Lesbian Surprises at Work Retreat

This is the story of recent event from my ongoing sexual journey. My name is Tina, and I've worked at my company in San Diego for the last 12 years. My job is in a male-dominated industry, but even at only age 35, I've managed to find success and work my way up.

Fortunately, there are a number of successful senior women in the organization, and I feel like I've benefited greatly from their support and sponsorship. They always seemed like a close-knit group, and I admired their connection with each other.

I knew that a small group of these successful ladies would sometimes do their own offsite events, just women, and only leaders or those about to take that step. I always thought it was so great that they could support each other and take care of one another.

You can imagine how excited I was when my mentor Cathy mentioned that they were going to have a get together this summer, and she wanted to know if I would be interested in joining! I was thrilled! This could be the next step for me, and let's face it, women aren't always that supportive of other women moving up in an organization. But this felt so different!

My partner Tom has always been incredibly supportive of me and my career! We have a great relationship, and since we both work so hard during the work week, we usually protect our weekend time together.

We enjoy travel, cooking together, visiting wineries, and quality time. That includes of course a healthy sex life, although perhaps less often than back in our honeymoon phase. When we are intimated, It's always great, and we even regularly enjoy watching porn together. My porn tastes have evolved over the years, from simply watching couples having sex, to group sex, swapping, and of course lesbian scenes.

In our fantasy talk, Tom and I imagine swapping, with each of us having sex with new partners. In those moments of course, we talk about me enjoying my first lesbian play. That seems to be the way most swinger stories start, right? With the men watching the women? Things often proceed from there!

I've never had a true lesbian encounter. Like many girls, I kissed a female friend or two while drinking at college parties, usually egged on by equally drunk guys. But that's it! I have to admit though that the fantasy of lesbian sex has often aroused me, particular getting eaten out.

I love when Tom licks me, but I'm sometimes shy about it. Does he like it? Is it kind of gross for him? He says he likes doing it, but again, I'm sometimes hesitant.

I always figured a woman knows a woman, and that would make oral sex between women more normal. We know about our bodies and that doesn't seem gross at all. I've often fantasized about being pleasured orally, but would I do it in return? It's all just fantasy, and in that mind frame, of course I would! I'm not sure why I just shared all that, but it felt like the right time to do so. Now, back to the story!

Tom and I discussed the invitation. Again, while I hate sacrificing our weekends together, he has always been 100% supportive. My career was important to me and to him as well, and we knew this kind of networking is huge! Plus, I've gotten to know some of the women who were invited, and they've been fun people to work and talk with. Accepting the invitation felt like a no-brainer!

Cathy told me more about the details. The plan was to rent a nice house out in the high desert. We'd share food, talk, spend quality time. She of course mentioned the property would have an exquisite pool, and we'd all mix and share our favorite drinks.

It really sounded a lot like my "girl's weekends" that I used to do with college friends in the first few years after school. That was before work and marriages took over for most of them. Having kids really meant they were no longer available or even fun for that matter. Always busy and always stressed!

I intentionally have decided not to have children, and with many of my friends now occupied, I have to admit girl time with drinks by the pool was something I really missed.

I was excited too when Cathy told me Jane was going to attend. Jane was the highest-ranking female in the company, based out of New York. I'd met her only a few times at work events, but I knew she always worked behind the scenes to help me receive promotions and raises. She'd be flying into town for this event.

Age or appearances don't matter of course in a work context, but I can share a bit. I believed Jane was probably in her early 50's but could easily pass for her 40s. She was thin and fit, and always kept herself polished. She had long been a mentor to Cathy, who I was in her mid-40's. She wasn't as fit as Jane, but she was pretty and a bit curvier. These were both key people for my career.

Two other women were going to attend. One was Sarah who was probably in late 40's, and she led the central division. I didn't know her that well, but she was also important in the company. She was very driven yet still very patient and kind. Many of these successful women really achieved, whether in their careers or even in terms of keeping themselves together. It seemed like being thin and fit were important elements to career success! I know I believed that and worked to achieve that standard.

The fifth person was Gloria, and I didn't know her really at all. She was based in Phoenix and was recruited to the company just a couple years ago. With a background that included a couple decades of work experience, she was probably in her early or mid-40s. But again, her work photos didn't make her look nearly that old. She was Latina, which gave her a different look from the other three white ladies. I'm actually half Asian so it was nice to have a little more diversity in the group.

We had selected a late summer weekend when the desert would be hot. The pool would be great, and I was looking forward to the event. As it approached, I considered what to pack. Since this was my first time, I went to my mentor Cathy to ask what to bring. Would we be going out to any fancy dinners? Mostly staying at the house? Those sorts of things. I knew they had done several of these trips over the years, and I wanted to fit in.

I saw Cathy in the office and pulled her aside. I has been told not to share with others that we were planning this event or that I was invited. It was never good to make others feel jealous. I only knew about past get-togethers because Cathy had told me about them recently in strict confidence. I quietly asked about plans and dress code.

"No need to worry about all that," Cathy told me. "We won't be doing anything fancy. No need to show off. We'll probably just stay at the house. It's a bit outside of town, so we'll have our own food and drinks. Consider it a 48-hour relaxing retreat! That's how we like to do it. Just unwind and have fun with each other."

She smiled and gave me a little wink. The lack of pretentiousness sounded great to me. Yet I knew I'd want to present a professional image while still a fun one. It was a careful balance to be sure!

I needed to be taken seriously but not too seriously, so as to fit in! I packed some sun dresses and somewhat conservative two-piece swimsuits. I wasn't a one-piece kind of girl but also wasn't the type to do G-string bottoms. I like to be classy, and I chose carefully yet confidently.

The weekend finally came, and I said goodbye to Tom. He told me to have a great time, and we agreed again that this was a good career move. Cathy had told me the rental's location was a bit remote and cell reception was spotty. Tom and I said our goodbyes knowing we may not connect much for the next couple days. We usually spoke often when separated, but a short time away was okay. We hugged and kissed, and off I went.

The drive was about two hours, and texts were going back and forth amongst the attendees. Flights were on time and people were getting excited. As my drive was concluding, I indeed noticed my cell reception was basically gone! I managed to do a quick text exchange with Tom to let him know I was arriving safely. We exchanged "I love you!" notes and figured we'd connect again when we could.

As I pulled up to the house, the front looked amazing. Modern, well kept. This was where I'd spend the weekend, with a group of very successful senior women in my firm. I felt a wave of nervous energy wash over me. These were important people. I needed to fit in and be seen as one of them. I didn't know what to expect, but I didn't want to make any bad impressions.

I took a deep breath, headed to the front door, and knocked.

I heard Cathy come running to open it. Throwing it open wide, she smiled and let out a big greeting. "Hello!! So glad you made it!" she said as she gave me a big hug. "Let me help you!" she continued, grabbing my bag, and placing it to the side.

"Thanks Cathy! Thanks for inviting me," I said. "This place looks amazing!"

"You have no idea!" she exclaimed. "Let me give you a quick tour". She then led me around the house, which had a modern and sultry feel. There were several bedrooms, all with king beds. The master was large, and someone's bag was already in it. "This is Jane's room," she said. "The boss always gets the best room. She always gets what she wants!"

"Of course," I said. "Makes total sense. Where is everyone?"

"Right here!" she said, as she opened up a door to the pool area. It was beautiful, just as promised, and all the other women were already out there. "Hey everyone," said Cathy, "Tina is here!!"

I heard them all let out high pitched "yeahs" as they rushed over. We exchanged warm hugs. Jane embraced me first, saying, "Welcome, so happy you are here!"

Sarah hugged me next. "Hi Tina, welcome!" she said. She stepped back, noting the little sundress I chose to wear. She tilted her head down and to the side a bit. "Well, don't you look great!" I felt a little shy, but responded with feigned confidence, "Thanks! You do too."

The last person was Gloria, who was the only one wearing a swimsuit already. This was our Latina coworker, with dark features, and a great tan. Her white bikini really popped, and I have to admit, she looked really amazing. Girls notice such things of course.

"You remember Gloria, right Tina?" asked Cathy. I smiled and nodded.

"Hey Ms. Thang, good to see you!" exclaimed Gloria, using surprisingly casual language. She opened her arms wide, closed in and gave me a huge hug. I could feel that her skin was warm and a little sweaty. It was a big hug, and I felt her breasts squish against mine. It felt a little bit unusual, since we didn't know each other that well. I could tell that she had been drinking, which probably made her friendly.

"Okay, now that we are all here, let's get comfortable!" said Cathy. "Gloria, can you make some more Margaritas?"

Gloria nodded, "Oh you know I can, mama!" She was clearly buzzing, and everyone's mood was light.

"Okay girls," said Jane, "let's get comfortable. Meet back in five minutes!"

I found one of the open rooms, quickly changed into my light pink bikini, and headed back out. All four of us rejoined Gloria, who was at the blender mixing things up. Everyone looked surprisingly good. Again, I was clearly the youngest there, followed by Gloria. But everyone looked fit and kept together. I slowly realized that none of the group was married, and none had kids that I knew of. These were all hard-driving career women. Type A personalities for sure.

Drinks were ready and served all around. "Cheers!" reverberated as we settled into some lounge chairs near one another. It was late afternoon, so we had just a little sunlight left. The temperature was perfect, and the vibe was great. The next couple hours flew by. Gloria kept playing bartender, and no glass was ever left empty for long. These ladies knew how to let loose!

The conversation was easy, and I learned a bit more. As I thought, no one in the group was married. There wasn't much talk about significant others, and I believed Tom and I may have been in the longest and most serious relationship. And again, none of us had kids, so no stretch marks or strained physiques. I found that to be a little unusual, but it was another commonality that helped us all bond.

Gradually, we moved inside and towards the kitchen. It was time for dinner, and there was catered food that just needed to be reheated. That didn't take much effort so we could continue chatting and drinking. It was warm inside, and we all stayed in our swimsuits. It was quite fun getting to know these ladies better. As mentioned, I had lost contact with many of my girlfriends from school days, so it was nice to have some quality girl time.

The conversation was generally fun and light, but it did sometimes shift to our work and careers. I could summarize by simply saying this group of women prided themselves on having a special bond, looking out for each other, and helping find better roles and pay. That's exactly what I expected to hear and what made my choice to join the weekend so important. I couldn't wait to validate that with Tom! The time away would be worth it. But my cell phone was indeed totally without reception. I'd have to wait a couple days to reconnect with him.

The girls were definitely getting a little drunk now. I heard conversations skew to workout programs and how folks stay so fit. Another funny similarity was that we all used one of the really popular home cycling products, the cult-like one, as some joke. These ladies were classic overachievers, which perhaps explained how they all stayed in great shape! We had quite a bit in common.

I overhead more comments, like Sarah telling Gloria, "Girl, you look so good. So fit!". Gloria responded, "Thanks Sarah, you too. Everyone here looks great."

I heard Cathy add, "But Gloria, come on. Look at that trim waist, with those breasts though. C'mon!"

Gloria laughed, and responded, "Oh these? Yes, I thank my mom for these everyday," she replied. She then playfully put her hands on their sides and squeezed her cleavage together. We all laughed. It was fun and carefree, and admittedly kind of hot just sitting here with all these attractive women.

I started noticing little winks and eyebrow raises, conversations where people were leaning in a bit more, using softer voices. I didn't think too much of it at the time.

Then Jane started speaking louder to get everyone's attention. "Ladies, thanks so much for joining another of our special weekends. It's so great we can have these bonding experiences." She looked contently at each person one by one, and then focused on me. "And a special welcome to Tina! Our new up and comer!"

"Ah, thanks," I replied, "it's great to be here. You've all been so nice and welcoming. I'm having lot of fun!"

Cathy looked at me, put her hand on my thigh, and squeezed slightly. "It is really great to have you here," she said.

Jane spoke up again, "And while the best part of the weekend is about to start, I just wanted to remind everyone that this trip, this weekend, these times... are just for us and no one else." Everyone smiled and nodded. "This is the circle of trust, a special sisterhood," Jane continued. "A place where we can be judgment free, be ourselves, and just enjoy each other. It's our time and not for anyone else to know about. Right ladies?"

The group confirmed, saying "Yes", "of course", and "absolutely." I of course nodded my head too.

While I knew some people might get jealous at us being here and not them, I kind of wondered what Jane was talking about. What was the best part of the weekend? What was to be so secret?

It didn't take long to find out.

Cathy was sitting close to me on the couch, on my right side. Jane had been standing, but she soon sat next to me on my left side. I could also see that Sarah and Gloria were sitting close together on the loveseat across from us.

Cathy said to Jane, somewhat jokingly, "That was a great speech, coach, well done". She smiled and leaned forward across my body and toward Jane.

"Okay smart aleck, laugh it up," Jane said. She leaned forward as well, and in that moment, the two kissed! It was at first a peck, and then they pressed their lips together for a few seconds and much more intensely. My eyes blinked quickly, and I felt a bit stunned!

Was that what I thought it was? Is this what this special group does together?

The two broke their kiss, and Cathy turned to me and smiled. "Surprised?" she asked gently.

I wasn't sure what to say but finally muttered, "Ah, yeah, I guess so? Not sure exactly."

Jane put her hand on my left thigh, and I looked at her. "It's okay, Tina. No judgement or pressure here. We just like to be ourselves," she said softly. She squeezed my thigh lightly, moving her hand softly and delicately. "We don't invite just anyone into our group. We like you and want to do good things for you," she continued.

I heard Cathy say, "Yeah Tina, we think you are a perfect addition." I looked over at her. "I think you are really pretty," she said. We looked at each other for a moment, and then I felt her right arm reach across me and slide around my waist.

She leaned in, whispering, "I've wanted to kiss you for the longest." And our lips met. First just a little kiss, then she pressed harder. Squeezing her arm around me tightly. She opened her mouth and pushed her tongue into mine, softly at first, and then harder. I responded in-kind. That's just what one does when kissed, right?

I felt a similar nervous rush like the first time I kissed a boy as a teenager. But her lips were softer, her tongue delicate. And my face felt flushed. My mind blanked a bit. Am I really kissing another woman? My mentor?

Our kissing continued for several seconds, and then she pulled away. She smiled a wide smile, and I coyly smiled back. I felt another wave of nerves hit me.

"Ah, that's so hot," said Jane, "You too are so cute together." She patted my thigh and slowly stood up.

At that point, another thought hit me; not only did I just kiss a girl, my mentor, but I also did so with other people in the room. That included Jane, the most senior woman in our company, but there were two other women there! Were they seeing this? What were they doing? I quickly glanced around the room.

My eyes set upon Sarah and Gloria, sitting together on the loveseat. They were locked in a kiss as well! They were in a full embrace, pressing against each other. I had never seen two woman "hooking up" like that in-person, and admittedly, my pulse quickened. What was going on??

I watched as Jane moved toward them, sat on a chair, and started watching the show. Sarah and Gloria were quickly becoming more impassioned. Kissing more frantically, hands exploring. Sarah reached around and soon undid Gloria's bikini top. Her naked breasts were now in full view, and they were round and firm. Sarah moved her mouth to a nipple and stared licking. Gloria reached around and took Sarah's top off as well, and the two pressed their breasts together. Jane looked on and smiled.

Cathy resumed kissing me and her hands started exploring. Rubbing my thighs. Moving up and squeezing my breasts a bit. My head was in a daze. This felt so wrong but so right, or just really hot.

I was conflicted. I couldn't believe my female mentor was making moves on me. I couldn't fully digest that perhaps this was the "best part of the weekend", to use Jane's words.

Things moved along. Cathy and I quickly matched the progress of the other two. She pulled her own top off, and then quickly removed mine. I was now topless, kissing another woman, whose hands were roaming over my body.

Just then, I heard Jane say, "Oh yes, ladies. You are all so sexy! I love seeing all my ladies playing together!"

I found that phrasing odd, but in reality, Jane was the primary driver of all of our career progress. She looked out for us and helped us get promoted. In many ways, we were indeed "her ladies". Perhaps enjoying scenes like was one benefit from all her hard work on our behaves.