Amber stood nervously before the apartment door. She had just moved to Chicago from a small town in Indiana little less than a year ago and her new group of friends had been frequently telling her over the last few weeks that they had a tradition whenever someone in their group turned twenty one. They wouldn’t give any details and only laughed mischievously when she asked about it. Tonight was Amber’s twenty-first birthday, and even though she had her reservations about their intentions, she was arriving at her friend Shelby’s apartment that evening at 8 pm as requested.
As she waited for Shelby to answer, nervously chewing her full bottom lip, she caught sight of herself in one of the mirrors decorating the hall. Her big green eyes quickly scanned her 5’6″ frame. She was in good shape, she thought, her hands smoothing down her sides. Her 34C breasts were high and firm, her waist was narrow and her stomach was flat. Her ass sat high and firm atop long athletic legs. She tossed her long blonde hair and turned to the door as it opened.
The group of eight girls greeted her warmly as she entered the apartment, shoving a drink into her hand and relieving her of the bag of clothes she had brought with her. “You won’t need these. We already have an outfit for you,” one of them declared.
Amber was flattered and excited that they were going to dress her. She had always felt rather plain around her more worldly and glamorous friends. She had meant to buy some more sophisticated clothes but found the big city to be very expensive and hadn’t managed it quite yet.
Maybe tonight was going to be more like a coming out party for her, she thought. They were going to turn this country girl into a socialite. They ordered her into the shower.
After she had emerged from her shower wrapped in a towel, they pulled her into the bedroom, laughing. She was given another drink, which they encouraged her to down quickly. There was an excited tension in the room and Amber was coasting on the vibe.
Suddenly they pushed her down on the bed, holding down her arms and legs. Startled and a little frightened, she tried to get up, but they were holding her fast. Shelby pulled the towel open and the other girls spread her legs apart further.
“What are you doing?” she cried fearfully.
“Just relax,” Shelby said, gently petting the blonde hair of her pussy. She produced a can of shaving foam and a razor. “We’re just going to shave you, so no squirming,” she giggled.
To Amber’s amazement, she did just that. Shelby sprayed her pussy with foam and very gently and carefully shaved away every hair between her thighs. She watched with wonder as her pussy lips emerged from their covering, and having never been shaved before, she delighted in the cool air touching her bare flesh.
Her nervous laughter when Shelby was done was cut short though as she was quickly rolled over and again pinned down. Her towel was taken away entirely and her hips roughly pulled in the air.
“Now what?” Amber asked concerned.
“You’ll see,” they giggled.
Again Shelby was in charge and she felt the older girl gently caressing her ass. What the hell is going on, Amber thought, scared by this turn of events. Shelby gently pulled her ass cheeks apart. “Such a tight little asshole,” she murmured stroking her rosebud.
Amber jolted as something cold was squirted onto her asshole. “What are you doing?” she cried out, getting genuinely concerned.
The girls only laughed as she felt something pressing at her asshole. “No,” she cried.
“Yes,” the replied in unison as the dildo pushed its way into her ass. Shelby was slow and gentle and Amber experienced only a minimum of pain as the toy was pushed all the way into her ass. Shelby began to gently pump it in and out of her and Amber found that she was enjoying her first anal penetration.
Amber groaned with pleasure and the girls all laughed. “Feels good, doesn’t it?” Shelby asked, increasing the speed.
“Oh yes,” Amber breathed, feeling an orgasm building. Before it could peak the dildo was pulled out of her ass.
“No,” she groaned, which brought another fit of laughter out of the girls.
More lube was squirted onto her asshole and she again felt something pushing at her hole. She relaxed, glad that it was back, but gasped loudly as she realized that this was bigger, much bigger.
“That was just a little thing,” Shelby told her. “This is so much better. Now just relax and let it in,” she urged.
Amber tried to relax, but her reflexes kept wanting to expel the invading dildo. Finally, it was in and she lay gasping, waiting for the pleasure to replace the pain. Slowly the pain ebbed away and Shelby was sliding it in and out of her hole.
“Oh God, yes, that feels good,” she groaned, once again feeling the orgasm building. Is this the tradition when one of them turns twenty one, she wondered? They turn her onto anal sex?
Her orgasm was getting close when once again the dildo was removed. “Oh no! Don’t stop!” Amber said.
Shelby once again lubed up her ass and began to press in the dildo. “This is the final one,” she explained. “It’s six inches long and an inch and a quarter in diameter. And you’re going to wear it all night. Now just relax,” she said.
“It’s how big? All night?” she exclaimed as Shelby pushed the bigger dildo into her ass. Even though she was being gentle, Amber still cried out in pain as it penetrated her. Except for the tapered tip, the whole thing was thick, except at the very end where it again tapered down, so that her hole would grip it tightly, preventing it from slipping out. To her great surprise, she felt fingers in her pussy, rubbing her clit. The stimulation took her mind off the pain in her ass and her orgasm finally rushed forth, cum running down her thighs and soaking the hand rubbing her.
“Don’t worry, you’re going to feel so hot and sexy all night,” Shelby assured her, pushing the plug in to the hilt. Her hole closed around the narrow base, the long slender handle nestling between her cheeks.
“There, it’s in,” Shelby announced with satisfaction. “Now come on and we’ll do your hair and makeup.”
They released her and Amber rolled over and sat up gingerly, feeling the plug push into her ass. It still hurt a bit but in a good way. Accepting the robe Shelby offered her, she awkwardly walked to the bathroom, where the other girls were waiting for her.
Half an hour later, her hair was sleek and sexy and her makeup expertly done, her blue eyes looking more dazzling than ever before and her lips full and sexy. Shelby had been right about the plug, it felt amazing in her ass. She had never felt so hot and naughty.
The girls led her back into the bedroom where an outfit had been laid out for her. She stared with amazement at the garments on the bed. “I can’t wear that!” she exclaimed.
“Of course you can!” they cried, pulling the robe from her.
She stepped into the tiny thong that was offered at her ankles and it was pulled up her legs and settled over her freshly shaved pussy. She next stepped into a very low rise and very short pleated mini skirt. She stared at it with shock and dismay, knowing that when she walked the shifting pleats would reveal the curve of her ass with every step.
She pulled a tight halter top over her head, tugging it down over her full breasts. It was very low cut, revealing a lot of cleavage and barely covered the bottom curve of her tits. As there was no bra to be worn with it, and the fabric was rather thin, her hard nipples were clearly evident beneath the clinging fabric. Her breasts also jiggled freely in the top and she was going to have to be careful she didn’t fall out of it.
She slid her feet into the high heeled sandals and stared at her reflection. “Oh my god,” she gasped.
“You look so hot.” the girls complimented. “You are going to have so many guys after you tonight.!” they said.
They went to a hot new club and, of course, did not have to wait in line. Even though her friends were dressed in similarly sexy and revealing outfits, she was very self conscious in the short skirt, knowing she was flashing her ass with ever step, and she immediately headed for the shooter bar, hoping for a little help in overcoming her inhibitions.
The male contingent of her group of friends were already at the club, knowing it was her twenty first birthday and also knowing of the tradition. As she headed for the bar, Rich was right behind her, pressing up against her.
“Hey Amber, you’re looking pretty hot tonight,” he whispered in her ear. “Let me get this drink for you,” he offered, reaching for his wallet.
“Not so fast, mister,” Shelby interjected, putting her hand on his arm. She pushed her way between the two of them and faced Amber.
“There are four rules tonight, honey. Number one, if a guy buys you a drink you must repay him with an open mouth kiss, tongue and all. Second, all of the guys in our group are allowed to squeeze and fondle your ass all night. Three, have a good time but don’t get too drunk. I’ll tell you the fourth one later, and until then, think about who you accept drinks from,” she said glancing at Rich. With a smile she gave Amber a pat on the ass and left the two of them.
“So, will you let me buy you that drink?” Rich asked, squeezing her ass under the short skirt. “Rich, people can see my ass when you do that,” she hissed, pushing his hand away.
“I know,” he whispered in her ear, laughter tingeing his voice. “Drink your shooter,” he instructed, not removing his hand from her butt.
After a few drinks and very hot kisses, she didn’t mind if either Rich or any of the other guys pushed up her skirt and she even spun about on the dance floor with them. Lots of guys were leering at her all night in her short skirt and revealing top, but her male friends were very protective of her and she didn’t encounter any trouble.
At one point, she was kissing Doug for a drink as his hand slid beneath her skirt. Since all the guys knew of the tradition, his hand didn’t go for a squeeze of her cheeks, instead it went for the plug in her ass. He gave it a hard jiggle, causing her to cry out and step away from him, her cheeks reddening with embarrassment.
“Don’t worry, baby. We all know about the plug,” he laughed, pulling her close.
“You do? All of you?” she asked, her eyes wide.
“Yes. Has Shelby told you about rule four yet?” he asked, his green eyes sparkling.
“Um no, not yet,” she replied.
He turned her so that he was behind and gripping her hips, pulled her tight to him, grinding his hips against her ass. “Go and ask her,” he whispered in her ear.
She made her way to Shelby, who was having her own ass squeezed and stroked and in a low voice asked, “Tell me about rule four.”
With a wide smile, she pulled Amber aside. Rule four is that at the end of the night you decide which of the guys in our group you want to replace the plug in your ass with their dick. And you do have to pick one, or else I’ll pick one for you.
Amber stared at her wide eyed. She then slowly turned and scanned the club, picking out her friends amongst them. “Who would you pick for me?” she asked, not taking her eyes off the crowd.
“I think Rich might be a good choice. He’s well hung and very experienced in anal. So is Brock, but he loves to spank as well, so you have to be into that. Doug is also good, well hung but not as experienced. Which can be good, he’s very enthusiastic. I wouldn’t go for Terry, he’s also hung but selfish in bed. So, either Rich or Doug.” To Amber’s great surprise she felt Shelby’s hand slide beneath her skirt, caressing and squeezing her ass. “Of course, there’s always the more unconventional choice of one of us girls doing you with a strap-on.” Her hand slid further between her thighs, caressing her pussy through the soaked thong.
Amber turned to stare at Shelby and the older girl took the opportunity and lowering her head, pressed her lips against Amber’s. Her blue eyes flew open and she could only stand stunned as Shelby’s hand sought out and tweaked a pert nipple.
Amber stammered, “Thanks for explaining rule four. I’ll think about it.” Stumbling away, she couldn’t believe Shelby had hit on her. She had never had a girl touch her sexually before. She now viewed the earlier part of the evening in an entirely different light.
She found her way to the bar and Doug paid for her drink. As their lips met in a long and hot kiss, she decided he would be the one. He was 6″3″ and even in her high heels he still stood four inches taller than she. His tousled curly brown hair and green eyes gave him a boyish quality but his strong and lean body was all man.
“I want you to be my rule four,” she told him shyly.
His full lips broke into a wide smile and he hugged her tightly. “Baby, you won’t be sorry,” he promised before his lips claimed hers again in a kiss that took her breath away.
“Hey, my turn to buy her a drink,” she heard Rich saying.
“Don’t waste your time, man. She picked me,” Doug bragged.
“No way!” Rich exclaimed, clearly disappointed. “Damn.” Pulling her close, he wrapped his arms around her, caressing her ass with both hands. “C’mon baby, you don’t want him. I’ve got lots more experience, you should pick me,” he said in a low voice, causing a shiver to run down her spine.
Staring up through the black hair that hung over his dark blue eyes, she wondered if maybe he might not be a better choice. His hands on her ass were making it difficult to think. No, she wanted Doug to be her first. “Maybe some other time,” she said.
Giving her ass a final squeeze, he replied, “I’m going to hold you to that.”
“You better,” she flirted back.
She said her goodbyes and she and Doug left the club, heading for Doug’s apartment. They tumbled into the cab and kissed for the entire ride.
By the time they entered the elevator in his building they were both so turned on they couldn’t wait another moment. He pressed her against the wall and pushed up her top, revealing her full breasts. He smiled appreciatively before capturing a nipple in his mouth. Amber groaned softly as he sucked and nibbled the sensitive nub, while his hand squeezed her other breast. She held his head to her while his other hand slid down between her thighs, rubbing against her wet thong.
The doors to the elevator opened and not bothering to pull down her top, Doug guided her down the hallway. As soon as he had closed the door behind them, she dropped to her knees and began tugging on his belt.
“Hold on baby,” he said, placing his hand over hers, stopping her. “Take off your top and skirt first,” he continued in response to her questioning gaze. “I want you in only that naughty little thong and those hot shoes,” he finished with wicked smile.
Matching his smile, she slowly pulled the tight top off and shimmied out of the tiny skirt. He pulled off his own shirt as he watched her strip. Pressing herself against him, she tipped her head back and flicked her tongue over his lips before sliding down his body, leaving wet kisses behind as she again knelt before him.
Slowly, she undid his belt buckle and tugged open the button of his jeans before sliding the zipper down. Tugging down his boxers along with his jeans, she pulled them until his cock sprang free, hard and thick, bobbing in front of her face.
With an appreciative moan, she wrapped her hand around it, guiding it towards her mouth. She may have never had anal sex before, but a blowjob was something she knew how to do and Doug was not disappointed.
He stared with amazement as she began sliding his cock into her mouth, pumping him in and out slowly until she was deep throating him, her nose pressed against him. He groaned loudly as she began sucking him harder and faster until he grabbed her thick blonde hair in his fist and holding her still, set his own pace. He fucked her mouth and throat steadily, and then with greater urgency as he felt his orgasm building.
With a cry bordering on pain, he came forcefully, shooting his cum into her mouth. Amber sucked greedily, swallowing every drop and milking him dry. His cock went limp in her mouth but she kept sucking on him, flicking her tongue over the head until he began to stiffen and was again hard.
Doug was leaning against his front door, staring down at her in amazement. “Hot damn, you’re good.” he said, before extending his hand to help her up.
He pulled her to him for a deep kiss, tasting himself on her tongue, as they stumbled into the bedroom. Amber lay back on the bed as he slowly pulled her thong off, sliding it down her long legs and over the shoes still on her feet. “Leave these on,” he whispered, caressing the high heeled sandals, before he dipped his head between her thighs.
She sighed happily as his tongue pushed between the lips of her pussy. “I love a shaved pussy,” he groaned. She was sopping wet and Doug hungrily lapped up her juices. Sucking on her clit he added his fingers, plunging them inside her.
Her back arched up off the bed as he ate her pussy, her orgasm building in the pit of her stomach. As he continued to finger fuck her and suckle her pussy, his other hand slid beneath her and gripping the plug in her ass, he wiggled it, sending her over the edge. Crying out loudly, she gripped his head with her hands, grinding his face into her quivering cunt.
As her trembling subsided, Doug began to slowly kiss his way up her body, over her smooth stomach and ribs. He roughly pinched an already erect nipple between his fingers as his mouth closed over the other, sucking hard, his teeth nipping at the hard nub. She cried out softly at the rougher treatment, surprised at the surge of wetness in her pussy. “Oh yes,” she breathed, her back arching up off the bed, pushing her tits into his face.
He squeezed her breasts hard, his teeth nipping harder at the nipple in his mouth. She gasped at the delightful pain that rippled through her body and moaned softly in appreciation. Lifting his head, he continued to squeeze her breasts roughly in his large hands, his thick fingers twisting the nipples until she cried out.
Gasping loudly, she watched in surprise as he slapped her breasts, seeing the firm flesh jiggle and turn red under his assault. Again his head dipped down and sucked on a nipple while he continued to twist the other. “Oh, God, stop, please stop,” she begged when she could take no more of the exquisite punishment.
Raising his head, he flashed her a wicked smile. “Roll over,” he ordered in a seductive whisper. “On your knees, head down.”
Nervously she did as he told her, pushing her ass in the air. Suddenly scared, she gripped a pillow tightly as he nudged her knees wide apart.
“Are you ready?” he asked, his voice turning gentle.
“Yes,” she replied in a small voice. She couldn’t believe she was doing this. Before tonight there is no way she could imagine herself willing to have anal sex. Especially not with someone who wasn’t even her boyfriend. But spending the last few hours with a plug up her ass in such a sexually charged atmosphere had changed her mind and she was more than willing to go for it.
“Here we go,” Doug told her as he slowly pulled the plug from her ass. Her breath hissed through her teeth as it slid out of her and then she suddenly felt empty.
A disappointed sound slid through her lips and he chuckled behind her. “Don’t worry. You’ll be full again in just a minute baby,” he assured her.
His comment was followed by lube being squirted into and outside her asshole. Her hole was slightly gaping and Doug was thoroughly coating her and himself. He knelt behind her and aiming his cock at her virgin hole, he slowly began to press in.
Amber tried to relax, to let him in. His head pushed in, causing her to cry out loudly. She recalled how big he was when she blew him moments before and was surprised that he had that inside her. After a moment he pushed in further causing her to bury her face in the pillow she was clutching, muffling her cries of pain. She didn’t tell him to stop though, she wanted this. She was determined to go through with it. It had to get better.
He again waited for her to adjust before pushing in further. Eventually his balls slapped against her dripping pussy and he groaned loudly, loving the feel of his cock deep inside a newly deflowered ass. “Oh yeah, baby, your ass feels so good.” he groaned.
Slowly he pulled back and then pushed back in, working up a slow and steady rhythm. “So sweet, so tight,” he murmured, fucking her gently.
Amber lay beneath him, her eyes filled with tears that threatened to spill, biting her lip waiting for the pain to subside and the pleasure to begin. Slowly, it happened, the pain ebbing away, being replaced by the hottest, naughtiest feelings she had ever experienced. Pushing her ass back at Doug she pulled him even deeper inside her. “Oh yeah, give it to me baby. Fuck my ass, fuck it good and hard,” she pleaded, having a sudden desire to have him ramming into her.
Seeing that she was finally enjoying it, he eagerly complied, and drove his cock deeply into her, thrusting in and out quickly. “Feels good, doesn’t it baby?” he chuckled. “Yeah, feels so good fucking your virgin ass, so good.”
She gasped at the intense pleasure of it, feeling an orgasm unlike any she had ever had before beginning to build. “Oh God, oh God. Oh, yes, yes, yes!” she cried. She again buried her face in the pillow, this time to muffle her cries as an incredible orgasm tore through her, causing her ass to clench tightly around Doug’s cock.
“Oh yes, Doug, fuck me, fuck my tight little asshole” she said, surprised by her own dirty talk.
It took an immense amount of self control to keep his own climax at bay as she shuddered beneath him, her ass squeezing his dick as more orgasms followed the first. Doug kept up a steady pace of fucking her, plowing in deep, delighting in her cries of ecstasy. He pulled her cheeks apart, watching his thick cock plundering her ass, her stretched hole clutching him tightly.
“Your ass is so hot, I love watching my cock fucking you. Your sweet little asshole is stretched so wide,” he laughed, dipping his thumbs down to his cock, spreading her hole even wider.
“Oh God, Doug, please cum, I can’t take much more,” she finally pleaded as the orgasms continued to explode within her.
“Fuck yes, oh fuck, yes!” he roared, grinding into her, plunging in even deeper as he allowed his own climax to overtake him.
His twitching cock spewed forth a huge load of cum deep into her ass before he finally collapsed onto Amber’s back, flattening her.
They lay like that for a few minutes, trying to catch their breath and calm their racing pulses.
“Oh my God, Doug. That was incredible,” she finally gasped. “I had no idea anal could be so amazing.”
He slowly sat up and pulled his now limp cock from her ass. Pulling apart her cheeks, he stared in awe at her gaping hole as a glob of his cum slipped out. “Well, you were pretty incredible yourself,” he whispered to her, laying down, pulling her close. “Happy birthday, Amber,” he murmured before drifting off to sleep.
The next weekend found her again at the club in another revealing outfit with a butt plug of her own up her ass. This time her attentions were firmly directed towards Rich. She had been fantasizing about him fucking her back door all week and she was looking forward to getting back to his place.
Who knows, she thought as she spun about the dance floor, flashing her ass to everyone, maybe she might even give Shelby and her strap on a try one night.