Phil's Web Cam Mistake

By moc.loa@1ksoBriS

Published on Jun 18, 2009

Transgender

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Phil and the Web Cam by Sirbosk1 Copyright 2009 SirBosk1

This story is a fantasy that contains scenes of homosexual and heterosexual sex, rimming, dominant males and females, cream pie and other erotic activities involving adults. If such subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now. It was written at the request of a fan, jockobi1.

All persons, names, places, events, and descriptions, are purely fictional. Any resemblance to actual persons, names, places, events, or descriptions, is totally unintentional and a pure coincidence. This work is copyright by the author and commercial use is prohibited without written permission from the author.

Personal/private copies are permitted only if complete, including the copyright notice. The author would appreciate your comments pro and con, including constructive criticism, and suggestions. sirbosk1@aol.com

Phil hurried back to his hotel room. He was a government agent for Internal Revenue and traveled a great deal, doing on site audits of companies. He had a web cam appointment. He couldn't be late!

His wife of one year and ten years his junior, constantly badgered him in the past to get a new assignment so he could spend more time with her. She had complained of being a newlywed that was nearly a virgin after one year. However, lately, she had stopped her complaints and seemed to have accepted his job requirements.

Phil was thankful that she was settling down.

His wife, Ann, was very beautiful and incredibly sexy. Her large blue eyes, upturned nose, high cheek bones, full pouty lips and blonde hair, cut short like a boy's, made her face look like that of an impish elf.

She was petite, five foot tall and one hundred pounds.

Though tiny, she was a former gymnast who had to finally give up her sport as a young teen because of her large breasts. Her bust measurement was not large but measurements are often deceptive. Her 35 inch bust was C sized cups. With her slim build and narrow back, it made her magnificent perky breasts look like they were DD.

She had a 20 inch waist and 34 inch hips which further accentuated her full-breasted look.

Her many years of balance beam and floor exercise had made her fine bubble butt as hard as steel. She bicycled, practiced yoga to stay limber and worked out in the gym, five days a week to keep her magnificent body in perfect condition.

In other words, she was a hot hard body that moved like a snake. Standing still, she was stunning. Moving with the natural grace of a ballet dancer, the athlete that she was, and with the sensuousness of a high priced stripper, she was a wet dream. Most men and many women, stopped in awe when she walked by during her normal day.

She had few female friends and the newly married couple had no married friends since married women feared the sexually incandescent young woman would make them look like crows to their lusting husbands. Men just couldn't help themselves around her. Many were struck dumb when she paid them the least attention.

Ann, used to the admiring gaze of men all of her teen and short adult life, knew the affect she had on men. Every time a man on the street walked into a street sign or some other obvious obstacle while studying her incredible sexual animal movement, she grinned and laughed to herself.

Her power over men gave her confidence and power. She didn't know it but she was a bit sadistic and a natural sexual dominant.

So, what was wrong with Phil? Why didn't he change jobs, quit his job, rob banks, whatever was necessary to spend time with his beautiful and highly sexed wife?

Well, Phil was a closet repressed bisexual and had grown up under the guardianship of his lesbian Aunt. His father, a large muscular elite military man, had died just after he had impregnated Phil's mom. Dad had been on a covert mission in some South American country and mysteriously never returned. The government wouldn't release the details, only saying he had died honorably. His mother, distraught with her new husband's death, took her own life shortly after Phil was born.

His Aunt, now dead as well, was never too happy about being burdened by the requirements of raising a healthy strapping boy and to be frank, had not been fond of boys or men in general. She was strict with Phil, giving him no privacy and little affection. Auntie had the money and time to care for the boy but frankly, knew nothing about raising a boy and had no interest in learning. She raised him as a girl even though he was over six foot and well put together even as a freshman in High School. He learned to pee sitting down, wore cotton panties even in high school and learned perfect manners to keep from feeling Auntie's wide leather belt. The Aunt was content to make sure he was polite, fed, adequately clothed and kept from abusing himself. To the Aunt, that was enough. After all, she had her own pleasures to take care of. She couldn't be bothered with her straight weak sister's brat.

Phil had no male role models while growing up in the rural town with his Aunt. Well, that was true until he was in high school. There he met and fell in thrall with his gym class teacher. Mr. Johnson was much like Phil's dad, at least what he could gather from studying the few pictures of his dad from the family album. The first day of school, Mr. Johnson noticed the shy withdrawn boy right away. Right off, he saw the cotton panties the boy wore and pulled him to the side. He told the boy he would be teased unmercifully if found out, to go to the bathroom, take them off and return them to him.

Every day after that, Phil removed his girly underwear to be stored until the end of the day so he could put them back on for his Aunt. Phil worshiped his protector from that point on. In the end, once Phil was totally spellbound, Mr. Johnson molested poor defenseless Phil. The unhealthy relationship continued through Phil's college life.

All of his adult role models had betrayed the trust Phil had placed in them as authority figures in his life.

A smart boy, Phil had no problem obtaining a degree in accounting followed by an MBA from a good Midwestern college.

Ann had met him after he had given a seminar in tax law at her college. His impeccable manners, well dressed athletic body and shy ways, captured her heart. He was a good-looking man, slender but fit, tall and handsome. He was also obviously successful in his secure government job.

To Ann, he was a catch. He was built like a he-man, dressed like a model, had old world manners and had money.

The dominant and confident Ann set her sights on Phil and he didn't have a chance. To help with his job advancement, Phil needed a wife to keep up appearances and, after inheriting his Aunt's money, was comfortable financially but not well off. Within two months of his meeting Ann, he was helplessly in her power. He couldn't say no.

They were married in a small ceremony attended by Ann's mom and Phil's office mates. Neither of the two newlyweds had any real friends.

It was then that the problems started. Phil, traumatized by all of the child abuse, was sexually repressed by a domineering woman and thought about men due to his experiences with Mr. Johnson while he was intimate with his new wife. Incredibly, her fabulous female body and sensuous grace, made it difficult for Phil to concentrate and perform for his hot wife. She frightened him.

Phil had zero experience with women. His lesbian Aunt hadn't let him date. He had lived at home with his Aunt until he finished college and couldn't even masturbate. His Aunt would beat him mercilessly when she caught him.

He now always associated beatings with pleasure and couldn't get aroused without being dominated.

Even though he had lived alone since his Aunt had passed away eight years ago, his strict training made him feel guilty when he got a hardon. He had learned that icing his package worked well enough to stop the cravings even though it was really uncomfortable.

Outwardly, he was a very masculine well dressed hunk. On the inside, he was a very fucked up repressed scared little boy. He couldn't get sexually hot unless it was with a dominant male or female.

After his near failure on his wedding night, he volunteered for every job that took him away from his super hot sexy wife. He couldn't take the pressure to perform from his demanding sexually liberated wife.

His boss was completely baffled by this behavior but was happy with the outcome since the rest of his staff was very pleased to stay home with their spouses and sexual partners.

Phil had been so happy lately. On a long assignment, he had met a young very dominant masculine man in the hotel gym.

Al had noticed Phil checking him out immediately and asked him what he was looking at.

Embarrassed, Phil shyly and boyishly reverted to the behavior that got him approval in school, very politely begging for forgiveness from the sweating macho man.

Al immediately spotted the submissive nature of this well-built tall handsome man and ordered Phil to go to the bar on the first floor and bring back two beers.

Phil was happy as a puppy having his belly rubbed. He gleefully rushed out and swiftly came back with a tray with two expensive domestic beers, a bowl of nuts and some pretzels.

"Is this beer ok, Sir?" pleaded Phil uncertainly.

"It will do for now, faggot," growled the macho man as he drained half of the bottle.

"Is there anything else I can do for you, Sir?" asked Phil.

"Yeah faggot, pick up my stuff and follow me," Al said as he purposely strode out of the hotel gym to his room, his puppy following happily behind, loaded down with the tray, towels and gym bags.

Once in the room, Al told Phil to come in. "Strip down, boy so I can see what I've got here."

Jumping to Al's commands, like he was Al's slave all of his life, he swiftly peeled his sticky T-shirt, gym shorts and jock, standing in front of Al, in nothing but his running shoes.

"Good, faggot. Turn slowly and pull your ass cheeks apart so I can see what a good little pussy boy you are!" he snapped.

Smiling, Phil did as ordered, spread his legs, pulled his ass cheeks apart and turned around, presenting his firm muscular ass as ordered.

Al was impressed by the handsome fit older man's polite obedience. This submissive man could be a real find!

"OK boy, turn around again," throwing him a bottle of hand lotion. "Get that little pricklet hard for me, boy."

Phil, obeying happily, applied some of the slippery lotion to both hands and began stroking his much better than average sized cock until it was rock hard with the tip nearly reaching up to his navel. Phil had inherited his dad's equipment. His hard dick was easily over seven inches long and two in diameter. It was pretty too, smooth with a nice cock head that was already dripping large amounts of precum from his excitement. Phil's balls were large as well, easily two inches in diameter at their smallest dimension.

Phil however, was conditioned by abuse to hate his fine package. He was ashamed by the hard dripping cock. He just couldn't keep it from getting rock hard and dripping.

"Ok boy, enough of that. We can't have that thing making a mess on my carpet. What would the maid think?" teased Al.

Phil, not understanding, thought that Al was disappointed with him and he was crest-fallen he had made the young macho man mad at him.

He fell to his knees to Al, begging him to not throw him out. "I'll do whatever you want, Sir. Don't throw me out. I'll be good."

Al, immediately slipped his sweaty workout pants down, kicked them at Phil where they landed on his face. Phil froze, not willing to make Al mad by presuming to move the soft pants.

"Get over here cock sucker. I need my balls licked and cock sucked," Al barked.

Phil was very happy, he could stay! He immediately knee walked over and moved between Al's muscular thighs, reaching for Al's hardening cock.

"No hands, boy. Just lean in and lick my balls first, hands behind your back."

Awkwardly, Phil did as he was told and gingerly licked and sucked Al's large sweaty balls. He tried his best to make the licking pleasurable for the macho man. Phil didn't care that Al was younger. He didn't care he was a slave boy licking and sucking another man's balls. He didn't care that the macho man was holding his ears to guide him silently to the spots that needed attention. A macho man was paying attention to him!

"That's enough, boy. Now lick my asshole." Startled for a couple of seconds by this perverse demand he started to tentatively lick Al's sweaty ass. It wasn't that bad thought Phil. Al had a manly scent but it wasn't that bad. Al, quickly figured out this was new territory for Phil and let him explore. Finally he began getting impatient and ordered, "Get that fat wet tongue way in there, boy. Eat my ass. Lick the inside. Clean out my nice tasty ass, boy!"

Phil, into the filthiness of what he was doing and the pleasure he was obviously causing in this strong macho man, abandoned his tentative actions and put everything into licking and sucking on Al's tasty ass. Phil had learned a new trick.

After about five minutes of this intense ass eating, Al grabbed Phil's ears firmly and pulled his head up, ramming his eight inch thick cock down Phil's experienced throat. Al couldn't hold back any more and came in strong blasts that shot down Phil's willing throat.

Phil was in heaven. He had served his Master well.

After that night, it became a normal routine for Phil to come to Al's room after the day's work and worship Al's ass, cock and balls. The last night, Al allowed Phil to masturbate and catch his cum into a coffee cup. After edging for days, his cum blast was impressive. However, Al enjoyed Phil's show so he had him keep beating off into the cup, over and over until there was just no more cum left in the exhausted Phil. Al congratulated the tired sore Phil and ordered Phil to drink his cum down. No stranger to swallowing cum, Phil upended the hotel room cup and slowly sipped the large amount of cum down until there was nothing more than a thin coating in the china. Al had him use his fingers to wipe the remainder out and lick his fingers while Al took pictures with his phone.

Al had long ago written down Phil's name, address, business info and e-mail info. He even had Phil's bosses email and Ann's!

From that point on, Phil would meet Al online with his laptop web cam. Al would have Phil humiliate himself, ordering him to masturbate to the edge of orgasm, wrap his balls in rubber bands and beat his balls with a ruler when he disobeyed. Al even had Phil finger his asshole while Al watched. Throughout the filthy show Al called Phil a cock sucker, pussy boy, faggot, wimp, and anything else he could think of to degrade Phil. Strangely, the degradation and on camera cum eating made Phil very happy.

A couple of times Phil had missed his web cam appointment and his master was not there, sometimes disappearing for days. The absence of his master made Phil miserable.

Finally done with a long run of appointments on the road, Phil came home. His wife had left a note telling him that she would be home tomorrow, away visiting a "friend" out of town.

Happily, Phil contacted his master and advised him of the happy news.

Al, smiled and told him, "ok boy, get naked and get that pricklet hard. Get that asshole of yours lubed up. I want to see two fingers up that hot tight ass with your cock nice and drippy."

Smiling happily, Al's puppy did as he was told and soon was there, naked slid back with his feet on the desk, legs widely spread, his fingers stroking in and out of his ass while his hard cock dripped onto his belly.

Just then, Ann walked into the office!

"Well, pervert, I see you're giving Al a show again," she said.

Phil froze, with the fingers of one hand in his ass and the other wrapped around his hard dripping cock.

"Al told me you have no problem getting it up for him, faggot. We spent last weekend fucking like minks while you gave us both a show. We've shared several of them and I've been fucking him for months. I just left him at his place on the other side of town. He'll be here in a few minutes."

Phil started crying. He rolled onto the floor into a ball and cried like a little kid. His life was over. He felt so betrayed and ashamed.

Just then, Al walked in and both he and Ann started to undress. Al laid on his back in the king sized bed, his firming eight inch cock starting to rise. Ann, finished with her undressing, crawled onto the bed on her hands and knees to Al.

When she got to Al, she split her legs and crawled knees on either side of his thighs and slowly settled down onto Al's stiff thick cock. Her elfin child like body was tiny compared to the large macho Al. She rose up and, with one hand, pulled up Al's large dripping cock and put it at the entrance of her already very wet pussy. She slid down his hard cock slowly, moaning and groaning as she impaled her tiny hot body on his huge cock.

She started slowly, rising and falling, taking about five inches of his hard thick cock immediately and each time she rose and fell, took another bit. Her large firm breasts bounced up and down to her thrusts. On the deep plunge, she would sit and wiggle her hard muscular ass on his hard prong. She couldn't take him all at once! He was just too big and she was just too small. Finally, after a couple of minutes and several long anguished downward plunges, she had him all embedded in her tiny body!

He was all of the way into her. She stopped her up and down movement and slowly moved her trained body around and around squirming and moaning with his large cock all the way in. She began milking his cock with her hot slick muscular pussy.

She was magnificent. Al was in heaven! She was a fantastic fuck. Phil was a fool to let this get away from him but Al didn't care. Ann was the best piece of ass he had ever had. Each time they fucked, it got better as they learned each other's body.

Several months earlier Al had heard about multiple male orgasms and had been studying the seemingly mythical possibility. He had been working on strengthening his PC muscle and practicing his breathing, following the instructions as closely as he could. He had been able to achieve multiple orgasms without ejaculating when he masturbated and then later with partners. It was very difficult at first but after a lot of practice and work, now he could do it reliably!

He decided that if he could do it with this incredible woman, he could do it with anyone. He orgasmed without cumming once, and kept fucking. After 20 minutes he orgasmed again. Fifteen minutes later he finally let go and passed the point of no return. This time he orgasmed and ejaculated at the same time filling her clenching pussy as she had her own fifth hard muscle and tendon racking orgasm.

Exhausted, she rolled off of her lover and pulled her knees up against her firm full breasts to trap Al's thick cum in her hot pussy. She didn't want to lose a drop.

"Phil you cock sucker, get up here and clean my pussy!" She yelled.

Phil had stopped crying and uncurled midway through the magnificent show that Ann and Al had put on. He was just amazed that people could do what he had seen. He saw the cum coated huge cock of his master and his hot and sweaty balls, soaking in the left over cum that started to drip down his slightly softened cock.

As he crawled up on the bed, Al ordered, "She'll keep. Lick up our cum from my cock and balls, faggot. Get all of that cum licked up off my asshole and don't let any leak onto the sheets. I'm going to fuck your hot wife all night since you're not man enough to do it."

Phil, embarrassed by Ann watching him lick and suck Al's ass, balls and cock, quickly followed the dominant man's orders and swiftly cleaned his master.

"Ok, you asshole sucking cock sucker, get over here and eat our cum from my pussy so we can do it again."

Phil looked down at his newlywed wife's pussy. It was a mess. Her red cunt lips gaped and he could see down into her pussy and see her full of cum. She let her legs drop and a thick river of white cum started to swiftly run out of her red gaping pussy, "Lick the cum off my asshole and taint first, pig." Ann ordered.

He did as he was told, leaving her full pussy for last but he had to struggle to keep up with the strong thick flow as it rolled down her crotch to her asshole.

"OK asshole, wrap your lips around her pussy and suck all that tasty cum out of her and hold it in your mouth. Don't swallow until I tell you." Al ordered.

Again, the submissive husband did as he was told. He wasn't done, but he couldn't get any more cum into his fully distended mouth. He leaned his head back and opened his mouth, showing his dominant master how well he had done.

"Good boy cock sucker, swallow that tasty cum and finish up."

Again, Phil put his face into his wife's hot crotch and sucked the rest of his master's cum from her fragrant stretched pussy.

"Good job, boy. Get over here and make my cock hard for your hot wife. Suck my cock until I say stop." Al ordered.

Phil, happy with the praise for his obedience, plunged his face down Al's hardening cock. He deep throated and sucked. He licked Al's big juicy cock head while his hot wife watched beside him. She taunted him as he sucked cock. "Suck that cock, lick his balls, boy. Suck his asshole. Get your tongue way in there. I need another fuck, you useless little boy."

Stirred by the degradation from his hot wife, his long thick cock got hard as steel for the first time in her presence. She was making him hot.

Noticing Phil's cock getting hard and drippy while Phil sucked Al's ass, she laughed and commented to Al, "You were right. He is a faggot. Look how hard he gets sucking your ass!"

"OK, boy, you're done for now, Kneel at the end of the bed and wait. We'll be ready for you in a while.

All night the first fuck was repeated except after licking them both clean each time, sucking Al's ass in front of Ann, they ordered Phil to beat his meat while they watched and teased him, degrading him, calling him a faggot, cock sucker, ass sucking boy. The degradation made Phil hotter and hotter but they always stopped him before cumming.

Early that morning, no longer able to fuck anymore, Phil's wife and Al told him what would happen from then on. Al lived near by and would come over frequently for more nights like this one. Phil would be their cleanup man and entertainment.

Ann even got Al to agree to let her bring over other men to service her while her wimpy husband fluffed the men and cleaned up the cum so that she would get the maximum benefit from her each of playmates.

And so it went, from then on. Ann over the years had hundreds of men over for Phil to suck and her to fuck. Phil even quit the IRS so he could get a local accounting job and be home every night to do his duty.

Phil had found his place. He was a happy man.

Ann too was satisfied with her subservient handsome husband and her comfortable exciting life.

To outsiders, they looked like a happy couple and they were. Other stories at Nifty:

/nifty/bisexual/authoritarian/ironman

Authors posting to free sites get no reward for their work except recognition from readers. Support the sites that publish your free entertainment. E-mail the authors or if appropriate, vote and review their stories to reward the author and help them to improve their skills so they can write more hot stories for you.

The author does not condone child abuse, this story is meant as an erotic fantasy not real life. Anyone acting out such scenarios in "real life" can look forward to many unproductive years getting it up the butt by a fellow convict in their local prison. Note: I borrowed this from Kristen Archives, one of my favorite sources of erotica.

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