So this happened my first year as a Teaching Assistant in University. We were hanging out in the lounge of the Grad Student dorm and there were several girls I knew and sort of knew. We were about halfway through a box of cheap wine and the conversation turned sexual as they often do when you have a bunch of tipsy girls in their twenties. The topic came up about butt stuff and I admitted I had done anal and enjoyed it. One of the other TA’s snorted and said something like “No surprise there.”
Now for some background I am Pansexual and though my preference leans toward women, I do enjoy a tall, fit guy with a nice cock who can toss me around a bit. Plus guys are easy as long as you follow the 3 Fs. Flatter them, feed them and fuck them and they are happy as can be. The girl in question was almost the opposite of me. We will call her Brittany (because she looks like a Brittany) a willowy blonde, tanned with brown eyes, slim build and an epic case of resting bitch face. She was taking her Masters in English Lit and pretentious as fuck as most EL Grad students are. I on the other hand am on the shorter side, 5’5” with dark, wavy hair, blue eyes and am a 34C with a runners ass and very pale skin. I took another sip of my wine and asked her what she meant by that.
She blinked and stammered something about how I was more experienced than her and that wasn’t a bad thing but I had likely tried things she hadn’t. I nodded and acted like I let it go but in my head I resolved to fuck her boyfriend. I am not proud of this but she just rubbed me so wrong and was such a judgmental bitch that I couldn’t help it. I knew her boyfriend slightly. He was another grad student doing his Masters in European history, dark hair and eyes, slim but not skinny and about 6’2” or so. We will call him Jack. We followed each other on insta so on the Thursday when I knew Brittany would be out of town, visiting his parents for the weekend, I shot him a DM asking him if he knew about this exhibit of medieval weapons at the museum. He replied that he did and was excited to check it out. I was pretty shameless and asked if he would take me on Saturday because I knew he was an expert and it would be so much more interesting with him as a guide. He agreed immediately. F number one accomplished.
Saturday morning I took my time in the shower, giving myself a very thorough clean, shaving everything silky smooth and an enema to make sure that everything was tidy. It may sound gross but the last thing you want after anal is to see a bit of last night’s pizza on his dick. I wore a blue lightweight dress that showed just enough cleavage and thigh to be noticed but not obviously slutty. I also inserted a plug to make sure I was ready. A small bottle of lube in the purse and I was fully prepared. Ninety minutes later I met him in front of the museum and his eyes were slightly wide. I had spent quality time on my makeup with mascara that made my blue eyes pop and dark red lipstick. I hugged him and grabbed his hand, thanking him for agreeing to be my guide and we went inside. We walked through the exhibit, him explaining things to me and me wide eyed and impressed with his knowledge. F number one ladies. It works wonders. I also made sure to make bodily contact when I could, pressing my tits into his arm when he was showing me something or touching him when he made a joke and laughing. By the time we were done he was putty in my hands.
It was only mid afternoon so I asked if he wanted to grab a coffee or something and he said sure. “Are there any good cafes around you place,” I asked. “The cafes on campus aren’t very good.” I couldn’t risk taking him to the dorm and he may have backed out if I did because one of Brittany’s friends might spot us. He said he did and since he only lived a few blocks away we walked over, me gushing over his expertise and his ego swelling by the second. We got to the cafe and I said I had changed my mind and maybe he had some wine we could have at his place. I squeezed his forearm and it was glaringly clear what I was offering. He rubbed his chin and looked at me and made his decision.
“Sure,” he said. “Let’s go.” We walked to his apartment building and once we were inside his place I was all over him, kissing him and pressing myself into him. He took me by surprise at this point. Knowing what I did of Brittany, I had assumed he would be gentle and vanilla but that was not the case. He dragged me into his living room and pushed me to my knees. “This is what you want isn’t it? To be a good slut and show me how much you love a good cock.” Well he wasn’t entirely wrong and that made it easy. I unzipped him and saw a very nice cock, about 6.5 inches of so but it was also very thick which sent a twinge to my stomach. I was second guessing my decision to let him fuck my ass but he grabbed my hair and shoved himself into my face so I figured that was a bridge we would cross when we got there.
I took him in my hand, determined to do my best and spat on his head and shaft before sucking and licking his balls. He tasted good thankfully and he groaned loudly as I stroked him and bathed his balls with my tongue. I then took him fully into my mouth and to my surprise I could only get about half of him in my mouth. The thickness was just a little too much to get all the way down. He didn’t seem to mind though and fucked my mouth and the apartment was filled with the filthy noises of me trying to take him deep. “That’s a good slut,” he growled and I realized that Brittany may be a little less vanilla than I thought. This wasn’t a guy who gently made love on white lined sheets with Seal playing in the background. I was soaking wet and drooling all over his cock. I knew my mascara was a wreck because my eyes were watering and it turned me on even more knowing what a whore I must look like.
He pulled himself free and rubbed his spit soaked cock all over my face and then stood me up and bent me over the couch. He got behind me and dropped to his knees, pulling my dress up over my hips and then he stopped. Dead silence. I wasn’t wearing any panties and the blue jewel of my plug must be staring him straight in the face. He didn’t say a word but grabbed my ass cheeks roughly before burying his face in my pussy. I cried out as he dragged his tongue along my soaked slit and then started sucking on my labia and probing my entrance with his tongue. I was running like a tap at this point and then I felt him start tugging on my plug, pulling on it until it started to crest and then pushing it back in. I was whimpering now and he smacked my ass hard. “You are such a dirty slut,” he said in a guttural voice that made my knees quake.
He got to his feet and then I felt the head of his cock pushing against my pussy. He slowly pushed in and the combination of his thick cock and the plug filling me made me see stars. The pressure was intense but it felt so fucking good. He reached under me and started to rub my clit as his cock started to pump inside of me and I am ashamed to say I was cumming almost instantly. I grabbed the back of the couch pressing into my abdomen to keep my balance and he fucked me hard. Like, very hard. I was non verbal at this point, moans and grunts all I could manage and then he stopped and pulled out. “Where do you want my cock?”
“In me,” I managed in a voice that sounded half drunk. He smacked my ass hard.
“Where inside of you?” His voice was low and sent shivers down my spine.
“Fuck my ass Daddy,” I replied and he smacked me again.
“What was that?”
“Please fuck my ass Daddy. Please.” I begged him.
He reached down and started pulling out the plug. I was stretching wide and gave a gasp and then it popped out. I closed my eyes and tried to breathe slow and steady and then I felt his cock head pressing into me. I was going to tell him to grab my purse and lube up but the combination of wearing the plug and my juices soaking his cock allowed for pretty easy entry. He slid in and I gasped again, the fullness of it making me groan. He started fucking my ass, slow and steady and I reached down to rub my clit. His hands were on my hips and the sound of my ass smacking into his thighs filled the room. He was moaning now and telling me what a good three hole whore I was and then I realized I was about to cum again. I rubbed my clit hard and practically screamed as my orgasm ripped through my body, far more intense this time and I think I may have actually blacked out for a second. The spasms of my body must have triggered him as well because suddenly he stiffened and I felt his hot jets of cum painting my insides. He slowly pulled out and I could feel his cum leaking from my ass.
“I need to use your bathroom,” I told his and he just pointed, stuffing his cock back into his pants. I went into the washroom and cleaned up as best I could before I spotted the pink toothbrush in the glass next to the blue one. No, I told myself. Don’t be petty. It didn’t work. I took the tissue covered in cum from my ass and rubbed it all over the bristles and then put it back. I washed my face to remove the racoon look my running mascara had caused and then peed and washed my hands. He was still standing when I came out and smiled at me.
“So I was thinking we could get a pizza or something and watch some Netflix,” he started to say but I just shook my head. I walked up to him and gave him a very sweet kiss and collected my plug and put it in my purse.
“Once for fun but you have a girl friend. Don’t worry, it’s our secret.” I squeezed his hand and left, my ass feeling empty and loose and headed back out onto the street. I jumped on the street car and felt eyes on me as some of the guys checked me out. If only they knew.
Later that night I blocked Jack on insta to make sure he didn’t come mooching for seconds and masturbated twice remembering how full I had felt. Like I said, I am not proud of what I did and if I had it to do over? I’d do the same fucking thing. Fucking bitch.