Terra Underwood started working at Tech Co. in January. The call back was the best Christmas and New Year’s gift combined she could have ever imagined. Her first day was a whirlwind. She got her desk, quota and supplies within the first twenty minutes and was set to work with little preamble.
Being her first real job out of college, she naturally had a bit of a time adjusting. She was friendly enough with her coworkers and fit in just fine, but her first few months were hell when it came to her workload. She would constantly get reports sent back due to an abundance of errors on top of turning in the reports late. Her only saving grace was that her boss, Janet Johnson, was so lenient with her.
Janet took time out of her busy schedule to mentor Terra. She would check in on Terra’s progress whenever she had a chance. She made sure Terra was adjusting properly into the office life with her coworkers and offered a hand with any disputes. The biggest help was the overtime. Terra worked herself to the bone every day to hand in reports that were ultimately full of errors. Then she would spend most of her night taking overtime to fix those mistakes.
Janet joined her on her nights, claiming that she simply had work of her own to get done but Terra knew better. Her boss was staying to help her get better at her job. Despite claiming to have her own work, she was always available to answer any questions Terra had as well as always ‘just happening to’ finish her work at the same time as Terra so they would leave together.
Those long nights were both the bane of Terra’s job, and also her favorite parts. She was there because she was a fuck up, but she spent her nights chatting with Janet. Janet insisted that they be more friendly with each other, being some of the few women in the office. Sometimes she even brought a bottle of wine for them to share as they worked. When Terra refused, she simply stated, “Oh, please. Who’s going to get you in trouble? Me? I’m the one who brought the damn thing.”
Terra was relieved at the calming atmosphere Janet provided. Janet made her feel so at ease in the office. That she belonged. Even if she made constant mistakes. Months passed and eventually Terra got good enough at her job to no longer warrant the overtime everyday. But sure enough, whenever she did stay late, Janet was there to keep her company.
Soon the summer came around and Janet learned of the annual company retreat. Every year, upper management went on a retreat for a week to relax. A few employees were chosen by management based on performance to accompany them on the vacation.
It came to a big surprise to everyone when Janet chose Terra from her branch to accompany her. Her reasoning was that despite her rocky start, Terra showed drive and commitment to the job for her daily overtime and rapid improvement.
Terra almost rejected the offer. Surely there were others in the office more qualified and deserving of the spot. Others who had worked hard to excel, not she, who had worked hard only to reach mediocrity. But at the urging of her co-workers and Janet herself, she agreed to go. As they told her, it would be a great way to get her foot in the door with upper management for potential promotions. And of course the free trip to the tropics that counted as paid vacation was pretty convincing. And so Terra boarded the flight and chatted with Janet all the way to their destination.
Day 1 of 7
The first day of the trip had proven to Terra that she should have given her ticket to someone else. Janet disappeared to hang out with and discuss business with the other execs while the employees entertained themselves at the resort. Terra admittedly had trouble relaxing in work environments so she thought a vacation mixed with aspects of work, or at least the people from work, would solve her problems. Instead, this only made her more tense.
The first thing she noticed when introduced to the other employees was that she was the only woman amongst them. In fact she and Janet were the only women, period. The other employees also noticed this.
After they went around the circle introducing themselves, Terra could feel the atmosphere but hoped it was just her mind playing tricks on her. Standing around with nothing to do, one of the other workers suggested that they hit the beach. Thankful that someone put forth anything, everyone else agreed.
Terra checked into her room and slipped into a bikini that she thought was absolutely adorable. Her friends had picked it out for her just for the trip. They had jokingly insinuated she should use it to seduce an exec, which she shot down instantly. But she did buy the bikini. They were right about the fact that it flattered her in all the right ways.
On the beach, Terra discovered that her fears were warranted. The majority of the guys suggested they play touch football and that Terra be the ref. An obvious attempt to show off for her. After watching a few plays, Terra wandered off to be alone, figuring that would be better than dealing with that.
After a few minutes of standing in the shade, Brian, one of the employees who didn’t join in on the game, approached her holding two bottles of soda. Ah, he was the one who suggested we go to the beach. She looked him over. He clearly wasn’t as athletic as the other men, though she wouldn call him fat. He had more of a dad bod, clearly meant for power over speed. And he wasn’t bad to look at.
Brain wandered over and offered her a bottle. Terra took it. “Thank you.” She internally sighed. Here we go.
Brain joined her in the shade, standing a few feet away. “No problem.” He took a deep breath and sighed. “Look, I’m sorry I suggested we come out here.”
“Why? The weather’s nice and it’s a beautiful day.”
“I think we both know why. I wasn’t thinking and didn’t realize those other guys would hound you and all that.”
“Well I thank you for the apology Brain but I don’t exactly think you’re in the wrong here. If you hadn’t suggested this we would probably all still be standing in the lobby.” They shared a quick laugh.
“That’s true.” A minute passed with some awkward tension in the air before Brain shuffled his feet. “Welp. That’s all I wanted to say. Sorry for disturbing your obvious alone time. Just didn’t want you to think we are all like that. I’ll leave you to it.” He took a few steps and stopped. “Oh! I’ll also try to steer them away from this area when they inevitably come looking for you, so, feel free to take all the time you need.” And then we were off. He’s not so bad after all.
Terra spent her first afternoon of the retreat alone. After a few more attempts, the guys gave up hitting on her, seeing she wasn’t interested. Brian then suggested they go try some of the other women at the resort. As the pack wandered off to go hit on other resort-goers, Terra almost choked on her drink giggling at Brian, who gave her a huge smile and two thumbs up behind the group’s back. She gave him a thumbs up and mouthed ‘thank you’ to him.
Her faith in other humans restored, Terra genuinely enjoyed the rest of her day. She once even saw Janet and was flashed a smile from under her big sun hat while she talked with obviously important people.
As the day wound down, most of the resort-goers gathered in the hall for the buffet/dinner. Having revealed their true colors, most of the other employees sat separate from Terra. Most of them sat at their own little ‘boys club’ table, though one or two seemed to have struck gold and were sitting with women she had seen around. Janet sat at a big, important table with all the male execs, and thus Terra sat alone, picking at her plate until a familiar shape wandered over to her.
“How’s it going Terra?” At the sound of his voice Terra perked up. Maybe I won’t be ostracized for the entire week. She looked up and smiled at the man standing next to her chair.
“Oh, Hi Brian.”
He flashed her a smile and over exaggerated his next line, playing up the cheesiness of it. “Forgive me miss, but is this seat taken?” he gestured at the seat next to her.
She played along. “It has a few reservations but I can move some around for you.”
“Thank you.” Brian sat down next to her. “So… how was your day after the dogs lost your scent?”
Terra looked at Brian. She took a risk and told him the truth. She sighed. “Lonely”
“What? Do you actually miss the attention?”
“No! No. I don’t. I just also don’t want to be alone, you know?”
Brian surprised her by taking her hand. Well, less taking her hand and more placing one of his over hers. Terra thought long and hard in the second after. She tried to see any hint of ulterior motive in his face, his eyes. She couldn’t. In fact she could tell he was nervous that he had made a mistake in the action. She didn’t move her hand away. Maybe he actually isn’t like them. Then “I do actually. I’m sure you noticed the other guys didn’t exactly take to my… magnetizing charisma. After we walked off I spent the rest of the day alone, walking the sea shore, gazing at the ocean, all that jazz.”
“That sounds really nice, actually”
He released a dry chuckle. “Yeah, a real RnB music video, alright. And just like in those songs, I was lonely. So we have something in common.”
They had a nice dinner. They laughed, they joked, Brian shared some inside info on the other guys. It was a fun time. Terra thought she had made a nice friend. When the night truly settled around them, Terra noticed the changes. Those who had met other resort-goers were leaving the hall, probably to go ‘consummate’ their new friendships. Everyone else stayed in groups and started ordering drinks.
She didn’t particularly want to do any of those things and so she went to excuse herself to her room. She and Brian stood from the table and made to say their farewells.
“Thank you so much Brian.” She gave him a hug. She felt him tense as he didn’t expect the contact. After a second he returned. She kept talking as she squeezed. “I’m sorry if I was a bit prickly. Thanks for making me finally feel welcome.”
“No problem, Terra…” There was a lingering in his sentence, like it hadn’t ended yet. Oh no. He made up his mind. “We both felt a little left out today. It would be a shame to make that the new normal.” She felt a hand slide from her shoulder blade down to her lower back. “I think we can solve our problems of loneliness together. How about it? I’m certain I can make you feel even more welcome.” Why does it always turn out this way?
Terra pushed herself from the hug. She felt the tears well up in her eyes. “I should have known.”
“What? Wait? Why are you crying? I thought things were going well.”
“They were! Until you started thinking with your dick like the rest of them. I thought you were better than them, but you’re worse. At least they were upfront about it. You made me think you cared about me.”
“Terra I do ca-”
“Do you!? Who shows that they care about someone they just met by propositioning them for sex!?” She saw him about to respond and decided she didn’t want to hear it. She gathered up her things and stormed out of the hall, ignoring the eyes on her back.
She went up to her room and shut the door, then laid on her bed. She tried to hold back her tears. They aren’t worth it. They came anyway.
An hour or so later, she heard a knock on her door. How does he even know where my room is? “Go away Brian!”
The voice that answered back was a feminine one. “Terra it’s me.”
She wiped her face. “Janet?”
“Terra, open up. It’s hard to talk through a door.”
Terra got up from her bed and opened the door. As the voice suggested, her boss was standing there. When the door opened wide enough, Janet pushed her way in and wrapped Terra in a tight hug, squeezing her tightly. “Janet!?”
“Oh thank god you’re OK.” Janet released the hug but still held Terra by the shoulders, looking her up and down. Isn’t this a bit too close? “You are OK right?”
The surprise as to how personal her boss was getting shook her out of her sadness. “Yeah… um. Yeah, no, I’m fine.”
“Are you sure? You left in a hurry. And… Oh no, look at your eyes. You’ve been crying haven’t you?” She wrapped her back in the hug. “You poor thing.”
Terra tensed. Her arms started to rise to return it but she stopped. I shouldn’t do this. She pried herself from the hug. “Mrs. Johnson, you – we shouldn’t do this. Behave so casually, I mean.” Hopefully she got the meaning of my rambling.
Janet seemed to ignore her poorly put together statement. “But are you really OK, Terra?”
“Yes. I’m fine. Just some guys being dicks. Nothing new. Not worth worrying over.”
Janet once again surprised her by taking her hand in both of hers. Even though she felt it was wrong, she couldn’t bring herself to pull away. “That’s not true Terra. Just because that’s ‘the way things are’ doesn’t make it any less wrong. I’m here for you if you need anything.”
“Thanks, but I don’t think-”
“Terra I know we have the whole boss-employee thing, but there’s so much more to us than that. First and foremost we are human beings, with feelings. I can’t and won’t just stand by when someone I care about is in pain. Second, even though we are working together, we are women in a field dominated by men. We have to stick together. And lastly, I should shoulder some of the blame for this.”
“You? Why?”
“I should have warned you, or told the others to leave you alone or something. I’m used to being the only woman here, but like you said, I’m essentially their boss. They would never try something like that with me. It slipped my mind that you wouldn’t have that same safety net.” Her voice began to waver near the end.
Seeing Janet so distraught at her predicament filled Terra with sadness. “No. No it’s not your fault. You shouldn’t blame yourself for assholes. I don’t blame you at all.”
“Really?”
“Absolutely not.” This time Terra initiated the hug. She felt Janet squeeze her back and they spent a second comforting each other.
“You are too kind Terra.” They let each other go. “Tell you what. I’m going to make it up to you tomorrow, Terra. After I get rid of the execs it’s just you and me. Just like old times in the office. A couple of gals having fun. How’s that?”
Terra felt a wave of relief and happiness run over her. I won’t be alone all week. “I’d like that Mrs. Johnson.”
“Oh, please Terra. Save that for the office. This week, we are just co-workers on vacation. Call me Janet.” She reached into her bag and pulled out a notepad and handed it to Terra with a pen. “Here, write down your number and we can set up a meeting time.” Terra did as she was told and they said their goodbyes. When the door closed, Terra sat on her bed and turned on a movie, having forgotten about her sadness in excitement for the next day.
When she was winding down to go to sleep, her phone buzzed. Looking at it, it was a number she didn’t know. She read the message.
‘Hey, Terra. It’s Janet. I just wanted to make sure you were really OK after everything that happened.’
She typed back. ‘I’m fine now.’ She started typing something then stopped. That’s too far.
Janet didn’t miss her hesitation. ‘Are you sure you’re OK? What were you going to type?’ There was a pause. ‘Terra, talk to me. Please. I can’t help if you don’t tell me what’s wrong…’
I’m making her worry again. ‘Everything’s fine. I just… I wanted to say thank you for checking up on me earlier.’
‘Think nothing of it. After I take care of this last bit of business tomorrow we can spend the week truly having fun. Hopefully we can do more together than have me check up on you. See you tomorrow afternoon. ;)’
Terra reread the message a few times. She’s really nice. She shot back ‘I can’t wait! Good night.’ She hesitated a second before sending a second message. ‘:)’ She went to sleep that night with a smile on her face, excited for whatever Janet had in store for them.
Day 2 of 7
Terra spent her morning in her room, not wanting to deal with seeing everyone after the scene she made the previous night. She was content to do that until she had an epiphany. You know what? Fuck them. They are assholes and will be assholes whether I’m in here or not. Might as well enjoy my vacation. At noon she left her room in her bikini and hit the sand again, this time with her head held high.
After the first hour of turning away guys, she finally got the alone time she desired. That was until another shadow blocked her sun.
Terra was laying on her stomach, trying to tan her back when the new suitor cast his shadow. “Look, asshole, as I told every guy before you, and will tell every one after, I’m not interested.”
“So you aren’t interested in guys. Would you perhaps be interested in a woman?”
Terra sat up. Lo and behold, Janet was standing over her. She had her large sun hat on and a pair of dark shades. She carried a tote bag as she stared down at Terra. Her smile was almost warm enough to almost replace the sun she was blocking. And if the smile wasn’t enough, her body was definitely hot enough. Platonically, of course.
She wore a simple bikini. Its simplicity only highlighted her beauty. Terra never noticed through all the business suits, but Janet clearly kept herself in shape. Terra was surprised that those blouses could hide her breasts and overall figure so well. She was practically bursting out of her bikini top, and the bottoms dug just enough into her to show off ample flesh on her hips. She wore a beautiful pareo with a pattern of orchids. Hung low on her hips. Terra was speechless.
Janet laughed. “I was just teasing Terra. But maybe you are interested in the fairer sex?” She lowered her shades and offered a raised eyebrow.
Terra picked her jaw off the sand and shook her head. “No, no I’m straight. I just never noticed how pretty you are.”
Janet placed her beach towel next to Terra’s and joined her in lounging in the sun. “Good. That means the clothes work. It’s easier to get by day to day when you don’t show the men any more femininity than you have to.”
“That makes sense.”
“So Terra. How are you enjoying your vacation, you know after yesterday?” Janet offered a sympathetic look and placed a hand on Terra’s shoulder. Terra placed her own hand over Janet’s.
“I’m doing better, thanks.” Janet pulled her into a hug that Terra returned.
“Oh, no. Terra you are burning up!”
Terra only laughed. “Well, I was tanning before you got here.”
“Not without oil you aren’t. You’ll just damage your skin.”
“Oh. Well I don’t have any oil.”
“I do. Lay down, I’ll apply it for you.”
“Oh no. I couldn’t ask you to do that.” As she was talking, Janet simply pushed her back down onto her stomach.
“Well it’s a good thing you didn’t ask me, then.”
“But Mrs. Johns-”
“Ah ah ah. That’s for the office. Remember, we are just two friends on vacation. And friends don’t let other friends get sunburnt.” Some part of Terra wanted to resist but she couldn’t get through that reasoning. It’s not like we’re doing anything technically wrong. “Let me throw in a bonus. I studied a few years ago under a masseuse. Had some free time and I was bored. I’ll throw in a two for one. You get oiled up and a massage, free of charge.”
“Well… it’s hard to turn down such a generous offer.”
“Then don’t. Now lay flat.” Terra did as she was told and tried not to tense too much when she felt Janet swing her body over her legs, resting herself on Terra’s thighs. She did jump when she felt Janet pull the string to her bikini top and she felt the slack.
“Janet!?” She tried to rise but strong hands held her shoulders down.
“Relax, Terra. I know what I’m doing. You want to have as few of those nasty tan lines as possible, as well it would only get in the way of the massage.”
Terra mulled it over for a second. Being technically topless in public didn’t appeal all that much to her, especially due to the fact that she attracted too much attention as it already stood, but she also trusted Janet’s judgement. She hasn’t led me astray so far. “…OK.”
“Good. Now I’m going to apply the oil first, and then we can start the massage.” Terra Jumped when she felt the cold oil flow onto her back and tensed when she felt Janet’s hands start to spread it around.
She felt them start from the center of her back, gliding along her skin as the oil spread beneath Janet’s palm. She sighed at the nice feeling of the once cool oil warmed by Janet’s hands. Janet chuckled. “I haven’t even begun the massage yet. Are you really that pent up?”
Terra just groaned into her folded arms. “Mmmhmmm”
“Well I guess I better speed things up so we can get on to the main event.” Terra felt the hands gain in speed as they moved to cover her shoulders, neck, and lower back. Then she felt them return to her shoulder blades and pause. And then they each went outward, along her side and down the sides of her breasts.
“Janet!” Terra raised herself on her forearms to look back at the woman sitting on her legs. Then she remembered that people could see her chest and layed back down quickly.
“What’s the problem Terra? Just making sure the oil was evenly spread. Trust me. You really don’t want to miss any spots.”
“But – you just – we-”
“We what? I’m just applying sun tan oil to you. Besides, nothing’s wrong with a little skinship between girls.”
Terra was going to probably let out more flustered nonsense, but the look Janet gave her made her oddly calm. The smile Janet gave her held no ill will, as if the thing she did was totally natural. Maybe it was? “Just… warn me next time. Please.”
“Of course.” Terra relaxed on her folded arms again. Janet’s hands returned to her back and thankfully only her back. They slid up and cupped either side of her neck before sliding down her collar to her shoulders. She felt Janet trace the outline of her shoulder blades. All of these touches were light and the hands were gliding over her skin. When does the massage start? Before she could ask, she felt Janet shift her weight and she felt the thumbs dig into her. She couldn’t stop the moan as it left her mouth.
Terra tensed up again and flustered. “Sorry!” Again, the disarming laugh came from above.
“It’s OK Terra. Those noises are how a masseuse knows they are doing it right.” Terra relaxed, still embarrassed. “Might I add, you have a beautiful voice.” The massage continued and Terra tried her best to hold in any further noises but Janet’s fingers proved too good at their job. After her third full moan she gave up and fully relaxed, letting the hands do their work.
“You have very strong back muscles Terra.”
“I used to swim in school.”
“I see. Well even if you don’t swim now, that investment sure was worth it.”
“… For my muscles?”
“Well, yes. But I was mainly talking about…” The hands finished up on her shoulders and upper back and moved down, palms gripping her sides as the thumbs kneaded her spine. She let out a particularly loud moan at that. “Your body. It’s exquisite.” The embarrassment Terra felt then only partially came from the moan. Having Janet compliment her body so earnestly made her feel strange. But a good strange.
“Thank you. I still swim sometimes on the weekends.”
“Well maybe I should join you sometime. Lord knows I need the exercise.”
“That’s not true!” Her outburst surprised even her. “I mean, yes, some exercise can do everyone good. But you look beautiful, even if you think you don’t. It’s like… I guess the appropriate word would be thick.” She waited a second and realized how that could come off. “Oh, I’m not calling you fat I mean lik-” The now familiar laugh quieted her.
“I know what you mean Terra. I’m not so much older than you that I can’t understand the slang. Thank you for the compliment.”
Face now burning from more than the sun, she buried her head in her arms as the massage continued. After finishing her back, she felt Janet slide down until she rested on her ankles and applied oil to her legs. Terra allowed herself to enjoy the pampering. Janet’s hands felt so good that all else in the world vanished.
Janet worked her way up from Terra’s calves to her hamstrings, at times working out knots that felt so good Terra’s Leg shivered in her hands. An alarm Terra almost ignored if it didn’t have a tactile feeling with it. Janet’s hands were getting pretty high up on the back of her thighs.
“Terra, would it be alright if I went up higher? I want to give you a thorough massage and the glutes carry a lot of stress.” The question hung in the air for a few seconds, her hands paused just below Terra’s cheeks. That seems kinda personal… But it feels so good. And she already touched my breasts. It’s not like this is any worse. She wouldn’t do anything to me. Janet added. “Feel free to decline. Whatever you are comfortable with.”
“No, it’s alright.” She thought for a second. “Wait! You don’t have to like… take off my bottoms do you?”
“Only if you want me to.” The question confused Terra as she processed the words before the tone. Once she recognized it she could hear the warm, teasing smile. She really likes to tease people.
“I don’t.” She said it matter of factly, with a tinge of sass. How’s that?
“Maybe next time then.” She felt the hands rise up and cup her cheeks. The next few minutes were pure bliss as Janet’s hands kneaded the flesh. She couldn’t restrain those moans. She didn’t know just how many knots and kinks her ass could have.
“You have a very nice ass, Terra. I guess you can thank swimming for this as well?”
“Well, kicking is a big part of swimming so yeah. Lots of squats and leg presses.”
“Well they paid off.” Then they fell into a comfortable silence.
At some point, as she relaxed with her eyes closed, she heard the sound of shuffling sand as someone approached. Before she could react, she heard Janet speak, voice hard and commanding. A harsh contrast to how she’s been talking to terra. “We’re good. Thanks.” She heard the shuffling get further away.
“What was that?”
“Just some guy trying his luck. Nothing to worry about.” The information fed a feeling she had been attempting to ignore. The utter relaxation of the massage spread throughout her body and caused her to relax, but most of the pleasure pooled in her lower abdomen. It was another pleasant feeling along with many so she was content to ignore it. But hearing Janet defend her with such aggression, almost possessive, caused the feeling to grow into something stronger and confusing for Terra. What is this?
“Thank you Janet. I think I’m good now.”
“You sure Terra? I could probably work a few more knots ou-”
“I’m sure. Thank you.” She reached back and retied her top. And sat up.
“OK. Do you want me to get your front?” Janet held up the bottle. The question caused the feeling to surge.
“No, I can do it myself. Thanks for the massage.”
“You are very welcome Terra.”
After oiling up her front, both of then tanned in silence until Janet broke the tension with pointing out something stupid happening on the beach. They shared a laugh and chatted about nothing. At some point they went and got lunch, having had their fill of the sun. At Janet’s suggestion they ate in her room. Terra marveled at the fact that she got a suite all to herself. They watched movies on her couch late into the night before Terra went back to her room to sleep. Today was fun.
Day 7 of 7
Terra and Janet set into a routine for the rest of the week. They were inseparable, hanging around the resort during the day and watching cheesy rom coms at night in Janet’s room while sharing room service and drinks. Janet even when out and bought her a matching pareo, this one adorned with white lilacs. They even made it a game to see how many guys they would have to turn down each day. Janet was the winner and Terra couldn’t even begin to be jealous. Janet was a very pretty woman afterall.
On the final night, they decided to splurge, on the company’s dime of course, and order martinis and a few shots up to the room. What started out as fun quickly turned into an anxiety-laced minefield for Terra. I shouldn’t be getting drunk with my boss like this. What if I embarrass myself? What if I mess up and lose my job?
Terra started to gather her things, a slight sway to her movements.
Janet reaches out to steady Terra. “Are you alright?”
“I’m fine. I just need to go lie down. You shouldn’t see me like this.”
“You can lie down here. Terra.”
“I couldn’t do that to you. You’re my boss. I’ll just head to my room.”
“You can’t do that! What if something happens to you on your way?”
“It’s only down the hall. You can walk me there.”
Janet gave her a sad look. “But then I’ll spend the rest of my night worrying about you.”
“Really, it’s fine.” Terra took another step and stumbled but Janet caught her.
“It’s not, Terra. Remember, I’m still your friend until that clock says midnight. And as your friend I can’t leave you alone. Don’t think of it like a bother to me because it isn’t. Think of it like a … sleepover.”
“A sleepover?”
“Yeah, a sleepover. We don’t have work until a few days after we get back anyway and our flight is pretty late in the afternoon. We can stay up and watch movies or something. And you’ll be here so I can make sure you’re OK.”
Terra’s head worked slowly to process her words. It was true that she didn’t want to leave yet. And she would feel safer if Terra was with her. And Janet seemed adamant on the fact that they were friends. She’s just looking out for me. “Yeah… OK. I’ll stay.”
Together they watched movies and joked until late. Terra even had a few more drinks, though these were just beers instead of liquor. And then it came time to hit the hay and she realized that there was only one bed in Janet’s room. Of course there is. It’s a master suite. Terra was about to voice her concerns when Janet convinced her to stay once again by saying of course they shared a bed. How else would they gossip like a true sleepover?
Hesitantly, Terra got into the bed while Janet entered from the other side. She tried her best to ignore the feeling growing inside of her. The same one from the massage. They talked for a while, a foot or two between them. They talked about nothing. Memories, experiences. Somehow the topic got to sex, Janet asked her about her exes and they compared them to her husband, and Terra started to worry again. Janet assured her this was all a normal part of girl talk. I guess that’s fine.
After a while, there was a lull in the conversation. Then, out of the silence, Terra heard Janet ask, “Have you ever been with a woman before, Terra?”
The question blindsided Terra. She was thankful that the room was dark, but the darkness only highlighted her other senses. She recognized by Janet’s smell and the feel of the bed that Janet was close. Really close. She could smell her and the alcohol on both of their breaths.
“No.” There was another pause.
“Would you like to?” The question hung heavier than the last. And again, the gap between them seemed to have gotten shorter. She could feel Janet’s breath on her face and could see her eyes in the darkness.
“I-I told you Janet. I’m straight.” ….Right?
“Are you sure? I didn’t hear a ‘no’. Besides, maybe you’re like a nice piece of spaghetti. Straight until you get wet.” She let her joke hang in the air for a second. “It’s better to try it and find out for a fact rather than wondering what could have been.”
Terra tried to change the subject but the best she could manage herself was, “Have you?”
“Yes, a few times. Would you like to try it Terra?”
“But you’re married.”
“My husband and I have an arrangement.” Terra felt movement and felt one of Janet’s hands rest on her hip. She didn’t move away from it. “I meant everything I said, Terra, you are a beautiful woman and a good friend. I want to share this experience with you.” Terra’s head was swimming. The alcohol, the smell of Janet, the way the hand on her hip made the feeling in her gut surge. It all felt so right and yet it felt strange.
“I-I I don’t know.”
“What woman hasn’t experimented a little with her friends? Practice kissing, maybe a little heavy petting?” The hand moved down and reached around until it caressed her ass.
“I haven’t.” Some small voice in her head was screaming at her. Why wasn’t she resisting this? She’s straight and always has been. But this feeling was undeniable. One of them had to be wrong.
“Well I’d say you are long overdue then.” She felt Janet move forward until their fronts were pressed against one another. The heat from their bodies mixed and made its way down to Terra’s groin. She heard as well as felt Janet whisper, “Being with a woman is completely different than with a man. Sure a man may know how to wield his tool. But a woman has a more … intimate knowledge of what another woman wants. What she needs.” Terra hesitated again. “I won’t press you Terra. You can say no and we can go back as if nothing happened. I just want to show you my appreciation for your friendship and open your eyes to a new world.”
Terra’s internal debate was surprisingly short. Janet was making a lot of good points. What harm could a couple of friends fooling around cause? And if she had to pick a woman to… experiment with, it would be Janet. If she’s half as good at this as she was with the massage… Terra mumbled her answer.
“What was that? I couldn’t hear you.”
“I said… OK.”
“That’s good. It’s OK. Let me take the lead. Just relax.” Terra expected her to touch her breasts or grip her ass or something more sexual. Instead the first thing Janet did was place a kiss on her lips. A long, sensual one. Terra tensed up at first, but Janet’s soft lips and her hand on her ass caused her to relax into it and even moan into it.
When they separated Terra asked, “What was that for?”
“I want you to get the full experience. That way you can decide if you truly like it or not.” Without any more words Janet began to truly get into it. One hand massaged Terra’s ass while the other slipped under the t-shirt she wore to massage her breast. After another kiss, Janet moved down to lay kisses up and down Terra’s neck.
Terra submitted fully to Janet, the pleasure she promised was delivered and she wanted more. The feeling in her gut condensed into a knot and it needed release. After a few minutes of getting her warmed up she felt the hand on her ass move back around to the front and start to slip into her boy shorts. Terra took in a breath and held it, tensing her abs.
Janet stopped the hand, looking into Terra’s eyes. “Everything alright?”
“Yes… just preparing myself.”
“Take all the time you need.” The hand paused its descent, but notably it also didn’t go back up. It just sat on her pelvis. With the hand being so close, something within Terra wanted it to go down. Needed it. She gave Janet a silent nod.
The hand continued downward and when it finally touched her, she fully relaxed. Her fingers were nimble and precise. She was right about a woman knowing how to please another woman. Her fingers immediately attacked every part of her folds that made her go crazy. She moaned and clutched onto Janet as she worked. Her fingers found their way up to Terra’s clit and Terra could feel her peak coming. Then the fingers were gone and Terra was left wanting more.
Before she could ask why, Janet silenced her with a shush and a finger to her lips. The same one that she was just fingering her with. My lips feel wet. “There’s much more I can show you.” That smile came back. “I’m about to rock your world, Terra.”
With that Janet’s face disappeared as she moved under the sheets, moving downwards. Is she about to? She felt her shorts peeled off and then she was bare beneath the sheets. Terra was on her side, she felt Janet open her legs and move closer. She positioned her head resting on Terra’s inner thigh and closed the outer one on top of it, sandwiching her face in Terra’s crotch. The anticipation caused time to slow down as she felt Janet’s breath on her. And then she felt the tongue touch her.
The tongue had barely made a lap. A single stroke up her slit that ended with a flick of her clit set her off. She reached down and gripped Janet’s hair as she skyrocketed out of her body to cloud nine. As she convulsed, some far away part of her recognized that Janet’s tongue did not stop, continuing its motions to keep her up there longer.
When she finally came down, she expected Janet to stop. To come back up for air. Instead she hooked her arms around Terra’s thighs and went harder, mouth not leaving her crotch for a second.
All Terra could do was lay there and tremble as Janet brought her to three more of the best orgasms of her life, each one better than the last. Finally, Janet unlatched herself and came back up.
Having lost all her inhibitions, this time Terra kissed Janet, using her tongue and tasting herself on Janet’s. Terra tried to express all her feelings with the kiss. It lasted several minutes until they broke apart due to lack of air.
“I take it you enjoyed it.”
Terra was breathless “Yes. It was – you were -are amazing.”
“Thanks, I try.”
Terra then had a moment to think semi-clearly as they looked into each other’s eyes. And in that moment she panicked. Janet had just shown her the time of her life and she knew she couldn’t do the same. She couldn’t even muster up the courage to go down there herself.
The guilt of her inadequacy made her get choked up. Janet cupped her face. “Terra, sweety, what’s wrong?”
“I’m sorry. It’s just. You were so nice and did all of that for me and now it’s your turn but I don’t know if I can return the favor. If I’m-” she was shushed again.
“Stop right there. Don’t ever apologize for that. If you aren’t ready then you aren’t ready. We can move at your pace.”
“But I can’t just leave you with nothing! I want to do… something to you.”
“Then you can just use your fingers. If you want to. You don’t have to. This was just to show you the wonders another woman could bring and I would say I succeeded.”
“I could do that.”
“OK Terra. Whenever you are ready. Feel free to stop if it becomes too much.”
Hesitantly Terra placed her hand on Janet’s stomach as they looked into each other’s eyes. Slowly, her hand traveled down until she got to the hem of Janet’s panties. With a deep breath, she entered the unknown.
The first thing she felt was hair. A good amount of it. She hadn’t noticed it when they were on the beach. She must keep it pretty trimmed. Then, as she moved down, her finger tips grazed Janet’s outer labia. Janet gasped and Terra looked at her face to see if she was doing it right. All she got was a nod from Janet, so she continued.
Just like she did to you. And what you do to yourself. Her fingers poked and prodded Janet’s pussy. Terra judged her progress by Janet’s reactions. Janet gave her supportive moans and nods whenever she did anything right.
Her voice came out in breaths. “You’re doing great Terra. This feels so good.” Emboldened by her words, Terra worked harder and faster, moving her fingers with more confidence. Janet continued to feed her compliments as her breath grew more and more labored, obviously enjoying herself. It made Terra happy that she could bestow at least a fraction of the pleasure Janet gave her back.
Soon, Janet learned forward, placing her forehead against Terra’s and stared deeper into her eyes. She reached down and grabbed Terra’s wrist and raised it slightly so that her fingers were on her clit. “Please Terra. I’m so close.”
Terra obliged, lost in her boss’ eyes as her hand moved to fondle the clit. Janet started lightly thrusting her hips in time with the movements, soon growing into almost full thrusts as she tried to grind herself against the hand as it pleased her. Their eyes never parted as Terra watched her approach the edge.
“Right there Terra. Right there. Oooooh I’m so close. Sooooo close. Don’t stop. Please don’t stop. That’s it. There it is. You’re going to make me cum Ms. Underwood.” With those words Janet began to convulse. One hand reached around Terra’s head and kept their heads together as she came. The other held Terra’s wrist still as she ground herself against the hand.
Terra had a front row seat to her friend’s orgasm and the only thing she could think was how beautiful it was. Her face contorted in a pleasant smile as her eyes shone in ecstasy, still aware and looking into what felt like Terra’s soul.
When the orgasm subsided, Janet kept Terra’s hand between her legs as she leaned in and they shared another kiss, just as tender as the first. Then they both laid in the post-orgasmic glow, staring at each other.
Terra had to ask. She had to know. “So, what does that make us now?”
“As I said, Terra, we are friends having some fun. Tomorrow we go back to being boss and employee, but until then, in this bed, we can be whatever you want us to be.”
Satisfied with that answer, for now, they held each other until they went to sleep.
First day back to work.
Terra sat at her desk with a new lease on life. The experience she shared with Janet days ago still played on her mind nightly. Who knew women could be so… nice. She flashed a smile to Janet when she walked by. Janet barely acknowledged her existence, giving a curt nod back before returning to her office. Terra just stared after her, confused and slightly hurt. Then another woman in the firm sidled up next to her.
“She got you too huh?”
“What?”
“Let me guess. You two had a wonderful week on the trip and on the last day shared a ‘wonderful experience’ together.” She air quoted the words.
“Yes, how – how do you know?”
“Because we all did. Each year she takes one of the new female hires with her on the trip. She gets close to you, then on the last day, she strikes.”
Terra’s life started crashing down around her. I thought what we had was special. “But, but that’s not right. She can’t just do that. Surely HR or something would get her in trouble!”
“Shhh!” the other woman looked around before continuing. “I would keep that talk to yourself if you know what’s good for you. HR won’t help you.”
“Why not?”
“You know she’s married right?”
“Yes.”
“Yeah, married to the owner of the company. Any complaint against her gets thrown out and the one who complains gets axed.”
“But that’s – it’s not right.”
The other woman just sighed. “You’re right. It’s not. But it’s how things work around here.” With that she walked off, leaving Terra to deal with her feeling alone. That night at overtime, Janet didn’t stay. Or any night after that.
Poker night, Janet’s house.
Janet sat on her husband’s lap as he played a hand. Around the table sat several men, the same execs that went on the retreat. The ones that posed as the other “employees” during the retreat. She held up her phone and showed them the selfie she took of Terra sleeping soundly next to her in bed.
There were groans of annoyance as several men around the table tossed wads of cash towards her.
“Damnit.”
“For the love of…”
Brian spoke up as he gave his money. “How do you do it? I thought for sure I had this one.”
“All it takes is a woman’s touch, boys.” For the tenth year in a row, Janet had won the little game they played every vacation.