My True Story

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My third anal adventure.
1.6k words
4.12
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Derek kissed my lips softly and tenderly. His nude body loomed over my own as I laid on my back on the bed. My firm 34B tits were being cupped in his hands. He squeezed softly at first then became much rougher as the seconds went on. I stared into his bright blue eyes as his teeth made their way to the soft pale flesh of my nape. He brushed some of my red hair aside to get a better grip on my neck's skin. I moaned and twisted in pleasure.

He leaned up, his rock hard seven inch cock pushing against my already damp pussy. My eyes admired his arms and his six pack abs. His body covered in tattoos; a major turn on. My body only slightly covered but enough to get him turned on as well. His eyes traced my body as he grabbed his cock in his hand. He pushed the head of his dick against the lips of my pussy. My teeth sunk down into my lower lip in anticipation.

"Tell me you want it." He said with a glare. His voice stern and masculine. I smirked at him, pinching my own erect nipples.

"Please, daddy." I said in a whisper. My eyes taunted him with a flirtatious stare.

Derek smirked at my respond. It was exactly what he was wanting to hear. He pushed the head of his dick in but pulled it out. Oh he knew how much I love being teased.

My hips thrusted upward, trying to encourage him to slide more in. He didn't give in so easily though. He rubbed the head of his smooth cock over my clit. My eyes closed and I moaned.

"You like that, don't you?" He sneered.

My head nodded as I let out another pleasurable moan as he thrusted a few inches of his cock inside of me. My mouth dropped opened and my eyes opened. My hazel eyes staring into his own blues. Another moan came forth as he slid even more in. He went slowly, teasing me still, making me crave his cock.

Finally I had enough of the slow and tedious thrusts. My hands pressed hard on his lower back, forcing him inside of me. This time I let out a much louder and longer moan. MY eyes closed and my body tensed as I felt all seven inches of his cock slide inside of me.

Derek did not take long to thrust hard and fast. As I began to scream he placed a hand over my mouth to shut me up. It hardly worked and I moaned and screamed into his palm. This only turned him on more and his thrusting became much more rough. His other hand reached for my throat. He held me down tightly, forcing himself deep inside of my now soaked pussy. I felt his cock stretching me open and I screamed, wanting more and more. I could feel his balls slapping between my legs.

I thought this would be it. I figured he would cum in this rough missionary position, but I was wrong. So, so, wrong. Not that I minded when he slid out of me and tossed me onto my hands and knees. He slapped my ass and sent me lurching forward. I put a hand out so I wouldn't hit the wall in front of me. I looked back at him and sneered. Pushing my ass higher into the air and putting my face sideways on the pillow, I waved my ass side to side. Now I was taunting him.

Derek's fingers slid inside of my drenched pussy. He rubbed my swollen clit for only a brief moment to tease me before rubbing my own juices on my asshole. I knew exactly where this was going. Having only had anal sex twice before my body tensed up. He could sense it as he rubbed more of my juices on my back door.

"Calm down, baby." He cooed as he slid an index finger inside. My asshole was tight and the feeling of his finger only caused discomfort. He watched my eyes clench shut and my mouth too.

"Relax." He whispered again.

With a gulp I took a deep breath and exhaled slowly. I knew the trick to anal not hurting was to relax and I did my best. Red locks of hair stuck to the back of my neck from sweat and my hazel eyes stared up at the powerful man behind me.

He rubbed the head of cock against my asshole. He pressed very, very slowly. I felt my asshole being stretched wide and it was a feeling of pain and discomfort. I let out a whimper of pain and clenched my eyes shut. My teeth gritted together as he went inch by inch inside of me. I couldn't help but to whimper and gasp as I felt my back hole being stretched wide by his rock hard cock.

"Oh yeah, baby. I'm in." He said between heavy breaths.

I couldn't bear to open my eyes quite yet. The discomfort of his cock inside of my ass hadn't gone away. Especially when his hands squeezed my hips and he began to thrust in and out. I felt him slide out a few inches and then back in. His breathing was heavy from excitement. I tried not to squirm as I felt the cock stretching by back end wide open. Four inches out, four inches in. He repeated the motion slow but began to go faster and faster.

"Ah!" I screamed out as his thrusts became rough. He beat into it with no remorse. My body rocked back and forth and he grabbed my hips tightly, forcing me to eat his cock up with my now burning asshole.

"Oh, yeah. Oh, baby. You like that don't you, slut?" He asked between heavy breaths and groans of pleasure.

"Oh." I managed to moan. "Y-yes."

Tears formed in my eyes as my asshole became red. The burning feeling didn't seem like it would go away. Then suddenly I noticed him slow down and pull out. I was surprised for I hadn't thought he came yet. Nope. Different position. I should of known.

Derek sat down, his back against the wall, and patted his lap. I thought he wanted me to ride his cock with my pussy which craved his cock. But as I got on top of him he pulled me forward, closer to him, and slowly set my asshole above his cock's swollen head.

Closing my eyes and with a loud scream "ah" he pushed me down. Once more my asshole was forced to eat his entire rock hard cock. He held my hips again and lifted me up and down.

"Come on baby. Ride it." He groaned.

Wanting to please my man I did just that. My knees rested on either side of him and my hands pressed into the wall above his head. I forced myself up and down, my asshole burning still as it remained stretched by his cock. I gasped and screamed as tears dripped down my cheeks. I felt like I was being ripped apart as he forced me down harder than I had planned.

His hands reached up and his thumb and index fingers grabbed my nipples. He pinched them so hard I had to scream. Using my nipples to control me, he lifted me up and down. I followed his motions, wanting him to cum now!

"Oh daddy!" I screamed after a long moan of discomfort. My eyes were closed but the tears managed to continue to fall down my cheeks. I was panting, trying to ignore the pain in my back end.

"You're gonna cum first." He groaned.

One of his hands reached up to grab my throat. He kept moving me up and down and I followed. My hips moving in circles as well. His other hand went between my legs and in between us. His index finger found my swollen clit and relentlessly he rubbed. His finger moved fast and pressed hard into my clit.

"Ah! Oh! Oh, yes! D-d-daddy!" I screamed. My mouth dropped open to breathe easier and my eyes opened. I stared up at the ceiling as I continued to hump up and down on his thick seven inch cock. The burning in my asshole began to fade as my pussy got the pleasure it craved.

Next he shoved his index and middle finger inside of me. I moaned loud. Without realizing it I began to ride his cock even harder. I screamed loud as I felt that cock stretch my asshole even more. I moved up and down, enjoying the pain mixed with the pleasure. And to make matters better his thumb continued to massage my clit fast and hard. It wouldn't be long till I reached my climax.

Another three minutes of pain and pleasure mixed anal sex, I felt my legs tightening. I closed my eyes and moaned loud and long. My body began to shake, my legs twitching, my thighs tight. My pussy began to pulse around his fingers as my juices leaked onto them. I couldn't help but to sit down hard on his cock. I felt it slide deep up inside of me and let out another scream. Just as I did I felt Derek tense up too. His body also needed release. I could feel his cock stiffen and he wrapped his arms around my waist, letting his load shoot up inside of my back door.

We held each other for a moment, panting and completely pleased. My body still shook slightly from the pleasure of the orgasm.

"I love you." He said, pulling away to kiss my lips softly.

"I love you too." I panted. I began to rise, feeling his cock slip out inch my inch. Somehow, I had a feeling I'd be craving that cock in my asshole more often...

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SmilingBob1SmilingBob1over 10 years ago
Awesome true story

That was a hot story. And as for the anonymous critic, I think he's just mad cause thats how big his tits are. He's thinkin, "How can I get aroused thinking about a female with my sized tits."

LeezyLeezyover 10 years ago
Good hot story.

But why the pain? My experience is that even with 7 inches, once it is in you there is no pain or even discomfort. And there is nothing more erotic than feeling your guy shoot his load up your ass. Some readers might be turned on by pain, but I just enjoy being fucked in the asshole.

AnonymousAnonymousover 11 years ago
Excellent story.

For the critic(s) in the bunch - I'm pretty sure the title is "My True Story," not "A Story Where My Breasts Are The Size My Boyfriend Wants Them," or "A Story That Has Been Changed to Make it Hotter." (Fiesty, I am not implying your bf doesn't like your breasts, just illustrating a point!)

Sure, she could have changed some of the story, maybe spiced it up for you, but that's not what MOST regular readers on here would be expecting based on the title.

Keep up the good work. Try writing a fantasy and see how it differs for you.

kdre373kdre373about 12 years ago
HAHAHA

I am glad you have come over to the "Dark Side". I love the way you relayed a true event. Can we have more?.

BarbaraBarbaraabout 12 years ago
Agree with older-male reader comments! Writer has unrealistic 'anal-entry' expectations. Voted accordingly!

Sadomasochist encounters have a place, but not under "Third time around" 'Anal-sex' descriptions! Get yourselves an inflatable dildo, then wear that stark naked 24/7, until your male lover removes it?

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