An Anal Beginning Ch. 01bycaffinated©
This is the beginning of a longer story. It is the first piece I am publishing in this format. Your feedback is welcome.
John's deepest desires left him lost. He longed for something that went against every fiber of his being. John's girlfriend Heather had opened a door to his sexual exploration, and now John longed for more. His deepest desire was hard enough to admit to himself, so how could he admit it to her. He and Heather had grown quite close in there four year relationship, but he still had not been willing to vocalize this last desire.
John had been sexually active all through high school and even college, but despite his vast experience had remained sheltered until meeting Heather. She had introduced him to bondage, a fetish that he now relished with great sincerity. She was also the first woman who had ever allowed him to anally penetrate her.
Her creativity astounded him. On one occasion, she decided to make him her desert. She bought a sugar cone and some ice cream. She carefully broke the bottom of the cone and slid it down over the shaft of his erect dick. She filled the cone with ice cream, slowly licking and teasing. The visual display was all John needed, but the ice cold of the coffee flavored ice cream against his cock drove him absolutely insane. He had to fight hard against the urge to cum, and waited until she had devoured her desert, after which, she quickly devoured him.
Even with this adventurous spirit, he could not find a way to broach the subject that was his heart of darkness. As far as their love making has stretched his boundaries, there were some things a man just does not feel comfortable in asking. He secretly fantasized about scenarios where she would take complete control of him. But dared not ask for it. These wishes remained firmly fixed in his mind, and dominate his dreams.
Prior to Heather, it had been easy to repress these hidden desires to be dominated. He had been limited to conventional sex, and therefore wrote off these dreams as wrong, immoral, and even deviant. But with broader horizons comes endless possibilities. He longed to have Heather, armed with a strap-on, pound his virgin ass until he cried like her bitch while still begging for more. How could any real man want this?
His heterosexual blood filled him with fear and self loathing. John had never found himself even remotely interested in men. He did not want to fucked by a man, he wanted a woman to take the power over his only unexplored orifice. He wanted Heather to take that last control from him.
Since John began masturbating, he would sporadically have images of a blond in black lingerie violating him in this way. Often times, he would find himself turned on beyond the point of his control, but would stop saying this image was wrong. He would remind himself that he was straight, and that having someone fuck you up the ass made you gay. John kept this secret to himself, but Heather's openness made him see it as a possibility.
After months of silent torment and hidden moments by himself in the bathroom, he finally conceded that he must be gay. His sex life with Heather was active. He loved her body from her round, soft breast to her neatly trimmed pussy. He loved the taste of her in his mouth, and the feel of her warm wet lips around his cock. But facts were facts, he must be gay.
It was three days after this self revelation that Heather was to leave town and head for a wedding of a college friend. She was to be a bride's maid, which contented John, as he did not need to attend. He had planned to go, but Heather quickly realized that he knew none of these people, and she would be at the head table. She told him not to come and to stay home and relax. This suited John just fine.
On the day she left for the trip, John hopped on the internet and looked for a gay porn site. Without much trouble, he had found thousands. He began streaming video after video without finding any satisfaction. In fact, his stomach often lurched at the site of watching one man pounding another. John tried multiple sites but soon decided to simply give up and just let this dream be a dream. Despite feeling a little let down, John was also relieved. While not entirely homophobic, he did not feel that he was gay, and was relieved to find this porn did nothing for his sexual appetite but repulse it.
John began to log off of his laptop, but paused realizing that you could find anything on the web. John quickly opened his favorite search engine and began typing in different combinations of words, searching for a site that would fit his desires. The first two attempts left him at sites with guys fucking girls anally, or girls fucking girls with strap-ons anally, until he finally got the words in the correct order. He did not find porn, but instead found an article about pegging.
The word pegging was foreign to John, but after careful reading he learned that his desires, while perhaps not the norm, where not unprecedented. He felt a burden lift from his shoulders and could not describe this new feeling. His search for porn stopped, and his desired to learn all he could about the subject began. He spent a great deal of time carefully exploring a plethora of web pages, scouring for new information.
By the end of the night, he had received a crash course in human anatomy learning a great deal about the male prostate and also his reproductive organs. He also learned about sexual stigmas and how the practice dated back years and years. He was overwhelmed when he read stories of men going through the same inner turmoil. He was also energized with how many of the stories mentioned how willing their partners were once they had the courage to ask. John also learned the practical side of things, the types of lube to use, how to relax and reduce the pain. Of course in his dreams, pain of inserting something into his rectum had never occurred to him, but now it seemed a logical issue.
When John finally shut down the laptop hours later, he felt like an expert on the subject of pegging. But he was still unfulfilled. John walked to the bedroom thinking how his thoughts were pretty natural. Not something he would admit to the guys at the poker table, but natural. John had trouble falling asleep and decided to treat himself. He grabbed a towel off the rack, and for the first time masturbated to the image of Heather bounding him without hesitation, remorse, or self-loathing.