Olivias Downtown Adventure

Olivia scurried nervously down the pot-holed street of the poor, downtown neighborhood of the city. Having grown up in the wealthy suburbs, she had only visited this part of town once or twice in her life. She recalled coming down here with her father on one of his business errands a couple years back. As she breathed in the hot night air, she recalled from that earlier trip the same sweet, slightly rotten smell of the city in the summer.

Being downtown by herself on a Friday night was something she had been warned against -- her parents would absolutely flip if they found out! But, truth be told, right now she was mostly just feeling excited at the adventure of it. She was 18 years old now -- definitely capable of looking out for herself. Right?

This summer was turning out to be -- by far -- the most fun of her life. She had just graduated from high school the spring before, and with her plans set for college the next fall, her parents had finally eased up a bit on their overbearing control of her social life. When she told her mother earlier this evening that she was going to a birthday party at her friend Beth's and would probably sleep over there, her mother barely even put up a fight!

"Well, I suppose you'll be off on your own next year anyway, and you'll have to start taking responsibility for yourself sooner or later." When she got to the party her friends decided they wanted to buy Beth a gag birthday gift -- a large dildo! The problem was that the only place you could get something like that was at an adult bookstore down in the seedy part of the city. They drew straws to see who would make the shopping trip -- and Olivia had lost.

A couple of her closest friends were particularly amused that Olivia, of all people, had drawn the short straw. Throughout high school, Olivia -- amongst all her friends -- had been the one most concerned with modesty. She wouldn't be caught dead wearing one of those revealing tops or thong underwear that some of her other friends would put on. Not that Olivia's body was anything to hide -- in the last couple years it had sprouted in all the right places, a fact that had not gone unnoticed by the boys in her class -- despite her slightly more conservative clothing choices.

Olivia had beautiful pale skin, slightly flushed this evening with the warm night air, full blond hair pulled back into a ponytail that flowed down her back, slender legs, round hips, and perky yet full breasts that -- more and more -- were jutting out for all the world to see. This evening she had decided to wear a sleeveless white and yellow sundress -- the perfect thing for a warm evening like this. When she had first arrived at the party she was hot and sweaty from the walk over and, in a moment of spontaneous summer freedom, she had decided to take off her bra! It felt so much better to have her breasts freed from that restrictive garment, cool underneath the light cotton fabric of her dress. What would her mother say if she saw her now!

When she drew the straw that designated her as the person to buy the dildo, at first she balked. She had barely ever visited that part of town during the day, let alone at night and all by herself no less! But in a moment of self righteous pride she decided she was going to prove her friends wrong about her. They all saw her as Olivia the prude, Olivia the one who always played it safe, Olivia the virgin who wouldn't let her any boy past second base. Well she was going to show them! She could be just as confident and audacious as any of them!

Although most of her friends were in the dark about it -- the truth was that Olivia had found her own ways to experiment sexually. Olivia was just as intrigued by the changes her body had gone through as any of the boys. She loved taking off her clothes slowly, looking at herself in the mirror, and then lying down on her big fluffy bed and touching herself all over -- especially down there. She would fantasize about one of the boys in her class, James, a baseball player, and imagine that her fingers were his hard cock inside her.

Her sexual experience with real boys, however, was fairly limited. She loved making out with them of course, and would sometimes let them touch her breasts, but her pants always stayed on. Once -- only once -- a boy she was dating had begged her for a hand-job and she had consented. She had been absolutely fascinated with the soft, velvety, yet rigid cock he offered her, and the way he reacted when she touched it. Her memory of the boy's hard penis was now a permanent fixture of her masturbation fantasies.

So far, Olivia's plan to defy her friends' expectations was going well. She had ridden the subway downtown, and was now walking quickly through the heavy night air of the downtown neighborhood. She felt a certain thrill of independence! People were milling around, coming in and out of bars, shouting, laughing -- you could feel the festive Friday night spirit in the air. At one point she noticed that her sundress clad body had caught the eye of an unsavory looking character hanging out on the street corner. At that moment she regretted her earlier decision to take off her bra. But she just walked on by, pretending not to notice. And finally she arrived at the corner where the adult book store stood. The first thing she noticed was a neon sign in the front advertising: "XXX Videos, Gifts and Live Peep Shows".

"Live peep shows?" she thought to herself. She thought they just sold movies and sex toys here -- she didn't realize they had actual strippers too! Oh well -- this wouldn't be too difficult -- she would just go in, find the biggest dildo she could find, and get back to the party.

She entered the store and walked through rows and rows of magazine covers displaying all kinds of outrageously lewd sexual acts. And interspersed, in the rows of merchandise, were little doors with token slots. She guessed this was where you paid to sit in a booth and watch women in the back take off their clothes.

As she walked further into the shop (she was coming to realize it was quite big on the inside) a particular smell was getting stronger and stronger... A slightly acrid, sweaty smell -- like the combination of foot and body odor, with something else mixed in... an almost soapy, alkaline scent, not unlike her memory of the boy's cum she had produced with her hand-job. That must be it! The smell of male cum! She gave a little shudder at the lasciviousness of it all!

Although she was trying to stay focused on her task, she couldn't help but be pulled into looking at some of the images on the movie boxes surrounding her. She had glanced at her brother's Playboy magazines a couple times, but this was something completely different! Everywhere were pictures of naked female bodies being impaled by enormous cocks, giant breasts, spurting penises... The more she looked, the more fascinated she became. It was just so completely lewd and dirty! She had never been assaulted by so many grotesquely fascinating images before!

Involuntarily, she felt her body responding to the pictures all around her. A small, almost electric surge passed through her hips and traveled up to her breasts... She couldn't believe that places like this existed! In spite of her intentions to stay focused on finding a dildo, she found her mind wandering, picturing some of the scenes that might be going on right this very minute behind the closed doors of those peep booths. If she could only peep in on the peepers! To see them with their hard cocks out... see them staring lustily, licking their lips at actual women taking off their clothes in the back... Or dirtier still... What if she was the one back there and all those men in the rooms were staring at her own young body?

She felt that she went one step too far with that thought, so quickly she turned her attention back to the task at hand. She saw that the sex toys were in the back row of the store, so she walked in that direction.

Jimmy, the recently hired night manager of the shop, had been watching her since she first stepped into the store. How could he not notice! How many young, teenage blond girls came walking through these doors all by themselves on a Friday night? From the look of her clothes, not to mention the expression on her face -- she was definitely out of her element. Jimmy had been out of prison only a few weeks (about as long as Olivia had been a graduate of high school) and had only recently gotten this job through his brother's father-in-law. Although he had come out of prison with the intention of staying on the straight and narrow, the pathetic pay of this job had been so depressing that he had already hooked up with some of his old associates for a couple of burglary jobs. Life on the right side of the law just wasn't for him. Jimmy had only gotten laid once since he had gotten out of prison, and it wasn't even all that great -- just an ex-girlfriend that had looked a lot better before he'd gone into the joint.

In short, Jimmy was feeling just about as horny as a guy in his early thirties could feel on a hot summer night in the city. He was tall -- 6'2" -- and well muscled. Staying in shape was about the only productive thing he'd managed to do while in prison. He had actually just worked out earlier that afternoon, but hadn't had time to shower before arriving at his night shift. He stared at Olivia from behind as she walked down the aisle of the store. His eyes lustily traveled up her smooth, pale legs, to where her sundress covered her perfectly shaped behind. She was just about the sexiest piece of ass he'd laid eyes on in months! One way or another he was going to have that young, blond, teenage goddess... He had two friends working with him tonight that would help him make it happen too. He went out behind the store where Leo and Tom, two large black men, were smoking. He told them his plan.

Olivia had finally found her way to the selection of dildos. She couldn't believe how many there were to choose from! Finally, she saw one that would be perfect! It was a really big one, shaped just like a penis, colored black. Her friends would think this was such a hoot! Unfortunately it was on the top shelf, just out of reach... All of a sudden she heard a voice from behind her:

"Can I help you with that m'am?" At first she was startled -- she hadn't heard anyone come up from behind her.

"Yes... uh... well," she stammered. Jimmy could see how embarrassed she was at the fact that she had clearly been reaching up for that giant black dildo. He wondered how on earth someone like her -- clearly a wealthy uptown girl -- had found herself all alone in this place. She was here now -- that's all that really mattered to him at this point. He came and stood right behind her, almost touching her, easily reaching up for the dildo. She could feel the heat from his body and could smell the rich, pungent smell from his armpits as he reached up to the top shelf.

"Yes, oh thanks," she said. "It's actually a gag gift for a friend's birthday party!" She turned around to face him, but he hadn't stepped back from the shelf yet; he was still standing close -- too close actually -- right in front of her. He had dark eyes, a rugged, unshaven chin, and olive colored skin under his tank top... she guessed maybe Italian? Clearly not a bad looking guy... and his arms and shoulders were quite strong and developed actually. But wait, what exactly was going on here?

Jimmy smiled at her, and said, "Yes, it's always the friend people buy their dildos for, isn't it?" He took another step closer to her, backing her now into the corner of the store. He leaned in close to her holding the black dildo up to her face. In a taunting tone of voice, he said, "So I don't suppose this rather large instrument here, then, is going to go anywhere near your sweet pussy?"

She took a moment to register this comment before the inappropriateness of it dawned on her. Did he think he could come onto her this way? Well, good luck with that approach mister!

"Um, listen -- I just need to buy this and get back to my friend's party okay? Thanks for your help!" But when she tried to move towards the front of the store she found two rather powerful arms up on either side of her.

"You know, I have some other really great selections in the inventory room in back -- I think you should check them out before making your final decision. Don't you think you should look at your options?" he asked.

"No, that's really okay -- I need to go now."

"But I insist..." he said. And with that he pushed open a door behind her that she didn't even realize, until now, she had been leaning against. He placed his hands firmly around her hips and thrust her into a hidden backroom. It was a small, dank room with a mattress on the floor and a hallway connected to it from far side. She started to panic.

"We have SO many options back here! And the great thing is that back here you can actually try them out, so you know you're getting just the right one!" She started to panic -- a knot forming in the pit of her stomach. What on earth had she gotten herself into? Jimmy, on the other hand, knew exactly what she had gotten herself into.

"Leo and Tom!" he called out. "We're ready for you!" Two enormous black men emerged from the adjacent hallway. Tom was strong and muscular like Jimmy; Leo on the other hand was just plain overweight -- he looked like a gigantic bear of person. Each of them grabbed one of her arms and held her tight. Jimmy fastened a blindfold around her eyes. At first she tried to struggle and yell, but Jimmy quickly clamped a hand over her mouth.

"Now, being an uptight little rich bitch, you probably don't yet have a grasp of the situation you're in. So I'm going to take this opportunity to teach you. You have such a pretty little face -- I'd hate to mark it up." He lifted up the back of her sundress. "But this ass on this other hand... Wow, guys -- I think you'll agree! It's just begging for a little spanking. After all, how else is little miss uptown rich bitch going to understand that she has to do exactly what we tell her?"

At that point Leo forced her to lean forward over his knee while Tom pinned her in place with a gigantic hand on the small of her back and another holding her wrists. Jimmy already had her skirt up, exposing her girlish white and pink polka dot panties. He started by gently rubbing his rough palm over her perfectly shaped panty-clad ass. Leo and Tom watched intently. Olivia was totally helpless -- Tom had her arms pinned behind her while she was ignominiously shoved across Leo's lap. It was almost like when her father would spank her as a young girl! She felt Jimmy's warm hand caress her ass gently. Then, came the moment she was waiting for. Jimmy hooked his thumb under the waistband of her panties and slowly pulled them down -- bit by bit exposing the pale cheeks of her perfect ass.

"Okay -- my rich young slut -- now I'm going to teach you exactly what happens to girls that don't obey." With that Olivia felt a sudden flash of pain radiating from her buttocks. Jimmy's warm, open hand slapped her perfectly curved ass, once, twice, three times, four times, each slap ringing out lewdly in that back room. Olivia yelped with pain, but in the pause between each of the slaps, she also felt a different kind of heat radiating from her behind. She couldn't believe that her exposed body was trapped beneath the sweaty, muscular bodies of three strange men! The scene she pictured in her mind was positively mortifying... but also, strangely erotic? No! It wasn't erotic; what was she thinking! She was being undressed and spanked like a child -- utterly against her will! This was wrong and bad!

After her spanking they lifted her body up as if it weighed no more than a feather. They seemed to be carrying her someplace. Then they sat her on the edge of what seemed to be a padded table. She could feel Tom and Leo's strong hands controlling her every move. And she could smell the sweat of each of their bodies.

"Now, miss, do we understand what discipline means?" Her ass was still radiating with heat, her face deeply flushed with the humility of being spanked bare-handedly. She nodded. "Okay -- no more struggling and screaming, or else we'll just have to come back to that sweet ass of yours, and this time we won't be so friendly with it. I think it's time to explore a little more of what we've got here. Don't you think boys?" With Tom and Leo holding her in their grip, Jimmy proceeded to slowly unbutton the top of her sundress. Olivia whimpered quietly, but didn't scream anymore.

"Oh my, oh my! What do we have here! Looks like our little girl has decided not to wear a bra today! And she told us that dildo wasn't for her... That story is looking less and less likely now, isn't it!" With that he pulled the dress down just underneath her nipples - which popped out to greet Jimmy's hungry eyes. He bunched the sundress fabric up underneath her breasts, pushing them up and together. The nipples were smallish, red and hard, like miniature strawberries. He rubbed his rough thumb gently over one nipple, then the other, pushing them back and forth. Each time his thumb brushed over it, it popped up a little harder.

"I think little miss rich girl's breasts are enjoying this -- don't you think boys?" His hungry eyes stared at her erect nipple. "I think this nipple here wants a little kiss? What do think Miss? Does it want a kiss?"

"No!" Olivia shook her head. But a part of her was already questioning whether this was entirely true... What he was doing was -- to her horror -- starting to arouse her! With that, his mouth went down on her soft, exposed tit slowly, his lewd tongue swirling around the velvet breast until it found its destination -- that little pink, aroused nub of nipple-flesh. A surge of electricity passed from the tip of her breast, all the way through her body, down to her crotch. He sucked on the nipple more insistently now, feeling his cock stiffen in his jeans. Tom and Leo looked on hungrily.

Jimmy was now all but devouring these sweet, succulent tits -- he couldn't get enough. Oliva couldn't believe the waves of sensation pulsing through her body. She had expected Jimmy to be rough and insensitive and -- and while he certainly was aggressive, taking exactly what he wanted -- he clearly knew how to please a woman. It wasn't enough for him to use her body -- he was making her like it too. A surging electrical pulse seemed to be connecting her ravished breasts with her lower regions. Her hips started moving, grinding slowly on Leo's leg.

"Look at this little slut!" Jimmy said. "I think she's getting turned on! Leo, I think she's actually rubbing her pussy on your leg!" Olivia was mortified, and tried to stop herself from moving her hips, but the warm surges through her lower regions couldn't be denied. Jimmy was lavishing attention on her breasts like he was a starving man! The perfect, soft, firm globes of flesh were being pushed back and forth by his expert hands, tongue and mouth. It was driving her absolutely crazy, despite herself! "I think it's time for another look under that skirt, don't you think boys? This time from the other side!"

Leo got behind her and held her in place, while Jimmy pulled back one leg and Tom pulled back the other. Jimmy crouched between her legs, lifting her skirt and exposing her precious panty-covered crotch. "Oh boys, look at what we have here! I suspected we had a little slut on our hands, and now we have proof!" Olivia was mortified. Sure enough, a small wet spot had formed on the crotch of her panties, right over the base of her pussy. "I wonder what this sweet little pussy smells like?" And with that, Jimmy put his nose right up against that little wet spot on her panties, sniffing in her sweet, girl-like musk. "Oh lord I love the smell of a teenager's pussy!"