S.L - The Teen Escort Pt. 05

Author's note: This is a chapter in a series that will include lesbianism and themes of sex work, with potentially various guest kinks in different chapters depending on the client. This chapter features a transgender girl. This is a smutty fantasy so please do not read if you want realism. All characters in this story are 18 or over.

This is part of the 'Sapphire Lane' universe which is a collection of various stories all set on Sapphire Lane, or at the nearby Ginerva Academy and Violet Liberal Arts College, each lesbian related but exploring different kinks. Each story is standalone but features cameos with characters from other stories, and potentially crossovers.

Chapter 5

Gabbie didn't really have any chance to talk to Kayla at school on Friday, and though her friends, especially Tina, were intrigued with her new escorting job, she felt like it would be a bad habit to tell them all about every single client she had... besides talking about the submissive sex she had had with Amalie would only make her horny, and thoughts of the night before were distracting her from the lessons enough already.

At the end of the day, Gabbie was getting some books out of her locker when Kayla approached her. "Hey Gabbie, you still coming to my slumber party tomorrow?"

"Of course, I'm looking forward to it!" Gabbie smiled at the desi girl. She knew Kayla's friends were going to be there too, but hoped there would be some chance to tell the girl about her experiences with Amalie, and hear if the girl had her second client yet too.

"Great! I was going to go shopping at the mall before for some new outfits to wear on the job, so wondered if you want to come along?"

Gabbie had been meaning to spend some of her earnings on new clothes to wear when escorting, as though she liked her orange dress, she didn't want to have to wear it every time. "Sure, I'm keen to get some things myself."

"See you tomorrow then." Kayla touched her on the arm, then turned, walking away down the corridor. Gabbie smiled after the girl, happy to have a friend to share the adventures of escorting with, and excited for their shopping trip together.

"Aww, does Gabbie have a crush on her escorting buddy?" Gabbie turned to see Tina, who had spoken, and Natasha.

"Oh don't start that... You know I'm not interested in tying myself down with anyone... it was the whole reason I became an escort after all!" The teen said, blushing a little.

"Yeah, yeah. But just think, she might just be perfect for you! You could have some kind of open relationship where you both agree to be faithful unless it's with an older woman paying you to have sex!" Tina teased, and Gabbie rolled her eyes.

****

Gabbie was already excited when she got up on Saturday with her afternoon mall trip with Kayla, then the slumber party, which she was slightly nervous about as it was with a group of girls she didn't really know well, but was sure it'd be fun. However the day got off to an even better start when she saw Bianka had texted her another job offer. It was for Sunday afternoon with a woman named Michelle, who was 61 years old, and wanted to have 'sensual' strap-on sex.

'I know you have never done any kind of penetration with dildos before but thought this might be a good introduction if you wanted to give it a go.' Bianka had added, and Gabbie, keen to try as many different things as possible while escorting, eagerly accepted the client. As well as experiencing what a dildo felt like for the first time, she was also intrigued at the prospect of a woman who was more than a decade older than anyone she had been with so far.

She hadn't been expecting to have a third client in her first week on the job, and was thrilled to end her weekend with one. The teen was now even more excited to go shopping with Kayala as she could pick an outfit to wear for Michelle.

****

Kayla also lived on Sapphire Lane, so Gabbie called on the girl late morning, and the two got a bus that went by the mall. The teen reflected how strange it was, as the week before Kayla had just been another girl she was in senior year with at Ginerva Academy, but they had been flung together when they both applied to work at Bianka's Escorting Agency. She realised she still barely knew the girl, but somehow already viewed her as a friend, and assumed Kayla felt the same, appreciating how she had gone out of her way to invite her to a slumber party, and a shopping trip beforehand.

They got boba tea when they arrived at the mall, then wandered leisurely around the clothes stores. Though Gabbie's mom had always given her quite a generous allowance for clothing, she found it exciting to have her own extra income to spend, and the girls went into pricier stores they normally wouldn't of considered buying from.

They chatted as they shopped, and got to know one another as well as sharing a bit of banter, with Kayla, who preferred drum and bass, teasing Gabbie for liking country music. In one store Kayla picked out a slinky red dress she liked, but Gabbie was struggling to find something so the desi girl suggested a white dress with a crossed halter front.

"Don't you think that's a little slutty?" Gabbie asked, unsure.

"Well yeah, sure it's a little slutty but this isn't to wear to church! Come on, give it a try." Kayla urged the hesitant girl, who laughed and agreed to try it on. They went to the changing rooms, and Gabbie was going into her own booth when Kayla just pulled her into the same one as her.

The two girls changed into their chosen outfits, with Gabbie trying to avoid peeping at Kayla's body as they undressed, though finding it hard as she was either looking at the girl or at her reflection in the mirror.

"What do you think?" Kayla said, posing in the dress, and Gabbie looked the girl up and down. The red dress was short, so showed off plenty of the girl's mocha brown thighs, and it clung sexily to the curves of her butt and hips. The top pushed her large breasts together, with a plunging neckline displaying her eye-drawing cleavage.

"Very hot!" Gabbie said as the girl gave turned to show it off from every angle. "It certainly shows off your body! I do think a strapless one to show off your beautiful shoulders would perhaps be even hotter... but can't have everything on display at once or you'd just be naked!"

"Thanks, I like it but you're right, a strapless one might be hot too... maybe I'll get this one and then we can find me a strapless one especially for you to admire my shoulders..." Kayla laughed, and Gabbie blushed a little but nodded.

"But look at you! Like a slutty angel in white..."

Gabbie blushed, never being called a 'slutty angel' before but liking getting the compliment from Kayla. She looked at herself in the mirror. The white dress was as short as Kayla's red one, and it's halter front, with the straps crossing over her breasts then round her neck, displayed just as much of her cleavage, just in a slightly different way to the noirette's plunging neckline. The teen wouldn't normally consider buying a dress like that, as it was too slutty for anything formal or with family, nor was it something that could be worn casually, and as a eighteen year old highschooler she wasn't old enough to be going nightclubbing, but it was perfect to wear on an escorting job!

"Oh, I forgot to say, I have another client tomorrow so I'm going to wear the dress I buy today for them... apparently she wants to fuck me with a strap-on!" Gabbie said.

"Luck you! I haven't gotten another one until Tuesday... I'm sure your client will love it!"

"Perfect, then I'll get it. Thanks for bending my arm to make me try it as I'm just not use to picking out clothes like this..." Gabbie said, looking at her reflection again and liking how sexy the dress made her feel.

"If we ever get a joint client we should totally wear these dresses. Red and white, you know, like a angel and devil kinda thing!" Kayla said and Gabbie laughed, agreeing, and hoping she will get to share a client with her new friend one day...

"Noodles for lunch?" Kayla asked as they changed out of their dresses and back into their casual clothes.

"Sure!"

****

After they had gotten back from the mall, Gabbie had gone home to drop off her new clothes and pick up her overnight bag, before walking to Kayla's house at No. 6 Sapphire Lane for the slumber party. One of Kayla's friends, Jessica, had already arrived so the three of them sat chatting in Kayla's lounge, waiting for the other girls. It wasn't long until the doorbell rung, and Riley entered. She was a beautiful blonde and captain of the school's cheerleading team, but was in no way haughty or arrogant, and Gabbie found it easy to chat to her.

"Do you know why Ariana isn't coming tonight?" Kayla asked the blonde who shrugged. "No idea, she just told me she was busy... not like her to miss a party."

The next to arrive was Abigail, who excitedly asked "So are we home alone?"

"Yeah, my mom has gone to the city with a 'friend' for the night." Kayla said.

"Great, because look what I pinched!" Abigail pulled out a bottle of vodka from her bag, showing it to the girls.

"Where did you pinch it from?" Jessica asked.

"Okay, I didn't actually pinch it. My stepmom gave it to me..."

"What did that emphasis on friend mean?" Riley asked Kayla, intrigued at the desi girl's earlier comment.

"Oh, just that it's probably just the latest intern she's seduced from work..."

The final of Kayla's friends to arrive was Roselina, a transgender girl. Gabbie thought she was perhaps one of the prettiest girls in the senior year, like a damsel out of a romance painting, with her porcelain skin, rosy cheeks, grey eyes, long brunette hair, and faintly freckled little nose. She was petite and slim, though soft fleshed rather than bony with a plump butt, and firm round tits from breast augmentation which she had gotten for her eighteenth birthday.

"Now we're all here, I think it's time we changed into our pyjamas!" Abigail said.

"You really want to... I mean we are eighteen now." Kayla laughed.

"Yeah but it isn't a slumber party if we aren't in our PJs! Abigail insisted, and the other girls relented, going upstairs to change into their nightwear.

****

Gabbie found the group of girls easy to get on with and fun, and though she was quieter than she would be if it was her own friend group, she felt included and joined in on the gossiping, occasional bitching, party games, shots of Abigail's vodka, and karaoke. They ordered pizza and Gabbie thought she had probably drank her weekly sugar intake in Kool-Aid, which was a drink she hadn't had for years but Abigail had brought, seemingly another thing, alongside pyjama wearing, the girl felt was essential for slumber parties.

Gabbie's pyjamas were a pink pair of shorts, and white tee, which was a similar sort of thing to what most of the other girls were wearing, besides Riley who had a sleek chemise nightdress. However Kayla had opted for purple lace panties and bra, beneath a silk dressing gain she had open at the front. Throughout the evening Gabbie kept finding herself glancing at the girl's body, with her mocha coloured cleavage, tummy, and thick thighs exposed, wishing she could caress her fellow escort.

Maybe Tina's teasing comment earlier had just gotten to her, or perhaps she really did have a crush on her new friend.

****

Gabbie was the last of the girls to use the bathroom, and she went to the loo then brushed her teeth and wiped off her subtle make-up, before going to Kayla's bedroom where her and Roselina were going to be sleeping with their host. The other three girls were in the guest room.

The desi girl was at her dressing table, brushing her thick wavy black hair before bed, while Roselina lounged on the foldout bed she had on the floor beside the double bed that Gabbie would be sharing with Kayla.

Gabbie climbed into the bed, wishing briefly that Roselina was sleeping in the other room as otherwise it would have been a perfect opportunity to catch up with Kayla about their latest clients in more detail than they could at the mall... but perhaps it was for the best as it might have been a little weird to bring it up as a topic while they were in bed together.

"I'll turn off the light." Kayla said after she had finished brushing her hair, and she plunged the room into darkness.

"Mind you don't step on me!" Roselina laughed, as the girl found her way across the dark room to the bed.

"Yeah you're a tripping hazard down there, but at least you should cushion my fall!"

Gabbie felt Kayla climb into the bed beside her, the girl pulling up the sheets to get beneath them.

"How about a bedtime story!" Roselina asked.

"What do you have in mind?" Kayla asked.

"I don't know, I'm sure you two have some fun stories..."

"What from escorting? Why not... I think Gabbie wanted to hear about my latest client too! Then perhaps we could hear about her's..."

"Yeah sure." Gabbie said, thinking it was funny that Roselina, who she had thought would prevent her from hearing the story of Kayla's latest client, was actually the person to enable it. She was a little shy to go over the intimate details with Roselina, but she had told a group of seven girls about Tracey, her first client, so supposed it shouldn't be too hard, in the dark and following on after Kayla's story, to open up in the presence of the brunette.

"It was with a white brunette woman in her late forties, called Alexis, who was kinda petite but had quite the bust! Her lips clearly had filler but it made her look a little slutty which I liked... " Kayla began telling the story. Alexis wanted to do a yoga workout with Kayla first, who had been told to come in a sports bra and yoga leggings.

"I started to wonder if she got confused what an escort was, and if she thought she had actually hired herself a training buddy, but she began to increasingly touch me as we gradually got more sweaty, and then she was on top of me on the yoga map, kissing me on the mouth and neck."

Gabbie pictured the curvy girl, with her sports bra showing off her mocha coloured cleavage glistening with droplets of perspiration, while yoga leggings clung to her thick ass. She imagined the woman on top of the girl, pinning her to the yoga mat as they passionately made out. It was certainly a hot way to begin things, and Gabbie hoped that one day Alexis might book her for a session... As Kayla continued to describe their foreplay on the yoga mat, Gabbie imagined herself in the desi girl's place, but soon found herself fantasizing what it would be like to be the mature woman on top of the teen. 'It's a shame I wasn't more involved with Kayla during the orgy at the audition as then maybe I wouldn't need to imagine what her lips felt like... think the closest we were together was when I was licking Mitena's pussy, and she helped me make the girl cum by rubbing her clit.'

As Kayla continued her story, Gabbie found herself slipping her hand down the front of her pyjama shorts. 'Should I really be touching myself in Kayla's bed...?' The teen wondered guiltily but she couldn't help herself, too aroused by the story that the girl beside her in bed was telling.

"Soon she had my sports bra off, and was kissing my breasts, licking her tongue around my nipples..."

Gabbie could remember the girl's nipples from the audition, where Bianka had kissed them too. She pictured the girl's dark brown teats, with their big areolas dotted with Montgomery glands, and imagined what it'd be like to lick them, as she continued caressing her wet pussy.

Alexis' sports bra was the next thing to be removed in the story, and Kayla had returned the breast worship, licking and sucking on the nipples of the mature woman. Then their yoga pants came off, and there was tribbing and pussy licking. Gabbie pictured Kayla's dark brown pussy with fleshy labia and dark bush of pubic hair, and wondered what it would taste like, wishing she had gotten to lick it during the orgy at the audition. She imagined the exertion of the yoga exercise would of made it more pungent with salty sweat, and shivered a little in arousal, trying not to breath more heavily as she stroked her clit.

Kayla's story ended with her sharing a shower with Alexis, which was expectedly steamy with the woman caressing the teen's body as she scrubbed it, and the two sharing deep kisses as the warm shower water sprayed across their bodies.

"Your turn Gabbie, tell us about your second client." Kayla said after the story of her encounter was over. "Gabbie?"

"Sorry, yeah sure." The teen blushed, as with her eyes closed, absorbed in her fantasies about Kayla, she hadn't realised it was now her turn to speak. "She was called Amalie, and was a blonde in her early forties, a little shorter than me with a lithe body, and quite a stern face, and far more dominant than Tracey, my first client. She even made me call her 'ma'am' which was pretty hot, and didn't waste any time as she was sat on the dining room table, with my face between her legs within minutes of me arriving! She told me exactly how she wanted me to lick her..."

"I hope I get a client like that one day, who just completely takes charge of me like I was just their toy!" Kayla said, and Gabbie was a little surprised, not having imagined the girl to have any submissive tendencies, but turned on at the thought of her being dominated by Amalie. Gabbie continued her story, describing how the woman's pussy had tasted, and how she had been verbally dominant in giving orders which she had loved obeying. The teen didn't stop masturbating as she told her story, but though the memories of her second client were making her even more aroused, she tried to constrain her enthusiasm as she didn't want to give away in her voice what she was secretly doing beneath the bed sheets.

Gabbie had told her friends the story of her first client while sat around a table in the ice cream parlour, but found in this telling she was going into far more detail about what they done and how it felt... But this wasn't surprising given she was led in the darkness, with a far more intimate audience, following on from the equally arousing story of her friend, and telling it with her hand down the front of her pyjama shorts. She was telling the girls how Amalie had played with her nipples, and how the woman had kept reminding her that they belonged to her that evening, when Roselina interrupted with a loud moan.

"Are you touching yourself?" Kayla said, turning on her lamp and catching the brunette, who though covered by a blanket, clearly had a hand between her legs.

"No!" The trans girl pulled her hand away, then nodded, blushing at being caught touching herself. "Okay, yes... but can you blame me! I mean I'm led here, first listening to Kayla talk about some hot sweaty yoga sex and then Gabbie telling us how she was dominated! Just couldn't help myself..."

"Nor could I..." Gabbie admitted, feeling a bit bad if she didn't own up to touching herself too now that Roselina had been caught doing the same. Kayla laughed. "Wow, you two are so horny! I've been led here resisting the urge the whole time while Roselina has been jilling off on the floor, and Gabbie is rubbing herself right next to me! I'll join you, just let me know next time!"

Kayla licked her fingers, and pushed her hand into her panties to rub her pussy. "Carry on Gabbie, we want to hear the rest of your story."

Gabbie continued, describing the second time she licked Amalie's pussy and how the woman had then licked her's in return. She resumed rubbing herself, finding it even more hot now she knew that the other two girls were touching themselves too, just as aroused as she was by the stories. Now that the girl wasn't trying to hide it, she could hear Roselina's soft moans from her foldout bed, and Kayla's breathing grew heavier too.