan against her skin while I kissed and sucked at her inner thigh.

She was moving about on the bed above me, I looked up and she was propped up on her elbows with the straps to her lingerie pulled off of her shoulders and her breasts exposed. They looked incredible, the massive fleshy pillows and their pert darkened pink nipples, yet I wasn't nearly as hard as I should be in this situation. I plunged my lips forward to the fabric covering her pussy and kissed along its edges while I reached down between my legs and grabbed at my dick through my pants, pulling on it trying to get it to stay hard.. Ashley threw her head back and continued to curl her heels into my back, edging my lips to go further.

"Fuck, Tristan, fuck me," she moaned.

I could feel her hands reaching down grabbing for my hair to try and pull me up so I could stand back and fuck her. No matter how hard I tried to put myself in the moment, in this incredible moment, I kept having my thoughts drift to Aaron. Him and his gigantic cock and how he was going to make me pay rent bent over and screaming. My tongue was trailing along the fabric of Ashley's lingerie between her legs. It was a fingertip away from sliding into her pussy and I couldn't get Aaron's massive cock out of my head.

She was whimpering and moaning. There was need behind each sound she made and in a moment it would turn from sexual frustration in the heat of the moment to her asking why I wouldn't fuck her. Then I'd have to tell her about everything and I don't know if she would still be my girlfriend after that. I was trying but I wasn't satisfying her. Could I ever? I'm going to give myself an inferiority complex if I keep this up.

I moaned loudly into her and hooked my finger in her lingerie, pulling it aside and exposing her to me. She squirmed on the bed and let out a loud groan. I plunged my tongue inside and she screamed.

"Oh god yes! Fuck me! I want to feel you inside of me!"

I did the only thing I could think of and slid my fingers into her. My index and middle finger tightly held together pushed into her slick pussy and she reacted around me. She gasped and her heels pushed into my back again. She started to scream but muffled her words into a hard groan. I wrapped my lips around her clit and sucked to go along with my fingers and Ashley started to whimper and her voice cried out in a high pitched whine. It was working, I was going to cum and I didn't have to fuck her.