A Real Pain in the Ass

Jenny and I have been together for a year now. Ever since our relationship got sexual, Jenny has been quite the tease about her ass. Hell, I have even begged her for that sweet round ass of hers. She just giggles at me. Many times I've tried to "accidentally" enter her backside, only to have her say "Hey, wrong hole, buddy" or "That's exit only!" I would always apologize and say it was an accident. Bullshit, it was no damn accident, I wanted that ass!

Jenny was 5'7", 22 in age, and about 110 pounds. She has long brown hair and brown eyes. Her breasts are small and perky.

Then there's Jenny's ass. She has a perfect bubble butt. She tans in the summer but never tans her ass. It is so soft and white. I love to smack that ass while taking her on all fours to make it bright red. Jenny has a virgin ass, no one has ever been within her pink asshole. She thinks she's cute when she teases me with it. I don't think it's so cute. Whenever she is naked or in a swimsuit she always finds something in front of me to pick up. When she stands back up she looks at me and giggles.

Yesterday she giggled and said, "You're never going to get this," and patted her ass.

That was the last straw! I thought to myself, 'I will have that ass!'

A smile came across my face as I came up with my plan for her ass.

It was a Friday night. I asked Jenny if we could stay home instead of going out. She wanted to know why so I said I was tired. I told her if we stayed home I would make her favorite drink.

Her eyes lit up when she said, "Mudslides?!"

I told her I would make her as many as she wanted.

Jenny was all for staying home. Jenny doesn't get drunk too often but I do know she loves mudslides.

That night she got smashed. This was going to be easy.

I started to fool around with her and she got all hot and excited. We went into the bedroom where we quickly got naked. My hands caressed her breasts, my tongue played with hers in a passionate kiss. I brought my right hand down to her pussy and began to stroke her clit. She moaned with pleasure. Her pussy was hot and wet. I could see it in her eyes she wanted me inside of her.

I laid her face down on the bed. Jenny liked her sex a little rough and she liked to be restrained. I got out our handcuffs and secured her hands to the frame of the bed. She giggled.

I told her to get on all fours. She did as she was told. I put some pillows under her belly and hips and told her to lay back down. Jenny again did as she was told.

Now I brought out some new restraints. Leg restraints. I restrained both of her legs to the bottom of the bed frame.

Jenny said, "Oh, those are new."

I said, "Yes, they are. I just bought them today." I laughed.

Jenny said, "You are such a bad boy, aren't you?"

I said, "You have no idea."

Jenny's arms and legs were secured to the bed. The pillows underneath her made her ass arch up in the air.

Jenny sighed, "Take me."

I smiled and thought to myself, 'Yes, I will.'

First, I slipped my hard cock into her pussy.

Jenny moaned, "That's it, take me."

I slowly moved in and out of her tight little cunt. I grabbed her hips from the back and put all of my weight into pounding her sweet pussy.

Jenny cried out, "That's it, fuck me good! Just like that!"

Her moans were getting louder as her orgasm got closer.

I could feel her pussy tighten around my cock, trying to milk the cum from my balls. I pounded deep into her, harder and harder. Jenny's pussy was so wet you could hear a kind of splat noise as I rammed my cock into her cunt. She was almost there.

That's when I forced my cock way up into her pussy and held it there. Jenny screamed, "Oh, God!" as she came. Her body was trembling as her orgasm took control of her. She pulled on the restraints as she shook.

While she was coming, I reached under the matress and pulled out some K Y Jelly. I smeared it all over the crack of her ass and on her pretty pink asshole. While I was rubbing it in, I was telling her what a good girl she was and how beautiful she was when she came. She never even noticed what I did to her poor ass.

Jenny finally collapsed when her orgasm was done working its way through her.

I lubed my cock with the K Y Jelly and smiled, thinking, 'Now it's my turn.'

I said to Jenny, "Do you remember all of those times you teased me with your baby butt? You know how you would giggle at me and say you are never going to get this?" I cracked her ass and she cried out with pain.

Jenny replied, "So what?"

I smiled and said, "Tonight you're not leaving this bed with that virgin ass, baby doll."

I cracked her on the ass again, harder this time.

Jenny screamed, "Ouch, that hurt, asshole!"

She tried to get out of her restraints but found she could not get free. I rubbed my hand over her bright red ass.

I asked her, "Are you scared, Jenny?"

She laughed and said, "I don't think so, bad boy. Once I tighten my ass cheeks, you'll never get in there."

That's when I laughed and replied, "You're right, Jenny, but while you came I lubed your ass up with K Y Jelly and my cock is lubed too. It may be a tight fit but I will know your ass tonight."

Jenny panicked. "You fucker, let me go! I mean it, let me go!"

I grabbed her hair and pulled her head back and slipped my cock into her virgin asshole. Jenny cried out in pain. God, her asshole was so tight and warm. She was a perfect piece of ass. I began to ride her slowly.

She began to cry tears of pain. Jenny begged, "Please pull it out! It hurts, it hurts so bad!"

I told her to relax her ass and it would get better. Then I just said, "Shhh," as I continued my ride.

Jenny gave off soft cries and moans of pain as I slowly continued to pop her cherry asshole. I reached underneath and began to stroke her clit. I wanted her to relax and also get pleasure for the pleasure she was giving me.

It worked. Her cries of pain turned slowly into moans of pleasure. I began to pump harder into her tight asshole. Jenny didn't seem to mind. In fact, she relaxed her ass and gave into her pain and pleasure. I stopped stroking her clit and grabbed her hips and told her I was really going to pound my meat into her violated asshole.

Jenny surprised me by saying, "Do it, do it hard!"

I slammed into her ass over and over. Jenny cried with pleasure and pain. I began to pull out of her and then ram it back inside of her.

She cried, "Hurt me! Hurt me so good!"

I looked down at where my cock was passing in and out of her ass. There was a little blood. That made me fuck her even harder. I really put all of my weight behind every thrust into her ass.

I told her I broke the cherry in her ass and could see the blood.

She arched her head back and screamed, "Make me bleed! Oh, God, make me bleed!"

She sounded like she was out of control, like an animal in heat.

I grabbed her hair and pulled her head back and said, "Tell me to cream your cheeks, bitch!" I could feel the cum building inside my balls. I screamed, "Say it , bitch! Say cream my cheeks!"

Jenny moaned then cried out, "Cream my cheeks! Do it, fill my cheeks with cum."

I grabbed onto her hips and thrust deep in her ass. I pumped my cum way up her tender, stretched out, baby ass. When I came, I told her what a sweet ass she was and how much I loved her. I don't think she heard me because she was coming too. Her ass was moving up and down and her whole body shook.

All she could say was, "Oh, oh, oh, " over and over until her orgasm passed.

I pulled out of her abused asshole and spread her ass wide open. My cum dripped out of her bright red asshole along with some of her blood.

I released her hands and legs and asked her how she felt. Jenny must have passed out after her orgasm so I turned off the light and cuddled up next to her and fell asleep.

The next morning I was up early. I was a very happy man. I was sitting at the dining room table having a bowl of cereal when Jenny came down.

She looked like a pouting little girl and just stared at me. I smiled at her. She sat down at the other end of the table.

When she sat down she cried out, "Ouch!" She grimaced in pain.

It took all I had not to laugh.

Jenny looked at me and said, "Ha, ha, funny man."

I laughed and asked her if she still loved me.

She walked down to where I was, cupped my face in her hands and said, "Of course I still love you." She kissed me on the lips, smiled, and said, "But why do you always have to be such a pain in the ass?"

The End

BMR