Ryan's Dilemma free porn video

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Dedicated to my favorite author, Angie E, also known on SOL as Tasty Little Pop Tart

Saturday, February 9, 2019, 1:34 am

This was fucking crazy, he thought. Panting, and trembling with adrenaline/testosterone shock, Ryan looked back over his shoulder and shook his head. He could not believe he’d impaled his bottom on a fucking Dick Rambone dildo. This was just crazy.

It was 1:34 am, according to the alarm clock on his nightstand. He’d turned the clock to face him before offering his asshole to the dildo. The head was inside him, gripped tightly by his disbelieving sphincter. He was the asshole, he thought.

Reaching out, he fumbled the bottle of Heineken, and then swigged a big mouthful. He’d ensconced the bottle in one of his dad’s ridiculous beer bottle sleeves. It kept the bottle surprisingly cold. He downed another big gulp.

He was alone, the condo his until Sunday afternoon. Mom, Dad, Hillary, Olivia, and Hannah had gone to visit Grandma Constance in Columbus. He had a cache of bodacious dope with plenty of papers, and a case of Heineken in the fridge. Mom told him he could drink 3 beers a night and not be in trouble. Ryan was 16 years old. His birthday was two weekends ago.

“This is fucking crazy,” he mouthed. “What kinda 16 year old boy fucks a dildo with his ass?”

A crazy, horny one, he thought.

Though naked and partly mounted to a huge black phallus, Ryan didn’t consider himself queer. He’d never sucked a cock, never had one up his ass, nor kissed a boy. True, he wore his sister’s underwear and outfits on occasion, but what 16-year-old didn’t do that? He watched videos at night of boys getting their butts fucked and gobbling big cocks, but that only meant he made his own path through the woods, rather than follow everyone else. He was independent, not queer.

He’d smoked 2 joints and downed 4 beers. He didn’t care if his mother ragged on his ass on Sunday. He intended to have a really fun weekend.

“Are you okay?” Connor asked.

Ryan sighed. “You sure we’ll get paid for this, dude?”

Connor stopped recording. “He already gave us $1500. He paid for the dildos and both these cameras. He paid for the Heineken we got in the refrigerator, and the ounce of dope on the bed over there.” Both looked at the stash longingly. “He promised $3000 for this video, sight unseen, dude.”

Ryan grumbled something unintelligible.

“He also said we could walk away from this if we wanted to, no broken bones.”

Ryan chuckled disgustedly.

It bothered him having a fierce hard-on with a giant cock in his ass. The idea of sliding back on the huge black shaft until it disappeared completely inside him made his balls ache inside his shriveled scrotum. What possessed him to sign up for this?

Ryan stood 5’7” tall and weighed 125 lbs. He was physically developed from years of playing sports. He was cute, with stylishly shaggy blonde hair, and blue eyes. He’d been naked before Connor only once, only slightly pushing the boundaries of their non-sexual relationship. They beat off together in the afternoon sometimes after school watching porn, and had even stroked each other’s cocks in mutual masturbation. Sometimes they even made each other ejaculate by mutual agreement. On the face of it, neither boy considered this queer behavior. Regardless, events of his birthday colored everything a darker shade of red.

Ryan said: “Has it occurred to you, we aren’t normally adjusted, 16 year old boys, Connor?”

“Whaddya mean?”

Flustered, Ryan gazed at him in irritation. “Dude ... I’m naked. I have a cock up my ass. If I get it all the way inside me, and fuck the damned thing like the guy wants me too, we get to split $3000. If I give you a blowjob while I’m doing it... ?”

Connor winced. “I thought that was out.” He cocked his head. “I thought you said no sex, Ryan.”

“He joked about paying me to fuck a dog, Connor. He joked he’d pay me $10,000 for that privilege.” His face grew red. “It wasn’t entirely a joke, either. Just like me gobbling your cock while I fuck the dildo, wasn’t a joke. Just like his saying I’d look good with your cock up my ass, Connor.” He flinched and cut his eyes away a moment.

“The fact he even suggests stuff like that means he doesn’t see me as a normal 16 year old boy, either.” He shook his head slowly. “I’m only 16 and 14 days old, Connor. I’m not normal. I’m a fucking pervert.”

Connor sat the camera on Ryan’s desk. “I gotta tell you something dude...”

“What?” Ryan said.

“Seeing you like that, even though we talked about this a hundred fucking times...” He unsteadily shook his head. “I don’t think I’m normal, either, Ryan.”

Ryan gazed at him warily. “I’m not sucking your cock, Connor. You can forget that, right now.” He shifted uncomfortably on the huge head in his asshole. He wondered why he kept it in his ass, anyway. It was perverted.

“I didn’t expect it to turn me on like this,” Connor said, “but it does.”

The guy with the money and a penchant for 16-year-old’s had contacted Connor a month ago. Connor was 2 months older than Ryan, and was instructed not to engage Ryan in the scheme until he turned 16. That happened on Saturday afternoon, January 26th, two weeks ago.

“Dude, we gotta talk,” Connor had said.

Ryan was intent on disabling a maneuvering Iranian tank. “About what?” he said.

“Someone hacked your computer, dude.”

That got Ryan’s attention. He paused the program, running on his brand new Xbox One.

“What?”

Connor lowered his voice almost to a whisper. “I saw the videos you downloaded of the middle school kids.” He looked unexpectedly disturbed. “Dude, that stuff’s patently illegal. Where did you find it, anyway?”

Ryan was red-faced, scared and embarrassed. He never thought to lie about it, though. Instead, he jolted upright and stumbled across the room to his bedroom door and locked it. Looking back, he gulped loudly and croaked: “What guy are you talking about? When did I get hacked? Why are you looking at shit off my computer for, asshole?”

Connor had expected the flare of rage. “He also showed me the history from your browser, dude...” He grinned salaciously. “Dude, you like seeing boys get fucked and sucking cock an awful lot, don’t you?” He held up his hand. “It’s okay. I’m cool with that stuff. What I don’t understand is your interest in boys and dogs.”

Ryan flushed bright red and looked away. For the past 6 months he’d watched and occasionally downloaded illegal videos of boys and dogs having sex. He’d discovered a series of videos featuring the same twin brothers, his age, having sex with each other, other boys, and numerous big dogs. The twins were blonde, blue-eyed, tall and slender with embarrassingly fetching cocks and delicate testicles. Watching them 69 and take each other up the ass drove him nuts with craving. Many other videos were worse, indescribable on these pages.

“I’m being blackmailed? I got no money!” he protested, panic-stricken. “I’m only 16!” His eyes suddenly bulged, and his complexion turned dangerously sallow. “He’s not blackmailing me for sex, is he?” Fright nearly made him hyperventilate. “Jesus, Connor! What am I gonna do if he wants sex?”

Connor shook his head. “He’s rich and famous and not interested in getting his cover blown.” He held up his hand. “He sent me something to give you.”

“What?”

Connor dug a flash drive from his front pocket. Ryan balked as though it might be a miniaturized nuclear weapon ... or a dog collar he’d wear the rest of his life. He backed against the door, shaking his head.

“It’s nothing to get in a panic over, dude.”

Terrified, Ryan shook his head.

“It’s just some dude riding a really big dildo with his asshole.”

Ryan flinched in embarrassment. He’d watched a series of videos on xHamster exactly like that last weekend. Watching the queer fuck a black dildo 14” long on his hands and knees made him apoplectic. He’d exploded three times watching the videos.

“‘Riding my Rambone,’ “ Connor recited. “The guy said to tell you that. It’s what he wants you to do on video for him. He said he’d pay you to do it, Ryan.”

Ryan gawped, appalled.

“He said he’d pay you do other things too.” He grinned rather sheepishly. “You don’t want to know all the details, believe me.”

Ryan shifted restlessly on his hands and knees. It bothered him so much more to be naked with a humiliating boner in full view of his friend, than being attached to the fat black dildo. “I don’t know how anyone does this,” he complained. “It’s fucking impossible.”

He unwillingly glanced at his friend’s strained crotch. Connor was bigger than him, 7” to Ryan’s 6”, and noticeably thicker. Connor had what Ryan considered an intimidating cock: thickly veined, bruised looking when erect, the head small, lending it a menacing appearance ... designed for rape. Ryan had uncomfortably imagined it in his mouth and rectum many times. His feelings for Connor sometimes scared him.

“Do you want me to suck you, Connor?”

Startled, Connor blinked rapidly and backed a step against the corner of Ryan’s desk. “Do you want to?”

“Do you want me too?”

Connor stared at his friend’s exasperated expression. “Well, yeah ... I’ve always wanted you to, Ryan.” He flushed with embarrassment. “I don’t particularly want to have you do it now, though.” He flushed deeper. “Not when you’re all messed up on weed and alcohol and have a cock up your ass like that.”

“It’s not up my ass!” Ryan complained stridently. “I’m only holding it with my asshole, dammit!”

The ridiculous distinction made both boys blush deeper red.

“How’d we get into this fucking mess?” Ryan complained. “Turn the camera back on and let’s make some money, dude!”

His rectum could not possibly hold the entire dildo. Overall, including the vital suction cup on the end, the phallus measured 16-1/2”. The shaft was 13-1/2” long, and 2-3/8” wide at head and base. His rectum bottomed out at approximately 7” depth (according to Google, anyway), which left 6-1/2” unaccounted for. He knew in order to ride the entire length, the head needed to bull past the 90 degree bend into his sigmoid colon. He knew it could be done; the question was, did $3000 cover the torture involved?

Make that $1500, he reminded himself irritability. Connor got the other half.

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Charlie POV: Shortly after Dad left, Bob and I decided to see if we couldn’t help out some. I noticed TJ over by the main entrance talking to Jim Gregory. I was just heading over there when TJ flashed, “Charlie, you and Bob might want to make yourselves scarce for a little bit. Jim was just asking about you guys, wondering if you guys had anything to do with this. I told him I hadn’t seen you and weren’t sure where you were.” “Why would you do that, TJ? I’ve worked with Jim Gregory a few...

2 years ago
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Martas Unfortunate Dilemmas

Marta Fernandez was a 22 year old, Colombian student who was able, with the help of her father, whose friend worked in the embassy in Bogotá, to get a student visa to study in the U.S. All her life she had dreamed of coming to the U.S. to study English and hopefully meet a nice American gentleman she could fall in love with and marry. The men in Colombia were all the same, a bunch of womanizers who did not know the meaning of commitment. At every opportunity they poked themselves into the...

3 years ago
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Deedi EmergesChapter 7 Deedis Dilemmas

Deedi woke early on Monday eager to get ready for her new job. She wanted to look her best but that was never a problem since she was adept at putting on her make-up and dressing for effect. She wore a grey two piece suit with a light, check pattern. The skirt was knee length with a slightly see-through, light blue blouse and matching blue underwear. She pulled on a pair of sheer, barely-black stockings and clipped them to her suspenders and found a pair of plain, black high heels. The...

4 years ago
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Donnies Dilemma

Donnie Hamilton is the typical annoying teenaged little brother. There was just two years difference in the ages of him and his big sister, Lucy. The immature way he acted, one would think there was much more of an age gap. She tolerated Donnie’s juvenile behavior because she loved him. She learned to put up with his pranks because she understood Donnie was going through puberty and was beginning to have an interest in girls. She also knew he was too young and inexperienced to understand why...

4 years ago
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Tina and the Stuffed Pussy Chapter 7 The Breadstick Dilemma

I sleep in on Sunday, determined not to show up at the Stuffed Pussy earlier than I have to. When I get in I am dreading Eddie’s reaction to my tardiness, expecting the worst. Instead I hear Eddie yelling at someone in the back room. “How could you screw up something as fucking simple as breadsticks! How many fucking breadsticks do you think we can sell… we ain’t a pizza joint!” I hurry in and start cleaning up, relieved that Eddie is too caught up in other problems to notice my late...

4 years ago
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My Dilemma

Thanks to ‘Techsan’ for editing this story. It was the worst of times. It was the best of times. Boy, how many times have I heard that in my lifetime. Came from some book somewhere. Now a lot of the movies like to use that quote. For most people the statement is true. Only for me I seem to be getting more of the worst of times lately. My marriage of twenty-two years is ending in a not-so-good manner. Because of it, I might quit my job on the police force. So here I am at the old watering hole...

3 years ago
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The Family Dilemma

By Docker5000 Denise Parkin was busy in the kitchen as usual preparing everybody’s breakfast. She now had the breakfast ready and she was now calling her family and telling them. “That it was getting cold and for them all to get a move on.” James her husband was the first to walk into the kitchen, he was trying to tie his tie as he walked in to the kitchen. Denise just smiled at him. She now wiped her hands on a towel and she then walked over to him. Denise now smiled at him. He...

3 years ago
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Heathers Dilemma

by Napoleon Leopold Heather Morris had finally made it home from work and was looking forward to the long weekend ahead. She went upstairs and took a warm shower and then proceeded to get ready for the evening. Red lace panties and matching bra made her feel sexy. Red stocking held up by garter straps and 4" high red pumps adorned feet. Opening her dresser drawer heather pulled out a red leather collar with a d-ring set in the front, she lifted her medium brown hair up so she could buckle...

2 years ago
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Little Sisters Dilemma

I always considered myself to be a typical teenager, but looking back, I may have qualified as a bit of a “nerd”, for lack of a better term. I never really had a problem with academics, and as a result, never had to study all that hard, or that much. At the ripe old age of seventeen, and in my last year of high school, I should have had the world by the balls. For the most part, I did, too, except for one small, insignificant detail. I had a sister that was a year younger than I was. Now,...

1 year ago
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Ryans dilemma

This was an unexpected turn of events for a Friday night. I had planned on spending the evening on a wonderful date with my girlfriend. She already knew what the plans were, she never liked surprises. Me being the romantic type, this took a lot of fun out of the relationship for me. We were to begin the evening at a fantastic, and very expensive, restaurant. She had wanted to go ever since her best friend’s boyfriend took her there. I wanted to take her this evening and tell her about the...

4 years ago
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IHNC 65 Lisas Dilemma

(This chapter is from the viewpoint of Lisa Cohan, a schoolmate of Becky’s who joined in her SATs tutoring her High School Math teacher was giving her.) OMG! I wish I could get out of here! No sooner did Mr. Font drop me off than my hag of a Vietnamese mother began yelling at me in her inside voice: Broken English Banshee Wail. “WERE THE FUCK HAVE YOU BE!” “Studying for my SATs,” I tried to calmly respond, but she didn’t care if I was dead and rotting in a dumpster, she just...

2 years ago
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Moms Dilemma

Jolene was at work when the phone call came. Her thirteen year old son, Donny, and three of his friends were due to be driven back home from summer camp by bus. The bus had, apparently, broken down and the camp director was calling her to ask that she drive up and take the boys home herself. It was one thirty and the boys were due to be home by four. The drive to the camp was a four hour round trip. If she left immediately she wouldn’t be there until three thirty and, at best, would have the...

4 years ago
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Two Moms Two Sons 1 Sandras proposal And Londons Dilemma

POV: London"It is good to have you and your son over, Sandra," I mentioned, stirring the pot."We're practically best friends now, and don't forget my hubby, who is currently locked in your bedroom with your husband," she whined, strolling towards me with her arms crossed. "If I didn't know any better, I'd say they were having sex.""Sandra," I said a tone while grinning. "Keep your voice down; Joe and Pete are in just in the living room.""So what, London?" she complained, walking...

MILF
4 years ago
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Kathys Dilemma

Mrs. Kathleen Mary Thomson (Kathy to all who knew her), a trim 39 years young, mother of two girls and a manager at a financial services firm, leaned against the door jamb of the office tea room holding her thermos mug in her right hand whilst using the other to tuck her long, lustrous, flaming red hair back behind her left ear. She could not help but smile at the furtive conversation between the three office juniors, all of them young women, as they casually discussed the merits of the firm’s...

2 years ago
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Danis Dilemma

I watched his plane lift off and disappear into the eastern sky. As I slowly walked across the airport terminal to the parking lot, I tried to compose myself as I wiped the last few tears from my cheeks. I could still feel his lips on my lips and the lingering scent of his shaving soap was still with me, but both sensations were rapidly vanishing. As I climbed into the car, I leaned back one last time saying good-bye to the man I loved. The feeling of the strength of his arms around me in our...

3 years ago
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The Ex Dilemma

The cool breeze of summer washes over you as you walk down the sun-beaten sidewalk of the city. You've always loved living in the urban environment, because everything is so close and you can walk from destination to destination. In fact, that's what you're doing right now. About an hour ago your ex, Anna, called you up for the first time in months; she said it was important and she needed you to come over. Anna had always been a bit cryptic, keeping things to herself, but this time it was...

2 years ago
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Ethical dilemma

AUTHOR'S NOTE: THIS IS A SEQUEL TO "TURNING TEACHER'S PET INTO TEACHER'S SLUT," BUT THIS STORY CAN ACT AS A STAND ALONE IF YOU DONT WANT TO READ IT. ANYONE CAN ADD TO THE STORY, AND I WOULD MORE THAN APPRECIATE ANY COMMENTS OR HELPFUL TIPS. THANK YOU FOR READING, AND I HOPE YOU ENJOY THE STORY. Sarah was happy to finally be in college. It was something she had been looking forward to for a while, and now she was finally here. She had a full ride, thanks to the fact she was valedictorian and her...

Lesbian
2 years ago
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Dishas Dilemma

To Dan, Disha's beauty seemed amplified by her mocha skin and jet black hair. He watched intently as Disha tucked her near transparent white blouse into her black pleated miniskirt. Even now, in her early-twenties, her school uniform fitted like she was a young sixteen. For obvious reasons, Dan always loved his wife wearing this particular outfit. He sat in silence on his chair, feeling himself harden as she sat cross legged on the bed, showing a hint of her white cotton panties. Disha laughed...

4 years ago
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The Dilemma

Two simple straight pink lines said it all. Just in few seconds my worst fear had been confirmed .I knew shit just got real! Its not like , i didn't want a c***d or it was too early to brace motherhood. I was a newly wed and under normal circumstances this would have been expected . But then again my life , since the day i turned into a woman has hardly been normal or called normal. You the pregnancy itself didn't scare me . If you haven't guessed ,so far not knowing who the father is , whose...

3 years ago
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Runners dilemma

Why? I can’t say. I don’t know why. But I what I did and I don’t regret it a bit. I run with a co-ed club. It’s a fun bunch, some fast, some less so. We finished our run and everyone was standing around chatting, stretching and cooling off. And it was hot. Too hot. My shorts and tank top were soaked with perspiration. I tried toweling off to no avail. The idea of getting into my car, literally dripping with sweat, saturating my leather seats, was not appealing.I parked in the far corner of the...

3 years ago
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A mothers dilemma

Joan Simmons was a 48-year-old mother of two, who had been married to John Simmons for the last 22 years. In the beginning they had a wonderful sex life and frequently made love two or three times a night, although over the last five years it had been more like once a week. Joan was not one to complain although she did miss the physical contact from her husband. Both are c***dren were now in their late teens Robert being the oldest at 19 and James Younger by three years. Reasonably comfortably...

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