Tess

Please feel free to comment or send me a message, I appreciate any feedback on my stories. I am publishing them out of order to keep it interesting for you. Enjoy!

After I got out of the Navy I used my G.I. Bill to go to school and ended up getting a job as a Data Analyst. I ended up in a small town in central California. When I say 'small town' I mean one of those smaller cities that borders a big city and is included in the 'Metropolitan population'.

When I applied for the job it was the middle of summer and I was thankful for the air conditioning when I showed up for the interview. They had Ansel Adams posters hanging on the walls and an extremely comfortable couch in the lobby. Thankfully the couch wasn't leather, the air conditioning was nice but something about a leather couch makes me uncomfortable. I don't know exactly what it is, but I don't like them. I don't like looking at them, sitting on them, moving them, or even thinking about such things.

I was called back and had my interview went well. The boss (David) didn't seem to care much about my qualifications, rather he was interested in my grades in school. He said that the job was a breeze if you're a good student and teachable. I made Dean's List in school and I graduated my Navy training with a 98% in my class. In fact, my picture is still on the wall in the halls of the Pensacola schoolhouse because we were a "hall of fame" class.

The rest of my interview was basically talking about movies and video games and books. He showed me around the office and introduced me to the other guys and the office ladies as "the new analyst" so I was pretty sure I got the job. That was confirmed when we went back to the office and he offered me the job and asked me when I could start. He told me that he was hiring a Customer Service Representative and that he wanted her and I to start on the same day, so we coordinated the date, shook hands, and I went home.

My start date arrived and I showed up to work in a light blue polo and some nice, dark blue jeans. David greeted me and appeared to be wearing a very similar outfit.

"Hey Jason, go ahead and have a seat in the conference room. Once Tess gets here I'll bring in all the orientation packets and let you guys click your way through the PowerPoints."

Tess arrived and I looked her over without being obvious about it. She was almost as tall as me, I would put her around 5-8 or 5-9. She wasn't exactly skinny or fit, but she wasn't fat either. She wore a green dress that had a V-neck but didn't show any cleavage. Her breasts were big enough to get a handful, but not big enough to notice in her dress. She wore plain silver stud earrings and had a small star tattooed on the inside of each wrist. The one thing that stood out to me was her ass.

Her ass was the only part of her body that the dress clung to, it stuck out like it was begging to be slapped and fucked. If Tess went to the gym, the only thing she did were squats. Years later I still stroke myself to the thought of her ass. She introduced herself and pulled out a chair then sat down.

We exchanged pleasantries and as we clicked through the PowerPoints and it became clear that she grew up with brothers and always had male friends. Every time she saw something that even vaguely resembles a penis or boobs she pointed it out and we laughed. We got along and as a formality we exchanged phone numbers, you know, since we were coworkers. Plus, she had a boyfriend named Ernie.

Months went by and it also became apparent that Tess was a very open person. Especially when she ended things with Ernie. That was a doozy. Turns out that they didn't live together and every time she brought it up her would avoid the topic or find some reason that they shouldn't. Well one weekend she ran into Ernie out in public when he said he was going to see his parents and he was with a 5 year old kid. I guess Ernie had been hiding his baby mama and kid from Tess the whole time. What's worse is that he was actually dating baby mama but she didn't want to let him move in unless they got married, so he basically juggled Tess in his situation.

Tess and I were smoking a cigarette on break one day after discussing Ernie and she brought up their sex life.

"You know, I think I get why he lied though. Most girls don't do anal, and the girls who do don't really enjoy it, they do it because guys enjoy it. But my medical condition makes vaginal sex painful so I've been taking it in the ass for so long that I've come to enjoy it and it actually makes me cum." She took a drag of her cigarette as I nearly choked on the smoke from mine.

I looked at her in astonishment. We had talked openly about sex and sexual experiences before, but it was mainly in vague terms and describing an overall experience. We had never been that straightforward about something like that and never about a specific act.

"You know," she continued, " I was almost going to try to get him to play out my fantasy. Fucking prick."

"What?" I wasn't really asking a question. I was really just exclaiming because I was so taken aback. I found her mildly attractive and yes, I had fantasized about her a few times, but I had never actually thought about trying to fuck her. Well she must have thought I was intrigued about her fantasy because she kind of half-grinned for a second before continuing with a straight face.

"Yeah, honestly probably one of the most common female fantasies. Single woman alone at home taking a shower, forgets to lock the front door, some guy in cargo pants and a ski mask yanks her out of the shower and has his way with her. That's pretty much it. I think all women have fantasies about being forced, I just want it to feel real. I want to get slapped around, choked hard, thrown to the floor. That kind of thing. If I'm not crying and bruised by the end of it I'm not cumming."

Holy shit. This woman had a rape fantasy. And she exclusively did anal so she was confessing to me rather casually that she had an anal rape fantasy. I was beyond stunned. Before I could say anything she looked at the time on her phone and muttered 'about that time', put out her cigarette and went inside.

From break until lunch all I could think about was what she had said. I couldn't believe that she had just casually told me all of that. We didn't see each other on lunch, but at our last break we talked again. We chit-chatted about random stuff and towards the end of break she asked what I had planned after work.

"Nothing much really. Probably gonna eat, take a shower, watch some TV, play some video games, and pass out. What about you?"

She seemed to genuinely have to think about her answer. "I don't really know. Now that I'm single I don't really have after work plans all that often. Honestly I think I'm just gonna go home and take a shower. I have a really bad habit of leaving my front door unlocked so we'll see if anything interesting happens." She looked at me as she put her cigarette out I could see from her face that it looked like she was biting the insides of her cheek to keep from smiling.

Throughout the remaining work day she would cast glances my way and i would catch her staring at my crotch. She had given me an invitation to her fantasy. She wanted me to follow her home and roughly fuck her. She wanted me to violate her in any way I saw fit. I became more amd more horny until I didn't even question it. I was doing it. I was going to follow her home and rape her. Thinking about it and saying it like that doesn't sound right since it isn't rape if it's consensual, but you get the point.

We clocked out and everyone said goodbye to each other, got in our cars and went our separate ways. Except for me. I pulled out of the parking lot last and stayed a few cars behind her and followed her across town to her house. I didn't know where she lived and I didn't want to miss my opportunity. Finally I saw her pull into a driveway. I parked a few houses down on the curb and watched her walk into the house and shut the door.

I thought about what she said and went to my trunk where I kept my emergency supplies. I found my winter stash and rummaged through it. Ice scraper, snow chains, jacket, gloves.... Bingo! Ski mask. I shoved it in my pocket and got back in my car to survey the house. I looked around and saw her through the kitchen windows putting her lunch dishes in the sink, she left the kitchen then I didn't see her. A light went on in a different room. I exited my car and approached the house.

I tried my best to look inconspicuous, the last thing I needed was the police showing up. I looked through the window and saw her walk into her bathroom and turn on the shower. She looked over her shoulder with a half-grin, then got in the shower and shut the clear glass door. Now was my chance.

I walked to the front door and tried the handle. It was unlocked. I slowly and quietly turned the handle and opened the door, walked in, then closed and locked the door behind me. I slipped the ski mask on and began to slowly walk through the foreign house, following the sound of the shower. I approached the open door of the bedroom and walked in. My heart was pounding. I simultaneously felt like I should leave while feeling like I was about to have the fuck of my life.

Looking around the corner I could see into the master bathroom and had eyes on the shower. The glass was clear but about half-fogged. I could see her tits very clearly. She had those perfect thick nipples that stuck out and begged to be pinched and chewed, or to have clamps attached to. From where I was standing and peeking it looked like they were pierced diagonally. From what I could tell through the fogged lower half of the glass, I was right about her figure. Her stomach didn't appear to be flat, but she wasn't what you would consider fat. Her ass looked inviting even through the glass that was getting harder to see through.

As I was staring at her ass I noticed something. There appeared to be some sort of hose dangling behind her that I traced back to the shower head. I wasn't sure exactly what it was, but I had my fill of looking. It was time to do what I came for and take what I wanted. I approached the shower door and yanked it open.

Tess jerked like she just had a good jump scare and screamed. I wasn't sure what exactly to do so I reached my hand in the shower and grabbed her by the hair on the back of the head.

"Shut up bitch! Get out here!" She began to comply but hesitated and reached her hand behind her to her ass where the hose was attached. I forcefully slapped her arm down and she yelped.

"I'll take care of that." I said as I reached behind her and grabbed the hose and yanked (maybe harder than I should have). It turns out that it was some sort of butt plug shower enema attachment. The plug wasn't exactly small either. It wasn't insanely large, but definitely bigger enough that you had to be experienced to insert it. I let the plug drop to the shower floor with a klang as the water forcefully evacuated from her insides into the shower. I reached over and shut off the water and tightened my grip on her hair.

"Get over here whore!" I was going all in. I lowered my arm and she bent forward to comply, crying and grasping at my arm to try and remove it, to no avail. I stopped and looked around her room trying to decide where to fuck her. I straightened her upright and as I let go of her hair I shoved with both hands. She tumbled forward onto the bed naked and face-first. I stared at her naked ass and felt my cock getting hard. She started to get up and turn around, she looked at me with a look of fear, while at the same time fighting a smile. I remembered what she said: "if I'm not crying and bruised I'm not cumming."

"Get down bitch!" I said as I slapped her. Her face jerked away and she put her face down in her pillow as she exploded in tears and sobs. I began to take off my belt and pull my pants down as I noticed that she had put her ass slightly up in the air, inviting me in. I pulled my cock out and climbed on the bed, mounting her.

"You like it in the ass, huh? Well you're gonna fucking get it in your ass, whore!" Now, I don't have some crazy, foot-long anaconda, but it's nothing to be ashamed of. About 7.5", but the thing is, I'm THICK. I've been turned down before based on my girth. I guess it just depends on whether a girl likes it deep or wide. I held her down by the back of the neck with one hand and held my swollen appendage in the other. As I got ready to insert I felt her ass slowly lift toward me, begging me to fuck her. I pressed my head against her pulsating asshole and shoved in my full length as hard as I could. She screamed into the pillow and began to thrash around. She clearly wasn't expecting to be stretched out like this.

I pulled about halfway out and thrust forward again. I could feel a little bit of water left inside of her from the enema. I continued thrusting. Each time I tried to go harder and deeper. I would lift my body until only the tip of my cock was concealed inside of her throbbing asshole, then slammed back into her with all my weight. Each time I bottomed out, I could hear her sobs slowly turn into grunts, then moans. I gave one really good thrust, forcing myself as deep as I could go until she was forced to try to crawl away from me.

I pulled out of her ass so that I didn't cum yet and as soon as I let go of her with my hands, she squirmed out from under me and scrambled off the bed and on her knees to her dresser. I hopped off the bed and chased her down. I grabbed her by the hair on the back of her head again and yanked her. The drawer she was reaching for was about halfway open, I ignored it.

Since she was already on her knees I figured I would take advantage of the position. I pressed my cock against her lips.

"Suck it!" She shook her head and grunted no as the tears came back to her eyes. She was a champ, she knew what she wanted and she played the part well. I could tell that she had slid one hand between her naked legs. I decided to let her keep at it.

"I said, be a good fucking whore and open your mouth!" I leaned down to grab her face, forced my fingers in her mouth, then pried her jaw open.

"If you fucking bite me, I swear to god you're going to be giving gum-jobs for the rest of your life." As I held her jaw open I brought my cock back to her face and began to shove it in. She winced as I hit the back of her throat. I placed both hands on the back of her head and gripped her by the hair. Her free hand reached up and pretended to try to push me off of her. I applied pressure to her head and began to press my way into her throat. I felt her throat contract as she gagged, with a firm grip on her head and my cock blocking her breath, I began to fuck her throat like I fucked her ass. I throat fucked her like I had only ever seen in 'brutal throat fuck' videos. I was close to cumming when I noticed her gagging and screaming stopped, then her arms went limp and fell to her sides.

She had passed out. She never tapped out for air. She trusted me enough to let me suffocate her with my cock. I slowly pulled out of her throat and mouth, then let go. She slumped over on her side. Her face was red and her chin and tits covered in slobber. I wasn't sure how to wake her. She was breathing but passed out. I looked at the half-open dresser drawer and saw that she clearly opened it for a reason. In the drawer was an assortment of dildos, butt plugs, vibrators, lube, and restraints.

I grabbed the restraints and fastened them to her arms and legs. She slowly regained consciousness as I reached in the drawer and grabbed the first dildo I saw and some lube. The dildo was the size I had never seen in person, only in porn videos and only ever in the ass. It was huge. It was neon in color and looked like it had dragon scales on it. When I say that it was big, I mean that it was massive. Like years of practice to insert huge. I squirted some lube on it and bent down to her. She began crying again and begging me to stop.

"Shut the fuck up. You're gonna take this and you're gonna like it whore." She smiled, only for an instant, before she began begging again. I got one my knees behind her and pressed the tip of the monster dildo against her puckered asshole. It was still slightly gaping from my rough pounding, I could easily slip a finger in without actually touching her, but the dildo was bigger. I grabbed it by the base and twisted as I inserted it. This time I went slow. Inch by inch the dildo made it's way inside of her. Inch by inch her crying moans of pain and pleasure got louder and more intense. The dildo didn't want to go in easily anymore. I looked down and saw that there was probably another four inches left of the dildo before the wide suction cup base.

I gripped the suction cup and pulled out, then shoved it back in. I began to fuck her with the enormous toy. I fucked her fast and tried to go deeper than I was before. I succeeded in gaining an extra inch, but still had a few inches that wouldn't budge. By now the tears stopped flowing and her screams and sobs were nothing but pleasurable moans. With one final thrust, I forced the toy in to the base. As I watched her poor abused asshole forcefully stretch to accommodate the width and depth of the dildo (that was probably considered a torture device in some countries), she erupted into a bone chilling scream of pain. She curled up, trying to fight the restraints, and began to shake and cry. It looked like she was pissing herself.

I thought I had gone too far, she never gave me a safe word. I was ready to remove the restraints and apologize when I noticed the look of bliss on her face underneath the tears. She was still spasming and I realized what happened. She really was loving this. She just came, and it was intense. The final thrust of the toy may have been legitimately painful, but that's what she wanted and it made her cum and squirt. I hadn't cum yet, so I was ready to finish. I reached down and grabbed the suction cup base of the dildo and ripped the dildo out like I was pulling my hand out of a fire. She gasped as the dildo plopped out. Her asshole was now a gaping black hole. Or rather pink hole.

I could see directly into her asshole. Suddenly she grunted and I saw the cavern in her asshole begin to get smaller. She groaned and pushed again. She didn't full-on prolapse, but she pushed out a nice little rosebud. I positioned my head in the center of her rosebud and inserted. If you've never fucked a rosebud before, it's amazing. Her asshole may have been loose and gaping, but the soft warm wetness of her rosebud drove me wild. I fucked her harder and faster and deeper until the buildup was too much to take. I exploded inside of her. I throbbed and pulsed inside of her until my cum was forced out of her, past my cock, and made a mess on my balls and her pussy.

I pulled out and gripped my cock by the base and stroked upward once. My hand was now covered in cum. I reached between her legs with the same hand and scooped as much cum as I could from between her legs. She knew what I wanted without being instructed. She pushed the cum out of her asshole and into my waiting hand. After she had nothing left to give, i rolled her over with my clean hand, forced her mouth open, and fed her my cum.

"I want my hand clean, whore. And I want it clean now." She obeyed. She slurped and licked and sucked until my hand was free of my mess. She pulled her face away from my hand, she licked her lips and swallowed, but she still had some on her lips and cheeks that she couldn't reach with her hands tied up.

"Did I do good?" She asked, "is your hand clean enough?" She looked at me, trying to look scared, but she couldn't pretend anymore. She loved it and she was too turned on to act like she didn't want this.