[Fiction] Brian's Bridging

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This is my second story, first one that I've actually put effort into. All feedback is welcome, let me know what you think and whether or not I should continue!



This is the story of a boy named Brian and his experiences leading up to his freshman year of high school. Brian considers himself to be an average kid, blonde hair, blue eyes and is quite athletic. Even though he is very attractive it hasn’t gone to his head and he is also an extremely nice and sweet guy. He is friends with everyone in school and has a group of a few very close friends.

It was the last day of school before summer vacation and the clock could not move fast enough for Brian. That evening there was a bridging ceremony scheduled for the eighth graders where they symbolically move on from middle school and enter the real world that is high school. Afterwards there was a dance planned by the high school for all of the graduates, since this is a large high school there are multiple middle schools that feed into it and this is the first time that the entire freshman class would be together. The dance was all that was on Brian’s mind all day. He was ecstatic for it to say the least. Brian and his best friend Garrett had made plans to have a sleep-over after, though neither intended to do much sleeping. You only graduate eighth grade once, and they intended to live it up while they could. Garrett and Brian have been best friends since birth practically. Their parents are good friends and they lived very close together. They’ve made the long mile and a half trek home from school together every single day of middle school

The bell finally rang to end the school day and Brian headed to meet up with Garrett outside in the schools courtyard by their usual tree for the last time. When he saw Garrett already waiting at the tree he ran up behind him and basically tackled him while exclaiming, “We made it! We’re finally done! I can’t wait for tonight!”

“Haha yeah I know, but get off of me! We aren’t done yet, we still have to sit through that boring ceremony tonight!” And with that, the two friends began their long journey home together for the last time. Both boys were so excited to finally be done with school that they decided they’d rather not just go home alone and that it would be much more fun if they hung out until they had to get ready to go to the bridging ceremony. Garrett suggested that since his parents were both going to be at work until it was time to get ready for the ceremony that they should go to his house. When they got to his house both boys were very hungry and so they decided to cook a frozen pizza up for a snack. They decided to watch some TV while waiting on the pizza to cook. Garrett led Brian into the basement TV room and dove onto the couch, leaving just the love seat for Brian. Garrett’s mother had been doing laundry the previous day and had left a stack of clean clothes on the love seat that Garrett still needed to put away in his room. Brian picked up the stack to move the clothes out of his way and in doing so something in the pile caught his interest. Brian noticed on the top of the pile was Garrett’s usual boxers, were a couple pairs of Hanes boxer-briefs. Brian had only known Garrett to wear boxers, so after setting down the stack he pointed to the top and asked, “Do you wear those?”

“Sometimes. It’s nice to mix it up on occasion, I actually kind of like them better than my boxers.” Garrett retorted.

“When did you get them?”

“Oh I’ve had them for a while,”

“How come I’ve never seen you wear them before when were getting changed for PE?” Brian probed

“I don’t wear them on days we have P.E., boxers are better for P.E.” Garrett replied.

“Sounds like you don’t want anyone seeing how small your bulge is man! I can’t imagine my boys being constrained all day, but whatever floats your boat man. I am going to stick with my boxers though haha.”

“Have you ever tried wearing anything other than boxers?” Inquired Garrett.

“Well yeah I wore tighty whities when I was little, but I switched over years ago.”

“So you haven’t tried wearing anything else since?”

“Nope, I’m not a little kid anymore haha,” Brian shot back at Garrett, killing the conversation. Although he didn’t show it, Brian was hurt by his friend’s words and a new insecurity resulted.

The timer for the pizza went off and Garrett got up and left to go get it. Realizing he was alone, Brian went over to the pile of laundry. Brian had on occasion seen boxer-briefs on some of his classmates in the locker room, but couldn’t really look at them for fear of being called gay. Now that he was alone with a pair, curiosity got the best of him and he picked up a pair. They were light blue and made of a very soft yet thick and heavy material. Brian held them up to his face to see they were size S (28-30). Brian was completely mesmerized by them.

When Garrett got to the kitchen he found that the pizza needed a few more minutes so he went out into his garage and fetched a couple cans of pop for them to enjoy. When he walked through the door to the TV room in the basement he was very surprised by the scene he found. After being ridiculed only minutes previously for wearing them, his best friend Brian was holding up, and staring at a pair of his boxer briefs. Completely shocked at what he was seeing, Garrett stayed silent in the doorway.

“Hahaha what was that? Hahaha” Garrett burst out after watching Brian put his underwear to his nose and take a big whiff.

“AH! Sorry. Nothing.”

Reacting like a busted criminal, Brian threw his hands in the air, throwing Garrett’s boxer-briefs into the air. To Brian’s horror, they hit the ceiling fan above and made four complete rotations before shooting towards Garrett and striking him in the face. Shocked, Brian stammered out, “Sorry! You startled me. Sorry. I didn’t know you were there.” His face may as well have been a stoplight because it instantly turned a deep red and he couldn’t move or think for that matter.

Although extremely embarrassing for Brian, Garrett found this whole situation quite amusing. “What exactly were you doing with these?” Garrett asked while picking them up off the floor in front of him.

“I was just looking at them, I’ve never seen a pair before… You said you like them better than boxers?” Brian said trying to explain himself.

“Yup, the support is nice, you should try them on.”

“No, they don’t look comfy and no way am I putting your underwear on.”

“If they were not comfortable why would I be wearing a pair now?” Garrett asked while lifting his shirt. “I dare you to go in the bathroom and try them on, what are you afraid of?” He challenged.

Feeling his pride was on the line, Brian began to get even more defensive. “I’m not afraid of anything, but I’m fine in my boxers.”

“If you’re not afraid of anything, prove it. Lets play a game of dares, just daring each other back and fourth until someone gives up.” Garrett suggested.

“Alright, I’m down so long as everything that happens stays between us two and nothing dangerous. What is the forfeit for the loser?“ Brian asked.

“How about if the loser has to do whatever the winner says until after we get back from the dance tonight?” Garrett suggested.

“You’re on!” Brian replied, grabbing the boxer-briefs and heading into the bathroom, locking the door behind him. He undid his pants and his jeans dropped to his ankles, he stepped out of them and was left standing in just his pair of blue and white checkered plaid boxers. He took his boxers off and slid the boxer-briefs on. They were tight fitting on Brian and he found them to be very comfortable and secure. Brian liked how snug they were and he ended up getting a little hard from it. He pulled his jeans back on up and returned to the TV room with boxers in hand.

“Well, what do you think?” Garrett asked

“They aren’t as bad as I had expected, but I just don’t get them. Wouldn’t choose to wear them normally.”

“You sure about that one? Because you’ve been pitching a tent since you came out of the bathroom.” Garrett remarked while pointing at his friends bulging member.

“Shut up! I have not, I’m always this big! I dare you to strip to your underwear for the rest of the game!” Brian shot back hoping to defer his embarrassment.

“Alright, no problem.” Garrett said, removing his shirt and socks. He hesitated a second after undoing his jeans before letting them fall to the ground, revealing his pair of blue stripped Champion boxer-briefs. He then stepped out of his jeans confidently. “I dare you to strip naked for the remainder of the game.”

Shocked, Brian couldn’t say anything he just stared at his friend wide eyed for a minute. Without saying a word he then took his socks off which was quickly followed by his shirt. He unbuttoned his pants, letting them fall to the floor leaving Brian in just his boxer-briefs. He then stepped out of them for the second time that evening. No one had ever seen Brian naked before, especially not while his member was standing at attention. Feeling very exposed standing in front of his friend in just his boxer-briefs, Brian asked, “What if your parents come home?”

“If they do we will hear the garage door when they get here and we are in the basement, we will have plenty of time to get dressed. You’re just embarrassed that this whole thing is given you a semi. Don’t worry about it! You’re just being chicken.”

Brian became very worried about his penis size when Garrett referred to it as a semi, because this was the hardest Brian’s penis had been in his life. Brian grabbed the waistband of his underwear and yanked them to the ground before Garrett could finish saying chicken. While getting the underwear off his feet in a frenzy, Brian ended up losing his balance a couple times. Brian’s 4” erection pointed straight ahead at Garrett for a short time before he started holding his underwear up to cover up. This was the first time Garrett had seen another man’s erection, and he could feel a stirring begin in his own shorts.

“Wow, with how much crap you were giving me for my underwear and how I must have a small package, that’s all the bigger you are?

“Shut up! I dare you to strip naked for the rest of the game too, but you cannot cover yourself up at all.” Brian dared.

“That’s not fair, you get to cover up!” Garrett protested.

“A dares a dare, you should have been more specific with yours.” Brian retorted.

“Fine…” Garrett quickly stripped off his boxer-briefs and kicked them aside. Garrett was feeling a little too exposed so he said “You were right, there its getting close to when my parents are getting here, we should be dressed.”

“Does that mean you’re quitting and I win?”

“Well no, I am not quitting, but I think we should stop now and finish later tonight when my parents are sleeping.”
“Wimp. I win.”

Not wanting to lose and fearing the consequences, Garrett took things to a new extreme and said, “Since its my dare I dare you to go hangout in the kitchen completely naked until my parents get here, you cant leave or put on clothes until they walk through the front door.”

“You’re right, we should wait til later to finish this up.”

“So I win? You just backed out Brian.” Garrett inquired

“That’s not fair, I already won! How about we both get the same punishment?” Brian suggested.

“That sounds good to me. Since you were the first between us to actually refuse to do a dare, I get to pick it, lemme think.” Both boys started to get dressed, when Garrett noticed Brian was stepping into his boxers he got an idea. After getting dressed, Garrett left Brian in the TV room and went into his bedroom. He went straight to his dresser and pulled out his underwear drawer. He dug around in the back corners until he found what he was looking for. He found two pairs of old Hanes tighty whities boys size XL from when he was a kid. Garrett quickly put on a pair and went back to the TV room fully dressed with the second pair in his pocket.“

“So, the dare is you’ve gotta wear the same kind of underwear as me until after the dance tonight.” Garrett explained.

“Easy enough” Brian remarked, he then picked up the boxer-briefs he had been wearing earlier and started heading to the bathroom.

“Where are you going with those?” Garrett asked

“To put them on… you were going to wear some like these tonight right?”

“Those are not exactly what I had in mind…” Garrett said as he reached into his pocket and began slowly pulling out the pair of briefs. Brian saw what he was pulling out and couldn’t believe it.

“Where did you get those? There’s no way I’m going to wear them, what will you wear?” Brian protested.

“I’ve had them since I was little. Never bothered to go through and throw out my old underwear and my mom never did so I’ve got a couple pairs left.” Garrett explained while lifting his shirt to show his waistband. Brian took the briefs from Garrett and went into the bathroom. He hadn’t worn a pair of briefs since elementary school and when he tried them on he was surprised to find he actually thought that they were comfortable than the boxer-briefs from earlier. He pulled his jeans back up and exited the bathroom.

“How do I know yours are actually tighty whities like mine? You could be tricking me and wearing a pair of white boxer-briefs.” Brian accused, and with that Garrett unbuttoned then unzipped his jeans and lowered them just enough to show the full cut of the underwear before pulling them back up.

“Since you saw me in mine, you’ve gotta show me the same” Garrett suggested. Brian hesitated for a second, embarrassed by the erection he had, but he agreed because his friend had done the same. Garrett’s parents came home not long after the boys had gotten dressed. When they got there Brian decided to head home to get ready for that night.

[HondaJunkie93]

Interesting start..... looking forward to more. Keep up the good work!

[HondaJunkie93]

Hopefully you didn't give up on this story because of lack of comments! Still waiting for an update.