The Spider and Her Fly

Part One- The Trap

Well this certainly throws a wrench into things, Mark thought. He had just found out that his roommate was moving in with his girlfriend, leaving him all alone in a Brooklyn apartment that he could no longer afford. He had only just moved to the city two months ago, after his girlfriend of three years had left him, and he was finally starting to attract some clients as a freelance web developer. Despite being educated and working all through college, he barely had two dollars to rub together after paying for food, rent, insurance, and student loans. Everything else he wound up spending on Vanessa, who seemed to be the only person capable of bringing a smile to his face at the moment.

Mark had always had a predilection for a certain type of woman. Throughout his life he had developed crushes on various babysitters, teachers, and older cousins; essentially anyone who was any kind of authority figure in his life. Although Vanessa didn’t have any kind of direct, institutional authority over him, her demeanor and tone made Mark weak at the knees since the first moment he had met her. She was the kind of woman who made Mark both nervous and excited whenever he was in her presence. At 38, a full thirteen years older than Mark, she was a successful partner at a small law firm, but she would have been a catch even without being so professionally accomplished. With her 5’6”, 120lb frame, long auburn hair, trim figure and voracious sexual appetite she was almost more than Mark could handle! Despite being smaller than Mark she was slightly stronger thanks to her long hours at the gym, and she was not afraid to physically overpower him when she wanted to. The best part about her though was that she was willing to indulge some of Mark’s kinkier fantasies.

Part of the reason his previous relationship hadn’t worked out was his ex thought he was a bit of a freak. They had gotten along well for years before Mark saw some porn on the internet that had infected his mind like a drug, awakening new desires he never even knew he had. All he had asked initially was to be spanked now and then, maybe have her be a little more forceful in the bedroom. She had clearly been put off when Mark told her, and a few days later she said it wasn’t going to work out between them. Mark was distraught for weeks before he decided to move to New York and start over.

When he found Vanessa on the website and she not only replied to his message but agreed to meet, Mark was ecstatic! Here was a woman who knew what she wanted and wasn’t afraid to take it. They had started off perfectly, with light spanking and bondage, a little humiliation. But in the weeks since Vanessa had kept pushing him, and each time Mark had left her apartment recently he had felt an unsettling mixture of shame and arousal. Of course he would always go home to jerk off afterwards, but that just made him feel more conflicted and ashamed afterwards.

Thinking of the last time he visited her made his cock swell in his new cage. As soon as they arrived in her apartment she had made him take off all of his clothes and serve her wine before she pushed him under her skirt toward her smooth, slick pussy. After she came he had stood up and started to press his hard cock towards her, but she slapped it away and grabbed his balls, twisting him around and pulling them up between his legs. She then pulled out a pair of handcuffs and linked his hands behind his back. Completely in control, she walked him over to the other side of the couch and bent him over the back before retrieving a leather strap and going to work on his ass, furious that he had tried to fuck her. Welted and begging, she finally decided he had had enough.

She pulled out a small chastity device and fitted it on him before pulling a pair of pink panties up his legs. He spent the rest of the night cleaning her apartment like that; sore, horny and humiliated; before she sent him home that evening still wearing the cage and panties.

Mark was a bit scared by how thoroughly she had dominated him that night, all he had really wanted was some light spanking and bondage, maybe a finger up the ass at some point. He would just have to be a little more assertive in the future. He would let her know tonight to take it down a notch. Still, he thought, it had been one of the most erotic experiences of his life, and it hit Mark like a sledgehammer when he realized he might have to leave her for good if he couldn’t work out a new living arrangement.

Mark laid down on his bed and thought about his options. Couch surfing wasn’t an option, he had only been in New York two months and didn’t know anyone besides his current roommate and Vanessa, and he knew it was way too soon to ask to move in with her.

Moving home was out of the question, his parents lived all the way in Arizona, and he didn’t exactly leave on the best of terms with them. Besides, there was no real work in his field in that area, and he wasn’t eager to go back to bartending.

Mark began looking online to see if he could find a spot for himself, but everywhere he saw was completely out of his price range, especially with the housing rush as all of the college students were snatching up anything remotely affordable.

The third option was to try and find someone on craigslist, but he had heard so many horror stories that he considered that a last resort.

After wracking his brain for the better part of an hour, he came to and realized he was going to be late if he didn’t hurry. Mark rushed to the bathroom to clean up. Looking at himself in the mirror, he wondered again how he had gotten so lucky with dating Vanessa. While he was reasonably attractive, with his clean shaven face and long dark hair, he had always been self conscience about his 5’7”, 140lb frame, and his lack of body hair. Vanessa didn’t overtly flirt with other men when they were out, but she did always seem to be a little extra friendly around larger, more masculine men. He finished getting dressed and rushed out the door to meet her at the restaurant.

…..

Vanessa stepped out of the shower and slipped on her blue silk bathrobe as she started preparing for her date with Mark. She adored spending time with Mark, aside from being clever and interesting, he was also a naïve little boy, and she was enjoying leading him down the rabbit hole. They had met a month ago on a BDSM contact site, and although she wasn’t very excited to meet at first, she became much more intrigued when she discovered Mark had only had one girlfriend previously, one who was never dominant. She found herself becoming thrilled at the idea of capturing this naïve little boy who just wanted to try out a bit of bondage and spanking. Mark may think he’s just dipping his toes into the water, but I’ll be sure to drag him into the deep end, she thought.

She had found there was a fine line to walk when finding and molding the perfect slave. There were lots of men who would willingly debase themselves completely, but without offering any resistance Vanessa found little sport in dominating them. Mark was currently a willing sub, but she knew he would bolt if she pushed him much further, and she was growing impatient. She fed off that look in a boys face when he realizes that she has complete control; the look that knew it was too late to back out. She usually saw it when she informed her desperate, panicking slave that his safeword no longer applied.

She knew that Mark was already infatuated with her. What she needed now was leverage. While she could always try going the photo/video route she wouldn’t even know where to send the evidence should Mark revolt. He had no friends in town, no full time employment, and no social media presence. Since that fucking 50 Shades of Grey book had come out everyone seemed to be getting into BDSM, so a few indiscriminate photos weren’t necessarily the deathblow they once were.

While she had always had the body and personality to secure the necessary infatuation, it was only recently that she had gained the means to fully fund her lifestyle and obtain the necessarily leverage.

Vanessa had graduated summa cum laude from Princeton and now worked as a partner at a small law firm specializing in intellectual property. While she was sharp as a whip and very good at what she did, many of her colleagues had speculated that maybe she had slept her way to the partnership. She grinned when she thought about it.

While she had no doubts that she would have made partner eventually, she had quite a head start over her peers thanks to her domme friend Sarah, who had been seeing a senior partner at her law firm for a few years professionally. Vanessa was confused when she saw the photos of her boss, David Ludwig Jr, partner at a multi million dollar law firm, married with two kids. The photos showed him dressed in a frilly pink maid’s outfit cleaning Sarah’s apartment, but after Sarah explained the ins and outs of both her profession and her relationship with David, Vanessa started to come around to the idea of having a slave. The following night they arranged to get together and have David serve them. Obviously they declined to warn David, and he was shocked when Vanessa walked in to find him gagged, plugged, chastised, and kneeling in the corner. Vanessa played her part perfectly, feigning outrage and disgust. After that Vanessa moved up the corporate ladder quite quickly.

Vanessa stepped out of the bathroom to get dressed, going through her closet. She selected a pair of black jeans, fitted white tee shirt and a black leather jacket, with a pair of clean white designer sneakers. She looked sexy but not trashy, and totally comfortable. As she hopped in the cab to meet up with Mark, she lamented things weren’t moving faster. She was eager to train him as a real slave and really bind him to her, but she was at a loss as to how to do that without scaring him off.

…..

“ So that’s pretty much the situation. Looks like unless I land a major client I’ll have to leave the city by the end of the week. I just wanted to let you know in case things…. you know… don’t work out.”

Vanessa struggled to hear the end of Mark’s sentence, stunned by the gift he had inadvertently laid in her lap. They had just finished a nice dinner at a favorite Chelsea bistro, and she was about to pay the check before taking Mark back home for some fun. Her mind raced as she thought of the possibilities, while this would certainly accelerate her usual timetable, it was too good to pass up. Leave the city?! She knew if she played this right she would have him utterly dependent on her by the end of the week.

“I’m… I’m so sorry to hear that Mark!” she said, sympathetically. “If there is anything I can do let me know, I’ll try and think of something, I couldn’t bear to give you up.” She reached across the table to hold his hand, he was clearly embarrassed by his situation. “Why don’t we go home and I can take your mind off of things?” She said, with a wicked grin.

Mark simply couldn’t refuse an offer like that, and after returning to her apartment, he quickly found himself wearing only the panties and chastity device again, which was shortly followed by a pink leather collar. After an hour of serving her while she bathed, tidying up her apartment, and giving her a long, deep massage, she finally lead him to the bedroom and tied him firmly spread eagled to the bed.

Reaching into the nightstand she quickly found the 2” red ball gag and fastened it securely around Marks head. Vanessa slowly removed Mark’s tight chastity cage, clipping the individually numbered plastic padlock to slide the tube off of Mark’s desperate cock. She wondered faintly if he had cheated and slid his cock out of the back for some fun. She hated knowing that he could potentially get it off if he wanted to. Oh well, she thought. She’d remedy that problem soon enough.

Vanessa smiled at her tightly bound toy, looking forward to springing her trap. She found the tube of lube, squeezing some out onto her right palm. She laid next to Mark with her thigh draped over his own leg, head propped up off the bed, her full crimson lips just inches from Mark’s ears. She slowly reached down and started to very softly rub her lubed hand up and down Mark’s aching, denied cock.

After softly stroking Mark bringing him to the edge a few times she was ready. She leaned down and purred into Mark’s ear “So I’ve been doing some thinking about your little problem. It seems to me that you only need a place to stay while you get back on your feet, until you can drum up some more work and find a new apartment, right?”

Mark moaned and nodded, barely hearing what she was saying, completely lost in the soft, warm sensation of her hand on his cock. He hadn’t cum in almost a week, and he was desperate to do so.

“Maybe we could work out a little quid pro quo? I’ll allow you to live here with me for a time, just until you find another place. I’ll let you use my storage unit to keep all your stuff, you can just bring your laptop here for work. I’ll even let you live rent free and I’ll cover your food so you can save up. Does that sound good?” she whispered into his ear.

Mark was nearly delirious with pleasure at this point, and he nodded eagerly at the prospect of moving in, that would solve all his problems, and he would get closer to Vanessa!

Vanessa grinned like a cat who had just got the cream seeing Mark nodding franticly. She increased the speed at which her hand slid up and down Mark’s quivering shaft, touching it softly to keep him on the edge, before continuing with her proposition.

“Of course, since I’m being so generous offering you room and board, I’ll expect something in return. You will defer to me in all things, what you wear, how you act, how you spend your time. I’ll insist you take care of all the little domestic tasks while I’m at work, and when I return you will serve me as needed.”

“Like a butler?” Mark grunted through the gag.

Vanessa giggled thinking of the maid’s outfit and high heels she had stored away and replied “Yes, I suppose you could say it would be like you were my butler.  It’s important that you understand thought that this wouldn’t be all play like it’s been so far. I’m offering you a way to get your life back on track, and as such I expect a serious commitment from you. You will cook and clean, take care of my laundry, and focus all your time outside of work on making me happy. At times it may be tedious, unpleasant and boring, and I reserve the right to discipline you however I see fit for unsatisfactory work or behavior. But I can assure you that we will have plenty of time to fool around as well, and I think this will be quite rewarding for you. Why, you may even get more attention than you can handle!”

Mark nodded thoughtfully as he reviewed the offer. He knew Vanessa could be demanding already, and the thought of her in this new dynamic was intimidating to say the least! But on the other hand Vanessa was gorgeous, wealthy, powerful and interesting. He was totally infatuated with her and the thought of being her slave was something he had spent many nights fantasizing about. Besides, if he didn’t agree he would probably have to leave the city for lack of a place to stay anyway.

Vanessa leaned close and whispered in his ear as she swirled her hand around the head of Marks cock “So what do you think? Are you ready to be my slave?”

Mark grunted in agreement, nodding frantically, lost in passion.

Vanessa smiled and slowly slid her hand from his cock, leaving him twitching and straining against his bonds. “Good boy! God now you’ve gotten me all worked up. Why don’t you take care of your owner while I fit this chastity back on you. I think we’ll save your satisfaction after we see how well you perform as my new slave.”

With that she removed Mark’s gag, ignoring his protestations, swung around on the bed, lifted up her skirt, and lowered her glistening lips down onto Marks outstretched tongue. She gasped as she felt his tongue slide between her lips up to her clit, thinking of all the fun she was going to have with this unsuspecting, naïve little boy.