Trans Summer

"Oh, fuck yes, Lucy, so good," Maddy moaned, her orgasm rising, as she held Lucy almost desperately, as close as she could.

"Come for me, baby, I want to see... and to feel... you come," Lucy said, having always loved seeing the complete vulnerability of a woman when she came. It was the hottest thing ever! She also loved the feeling of a woman coming on her cock, which usually triggered her own orgasm.

"Oh yes, really give it to me." Maddy moaned, her orgasm imminent as she closed her eyes and allowed the inevitable rapture to take hold of her.

Lucy watched Maddy's facial expressions as she slammed into her hard, wanting to get her off, and to take in her unique orgasmic face and listen to her unique orgasmic sounds (every woman has her own unique orgasmic faces and sounds).

Maddy's orgasms always rode in on waves, and she repeated, "Oh God, oh God, oh mother fucking God!"

Lucy was slightly amused as she listened to this minister's daughter using the Lord's name in vain during her rapture. Maddy, as expected, looked so sexy and vulnerable as she came.

As usual, feeling her cock surrounded by pussy cum and feeling Maddy's convulsions on her cock, Lucy felt her own orgasm rising quickly. "I'm going to come real soon," Lucy panted, trying to hold on and last as long as she possibly could.

"Come inside me baby, I want to feel you explode in my pussy," Maddy moaned, keeping her legs tightly wrapped around her sexy teacher.

"You sure?" Lucy asked.

"Yes, yes, I'm on the pill, and I want to feel you shoot inside me," Maddy said, looking up into Lucy's face and indeed wanting to feel her cum explode inside her, something she'd only allowed a couple times in her life, but desperately needing to feel it now.

"Okaaaaaaay," Lucy grunted, unable to hold it inside herself anymore, and she exploded inside her pretty ex-student.

"Yesssssss," Maddy moaned, feeling the warm cum fill her up... having now taken loads in two of her three holes tonight... and planning to fulfill a trifecta at least once during this trip... she'd decided that tonight was only the beginning.

"So good," Lucy moaned, as she continued depositing her load in Maddy... just coming and coming!

"Mmmmmm," Maddy agreed as Lucy slowed down... completely spent from the two ball-draining workouts.

"You're amazing," Lucy said, looking down at a red-faced Maddy, who was wearing a huge smile on her face.

"Back at ya," Maddy said, leaning up and kissing Lucy.

"Shit, there's lesbians out here," a man's voice said ungrammatically.

"Just keep fucking moving, buster," Lucy ordered.

"Whatever," the guy said, clearly drunk.

As he staggered away, Lucy pulled out, stood up, helped Maddy to her feet and drew her in for yet another kiss.

They kissed for a couple of minutes, Maddy feeling a little bit of cum leaking out of her.

"So now what?" Lucy asked.

"Would you like to join us for breakfast in our suite tomorrow?" Maddy asked.

"It's already tomorrow," Lucy pointed out.

"Okay, would you like to come to my suite later this morning and have breakfast with my Mom and me?" Maddy reworded, as she took Lucy's hand and they started wandering towards the water.

"How would your Mom feel about that?"

"She'll hate it of course," Maddy said offhandedly, as they reached the frothy water gliding up onto the sand.

"I don't think I need to put up with her drama on my holiday."

"You may wish to reconsider. Want to fuck her?" Maddy asked.

"Pardon?" Lucy asked, hearing the question, but surprised.

"I'm serious," Maddy said. "My Mom is a complete bitch as you very well know, but it's all just a smoke screen for who she is in the bedroom."

"Really?"

"Yeah," Maddy said, telling Lucy something she'd never told anyone... but although this had only been one great night... she'd known and learned to trust this woman for over a year as her teacher... and tonight she felt a certain kismet, a certain connection that transcended logic, yet made her heart beat and her pussy leak. "For instance, she's a completely submissive ass slut."

"No way," Lucy gasped, even though from some of her experiences and a lot of her reading of erotica (she particularly loved lesbian and transgendered erotica and porn) had taught her that often the more powerful the woman, or the bitchier the woman, the more submissive and kinky she was behind that façade of propriety.

"Oh yeah, I have tons of audio where she's begging to be ass fucked, and her language is always so nasty," Maddy revealed, pulling out her phone to see it had collected over a dozen missed calls, all from her mother, plus lots of texts... mostly from her mother. She'd shut the phone completely down as they left the restaurant.

"Figures," Lucy said, shaking her head... she detested people, especially women, who acted one way in public, yet didn't actualize it at home.

"Yeah, apparently 'Mommy Dearest' has been calling and texting me all night."

"You should probably call or text her back and let her know you're alive," Lucy suggested.

"Yeah, I probably should," Maddy said, as she pressed the contact 'Bitch' on her phone, and switched it to speakerphone for Lucy's benefit.

They walked on the beach, hand in hand, the waves hitting their ankles as Maddy said casually, "Hi, Mom. You called."

"I called? I've been calling and calling endlessly! Where are you? Where have you been?" Annabeth Lee demanded, both relieved and angry at once.

"After dinner we went out dancing, and now we're taking a stroll on the beach," Maddy said, giving Lucy's hand a squeeze.

"Well, get your ass back to our suite right now," Annabeth demanded.

"We're making our way there right now," Maddy said, her casual tone at complete odds with her mother's aggressive one.

"We? Are you still with... with her?" Mrs. Chase asked, using a clear note of disgust when she said the word 'her'.

Maddy said, "Yes, I'm still with Lucy. She's an amazing woman."

"Don't even start with me, young lady," The mother warned.

"Mother," Maddy said. "I'm nineteen now. I'll hang out with whomever I want to. And I won't play along with your phoney Christian agenda."

"We'll talk about this in the morning," Annabeth said tersely.

"I'll be home soon," Maddy said.

"I'm going to sleep, so be quiet when you come in," Annabeth said, inwardly relieved her daughter was okay, and deciding to deal with her disrespect in the morning.

"I will," Maddy said, hanging up. "I guess Mommy's mad at me."

"I could tell. And imagine how much madder she'd be if she knew what I just did to her sweet, precious and very obedient daughter," Lucy smiled.

"Yeah! And you haven't even plugged my asshole yet."

"You like it in the ass?" Lucy asked, her spent cock resurrecting.

"I fucking love it," Maddy admitted. "And your cock would fucking feel so good ramming me from behind!"

"I think that can be arranged," Lucy said. Maddy seemed to be just as kinky as she was.

"May I ask you a blunt question?" Maddy asked.

"Sure," Lucy nodded. "I think we've established enough trust between us to allow blunt."

"Oh, shoot! But first, I meant to play this for you," Maddy said, pulling her phone back out and pressing Play.

"Yes, hammer my shit hole, sodomize me, fuck my asshole," Mrs. Chase begged, her voice clearly recognizable.

"Wow," Lucy said, her hard cock flinching as it waggled around tenting her skirt without her panties.

"Yeah, and as far as I can tell, she only takes it in the ass."

"Really?"

"Yeah, I've listened in on them a couple dozen times, and it's always the same," Maddy said.

"You sinful slut, you're always tempting me with your whore hole," Mr. Chase sneered.

"Shit." Lucy said. "That doesn't sound very Christian!"

"No, the religious zealots are always the dirtiest fuckers," Maddy said, her tone again sounding resentful.

"So I'm learning," Lucy said, amused by all of this.

"So do you want to sodomize my mother?"

"There have been occasions when I've imagined shutting her up with my dick."

"But not destroying her ass with your big cock?"

"Well, I can't claim that thought hasn't also crossed my mind a time or two," Lucy smiled, having imagined drilling Annabeth Lee's ass while she stepped on her head to hold her down.

"It wouldn't take much to get her bent over and begging for it," Maddy said, the idea of watching her bitch Mom get sodomized quite a turn on. Especially if her sodomizer was one of those queer people she constantly railed on against. Lucy being transgendered was even more deliciously out there than if she were only gay!

"I can't imagine that happening," Lucy said. "But I can also imagine it really being a blast!"

"Mmmmmmm," Maddy said, surprisingly horny again... well, not all that surprising, truth be told.

"So what were you going to ask me before you began tempting me with your mother's ass?" Lucy asked.

"Right," Maddy laughed. "I get distracted easily."

"So what's your question?"

"Well, I have a few of them."

"Ask away," Lucy said, curious what the questions were.

"These will be rather personal," Maddy asked, now a little unsure whether to ask them or not.

"You've sucked my cock under the table inside a crowded restaurant, we've made love on the beach and didn't even pause when some drunk wandered by, and you've offered to arrange for me to ass fuck your Mom," Lucy listed off their wild transgressions so far. "I think we've swung the getting personal door wide open by now."

"Okay, I guess you're right," Maddy said. "So as a transgendered person, do you like both guys and girls?"

"I consider myself a pan switch," Lucy answered.

"Sorry," Maddy said. "I should probably know what a pan switch is, but I don't."

Lucy smiled as they stopped walking and sat down on a bench together, still on the deserted beach. "It's okay," she said. "It takes a while to catch up with all the new lingo, especially when it keeps evolving all the time. Pan sexuality isn't much different from bisexuality. The difference being I like being with a man or a woman, which of course is bisexual, but I'll also have sex with a transgendered person. Hence the word 'pan', as in a 'panorama', which is open and expansive."

"Oh, okay," Maddy nodded. She then leaned in and kissed Lucy, "So I guess tonight I've become pansexual as well."

Lucy kissed the younger girl back, and then agreed, "Considering the company you're keeping, I guess you have."

"Do you suck cock?" Maddy asked.

"Yes, I certainly do suck cock," Lucy nodded. "I love sucking cock, and I love eating pussy. They're two of the great perks of being pansexual."

"I see," Maddy said, thinking how hot it would be to watch Lucy sucking a cock.

"But there's more. If I may be completely honest with you, I'm a switch. So I can be submissive to some people, and dominant with others. And when I suck cock, I love getting overpowered and being face fucked," Lucy revealed, leaning in to kiss Maddy. She then whispered in her ear, "I especially love to be face fucked by a hot girl wearing a big, fat strap-on."

"Mmmmmmm," Maddy moaned, those nasty words making her pussy leak again. "I have a couple of big strap-ons back home."

"Too bad they're not here on this island," Lucy said, kissing Maddy's neck. "I'd let you fuck any of my holes you liked."

"So you take it in the ass too?" Maddy asked, although that was pretty obvious, since she'd just said as much.

"Yeah, I love it in my ass," Lucy admitted, although she hadn't taken a cock of any sort except for a new toy she'd bought recently (a bad dragon) for months. "I'm kind of a power bottom. I can have a lovely time taking some really big dicks."

"I see," Maddy smiled, already imagining ass fucking this hot transgendered person.

Lucy, sharing all her sexual links with her ex-student, trusting her implicitly, even though the girl's mother was her sworn enemy, "I really love a dick up my ass while I'm on my back, so I can look up at the person pounding my ass and talk to them."

"I've never been ass fucked on my back, nor have I ever ass fucked anyone on their back," Maddy said, thinking it was a pretty hot idea.

"So, you like ass fucking people too?" Lucy said.

"Yeah, I guess I'm a switch too," Maddy said. "I can take a cock in my mouth, pussy or ass, or give it to a person all those ways too. Although I suppose in most situations I'm a bit more of a dominant than a submissive."

"Then you can dominate me anytime you want," Lucy smiled, kissing her again.

"Do you fuck guys in the ass?" Maddy asked, completely captivated by this not so sweet and innocent teacher.

"Yeah, I'm constantly astonished at how many straight married men have a secret desire to suck cock and to get fucked."

"That's so hot," Maddy said, imagining Lucy pounding any of her Dad's Bible-thumping parishioners in the ass. Or even her Dad. That would be so hot!

"Yeah, I really love hearing a macho guy moaning like a bitch in heat," Lucy said. "I've fucked a couple of football players, and they squeal like little sluts when I'm pounding them from behind."

"You nasty bitch," Maddy said affectionately, thinking of some of the wild adventures they could have together.

"One of my favourite things is to cum in a guy's ass so he can learn firsthand what it feels like to be a girl." Lucy continued, telling Maddy things she'd never told anyone. It was very liberating.

"You can come in my ass," Maddy smiled.

"I'm looking forward to that," Lucy said, having fucked cis women (women who retain the sexual identity they were assigned at birth) and trans people... of both persuasions... in the ass as well.

"So," Maddy asked, kissing Lucy as she did, "Do you... have... a favourite?"

"What do you mean?"

"Boy, girl, transgendered?" Maddy asked, assuming a guy who transitioned into a girl would prefer boys.

Lucy, as if she were able to read Maddy's mind, replied, "Although many boys who transition do it because they want to have sex with boys, I did it because I wanted to be a fulltime girl, no matter what I was doing. Truth is, I prefer girls to boys. So in case it matters, you belong to my favourite category."

"I see," Maddy smiled, happy with that answer.

"Yeah," Lucy continued. "I can get harder and stay harder when I'm with a cis woman or another trans girl than I can with a boy."

"Cis woman?"

Lucy explained, "Someone who was born a girl, and is now psychologically a woman and thinks of herself as such no matter if she's gay or straight. The same logic applies to cis men."

"So I'm a cis woman?"

"You're a sexy as fuck cis woman," Lucy replied, kissing her again. Yes, she loved getting blown by Maddy, and loved fucking her, and loved sharing all her secrets with her, but she was also loving just kissing her. She felt a connection to her, and it was growing stronger the longer they spent together... which she knew was irrational, since Maddy was an ex-student, and also the daughter of the school board chair who already hated her, and the girl was almost a decade younger than she was... so that could be as three strikes against a possible relationship... yet she felt drawn to her nonetheless.

"And you're just a sexy as fuck whatever you are," Maddy said, as she straddled her. "And I need you inside me again right fucking now."

Lucy pulled up her dress and watched as the pretty teenager faced away from her and lowered her pussy onto her very hard cock.

"I should mention my favourite thing to do is licking pussy or ass," Lucy moaned as Maddy began to ride her.

"Mmmmmmmm," Maddy moaned, both because she had a cock back in her pussy and because of Lucy's words.

"Yes, I can eat a pussy or an ass for hours," Lucy moaned, as Maddy wasn't really riding her cock, but was more like grinding.

"Oh fuck, I love your big cock," Maddy moaned, the up curve of the cock head driving her wild in this position.

"You can ride it any time you want," Lucy moaned.

"Be careful," Maddy moaned. "I may take you up on that offer."

"I'll be your submissive cunt licker, your dominant face fucking, pussy pounding and ass drilling dominant, your intimate lover, or even your partner in crime if and when we play the field," Lucy said, offering far more commitment to Maddy than she usually did.

"Like double teaming a guy, seducing a girl, or ass fucking my Mom?" Maddy asked, each of those things she'd love to do with this amazing enigma of a woman.

"Anything you want, baby," Lucy said, as she reached around and cupped the teen's tits.

"Next time we fuck, we need to do it in a bed where we can get naked," Maddy said.

"Yes, and where I can eat your pussy and your asshole," Lucy said, dying to eat this cute girl's butt.

"You're such a nasty hottie," Maddy moaned, everything Lucy said turning her on.

"I'd ass fuck your Mom, and then make her eat my sweaty asshole like a submissive lesbian pet would eat a pussy," Lucy said wickedly.

"Oh fuck, more," Maddy moaned, beginning to grind harder.

"We could double team that hot waitress from earlier," Lucy suggested.

"Oh, she was hot," Maddy agreed, imagining the cute waitress eating her pussy while Lucy pounded her from behind.

Lucy saw a couple in the distance coming towards them. "We're about to have company."

"Let them come, and even stay and watch if they want to. I'm not stopping until we both come," Maddy said, since she was in a foreign country and unlikely to know anyone here... an ironic thought, since against all odds, she had her favourite ex-teacher's cock in her pussy at this very moment.

"That won't take long for me," Lucy said, Maddy's pussy tightening skills around her cock having her balls boiling.

"Come inside me, and I'll come immediately," Maddy said, getting a load in her pussy often being one way to trigger an orgasm for her, as she looked over and saw the two silhouettes still in the distance but getting closer.

"You want my big load?" Lucy asked.

"Yes, yes, fill my pussy with your cum, Lucy, I want you to fill my holes this whole week," Maddy said, envisioning a bunch of wild sex with Lucy.

"Oh, fuck yes, here it comes," Lucy grunted, as Maddy's tight pussy milked her third load of the evening from her.

"Fuuuuuuuck, yes," Maddy moaned loudly, as the warm load erupting inside her triggered her own orgasm, and she collapsed onto Lucy.

They both sat there for a couple of minutes, savouring the afterglow of their orgasms. Two girls hand in hand, likely nineteen like Maddy, walked past them and gave them amused but friendly looks, likely thinking they were just another lesbian couple like themselves, with no idea Lucy had a cock, and it was still buried inside Maddy's pussy.

Once they were alone again, Maddy climbed off Lucy and said, "I really should get back to my room."

"Yeah, I'm exhausted."

"Well, rejuvenate," Maddy said, pulling Lucy up from the bench and kissing her... cum oozing out of her pussy. "This was just an appetizer."

"I'm not sure I can keep up with you," Lucy said, "although I'm definitely willing to give it a go."

"Stop by my room for brunch, eleven o'clock," Maddy said.

"You're sure?"

"Definitely," Maddy said.

"Okay," Lucy said. She was happy Maddy had some blackmail-worthy evidence against Mrs. Chase to fight back against the inevitable threat to her job that was bound to occur once they all got home. Or better yet, maybe they could obliterate that possibility tomorrow!

"In part because we have my Mom to fuck and humiliate," Maddy said.

"You really want to do that?" Lucy asked, that seeming an entirely new level of kink, but also excellent for stabilizing her career.

"It's time she's put in her place," Maddy said, as they walked into the hotel together.