Dylan and Theo Pt. 01

Woo, first story!

Just two pals, one cis, one trans, bonding over a shared vacation :)

Hope you enjoy ~

...

"Dylan, what was the lockbox code?"

"It's 7138," He called back, shutting the trunk of his car.

He lifted his and Theo's suitcases and brought them to the small home. With a hum and a smile, Theo swung the front door open and gestured for Dylan to go in first. The AirBnB was modest and welcoming, with simple furniture and basic accommodations.

The best feature was that it was right next to the beach, and the two friends planned on making use of that the following day. For now though the two of them were alone in a cozy home together, bathed in the warm, dim light that seeped through the thin red curtains.

"Alright. So..." Theo started to walk to the back hallway to inspect the bedrooms, tying his blond hair up to get it out of his face.

"Both bedrooms seem to be the same size, but look here..." Theo motioned for the other to follow him into the first room. He pointed across the way.

"See that door? That goes to the bathroom. What's more is..." Theo stepped to look into the bathroom and pointed to yet another door inside.

"That one goes to your room. Our rooms connect via shitter!" He smiled, amused.

Dylan rolled his eyes as he walked past Theo to check the door leading to his room. He went through to look around what he was going to claim as his room, which he found came with its own surprise. Returning back through the connecting bathroom, Dylan was happy to share his discovery.

"Sucks you didn't choose the other room, dude..." Dylan sucked through his teeth like it was bad news.

"What, why?" Theo seemed interested in Dylans tone. Dylan waved for Theo to follow and showed him that his room had a back door that led to the sandy backyard that stretched to the beach.

Theo groaned and turned away.

"I'm gonna use that door anyways!" He called as he went back to his room.

The two unpacked, and Theo got a better look at the place. It was small, but cozy.

"Dylan! I'm gonna take a shower!" Theo called eventually, heading back to his room.

"Sounds good, dude. I'm gonna order dinner then and chill for a bit." Dylan replied, taking a look out the back door.

With that the two went about their business. Dylan went out to the backyard and looked around. The sun was already setting and it looked gorgeous atop the water. He went back inside and figured Theo would be done with his shower soon.

A devious idea then came over Dylan. He went to the hall and checked to see if Theodore's door was locked. It wasn't. Dylan turned the handle slowly and went inside, feeling safe hearing the shower still running. Theo's clothes were strewn about the bed, and he already had his phone plugged in. Dylan smiled to himself as he made for Theo's closet and carefully slid the mirrored door back.

The closet was to the left of the room and faced the bed. He situated himself inside and slid the door closed just enough that the remaining gap to see through was unnoticeable.

This was the perfect way to scare the shit out of Theo, and as timing would have it, Dylan heard the shower stop. Another few moments went by. The shower curtain was pulled back. A towel was taken off the rack. Silence. Dylan jumped a little when the bathroom door opened and Theo padded in.

It was a quick entrance, did he not get dressed? Dylan stayed put instead of scaring him right away to at least give him a chance to get clothes on. He heard some rustling and eventually a flop onto the bed. He listened hard for whatever sound may come next. He flinched when his phone vibrated, and Dylan quickly changed the setting to silent before checking the text he was sent.

It was from Theodore.

- Food here yet? What'd you order?

Dylan panicked and replied.

- Not here yet, should take about 10 mins. Ordered Chinese. Until then I'm gonna be on my phone.

He worried his reply was sent suspiciously fast, but Dylan heard Theo start typing again.

- Sounds good.

After a quiet sigh of relief, Dylan positioned himself to get ready to leap out of the closet and peeked through the small opening of the sliding closet door. He froze. Theo had his phone in his left hand and his right hand down his sweatpants. Dylan backed up and stood, stuck, unsure of what to do. He decided to take another look and this time, listening hard, he could hear porn softly playing on Theos phone. He could see his hand moving in his pants, obviously playing with himself.

Theo sighed again, his brow furrowing lightly as his breathing became barely audible. Dylan felt his pulse pick up at seeing his friend masturbating. What the fuck was he doing? He felt like a pervert just standing there, peering through the small opening. What else was he to do but sit and watch and hope that Theodore didn't notice his presence?

Dylan gave a small breath at the feeling of his pants becoming tight. Restricting. Frustrated at himself, Dylan put a hand over his crotch and did his best to ignore how hard he was growing. Out on the bed, Theo tossed his phone away from him on the bed and lifted his hips so that he could shimmy his sweatpants down just below his ass, bringing his boxers with them. Dylan watched intently, the hand that was for caging his dick started slowly palming it through his pants.

Theo got comfortable on his back with his left arm tucked behind his head and his shirt pulled up just enough that from Dylans view he could see the cute tuft of pubic hair that covered Theo's pussy.

The two hadn't ever acknowledged the fact that Theo was trans, and Dylan may have done some research at home, but seeing Theo's body was almost unreal to him. Dylan's eyes fixed on Theos clit and how it stuck out even farther when he spread his lips apart, letting the wet heat between them get some air.

Dylan wondered if Theo's cock would ever twitch or throb with wanting like his own would. While he daydreamed, Theos fingers dipped down into his pussy and picked up some of his own wetness. His fingers returned to his clit and made slow, agonizing circles, and from the closet Dylan was almost hypnotized by how Theo bucked into his own touch. The hand that had been tucked behind his head was now gripping the pillow it had rested on.

'So depraved,' Dylan thought to himself. He wondered if Theo ever let anyone finger him. He wondered what sounds Theodore would make with someone else's hands on his body.

Dylan was stroking himself through his pants, but not for long. He quietly undid his jeans and let his cock out. If Theo hadn't noticed him in there by now, he wasn't going to notice now that he was making a mess of himself on the bed.

Theo made a frustrated sound and sat up suddenly, and Dylan stopped stroking himself. Theodore went for his suitcase, and had to move onto his hands and knees as he looked through it on the far side of the bed. The position left Theo's ass posed towards the closet, his pussy on full display. Dylan started stroking himself again.

Theo's ass was rounded and full, and his pussy was pink from how he played with it. Dylan swore he saw how wet it was. Theo sat back again and settled into place, now holding a thick dildo in his hand. Dylan watched as his friend parted his legs and rubbed the toy head between his pussy lips, getting it slick. Dylan stroked a little harder, bracing his other hand on the wall. Theo bit his lip as he rubbed the toy head against his clit, enjoying how it felt grinding against his hard nub.

He dipped it down between his legs, spread himself a little more, and started pushing the thick faux cock into himself. His mouth opened slightly as he felt the toy stretch him and sink deeper. Dylan's breath hitched and he felt himself getting close. Theo started moving the toy in and out, soft breaths accenting every time he thrust into himself. Dylan almost started wondering what Theo might sound like moaning, but coincidentally the blond gave a soft whine a moment later.

The sound made Dylan re-focus on the scene outside the closet. Theo's hips were raised slightly, the toy pushed fully inside of him. He didn't seem used to the size, but, fuck, did he seem to like it. Theo gave himself a rhythm and slowly started bucking his hips, rocking into the toy.

Dylan was fucking his fist at this point, matching the pace Theo was working with. The blond again stuffed the toy as deep as it would go and closed his legs, locking it as deep inside as it would go. His hand, now free, started jerking his clit again in a frenzy. In the dark closet Dylan was on the verge of coming when he heard the unimaginable come out of Theo's mouth. Theo had the corner of the blanket over his mouth,

"Ugh... /Dylan/," He groaned delicately, lifting his hips one last time as his pussy clenched the toy in climax.

Hearing his own name, Dylan finished immediately, gritting his teeth not to make a sound as his body shuddered from the wrecking orgasm. Out on the bed Theo was riding his orgasm, tugging his clit to prolong it. His body eventually relaxed and Theo slid the thick toy out of his hole. His post-orgasm bliss didn't last long as there was a knock at the front door. Theodore sat up and slowly got dressed until he heard the knocking again.

Weird. He figured Dylan would be getting the door. In the closet, Dylan was cleaning himself up with an abandoned jacket he'd found when his phone vibrated in his pocket.

- Hey, food guys here, can you get it?

Fuck. Dylan ignored the text and hoped Theodore would get the door anyways. At the third knock, Theodore cussed and went out to answer the door. As soon as Dylan heard him exchanging words with the delivery guy, he opened the closet door and made for the bathroom.

He saw Theo's dildo laying on the bed. It made him blush remembering how it looked being used by his friend. He went to the bathroom and entered his room through the connecting door and locked it behind him. Safe at last. From his room now, Dylan exited to the living room to find Theodore closing the front door, food in hand. Dylan swallowed and proceeded like everything was normal. They met at the table in the kitchen and made small talk about their vacation plans as they ate, all the while Dylan kept recalling what he witnessed not even half an hour ago.

By the time the two called it a night and went to their respective rooms, Dylan was already wound up again. Lazily stroking himself in bed, he knew he was in deep this vacation.

If only he knew how much deeper he'd be going.