Winning By Losing
Winning by Losing
Kaitlyn realized her mistake too late. She had dared Stephanie, thinking that this was just a game, just a way to have some fun and tease her. But now... she thought she might have gone too far. It's not that she wasn't enjoying the outcome. Far from it. But it certainly wasn't what she expected.
She had dressed a little more sexy for work than normal, perhaps thinking about the reaction she would get from Stephanie, her project manager, perhaps not. Maybe she just wanted to feel good about herself. She said good morning to Stephanie, like she always did, and noticed her profound reaction to her outfit.
Stephanie had to admit that Kaitlyn was incredible. She already knew Kaitlyn was a very stunning young woman, that was one of the reasons she hired the young engineer. Of course, she rationalized it as hiriing a very intelligent, capable woman in a very male-dominated field. But she felt extremely attracted to the young woman. And the outfit Kaitlyn had on today magnified every attribute she had. The color, the style, the cut, the texture, all of it combined into one incredible package. Kaitlyn was a young, intelligent, and incredibly sexy young woman.
Stephanie was in her forties, was in great shape. She prided herself on how good she looked, with firm DD-cup breasts that she never showed off at work, round, curvaceous hips, a big, tight ass, and long legs that many men whispered about around the water cooler when she walked by.
She was married to her college sweetheart, Christopher, fifteen years ago and had two children who were just starting their own college careers. But... she had a secret. She had a longing that was difficult for her to satisfy given her home life. But, occasionally, an opportunity presented itself. And with Kaitlyn, she was anticipating an opportunity soon.
Kaitlyn was in her mid-twenties and was a recent college graduate. She graduated near the top of her class in Electrical Engineering and while it was certainly a male-dominated field and her college classes were almost all men, she really had no interest in them. She found out several years ago, that she was far more interested in women.
She was a small woman, just over five foot tall, barely one hundred pounds, but with lovely, C-cup breasts, one of her favorite features to show off, a tight little waist, and tight, little ass. She had a tough time through college, fighting off all the guys, and was generally too shy to ask any girls out.
She was so excited when Stephanie hired her. She'd expected a man to do the interviewing and a man to be the project manager, given it was with a very technical company, but was very pleasantly surprised by Stephanie. She was an intelligent woman in her own right and Kaitlyn was entranced by her beauty. After she was hired, she felt very drawn to Stephanie, both as a fellow woman in the company but also because of her physical attraction.
They struck up an instant friendship and spent their lunch hour together in Stephanie's office, eating and playing cards. As the days passed by, Kaitlyn started dressing as much to attract Stephanie's attention as to look professional.
Just six months after hiring her, Stephanie learned that Kaitlyn was a lesbian. They were talking over their lunch card game about a date that Kaitlyn went on and Stephanie seemed very interested.
"I'm so happy for you," Stephanie said, smiling. "It's great. Oh to be young again, right? So? It went well and you're gonna go out again. But, uh, I want more details. Tell me! Did you hold hands?"
Kaitlyn blushed. "I mean... not really."
"You didn't hold her hand? What did you do?"
"We just went to an art gallery and hung out... I don't know."
"Did you kiss her?" Stephanie asked, making the young woman blush a lot. "Oh, like you're embarrassed about kissing, come on."
"Yeah, we kissed," Kaitlyn admitted.
Stephanie seemed even more interested. "So how did it make you feel? Was it good?"
Kaitlyn nodded. "Yeah, it was really nice. She's a really good kisser."
"Sorry, it's just been so long since I've been on a date like that... but I gotta ask... did kissing lead to... other interesting things?" Stephanie pressed.
Kaitlyn blushed again. "I mean... it was kinda nice."
"Kinda?" Stephanie giggled. "Look at you beating around the bush. We can talk... it's just you and me in here. You're comfortable talking with me like this, right?"
"Yeah... I just feel a little shy," Kaitlyn said.
"I just... I'm happy for you," Stephanie said, touching Kaitlyn's arm before pulling it away again. "My husband and I used to do stuff... unfortunately too long ago. So... just tell me what you're comfortable sharing. Ok?"
"Yeah, ok," Kaitlyn agreed.
"So? What did you do?"
"We... we started, like, kissing and... um... we touched each other some."
"You did?" Stephanie looked a little shocked. "Ok... what does that mean? Over her clothes? Under her clothes? Was she totally naked? Did you get her naked?"
Kaitlyn giggled, shuffling the cards for the next game. "I, like, took off her skirt and blouse... and was, like, kissing her... you know... down there." The last she said bending forward, talking in a whisper as if there was someone close that could overhear them.
"Kissing her down there?" Stephanie said, looking very surprised. "Oh my..." She couldn't help but imagine Kaitlyn between her legs, licking her.
"Mmhmm," Kaitlyn continued, finished her deal. "She was so wet."
"How did she taste?" Stephanie fanned her cards, sorting them, but was barely able to take her eyes off her beautiful young friend.
Kaitlyn closed her eyes a moment, as if remembering her first taste. "So good... she was so sweet."
"Did she cum?"
Kaitlyn nodded. "Yes."
"And did she... taste you, too?"
Kaitlyn nodded again, blushing this time. "Yeah."
"Really? She licked your pussy, too?"
"Yeah," Kaitlyn giggled, nervously.
"I see you're excited just thinking about it," Stephanie smiled. "It's ok... You're young, you're horny. You get excited by things. It's ok. I'm a little... excited... myself, to tell you the truth. I may have to convince Christopher to play tonight. Did you... cum in her mouth?"
"Yes."
"You did? Wow... Did you cum a lot?"
"Oh my God, yes," she smiled. "She's so good with her tongue."
"You should really see her again," Stephanie said, sounding motherly, but obviously excited by what she learned about her young team member. "I'm so excited that you got to go on a date. I'm jealous, but I'm really happy for you. So when's your next date?"
"Tomorrow."
"Tomorrow?" Stephanie asked, surprised. "That's quick. What do you think you'll do tomorrow? You think you'll have sex with her again?"
"I think so. Hopefully."
"God, I'm so jealous," Stephanie admitted.
That afternoon, Stephanie had to leave work early. She was too physically aroused to stay there any longer. Then, with an empty house, for the next three hours, she masturbated, thinking about Kaitlyn with her date.
Now, on this Friday afternoon, with a near-empty office, Stephanie had a hard time talking to Kaitlyn, dressed as sexy as she was, and the young woman noticed it. Over the months Kaitlyn continued to joke with her, to flirt with her, giggling at the older woman's seeming shy attraction. Then Stephanie did something Kaitlyn never expected. She invited her young employee to play their lunchtime card game with a little... twist. She suggested, in her joking manner, that the loser would be indebted to the winner for three hours that night. Kaitlyn was surprised by the older woman's boldness as Stephanie suggested the winner achieving ten points would be the lucky one. Kaitlyn accepted the challenge and they both laughed about it. It was still just a joke, Kaitlyn thought, right?
"Don't you need to go home to your family?" Kaitlyn asked.
Stephanie shook her head. "No, there's nothing important going on at home. I'll just tell Christopher I'm working late."
When lunchtime came, Kaitlyn popped back into Stephanie's office holding her salad and steaming bowl of broccoli cheddar soup. Stephanie had already pulled out a deck of cards and was shuffling it. Their favorite game was German Whist a game resembling a strategic version of the card game War.
"Ready?" Stephanie asked.
"Yep. Go for it," Kaitlyn agreed, sitting down.
Stephanie dealt out thirteen cards to each of them, then sat the rest of the deck on the table, flipping up the top card. "Spades are trump."
"What are we playing to?" Kaitlyn asked.
"The first to ten points."
They both picked up their cards and started the game. They played several hands, trading who dealt, each switching the lead, but in the end, Stephanie won. All throughout the contest Kaitlyn continued to joke, continued to tease. But it was Stephanie that had the last laugh, winning the game ten to seven, after winning nine tricks on the last hand, earning her 3 points. As she was putting away the cards and Kaitlyn was getting up, Stephanie told her to meet her at her car after work.
Kaitlyn was shocked that Stephanie would actually make her honor the agreement. She lost her confidence and her steam at that point. Truth be told, she was scared. But she was excited by the prospect of what might happen and that overrode her fear.
For the rest of the day, her mind played over every scenario she could envision of what Stephanie might make her do. She would think some very... kinky... thoughts and then would think, no, Stephanie wouldn't do that, she's married. Kaitlyn guessed that Stephanie would probably make her cook dinner or something. She thought Stephanie was too shy, too nice to do anything that Kaitlyn *really* wanted. But she continued to daydream, getting more excited by the moment.
At 4:40pm, Kaitlyn met Stephanie at her car. They both smiled as Kaitlyn sat in the passenger seat, both of them nervous, or so Kaitlyn thought. But Stephanie wasn't nervous. She'd done this before and knew exactly what she was going to do. She knew Kaitlyn wanted it, too. Stephanie could feel the sexual tension between them and knew just what Kaitlyn desired.
Stephanie drove downtown quickly, not striking up much of a conversation. Her eyes continually glancing at Kaitlyn, wondering what lovely surprises awaited her underneath that incredible outfit. She could see Kaitlyn squirming a little as her daydreams continued to tease her. They arrived at the large hotel in just twenty minutes and walked inside.
Stephanie led her directly to the elevators and up to the tenth floor, surprising Kaitlyn. Stephanie must have booked the room that afternoon, after the game.
Stephanie slid the keycard through the lock and opened the door to let Kaitlyn inside first. Kaitlyn loved the place. It was a good size for a hotel room, with a king sized bed in one area, a desk in another, and a sitting room in yet another.
"Would you like some wine?" Stephanie asked as she casually picked up a bottle from the desk and walked over to the sitting room where Kaitlyn sat.
"Um... yes. Please," the young woman whispered. She wanted a little just to kill her nerves if nothing else. This was more than she expected. It was far more than she ever expected. Kaitlyn was puzzled that Stephanie didn't appear to be nervous at all. And she began to really wonder if her daydreams might, in fact, come true.
They sat on the couch for a moment, drinking the wine. When Stephanie's glass was half empty, she looked at Kaitlyn.
"i know we agreed to this arrangement, but you are free to back out if you're uncomfortable with what we were about to do. I mean, we didn't talk any specifics," Stephanie said.
Kaitlyn felt a shiver go through her body as she realized that this was seriously happening. "I'll... um... I'll stay," Kaitlyn said, nervously.
Stephanie smiled... she was very happy with that response. "As we agreed, then, until nine o'clock you are to do everything I say, without complaint and without question. You're saying that you agree to those terms. If you later decide that you're too uncomfortable, you say 'red' and you immediately go home, it's as simple as that. We forget about the whole thing and it'll never happen again."
Goosebumps were forming all over Kaitlyn's body, making her shiver, and she felt a chill move through her. She nodded.
"Stand," Stephanie asked and Kaitlyn did, setting her wine glass on the end table. "Dance for me. I want you to show me just how beautifully you move." Stephanie was sitting comfortably on the end of the couch, holding her wine glass and slowly circling the rim with her finger. She slowly dipped her finger into the liquid and licked it off as Kaitlyn swayed to some unheard music, her hands drifting all over her body. Kaitlyn turned in circles and Stephanie was transfixed by every move the young woman made.
"Remove your jacket and skirt," Stephanie said, after a few moments of Kaitlyn dancing.
"I... um... don't have a blouse on under my jacket," Kaitlyn said, nervously. Stephanie just smiled back.
Kaitlyn understood that Stephanie didn't care about that. Slowly, she built up the nerve, vowing to not let Stephanie get the better of her, and unbuttoned and removed your jacket. Her breasts were covered in a lovely, lacy bra, which showed her ample cleavage. She tossed the jacket aside and, while looking at Stephanie, reached back and unfastened her skirt, letting it fall to the floor. She stepped out of it and tossed it aside. She was wearing a skimpy thong and Stephanie could see her excitement in it's dampness.
"Come here," Stephanie commanded and stood in front of Kaitlyn. She grabbed a strip of cloth from the end table on her side of the couch. "Turn around," she said, circling her finger in the air. Kaitlyn turned and, very slowly, Stephanie placed the cloth sleep mask over her eyes and adjusted it behind her head. Kaitlyn was now unable to see, unable to know what Stephanie was doing, where she was looking. Kaitlyn felt even more exposed and it made her shiver. She could feel Stephanie's breath on her shoulder now as the older woman inhaled her perfume. Kaitlyn could hear her own breathing increase and felt goosebumps tingle her body.
Stephanie didn't touch her, yet let her face glide over Kaitlyn's back, smelling her. Kaitlyn felt Stephanie's breath tickle down her spine across her ass and down her thighs, making her whimper. The older woman's breath was warm and moist and Kaitlyn could tell that Stephanie was enjoying herself.
Stephanie rose back up, this time trailing her fingertips up her body, lightly caressing it. Kaitlyn felt them slip over her ass and up her spine. She had expected, perhaps even hoped, that Stephanie would remove her bra, but her fingers only lingered there for a moment, moving up to her shoulders and neck. Stephanie's fingertips gently caressed her ears, gliding along the ridges.
Stephanie felt Kaitlyn's body shiver beneath her touch and moved even closer to her. Kaitlyn felt her clothing move against her bare skin and knew Stephanie was very close. Then Stephanie's breath caressed her ear making Kaitlyn physically shiver. The older woman moaned appreciatively.
"You have a spectacular body," Stephanie whispered. She slid her hands down Kaitlyn's neck and along her collarbone before touching her chest. Then moved along the line of her bra. Kaitlyn gasped in anticipation and desire as Stephanie's fingers moved close to her nipples, but never touched over the bra itself. Coming back along the line again, Stephanie plunged her fingertips just inside Kaitlyn's bra cups. Kaitlyn felt them graze her nipple and let out a gasp. Her hips pushed back into Stephanie's in her pleasure and felt her ass press back against Stephanie's thigh. She stayed against Stephanie, loving the feel of the older woman's body against her own.
Kaitlyn felt Stephanie slowly grind her hips against her, letting her thigh slide along her ass, trying to push between her legs. Stephanie moaned softly into Kaitlyn's ear and felt her tremble. Stephanie's hands slowly pushed fully inside her bra and cradled her breasts, lightly squeezing and massaging them. Kaitlyn's hard nipples slid between Stephanie's fingers until they pushed against her palm. Oh it felt so delicious to Stephanie. Her young friend's body was so soft and responsive to her touch. Kaitlyn leaned back against her, laying your head on her upper chest. Kaitlyn's hands hung at her sides, her fists clenching and releasing in her excitement.
Stephanie lifted her hands from Kaitlyn's breasts and placed then on her shoulders. She slowly walked the young woman forward. She could feel them moving across the carpet until they finally stopped. She didn't know where they were but the guesses excited her.
Stephanie turned her and pushed her to sit in the desk chair. Kaitlyn could just hear Stephanie kneel in front of her and then felt her face move close. She could feel her hot breath on her knees.
"I want you to masturbate for me," Stephanie said softly.
Kailyn moaned, a little startled by her request. Stephanie grabbed her right hand and moved it until it rest on her own stomach. She then sat there, waiting, just watching her. Kaitlyn didn't move for a minute so Stephanie slid her hand along Kaitlyn's calf, slowly gliding up and down.
"Remember, you said you'd do... everything... I asked." Stephanie could see Kaitlyn's resolve weaken. She knew the younger woman was excited, she could smell it, and Stephanie knew Kaitlyn wanted to comply. She was just shy and didn't know what Stephanie would think of her. Kaitlyn's hand was slowly stroking her stomach and not moving towards her overheated pussy.
Stephanie could sense Kaitlyn's desire as well as her fear. With one finger, she traced a line down from the waistband of her panties down to her clit, just barely touching it through the sexy, thin material. Then so very lightly, she began circling her clit, around and around, barely touching the sensitive little nub.
Kaitlyn was trembling visibly, breathing hard. Her hands were clenched in tight fists, trying desperately to resist her urges.
"Fuck, you're making me so hot," Kaitlyn said. Suddenly Kaitlyn's hand slipped down to her pussy, quickly slipping beneath her panties, and her fingers started to furiously circle and prod her sensitive clit. "Fuck, yes," she shivered as the pleasure coursed through your body.
Stephanie, then, slowly circled Kaitlyn's nipple through her bra. It was so hard as she teased it, pinching, and rolling it between her fingers. She watched Kaitlyn lick your lips, watched her moan in pleasure as she continued to masturbate. Stephanie couldn't believe how excited Kaitlyn made her just watching her touch herself. After she teased both nipples and removed her hand, Kaitlyn's left hand moved to roughly pinch and squeeze them. She was so damn excited!
Stephanie could tell Kaitlyn was near her orgasm and quickly told her to stop. Kaitlyn seemed unable or unwilling to obey her command, though, so Stephanie grabbed her wrist and pulled it away.
"I said stop," Stephanie said next to her ear, causing Kaitlyn to shiver.
Stephanie opened the desk drawer and grabbed several lengths of rope from inside, setting them on the desktop.
"I think if you can't follow simple orders, then I will have to keep your hands away," Stephanie said. She quickly tied Kaitlyn's hands behind her back, behind the back of the chair, one at a time, fastening the other ends of the rope to the chair legs. With the other pieces of the soft, silk rope, Stephanie tied a loop around Kaitlyn's knees and pulled them up towards her chest and apart, tying them to the same, back chair legs.
Kaitlyn was now bound tightly and was very exposed.
Stephanie sat still for a moment, listening to Kaitlyn's excited breathing. Kaitlyn had no idea what Stephanie was going to do to her and yet she would truly do anything at this moment. Stephanie bent over and kissed each of her inner thighs as she smelled her nectar. Kaitlyn's thong was soaked with her juices and Stephanie knew she was ready.
"Now that you are adequately restrained, it's time to have some fun with you," Stephanie said softly. She stood and moved to the desk where she removed two toys that she had stashed there just for this occasion. Kaitlyn didn't know it, but Stephanie had been in this position before. She'd had other willing women moaning and cumming for hours on end in just the position Kaitlyn had found herself.
Stephanie flicked open a bottle of lube and put a little on the first toy, a very slim vibrator. She circled it around Kaitlyn's thigh and pussy for a moment before she slid it down along the crack of her ass. She wanted Kaitlyn to know exactly where it was going to eventually go. Kaitlyn moved her hips and clenched her ass in either pleasure or resistance as she started breathing heavier, moaning. Stephanie didn't know which and really didn't care. Kaitlyn was powerless to physically stop her. She used the vibrator to circle Kaitlyn's asshole for a moment, relentlessly teasing her.
"Oh god. I've never felt like this," Kaitlyn panted. "What are you going to do?"
Stephanie gently eased the tip of the vibrator into her asshole. "I'm going to fuck you," She said simply.
"Oooooh," Kaitlyn groaned loudly. "Oh my fucking God!"
Kaitlyn's ass contracted and then released on the little toy as Stephanie pushed it deeper into her. She giggled as Kaitlyn writhed in the chair, unable to move far. Once the vibrator was all the way inside, she fucked Kaitlyn slowly, letting her feel the entire length as it pushed in deep and then withdrew, the low vibrations teasing her so perfectly. Kaitlyn was barely breathing now, the pleasure was already making her lightheaded. But this was just the beginning. Kaitlyn didn't know just what the older woman had planned for her.
Stephanie made sure her little anal dildo was securely held inside Kaitlyn and then moved to her other fun toy. This one was definitely bigger and more powerful and was going to make Kaitlyn absolutely sing. Kaitlyn heard Stephanie turn it on, heard the rumbling vibrations, and licked her lips. She thought she might cum just from the anticipation of Stephanie's toy.
Stephanie slid her little monster over Kaitlyn's panty-clad pussy and the rumblings made the young woman moan loudly. Stephanie quickly removed it from her clitoris and Kaitlyn let out a gasp of air. Stephanie was very talented at this play. She had practiced on other young women. She pushed the tip into Kaitlyn's vagina, letting the material be a blockage, and Kaitlyn felt the rumblings deliciously travel up her spine. She lay her head back enjoying all the sensations as they traveled throughout her body. The vibrator felt incredible normally, but in Stephanie's hands it was Kaitlyn's pleasurable torture, it was going to cause the best orgasms of her young life.
With her free hand, Stephanie pulled the thin material of Kaitlyn's G-string aside and let the string lay across her ass. Kaitlyn's beautiful pussy was so exposed to her and her heady scent was like ambrosia. Stephanie couldn't believe how much she wanted to lick and taste her sweet nectar. But she held back, knowing the pleasure would be so much greater later. Stephanie slid the vibrator along Kaitlyn's naked skin, now, letting her juices cover it and make it slippery. Kaitlyn's pussy was so engorged and swollen, her clit so extended, wanting to feel all the pleasure it could.
Stephanie positioned the vibrator at the entrance to Kaitlyn's pussy and slowly eased it in. The young woman's body was wracked with spasms, jerking and trembling as she came at the initial intrusion. Stephanie was slow in her approach so that Kaitlyn didn't become too sensitive too early in Stephanie's playtime. She wanted to make sure Kaitlyn enjoyed every second of their three hours.
Stephanie played, keeping Kaitlyn in the chair, trussed up nice and neatly, exposed to her and her lovely torture devices as she had orgasm after orgasm.
At nine o'clock, Stephanie untied the worn out young woman and helped her lay in the bed, pulling the sheet over her. The women gently kissed and then Stephanie gathered her supplies as Kaitlyn quickly fell asleep.
Kaitlyn was too nervous to go into work on Monday, so she called in sick. But she had no choice on Tuesday. She felt so very nervous when she walked into the office on Tuesday morning. She passed by Stephanie's office on the way to her desk and said a quick 'hi'. As she walked away, Stephanie called her to come back.
"Hi," Stephanie said as Kaitlyn stood in the doorway.
Kaitlyn blushed, nervously. "Hi."
"Everything ok?"
Kaitlyn nodded and smiled. "Yeah."
"Are we ok?"
"Yeah... of course," Kaitlyn smiled.
"Another game of Whist at lunch?"
"Yeah... sure. And, um... maybe on Friday we can make another bet."
Stephanie smiled.
- Stephanie suggested a twist to their usual card game, proposing that the loser would be indebted to the winner for three hours that night, which could involve playing a game using a blindfold, a rope, and a vibrator.
- In an unexpected turn of events, Stephanie invited Kaitlyn to her hotel room after winning their card game, promising to fulfill the debt of losing. Kaitlyn agreed, eagerly anticipating what might transpire, not knowing that the game would involve using a blindfold, a lesbian encounter, and a vibrator.
- With the hotel room setup for their private session, Stephanie proposed a game where Kaitlyn would be blindfolded and appreciated through touch, using a rope to guide her movements and a vibrator to enhance pleasure, emphasizing the dominance-submission dynamic between them.