She Likes It Kinky

Clare had her whole life ahead of her. She'd just graduated college and had moved into an apartment in the heart of Minneapolis, where she'd started work as a psychiatrist at a large medical center. Not only was she successful, but she was also very, very easy on the eyes. She stood a little over five and a half feet, with wavy brown curls reaching just down to her 36 C breasts. Her fair skin never kept a tan very well, but it was clear and smooth like fresh cream.

As she strolled into work on her first day, she was introduced to her new coworkers and shown to her small, but appropriate office. It was big enough that she had enough room to see clients and do her job, but not big enough to warrant much jealousy from other workers. Clare sat down at her desk and began sorting through new patients. As she ran her eyes down the list, she happened upon a name that seemed familiar; she had gone to school in a nearby suburb with a guy named Tommy, and it sounded like it might be him. They had been friends for the majority of their lives, but as of late they hadn't had much contact. Her curiosity would be satisfied at 2:00 when the mystery patient would be coming in for a session.

Clare's day was exciting to say the least as she met with her new patients and got to know them, all the while in the back of her head she was thinking about Tommy and if it was really him. As the clock struck 2:15 she began to doubt her suspicions when she heard a knock on the door, prompting her to invite her patient inside.

"Sorry I'm late," the guest came in and fumbled to get his winter jacket off. "I just caught up in traffic, it's very nice to meet you Doctor..." he looked up and saw that it was Clare, his childhood friend and the girl that he had been in love with ever since high school. "Excuse me, Doctor Clare?" he said finally.

"Come in, Tommy," Clare said, smiling uncontrollably. She got up and gave him a small hug, which prompted Tommy to stir. "How have you been? Come, sit, how long has it been?" Tommy was a few inches over six feet, with thick, curly brown hair and big, brown eyes. Back when he knew Clare, he had been slightly overweight, but as of now he was surprisingly fit.

"I guess since graduation," Tommy said. "So you're a psychiatrist now? Good to see you're putting that big brain to use."

"Yeah, I...actually, this is my first day," she said, brushing her hair behind her ear. "You're here for some therapy?" she asked, getting back to work.

"Uh, yeah," Tommy replied, a bit embarrassed that his therapist was his high school crush.

"Well why don't you start with telling me why you need therapy," Clare said. "If you want, you can relax on the couch back there," she said, pointing to a couch behind him. He got up and made his way over to the couch while she sat down in a chair across from him.

"I guess I've just been going through a rough patch," he said, slightly slumping into the soft cushions. "During my senior year at college, my mother suddenly passed away and I was pulled from school for three weeks to take care of her affairs.

"Anyway, it wasn't exactly her death that prompted this; I think it was more of the timing. My brother was laid off from his job and my dad's on welfare, meanwhile I'm neck deep in student loans and then suddenly I've got to find a way to pay for a funeral for my mother because I'm the only one with a steady income."

"So you'd say you're feeling depressed due to the circumstances of your mother's death?" Clare asked.

"Yes, to a degree. To top it off, I of course missed three weeks of class and failed all my classes. I need to go back for an extra semester to finish."

Clare nodded as she listened to Tommy's story. In a nutshell, Tommy was in financial trouble and was starting to fall into a depression because of it. As he went on, a solution, though unorthodox to say the least, became apparent to her. When he finished, she leaned forward to offer him a proposition.

"Tommy, I'm sorry to hear about your mother, and I feel terrible that things happened the way they did. I'd like to help you, of course, in any way I can, but I don't think there is anything traditional I can do at this time..."

"So you can't help me?" Tommy said, slightly worried.

"I never said that," Clare said. "I'm saying that I can possibly pull some strings at my college and maybe get your credit transferred there. As long as you can finish their finals, you'll be able to graduate in a few weeks."

"Seriously," Tommy asked. "No bullshit."

"No bullshit," Clare replied, smiling.

"Thanks so much," Tommy said.

"I'll just go make some calls," Clare said, heading over to her desk...

________________________________________  

...Six months later, Tommy had finished college and had started work as a writer at a magazine in Minneapolis. His financial situation had turned around as his mother's life insurance reimbursed him after the funeral, and in addition he had received a sizable amount from his mother's life savings through her will. He hadn't returned to Clare's office ever since that day, mostly because he hadn't needed to, though he had spent many sleepless nights trying to think of a way he could visit her again.

Tommy spent most of his nights writing, trying to catch up on deadlines whenever sleep eluded him. Tonight in particular was excruciating. He had hit something of a writer's block, and spent the early hours of the morning at his computer, looking on Facebook and checking his email aimlessly. Getting up to get another cup of warm milk to hopefully help him drift to sleep, he was alerted to a new message in his inbox.

It was from Clare. Curious as to why she was emailing him so late at night, Tommy clicked on the message. Once the message loaded, it became apparent to Tommy that, for one, Clare was surely drunk. And two, the message was clearly not meant for him.

In her drunken state, Clare had accidentally clicked Tommy's name in her contact list. And now her erotic message, originally meant to be sent to her boyfriend, was now sitting in Tommy's inbox.

Tommy knew he should delete it right away without reading too much into her personal affairs, but he figured one peek would be fine.

I missed your face tonight, Tim, my love, the message said. You know I'm terrible without you. Why have you been avoiding me? I'm sure you just never got around to calling me today. Here's a sample of what you missed:

Below was a picture of Clare on her bed. Tommy would not have paid it much attention if it hadn't been a picture of her with her hands tied behind her back, while she was on her knees and a ball gag in her mouth. With her back to the camera, she was dressed in just a black laced bra and a skimpy thong. This garnered Tommy's full attention.

'My god,' he thought. 'I never knew she was so...kinky."

I'll be waiting for your call...master. The message ended with that interesting statement.

Tommy scrolled back up to the picture and his eyes were locked on Clare. He'd not felt this way about her in a long time. Seeing her in her underwear would've been enough to warrant an erection from Tommy, but to see her in such a helpless and deeply personal example of sexuality caused Tommy's hand to gravitate to his sweatpants. He gently placed his index finger and thumb on his penis and stroked it through the cotton barrier. The soft lining of the sweatpants felt nice against his cock. It had been some time since he'd had sex; a few hook-ups in college with drunken girls had left Tommy wanting more. The image of his high school sweetheart before him was driving him crazy. He'd never been much into bondage, but as the saying goes, there's always a first time for everything. The littlest things made chills run up Tommy's spine. The way Clare's hair was pulled into a messy ponytail. The way her left breast, outlined by the ebony lace, seemed to invite a little touching. The way she had elevated her butt in the picture; prominently displaying her barely-clothed pussy. But most of all was the look of helplessness in her eyes, as if she was pleading with him to ravage her until dawn.

Tommy's strokes quickened and before long he had pulled down the waistband under his balls, allowing his cock to breathe at full attention. His entire hand was working its way up and down, up and down. His eyes shifted back and forth between Clare's pussy and her eyes. Finally, he released his spunk into a nearby trash can, and grabbed a few tissues to clean himself up a bit before saving the picture and deleting the message.

Tommy knew now that he had to see her, but could not, for the life of him, think of a way to do so without it being suspicious. The solution was granted to him when Clare called him a few days later, asking him to come in for a meeting to see how he was doing. Being extra careful to be on time, Tommy arrived at her office the next day to a seemingly distraught Clare. As he walked in, he saw her compose herself before inviting him in.

"Clare, I'd like to start by thanking you, so much, for helping me out a few months ago," he said, sitting down in front of her desk.

"Oh, please, don't worry about it," Clare said sheepishly.

"No, really, you helped me out like no one ever has. Things are finally looking up, and I have you to thank." Clare smiled and blushed, not used to getting praised by her patients.

"So you're doing well? Nothing you need to discuss with someone?" Clare asked, trying to move the conversation along

Actually, I'm glad you asked me to come today; I've been trying to think of a way to repay you."

"Oh, you don't have to do anything too big, but I suppose if you wouldn't mind dinner with me tonight, I wouldn't say no." Clare said.

"Tonight? Sounds lovely," Tommy replied.

"Excellent, if you don't need anything else, then I'll let you go. I'll call you when I get off work, we'll meet somewhere nice, okay?" Clare stood up and Tommy quickly followed suit. They both made their way to Clare's door, and Tommy wished her a quick goodbye before stepping out. As Tommy walked down the hall, he received and email and dug through his pockets for his phone. Again, the message was from Clare and again, it was addressed to a Tim. It had only one sentence and one picture. The sentence read, "See you soon." The picture was a candid shot of Clare's pussy under her dress. Tommy nearly fell down the stairs as he made his way to his car.

Meanwhile, Clare slumped back into her chair, grabbed sip of coffee, and smiled to herself...

________________________________________   Clare showed up on time, as promised. She had put on a nice dress, slightly formal but certainly comfortable. She stood outside the restaurant, looking for Tommy expectedly. Five minutes late, Tommy drove up and handed his keys to the valet, escorting Clare inside and to their table.

The conversation was light at first, generally catching up with each other since graduation, sharing memories of college over a bottle of wine. Finally, Clare broke the chitchat with something that troubled her.

"I'm being audited," she said. "I'm almost positive I'm about six thousand dollars behind, which of course adds up to about ten when you factor in fees and late payments. And while work's been fine, I just can't find the money for it."

"Let me help you," Tommy said, almost immediately.

"What? I...no, I couldn't ask you to. I was going to ask if you knew any good accountants, but I certainly don't want you to feel the need to help me. I mean, it's too much to ask."

"Nonsense," Tommy replied, puzzling Clare. "I've been doing awesome at work; I have plenty saved up from work and my mother left me quite a bit from her savings. If you need ten, I can give you twelve."

"No, please," Clare said, trying so hard to say no. "I couldn't take your money; I can't promise you I'll be able to pay you back at a reasonable time, and I don't want things to be weird between us."

"You don't need to worry about paying me back. You bailed me out of a tough situation; the least I can do is return the favor."

"Honestly?" Clare asked. "I mean, I really don't want to burden you with this."

"It's no trouble, really," Tommy said. "And I don't want you to think you owe me for it."

"I...I don't know what to say..." Clare said, on the verge of tears. Tommy looked up from his menu to see Clare in such a vulnerable state. Whether it was his act of selflessness or the half-bottle of wine she'd already drank, she was so grateful for his kindness that she was choking back tears in order to not make a scene.

"It's okay," Tommy said. "Let's just have a great dinner and I'll give you however much you need." Clare smiled and thanked him, and the two of them enjoyed the remainder of the evening. They walked around the city for a while, long enough until Tommy drove Clare home. She gave him a kiss on the cheek and reluctantly accepted his check before heading upstairs.

Clare set the check on her bed and took off her coat, hanging it in the closet of her bedroom. Her apartment, that she now wouldn't fear losing, had a very spacious bedroom, fitting her queen size bed, two dressers, and a large upright mirror. She even had a flat screen TV mounted above one of her dressers.

Clare unzipped the back of her dress and shuffled her arms out of the sleeves. The dress dropped to the floor and she stood standing in her underwear, with a pair of pantyhose hung on a garter belt. She propped up a pillow against the wall and lay down on the bed, reaching for the TV remote. Paging through her DVR she found what she was looking for. Pressing play, she set the remote down and took off the belt.

A woman was tied up in a warehouse. The ropes crossed across her entire body, with one rubbing up against her bare pussy. In her mouth was a piece of cloth, muffling her voice. A man with a mask appeared, naked with his ten-inch cock hanging down. Clare reached a hand down her panties and began fondling her breast with her free hand.

The man picked up the woman and brought her over to a chair, where he untied her and promptly sat her down and strapped her into the chair. He hoisted her legs up into stirrups and then fastened restraints on those too. Another man appeared on screen behind the chair, reaching over the chair and rubbing the woman's breasts, whose muffled cries escalated. Clare unhooked her bra and set it next to her on the bed.

Meanwhile, the first masked man had begun fingering the bound and gagged woman, yelling obscenities at her as his fingers ran up and down her pussy. Clare's hand followed suit, with her middle finger sliding along from top to bottom. Every while she would stop at the top and circle her clit with her finger for lasting satisfaction. Finally, she lifted her ass off the bed and kicked her panties off, where they landed on the ground in front of the bed. Her muff had just the right amount of hair, neatly trimmed into a triangle.

The masked men were now fucking the woman, taking turns pumping their stiff cocks inside her dripping pussy. Her eyes, staring intently at the men and their penises as they continuously would switch positions, causing her distress by delaying her orgasm. Clare was now trying to keep up with her two fingers pumping in rhythm to the action on the screen. Her free hand clutched the sheets as she shuddered off her first orgasm.

The men switched up their tasks; one continued to fuck her while the other began whipping her breasts. The harsh lashes crossed lines across the woman's bosom, not causing bleeding or any measurable damage, but the stinging whip was furthering the woman's pleasure.

The second man took two clips to the woman's nipples next, and the other man took a second to clip on to her clit. As soon as he did, Clare paused the video and reached for a similar set in her bedside dresser. She took a minute to entice her nipples and clipped those. A stinging pain ran through her breasts and dissipated throughout her whole body. Clare flinched for a short time, and then returned to massaging her clit for a brief time before clamping a clip on it too.

An overwhelming mix of pain and pleasure flooded Clare's brain. She cried out in pain but laughed at the pleasure. She took a minute to compose herself. As her heart rate slowed from the mild endorphin rush, she reached back into the drawer and pulled out an eight inch dildo, thick and long with a built-in vibrator.

"Ohh...Master Tim," she said softly as she placed the dildo in her mouth and began sucking. She rolled her tongue around it several times in her mouth and slurped it to coat it with a good amount of saliva. When she finished, she resumed the video and began the process of sliding the dildo inside her tight pussy.

The video was nearing the end; the first man had switched with the second and was jerking his cock by himself behind the chair, right next to the woman's face. Meanwhile, Clare's dildo was just beginning. The saliva, coupled with Clare's already sopping pussy juices, allowed the dildo to slide inside her almost seamlessly. A silent gasp escaped her mouth as Clare arched her back in reaction to the pleasure. Slowly and surely, she began moving it back and forth; the inside of her pussy sliding back and forth against the fake veins and skin.

Eventually, Clare was getting it halfway inside her. She reached for the bedside table a final time with her free hand and grabbed a remote. By pushing the power button, she started a hidden camcorder in her closet. She had positioned it just so that it captured her bed, along with the TV. She made sure to be able to see the dildo going in and out of her juicy cunt, along with the porn on the screen. As the camera started rolling, Clare then switched on the vibrator with her finger.

Instantly Clare shot upright with pleasure. She moaned loudly as she returned to her horizontal position. The vibrator felt like it was mixing up her insides, and Clare enjoyed every second of it. The clip on her clitoris had begun to numb it, so she promptly removed it and started massaging it with her free hand. The intoxicating combination of pain and pleasure was taking its toll on Clare, who began moaning with every pump of the dildo.

In the video, the first man began to ejaculate on the woman's breasts from behind. Meanwhile, the other man burst inside her, pumping her full of semen and pulling out after the deed was done. Cum seeped out of the woman's pussy and spilled out onto the floor while the camera took in everything going on in Clare's bedroom.

"Ohhh...Master Tommy..." she moaned. "Please, please...don't stop. Don't...pull out. I want your cum so badly. I want it in my pussy, in my hair, on my boobs, on my stomach, everywhere." Tears of joy began to settle on her cheek as she plunged the dildo in and out of her soaked pussy. The juices from her cunt had produced a sizable dark stain on the bed sheets.

All of a sudden, the muscles in Clare's pussy tightened themselves around the dildo, preparing for orgasm. Clare moaned Tommy's name several times as she brought herself to climax on camera. Her free hand formed a fist and she grabbed hold of the sheets. At the very moment of her climax, Clare removed the dildo and juices flew from her pussy, across the room until they landed on the dresser across from her. Her entire body spasmed as juices continued to squirt forth from her. She continued to moan and squirt for almost thirty seconds, before long the spasms stopped and she began to settle down.

Clare folded herself into the fetal position, facing towards the camera. She gently ran her finger along her pussy to quiet it, and her gasps for air settled to panting and eventually full breaths. Clare then sat up and got up off her bed, standing up to wipe some of the cum off her legs. She took her dildo and licked her delicious juices from it before returning it to the drawer, along with the clips and the remote to the camera. After shutting off the TV, Clare walked in front of the camera and did a slight wave before shutting it off. She then put on an oversized T-shirt and crawled into the dry side of her bed.