It started as any other normal time I had with my boyfriend. Ryan and I had been dating for a year and a half before he’d pressured me enough into letting him pop my cherry. We’d made out before that and I’d give him blow jobs. It became a tradition that for every touchdown he scored for our schools football team he’d get to cum in my mouth or on my tittes after the game.
I found out that I really liked sex after the first time. Ryans a lot bigger than me, his penis being nine inches long when erected and I’m just five foot four, slender, with size c breasts. Ryan said he liked my tittys though and sometimes in the middle of the school day we’d sneak off to the football team locker room so he could suck on them while I jacked him off.
Anyway, needless to say our sex life got pretty wild after the first time. One night while my parents were out of town we started to experiment with handcuffs. We took turns cuffing the other to my headboard. He’d eat me out and lick my clitty until I’d cum all over my sheets. Then we traded places and I sucked his enormous cock until the cum spurted into my mouth and dribbled down my chin and onto my boobs.
It was this same night that Ryan asked me the question I’d never expected from him. We were laying on the bed, him on his back and me ontop of him. I was sucking off his cock and I could tell he was looking at my pussy as I did so. His moans were getting louder and louder and I knew Ryan was close to cumming again when I felt his hands squeeze my ass cheeks apart and he lifted his head to tongue my little butthole.
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“Ryan!” I moaned out, gasping in surprise, “What are you doing?”
“What’s wrong Hannah? You know guys like it in the ass, it’s tight there. ” His tongue licked down to my pussy and I moaned and went back to sucking him off. It was hard to concentrate on the sucking while he was kissing and sucking on my little clitty. Pretty soon I’d stopped all together and started to whimper like crazy.
“Oh god! Ryan! You’re going to make me cum! Oh Ryan!” I screamed out as I felt my juices spill all over his face and he started to lap it all up.
“Mmm, baby my cocks still hard for you. Can I put it inside your ass please?”
I sat up to look into his pleading eyes and even though I wanted to try it I was scared that it would hurt too much. “I’m scared. ” I said softly and he sat up and hugged and kissed me.
“Lay down baby, I wanna show you something. ”
I lay down like he told me to and he took my ankles in his hands and spread them wide. At first I was worried he would try to stick his finger or cock inside my ass but instead he leaned down and pressed a warm kiss to my wet pussy opening.
“What are you going to do Ryan?” I asked, my breath growing hot, with each intake my tits heaved up and down.
“Hannah, I’m going to show you just how much you can take. Now trust me alright? It might be uncomfortable at first but it’s going to feel good alright?” He looked down at me with his handsome face and I couldn’t help but smile back at him.
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He’d said that to me before, and when I did it opened up the world of sex to me and I’d be forever grateful to him for it.
I first felt one finger slip inside my warm, wet pussy and I gasped. I always forgot how long his fingers were. The finger reached right for my little pleasure spot and started to rub. I arched my back and gripped the pillow on either side of my head. Soon it was followed by another and I bit my lower lip. I was a little girl, and even just two fingers were a stretch for me, but they wern’t as big as his cock so I knew I could take more.
After pulsing his fingers in and out of me a few times I could feel a third one creeping in and I tensed. “R-ryan!”
“Shhh… it’s okay baby, just relax. ”
I nodded and breathed through my nose, trying to relax as I felt the third finger prodding at my little pussy hole before slipping in to join the others. I was really stretched now and it felt uncomfortable and yet fulfilling at the same time. I looked upinto Ryans face as his three fingers stroked in and out of me, caressing my pussy walls.
“That feels amazing. ” I breathed, “I love you so much Ryan. ”
“We’re not done yet babe.
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”
“What do you mean?”
“You’re going to take it all. ”
“W-What!?” I tried to sit up but he leaned over and began to suck on my tit, making me lean back and moan. The three figners inside me were starting to feel really good and I imagined it was one big cock, fucking me.
“Oh Ryan! Ryan!” I panted, knowing I was closer.
Without warning he shoved the fourth finger in and I screamed, the pain sudden. I reached up to smack his arm since he was grinning at me.
“Bet you never thought I’d be able to get all four inside you. ” He teases before leaning down to lick little circles around my navel. I frowned but layed back down and let him, the painbeginning to subside since I was so wet and he still moved slowly in and out of me.
“You’re an ass. ” I grumbled, but I drew up my knees and parted my thighs even further. I’d never felt so open and yet so filled in my entire life.
For several moments Ryan just finger fucked me with all four fingers inside before he leaned over me and whispered, “You can take more Hannah. I know you can. ”
I opened my eyes and looked up at him.
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I was starting to get really close to cumming and all I could manage was a soft mewing sound. His thumb was starting to prod it’s way into my pussy and I winced everytime it neared my opening, but after a lot of wiggling and pulsing I felt his entire hand slip inside my velvet, warm pussy.
“Holy shit…” Ryan gasped as he looked down at the sight of his entire hand disappearing inside me.
It was all I could do to moan out his name as I came and gripped his hand, feeling it fully inside me. It was amazing, unlike anything I’d ever felt before.
After I’d come, Ryan just looked at me and slowly slipped his hand out one finger at a time. Then he leaned down and kissed me.
“I love you Hannah. ” He whispered and I wrapped my arms around him.
“I love you Ryan. ”
We kissed for a little while longer before Ryan pulled back and grinned at me. “Can I fuck your asshole now?”
I smiled back and nodded.
The End.
.
