Thursday, September 19th, 1996

Jason had been Jack’s best friend since the two of them were in the 4th Grade.  They lived a block apart.  Throughout their latter grade school and junior high aged years, they had walked to and from school together every single day.  They’d spent long hot summers together. They’d spent the night at each other’s houses. They’d had epic pillow fights. They’d experimented with fireworks. They’d even gone on vacation together.

As the two boys grew older, they talked about a lot of different things.  From conversations about sports to arguments about movies and video games, their list of topics was broad.  Teenage boys being who they are, their topic of conversation more and more frequently became girls… and sex.  They imagined what their female classmates looked like naked. They discussed which ones they thought had nicer legs and better tits.  They tried to imagine what it actually felt like to have sex. They looked at nudie magazines for the first time together—and even saw an adult video or two.

One night when they were both sixteen years old, it was late.  They were camping out in a tent in the backyard at Jason’s house.  This was something both of them had really outgrown, but they still enjoyed doing it, because it gave them the privacy to have conversations about whatever they wanted, without having to worry about parents listening in.

As their conversation evolved that night and they kept pushing each other to explore other aspects of their favorite topic, Jack made the decision to mention something to Jason.  He felt that he and Jason were so close, and so secure in their friendship, that such a simple admission couldn’t possibly damage their relationship.

“You know what I’ve been wondering lately?” Jack asked casually.

“What’s that?” Jason answered.

“The last year or so, I’ve just really started wondering what it would be like to have sex with a guy,” Jack admitted.  As soon as the words left his mouth, he could tell by the expression on Jason’s face that he had said something wrong. He instantly regretted having said the words.

“What?” Jason quickly retorted.  “Gross, man, don’t even think about stuff like that.  Come on, that’s disgusting,” he continued, seemingly revolted.

The topic quickly changed to something else, and by the time both boys went to sleep that night, Jack believed it to have been forgotten.  The two never spoke about it again, and it had not seemed to have changed their friendship, at least initially.

However, over the course of the next several months, Jason began to distance himself.  On top of that, they transitioned into a new year at high school that fall, and their busy schedules frequently led them in different directions.  Jason was heavily involved in playing football in the fall and soccer in the spring. Jack was in show choir, drama, and a few other activities.

By the end of their junior year, they barely spoke to each other at all.  On one level, Jack knew this was the natural flow of the lives of two young people who had just grown to be very different.  On another level, he couldn’t help but wonder if his one idle comment had ultimately driven his best friend away from him.

At the conclusion of their senior year, they both graduated.  If you asked either one of them, they would still claim to be friends, but they were really friends in name only.  They rarely spoke to each other, they never spent time together. They had other friends. Different interests. Jason got a scholarship to play soccer and be a goalie for the local college.  Jack went off to a college that was about two hours away.

Throughout his first year in college, Jack didn’t give Jason much thought.  He was so busy adjusting to college life and going to classes that he didn’t have much time to think about old high school friends.  That is, he hadn’t thought about him much until early April.

One afternoon in early April, the phone rang in Jack’s dorm room.  He answered it, and heard

Jason’s all-too-familiar voice.  As it turned out, Jason’s college was closing.  Poor attendance and lack of local support had doomed the school financially.  The university could no longer afford to keep its doors open. This had been a major shock for Jason, who had an athletic scholarship and had fully intended on playing soccer for three more years.

He explained to Jack that he was transferring to Jack’s school and was in need of a roommate.  Needless to say, Jack was surprised. He and Jason had spoken so rarely the last three or four years that he couldn’t have imagined Jason wanting to be his roommate.  Yet, he found himself smiling, and instantly agreed. When he hung up the phone, Jack was elated. A new start, he told himself.  A chance to renew our friendship, and really set things right.

The next fall, Jack and Jason moved into their dorm room and meshed perfectly.  It was as if the previous four years had not happened. They agreed on what posters to put on the walls.  They agreed on what movies to watch in the evening. They even ate lunch together most days in the cafeteria.

But the one thing that Jack didn’t count on was Tammy.  Tammy was Jason’s girlfriend from high school. It was a relationship that Jack had never understood, from the moment they started dating.  Most guys date a girl that’s out of their league. But in Jason’s case, Tammy wasn’t even close to his league. In Jack’s opinion, his friend could have found a much better girlfriend, both in appearance, and personality (Tammy was loud and obnoxious).   

Despite the fact that they now lived in different towns, Tammy was still a constant presence in Jason’s life.  She maintained her presence in the form of phone calls. Long phone calls. Phone calls that could last several hours and totally disrupt whatever Jason and Jack had been doing prior to the call.

Jack adjusted somewhat.  He didn’t understand the relationship himself, but he knew how important it was to Jason, and he tried not to interfere.  He could tell though that Jason was both getting tired of the lengthy calls, and also becoming increasingly agitated and frustrated—about something.  Jack tried not to pry and never really asked what was frustrating his friend so much. He suspected he knew, but, ever since that fateful night when they were sixteen, he had been wary of talking about sex with Jason.

Which is why it shocked Jack when Jason finally broached the subject himself on a Thursday evening in September.

The two young men were sitting on Jason’s bed, using it as a couch.  The way their room was situated, this was the most conducive seating position for watching movies or playing video games.  Jason had just ended another of these long phone conversations when he half-threw the cordless phone into his pillow. He sighed deeply.

“Something vexes thee?” Jack asked, quoting a line from one of their favorite movies.  As he did, he picked up the VCR remote control and pushed play, re-starting the movie they had been watching.  (for the record, they were watching Goonies—another of their favorites).

Jason laughed in spite of his agitation.  He leaned his head back, propping it against the brick wall behind him and sighed again.  As he did, he subtly grabbed his crotch and rubbed it. “I’m just so Goddamned horny,” he finally blurted out.

Jack giggled but also felt slightly uncomfortable at the admission.  “I’ll be honest, that’s the last thing I expected you to say right there.”

Jason was still massaging himself through his jeans.  “She taunts me. She teases me. She talks dirty and knows I can’t do anything about it.”

Jack nodded his head, unsure of how to respond.

Jason continued.  “She’s trying to make me want to quit going to school here and move back home.  I know that’s what she’s doing.” He sighed again. “Over the last couple of years, I’ve just gotten used to getting pussy whenever I wanted it.  We’d have sex three or four times a week.”

Jack raised his eyebrows and—to his surprise—that wasn’t the only thing rising.  The frank conversation was arousing him, quickly.

“Hell,” Jason continued, “there was one time, our senior year, I think we fucked eight different times throughout the day.”

Jack hazarded a glance at Jason’s crotch and noticed that his friend was now sporting an unmistakable bulge in his pants, which he was now adjusting.  Jack raised his eyes to his friend’s face, and realized that Jason had caught him watching him adjust himself.

There was a moment of silence between them.  Down the hall, a loudmouth redneck was cackling at one dumb joke or another.  Just as Jack was trying to decide if it was a comfortable silence, or an uncomfortable one, Jason dropped the bomb.

“You remember when we were sixteen,” Jason started, “and you told me that you had always wondered what it was like to have sex with another guy?”

Jack nodded his head, unable to speak.  The taboo topic that he was certain had at least been partially responsible for driving them apart.  And now, here Jason was bringing it up in casual conversation.

“Did you ever find out?” Jason asked boldly.

“Wh—what?” Jack stammered, hardly believing he’d heard the question correctly.

“Did you ever find out?” Jason repeated.  “All those years in high school. With all those show choir guys, and drama guys that you hung out with.  Did you ever get your chance to experiment?”

Jack shook his head.  “No, I never did. Never even really thought about it, to be honest,” he admitted.  “If any of those guys were into that, they never talked to me about it.”

“That’s a shame,” Jason lamented.  “Are you still curious?”

This was a moment of truth for Jack.  Was he still curious? Of course, he was.  In fact, if anything, he was ten times as curious as he had been back then.  But could he admit that to Jason? What answer was Jason looking for? They had just now repaired years of damage to their friendship, would it all come crashing down again?

Jack closed his eyes and took a deep breath.  “Yes,” he said at last. “Yes, I’m definitely still curious,” he repeated, a little more confidently.

“How about right now?” Jason unexpectedly offered.

“Right now? What do you mean?” Jack countered, legitimately confused.

“I mean right now, you and me,” Jason explained.  He glanced around the room. “There’s no one here but us—no one would ever know.  I’m horny as hell, and you want to experiment. If you don’t like it, we’ll never speak of it again.”

Jack hesitated.  For a brief moment, he wondered if Jason was setting him up.  Attempting to gain a positive response, and then accuse him of being gay.  “So, what? We just take our clothes off right now and go to town?”

Jason shrugged.  “Not quite.” He sat up a little straighter, once again re-adjusting the now mammoth bulge in his pants.  “First, tell me you want it.”

Jack trembled, adjusting his own pants as he did.  “What—“ he started.

“Just tell me you want it, I know you do,” Jason repeated, cutting him off.

“I—I—I want it,” Jack finally stammered.

“What do you want?” Jason said as the two instinctively moved closer together.  “Turn around,” he whispered.

“I want—you,” Jack said as he felt Jason’s hands grip his shoulders.

“What about me do you want? What part of me do you want? And where do you want it?” Jason pressed.  As he spoke, his hands started massaging Jack’s neck, shoulders, and back.

“I want—“ Jack faltered again, unsure if he could even bring himself to say the words.  “I want your big fat cock inside me,” he finally mumbled. The words were just out of his mouth, when he felt his shirt being lifted up and over his head.  Jason’s strong hands feeling his bare skin for the first time.

With a startling realization, Jack became aware that this might have been the first time he and Jason had ever physically touched each other.  Sure, they’d bumped up against each other playing basketball or football, but he could not recollect either one having touched the other on purpose.  He allowed himself to relish Jason’s touch. His eyes rolled into the back of his head as Jason’s hand kneaded the tension out of his back and shoulders.

Then one hand reached in front to feel Jack’s smooth chest.  A soft, wet kiss behind his ear. Both hands now, feeling his pectoral muscles, tenderly teasing his nipples.  One hand dipped lower and unfastened Jack’s jeans.

An awkward moment of struggling later, and Jack’s jeans and underwear landed on the floor in a heap.  Jason gently encouraged Jack onto his stomach. He continued massaging Jack’s shoulders, back, and then thighs for a few more minutes.  As he did, he slowly spread Jack’s thighs further apart, placing him in the proper position for what was about to come.

Beneath him, Jack could feel his own member pressing against his body, fully engorged.  He couldn’t help but admit to himself that he was helplessly turned on by what was happening to him.  His heart was racing with nervous anticipation. He could feel the heat and wetness from his ass, as the appropriate regions became aroused.  This arousal was made all the more stimulating by who was touching him—who was behind him.  Jason, his lifelong friend.  Jason, whom his earliest gay fantasies had been about.  Jason, the only person he had ever expressed his desires to. Jason, whom he would have instantly done this same thing with that night four years ago.

Jack heard the sound of Jason’s jeans unzipping.  He braced himself, knowing what was about to happen.  Jason gripped his ass with one hand, and ever so delicately, slipped the tip of his finger inside him.  Jack gasped. Penetration. It was a first for Jack. He’d fingered himself before, but that wasn’t the same.  Someone else had penetrated him.

But he knew it was just a finger.  He’d caught glimpses of Jason’s cock when he was changing clothes, and had also seen that enormous bulge in Jason’s pants.  He knew what was coming.

Jason worked with his finger for a few seconds, loosening Jack slightly, and lubing him at the same time.  Then, the finger was gone. Jason pressed one hand against the bed, just to Jack’s side, steadying himself as he maneuvered into position.  The weight of his body compacting the mattress in a downward slope.

Then he felt it.  Jack sensed the head of Jason’s cock pressing against his ass.  It stayed there for a moment, like a diver waiting at the top of a cliff.  And with full force, Jason plunged inside.

Jack’s eyes widened and he opened his mouth to cry out in pain—but held it back.  It hurt beyond anything he had imagined. He had anticipated pleasure, instead, he felt as if his ass hole was being ripped apart.  Oblivious to his pain, Jason began thrusting. Slowly at first, but within a few seconds, he had found a steady rhythm as he plowed Jack from behind.

Jason's gyrating hips shoved Jack's body back and forth as he lay flat against the bed.  Jack bit into the pillow in front of him and gasped, “Fuck!” as he closed his eyes in pain.

Jason misinterpreted his cry.  “You like that? You want it harder?”  Without waiting for a response, his thrusting intensified, and he placed his hands on Jack’s shoulders, driving him into the bed even further.

Jack’s eyes opened and he inhaled sharply.  With a startling revelation, he became aware that the pain had disappeared.  His body had finally adjusted to the thickness of Jason’s engorged cock. In the absence of pain, he instantly became conscious of a thousand other sensations.  The thick cock filling his ass. Jason’s body weight pressing against his shoulders. The heat generating between their bodies. The sound of his friend’s breathing as it became increasingly labored.  As his mind interpreted all of this stimuli, he understood that all of these sensations—every single damn one of them—was pure fucking pleasure.

Jason’s rhythmic fucking continued, and Jack couldn’t help but start panting.  Sweat dripped from his forehead. The bed springs creaked quietly beneath them. As his friend fucked him, the thought curiously flashed through Jack's mind, I wonder what that redneck down the hall would think if he saw the two of us right now—I sure hope the door is locked.

After what felt like an eternity—yet, far too soon—he sensed the change in Jason’s body.  His strokes became quicker, his breathing faster. With one final, deep thrust, and a gurgled moan, Jason shot his load deep within Jack’s ass.  He thrust again, and again, digging his cock in even deeper as he pumped wave after wave of his cum inside Jack.

As the orgasm subsided, Jason collapsed on top of Jack’s back, pinning him against the mattress.  Jack could feel Jason’s muscular chest against his back. As the heat created by their two bodies intensified, Jack could sense the perspiration building between them.  Jason’s cock slowly became limp, and slipped out of Jack’s ass. Jason shifted his position, rolling off of Jack and sliding onto the bed.

He rested on his side, encouraging Jack to take up a similar position, with Jack’s back still turned towards Jason.  He wrapped one strong arm around Jack, once again caressing his bare chest, as he had done earlier. Jack closed his eyes and savored the sensation of being held by those muscular arms.  Jason’s strong pectoral muscles pressing into his back. All those years Jason had spent lifting weights for football. Jack knew Jason was a physically impressive specimen, even though, he had never thought of him as that, until this exact moment.

The two friends lingered in this position for quite some time.  Neither seemed in a hurry to separate. Jason made a very satisfied sigh, and Jack knew that his friend had just released an entire month’s worth of sexual frustration.  In a strange way, it almost made Jack feel dirty, as if he had been used. My best friend just used me as a surrogate pussy since he couldn’t fuck his girlfriend, he admitted to himself.  He dismissed the thought almost immediately.  Who cares, it was fucking awesome, he decided.

They watched the movie on the TV screen in front of them—it had been long forgotten quite some time ago.  How long did we fuck? Jack wondered.  Ten minutes? An hour? Jack had lost track of time, and didn’t care.  The action on the screen indicated that not nearly as much time had passed as it felt like.

Eventually, Jack felt an unusual sensation against his thigh.  With a start, he realized that it was Jason’s cock, becoming aroused once more.  Jack giggled slightly, and moved his thigh back and forth. “I feel that back there,” he teased, as a way of letting Jason know he was aware of his renewed hard-on.  Jack braced himself, preparing for what he hoped would be round two.

Instead, Jason changed position, laying on his back and stretching out with his hands under his head.  Jack turned to look at him. It was the first time they had faced each other since Jason had taken Jack’s shirt off.  He saw Jason’s glorious naked body for the first time, his bulging biceps, his well-rounded chest, his chiseled abs, his rock hard cock.

“Would you…” Jason started, but trailed off, as he glanced down at his waiting dick.  Jack didn’t quite pick up on the hint, so, Jason repeated his request, a little more plainly.  “Would you want to suck my dick?”

“Oh,” Jack responded, suddenly realizing what was being requested of him.  It had been phrased as a question, and a request, but Jason’s dominance had already been established.  He wasn’t asking.

Jack bent over, lowering his head towards Jason’s cock.  He had never had this done to himself. He had only seen it performed in a video—once—several years before.  He opened his mouth, licked at the head of Jason’s cock for the first time, and then opened wider to accommodate as much of the member as he could.

Over the next few minutes, Jack learned how to suck cock.  He experimented with different positions.  He licked. He bobbed his head up and down. He slurped it in and out.  He tried deepthroating, at least taking it as far as possible. He gripped the shaft, awkwardly at first, just using the tips of his fingers—he’d never touched anyone’s but his own.  But before long, he had his whole hand wrapped around Jason’s cock, working it up and down as he sucked.

As he worked at it, he discovered that he found the activity quite enjoyable.  He licked up the length of the shaft and then plunged it deep into his mouth, sucking and slobbering over it enthusiastically.  Jason made soft cooing noises and gentle moans. With each lick or suck, Jack could hear him mumble things like “Oh, that’s good,” or “Yeah, that’s the stuff,” and “Good God, you’re good at this.”  With each compliment, it only spurred Jack on, encouraging him to please his friend even more.

With Jason’s cock deep in his mouth, Jack heard Jason mutter, “I’m almost there.”  Jack knew what that meant. He had been longing for it. He had so completely become enamored with the act of sucking cock, that he wanted nothing more than to finish Jason off properly.

Jason thrust his hips upward, driving his cock deeper into Jack’s mouth as he erupted in his second orgasm of the night.  The first spurt of cum splashed against the back of Jack’s throat and he had no choice but to swallow or drown. He didn’t even get to taste it.  The second and third spurts glazed his tongue, and Jack eagerly pumped more of the syrupy, salty-tasting fluid into his mouth. He hungrily gobbled it down, swallowing every last drop Jason could offer him.

He slurped Jason’s cock from his mouth, allowing it to fall limp, and he stared up at his lover.  The expression on Jason’s face was one of pure contentment. Jack was shocked to discover how aroused he himself was.  He discovered that evening that it turned him on to sexually satisfy other people.

He wriggled his way back into Jason’s arms.  “You’re way better at that than Tammy is,” Jason mumbled.  Jason kept him close for a few minutes more, but it quickly became apparent that Jason was spent.  Within another fifteen minutes, Jack could hear the sound of Jason’s deep breathing, indicating his friend had fallen asleep.  Jack transitioned to his own bed, and before long, was also asleep.

When Jack woke the next morning, Jason had already left for his morning class.  The next time they saw each other, neither one spoke of the events from the night before.  They talked normally, about normal things, and for all practical purposes, it was as if the night had never happened.

That is… until three nights later when Jason received another phone call from Tammy.  After a nearly two hours long conversation, Jason once again hung up the phone in frustration.  He gazed longingly at Jack for a moment, and then abruptly announced that he was going to the gym to workout.

He returned an hour later, panting, and dripping in sweat.  He stared at Jack once again, giving him a look of resignation, and said, “It’s no use.  I tried to work it out of me, but damn it, there’s really only one cure.” While he was speaking, he crossed the room towards Jack’s bed, and took him.

After their second night together, neither tried pretending it wouldn’t happen again—nor did they attempt to avoid it.  After a couple weeks, they were fucking nightly, and frequently sleeping in the same bed. With each passing day, Jack felt that he was completely replacing Tammy in Jason’s life.  And he loved it. Jack’s crowning moment of awesome with Jason was the first time he was able to give Jason a blowjob while he was on the phone with Tammy—of course, she was none the wiser.  Both of them gained some sort of giddy satisfaction out of that.

One afternoon, nearly two months into their new relationship, Jason came into the room at about 12:30 and sat down in the chair at his desk.  He looked at Jack as he unbuttoned his pants and simply said, “I need a blowjob before I go to my one o’clock class.”

Jack didn’t ask questions, he simply moved himself into position, and gave his lover a blowjob, as he had requested.  Upon completion of the task, Jack swallowed, and sat back on his haunches. “Why did you need a blowjob so bad?” he finally asked.

Jason laughed as he pulled his pants up.  “Because, there’s this smokin’ hot chick who sits right next to me in that class.  Her name’s Amber. She’s been coming on to me for a couple of weeks now, and I’m afraid if you don’t give me a blowjob during lunch, she’s going to be giving me one at about 2:15.”

Jack felt a twinge of jealousy.

“You know I still want to be faithful to Tammy, I couldn’t bring myself to cheat on her,” Jason explained.

Jack grimaced.  He wanted to say something.  What am I? A fuck toy? crossed his mind, but he kept his mouth shut.

This pattern persisted for the next two weeks, with Jack giving Jason a blowjob three days a week right before his one o’clock class—every Tuesday, Thursday, and Friday.  Then, one Thursday, Jason didn’t come back to the room during lunch. Nor did he come back at two o’clock after his class was over. Nor did he come back at three o’clock.  Or four o’clock. Finally, sometime near five o’clock, Jason strolled into the room, with a very satisfied look on his face.

“Where have you been?” Jack asked warmly, but he knew the answer already.

“Fucking Amber’s brains out for the last three hours,” Jason answered honestly.  “Wow.”

And so, that was pretty much it.  Jason broke up with the missing-in-action Tammy, and started a new relationship with Amber.  No longer in need of a fuck toy, his interactions with Jack became less and less. They never quit fucking completely until Jason moved out, but it never was quite the same.

Jack didn’t resent Jason for choosing Amber.  He always knew that Jason would eventually find another woman.  He had just hoped it would take him a little longer. He remains grateful to Jason for being his first experience with another man.  And will always feel a stirring deep within his body when he thinks back to those dorm room nights in 1996.

Author’s note: This story was conveyed to me by Jack (no, that’s not his real name).  After he read my book, he wanted to share with me one of his own ‘first encounters’. I know, I know, it’s kind of a bummer ending, I’m sorry.  But, if I changed the ending, then it wouldn’t qualify as a ‘true’ story, would it? And seriously, Jack has no regrets about how it ended, and was really enthusiastic about relaying his story to me.  He loved every minute of the experience. To put it in Jack’s own words, “What else can I say about Jason, but, he fucked me gay.” What he meant by that was, he’d merely been curious before his encounter with Jason, but after Jason, he knew that he needed a good strong man behind him—literally.