The New Boy at School

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A sheltered boy gets taken advantage of.
6.3k words
4.13
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Everyone. In this story is 18 years old or older.

Richard was reared by two strict puritan parents. He was home schooled all his life until his senior year in high school. His parents were tragically killed in an automobile accident the summer before that.

With his strict upbringing he wasn't allowed to have friends outside the family. Being home schooled left little, well no, opportunity for any social life. This contributed to his shy geeky manner.

Richard had grown into quite the handsome young man. He was blessed with one of those bodies that looked like he worked out daily but he never had to do any exercise. But nobody knew about it because of the ill fitting clothes he always wore.

His chiseled facial features were particularly hidden by the large horn rimmed glasses he wore. They also camouflaged his deep blue almond shaped eyes.

After the accident he went to live with his only surviving relative, Wendy. Wendy was his fathers step sister. She was from their fathers first marriage and quite older than Richard's father.

Richard's family was not a close one due to their strict puritanical beliefs. His step aunt Wendy was a stranger to him. It would take each of them some time to adjust to the new living arrangements.

Wendy was a very liberal person in just about every aspect of life. She had always had a progressive point of view.

She knew it would be a challenge dealing with a boy who had been reared in such a restrictive environment. She realized this right off the bat when she tried to give him the freedom to do things on his own. He had always taken orders and been told what and when he was allowed to do anything.

Wendy acknowledged it was going to take time for Richard to adapt to his new freedoms and surroundings.

When it came time for him to start his senior year in high school he was terrified. He'd always been home schooled and had no idea of what to expect on his first day. He had never socialized with any young people his own age.

Trying to fit in the first week of school was more awkward than anything Richard had ever experienced. His shy and geeky personality didn't help him come across as friendly. In fact his classmates read his standoffishness as being superior and snobbish.

It didn't take long for the "popular" crowd to turn on him. During the second week of school after the boys physical education class the boys decided to play a trick on the new guy.

As he was about to change out of his pe gym clothes the other boys grabbed him and stripped him down to only his jockstrap. They dragged him out of the boys locker room and across the hall to the girls locker room. They shoved him inside the door and blocked his efforts to escape by lodging themselves against the door.

The girl's physical education class was about to start so the locker room was full of the senior girls in every state of undress. As soon as one of the girls noticed the intrusion she let out a loud scream. This of course drew attention to what was happening. Screams, gasps and shouts of "get the fuck out of here" were heard from many areas of the locker room.

Richard pushed against the door with his back, determined not to turn around and reveal his nearly naked ass to the girls. No matter how hard he pushed the door wouldn't budge, being that the other boys were holding it shut.

Just as things were coming to a frenzied state a whistle sounded from behind the group of girls. It was the girls physical education coach, Martha.

"What the fuc..., heck is going on here?" Martha asked as she approached. When she saw what was causing the ruckus she couldn't believe what she was seeing.

"What are you doing? Are you crazy? You can't be in here...especially dressed like that," as she eyed his jockstrap.

"The...guys...from gym class...stripped me and shoved me in here," Richard blurted out.

As Martha grabbed him by his ear she asked, "If that's the case why didn't you run back out immediately?"

"They're blocking the door on the other side. I tried to escape but couldn't get the door open!" He pleaded.

Martha took a step toward the door and gave it a gentle push and it swung wide open. "I don't see anyone blocking your 'escape' son," she sarcastically said.

"I...swear...they were there just a second ago...I swear!" Richard beseeched

"I wasn't born yesterday and I'm not buying your load of crap." Martha explained. "You wanted to expose your nearly naked body to these girls while you got a good look at them undressing. That's what I think happened here!"

"No! I'd never do anything like that. You've got to believe me. I'm not like that!" Richard explained.

"All you nasty 18 year old boys are the same. Always wanting to sneak a peek. And you, you're worse, parading around in that...that symbol of manhood...that jockstrap. You might as well carry a sign saying, 'look at my body, I'm almost naked!"

"No ma'am, the other boys took off my gym trucks and left me in only this before pushing me in here. You simply must believe me!" Richard said.

"Well I don't believe you. There are no boys holding the door shut preventing you from leaving and yet you are still here," she said. "Furthermore, I do not like being lied to or called ma'am!"

With that she tugged him by the ear over to the nearest bench and in one fell swoop had him across her lap. His mostly naked ass was pointed directly toward the class of girls. This was their first glimpse of it. He had consistently kept his back to the door to prevent this very occurrence.

There were squeals, gasps and laughs when they saw his mostly naked ass for the first time. "That's payback, he saw me naked when he first came in," a voice rang out from the crowd.

Before Richard could take everything that was happening in, he felt a hard slap on his naked ass cheek.

"OUCH!" He blurted out from the surprise and pain combined. Then a second loud slap, and a third. It seemed to him that the slaps were coming so quickly she couldn't possibly have had time to lift her hand before the next one hit. His ass felt like a thousand bee stings were happening simultaneously.

It hurt so bad his legs were flailing wildly in all directions, trying to avoid the next slap. When his right foot nearly hit Martha in the head she ordered two nearby girls to grab each of his legs at the ankles to keep him from hitting someone, especially her.

This just made Richard try to struggle even more. The girls were having a rough time holding on to him. One of the girls suggested that if they moved further apart it might hinder his ability to move.

As the two girls slowly moved away from each other it worked. He had less control of his legs and keeping a hold of him was easier. The girls kept moving further and further apart. Richard now resembled an after dinner thanksgiving Turkey wishbone. His legs were spread wide apart and the deep crevice between his lily white ass cheeks was unsealed.

The group could now see his pink ass lips at the bottom of his crevice. For many of the girls this was their first time seeing any boys ass hole. It was quite the sight. More gasps and whispers prevailed through the group of young girls.

With everything that was happening to him, Richard didn't even realize it but all this being spanked and touched by girls had started his young dick growing. By the time Martha had finished her spanking punishment and told him to stand up, he had a full on raging 18 year old erection.

As he stood his erection was very obvious, being that his only cover was a jockstrap. His penis pointed skyward protruding outward in the pouch of his jock. The very tip of his circumcised penis poked out just above the waistband of his jock.

When he heard the uproarious laughter and saw the girls pointing at his crotch he looked down to discover what the attraction was. He couldn't believe what he saw. Not only did he have an obvious erection, part of the head of his junk was showing.

In an attempt to quickly fix the situation he overcorrected. He grabbed the waistband of his jock and pulled it up so fast and hard that his left ball popped out the side of the pouch. Another round of chuckles and gasps passed through the class of girls.

Martha again grabbed him by the ear(if you've never experienced this ear grabbing event, IT HURTS, just fyi)and out the locker room door they went. She dragged him through the hall toward the boy's physical education teacher, Mr. Parker's office.

The girls looked on as the two maneuvered their way down the hall. They watched as Richard's bright red ass cheeks jiggled with each step he took.

Martha basically threw him inside Mr. Parker's office and started telling him what had transpired. "This pervert was in the girls locker room while they were changing for class. He got a grand view of some of the girls undressed."

She continued, "He tried to tell me that the other boys in his class stripped him down to his jock and dragged him into the girls locker room. Then he proceeded to tell me they blocked the door from the other side preventing his exit. But when I checked the door there was no blockage."

"So what do you plan on doing about this?" She asked coach Parker.

Coach Parker told Richard to sit down. "I see enough boys in jockstraps everyday, I don't need to see you level with my line of sight."

Richard started to sit but as soon as his sore red ass touched the seat he jumped back up with a whimper.

"What the hell?" Coach Parker uttered.

Richard sheepishly turned his back to the coach showing his still very pink ass cheeks.

Martha spoke up saying, "I thought I'd teach him not to lie to me before I brought him to you."

"I see Martha. I'll get to the bottom of this and take whatever appropriate action is needed." Coach Parker replied. " I'll let you know about everything when it's all done."

Martha acknowledged his decision by nodding her head yes and left his office.

"Okay kid tell me the truth and start from the beginning." The coach said.

Richard repeated the entire story for him. He added that he was new to the school and had been home schooled. He also revealed that he'd never been allowed any social interaction with his peers and was having a tough time fitting in.

Coach Parker thought for a bit before issuing his decision "I believe you son. I also think your classmates are testing you. They are pranking you to see how you react. If you become angry and upset about this, you will be ostracized for the rest of your time here. If on the other hand you accept this prank as funny and laugh at yourself they will welcome you. My advice would be to laugh the whole thing off as a high school adventure."

"But what about coach Martha? She was so angry. She'll want me to be punished." Richard asked.

"Let me take care of her." Coach Parker said. "She has a 'secret' crush on me and she'll buy anything I tell her"

"Now get your shiny red ass out of my office and back to the locker room and get dressed before you cause any more drama." Coach said.

By the next pe class word had spread about what the girls had witnessed. They'd described the spanking, the visual of his ass hole when his legs were spread wide open, and of course his erection peeking out of the top of his jockstrap.

After his pe classmates had heard all the stories from the girls they couldn't stop teasing Richard. "Dude you popped a boner from being spanked by butch old coach Martha? That's just sick! I couldn't get hard for her if I had a gun pointed at my head." A classmate laughed.

Another of the boys who'd help push him into the girls locker room spoke up saying, "Come on guys, quit giving him such a 'hard' time. He's taken all this ribbing with good humor. That's okay in my book."

Hearing that put Richard somewhat at ease. Was he beginning to be accepted by his peers? He certainly hoped that was the case.

For the next couple of weeks things seemed okay. No more pranks were inflicted on Richard but he felt he wasn't being brought into the fold either.

The other boys could sense his willingness and urgency to be included into their social circles. The boys, who'd strategized Richard's embarrassing dump into the girls locker room, were planning more humiliating adventures for the shy geek.

One devious plan they came up with was to convince Richard to think that it was perfectly normal and an everyday occurrence to be completely naked at home around immediate family. They hoped to take it as far as getting him to think jacking off in front of his family was as normal as eating dinner together.

Their first attempt at this had one of the boys ask Richard to go with him over to a classmate's house to help him retrieve some stuff he'd left there. When the two boys arrived they were met by an older woman who greeted them and introduced herself as, Peggy, the mother. After they explained why they were there she invited them in.

As the two entered the living room Richard gasp and nearly lost his balance. There in the center of the room sat four naked boys in a circle. Not only were they naked but each one had an erection and were pumping away on them.

After the shock of witnessing what he'd just seen, Richard looked to the mother he'd just met. She had no reaction. In fact she asked, "Does anyone need anything to drink or maybe more lube?"

Richard couldn't believe what he was seeing or hearing. He turned to the boy who he had come there with to discover he showed no reaction at all. Everyone acted like nothing had happened. It was like this was an everyday thing.

The mother spoke up again. "Son, looking at Richard, are you okay? You seem a bit out of it. Would you like to sit down or maybe something to drink?"

Richard, finally finding his voice answered, "No...no thank you ma'am. I was just...well I've never...it's just that this...I can't even, my mind is spinning so."

The mother continued, "What dear? Go ahead and say or ask whatever is on your mind. We're very open and honest here."

"It's just...well your son and his friends...their...their naked and masturbating...right in front of you!" Richard spit out.

Everyone except Richard started laughing. After Peggy stopped laughing she said, "Hun, have you been living under a rock or what? Sexual behavior has changed in the past bit of time. We've all realized it's much healthier for young folks to be open and free about their urges. Hiding one's sexual urges only frustrates and inhibits your development."

"You should feel open and uninhibited when it comes to fulfilling your natural urges. Most all the family's I know practice this kind of freedom. It brings families closer together." She said.

"Both of you two are more than welcome to join in with these boys if you'd like." She added.

Before Richard could refuse her invitation the classmate he came with was stripping his clothes off and walking over to join the other naked boys.

Richard could only stand in the same spot still in shock and awe at what was happening. He watched as each of his classmates ejaculated, one at a time. With each stream of boy juice the mother congratulating them on a job well done. After the last one finished she passed out hand towels for them to clean up with. She even joked with her son saying, "I brought you a full sized towel 'cause I know you produce a huge load."

After Richard had left the entire group laughed hysterically for ten minutes straight. They'd done it. They fooled Richard completely. "Thanks cousin 'Peggy'," one of the boys said. "You played the part of my mom perfectly. I knew you being a lesbian could care less about a bunch of guys jacking off. Thanks again."

Back at home that evening Richard could not get that vision out of his mind. He also noticed his penis stayed stiff while he reviewed that event. He wondered, was this the way things were now? Was every family like that one? Was casual sexuality accepted everywhere? He fell asleep that night with a hundred different questions floating around in his head.

Being extremely shy and without friends he couldn't talk about what he'd witnessed to anyone which left his questions unanswered.

About a week later, after pe class, he was invited by yet another of the boys who'd pushed him into the girls locker room, to a pool party at his house on Saturday. "Just show up around 2:00 p. m.," the host told him.

Richard was excited and tentative at the same time. He so wanted to fit in socially with his peers but didn't feel comfortable around them yet. He kept going over the advice he'd gotten from coach Parker about going with the crown and being "one of the guys".

He arrived at the address he'd been given and knocked on the door. An attractive late 30's to early 40's woman answered the door.. She introduced herself as, Linda, the mother of the boy who'd invited him. She asked some simple questions to try and relieve the obvious tension he was displaying.

After chatting a few minutes she gave him directions through the house to get to the pool. She stopped him abruptly saying, "Here hun, I forgot to give you a towel, now have fun!"

He cautiously smiled and thanked her for the towel. As he opened the door that led to the patio and pool, the first thing he saw was a totally naked boy with an erection jump off the diving board into the pool. As he glanced around the pool deck he saw that every boy there was naked.

He heard the woman who'd just let him in speak directly behind him. "Here's some sandwiches, chips and sodas, please help yourselves. As she sat the tray down on one of the patio tables a gang of naked boys charged toward her. Many with raging erections.

She chatted with them as if everyone was dressed in swimwear. He even noticed a couple of the boys' erections rubbed up against her at times. She simply laughed and said, "You boys keep those loaded pistols away from me. And remember anyone who gets their jizz in the pool...cleans the pool. Oh yeah, remember if you need a judge I'm available and I promise I won't give preferential treatment to my son!"

Richard couldn't believe what he was seeing or hearing. The talk about them being naked with erections and cumming in the pool was so casual.

Suddenly Richard heard his name being called. That snapped him out of his semi trance caused by all this he was absorbing. The host boy was telling Richard to come on over and join them. "Have something to snack on if you like. You can leave your clothes over there, pointing toward a table that held the other guys clothes.

He walked over to the table and shed his clothes down to his swim trunks. As he rejoined the boys someone said, "Hey dude, there's no dress code here. Feel free to lose the trunks."

Richard paused before answering. "Thanks but...I'm not quite there yet. I'm adjusting to a whole new world here and I'm going to have to ease into this stuff.

"Cool dude but just know you're welcome to join in the fun at any time you want to." His host replied.

They ate, drank and swam for most of the afternoon. While there was a break Richard's curiosity got the best of him. He had to ask his host, "What did your mom mean when she said she'd be a judge if you needed her?"

After he chuckled he answered, "We sometimes play games and mom acts as a judge or referee according to the game we play. We told her earlier we might want her to judge our game of who shot the farthest."

"What kind of game is that?" Richard asked.

"Well, we line up in a single line and start masturbating. Whoever shoots their load the farthest wins and she measures everyone's distances." He explained. "Why tell you about it when we can show you how it's done."

"Line up guys we're going to play." He then yelled for his mother to come see who could shoot the best load. Six of the boys lined up and began fondling their already semi hard dicks.

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