0 comments/ 50659 views/ 9 favorites An Anal Beginning Ch. 01 By: caffinated 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. An Anal Beginning Ch. 02 John slept more soundly than he had in years. Even his dreams seemed to envelop him in elaborate schemes that involved by dominated by his beautiful girlfriend Heather. He woke in the morning with a hard-on that made his immediately reach for his shaft to relieve the pressure that had built to epic proportions during the night. His engorged shaft was aching for release, which John felt to compel to answer with a vivid fantasy of his Heather tying him to the bed on his stomach, and slowly and methodically thrusting into him until he burst. To John's surprise, he opened his eyes to find his seed had landed on the pillow beside him. The burst had been magnificent. Without internal torment, these repressed desires were leading him to the best orgasms he had ever had. But still he wondered. John spent the day in the yard working on the water fall he had agreed to install. The day was filled with the back breaking work of digging a six foot hole in the back yard which would then be water proofed and covered in stone. This was not something he had really wanted to do, but Heather had been staring at the lawn and garden magazines, fawning over the beautiful work that had been done. John hoped that by the end of his three days, he would have it functioning by the time she got home. As he finished digging the hole, he began making the trench back to the house that would house the pipe to connect the motor to the houses electric. It was tedious work, but left the mind free to wonder. He had learned a great deal last night, but forgot his initial purpose. Perhaps, since this wasn't as weird as he thought, there would be porn sites for this type of behavior. He knew if he stopped digging now, he would never finish, so he offered himself incentive, a reward, for when he finished the fifty foot long trench that needed to be finish. As John reached the house, it was all he could do not to leave the shovel laying against the house. He quickly ran inside to get on line when he realized how much he stunk. Perhaps a quick shower was in order. As he lathered up, his cock grew immensely as he thought about what he was about to do. But still the thought of pain entered the back of his mind. Also, what if she had taken it. After drying off, John made his way to the bedroom, and checked in the box located on the top shelf of the closet. This box had brought him hours of pleasure. Heather had introduced him to the world of sex toys. Despite his previous sexual prowess, John had actually been quite sheltered. As he opened the lid, he couldn't help but hold his breathe. There amongst handcuffs and shackles, gags and clamps lay his current desire. Bright pink and staring up at him. It was blazing, about the size of his own erect shaft. Eight inches that soon would be filling his throbbing ass. He grabbed the dildo along with some lube and threw them on the bed. His excitement was mounting as was the tension in his cock. He quickly grabbed the laptop from the living room and moved into the bedroom. In seconds he was online and quickly learned after a careful search that his predilections were well covered in the world of online porn. Soon, he was streaming videos that fulfilled his deepest desires. He almost said screw the dildo and his ass. The images were so powerful that he was ready, but he knew that he had to know. How would it feel? He watched as the men before him cringed in pain while still others howled in ecstasy. Which would he be? He lubed a finger and while watching a blond violate a young stud, began working his own finger into his ass. He went slow, and pushed out like he had learned from last nights research. It slid in relatively easy, only hurting for a moment as he passed the inner sphincter. Suddenly, he was aware of a new sensation. A pressure. A pleasant pressure that was building behind his testicles. He spent a moment just pushing in and out slowly. Just barely touching his own prostate. He felt his back arching and realized that he would never make it unless he sped things up. He slowly pulled the finger out and replaced it with two. Very quickly, he found himself open and ready, almost begging himself to be violated. Now was the time. As the young man on the screen bucked and rived in pain and enjoyment, John grabbed the vibrator and quickly squirted it with lube. He once again began pushing out with his sphincter muscle in order to allow easy entry. Soon he found himself engulfed in sudden pleasure. This time, there was no hint of pain. He quickly found himself riving on the bed timing his thrust to those on the screen before him. He couldn't help himself, he was in love. The feelings he had were so sublime, that he was at a loss for words. He simply moaned with pleasure. His secret fantasy fulfilled. But like all good things, it couldn't last. Moments before he was ready to allow that wave wash over him, the phone rang. Forget it, he thought to himself. With a quick glance he looked at the bed side caller ID and realized it was his wife. He had told her to call at this time, and despite his desire to finish, he knew he had to answer. With one deft finger, he killed the volume on the computer screen, and with his other hand grabbed the phone, leaving the pink dildo shoved discretely in his ass, up to the hilt. "Hello" he answered in the most casual tone he could muster in light of his current situation. "Hi Honey," replied the perky voice on the other end of the phone. "What are you up to?" "Well, to be perfectly honest with you, I was taking care of some of my needs...you know...since you aren't here to help. Just feeling a little neglected...if you know what I mean," John replied. "I know exactly what you mean. I did the same last night, but I forgot to back my battery operated boyfriend before I left, so we had to do it the old fashion way. " Thoughts raced through John's mind as the toy she was mentioning was shoved firmly up his ass. His hand started to move down to remove it. Just as he hand touched the base, he heard her voice. "Well, there isn't too much I can do from here. But I will try to help. Just close your eyes, and stroke your cock in those long lean strokes. Imagine me on top of you, dripping wet, my pussy pulsing with anticipation, just waiting for you to blow your cum into me. Can you feel how wet I am?" John was not slowly hand fucking himself. But this time, he used both hands. One hand on his cock and one on the dildo in his ass. He could feel himself growing close to loosing control. Yes was all he could mutter. "Speed up a little," came the seductive voice through the phone, "Speed up slowly, but consistently. Imagine me rocking on your cock, faster and faster, imagine my breasts in your face, my hands pinning you to the bed. Fucking you harder, and harder, and faster and faster" John noticed a change in her voice. A subtle change. He recognized it immediately. She was playing with herself and she was close to orgasms. He had heard this pitch before and felt himself at his breaking point. From the phone he heard the telltale sound of her loosing control. "Ahhhh, yes, yes, oh yes, harder faster, ahh.....thank you" But John only half heard her, as his own voice shrieked as his prostate exploded with sensation and his own seed shot all over his chest and stomach. His back arced and he lost all control, screaming into the phone, "Ahhhhh, that's right, fuck me harder, make me your whore!" As the waves subsided, he realized what he had cried. Never had he spoken like that before to her. On the other end of the phone, he heard a stunned silence. Then finally, "I promise, I will when I get home. But you will have to wait 'til then. Thanks for the orgasm, but I still miss riding that cock of yours. I assume you need to clean up, so I will let you go." "Well, before you go, how is the trip?" John managed to stammer still feeling overwhelmed by the things he had just shouted. He always preferred to be dominated, but never had he spoken like this before. "Better now," Heather said with a laugh, "Sad that this phone call has been the highlight of the trip. However, all good things must end, and I really need to go. I will see you in a few days, and if you promise to be good, I will even buy you a present. Something I think you will really love." "What is it?" John asked. "Can't tell. It's a surprise. See you in a few days. Now behave yourself." "Okay, love ya," John replied. "Oh, you will when you get your gift!" Heather said as she hung up. John slowly pulled the dildo out of his quaking ass and grabbed a towel to get the cum off his chest. He slowly walked to the shower on his quaking legs, wondering what was the gift, and how long would it be before he could experience another orgasm like that.