First Lesbian Experience


Tina’s first-Time Lesbian Experience

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It was the summer before college began and Tina was aboard a boat for the first time in her life. She had to get used to it, however, as the young girl was going to spend the next 8 weeks on that boat. There was a lot of time spent on land, of course, but she was going to be working on the boat about 90% of the time. It was one of those summer jobs, that sounded like a dream, at least to young people. The work wasn’t too hard, basically being a waiter and a cleaner for very wealthy people, as they floated around the Caribbean. She didn’t have to drive the boat or know anything about navigation. The gist of it was: rich people would rent the boat and the crew of 9 people would make sure that all of their needs were met. Everyone on board had a job, for which they were well compensated. On top of that, there was a lot of traveling and fun involved. Tina first heard about the gig from a high school friend. The girl recommended her and a few weeks later, she was on the boat. It was a great way for her to earn some money before college, and the idea of traveling around the Caribbean enticed her. It was a little intimidating at first, however.

“Hey, Tina, right?” – The captain asked, once she got on the boat. “Yeah, that’s me.”

“Ok, great. Let me show you around. This is the deck.” – it was a large space, with a beautiful wooden floor. There was a table outside, as well as a living room-like area, with a couple of couches and a coffee table. There was also an inside part, with a kitchen, dining table, and another living room-like area. It looked like a very well-designed and expensive apartment. – “The guests will spend most of the day here. You and another girl will serve them, things like drinks and food, during the day. There are 4-hour shifts, and you will rotate. It is a lot of work, but they also tip nice, so I’m sure you will manage. I will explain the details later. Let me show you your cabin.” – the captain led her down, inside the boat, next to where the engine was. – “You are lucky, you are going to get a single room.” – he said, as he opened the door to her cabin.


It wasn’t much, but at least she didn’t have to share it. It resembled a 7-foot cube, with two bunk beds. At the side opposite the door, there was another door, for the bathroom. The toilet and shower were in the same, cramped space, that resembled an airplane toilet. There was a small TV, mounted to the wall, but it was kind of uncomfortable to view from the bed. Overall, it was a small, claustrophobic place, but Tina didn’t expect anything else. It was just for a couple of months anyway, and she did need the money for college. The captain let her unpack her belonging, get in her uniform, after which she was meant to get back on deck.

Once she was up, Tina got to meet the rest of the crew. Mostly guys, a bit older than her and with more experience on boats. She was a little intimidated, not sure how life out on the sea would be, but she knew that coming out of her comfort zone was a good thing. Everyone so far was nice, and the captain did a good job at explaining the work. There wasn’t that much to it. She was a glorified waitress during the day and a bartender during the evenings. In the morning, they had to clean the deck, but aside from that, there wasn’t too much to be done. It wasn’t the toughest job in the world.

Despite feeling secure, the 18-year-old was intimidated, when the guests arrived. There were 7 of them, men and women. It was obvious from the way they dressed, with designer clothes, holding designer bags, that everyone was very rich. A yacht like that one cost hundreds of thousands of dollars to rent for the month and these people were gladly paying that. The men were older, in their forties, with some white hair showing and a couple of them had bellies. The women were all gorgeous and seemed younger. The crew was standing in line, shaking hands and introducing themselves to the guests.

“Nice to meet you, I’m Tina.” – it was the youngest looking woman, who was wearing a flower pattern sundress. She was probably in her late twenties, tall and athletic. Her hair was blonde and a little curly, while her eyes were hidden behind classy-looking sunglasses.

“Hey, I’m Rajini. How old are you, if you don’t mind me asking?” –she was the only one that interacted with her.

“I’m 18.”

“Wow, young. I like that. Well, I am sure we’ll see a lot more of each other Tina.”

That woman was the only one that said anything to her, besides hello. Overall, the guests were not very interested in the staff. They probably had vacations like this all of the time and didn’t even bother too much with being nice. Immediately, they went to their cabins, which looked like 5-star hotels, and unpacked their bags. The captain started the boat and they set off. Tina had the second shift, which meant she didn’t have much to do, besides retreat back to her claustrophobic cabin. She decided to take advantage of it being private. She was going to masturbate.


Tina felt a bit weird about masturbating in her cramped room, on a boat full of strangers, but it was a guaranteed way to make herself feel better. The 18- year-old knew herself well and had brought her favorite sex toy on board. She liked to start by turning the vibrator on a lower setting and then stimulating her nipples. There was a slight, buzzing sound, but because of the sounds of the water, no one could hear her. The walls were otherwise paper-thin, so she had to turn on the TV, to cover for herself. She put the egg-shaped toy under her shirt and teased both her nipple, while her other hand, gently caressed her inner tights. After a while, she switched it up. The egg began teasing her inner tights, while she used her free hand to massage and pinch her breasts and nipples. When she was sufficiently wet, Tina turned the power of the vibrator to the max, moved her panties slightly to the side, and inserted it into herself. Now that it was inside of her, she could feel the strong vibrations, against her warm and soft vaginal wall. Tina enjoyed playing with her clit, rubbing it, and fantasizing.

The young girl didn’t have much sexual experience but liked to imagine getting fucked. The small cabin was so tiny, it no one else could fit, but she could see herself getting fucked on one of the beds the guests had. She liked to see herself getting dominated, being punished, and told what to do. After that, she just thought about the situation she was in. There was something very kinky and sexy about being on a boat, masturbating with a vibrator inside your pussy, while people were working a few feet away. She liked the potential risk of being caught, it was naught. What would they do? Spank her? It was the kinkiness of it all that she loved. The only problem was she could not moan and groan, at least loudly.

She did breathe heavily and often let out a quiet gasp of pleasure but did not want to push it too much. She was starting to get into it, sweaty and aroused, her pussy drenched. Tina had to shower after that, she was a dirty girl. She loved imagining getting fucked herd, despite never actually experiencing it. For now, just her fantasies were enough. After a few minutes, the orgasm arrived. Tina could hardly stop her leg from twitching and often let out a moan that was perhaps too loud. After finishing herself off, the girl took out the egg, cleaned it up, and locked it inside the cupboard.

Masturbating at work made her feel more relaxed and satisfied with her career choices and it was so much sexier than doing it at home. The risk of getting caught by the rest of the crew, or worse the guests made the whole thing extremely kinky. Just the thought of it got her wet and horny. She was lucky to have a single room. Now it was time for her to shower and get ready for the first shift.


Once Tina was ready, and it was time for her to take over, she got out of her depressing, small cabin and climbed the stairs. The boat had already been traveling for a couple of hours, and she was pleasantly surprised to see that they were engulfed by the ocean. All around the yacht, there was only the flat, blue water. It was the 18-year-old’s first time on a boat, and she found it surreal to look at. The wind blew in her face, the salty smell, and the sun beat down on her. There was nothing in sight, but them. The horizon and everything she could see was swallowed by the blue water and the, slightly different shade of, blue sky. It was magical. She walked on the dock where the clients were and were startled by what she saw. The younger woman, that had talked to her earlier, Rajini was sitting on a lounge chair, naked. She was sunbathing, without her bra on, and her beautiful tits were out, for everyone to see. They were big, but firm and well oiled up. It caught Tinaby’s surprise, but she averted her gaze. No one else seemed to mind and her job was to not disturb the guests, and most certainly not to stare at them.

The other girl, that had the same job as Tina told her what to expect.

“They are just hanging out, drinking the odd cocktail. I made a big batch, it’s in the fridge, in case anyone needs a refill. Aside from that, just stay out of sight, but where they can hear you.” – she pointed to a bench. – “I spend here most of the time, but you can walk around. Just read something, or do something on your phone, but don’t leave for too long. And lastly, dinner is a couple of hours, you should help the cook with the table.”

It didn’t sound too complicated, exactly what Tina expected. The pay for being on the boat was pretty good, considering how little work she had to do. For the vast majority of her time, Tina got to sit around and marvel at the sea. It was shocking that she was all of a sudden on the way, far away from any land. Just this morning she woke up at home, like usual, and now the 18-year-old was on a months-long journey, with people she didn’t know, on a fancy yacht. It was surreal, but she loved it. Something was exciting about coming out of your comfort zone and experiencing life. Those moments of fulfillment were interrupted by the mundane task at hand, she still had a job to do.

“Hey, Uhm, Tina. The bat crew, girl.” – a client’s voice called for her. She immediately got up and walked over to the naked woman, Rajini, who was the only one that knew her name. – “Hey, can you put some sunscreen on my back?”

The young girl didn’t even answer. She just picked up the lotion and waited for the woman to turn around. Tina found it a bit awkward, trying not to stare at the woman’s tits, but she had to obey the clients and if she wanted sunscreen, Tina was going to do it.

“So, is this your first time on a boat?” – Rajini asked. “Yeah, it is. What about you?”

“It’s been a couple of times. My sister and her husband rent these out pretty often, so I tag along.”

“Oh, ok cool. I wasn’t sure how you all knew each other.” – The young girl said as she carefully massaged the woman’s back.

“Yeah, just my sister, her husband, and some mutual friends. I’m the single one in the bunch, but also the youngest, so I’ve got that going for me. You said you were 18, right?”

“Yes, I am.”

“That’s a fun age. You shouldn’t be working, you should be partying. Very soon you will be working all of the time and miss these days. Go have fun, you can drink a cocktail, on me. We are in international waters, so it’s fine.”

“Uhm, yeah, sure.”

Tina wasn’t sure what to do. There was no way she was allowed to drink during work, but at the same time, she had to listen to the guests. In the end, the young girl figured a cold drink wouldn’t hurt. She poured herself a glass and sat back on her bench, out of sight from the clients. She liked Rajini. All of the other guests completely ignored the crew, but she was different.

Even that little chit-chat left a good impression on Tina, who still wasn’t used to her job. She had been a waitress before, but this was different. It was like she was a butler, or a servant, on a boat. It’s a weird position to be in, that took some getting used to. But the young girl was out for some quick cash and new experiences. Before she knew it, it was time for dinner and the shift was over.

“So, how was it?” – the girl that had the same job as Tina, asked her.

“Not too bad. They didn’t need much. But it is a little weird how we are all on the same boat and no one is paying attention to us. It’s like we are invisible to them.” – the 18-year-old said.

“Yeah, I guess it is awkward at first, but you will get used to it. These people are just on vacation and they go on yachts all of the time, so I can’t blame them. After a while, the crew just becomes a part of the scenery.”

“Yeah, I suppose so. It is just a shame really, but it is a job after all.”

“Well, if it makes you feel any better, we are going to be in the Bahamas tomorrow. They want to spend the day there, so we are going to have some time on the land, probably go out.”

“Wow, that’s cool. And we can just get off the boat and party?” – Tina asked. “Yeah, pretty much. The captain will make a schedule and everything, but from what I heard, we can spend the evening there.”


Just as promised, the next day the boat arrived in the Bahamas. It was Tina’s first time in the Caribbean and arriving in some foreign marina was an unforgettable experience. Everything was different there. The architecture was different, the people were different and wore different clothes and even the water was different. When they set off, it was a very dark blue, while the Bahamas had a gorgeous light blue hue. It was exciting for the 18-year-old that hadn’t done much traveling in her time to be there. She wanted to jump off the boat and swim to the shore, to get to see some locals, do local stuff, and eat some of the food. But the crew had to wait. She was still working and was informed that they would only have time off in the evening.

“I just spoke to the clients.” – the captain announced during lunch. – “They are going to stay on the boat for a couple of hours, while the sun is strong. Then they will go out and they will be out for the whole evening. They’ve rented hotel rooms, so we don’t need to be on the boat during the night. You can all go out, and come back whenever. But don’t party too hard, we’ll have work to do tomorrow.”

“Ah cool, is everyone coming out tonight?” – one of the guys on the crew asked.

“Well, I’m not and I know the chef isn’t. We are too old for that, but for the rest, I can only recommend it. I’ve been here many times before and the party is great.” – the captain said.

It sounded like a plan and a great one at that. This was exactly the kind of thing Tina signed up for. She was essentially being paid for a vacation in the Bahamas. Sure, there was work and it was tedious. Having to sit around and bring cocktails or snacks sucked, and when the boat wasn’t moving it was very hot. The guests were inside the yacht, which looked like a fancy apartment and was air-conditioned. Tina didn’t have that pleasure. But it was all worth it. In a few hours they would leave and then the crew would also set off. 7 of them, the younger ones, we’re all going out together. They would have dinner, walk around and then go out for drinks. It was exciting, especially for Tina who never really got to go into bars and clubs in the states. Luckily in the Bahamas 18-year-olds could drink to their heart’s desire.

“So, let’s start with a beer? I mean, you don’t want to get too hungover, we have work tomorrow.” – one of Tina’s co-workers advised her.

“Sure, I wouldn’t mind a cold one.” – she said. – “So, do you have some cool stories, from working on boats? Any celebrities, or something like that?” – She asked, as they were waiting at the bar.

“Uhm, I’ve been in the business for a couple of years, so yeah. Nothing too crazy and I never actually got to work for someone famous. I have some friends that were on some Hollywood actors’ boats, but I just get rich guys. Super rich, but not famous. A lot of finance people.” – they got the beers and walked back to the rest of the crew. – “I’ve seen a lot of drugs on these boats, usually cocaine. There have been a couple of fights, which is problematic in a confined space. People having sex, that kind of stuff. Never had to throw a dead body overboard or anything.”

“It seems like a fun job, I love the travel so far. I can’t believe I’m in the Bahamas, and I’m getting paid for it. I mean, my friends are working as servers in restaurants, get paid less and just stay there the whole day, this is way better.” – Tina said.

“True.” – another co-worker started. – “I was in Costa Rica last year, and that was great. The clients spent a few days on-shore, so we had a vacation over there and got paid for it. We went into the city, we went kayaking and looking at some caves, it was awesome. But it gets boring too, especially on super long journeys, you can have days without seeing land.

And you do miss your loved ones.”

“Yeah, tell me about it. I was in Europe for 6 months before this, it just drove me crazy after a while. By the way, Tina, how is your love life?” – the other girl on the crew asked. – “You don’t have to answer if it is too personal, but since we are all on the same boat, we might as well get to know each other.”

“Well, yeah sure, I don’t mind sharing. The truth is, I’m single. I’m 18, going to college, and this job. I don’t feel like there is a time for a relationship in my life, right now.”

“Sounds good to me. Now, should we have a couple more drinks?”

The crew of the yacht could hold their liquor, or at least, they could drink a lot. Tina didn’t have much experience with drinking, so for her, things were much different. They were a great bunch of people, fun to be around with, but more experienced. The young girl was scared of getting too drunk to work tomorrow and decided to cut the alcohol off after two beers. It just didn’t seem responsible to drink more. Once sober, the night quickly started to get boring. The novelty of being in the Bahamas quickly wore off and Tina found herself in a seedy bar, surrounded by slurring, loud and obnoxious people. Not before long, the youngest member of the yacht crew left for the boat, alone.


It was fun being on an exotic island, but Tina was feeling exhausted. The day was long and hot and the process of getting a little tipsy and then sober made her want to sleep. Luckily, the bar the crew was drinking at was fairly close to the marina. After just 15 minutes, the young girl was on the yacht.

She got on but was surprised to see that it wasn’t empty, as she expected. Instead, Rajini was sitting on a lounge chair, listening to music and smoking a cigarette.

“Oh, hey there, Tina. How are you doing?” – the woman asked.

“Hi, I was just out with the crew. We thought that you were all going to be in hotels tonight, so we were on the shore. If we knew you would be on the boat, we would have sent someone.”

“Oh, don’t worry about that. I’m low maintenance. If you want, you can come and keep me some company.” – the young girl accepted the offer.

“So, Uhm, how come you aren’t in the hotel?”

“Well, I just figured I want some peace. The company I’m keeping is really into partying. There’s nothing wrong with that, but I didn’t feel like drinking. Besides, the yacht is much better than that hotel, I don’t see the point in getting one when we can sleep here.”

“I guess if you can afford it.” – Tina said. “What about you, why are you alone?”

“The rest of the crew were having some drinks, but I wasn’t into it. I am not a big drinker and also, we have work to do tomorrow. I just wanted to have a peaceful and quiet night.”

“Oh, look at you, how serious about your job. You should have more fun, live a little.”

“I do, I do. That’s why I’m here, to get out of my comfort zone.” – the 18-year-old said.

“Let me ask you something. Are you single?” “Yeah.”

The older woman did not wait to hear anything else. Rajini grabbed the

younger girl by the hand and lead her inside the yacht. They went into a fancy bedroom, spacious and luxurious, nothing like Tina’s claustrophobic cabin.

“I know you want me, I saw you looking at me yesterday when I was naked.” – the older woman said.

Tina wasn’t sure what she felt, but at the moment, she just decided to go with whatever the other woman said. She began undressing the petite boat worker, and before she knew it, her perky teenage tits were out into the open. Rajini then pushed the girl onto the bed and got naked herself. Tina had never been with a woman before, but she felt ready, it felt right. She was amazed at the older woman’s physique. Her tits were massive and well-shaped, her skin looked spotless and soft and her body was well taken care of. The boat girl had noticed her before, but everything looked so much hotter in the soft light in the room. Rajini grabbed the yacht worker by the legs and powerfully, pulled her over towards the edge of the bed. The girl did not know how to react, so she allowed her new boss to do as she pleased with her. Once she had her, where she wanted, Rajini grabbed her knees and pushed Tina’s legs, towards her head. Now the young girl found herself in an awkward position, her legs were basically touching her head and her pussy was right there, for the taking. Tina was a little surprised, but she was also turned on.

The assertiveness that Rajini carried herself with was something she was not used to. The more mature woman didn’t hesitate, she just dove down and began eating the young girl’s pussy.

This was a new experience for Tina, who had never had her pussy licked by another woman before. It was especially surprising that it was her boss doing it, on a boat, during work. She liked it though, and Rajini knew what she was doing. Despite being more than a little surprised by the whole thing, Tina could feel her private parts tingling with pleasure. The blood was rushing, and her pussy was drenched in juices and saliva. She felt so exposed to this position and the older woman could do anything to her. If this was the job she had signed for, it did not seem that bad. Sure, the hours were long, but she had never been handled like that in her life and loved it. The older beauty flicked her tongue with great skill, around the boat girl’s private parts. Tina knew that what was happening was kinky and forbidden, getting fucked by an older woman, on the boat she lived and worked on, but she could not resist it. They would have to live together for another week, but no one was thinking straight at that moment. The older woman’s tongue roamed territories that the young girl had never explored. There wasn’t even a hint of doubt in her movement. The way the older woman’s powerful hands were pushing down on her legs, pressing them almost to her head. Tina could not help herself and started getting into it. Soon she was breathing heavily.

Letting out the odd moan.

Of course, the captain was still on board, so she could shout, but it was hard for the 18-year-old to contain herself. The pleasures of lesbian sex were simply too much. Her older boss started with a few broad strokes, all along the boat worker’s slit. This got Tina nice and wet, not that it was necessary. After that, the older woman began focusing on the clit. Rajini moved her tongue skillfully in circular motions around it and played with it. She wanted to get the boat girl amped up and ready for what was about to come. Once she could feel her boat worker was properly aroused, by the subtle movements of the hips and the moans the girl was letting out, the older woman got up. She reached inside her cupboard and took out the massive vibrator, much bigger than anything Tina had seen before.

“I hope you like it rough because I am going to fuck you hard. Little boat girl.”

The powerful tool was huge, phallic, and scary in size. Rajini turned it on, to its maximum power and placed it on Tina’s clit. The older woman was set on making this girl cum harder than she ever had in her life. The wet pussy progressively started getting wetter and wetter. It was clear that Tina had never experienced proper clitoral stimulation like that before, and how could she, with her tiny toy. Most vibrators are simply not strong enough, but this one was top of the line. The older woman was going to give the boat girl something to write home about. After a few minutes of pleasuring her with the powerful tool, the girl was about to cum. Her legs began shaking relentlessly and the MILF was too busy handling the powerful vibrator, to pin them down. She also did not care, it was time to punish her boat worker.

With one swift and forceful move, Rajini inserted the huge vibrator in her petite boat worker’s pussy. The girl could not help herself and let out a loud, ear-piercing moan. Tina had never even dreamed about having something like that penetrate her and now it was inside of her wet pussy, still vibrating powerfully. Her older boss began ferociously fucking her with the vibrator until the boat worker could simply not control herself. Her legs and arms were flailing, and she was screaming in a mix of agony and joy. This was an extreme experience for her, something she never imagined she would be into. After a few more thrusts the older woman finally released the petite boat worker. She was free to gather her strength until they began once again a few minutes later.


As fun as that was, it had to end at some point. Tina said her goodbyes and left for her room. Going back in the tiny, cramped, and depressing cabin was hard, now that she had spent some time in the Rajini’s bedroom. But the young girl didn’t have a choice, and she didn’t care. She didn’t think about how small it was, or about how hot it was. She didn’t care that she would only be sleeping for a few more hours. The 18-year-old was exalted. She had just experienced her first lesbian experience and she was over the moon. It was the best thing she had felt, and she knew, there was going to be a lot more dirty, kinky, and bad lesbian sex to come. She was excited about college.

In the next story, I will share with you another story named Drive My Pussy”

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