New Friends and a Roommate Ch. 01

New Friends and a Roommate, Ch. 1

My name is Timothy, I attend USLA, and live off premises all year long as I attend summer classes for an early graduation as a lot of kids that attend USLA do. Its close enough to home base so I can easily see family and friends over a weekend trip staying overnight at my parents' house.

My roommate Todd does the same, he's what you would call an alpha male but he's a genuinely nice guy. Yes, I help him with some of his trig assignments and he fixes me up on LA Chargers tickets so the games are definitely a fair trade off.

We're in our second semester and Todd is making plans to go meet up with some friends.

"Todd... Todd," I whispered as he was on the phone with a friend of his.

"Hold on," he told his friend he covered the phone with his hand.

"Can I come?" I begged.

"I don't know Timothy."

"C'mon man, I never hesitate to help you out with your homework."

"It's not you, my friends can be a little insensitive... they can play some very cruel

jokes and stuff," he worried.

"Look at me, you don't think I haven't been picked on before," I explained with my arms spread wide.

"Okay, I'll ask."

"Thanks man," I was hoping to hear a yes.

"Hey, do you mind if I bring a friend?" he asked.

Todd turned to me and shook his head yes.

I jumped up and down with excitement and took a quick three minute shower and was ready to go.

We walked three blocks north to Oakland Dale Ct and knocked on the door.

"Hey man," the guy told Todd as he let us in then gave Todd the guy hug.

"Dan this is my roommate Timothy, Timothy this is Dan," Todd introduced.

"Nice to meet you," Dan said nodding his head.

"Nice to meet you Dan," I nodded back. I was so hoping to fit in the clique.

"Everyone's in the family room playing pool," Dan said as he led us to family room.

"Hey everyone, this is my roommate Timothy so be nice," he raised.

"Hi Timothy," everyone shouted sarcastically.

"That's Mia, Sam, Lenny, Rachelle, Tiffany, Brooke, and Lisa; this is her house," he introduced pointing to them in order from left to right.

"It's nice to meet everyone," I smiled, anyone would smile, the girls were extremely hot and dressed to kill.

"Todd... don't be rude, get your friend a beer," Lisa commanded.

"Do you want a beer Timothy," Todd asked.

"Of course he wants a beer, why else would he come to a pool party?" Tiffany laughed followed by a bit of laughter.

"Sure, I'll take one," I answered though I've never tried one but I had to look cool.

"There's a lot of beer in the fridge so I hope you can drink more than one," Lisa joked.

"No problem," I laughed trying to fit in.

"Here you go," Todd said as he handed me a beer.

"Flying Dog, I never had one, should be interesting," I commented.

"Timothy, what beer do you like?" Rachelle asked me.

"Bud, Bud Light," I answered seeing the commercials.

"Really, my cat drinks Bud too," he joked.

I laughed with the rest of them.

"Do you want next game?" Sam asked me holding up the pool stick.

"Sure!" I exclaimed.

"What are you guys playing for?" Todd asked.

"You lose, you guzzle a beer," Sam replied.

"I don't think this is a game for you?" Todd whispered in my ear.

"Why not?" I whispered.

"I just don't think it's a good idea."

"Why?" I asked again.

"Because I know my friends, and I don't think it's a good idea."

"Timothy, you're up," Sam said handing me the cue stick.

Todd's phone rang and he answered it. "Hey guys, I have to split."

"What's up?" Dan asked.

"My mom was in an accident and she's on her way to the hospital," he replied.

"Is it serious?" Brooke asked.

"Possibly a broken arm but I should be there," he answered.

"It's early; are you coming back?" Dan asked.

"I should be; c'mon Timothy lets go," Todd blurted.

"Let him stay... you're coming back, besides, if it gets dark one of us will walk him home," Sam blurted sarcastically as the others laughed and he put his arm around my shoulders.

"Todd... I'm good; take care of your mother," I insisted waving him off so he would hurry.

"Fine, but behave yourselves," Todd said as he left.

I broke and three solids dropped, I ran the table, and my opponent, Sam, had to guzzle a beer.

"You're pretty good Timothy," Sam laughed.

"Well, we had a pool table at the house, I've played a little."

Again I broke and dropped a solid but missed my next shot.

It was Lenny's turn, there wasn't a shot so he hid the ball which gave me no shot so I banked the ball and hid it between two balls. If he was any good he could possibly take one into the corner pocket. He made that shot and then another but missed.

The game lasted a while until he finally won.

"All right Timothy, guzzle!" Lenny exclaimed as they all watched me.

"Burp! Excuse me!" I laughed and everyone joined in.

"Here Timothy," Lisa handed me another beer before she took the cue stick from me.

"Drink up man," Dan held his beer up and they all took a drink; then they all looked at me like I did something wrong.

"Timothy, drink up," Mia giggled.

"Sorry," I was nervous and downed a third of the bottle.

"That's the way to go Timothy," Sam cheered.

"Do you have a girlfriend Timothy?" Mia asked.

"Not at the moment."

"Well, maybe you'll get lucky tonight," Tiffany remarked as the rest of the girls giggled.

After three rounds at the pool table I had guzzled three beers and drank three between the three I found a seat on the couch, then, I passed out.

"I think Timothy is totally out of it," Sam said as he waved a hand in front of my face unbeknownst to me.

"Well, we knew he was a lightweight when we saw him," Dan announced.

"Ok, so, what can we do to him?" Lisa asked.

"We can shave his head!" Lenny blurted.

"Yea, he's got locks like a girl, can you imagine the surprise when he comes around?" Mia brought up.

"C'mon, he's Todd's roommate, give him a break," Rachelle suggested.

"No, we can do this?" Tiffany added.

"We have to do something to him that Todd won't pick up on when he comes back, if he does come back," Sam recommended.

"Yeah, we can, we just have to think outside the box," Lisa stated.

There was complete silence in the room as they all thought about what they could do to Timothy.

All of a sudden Brooke began to laugh.

"What, what's so funny Brooke?" Sam asked.

"Wait," Brooke commanded.

"C'mon Brooke, what is it?" Lisa curiously asked.

"No, no, we can't do that," she sighed.

"Brooke, I can see it on your face," Lisa asked.

"Well... no, forget it," Brooke had second thoughts but laughed again.

"Brooke, at least share it with us," Rachelle laughed.

"Fine, but if we do this one, no one is innocent," she stated.

"Well, what are you waiting for?" Lisa hurried.

"We can dress him like a girl, doll him up, and have the guys fuck the living shit out of him," she said devilishly.

"Wow, I'm not gay!" Dan exclaimed.

"Me neither," Sam stated.

"I'm out too," Lenny added.

"What's the difference between his cock sucking mouth and ours?" Mia asked.

"Anal sex is anal sex, what's the difference?" Rachelle inquired.

"And if you don't do it, our little deal, is off!" Lisa exclaimed.

"What deal?" Sam asked.

"The deal where everyone in this group agreed to an open relationship with one another; that deal!" Tiffany explained.

"What's that supposed to mean?"

"It means that if you can use our mouth and ass to get off you can use his too," Lisa scolded the boys.

"That's right, we can find another "boy band" to fuck... and there's a lot of them out there," Brooke said seriously.

"C'mon, we'll have a party... after party... afterwards," Lisa mentioned trying to coax them on.

"An orgy," Mia laughed.

"Where did that come from?" Lisa asked.

"I always wanted to lick your pussy," Mia remarked.

"All you had to do was ask," Lisa replied.

"Fuck, you girls are bi?" Lenny was blown away.

"Just fucking with you pervert," the girls giggled.

"Why not, an orgy, one night, anything goes, agreed?" Brooke spoke up wanting to see her plan followed through.

The girls agreed.

"Fuck, I'm in, on one condition," Dan told them.

"What?" Brooke asked.

"I get to wear a condom," Dan insisted.

"The New Kids on the Block are now the Old Kids out on the street," Tiffany remarked sarcastically.

"Fine, but I'm taping your ass first," Dan stated.

"It won't be the first time," Tiffany laughed.

"Kinky bitch!" the girls joined in.

"Just kidding but I'm game," Tiffany laughed.

They all agreed that an orgy would take place later if everyone participated but it would be a onetime deal just to seal the deal.

Lisa went to get her 11nth grade Halloween costume, a short black sexy leather maid's outfit with breast inserts for bigger boobs, black four inch stilettos, and two pair of handcuffs if needed.

Sam went to get the plastic Lisa's dad used for a painting tarp he recently used that was in the garage.

Timothy's face was as smooth as a baby's butt but he would still need some trimming so Mia went to Lisa's bathroom to fetch shaving cream and a razor.

Rachelle went to the kitchen for some coconut oil since no one admitted to having anal lube.

Tiffany and Brooke looked through their purses deciding how to proceed with his makeup.

Everyone gathered back to the room.

Mia decided to record their dirty deed at the last minute without reason and without intentions. No one minded because it could be something to look back on for fun.

Everyone looked to Brooke wondering if she had planned out an idea or if it was just a thought.

Brooke began directing, they would lay Timothy unto the plastic tarp and remove any unwanted hair and then use the blue tarp for a back drop so no one could recognize the furniture in the recording. The last thing they wanted to do was to tip off anyone where this may have occurred.

Once Timothy was stripped and shaven the boys held up the plastic tarp in the background and Mia began filming.

"Mia, make sure the angles are good," Lisa told her.

"Got it."

"Sam can you somehow wake him up?" Brooke asked curiously.

"Hey Timothy... wake up buddy... I have another beer for you," Sam snickered as he tapped him lightly in the cheeks.

"A beer," Timothy mumbled.

Lisa found an almost full bottle of beer and put it to Timothy's lips, he tilted his head back, and took a small sip; he was still wasted.

"We're going to make your fantasies come true," Brooke told him.

"Re... lee... wee," Timothy mumbled.

"Yes, we're going to dress you up like a girl and the boys are going to fuck your brains out just like you wanted," she giggled.

"O... kay," Timothy laughed.

"He's totally out of it," Sam laughed.

"Ok, let's start dressing him.

"Here, I found a pink chastity for his cock," Lisa laughed.

"What the fuck?" Sam blurted.

"An old boyfriend, what can I say."

"I think that's all you Lisa," one of the girls stated.

"Here's the dress," Lisa handed over as Tiffany and Brooke put it on Timothy.

It went smoothly after that, his hair went into a bun, makeup and nail polish was next, and Lisa showed no mercy on Timothy's ass as she lubed him with the coconut oil.

"Mia, stop recording," Brooke ordered.

"What's up?" Mia asked.

"Okay guys, strip and use our strawberry, cherry, and melon flavored lipstick on your cocks; we want Timothy, I mean, Britney, to enjoy the process of sucking cock,"

Brooke ordered as the guys began to coat their coats with the transparent lip stick.

They moved away as two of the girls picked up the plastic tarp to hide any indication that they were still in Lisa's house.

Timothy was on his knees and his eyes were somewhat open as they began to film.

Everyone else that had free hands decided to join in on the filming but made sure not to cross paths that would block anyone's shot.

"Hey Timothy, are you ready for your sexual fantasy to begin?" Brooke asked as she would do all of the talking to Timothy, or should we say, Britney.

Timothy shook his head though he had no clue to what he was agreeing to.

"Do we have your permission to record your first sexual fantasy that you begged us to help you out with tonight?"

Again, Timothy shook his head.

"You wanted your girl name to be Britney; is that correct?"

Once again Timothy shook his head.

"Here comes your first cock so open wide."

Lenny stepped into the picture and placed his strawberry flavored cock into

Timothy's open mouth.

"Mmm," Timothy moaned as the taste of strawberries burst into his dehydrated mouth.

"Close your lips around his cock and make love to it."

"Mmm," Timothy moaned savoring the strawberry taste.

"Look up at me while you're sucking my cock slut," Lenny commanded disguising his voice.

Timothy sucked his cock as he peered up at Lenny.

"Good job Britney, is sucking cock everything you imagined?"

"Mmm," he nodded without letting Lenny's cock escape from his mouth.

"Just as you asked we locked you in your personal pink cock cage?"

"Mmm," Timothy nodded.

Lenny grabbed Timothy's bun so he could penetrate Timothy a little deeper.

"Britney, you're doing an excellent job, soon you're going to have a mouthful of cum like you always dreamed about."

"Mmm,"

"Ah," Lenny exhausted after fifteen minutes of pure pleasure.

"Swallow every drop Britney... just like you wanted... every drop."

"Mmm."

"Ah... ah... ah."

"Mmm."

"Ah, fuck, yeah," Lenny unloaded into Timothy's mouth.

"Mmm," Timothy did his best but couldn't handle the load Lenny just deposited and some ran down his chin and unto a small towel below him. Timothy sucked until Lenny had no more to give at the moment.

When Lenny pulled out Timothy looked a little disappointed.

Dan lifted the back of Timothy's dress and pressed his cock against Timothy's opening. Timothy looked back but didn't say a word.

"This is what you wanted isn't it; to suck cock and get fucked in the ass?"

In disbelief, Timothy nodded, was he totally fucked up from the alcohol or was it a deep desire.

"Ah," Timothy squealed as Danny pushed by Timothy's first defense.

"Britney, suck my cock," Sam demanded.

Timothy turned and took Sam's cock into his mouth.

"Mmm," he moaned as a new flavor hit his mouth.

Sam didn't waste any time and gave Timothy a little more cock than Lenny gave him and everyone was surprised that Timothy took it. They motioned amongst themselves that it must be the alcohol.

"Hum and look at me when you suck my cock," Sam demanded.

Timothy hummed and peered up at Sam.

Dan pushed a little harder as he pierced Timothy's second defense and slithered his way in.

"Ah!" Timothy let out loudly.

"Just what you always wanted Britney, a cock at both ends."

Timothy's ass was tight and Dan could feel the canal grip tight around his slippery cock. Dan now knew fucking Timothy would give him an intense orgasm and was getting excited. He fucked him slowly and would build up the pace in time.

Timothy moaned as Dan fucked him.

"Britney, are you enjoying your ass fucking?"

"Ah, ah, ah," Timothy muttered as he began to pay attention to the extreme pleasure of Dan's cock working his inner pleasure zone.

Sam grabbed Timothy's bun and began fucking Timothy's face as Timothy's cock sucking slowed down due to Dan's cock was deep in his virgin ass.

"Mmm, ah, mmm, ah," Timothy began to breath heavier.

"You're doing great Britney, hang in there, this is what you asked for, to be dressed like a maid and be treated like a whore."

"Are we giving you what you wanted Britney?"

He acknowledged a yes by a nod of his head though he was light years away from reality.

"Are you ready for another mouth full of cum?"

"Ah, ah, fuck yea, slut, ah, fuck," Sam let out as rope after rope filled Timothy's mouth.

"Open up and show the camera your mouth full of cum Britney."

Sam pulled out and Timothy surprisingly opened his mouth and showed the camera his mouth full of Sam's cum. Timothy did a good job holding Sam's cum in his mouth though some escaped and ran down his chin.

"Do you enjoy having a cock explode into your mouth?"

Timothy nodded.

"Do you want to swallow all that cherry flavored cum?"

"Mmm," Timothy nodded.

"Permission granted, swallow and enjoy."

Timothy did just that, he swallowed, and then licked his lips giving the camera a false impression that he loved to suck cock.

Dan stopped, put his hands on Timothy's hips, and motioned Timothy to rock backwards. To everyone's surprise it worked , Timothy began to fuck Dan.

"You like having a cock in your ass?"

"Ah, ah, ah, mmm, ah, ah, ah," he moaned and looked behind him never acknowledging Brooke as droplets of cum dripped from caged cock.

"Faster slut, fuck me faster," Dan raged working Timothy's hips back and forth making Timothy look like a crazed sex maniac.

"Do you like getting your ass fucked hard and fast?" Lisa asked after another five minute interval.

"Uh- huh, ah... ah... ah... ah...ah" Timothy moaned as cum continued to form at the end of his caged cock.

"Fuck!" Dan exclaimed as he unloaded his manhood into Timothy.

"Britney, you fucking whore, you just love cock don't you?"

Dan pulled out and Lenny laid down behind Timothy.

"Britney, on your knees for me," Brooke stated as Lenny moved underneath Timothy.

"Good girl, now lower yourself slowly," Brooke directed as Lenny held his cock and aligned it until Timothy was impaling himself onto the hard stiff cock.

"Ah," Timothy as he seated himself onto Lenny's cock.

"Now bounce up and down for me slowly so you can get the ass fucking you deserve."

"Ah, hah, ah, ah, ah, ah, ah," Timothy continued moaning as he rode Lenny's cock.

Everyone looked in amazement to how Timothy was totally out of his mind but continued to fuck and suck cock.

Timothy continued to moan as in pleasure as Dan went to the bathroom to wash his cock.

"Ah, hah, ah, ah, ah, ah, ah," Timothy continued to moan in pleasure as he bounced with greater rhythm.

"Britney, would you like to suck on a third cock; a watermelon flavored cock?"

"Uh-huh," Timothy acknowledged.

Dan washed his cock and applied the watermelon flavored lipstick to his cock. He stepped over Lenny's legs and inserted his cock into Timothy's mouth.

"Mmm," Timothy reacted to a new flavor in his mouth. Though Timothy had swallowed two loads of cum his mouth was still dehydrated from the alcohol and welcomed the new flavor that set his mouth watering with saliva.

Timothy began to pay more attention Dan's cock than bouncing up and down on Lenny's cock so Lenny began to violently ram upward into Timothy's ass.

"Ahhh!" Timothy was near orgasm, he arched back, and pulled away from Dan leaving his cock stranded in mid-air.

"Slut, come back here and suck my fucking cock," Dan demanded.

Timothy's mouth was wide open from his moaning and Dan forced Timothy's mouth over his cock. Dan held onto Timothy's bun as he forced Timothy to take his cock deep into his throat. Dan was relentless and only let up a few times for Timothy to breath.

"Ahhh, ahhh, ha, ha, ha," Timothy moaned as his body enjoyed a second orgasm along with Lenny as he got a facial from Dan.

Sam was up next to fuck Timothy's ass; once Dan and Lenny were clear Sam motioned Timothy onto his back. He easily pinned Timothy's legs back to his ears, slid his cock into Timothy, and began hammering him into oblivion.

Timothy screamed but not in pain but in ecstasy.

"Hang in there Britney."

"AH, AH, Ah," Ten minutes later Timothy moaned as he began to convulse into an orgasm. He shook violently as Sam relentlessly fucked him but could only ooze out a few drops of cum as he was completely empty from a night of fucking.