Ruin Me, Gently

“Arrrrghhhhhhh!” I hissed in pain, filled with so much pleasure when he tried to add an extra finger. I’ve done silly stuff, but never gone past two fingers. Besides, two of my fingers were roughly one of Don’s.

My breath hitched when he started moving his digits in and out of me. He must have noticed the little discomfort on my face, hence the slow but erotic movements.

I swallowed painfully at the thought of his dick being in me. Don was so fucking huge. Would I even be able to walk after that?

“You are already thinking ahead, aren’t you?” His voice, filled with desire, sent chills down my spine. I’ve hardly said a word since he began to touch me. The truth was that I had no idea what to say! For someone who had given him nothing but a tough time all night, this was too good to let go of.

O ye hypocrite!

“Look how wet you are for me!” He said, slowly increasing his pace. “And tight!!” He kissed my nipple.

I let out a loud moan and at the same time, tried to push back the tears in my eyes. My legs began to get gelly, but before they could give up, Don withdrew his fingers from me and went ahead to undress me. Then he lifted me in a bridal style and began taking deeper steps into his penthouse, with his eyes not leaving my face as I caught my breath. I wondered how he didn’t trip all through.

Would it be strange if I confessed that this felt so wrong, yet right at the same time? I felt warmth! Perhaps it was because of the way he held me possessively. Or maybe the drinks I had were starting to kick in.

We finally got into the bedroom, and he pushed me against the bed. I landed on my back against the bouncy foam.

Don’s eyes didn’t leave mine as he began to undress. I had no idea when I started playing with my nipple at the sight of his cock.

We were under the light so I could see well. I definitely underestimated what I saw at the club earlier. I could see some words tattooed just right above his pelvis.

How the hell was he able to bear the pain? Normal people have tattoos on their arms and chest, but I couldn’t see an……

I shivered when I felt those familiar hands on me. Shawn was already on the bed. He parted my legs, and I saw him slowly bury his face in…

Wait, is he……….. “Holy shittttttt!” I threw my head back against the pillow the moment I felt his lips on my coochie.

I dug my fingers into the sheets for some sort of support, trying so hard to stifle my moans at the same time.

The last thing I expected was for a stranger whom I refused to suck, to eat me up real good.

Don pulled away and positioned himself between my legs. He wasn’t the only one whose eyes were filled with desires. It was more than obvious that we wanted to be in each other’s bodies so bad.

“Ohhhhh Goddddddddddddd!” I couldn’t help the loud moan that escaped me the moment he began drawing circles over my clit with the tip of his cock. Don smacked his fat length on the face of my pussy, and I began to squirm under him.

“You’re scared you’re going to break me?!” Don would have missed what I said if he weren’t paying attention.

I don’t know what made me say this, but I was tired of him teasing me. It was as though I gave the consent he was finally waiting for. My legs vibrated as he slowly pushed himself inside of me.

I reached for the pillow beside me and covered my face with it. Don still went in slowly, obviously trying to fit himself inside of me, but all I felt was intense pain. It was as though I was being ripped apart.

I was almost telling him to stop when I remembered Harry’s words. But why did this fucking hurt so much?

The pain eventually subsided and was instantly replaced with pleasure that made me almost go insane. The pillow fell off my face, and my loud moans instantly filled the room. This felt even better than my fantasies.

Don brought his finger to my wet clit and began to rub in circles as he continued to thrust hard and fast in me. My eyes rolled to the back of my head. At this point, I thought I was going to pass out from so much pleasure.

After all the tears that I had shed today, there was definitely no better way to end the night.

It was a norm to be exhausted after sex or fantasies, but it was hard to uphold that notion right now. It was almost as though this petty stranger and I couldn’t get enough of each other. He flipped me over, positioned me on my knees in a doggy position, slapped my ass, then entered me from behind while pulling my hair. He was rough, yet so tender and intentional, making me yearn for more. Fresh tears kept welling up in my eyes at intervals. This was just too good to take in.

Don subsequently picked me up from the bed. He threw me against the couch on the opposite side of the bed like a sack of potatoes. I landed on my back, trying to catch my breath.

He spread my legs and climbed on top of me. I could still see the lust and desire in his eyes. The thought of him being eager to eat me up sent shivers down my spine. No one had ever looked at me that way.

Don leaned over and began to tease my entrance with the tip of his length.

“Please!!!!!!!” I moaned

“Say it.” His eyes didn’t leave mine as he continued to tease me down there.

I swallowed painfully.

“I’m waiting.” His deep voice came through in a low tone.

I spent the next few seconds returning his deep stare while deciding between speaking my mind and preserving my dignity.

He would probably not remember anything said once this was over, right?

“Fuck me! Ruin me!!”