He was nervous, Charles wouldn't deny that and it was quite evident in his posture despite his best effort to look confident. He tried not to be too worried about that fact, he'd been told more than several times that it was part of his charm and allure to women. Being young, smaller and baby-faced tended to attract older women or women with control kinks to pick his photograph from the booklet at the 'agency'.

Charles had been with the company around eight months and was picked often enough but normally again by older women for his baby face and cheaper price due to being considered new. His rates had steadily been rising as his clientele grew and his superiors heard word of how happy they were with his work as a companion. Pleasing women wasn't what had the young man nervous, it was the size of the house he stood in front of.

It would be his first time being purchased by such a wealthy individual, the house he'd been escorted to by a limousine driver had to be at least three stories tall and spanned a huge amount of land, walls lined the edge of the property with well cared for bushes and plans spanning the grassy grounds. Swallowing down his nerves Charles looked down at his attire and pulled at the edges to straighten the wrinkles from his trousers and well-fitted vest that covered his white undershirt.

Wracking his knuckles against the furnished wood of the front door it opened almost immediately, he was greeted not by a servant but a young lady with short auburn hair. The woman leaned on the doorframe, a smirk unbefitting of any woman lining her lips as her eyes took in Charles' features and she sipped at a dark colored liquid in an expensive looking glass.

She was nowhere near unattractive but something about the woman made Charles feel not quite sure of himself. He had seen and met women who refused to abide by standards of the norm before and the woman he stared at fit most of those boxes well. Short and slightly unkept hair, drinking in front of company, lazy posture, and wearing a pair of men's clothing with the sleeves messily rolled up to her elbows.

Many of such things were ones Charles had witnessed growing up with his sister who had gone through a phase of tomboyish nature and matured into a woman who liked fashion and instead showed the world she was just as good as men through her work and no-shit taken attitude. The same feeling didn't strike Charles with the woman he saw, he noted the quite strong and muscled look to her arms and her hips seemed less curvy than even a thinner woman's.

Again, she was very attractive in Charles' eyes and perhaps it was having grown up with a strong sister like Raven but Charles' very much appreciated a girl who knew what she wanted and how she wanted. That made him perfect for his employment, women could boss him around all they wished and he would obey.

Clearing his throat Charles tried to straighten his posture, "Excuse me miss, my name is Charles. I'm from the companion agency and I've been summoned to this addr-"

"Yes I know why you're here." the woman gently swirled the liquid in her glass in a circle. "Please come in, can I get you something to drink?" she offered.

"No thank you, I don't drink." closing the door behind himself Charles shrugged off his light jacket and left his shoes at the door in their proper places. "Would you be free to show me to who's purchased me for the evening miss?"

The unnamed woman stiffened and pressed her lips tightly together in a line before answering. "I did, I'll be your master for the evening." Blinking his eyes quickly Charles couldn't help the smile pulling his lips up in a charming and unconscious manner, "Lovely, I'm so pleased to meet you then!" It would be his first evening in the company of a woman under the age of thirty since being hired on.

"Well then Mistress-"

"Master." the woman cut him off but seemed to urge him on to continue what he'd been saying.

"Er...right. Master, what sort of evening did you have in mind? I'd also very much like to know your name." he wouldn't expect a name, some clients preferred the anonymity aspect of the relationship and preferred to be called a pet name or simply Mistress, in this case Charles expected he'd be calling her Master for the evening.

"It's my first time purchasing an evening from the company so I'll admit I'm not exactly sure how to begin, I suppose...I'd like to get right down to it." setting her glass on a random side table the woman lead Charles over to the stairs and began to ascend them with him following close behind. "I have the bedroom set up already. Call me Erik."

"Of course Erika-"

"No." came a gritted voice, "Erik. Not Erika."

Confused Charles tried not to let it show on his face, he didn't like comparing it to such but sex was much like a game where every customer had their own set of unspoken rules. It was his job to figure out what those rules were and so far he was beginning to understand that Erik wanted him to use male pronouns towards him, why he had no idea but it was by far not the weirdest thing he had done for a client.

"Yes Mis-...Master. If that is what you wish."

His quick acceptance of the terms seemed to please the woman, no, man and his broad shoulders visibly relaxed as they entered the bedroom.

When the bedroom door closed all of Charles' training and experience kicked in subconsciously, he ran a hand up Erik's arm and pressed a kiss behind his neck near his hairline, "You're very beautiful, I'm quite fortunate to get to spend an evening with you, Erik." The other man shivered under his touch, either Erik was very touch starved or had been anticipating this evening all day and couldn't wait to get down to the biscuits.

"Go lay on the bed." he was ordered as Erik pulled out of his touch and began undoing his trousers, they dropped to the ground with a hefty thunk because of the metal belt looped through them.

Eyeing the bed Charles spotted leather ties on the corners of the bedposts, his wrists and ankles were going to be sore after he finished there tonight. He knew it already. Erik didn't seem the gentle type but something about him also nagged at the back of Charles' mind, he acted confident but something about everything told Charles that perhaps his companion didn't have as much experience in all of this as he wanted Charles to think.

"Would you like me to undress first?"

"Yes." came another flat order. Right down to business then, expertly the young man stripped of his clothes and tossed them into a pile in the corner before laying on the bed. Lifting his wrists to be tied down, in his wait Charles let his eyes take in every bit of his companion.

He licked his lips in anticipation as Erik paused in his undressing to tie Charles down and then continued, pulling his shirt and the rest off in its own pile. "Master, please use me as you see fit."

"Oh I will." Erik's voice started to become a bit lower and confident as the last of his clothes hit the ground leaving him just as bare as Charles.

The sight left Charles' mouth feeling dry and his eyes staring probably too much. His evening companion had a flat chest with two twin and fading scars lining horizontally on his chest in place where both of his breasts had been surgically removed.

The first thought that came to his mind being that Erik had suffered a sickness of some kind that forced him to have them removed and flattened, then scolded himself mentally for thinking something very obviously not true. Everything added up, the surgery, the clothes, name, and pronouns. It wasn't something normal by society standards but then again neither were middle-aged ladies who liked to have their way with a man less than half their age. Mentally scolding himself a second time Charles figured that this wasn't a sexual thing for Erik, it was simply who he was all of the time.

It made sense then why Erik would have purchased from the company, mostly anonymous and not the type of company to judge fetishes or lifestyles. Suddenly Charles felt like he had a million questions to ask Erik, how long had he been like this, when had he figured it out or decided to change to a man? The last thing he wanted was to sound rude or disrespectful.

Raddled out of his thoughts when Erik straddled his hips and leaned over him, their lips met roughly and without grace or finesse. Still, Charles found himself kissing back with a vigor he hadn't felt in a long time. It had always excited him to learn new things and Erik fascinated him already, he was beautiful and wanted the other man to know that. The kiss was inexperienced and messy, teeth clanking and tongues getting nipped but satisfying in its own way.

He lifted his head from the pillow to try to follow the forceful and demanding kiss Erik broke, only to find himself restrained and his head fell back into the lumpy pillow. It left Charles' cock twitching and his tongue licking twice over his lips in want.

"I want you in all of the worst ways. Ever since I saw your photograph in that book I knew I wanted to tie you to my bed and make you writhe and want me."

"You're doing a very good job so far Erik." his eyes picked up the little twitch of a smile that pulled on Erik's lips every time he used the name properly, all Charles wished was to please his Master for the night and if that meant using specific names he would scream the name out in every room of the mansion.

His Master reached over the side of the bed where Charles knew a small basket of items had been laying but he hadn't taken a look as to what specifically had been inside. A bottle of vaseline sat on the bed next along with a rubber dildo.

Thrill filled every fiber of Charles' body, after figuring out Erik being a man he'd wanted to know how the night would go. After all despite being a man he had womanly sex organs, he'd gladly fuck Erik in the ass if that was what the man wanted.

Licking his lips again with expectancy Charles shivered, "Going to give me a little show?" his eyes flickered from the dildo to his Master's groin, soft and visibly wet that was trimmed but not free of matching auburn colored hair.

A laugh exuded his Master's lips as she started coating her fingers with the vaseline. Adjusting her sitting position Erik knelt between Charles' spread and tied legs, "Oh Charles...you're the show."

Her hand disappeared from his limited sight as Charles quirked his eyebrow, "What does that mean Mast-nn hey!" The young man couldn't help the slightly squeaked outcry when a cold and slicked up finger had pushed its way inside of his ass.

"Erik I'm not sure how I feel about-oh!" pushing his head back further into the pillow as his body strained the finger moved slowly in and out, teasing his hole with movement.

"I know this must be confusing for you but you are here to please me tonight. Nothing would please me more than fucking you in the ass. I knew from the moment I saw your picture in that book you'd look so good with cock stuffed inside of you." Erik declared and pressed a second finger inside of Charles to work him open, listening as Charles gasped and was left wide-eyed unsure what to think.

"I-I don't, I don't know-" Charles stammered his words as the man in control of him thrust his fingers harder into his ass. He had never done this although he had done anal with women before, the feeling burned as the fingers stretched him getting rougher with their jerks and thrusts as more vaseline was added to the mix. It was a strange feeling that Charles couldn't decide if he liked or not, his cock on the other hand had started to stiffen despite the discomfort.

"I've never-" his unsure words halted Erik's movements, his steely eyes looked beyond unhappy and almost a bit betrayed. "I see..." the fingers disappeared and a stiff aura filled the room. For some reason the last thing Charles wanted to do was disappoint Erik, even if it meant giving his ass over to the other man. So as the other pulled away he choked out, "No wait! I um-! I've never done it this way before but I'd like to try with you!"

Having said the right thing Erik stopped again, "I've never done this to someone else before." the embarrassment thick in his voice and fluster obvious on his face.

"That's okay." Charles gave one of his award-winning smiles, "Unstrap me, I can help."

Moments later Charles had moved into a position he had never imagined himself to be in, on his hands and knees with three oily fingers fucking him in the ass. HIs cock responding to every thrust gratefully and greedily. "I've never had..."

"Never had fingers in your ass before? Feels good, doesn't it? You look good like this." Erik complimented, the lust becoming thick in his voice. "You're so hard just from this."

"S-Surprised me too, feels better than I expected it too."

As the fingers kept moving Erik leaned himself over Charles' back and experimentally planted hot kisses over his shoulder blades. Charles didn't want to sound like an asshole but somehow he had a feeling that Erik had never been accepted before, he lived alone and purchased from an escort agency, inexperienced. There weren't many people who would openly accept someone like the other man, in fact Charles had a feeling most others in his company would have walked out after getting a few fingers in their ass. It was a humiliating act that was leaving Charles in a mixture of wishing it would stop and craving it desperately.

Fingers stopped and the body heat behind Charles disappeared, he whipped his head around to find Erik pulling on a device he hadn't seen before. A large dildo with straps that went around Erik's legs to act as a make-shift cock. "That's going in me?" his voice became unsure and wavering but lifted his ass. "I trust you."

No answer came back leaving Charles with a stiff body, pressing his forehead down into the pillow. He could feel the large piece of plastic, slicked up, press against his stretched hole and became even more rigid with the wait. A hand held his hips and the other Charles guessed held onto the base of the toy to help guide it in. "I'm putting it in now." Erik's voice was that same flat that he seemed to default to when he was unsure of himself or nervous. "I'm ready."

Pain surged in Charles' nerves as the toy passed through the first tight ring of muscles in his ass and sunk in slowly, a burning feeling slowly engulfing his whole body. He tried to force himself to relax but found it too difficult and grunted out with pained noises. "K-Keep going!" he urged on when he felt Erik stop. "Keep going, just stop once it's all in."

Feeling like his body had been split apart it took a good few minutes of Erik soothingly rubbing hands down Charles' back and legs for the pain to ebb away enough for them to continue. Grunting with each thrust, ones that became more and more intense as they continued on, tears pin pricked at Charles' eyes. Pain-play was another first for the escort, typically women didn't enjoy causing him pain and though that wasn't Erik's intention Charles found himself getting drunk on the new feeling.

"Feels good, doesn't it?" his Master asked, uncertainty leaving his voice, "Your cock is so hard, if this was a real cock I bet you'd have cum by now."

"F-Fuck!" Charles cried out loudly, tears bubbling down his cheeks as he reached underneath himself to hold onto his shaky thighs. "I only want your cock, no one elses!" He didn't care if the cock wasn't real, this was a pleasure he only wanted to feel with Erik. To share with this man who was unbelievably unique and beautiful in so many ways.

His orgasm hit him out of nowhere, the feeling had been building up so intensely in Charles' groin that the feeling overwhelmed him. His ass clenched and thighs held together as he arched his back and coated the bedsheets with white stripes of thick cum. Left raggedly shaking and breathing unstable, not daring to move even as the toy was delicately removed from his hole.

"Has anyone told you how gorgeous you are when you cum like that?" he could hear the smile in Erik's voice.

"Can't say that...that I have. I've never cum like that before." Charles tried to say back smugly but it sounded more on the side of pathetically happy in his post-orgasm. When his legs allowed Charles finally sat up, "Now Master, let's do something for you." Touching Erik's cheeks he pulled the other man in for a soft and promiseful kiss. "Tell me what you like."

They ended up in the opposite position, Erik on his hands and knees with Charles gently fucking him in the ass. Softer and more caring than what Erik had done and the other man seemed to respond to that better than rough movements. Two fingers playfully moving inside of Erik's pussy as his thumb rubbed over his clit for extra measure. Erik's orgasm had been wet and long over-due, leaving now only Erik but Charles with an overwhelming sense of satisfaction when his fingers had been coated in an abundance of wet orgasmic juices.

Sated and tired they washed up and dressed, "Will you buy me for an evening again sometime?"

"You'd want that?" Erik quirked an eyebrow in his direction. "I mean, you did enjoy yourself but I didn't think you'd readily jump back in bed with me."

"Why wouldn't I? I felt good, you felt good...hey." he said gently when the other turned away, touching Erik's arm. "I wasn't kidding when I said you're beautiful, er...handsome? Whatever! You're amazingly attractive okay!?"

Lifting his eyes to meet Charles the other man asked, "So this-" he gestured to his body, "doesn't bother you at all? You don't think it's weird?"

"Not to make you sound like a science experiment but I think it's fascinating. You're so differently beautiful I know that if I didn't say something now I'd regret it forever."

A warm look entered Erik's eyes, the evening hadn't been perfect. The sex had its ups and downs, they had done things wrong but Charles wanted to try again, to perfect it. Together. The way he looked at Erik was like nothing the man had ever experienced before, being wanted just the way he felt instead of the way people saw him. "You're not half bad yourself Charles, don't sell yourself short. Next time I think I want the whole package. Wine and dine, then we roll into bed together for a few hours and pillow talk afterward."

"It's a date."