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At maybe 4 am one Saturday morning I got a knock on my suites door, I had just gotten back from going out and was not tired yet. Opening the door, I found Jess waiting in what were obviously clothes she had been out in that night. I remember a black pencil skirt and heels were the highlights. I knew exactly what she wanted, and invited her in. As she entered I noticed she was limping slightly, and thought it was probably the heels. Another thing I immediately noticed was instead of jumping into bed like normal she sat gingerly resting against the edge of my mattress. I asked if she was hurt or something, and then she blurt out the truth.
At the party she had been at, a boy she didn't know had somehow convinced her drunkenly to try anal with him. It was her first time ever with no experience. Up until that point she had not even let me slip a pinky inside her there when we slept together. She said he was very small and gentle with her, but still she had barely been able to walk across campus to see me after.
She knew how badly I had wanted that part of her virginity, and was not surprised when I was angry about missing out. She promised I could have her ass soon and fuck her any way I wanted to make up for it, but it wasn't enough for me. I demanded the one thing that I wanted most and what she was most afraid of. I demanded to fuck her ass right then, the second guy to do it that night.
I knew she was nervous about my size and her obvious soreness, but as she slid her skirt around her hips and bent over my bed I paid that no mind. She pleaded with me to go slow, so I spread her cheeks and dropped my face into her ass crack. Her butthole was very pink and red but still incredibly tight. I tasted the condom from earlier as my tongue tried to push it's way inside her, but she was too tight so I had to settle for slow deliberate circles around her tiny opening.
I pulled my face away and coated my dick with spit. I knew she wouldn't ask me to wear a condom, she never did. I could see her quivering and her pussy absolutely soaked, Jess needed to be fucked hard.
"I know you're mad, but can you please go easy? I don't know what I'm going to be able to fit tonight" I appreciated her worry but I was jealous she had given herself to someone else before me, "No." I replied, "if I can't be your first, I'm going to be the first to fuck your ass properly. You will take all of me."
I have never felt someone squirm like she did as my thick tip pressed harder and harder against her inflamed and tightly sealed ass. She threw her face down into the pillows to muffle screams and sobs as I worked myself into her. It took lots of spit and moans, but finally I felt myself pop past her barrier and into the tightest thing I have ever felt.
As I promised her, I wasn't kind. Immediately I shoved as hard and deep as I could, roughly grabbing Jess by both shoulders to throw her deeper and harder onto my cock. As I reached my deepest point, Jess let out the most sexual, guttural noise I have ever heard. A mix between a groan, shriek, and a sob this noise let me know she could take absolutely nothing more of me inside her.
I pounded her ass for almost 10 minutes without stop. I pushed her head down, pulled her hair back as I fucked her, and spanked her hard enough to leave raised handprints. I was unforgiving, her wails and groans of pain-filled pleasure only made me want to fuck her more brutally. I could tell something was building inside her, but she was so tight I was almost close to cumming myself. She whispered she was close to finishing, just to keep going. I knew it was too late for me though, even though she was so close I blew my load. I shoved to my deepest and exploded inside her, only to feel her hands reach back to grab me. "Keep fucking me... I'm gonna cum" she begged. So I did. Still hard, I continued slamming her cum filled ass. Within a minute she was shaking and clawing at me, cumming all over. When I rammed as deep as possible during the height of her climax, she gushed. With my thick cum and dick filling her ass, Jess came and squirted all over both of us. It ran down our legs and pooled on the floor. We laughed and collapsed panting. Slowly I inched my dick out of her throbbing asshole. As my tip slipped out I got to watch her hole pulse and quiver as my cum leaked out. Gaping about three quarters of an inch open, she slowly returned to normal size. I slid a finger inside and scooped out a bit of my dirty cum for her to eat. As I watched her lick my fingers clean I knew I would be back inside her again soon.
- 23.02.2022
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