Finding Our Real Selves

Sam nodded and put his shoes on too. "I'll be back in a sec Fran." He called as they left.

" Ummm... Sir, Fran's actually kind of-"

"Yeah, she doesn't seem that bad. I dunno, people judge me like that all the time too. I don't like her treating you like being gay is some kind of novelty."

"I mean... I guess I'm not... right?"

Britt laughed "Oh... precious. You enjoyed my fingers an awful lot. What if some guy wanted to stick his dick in you. Do you think you wouldn't like that?"

Sam blushed and looked down at the ground. He opened his mouth to speak but had no words.

"Because what I think..." Britt went on, clearly not expecting an response from him other than to be embarassed. "Is that you'd cry and moan and cum your little brains out all over his dick."

"S-sir please..." Sam whispered. And yet, despite his protest, he found her words making him hard again.

Britt surprised him by quickly drawing him into a hug as she laughed in a rather sinister manner. Something about the way she embraced him gave Sam the impression that the hypothetical had gotten her just as 'bothered' as it had him. "Point is, pet, that your owner likes you as you are so you shouldn't worry about it. Just be yourself." Britt pushed him back out of the hug and looked him in the eyes. Sam looked into her eyes for a while. She seemed a little distant, as though that last part had been for her own benefit, too.

"Sir, I like you how you are too. I like you a lot, actually..."

Britt grinned, looking very pleased but also a little evil. "I guess we can work out our issues together, huh?" She ruffled his hair and started walking home. "See you tomorrow, cutie."

"So she seems... fiesty." Fran commented as he came back inside.

"Uhh, sorry. She thought you were picking on me."

"Yeah, it was actually pretty cute. You gonna let mom and dad know you're dating?"

"Umm... I think we're gona figure that out later."

"Well just be safe. And make sure we dont have any little sammies running around here in ten months, yeah?"

"F-Fran! I... we..."

"I dont need the details little bro. Just remember, no exceptions. I've had too many guys try to talk me into it 'just once'."

"Yeah... okay Fran thanks." Sam quickly hurried back up the stairs to his room away from the awkward conversation. He still had to straighten the room out before his parents got home after all. He found himself thinking.

'I dont think I want you sticking it in me anyway' Britt had said. Did that mean ever? At first he felt disappointed, that was something they were 'supposed' to do after all, even Fran had assumed so. But... when she'd fingered him it had been pretty amazing. Would penetrating her be better? Could anything be better? Should they not at least try? Sam considered texting her to talk about it but ultimately decided that today had been the best and texting Sir to complain was a dumb idea.

The rest of the day passed uneventfully, up until Sam did one last comb over his social media before bed. One feed item was tucked away in his list as though it were trying to hide from him. Fran and Britt had added each other to friends. He frowned a little, wondering what that was about. Better not to pry, he decided, it was probably just Fran being friendly and Britt was too polite to decline.

*****

-Hey Britt! Nice 2 meet u. just wanted 2 say sry if u thought i was picking on sammie :(

-it's fine. A lot of kids at school give him a hard time I guess I'm a little overprotective.

-i think its adorbs! Im happy for u guys. If i can help u guys out lemme know. Sammies always too shy to ask for help with stuff

-Maybe theres something. It might be a little too personal for you though.

-Its fine! Ask away. :D

-Sam told me you work in a sex shop?

-ROFL! Did he? Yeah, part time. Pisses my mom off.

-Do you sell harnesses?

-omg i knew it! :o

-I'd pay for it of course.

-we have a few. I'll send you some links, just pick out the one u want. Do u have lube?

-That would be perfect. And no I don't.

-I can get u some samples but ur gonna need a bottle eventually.

-Awesome. Thanks so much Fran!

-;)

*****

Britt idly stroked Sam's hair, she was pretty sure he'd dozed off leaning against her. She was quite fond of his hair, it was straight, smooth and shoulder length. Hers always got really puffy when it got too long but she preferred hers to be short anyway. Whenever she messed his hair up he always pouted and spent several moments meticulously fixing it, although he knew not to complain.

Britt of course enjoyed the pout immensely, which was why she did it so much. They'd been spending a lot of their lunch breaks just sitting on the grass outside together. Usually that also involved some groping and kissing, but Sam was tired today so she let him nap.

Her phone buzzed. She awkwardly reached across herself with her left arm to fish in her pocket, trying not to disturb him. Eventually she succeeded in getting her phone out and checking her texts.

It was Fran, the harness and attachment had come in. Britt had wanted a larger cock for it, but Fran had made sense when she'd said that it would be a better idea to start small.

Britt shook Sam gently, trying to wake him up. He just mumbled and nuzzled further into her tits.

"Oh really then?" She grinned and reached under Sam's shirt. Grasping one of his nipples between thumb and forefinger. Slowly, she started to pull and twist.

"Ah! Ah!" Sam jolted awake and tried to squirm away from her hand. She kept a firm grip though, and all he succeeded at was pulling on his own nipple even more.

"Awake now, pet?" She asked. A shiver of sadistic glee washed through her at his distressed squirming and pained expression. It was a lovely expeession of his submissiveness to her, what she was doing hurt, but he made no effort to fight or break free.

"Yesss Sirrrr" he whined, looking into her eyes desperately. The look he gave her went straight to her crotch. Gods if they weren't at school right now she would shove him to the ground and ride that pretty mouth of his.

"Good. Lunch is almost over" she said, releasing him after one last tug for good measure. "We're going to your place after school."

"But, Fran doesnt have classes on mondays, Sir."

"I know. She wont bother us."

Sam frowned a little and looked at her, trying to puzzle out the deeper meaning behind what she had said. "Umm... Sir..."

"Dont worry your pretty little head about it, kitten," she assured him, ruffling his hair and grinning when he pouted and started fixing it.

*****

Sam opened the door to his house ahead of her and started going inside. Britt took advantage of the situation and grabbed a hand full of his bubble butt and squeezed. He yelped a little as if in protest but she noticed that he quite clearly leaned back towards her a little, giving her better access. When she walked past him into the house he had a coy little smile on his face.

She handed him her backpack. "Go up to your room and wait for a few minutes, I need a word with Fran."

"You.. huh?" Sam actually didn't just look confused he seemed slightly concerned.

Britt leaned in close, cupping Sam's testicles and giving them a gentle squeeze that would be impossible to interpret as anything other than 'first warning'. Of course in this case it was actually his only warning but he may have figured that out too.

"Do as you're told, pet. Nothing's wrong, trust me."

Sam swallowed. "Yes Sir. Sorry Sir." He said, waiting for her to release his testicles before grabbing her bag and scampering upstairs to his room. 'As if calling me Sir twice will get him out of a punishment later,' she mused.

She went down a small flight of stairs and rapped on the door to Fran's miniature basement suite.

Fran opened the door and peeked her head out. "Heyyy," she said, slyly. "Gimmie a sec I've got your stuff right here." She disappeared back into her suite for a few seconds and returned with an unmarked bag.

"Awesome. Thanks so much Fran," Britt replied, pulling her wallet out of her back pocket and handing Fran what she owed her.

"No problem. Receipt's in the bag. Have fun you guys."

"Sam might not. I definitely will."

Fran laughed, "Alright, bordering on TMI there."

"Meh," Britt shrugged. When it came to Sam she felt strangely liberated, like she was almost completely unable to be embarrassed about him or their relationship.

She took her bag upstairs to the bathroom just outside Sams bedroom. She quickly removed her loose pants and, after a brief moment of evaluation, decided to leave her panties on. She unboxed her new toys, sliding the lifelike dildo into the harness and slipping it on, tightening the straps until it was snug and felt like it wouldn't slide around.

Britt looked up into the mirror and grabbed the cock - her cock. Something just felt... right about it. Like there had been white noise - a buzzing in her brain her whole life that she had grown so accustomed to that she didn't even know it was there. But the image in the mirror was calming it down, making her realize how shitty and annoying that buzzing had been, and now nice it was that it was... well, not gone, but quieter.

Realizing she'd been there a while, and Sam might be getting worried, Britt slipped her pants on, stuffing the cock down the side of her pant leg. The almost-realistic way the silicone cock felt sliding against the side of her leg made her smile, and again she appreciated Fran's professional recommendation.

Exiting the bathroom she made her way to Sam's room. He was sitting on the bed, waiting patiently. Britt glanced at the clock and saw her little sidetrack had actually taken almost fifteen minutes. Poor boy was probably getting more worried by the second.

"Sorry I took longer than expected, little one." She set her bag down at the foot of the bed and sat down next to him. "But I appreciate your patience."

"It's fine, Sir..." Sam smiled sheepishly at her, casting only a glance at the unmarked bag that she hadn't had when they'd left school.

Britt put an arm around his slender waist and drew him close for a kiss. Soft and gentle for once, but with her other hand resting lightly on his neck, reminding him who he belonged to. Britt broke the kiss and slid away from him to the other side of the bed, and spread her legs wide.

"Crawl over here, pet, take my pants off," She beckoned with a come hither motion, wondering if her grin was betraying what her intent was. She was certain enough the surprise would be successful, Sam wasn't a dumb person at all, but he wasn't exactly the most... observant person either.

Sam crawled over on all fours and started undoing the button on her jeans. It probably took him longer than he should, but he did notice her cock before it hit him in the face. He had the fly down and had started to tug them off her hips when he suddenly froze.

"Did I tell you to stop, pet?" Britt teased.

"Ummm... No Sir..." Sam resumed removing her pants. As her cock came free of the pant leg, it did actually whip out and hit him lightly in the face. Sam stopped again, and looked up at her, apparently at a bit of a loss for how to proceed.

Britt shimmied the rest of the way out of her pants and gripped her cock at the base, batting the end of it against Sam's lips. Gods he looked so hot with her cock in his face. "Suck it, bitch," she hissed.

Sam showed a lot less hesitation than she expected, taking the tip in his mouth and gently sucking and licking on it. The sight was really hot, but, not exactly what Britt had in mind right then. She slid her hips forward, grabbing Sam by the shoulders and started thrusting gently into his mouth. The slight resistance as her cock slid across his plump lips was causing the base of it to grind against her clit, giving her a nice little sensory thrill, a feeling that was greatly enhanced by how much going through the motions of fucking her pretty little boytoy's mouth was appealing to her sensibilities.

Her trance broke when she felt Sam try to pull away a little and heard him coughing and gagging. She decided to cut him some slack and pulled back, letting him come up for air. "Aww, was I a little rough on you, kitten?"

Sam looked up at her but didn't answer, correctly deducing that there was no right answer to that question. The clever little bitch was getting wise to her traps, she mused, not especially upset at that revelation. It was nice to know that she could train him.

"On your back," she instructed. "I really want to fuck your sweet ass with this. No fingers for you tonight, pet."

"Sir, I dont know if that dildo will-"

"My cock," Britt cut him off before he could try to talk her out of something that she had every intention of doing unless the bed caught on fire. She grabbed her cock by the base and shook it at him "Call this a dildo again and I ~will~ punish you. Do you understand, pet?"

"Y-Yes Sir. I understand." Sam looked a little confused, she'd have to explain it to him later, but now she just wanted to fuck him.

Britt reached back into her unmarked bag and grabbed some of the lube Fran had gotten for her. She opened one of the packets and smeared it all over her dick and then took the excess and worked it into Sam's pucker with a finger. Sam's asshole opened right up, greedily swallowing her lubricated finger and accepting the preparation for the plowing it was about to receive. With how pliant his ass was, Britt was certain she'd be able to quite easily work him up to taking as big of a cock as she wanted.

Sam squirmed against her hand as she prepped him, his hard cockette dribbling a little bit of pre onto his stomach. For all his protests, her slutty femboy's body certainly seemed to want this.

Britt leaned in, grabbing her cock and aligning it with the tight pink hole that was begging for it. She had to fiddle with her position a little bit to get the angle right, she didn't just want to fuck him she wanted to pound his bitch buzzer until he screamed. Once she had the right angle, she pushed, her cock slid into his ass with little resistance.

"Oh! Siiiirrr" Sam groaned at the feeling of the tip her cock rubbing up against his prostate on the way in. The resistance against her cock was much better in his ass, the pressure it created on her clit was absolutely fantastic, and when she hilted inside of him she used the opportunity to grind her cock into him

"Fuck yes... you fucking cunt... rrrrghhhh" Brit swore through clenched teeth as her first orgasm hit. She'd wanted to do this because it just felt right, not expecting to get off on it the way she was. Well, surprises were nice. Sam squirmed under her as she rode through her high, he seemed to be enjoying what she was doing but clearly it wasn't quite enough to get him off.

She corrected her position, grabbed him by the ankles that were dangling in the air and started thrusting, pulling her cock all the way out of him and then re-hilting. The smaller cock actually had the nice advantage that she was able to be as rough as she wanted, which was, of course, very rough.

Sam cried out as she pounded his sweet butthole, his eyes going wide and unfocused as he threw his head back. His hands twitched, Britt could clearly see the instinct to touch himself was kicking in, but he knew he wasn't allowed, so he didn't like the good boy he was.

Britt enjoyed every second of it. The power, the dominance, the way he was already completely in love with her dick, the lovely build-up to what she knew would be another explosive orgasm for herself.

He was thrusting back against her now, his role as a bottom, HER bottom, coming to him so naturally. "Ah! Ah! Ah!! Sir please can I-" He begged, getting his senses together enough to lift his head and make eye contact.

Britt slowed her thrusts down a little and leaned in close, "Not yet, you can cum after I do, slut," she whispered. The look he gave her in response was absolutely adorable. Needy, denied, and resigned. Such a beautiful mask for her little bitch.

Britt shut up any real protests with a quick kiss before she sat back up and continued her relentless fucking, the pistoning of her dick filling the room with the obscene sounds of hips slapping into cushy asscheeks.

Sam bit his lip and shuddered, clearly trying to hold himself back, which was clearly not an easy task with how much he was loving the reaming he was getting. "Sir I don't know if I can stop it" he whined, she felt his legs tensing in her hands, the poor thing really was doing his best.

"Aww, pet, why didn't you just ask me for help earlier?" Britt grinned through her exertions, a wicked idea forming in her mind. She let go of one of his legs and reached down to slap his cock as hard as she could. There was a wet smack as the precum soaked cock wobbled left and right under the impact.

"Ah! Ow!" Sam jolted up, propping himself up on his elbows.

Britt breathed heavy, "Did that slow you down a little, pet?" she asked sweetly, trying to hide how much she'd enjoyed doing that. Sam didn't respond with words, instead giving her the most delicious pout. She exhaled slowly as she started hammering him. That was gonna do it. "Shit... uugghhhh.. cum you little cunt," she growled as her second climax hit Her hands dug into his flesh as she stared down at the cute boy she was fucking. He was panting and moaning with closed eyes, his cock twitching expectantly.

Britt's thrusts became erratic as she rode out her pleasure on top of Sam, and with one particularly good jab into his prostate, his eyes opened wide. He screamed, unable to form coherent words as his little cock started twitching and spewing cum uncontrollably all over him, the first several jets hitting him square in the face. He was an absolute mess by the time his dick stopped shooting, but by the looks of it he was still very high in orgasmic bliss, his body limp as he lay beneath her, spent and basking in the afterglow.

Britt stopped eventually, once the adrenaline of their session had worn off she'd begun to feel a bit of a tenderness in her vagina. The base of her cock had battered her crotch pretty good, she could only imagine what Sam's ass felt like. She grabbed her phone from the pants lying discarded beside her, and opened up the camera. Sam didn't even notice as she snapped a picture of him, lying there, cock in his ass and covered in his own cum, hair splayed out around him in a disheveled mess. A nice memento to keep for later, she mused.

Britt pulled her dick out of him and sat back, panting, exhausted. Fucking someone was hard work, it turned out. Not that she'd have it any other way.

Sam sat up after what must have been five full minutes. "That was... thank you, Sir." He said, blushing. Immediately after, he seemed to realize that he had cum all over himself, looking down at his chest and stomach and touching his face.

Britt burst out laughing, "Clean yourself up, pet. You're a mess."

--

Fall had finally fully arrived, the last stubborn leaves had fled from the trees, leaving behind nothing but bare wooden skeletons. Sam stared wistfully at them as he completed his walk to school, dreading the day of classes. Despite Britt having made his life many times better, Sam still despised school, he learned very little, stressed out over assignments that he didn't see the point of, and while he wasn't picked on by kids as much ever since Britt had punched someone out two weeks ago he still didn't really have any friends. She'd been suspended for several days afterwards, but had assured him it was totally worth it.

When Sam walked through one of the side doors to the school, he immediately set about looking for Britt, since, well, the alternative was to stand around by himself and wait for the bell. He found her soon enough by her locker, talking to her friend Stephanie. Quickly but quietly, he started sneaking up behind Britt, giving Stephanie a shush motion as she glanced curiously at him.