S.L - The Pretty Boy

"What's that?" Caidan recoiled, shocked.

"What do you mean?" Casey said, confused and dismayed at the Caidan's sudden reaction to her naked lower half.

"You have a pussy!"

"Yeah...!" Casey agreed, confused. "Wait... do you only go for trans girls or something?"

"No! I thought you were another femme twink."

"A twink? You thought I was a boy!" Casey couldn't help laughing. "Hang on, did you say 'another', as in you're one too?"

"Yeah, what did you think I was!"

"A girl. I was a little surprised to see a penis but guessed you must just be trans."

"I can't believe a girl has sucked my cock!"

"Hey, don't be a drama queen! I can't believe I sucked a boy's cock and tasted his cum..."

"I thought you said you were gay?"

"Yeah... but that means a different thing coming from a girl!"

There was an awkward silence before Casey asked "But if you found a cock in my panties, would you have continued? I mean you were attracted to me when you thought I was a boy so it's only upon finding out I wasn't that turned you off."

"Yeah, it's a shame as you'd be such a pretty twink." Caidan laughed, a little bashful of his panicked reaction, as after all it had been his mistake, the girl never tricked him into thinking she was a boy, and she had suffered the same disappointment as him. 'I really should have known but guess I was too carried away with him, or I suppose 'her', appearing suddenly and resembling so much like the kind of boy I fantasise about.'

"This is pretty hilarious really, a gay femme twink and pretty tomboyish lesbian accidently getting together! I'm sorry for my sudden reaction, I panicked seeing a pussy... though you took seeing a cock in your stride."

"That's okay, no problem. It'll make a funny story to tell." Casey laughed with the boy before another awkward silence as they both sat on the bed, naked from the waist down with the taste of Caidan's cum in their mouths, unsure how to proceed.

'It's been fun even if 'she' did turn out to be a boy though maybe it doesn't have to end here... no better not... but then again there is no harm in asking...' Casey though, blushing at what she was about to suggest. "Well, I do have a strap-on, so why I don't I put it on, and you just pretend I'm a boy? It'll just be for once, for fun... or would you have wanted me to be the 'bottom', I'm not sure how you like your gay sex!"

"I'd happily have been top, bottom, or both with you, though not sure that it'll work now I know you're a girl. Guess you feel the same now that you know I'm a boy..."

"Maybe, but I can very easily pretend you're a girl! You're pretty enough with soft smooth skin... and I have never fucked a butthole before, but it's up to you, I'm not offended if you don't want to..."

"I'd feel a little guilty as you gave me a blowjob and then I'd be the one getting fucked again without pleasuring you in return..."

"I did enjoy sucking your cock, even if I didn't realise it was a boy's at the time, and I think I'll have fun pegging you if I imagine you're a girl, though perhaps you could..." Casey said, pausing in embarrassment.

"Could what?" Caidan probed her, intrigued what the lesbian girl was suggesting, as he had to admit her ideas were turning him on.

"Perhaps lick my asshole in return as I'm not sure I'm ready for anal penetration. You could pretend it's a bussy! Then I could rub my pussy as you do that and cum that way, so you'll help give me an orgasm but wouldn't have to touch or even think about my pussy."

Caidan thought about it and grinned "You have a deal missy!"

"Great! Though don't call me 'missy' as from your perspective I'm a boy remember!" Casey laughed, and climbed out of bed to fetch her strap-on harness and dildo which she kept in her underwear drawer as well as a bottle of lube.

"I don't think I ever had a cock in me that's got a history of fucking lesbians." Caidan joked, watching the girl pull on the strap-on and tighten the harness in place. The dildo was pink and a little bigger than his cock at six inches.

"And a most illustrious history it is too." Casey laughed, semi-exaggerating, but thinking back to the three girls she had used it on which were a hippie chick who she never saw in classes but often played guitar on the green, a preppy girl who had kept her plaid skirt on as she rode the cock, and most recently Nora. Also, her roommate Mitena had borrowed it for her escorting job, so it had been inside a total of four pussies which, though no great number, was probably more than most sex toys.

Caidan pulled off his denim shirt, revealing his flat chest and small nipples, and got on his knees before Casey, wanting to first suck the girl's dildo. He took the pink plastic cock between his lips and bobbed his head back and forth as he sucked on it, closing his eyes and imagining the cock was actually part of the 'boy' stood before him. Though the boy's sucking on the dildo didn't give Casey any physical pleasure, the visual of him knelt at her feet with his feminine lips wrapped around the plastic cock did arouse her, and she reached down to run her fingers through his wavy black hair.

"You look so pretty with my cock in your mouth!" Casey said, putting her hand on the back of the boy's head to encourage him to take it deeper into his mouth, as he gagged a little on the six-inch shaft.

Caidan finished the blowjob roleplay, leaving the dildo slicked with his salvia, and grinned up at the girl. "I always like to suck something before it goes inside my butt, now let's get this lubed up!"

Casey squeezed a blob of lube into the boy's hand, then some into her own, and together they applied it to the toy, rubbing their hands up and down the shaft to coat it with lube. "Unlike all those pussies this cock has been inside, my asshole doesn't naturally lubricate so we'll need to use plenty of this!" he said as he slathered the shaft of the plastic cock before he, satisfied it was sufficiently prepped, climbed back onto the bed. He laid down on his back but with his knees pulled up so his tight asshole, between his small buttocks, was exposed.

Casey had been imaging doggystyle, but Caidan explained he found it more comfortable this way, and wanted to look at the face of the 'beautiful boy' fucking him. "Fine by me, I'll enjoy seeing the face of my hot girl as I fuck her!"

Casey squirted some more lube onto her fingers and rubbed them over the boy's asshole, tracing the rim of his anus with her fingers before pushing one of her fingertips against the tight wrinkled entrance, and gently eased it inside.

"It's a good job us lesbians have short nails!" Casey laughed as she tenderly fingered the boy's asshole, gently pushing inside a second finger as it stretched further.

"Do you want my cock inside your boy pussy?" Casey said as she finger fucked the boys asshole with her two fingers, whilst she stroked her strap-on dildo with her other hand, enjoying the feel of the lubed plastic which will soon be sliding in and out of the femme boy's tight butthole.

"Yes, I need your cock inside me!" Caidan moaned, and Casey pulled out her two fingers so she could rub the tip of her lubed plastic cock against the tight wrinkled entrance of the boy's asshole, gently easing it inside as his anus stretched around the pink dildo. The brunette girl held on to the boy's ankle to keep his leg up and spread, as she began to thrust her cock inside of him, enjoying the feeling of pegging her first asshole. Caidan's lips were parted as he moaned, his eyes rolling back as he felt the cock sliding back and forth in his rectum. He reached down to stroke his cock, which had become erect again from the anal simulation.

Casey, as well as the arousal from seeing the boy moan as she fucked his asshole, also felt physical pleasure from the base of the dildo, strapped over her crotch, rubbing over her clit with each thrust. She didn't think she could orgasm from the slight rubbing and pressure, but it was enough to sexually stimulate her beyond the exhilarating mental aspect of pegging the femme boy. Casey thrusted more deeply, wanting to feel each push of the cock inside the boy's butthole against her clit.

The prostate stimulation of the dildo fucking his butt, along with his hand stroking his cock, still wet from the girl's blowjob, gave Caidan his second orgasm that night, with his pulsating cock squirting out a second, small, load of cum that landed across his flat tummy as he relaxed on bed, untensing post orgasm. Casey pulled her strap-on out, panting a little as she sat down on the side of the bed as the prolonged thrusting had been quite intensive, feeling like she had had a mini workout.

"Now for your boy pussy!" Caidan grinned, pulling himself up and eager to taste Casey's ass, despite her being a girl.

"Yeah, lick my bussy!" Casey laughed, joining in on the roleplay. She got onto all fours on the bed with the pink dildo hanging down from between her legs, and swayed her ass invitingly at the gay boy. Caidan ran his hands over the girl's buttocks, small and firm with a smattering of freckles like her cheeks, then spread them to reveal her asshole, a tight wrinkled speck surrounded by a ring of dark pink skin.

"The prettiest bussy I've ever seen!" Caidan grinned, thinking what a shame it was that such a cute butthole belonged to a girl, and pushed his face between the brunette's butt cheeks. He kissed the girl's tight asshole, and licked his tongue around the dark pink rim before probing the entrance.

Casey moaned in pleasure at the feel of the boy's tongue on her sensitive butthole, an erogenous zone that she rarely felt pleasured, especially not orally. Supporting herself on one arm, the brunette girl reached down to her crotch with her free hand, pushing it beneath the strap on harness so she could rub her wet pussy and hard clit. Already aroused from everything they had done so far, Casey was glad to be giving her pussy some direct attention, and the girl caressed her clit, firmly but not roughly, sending pangs of pleasure through her body coupled with the sensual feel of the wet tongue probing her asshole.

"Seems like its also the tastiest bussy you ever sampled from how enthusiastic your tongue is!" Casey giggled before loudly moaning in pleasure again as the boy's tongue passionately rimmed her butthole, Caidan feeling that actions spoke louder than words in answer to the girl's comment. 'Eating this pretty asshole definitely makes up for me not getting the taste of boy cum I was expecting before I found out she was a girl...'

Casey cried out as she orgasmed, never having experienced climaxing whilst a tongue rimmed her asshole before but finding she certainly liked it, and slumped onto the bed, rolling onto her back. Caidan crawled on top of her, and they wetly made out, with Casey feeling a kinky thrill from the knowledge that the boy's tongue inside her mouth had recently been in her asshole.

"I've enjoyed being your pretty boy." Casey said, grinning.

"Yes, you're my little freckled prince." Caidan laughed, kissing the girl on the cheek.

"And you're my pixie cut princess." Casey laughed too.

Both sexually satisfied, they cuddled up in Casey's single bed, sweaty from their lovemaking, and softly kissed. 'I might now have a thing for boys who look like girls... especially if they're as feminine as Caidan and want my strap-on in their boy pussy' Casey thought whilst Caidan was thinking 'I've always liked my boys to look pretty and femme, but girls who look like boys who look like pretty girls might be my new niche...'

Author's note: I hope you enjoyed this queer little escapade! This is the closest I'll ever come to writing 'heterosexual' smut.