Pain in the Ass

“So you don’t think you could handle it then?” Kevin laughed
“Well I…I just think it would hurt too much” Ellie giggled.
“Haha; well it is mainly for the guy but a lot of girls find it kinky” he replied
“Sounds like a man talking from experience” she teased him
“Yeah well I’m sure you already know but it is a favorite of mine” Kevin said
“How would I know?” Ellie
“You and Mandy are best friends. Do you really think I am to believe that she hasn’t told you about what her and her boyfriend are doing in the room next door?” he laughed.
Ellie looked down, blushing a heavy pink color. “I think you are just being a pussy” Kevin challenged.
“It’s not like I have anyone to try it with anyways. None of my old boyfriends tried to get me to do it so I never really had a reason to. For now I think I’ll just keep things outta my ass, thank you!” Ellie chirped.
“Suit yourself. Let me go see if Amanda is ready” Kevin said getting off the couch and opening her door. The way she slept made him smile/ She was always so calm and peaceful with a tiny smile on her face. Amanda stirred when she heard the door open and opened her eyes slightly.
“Hey baby,” she yawned
“Hey you, it’s getting late we better get going. How was your nap” He asked stroking her hair
“Mmm wonderful, but I’m still tired” she smiled
“I know, but you’ll feel better after we get going” Kevin reassured her. He left her bed and went back into the living room where Ellie was waiting.
“She’ll be right out.” Kevin announced “I’m going to bring the car around front”
Kevin threw on his pea coat and meandered down the steps of their lofty New York apartment building. He reached the sidewalk and fished a cigarette out of the pouch in his pocket. He sucked a long drag through his chest as he tore through the light flurries of a December New York evening. Once he pulled the car up to the building, the girls were already waiting outside. Surprising he thought. Normally they left thirty minutes later than when he wanted to go.
“Shit!” Ellie shouted “I forgot to grab cash at the bank. I hate paying with my credit card. My dad always says I spend too much and I have to hear about it every time I ask him for money.”
“I asked you earlier on the way back from class if you wanted me to stop and you said no” Kevin lectured her before smiling at her in the rearview mirror.
“I got you covered.” Amanda smiled, turning around from the passenger seat.
“Thanks Mandy, at least somebody looks out for me.” Ellie teased
“Hey I resent that” Kevin protested
“I’m just kidding, you know I love ya. Even though you really are a pain in my ass” Ellie said
They pulled into the parking lot of DeCarlos and Kevin lead the girls inside to the lobby. The ma?e d’ sat them at a circular booth in the corner of the restaurant. Kevin sat in the middle with the girls on either side of him, a pretty typical seating arrangement for the group. After they put in their order and got drinks, Kevin proposed a toast.
“To grad school, student teaching and the last few weeks at school.”
“Hear hear!” Amanda bellowed, clinking her glass against his and Ellies.” “So who’s the lucky guy you’ve been texting all week.” she began turning to Ellie.
“And how do you know it’s a guy?” she blushed again. Kevin grew silent. He never liked the idea of Ellie with another guy but himself. Even though they hadn’t ever hooked up and he had a girlfriend, he kind of felt attached to her and like she was his. He kept his dismay mostly quiet however and always fabricated some fake reason for why she didn’t like each of her boyfriends.
“Oh please! You wouldn’t be so attatched to that phone if it weren’t some new crush.”
“Shut your face Mandy” Ellie laughed “It’s no one important, just an old friend from home.”
After the meal they all felt like drinking more. Kevin bought a case of beer for Ellie and himself and a girly berry flavored pack for Amanda. They burst into the apartment and the girls went into the bathroom giggling. Kevin poured a beer into two glasses and opened a cherry malt beer for Amanda.
“Ooh let me have that,” Ellie begged when she came out. He handed her the glass and she took a large gulp. They drank together for over an hour laughing and talking about school, friends and past experiences.
“Why don’t we play Texas Hold-em” and make it interesting.” Kevin suggested
“I already told you I don’t have any cash” Ellie stammered.
“Not that kind of interesting. No chips, no money, no problem-” he hinted, leaning his head in with that devilish grin.
“Haha what?!!” Ellie gasped looking at Amanda for a clue as to how to react.
“I think it sounds like fun.” Amanda revealed sipping her fruit loop syrup. Kevin shot her a surprising ‘-are-you-sure?’ glance. She just giggled and kept drinking. He could tell she was drunk. She never laughed this much unless she was drinking.
“Ok what exactly are the stakes?” Ellie implored nervously. “what would I have to do?”
“Here’s what I’m thinking.” Kevin went on. “I’ll deal and you two play against the dealer. When I win the hand, you too remove a piece of clothing. When I lose the hand, I will. Sound good?”
“Let’s do it!” Amanda said “I’ll get us more beers”
“Alright I suppose” Ellie shrugged “Why not?”
The first couple of hands went very badly for Kevin. Ellie kept a calm face through the first hands only to get a full house on the turn card followed by a two pair queens and kings. Beginner’s luck he thought. No way can they keep this up. He was wrong. Amanda’s string of luck brought Kevin all the way down to his boxers. The girls giggled and made jokes about how he was getting cold being just in his boxers. Then Kevin got a fantastic idea. Neither of the girls knew that he had gone to summer camp his whole childhood and if there’s one thing you learn how to do at camp its handle a deck of cards. I’ll cheat he thought, and wager something incredible.
“Ha-ha” he mocked them, “I say we make this even more interesting. If I win..”
“If you win!?” Ellie interrupted. “We’re fully clothed and you are one bad deal away from rocking your birthday suit.” Both girls started laughing.
“Hear me out. If I win I get anal sex, if you guys win…well what do you want?” He tempted
“I’ll leave that to you.” Ellie stated “Since you are the one taking the punishment”
“Actually, I was talking about you Ellie” Kevin revealed starring right into his girlfriend’s weary eyes. A moment of silence and hesitation passed before Amanda responded.
“Ok, but if we win and you have to go to a party tomorrow night in a dress, high heels, and with full make up. You have to introduce yourself as Kayla and talk in a girly voice. It that ok with you Ells?”
“I guess, but what if he wins?” She wondered nervously
“If he wins then I’m ok with it if you are willing, but he won’t. Look at our odds.” Amanda reassured
“Bring it on.” Ellie challenged him
“Here we go” Kevin said as her dealt the cards. First hand out of the gate he dealt himself three kings from the bottom of the deck and manipulated two fives in the flop. The girls pulled their sweaters off with no hesitation and awaited the next hand. Kevin managed to deal himself a four card straight and stick the ten he needed into the river card. The girls went down to their bras and giggled. Kevin won two more hands in a flash. The girls sat topless in their panties looking very worried.
“You are gonna be so tight.” Kevin winked at Ellie who remained silent feeling helpless.
“Just deal!” Amanda barked.
“Haha. You mad Mandy? Looks like my luck has finally turned around” He smiled laying down the flop cards. He dealt himself three aces and looked at the girls who were studying their cards like finals week. Amanda looked pretty confident which made Kevin smile inside but he dealt the river anyways turning the fourth ace. Amanda laid down her full house and laughed until Kevin displayed his four ace wonder as both girls’ faces went white.
“Off come the panties” Kevin commanded “And let’s go to the bedroom shall we?” Amanda slid her panties off as she rubbed her friend’s shoulders consolingly. Ellie eventually slid her thong to the floor displaying her beautiful shaved pussy to Kevin and her friend. Kevin grinned in excitement. This was going to be good he thought. He walked into the bedroom and motioned for the girls to follow him.
“How do you want to do this?” He asked Ellie.
“Can’t I just give you a blow job?” Ellie begged “It’s going to hurt so bad. Please?”
“A deal’s a deal. I want that sweet ass.”
“Ugh” Ellie whimpered looking pleadingly at her friend who just looked down.
“Alright I’ll decide. Lay on your stomach with that tight little ass in the air.” He instructed. Slowly but surely she moved to the bed and lay before him, exposed, delicate and scared.
“Relax and might actually en-”
“Aren’t you going to use any lube Kev?” Amanda interrupted
“Go get it out of the drawer and squirt some on your friends virgin ass crack for me”
Amanda walked over to the nightstand and opened the drawer beside the bed taking out the warming lube that they had used so many times before. She walked over to Ellie on the bed and let out a deep breath before opened the bottle and squirting it onto her ass.
“Oooh its cold!” Ellie cried out. Amanda leaned down to her and kissed her head after whispering into her ear.
“I’m sorry; it’s going to be okay. I love you.”
“Alright alright enough of the nonsense” Kevin shooed Amanda away. “I need to get harder first. Amanda suck my cock for a while.” She dropped to her knees obediently as she had done earlier that morning and sucked his cock with expert concentration using her lips as a tight ring. Her tongue swirled over the head as she made a loud popping noise whenever it came out. Ellie watched carefully from her subservient position and felt herself getting moist from the sight before her eyes. She had always been turned on when she could hear their bed squeak through the wall but had never gotten to see any of the action up close. She slipped her hand underneath her body to rub her aching pussy and get some much needed pleasure from her current predicament. After Kevin was sufficiently excited he pulled his rock hard cock from Amanda’s willing move and knelt above Ellie’s waiting asshole.
“I’ll be gentle at first Ells” He reassured her “I want you to enjoy this as much as I’m going to”
He lowered his cock between her firm white cheeks and prodded them apart excitedly. When his cock head touched her forbidden hole she shuddered and clenched herself tightly in protest from his invading member.
“Don’t tense up” He encouraged her “Its only gonna make it worse going in”
“Yeah Ells, just let it happen and try and relax. Touching yourself helps at first.” Amanda suggested
Kevin pushed his cock head gently at her tight hole which refused to give at all. He reached down and spread her soft, delicate cheeks apart making it easier for his cock to slip in. He pushed again and this time the head started to slowly slide in and he felt her ass expanding and her subsequent clenching down his cockhead.
“Owww” Ellie moaned. It felt like a fire was splitting her backside in two as her friend pushed his cock further into her. He had about three inches in now and was really starting to enjoy the feel of her hot little ass clenching his cock. The lube was warming him and he felt a growing sensation coming from his cock.
“I’ve wanted to do this for so long.” Kevin moaned thrusting back and forth for several minutes into her and looking at his girlfriend on the chair across the room. She had her legs spread wide and she was furiously rubbing her soft little shaved pussy moaning while watching her boyfriend fucking her friend up the ass. He could tell this was really turning her on and smiled. He pulled his cock almost all the way out and felt Ellie’s body relax only for a second before he shoved almost his entire length back into her tight little asshole.
“OWWW” She screamed and he watched her face contort and spasm with the newfound pain of anal sex. She was obviously enjoying it though because her hand was rubbing her wet pussy and between strokes a stifled moan would creepy from her sexy lips. Kevin was thrusting really deep now and he was kneading the flesh of her ass checks as he buried his cock into her body.
“Mandy come here” He ordered as she excitedly hopped out of the chair and came before them on the bed. “Kiss her.” She leaned towards her friend at the top of the bed whose face look like an enduring struggle between pleasure and pain. Her lips came to Ellie’s and they began to share a soft kiss as they rocked back and forth with the force of Kevin fucking Ellie up her tight little ass. Their closed lipped kiss soon turned into a full blown make out session as Amanda held Ellie’s head in her hands and forced her lively tongue into Ellie’s waiting mouth. Ellie was doing all she could to keep from screaming at the top of her lungs. It felt as if someone was forcing a fire poker into the depths of her ass and he was trying to stretch her until she bled. She was close to making herself cum however and Kevin sensed this as he thrust harder and harder kissing her back as he did.
“I’m gonna cum soon, babe.” he moaned
“Ohhh! Ohhhhhhh! Do it! Spray your hot cum deep in my ass.” Ellie yelled out.
Amanda fell to the floor beneath his legs and began furiously licking his balls while he thrust into her friend.
“OOOHH OOHH” he shouted, flooding deep inside her with his warm cum. Her face quivered and moaned as she came down from her orgasm. Kevin collapsed onto the bed. Ellie ran to the bathroom before coming back to lie on Kevin’s left side holding him while Mandy clang to his right. They began to drift off to sleep and right before Kevin was asleep Mandy whispered into his ear
“I knew you were dealing from the bottom” as she kissed him and the three of them slept naked on top of Amanda’s sheets together.

Please leave comments and ratings. Considering using these characters in a possible sequel or related story.