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 extensive 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 hiriking 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 long 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 wait, 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 enranced 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 friend and spend 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 “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 admitsted.

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 attention. 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 third 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 throughoutut the content 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 continueed 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 He knew just what Kaitlyn wanted.

Stephanie drove downtown quickly, not striking up much of a conversation. Her eyes continuously 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 slide the keycard through the lock and opned 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 nervouss 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 andlicked it off as Kaitlyn swwayed 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 understand 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 unfasted 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 clothes from the end table on her side of the couch. “Turn around,” she said, circled her finger in the air. Kaitlyn turned and, very slowly, Stephanie placed the clothes 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 should now as the older woman inhaled her perfume. Kaitlyn could hear her own breathing increase and feel 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 ticke 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 caresing 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 caresed her ears, gliding along the ridges.

Stephanie felt Kaitlyn’s body shiver beneath her touch and moved even closer to her. Kaitlyn felt her clothes 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 appreciatedly.

“You have a spectacular body,” Stephanie whispered. She slide 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 hernipple and let out a gasp. Her hips pushed back into Stephanie’s in her pleasure and feel 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 feel her tremble. Stephanie’s hands slowly pushed fully inside her bra and cradle her breasts, lightly squeezing and massaging them. Kaitlyn’s hard nipples slide between Stephanie’s fingers until they pushed against her palm. Oh it feels 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 knee 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 started 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 slip her hand along Kaitlyn’s calm, 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 struggling 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 clip, just barely touching it through the sexy, thin material. Then so very lightly, she began circled her clip, around and around, barely touching the sensitive little nub.

Kaitlyn was trembling obviously, 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 clip. “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, fasting the other ends of the rope to the chair legs. With the other pieces of thesoft, 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 tighs as she smelled her nectar. Kaitlyn’s thong was soaked with her juices and Stephanie knew she was ready.