Crossing the Lines

As dusk gave way to evening Debby found herself walking down the street lost in her own thoughts.

"Why did I agree to this?"

"Will I go through with it?"

She wasn't sure, and yet she continued walking to meet a man she felt she already knew, and yet had never met. It had started innocently enough. They had met on the internet, in a chat room. Debby would sometimes log on in the morning before work, or after work when she was bored, and chat with various people about the topics of the day. Harmless stuff, until she met Alex. Even that had been fine, in the beginning. He piqued her interest; they discussed topics from politics to religion to international affairs, or just pop culture subjects like music and movies. He could be funny at times, and at other times she found him irritating. Sometimes he was confident, and sometimes cocky which wasn't nearly as appealing. Debby always found their conversations interesting though, and continued to seek him out when he was available.

Often they would talk for an hour or two, or occasionally just for a few minutes. And yet, as time went on and they got to know each other better Debby began to look forward to seeing him. She would log on to see if he was there, and if he wasn't she would log off, a bit disappointed. The more time they spent together, she began to feel like she could tell him anything, and he seemed to be as interested in her as she was in him. Perhaps more. They would meet and chat and joke with each other, and then go on with their days.

One issue kept coming up, though. Alex was an incorrigible tease. He was always making comments that on the surface seemed tame enough, but in the right light could be considered blatant sexual innuendo. Debby was upfront about the fact that she was a happily married woman, but that didn't seem to deter Alex in the least, as far as the teasing went. Even when Debby pointed it out and scolded him for it he would only be chastened for a short while before continuing. Eventually Debby began to tease him right back, as long her husband wasn't around to see what she was typing. When she was honest with herself, Debby discovered that she enjoyed it. She enjoyed the attention. She enjoyed being chased.

Initially she had closely guarded her personal details, and Alex had as well. But, over the course of their conversations, they slowly let their guard down bit by bit. She got to know what he did for a living, and she found herself telling him about her career. When she asked him about his age he laughed and said, "What does that matter?" Eventually, though, she discovered that he was a few years younger than she was. "I guess you could call me a cougar," she joked, and they both laughed.

Debby found herself attracted to this man she hadn't met, and even though he would hit on her shamelessly she continued to respond to him. Her scoldings came less often and with less vigor, and she suspected he could tell that she didn't really want him to stop. They began to plan to meet each other online when they could, and even exchanged email addresses so they could keep in touch with one another. Occasionally in their discussions he would go too far and she would tell him that he had crossed a line. They could tease each other, but he had to respect the fact that she was married. (Not to mention that she would be mortified if her husband saw some of the things Alex said to her!) "Nothing is enough for you," she would say. And yet, Alex continued to cross the lines, and Debby found herself doing the same. She couldn't help herself. He was attracted to her and she was attracted to him and it was obvious to both of them.

They began to be more open with each other about sex, and they would discuss fantasies, likes and dislikes. Debby couldn't believe she was telling this stranger about her most private details, but it was just words. It was just online. Eventually Debby and Alex began being explicit with each other about what they would like to do with each other. In bed. On the floor. In the car. Debby blushed at the thought of some of the things she said to Alex, and if anything he was even more unabashed and she would warn him when her husband was around. She didn't want her husband to see some of the things Alex would say to her. Alex would chafe when he had to "be good" but he went along. When Debby would tell him, "My husband is gone, you can be bad" it took no urging to get Alex in the mood. Debby's heart would start racing, and she would get wet just thinking about some of the things Alex would say. "At least I can't get pregnant this way," she told herself.

After their conversations Debby would sometimes have to go find her "toy", which was a rather sizable vibrator that not only penetrated her pussy but also her bottom, and rubbed her clit at the same time. She would slide the vibrator in and out of herself and pretend that it was Alex. He was upfront with her as well; towards the end of some of their conversations he would say, "Well, I have to go to bed, but first I'm going to have to take care of myself since you've gotten me so turned on." She knew that he thought of her while he masturbated, and that thought alone would sometimes get her so wet and aroused that she couldn't be bothered to go get her toy and had to rub herself to release right then and there.

One day Debby's curiousity got the better of her and during one of her online conversations with Alex she asked him where he lived. When he responded her heart skipped a beat and she almost gasped. They lived in the same city! She hadn't even been sure if they lived in the same country. Debby wasn't sure what she should tell him, but the long pause had Alex asking if she was still there. "Yes honey, just surprised is all. I didn't expect you to live near me," typed Debby. Alex responded: "How near is near?" And Debby typed back: "Probably walking distance."

Now the long pause was on Alex's end, and Debby smiled to herself. Finally he typed, "Maybe we should meet?"

Debby's hands were shaking and she didn't know how to respond, so she simply logged off without another word. For a few days she didn't log on to talk to Alex, and although he sent her a few emails she deleted them without reading them. "I am a married woman," she told herself. "I can't do this." And yet, she would still find herself checking her phone regularly to see if Alex had sent anything. She would lay in bed and think about whether or not to respond to him at all, or just walk away and pretend none of it had ever happened.

But she would still think of him when she went to sleep at night, and when she woke up in the morning. And when she would use her toy. (Especially then!) Finally, after almost a week had gone by, Debby resigned herself to the fact that she wanted this man. She wanted him inside her. She wanted him to do to her all the things that they had talked about. She had confided in him her most secret fantasies, and she wanted them to come true.

And so, she sat down at her computer and composed an email for Alex.

"Alex honey, I'm so sorry I disappeared the other day and that I haven't responded to your emails. I wasn't prepared for that. You know I'm a married woman. But, I just can't get you out of my head and I've accepted the fact that I want you, and that I'm willing to meet you if you still want to, but just this once. For one night you can have me any way you like, and I want you to fulfill my fantasies too. (You know what turns me on.) And then that's it. It won't happen again. It can't. Please understand.

Kiss!

Your Debby"

The cursor hovered over the Send button for a while before Debby finally clicked the mouse button.

It didn't take long from there. Of course Alex was interested. Of course he wanted to meet. They exchanged photos and found each other attractive. They talked on the phone and agreed to a date when she would be able to get away for the night. They would meet at a hotel that was within walking distance of her apartment. Debby made clear to Alex that he was free to do with her as he pleased, as long as made sure to fulfill some (if not all!) of her fantasies. Once she arrived she would cede control to Alex and let him have his way. She didn't want to know ahead of time what he would do, and wouldn't discuss it with him. The very thought that he was going to be free to do whatever he wanted sent shivers down her spine.

And so she found herself wearing a tight dress barely covering her C-cup breasts or her firm bottom, walking into the lobby of the hotel as if in a daze, onto the elevator, and then standing in front of the door to the room Alex had reserved. She knew he was waiting for her inside, and paused and took a deep breath before knocking lightly on the door.

The door swung open and there he stood. They stared at each other for a moment before he put his arms around her and held her close. She wrapped her arms around him and sighed. Alex stepped back, and with a mock bow he swept his arm in the direction of the room and said, "Please come in, milady."

Debby walked into the room and heard the door shut and lock behind her. Before she could even give the room more than a cursory glance she felt Alex's arms around her again, this time from behind. His hands crossed in front of her tummy and he pressed against her. He was already hard. She could feel his stiff manhood against her backside, and as his hands began to roam he whispered in her ear: "Mmmm.... I've wanted you for so long." His hands grasped the fabric covering her breasts and squeezed as he rocked his hips against her, and in answer she leaned back against him. His hands slipped into the top of the dress and roughly pulled it down a bit, exposing her breasts. As he had requested, she wasn't wearing a bra. Once her nipples were free of the fabric they began to stiffen, and he gently took them between his fingers and squeezed and lightly twisted them. In no time at all they were erect and she felt goosepimples on them as Alex began massaging her naked breasts, occasionally running a finger across a nipple.

With his right arm he held her tight against him, and with his left hand he reached down and began to tug the hem of her dress up until it was bunched around her waist. His hand slid across her bare belly before she felt his fingertips insistently push under the elastic band of her panties. She knew he would soon feel how wet she was, and the thought made Debby even wetter. As his hand slid farther into her panties she felt his fingers run through the hair on her mound, and he twisted his fingers through the curly hair and tugged gently. "You know I told you I prefer shaven. You've been a bad girl. I'll have to take care of this," he whispered in her ear, before running the tip of his tongue in and out quickly.

Abruptly Alex released Debby and pushed her forward, and she was barely able to get her arms up in time to stop her fall onto the bed. Her breasts swung freely and before she could say a word Alex tugged a mask down over her eyes.

"Hold still," he demanded. "I want to look at you."

She could just imagine what he was seeing. She was on her hands and knees on the bed, her breasts hanging down, the dress just covering her belly and hips. Her sheer white panties didn't cover much of her bottom. Debby gasped as she felt his hand run across one exposed cheek, then across the panties and down the other.

She heard him move to the other side of the room and open a drawer, and return to the bed.

"Turn around," he said. Debby awkwardly turned on the bed, still on her hands and knees, and Alex grasped her right wrist and pulled her hand up, placing it on the bulge in his pants.

"Well?"

Debby wasn't sure what Alex wanted her to say, so she said nothing.

"You know what to do," he stated flatly.

And she did know what to do. She supported herself on her left hand, and with her right hand she lowered his zipper and reached inside. Wrapping her fingers around his hard shaft she squeezed him a few times through his boxers. Alex reflexively thrust himself against her hand, and she extracted his erect cock. Holding the shaft tightly she pumped it a few times before leaning forward and sticking out her tongue. As soon as the tip of her tongue touched the head she realized he was already leaking pre-cum and she moaned before opening her mouth and engulfing the head. She swirled her tongue around him as she continued to pump her hand on his shaft. She felt him run his fingers through her hair, and then grasp it tightly. At the same time his other hand took her wrist and pulled her hand from his shaft, and he roughly shoved his cock into her mouth and pulled her by the hair towards his hips. Debby only had a moment to draw a deep breath through her nose before he started pumping his cock in and out of her mouth. With the mask she couldn't see him, but she could hear the wet noises her mouth was making as he took his pleasure. He thrust against her for a minute or two, and then suddenly withdrew. She felt his hands at the back of her head, and before she knew what was happening she felt something roughly shoved into her mouth. Suddenly Debby realized Alex had placed a ball gag in her mouth. She moaned, partly in fear and partly in desire, and Alex said "I won't need to use your mouth for a while, and you won't need to either."

She felt his hands on her shoulders and he pushed her onto her back. She felt his hands on her left wrist, and then felt something rough slide over her hand until she realized he had pulled a leather cuff tightly around the wrist. Her right wrist followed, her arms now pulled wide. Alex put his hands on her ankles and pulled her legs together, and then he held both ankles together with one hand and began to push them up until she was bent almost double, her bottom up in the air and Alex above her. She felt him slide his hard cock inside her panties and he rubbed the bottom of his shaft against her pussy lips as he thrust himself against her. The tip of his cock ran past her clit each time he thrust forward, and she lifted and tilted her hips trying to get him to enter her, to no avail.

"What did I tell you about this?" he growled, and pulled his member out of her panties. She felt his fingers grasp the fabric and with a loud rip he tore them off, exposing her sex. Debby felt both of Alex's hands on her ankles again, and within moments he had placed leather restraints on each, spreading her completely open. Apparently the restraints were attached to the bed; she couldn't close her legs or move her arms. She felt the bed shift, and then Alex was gone.

She lay there for a few minutes, bound, gagged, blindfolded... and delirious with desire. She felt so exposed; the cool air from the hotel air conditioning was causing her wet pussy to cool even though she had never felt so hot before. In the distance she could hear water running.

She heard Alex come back into the room, and she pulled tightly against the restraints as she felt a sudden shock of heat between her legs. Alex had placed a steaming hot wet towel over her pussy. Alex placed his palm over the towel and her mound and massaged it, saying "If you won't shave yourself I'll do it for you."

Debby relaxed against the restraints and lay back in the bed, enjoying the wonderful sensation of Alex's hand massaging her pussy through the hot towel. Her hips slowly moved in rhythm with his hand, until he removed the towel and she felt him slathering shaving cream all over her sex. When she felt the razor run along her inner thigh Debby froze, and held her breath. Alex gently tugged at the hair with the razor, starting with her mound, then at the apex of her thighs. The razor scraped against her skin, carefully avoiding her lips. As the razor made its inexorable way around her private area the cool breeze again brought goosebumps. When she was almost completely clean she felt Alex pinch her nether lips together and pull them this way and that, the razor ever so slowly and carefully scraping against her sensitive skin.

Finally Alex seemed satisfied with his work and she heard a splash of water before his wet hand rubbed her mound and pussy down, apparently cleaning off the last of the shaving cream. Again the bed shifted as Alex left the room. Debby lay on her back, her legs lewdly spread, wondering what Alex was doing. Suddenly she heard a loud clicking sound and realized it was a camera shutter! She tried to say "NO!!!!!" but couldn't through the gag, and she bucked against the restraints as the camera continued to capture her in this most exposed state. "Something to remember you by, honey," she heard Alex say, with a hint of a smile in his voice. Defeated, she lay back and let him have his way with her through his camera lens. She lost track of how many pictures he might have taken. At this point it didn't matter.

After a moment Debby realized that it was quiet again. Maybe he was done taking pictures? She lay there for a few minutes, waiting for something, anything to happen. With a shock she suddenly felt something touching her pussy, and when she felt Alex's breath on her wet sex she realized that it was his tongue. "Much better," he said, and then continued licking her. He ran his tongue along her lips, parting them gently before sliding his tongue inside her. When his tongue slid out of her pussy it swirled around her clit and gently lifted her hood, tapping insistently on her clit before sliding back inside her. Debby moaned and bucked her hips against Alex's mouth and felt his lips close around her pussy before sucking briefly on her clit. When his tongue slid inside her again Debby came, her juices flowing freely into Alex's mouth as he lapped at her nectar. Debby pushed her pussy against his mouth as hard as she could as her orgasm consumed her.

Before she had even finished cumming she felt Alex slide his hard cock into her slick, clean-shaven, soaking pussy and felt his weight on her as he began to thrust deep inside her. She felt another orgasm building as Alex pounded into her. Just as she was on the verge of cumming again she felt his cock withdraw. She felt the tip probing just below her pussy and she realized that Alex was about to fuck her in the ass. Debby moaned into her gag, and felt his insistent cock pushing into her. She relaxed and allowed him to sheath himself in her to the hilt, and as he began steadily thrusting in and out of her tight backdoor she came again, shuddering against him.

This was too much for Alex, and his pace increased frantically until he suddenly thrust deep inside her and moaned and she felt his shaft twitching inside her as he came. Alex collapsed on top of her and wrapped his arms around her and kissed her cheek. "I think we'll sleep like this for a while," he said, flexing himself inside her to emphasize his point.

"When I wake up I'll have to take that gag out of your mouth, honey. Because that's where I'll be cumming next," he chuckled. "We have all night..."

(To be continued?)