If you enjoy this story, please visit my blog: goodgaysexstories.blogspot.com.
New Briefs (part 1)
Dan had just emerged from a grueling fall semester aloofly disheveled: a college student too submerged in his studies to realize his appearance. His hair had grown shaggy and curly on the sides. His sweaters had accumulated holes and stains. His face was sunken in and sad, like a middle-aged insomniac's--a candidate for an eye job.
Dan spent the holidays sleeping and eating and loafing around his parents' house. On the day after Christmas, his mother pressed a twenty dollar bill into his hand and told him to go the barber. The following day, she gave him her credit card and told him to go clothes shopping. At a department store, he bought, among other things, underwear. He perused the men's selection, admiring the models on each package. He could not, however, find anything in his size. He retreated to the boy's department and selected two packages of medium-sized briefs.
In front of his bedroom mirror, Dan removed all of his clothing to model his new underwear. Dan was short and slight and appeared several years younger than his age of twenty. He admired himself in a black pair, which was tiny. They gripped and framed his package, making it appear larger. He turned around and admired the snug fit on his rear.
The thought of someone admiring him in his underwear aroused him. He had been celibate all semester--the thought of trying to meet someone was too overwhelming. But now he was suddenly obsessed with sex. He stared at himself and his cock grew hard in the briefs, which restricted it from protracting outwards.
He imagined himself before a man sitting fully clothed behind a desk. The man would ask him to describe a particular fantasy. Dan rubbed his package through his underwear, imagining that this strange man was instructing him on how to do so. He pinched his nipple with his free hand. He shut his eyes tightly. He rubbed harder.
"Pull your cock out," the man commanded. This man would have a slight German accent, Dan decided. Dan lowered the elastic waistband, exposing his cock, which, now free, could finish growing. His cock was small but proportional to the rest of his body. He stepped out of the briefs. They lay on the floor, and Dan could see a dark spot of precum. He resumed masturbating.
"Now, tell me about the first time you were fucked," the man said. Dan told him about the sixty-year-old man he'd met on the Internet. They'd had coffee, then gone to the man's apartment. Dan had passively followed the man's leads. He met each short hard kiss that resembled a bite. He allowed the man to pull off his shirt and pants. He sat on the edge of the bed under the man's grip and took his penis into his mouth, when the man said, "Do you want to suck my dick, baby?"
Minutes later, as Dan lay on his back, the man placed Dan's ankles on his shoulders and said: "I don't mean to be vain, but you're lucky you met me. You're about to experience the most amazing thing in the world." He then penetrated Dan easily and almost painlessly. Dan was too bashful to ask him to put on a condom. He fucked him quickly. "Does that feel good? You like that?" he asked. "Yes," Dan responded. When the man pulled out, he asked, "Do you want me to cum on your face?" Dan was too embarrassed to say no. He straddled Dan's face and milked out several small globs, which fell onto Dan's face. "Oh, man," the man sighed and laughed, apparently proud of the work he'd done.
The stranger at the desk asked if Dan had enjoyed the experience. "It was ok," he said. The stranger asked if it turned him on to recall it. "Yes," Dan said.
"Does it turn you on to be used like that?"
"Yes."
"Does it turn you on to be degraded?"
"Yes."
"Does it turn you on that he fucked you bareback without asking?"
"Yes."
"Do you think about this encounter when you masturbate?"
"Yes." Dan's legs were now shaking beneath him. He felt he couldn't stand much longer.
"I want you to cum now," the man said.
Dan's whole body trembled as cum spewed out and onto the floor.
The man complimented the size of his load. "Good work," he said.