The following story is pure fiction. The characters all adults are not based on anyone in real life.
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James was 25 years old when he graduated from an Ivy League University at the top of his class and was sought after by many Fortune 500 companies in what amounted to a bidding war for his services. James was flattered by all the attention, but, he didn't want to get buried in the obscurity of the masses at the lower echelons of a massive corporation. When James got an offer from NTS, a telecommunications equipment manufacturer that was a recent start-up and now struggling through the growing pains, he jumped at the opportunity. The company's product line was brilliantly innovative and he thought that this job as a junior product specialist was his chance to shine. The best part was that the company was founded and located in the same town as the university to take advantage of their research capability and the potential to hire top talent who would enjoy living in the relatively slow paced college town.
James and Kelley had fallen in love at university and were planning to get married after she graduated next year. James was 5'10" 170 pounds with light brown hair, smooth except for some light chest hair and a treasure trail on his abdomen. He was trim with a well-defined body. Kelley was a petite natural blonde 5'2" 110 pounds. She was beautiful with small perky tits and nice ass. They had moved in together after James had graduated and accepted a position that kept him in town. It was perfect. Almost too good to be true. Both James and Kelley enjoyed having sex with each other and seldom went to sleep unsatisfied. Occasionally they would watch some porn together. Usually it was soft porn but the website did sometimes stretch the limits of soft.
One evening they watched a video that started as usual with kissing scenes followed by fellatio and cunnilingus then intercourse in several positions that displayed the penis and vagina prominently. The scene then shifted to the man licking and probing his partner's anus with his tongue. When he had her relaxed and wet he used his fingers to apply lube and stretch her hole using first one, then two, then three fingers. Kelley said "oh my god, he is going to fuck her in the ass."
"Yes, do you want to watch?"
"Absolutely, I'll bet that would hurt." She said.
"Let's see if she likes it." He said.
When the woman in the video could take three fingers to the first knuckle comfortably, the man asked her if she was ready. She told him yes. She was already kneeling with her ass elevated. He moved around behind her and put the head of his cock to her waiting ass. He gave a slow push until the woman grimaced and asked him to take it easy. He eased off and started a series of very short strokes, more like massaging her asshole than trying to enter her. Gradually the head of his cock was slipping deeper into her ass. As the head popped in the woman grimaced again and told him to hold still until she adjusted.
After a few seconds she told him to start moving slowly. The man started a slow rocking motion adding a half inch or so to each stroke. By the time he was balls deep the woman was moaning in pleasure and urged him saying "god that feels good, fuck my ass, harder, faster, FUCK me!" He sped up and they were grunting and moaning on each stroke. "FUCK, I love when you fuck my ass. Give it to me, fill me with your cock! Fill me with your cum!"
The video continued he fucked her ass and played with her clit until both reached an orgasm and as the video was fading there was a shot of cum dripping from her ass.
James' cock was more engorged than he could ever remember. It was all he could do not to grab his cock and have an orgasm right then and there. It wouldn't have taken much. He thought of Kelley and wondered if she would let him fuck her ass. James asked "what did you think about that?"
Kelley said "I am not sure, she probably has been doing that for ever and her ass is already stretched beyond recovery."
"But, did you see how much she was enjoying it?" James countered.
Kelley said. "Yeah, I did notice that and I also noticed how big and hard your cock got while watching." Then added. "How would you like it if someone fucked your ass?"
James' face went red in a hot flush.
"You would love that wouldn't you?" Kelley asked "how many men have fucked your ass?"
James was silent. Even though he was an anal virgin, he enjoyed playing with his ass and had probed with his fingers and small objects. He knew he wanted to try it with a man.
"Well?" Kelley demanded.
James decided that he had to come clean and admitted that he had fantasized about getting fucked for years.
Kelley said "Well then let's see how you like it."
James was confused as he watched Kelley cross to her dresser and opened her underwear drawer. She came back with a 7" dildo that was about 1½ inches in diameter and a tube of lube. James saw what she had and groaned with anticipation.
Kelley said "Don't expect me to lick your ass!" then added "Assume the position."
James got on his knees and raised his ass. Kelley applied an ample amount of lube then went to work on his ass with her fingers. She knew about the prostate and went looking for it. James was moaning and telling her how great it felt. Kelley had two fingers all the way in his ass and alternating her fingers tapped his prostate then held the finger together and slid them back and forth across the round walnut sized organ. James was on cloud nine.