Anna Ch. 01

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Anna travels to Montreal to live out her fantasies.
3.5k words
4.47
34.8k
14

Part 1 of the 2 part series

Updated 09/22/2022
Created 01/08/2006
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Chapter 1: The XXX Cinema

Anna is the kind of girl who meets with success at every turn. Hailing from an upper middle class family, she never wanted for anything growing up, and her parents are proud of the independent, motivated woman she has become. At 22 years of age, she holds a good marketing job and is very popular with friends and family alike.

She is a bombshell too. Standing a little over 5'7", she has dark brown hair that cascades over her shoulders to the middle of her back, and big blue-green eyes that seem to gaze right through you if they catch you right. Her smile can only be described as high-wattage, and she lights up a room with it every chance she gets.

Even more outrageous is the body. Anna isn't a pale girl, but she doesn't worship the sun either. She is modest enough not to frequent the beach (a huge blow for the town's male population), and her girlfriends are always grateful to her for the lack of competition. On the odd days she does appear, it is always in the same blue bikini, which does a frustratingly good job of tucking away her glorious assets. The top is generous enough to completely cup her 36Cs, although the bottoms are thankfully cut high on the hips, giving a splendid view of her remaining 24-34 measurements.

Yet, despite her popularity and undeniable beauty, Anna has always been painfully shy with the boys. It never helped that her looks were intimidating enough to keep the boys at arm's length, and so while her girlfriends had their fill of sex, drugs and rock n' roll, Anna became something of a homebody.

But the lack of a boyfriend created a void in Anna's life, one that she quickly filled with steamy, taboo fantasies. She would spend time on the internet, scouring escort agency and erotic modeling sites wondering what it would be like to lead such a double existence. She dreamed of one-on-one encounters with strangers, where she could show herself off and reap the rewards. And finally, the fantasies became so powerful that she could no longer resist. She had to live them out.

Careful research and planning resulted in Anna buying a ticket to Montreal – a three hour flight from her hometown. It was easy to convince her family and friends of the trip's merits. Canada was an inexpensive destination, and she had never been north of the border. Clearly she needed a break, and the destination was very convenient. What family and friends wouldn't factor in was the city's thriving sex industry, which drew in Anna like a moth to a flame.

She arrived at her hotel on a cool afternoon in early October and checked in. Anna had lined up her fantasies, and had a number of adventures planned for her week of thrills. Tonight would be her only 'free' night, and she knew exactly what she would do with it. After grabbing a quick bite to eat, she returned to her room and changed into one of the many racy outfits she had brought with her. Before setting off, she stopped to admire herself in the mirror, and couldn't help smiling despite her nerves. She was dressed completely in black, with a tight skirt that stopped mid-thigh, and a sequined halter-top that strained to hold her breasts in place. A pair of 4 inch heels completed the ensemble, and with her hair down and makeup just so, Anna was stunning.

Throwing on a long overcoat, she left the hotel and walked slowly down St Catherine Street to a collection of neon signs marking the entrance to a XXX cinema. Heart thumping, she looked around with embarrassment, wondering what people would think to see her venture inside. Finally summoning up the courage, she quickly passed the signs and arrived at the top of a long flight of stairs leading down into darkness. She strained her ears but couldn't hear anything, and wondered if they were even open. "Come on!" she whispered to herself. She knew it was now or never, and she would never forgive herself for chickening out.

As she crept down the stairs, Anna began to make out the faint sounds of sexual ecstasy from below. The environment seemed strange, with the stairs reminiscent of a new office building, but as the lower level came into view there was clearly nothing white-collar about it. Four televisions hung from the ceiling with a different hardcore film playing on each. She moved quickly to the counter, where an elderly man stood and eyed her up and down.

"The private booths are cash only, or you buy a token for the two cinemas at the back" he said, feigning disinterest. Anna knew exactly what she wanted, and bought a token. It was expensive, but money was no object for her tonight. She turned, her cheeks flushed, and walked briskly along the hallway between the private booths. It seemed to wind along forever, and at one point she was startled by a booth occupier making a quick exit, his eyes avoiding her gaze. Finally she arrived at a turnstile that reached from floor to ceiling, comprised of heavy metal bars and a token receptacle on one side. Breathing hard, she inserted the coin and jumped as a loud clang indicated the metal grate unlocking.

Anna gave it a shove, and it reluctantly turned to allow her access. Despite a noticeable chill in the air, her palms were sweating. To her left and right were cinema entrance doors, and after a brief pause she decided to opt for cinema 'A'. Anna stood at the door for what seemed an eternity, before finally pushing it open and slinking inside.

The immediate and overpowering smell of cum was like a slap in the face, and it caught her by surprise. Her eyes adjusted quickly to the darkness, and she glanced around, feeling immediately awkward. The door had led her right into a central aisle dividing ten rows of plastic chairs, a third of which were occupied, and it placed her at the center of everyone's attention. Anna had expected to see couples but soon realized that she was the only woman in the room, and despite the acrobatic sex on the screen at the front, all eyes were on her. Panicked, she turned and pushed back through the door.

Once outside, she collected herself. This clearly was not what she had expected, and there was a clear danger as a lone female in heading back. She hoped that cinema 'B' would offer something different, but soon discovered a similar scene with even more men. Wrestling now between her common sense and her deeper urges, she finally decided to take the risk and revisit cinema 'A'. Pushing back through the door, she crept quietly down the aisle and found a seat, as twenty pairs of eyes sized her up.

Anna's feelings of uneasiness soon vanished as the action on the screen captivated her. A fairly average blonde was being pounded by three black men with impossibly huge cocks, and the expression on the blonde's face suggested she was not particularly happy about it. Anna felt herself getting wet. Getting her nerve up, she cast her eyes around the room, and saw that no one had moved. In the opposite section, she saw a man jerking off as the action heated up on-screen, and she was surprised at how openly he was doing it. She found herself staring at him, and her heart raced as she saw cum spurt from his cock onto the back of the chair in front of him.

Soon her eyes picked up many more men doing the same, and Anna found the idea of being in the same room with these men as they masturbated intense. One by one they came, some in dribbles and others in jets, before collecting themselves and leaving – only to be replaced by fresh faces. Anna, now completely at ease, rose a little from her chair and removed her overcoat. Settling back down, she looked back toward the screen, where the action now involved a blonde, a brunette and a black girl armed with dildos. She smiled as her fingers discreetly made their way under her skirt. Her bra and panties had never made it out of the hotel room, a thought that excited her no end.

As the lesbian action continued, Anna's fascination with her viewing companions again compelled her to look around. Across the aisle and behind her sat two men, one seat apart. One was jerking himself off as the other watched, and after a few minutes the active party came with a stifled cry before slumping back into his seat, Anna watched as he then adjusted himself and left, before she realized with embarrassment that the second man had been staring at her intently for some time. Anna quickly turned, her face burning, and went back to the scene on the screen. Moments later, her heart leaped into her throat as the staring man left his seat and moved down to her row, positioning himself three seats away.

His eyes began roaming all over her body, and she could feel the weight of his gaze despite keeping her eyes firmly on the screen. A feeling of panic began again in earnest as she saw him unzip his pants and pull them down to the floor. His uncircumcised cock now stood, fully erect, and he was simply gawking at her as he began moving his hand gently along its shaft. She could see out of the corner of her eye that he wasn't huge, but a good 6-7 inches were visible. He cleared his throat quietly, and she turned toward him with a weak smile. He smiled back, and his hand fell away from his cock, leaving it completely exposed. She resisted the temptation to look, instead turning her eyes back toward the screen.

After a few minutes, the man moved closer, so that now only one seat separated them. Anna shifted nervously in her chair. Her coat was pinned beneath her, and she desperately wanted it now as a means of covering herself up. As it was, her halter top rose about an inch over her nipples, leaving too much cleavage exposed, and her skirt had ridden up to her hips as she sat, meaning that her neatly trimmed public hair was hidden only by her now crossed legs. This outfit, she decided, was not the best idea after all.

Then Anna froze. The man had reached across, and his fingers were running gently up and down her upper arm. Her breathing became shallow and quick, and she focused her stare all the more on the screen in front of her. His light touch began working its way down to her lower arm, then her wrist, before he finally took her hand in his. She couldn't believe it as her hand, seemingly with a mind of its own, closed around his fingers. "This is it", she thought. "No going back now!"

His hand lifted hers, and moved it over to his waiting cock. For a moment she wouldn't let go, wanting to prolong the inevitable, but he grasped her wrist and placed her hand firmly on the lower portion of his shaft. She turned to size him up properly for the first time, realizing that he appeared to be of Middle Eastern descent, with a stocky build and swarthy features. His face was contorted into an expression of longing, and his eyes were fixed firmly on hers. She began slowly moving her hand up and down and he moaned, attracting the attention of two men nearby. Realizing what was happening, they moved from their seats into the row behind Anna to quietly watch the events unfold.

Anna's pace increased as she worked the man's cock, and he soon grasped her hand to slow her down. Her eyes, which were fixed upon his still swelling member, returned to his face and she smiled again. He did not return the smile, instead looking deliberately at her breasts and licking his lips. She was not surprised when his hands reached over and began to fondle them. She knew that she would not resist his advances, and so she allowed him to grope her as she continued masturbating him.

Again he moved, this time into the seat next to her, before reaching over and sliding the straps of her halter top from her shoulders. He yanked her top down, fully exposing her breasts and causing a collective sigh of delight from the two voyeurs seated behind. The man grabbed her right breast roughly and leaned in, taking her nipple in his mouth and sucking hard. Anna cried out as his teeth clamped down, sending shockwaves through her now trembling body. She closed her eyes as his left hand kneaded away, but they shot open again as she felt his right hand disappear under her skirt. He began coaxing her legs from the crossed position they were in, and finally she relented.

Anna was his, and she knew it. Her hand was pumping away at his penis, and she felt a few drops of pre-cum beginning to run between her fingers. He, meanwhile, was now moving his fingers through her public hair as he played with her clit. Then, as she knew he would, he pushed a finger inside her. He was not gentle about it, but she was so wet that she was able to cope with his clumsy movements. A second finger then entered, but she stopped him from using a third. Anna was relatively inexperienced and two fingers alone were enough to stretch her. He looked up at her, and his expression seemed even hungrier than before. Her vagina was insanely tight, and for him this was an unexpected bonus.

The man sat upright again, leaving her right breast covered in his saliva. He stared at her, saying nothing, before running his free hand through her mane of dark hair. Insistently he pulled her head towards him and began kissing her. She felt weak, and did not resist as his tongue entered her mouth, probing for hers. For several minutes they locked lips as Anna groaned with the sensation of his fingers fucking her under her skirt.

Then he broke away and forced her head down to his waiting cock. She knew it would happen, but she was nonetheless shocked at his forcefulness. Up close, she could see that while his penis was not much longer than she had first thought, its girth was substantial. Taking him into her mouth, she began sucking him for all she was worth, teasing the head with her tongue. Her plan was now simple – she needed him to come, because if he didn't, Anna figured she knew what was coming next.

His groans were muffled, but still audible over the on-screen action. Three other men had now moved over to the row in front of her to catch a better look, and Anna watched as one by one they removed their pants and began masturbating. She couldn't see the two in the row behind her as the backs of the chairs were in the way, but she figured that they had adopted a similar pose. She continued blowing the man at a frantic pace, trying to bring him to a climax, but he kept shifting and slowing her movements with his free hand. On and on she went, with the taste of him now overwhelming, until she was startled by a jet of hot cum hitting her shoulders and neck. One of the onlookers from the row in front had unleashed a river of semen all over her, and he then hurriedly collected his clothes and left.

Anna couldn't believe it, and tried to wipe it off but it was everywhere. The man, aggravated that she had stopped sucking him, forced her head down again just as a second volley of cum hit her arm and pooled across her back, this time from one of the voyeurs behind her. Anna ignored this blast, instead keeping her lips around the man's cock, determined now to get the one climax she needed. But it didn't materialize.

The man was close, and wanted more of her – much more. Pulling his other hand out from under her skirt, he used both to raise her head and push her back into an upright position. Leaning down, the man fished around his pockets before producing a condom. Anna's vagina was throbbing with desire, but she knew that he was too big for her. She looked at him for some kind of reassurance but he was focused on removing the condom from its wrapper. Fumbling a little, he finally succeeded and slid the rubber on.

Anna stared at it, as though seeing a penis for the first time, and began to feel a bit queasy. She was truly anxious now, and almost didn't register when the two remaining men in the row ahead began moving the chairs to create space on the floor. The man got up and grasped her hand, pulling her to her feet. He reached past her, grabbing her coat, and set it down on the floor like a blanket. Then, without making eye contact, he placed one hand on her left shoulder and the other on her right hip, and pushed her gently but firmly to the floor.

Anna's legs were now like jelly, and she tumbled a bit as she went down, falling into a seated position. Before she had a chance to reposition herself, the man seized her ankles and pulled them toward him, rolling her onto her back. The man then grabbed at her skirt, pulling it off, as two of the onlookers lifted the halter top up and over her head. With the exception of her heels, Anna was now naked and feeling very exposed.

As the three voyeurs masturbated furiously, the man positioned himself between Anna's legs. Giving her beautiful body one final look but again avoiding her stare, he took his penis in one hand and held it against her pussy lips. As the crescendos of another sexual coupling on the big screen reached fever pitch, he plunged his rock-hard cock into Anna's vagina, burying it completely. Anna screamed in pain, but her cry was lost amidst the climaxing shrieks of two girls being fucked in the film.

The man hesitated, savoring the moment. He knew that he had never had sex with a girl this beautiful, and now here she was in all her glory, with his penis as far inside her as it would go, and three others watching him do it! Anna, meanwhile, was lying back, grateful for the brief opportunity to get used to his size before the action began. And brief it was, for after the shortest of moments, he began a slow teasing slide out of her pussy. She gasped as his cock was withdrawn to the head, before crying out again as he hammered it back home.

Anna tossed her head from side to side, her hands gripping chair legs as the man went to work. He moved his penis in and out like a piston, and she could feel it growing even bigger inside her. She was vaguely aware of the three onlookers continuing to move about, looking for the best vantage point, and barely noticed as the first unleashed a torrent of cum all over her stomach, breasts and face. Her breasts, heaving with the man's onslaught, glistened in the dim light as flickers from the big screen illuminated the cum flowing everywhere.

The second and third onlookers came shortly after the first. Even as the man continued pounding away, she had the presence of mind to be surprised at the amount of cum that these two voyeurs delivered, as it utterly drenched her, adding to the liquid already coating her stomach and breasts. Meanwhile, the man had increased his pace and was now gripping Anna's legs, forcing them over his shoulders. He then leaned forward, pushing Anna's legs back toward her torso, deepening his thrusts even further. For Anna it was a true mix of pleasure and pain, and she didn't know whether to moan or cry. It felt so good yet hurt so much, and her mind was a confused, delighted mess.

It was after almost ten minutes of hard fucking that the man came. She felt his cock pulsate inside her, and his climax seemed to take forever. Thrusting away, he took absolute advantage of his time with this extraordinary girl, and didn't stop fucking Anna until his penis was completely spent and had begun to soften. Only then did he withdraw, before standing, dressing without a word and leaving the cinema.

Anna lay on the floor, exhausted. She could feel the cum everywhere, most of it collecting in a hollow just above her belly button, and wondered how she would clean it all up. Slowly getting to her feet, she was greeted with a cheer from the remaining men in the cinema, all of whom had been treated to the show of their lives. Anna, who had been oblivious to their presence for much of the time, collected herself and managed a smile. It had been an incredible experience, and it kicked off her week of fantasy in a way she had never expected.

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AnonymousAnonymousabout 18 years ago
WOW

Great start can't wait for the rest of the week!

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READ MORE OF THIS SERIES

Anna Ch. 02 Next Part
Anna Series Info

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