Femboy's Fate: Sage

The story depicts _GENTLE_VANILLA SEX between a desperate-for-money cute feminine femboy with a plump ass and perky tits - and the mysterious man whom he meets on his first escorting assignment. The nervous rentboy is in for a surprise when he finally gets to know who the man really is.

Please, be informed: There is NO brutal treatment, no violence, no humiliation, no forcing, and no dominance elements in the story. It's a romance!

Tags: escort, femboy, small perky tits, round ass, cute outfits, skirt, school uniform, dress, knee socks, makeup, gentle sex, tender sex, anal sex, passionate sex, making love, blowjob, rimming, student, college, secrets, role-play, romantic, first-time-rentboy, first-time-client, crossdressing-at-home.

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Sage Faraday hesitantly pressed the button "Activate" which was located under his new profile on the webpage for escorts.

After weeks of inner fights and mental struggles, he finally made a decision. He would do it. He hadn't had many options. He was already in debt with all his friends and other students from his dorm. It couldn't continue like that. He was more and more miserable, more hungry, and more desperate.

Since his parents tragically died in a car accident, leaving him with virtually nothing to sustain himself (as they had a lot of debts themselves, after a rather spectacular bankruptcy of their company during C-19 lockdowns), he was living a desperate life.

Sage was on scholarship, but with very demanding conditions. His grades had to be consistently very high, which involved a lot of time, and he couldn't take a normal part-time job to earn money for food and daily expenses. For a few months, he lived from some last savings, but after that, he hit the bottom one day - he was hungry and in despair. He had borrowed some money from his friends, but their patience had since run out.

He needed to do something. Anything. For him, it would be enough to earn 600 dollars a month and that would be sufficient. He didn't need much and he wasn't greedy. After analyzing the price range for escort services, he realized they were usually in the range between 200 and 500 dollars for an hour.

But he needed a bit more. So, he set his price at 600. The profiles of other escorts were filled with their beautiful pictures - with obvious filters on: blur on their faces; artificial, vivid colors; and suspiciously perfect makeup. Some even had enlarged eyes and lips, since some filters could do that also.

Sage himself was a femboy, or a crossdresser, but... only at home, in the safety of his room. For the outside world, he was just an inconspicuous-looking boy, with a 5'5'' height and a slender frame.

Through his teenage years, Sage became an avid anime fan, especially Sailor Moon, he loved the way the characters dressed and admired cosplayers in their outfits. He followed accounts on Pinterest that re-pinned photos of girly outfits, and androgynous people with colorful hair, in pretty dresses, skirts, and high socks.

He befriended Adam during his senior year of high school, and on his eighteen birthday, Adam bought him a sexy femboy outfit. Sage found it surprisingly exciting. He started to jerk off wearing it and he made out with Adam, wearing femboy clothes.

It was the moment he started to consider himself bisexual. He was first only attracted to women, but his experiments with Adam widened his sexual preferences.

Seeing all that, Adam suggested Sage could have autogynephilia, the paraphilia popular among crossdressers, because he was aroused by the act of wearing more stereotypically feminine clothing.

But Sage also fantasized about having a more feminine, round body, and he loved wearing pretty outfits in general, so he wasn't sure if he really felt like a woman inside - or only liked the IDEA of looking like a woman?

Adam encouraged him also to take female hormones for a few months, just to test the waters if he would feel better about himself, suggesting it would additionally help with Sage's pimples and his bony teenage body. Sage was able to obtain some pills and after a couple of months he noticed interesting changes in his body, but... ironically, it also ruined his relationship with Adam! Sage lost his appetite for sex, due to the intake of strong testosterone blockers, his libido severely decreased. Disappointed, he stopped taking them and... waited for his libido to come back. After about eight months, it slowly returned to normal, but... at that time he had already gotten accepted into college and Adam didn't follow him. Their relationship was done.

And then the tragedy happened...

After the death of his parents in a shocking car accident, Sage was left alone, dejected and depressed, and then the very practical problems occurred. He had no money to buy food.... All that was left of his parents' assets were taken by creditors. Being penniless, he was forced to daily borrow money to eat, but it couldn't last any longer.

He decided to find a page with escort services.

Sage didn't add many pictures to his profile.

He couldn't bring himself to show his face. So, he took a picture of his tits that grew during his HRT session. They were still tiny, just small cone-shaped mounds on his petite chest with puffy, pink nipples at the top. Sage liked them and sometimes even dreamed about having them a bit bigger. But they could look super pretty if presented with finesse, so Sage put on a lacy bra and pulled aside the cups, so the nipples were partially showing from under the thin pink lace. The picture looked sexy and tasteful.

He also did pictures of his bum. The hormones made his body a bit softer and less bony, his buttocks accumulated some fat and looked quite plump and sexy, feminine. Regarding it as his asset, he added a picture in which he was leaning on the table, in a short schoolgirl skirt and long socks, and with his ass clearly seen under the slightly pulled-up skirt. His slender legs looked good, and his ass was smooth, white, and round.

These two pictures would have to suffice. He described himself as a femboy/gender-fluid person in his BIO and stated that he only would do sex in condoms and only vanilla-type sex. He had no high hopes. The price he set was pretty high.

Sage checked profiles of people with similar price ranges, and they were all really gorgeous and 'model-like'. He was just a nothing-special boy. His face was small, and indistinct, with no prominent feature that would catch people's attention and make them look at him twice. He could be invisible in the crowd. Yes, he dyed his hair light blue, but it didn't add much to him. He just looked like a very plain boy, a 'try-hard' type, that colored his hair to make himself more special, but it just didn't work in his case.

He realized his chances to find a customer - a so-called 'regular' sponsor or a sugar daddy - were very limited.

Sage waited for a couple of days, and still nothing happened. He started to consider adding a picture of his face, not a very obvious shot, maybe a profile? But on Saturday morning, as he woke up, he was shocked, finding a new email in his inbox. It was a notification from the escort service: "You have a new offer!"

His heart pounded hard, and his throat got dry in a matter of seconds. With trembling hands, he opened his inbox on the escort webpage.

"Hello, Fae" - that was Sage's chosen nickname - "I'd like to book your services for tomorrow night. I live near your listed location. Please confirm if you're interested and available for an hour-long meeting. Quinn."

The shock of what had previously been little more than an unsettling vision becoming suddenly very real... Sage practically fainted. He fell on his bed.

He almost had an incident of nervous asphyxia. His breathing became short and shallow, and he had to rest for a while before he opened the inbox again. He clicked on Quinn's profile. It was almost empty since it was a client's profile, not an escort profile. The age was listed as 27 years old. That was good news because Sage had been afraid that some old grandpa would want his services. Sage had sometimes visited his own 92-year-old grandfather before he died, and he had on him a very distinct smell of medicines used for geriatric ailments. This somehow traumatized Sage and made him fearful of the prospect of having sex with a very old man. He always imagined for some reason the person would have crutches and a denture! He knew it was a bit paranoid, but he couldn't help it.

The only other information on Quinn's profile was: "Height: tall. Weight: average. Body type: muscular."

Wow, that sounded good. The region Quinn indicated he was residing in was nearby!

Sage's heart just couldn't stop beating fast, as he sent his reply: "Hello, Quinn. Yes, I will be available for you on Sunday evening, at 7 PM. Please send me your address. Fae."

The response came within a minute. Quinn was fast!

"I'm pleased to hear that..." and he gave his address.

Sage was stunned. The address was very close, just next to campus! It was very convenient, and unsettling at the same time.

It all seemed so unbelievable. Sage's mind was racing like crazy, he threw himself on the bed, and was rolling from side to side, going a bit crazy, imagining numerous scenarios of what could happen.

He knew that the webpage provided some security for its users, as the clients had to pay for premium membership - only then the contact option under the escort profile was active - with their credit cards. They were also paying the site a fee.

Also, after the meeting, they were obliged to send a message notifying the moderators if the transaction went through properly or if there were any problems.

But apart from that, if the man wanted to kill Sage... not much could stop him.

Sage hardly slept that night. He had moments when he wanted to cancel it all, and then he had to force himself to calm down.

On Sunday, he shaved himself very diligently, and prepared perfect makeup after watching some online tutorials by famous female influencers. He chose a light pink color for his lips, a navy-blue eyeliner, and he even decided to go for fake eyelashes, although only moderate in length.

He got himself dolled up, pulling on white-blue high-knee socks, white-blue high-top sneakers, a super short school navy-blue skirt, and Japanese-style girls' school shirt with a tiny navy-blue scarf. He tied his light blue hair - which he had shoulder blade-long - in two pigtails.

After doing all of that he realized he probably needed to prepare himself in one more way... So he pulled out his dildo, as he didn't have a buttplug, and after fingering himself a bit, he put that into his ass.

He was used to it, as he pleasured himself like that basically every day, so it wasn't new for him. He pushed it inside - heavily lubed - and sat on it, so as to stretch his ass a bit more.

Then he painted his nails, sadly they were short, but he chose a nice paint, a deep blue sky mixed with glitter that made his nails look shiny and elegant.

Sage also perfumed himself with his favorite fragrance of jasmine and rose, intended for women, but he loved it so much.

Prepared like that, he decided to wear a long, graphite coat he had and seldomly used, except for at his parents' funeral. The coat didn't have a hood, so he took a dark scarf and put it on his head, and arranged it in the form of a hood. He needed to be careful when leaving the dorm, as he didn't want other students to see him. He was glad it was Sunday evening - the dorm was quiet, and not many people were wandering around.

He rushed off the dorm, looking around, mindful not to stumble into somebody he knew, and left campus five minutes later. He soon was walking through an area with one-family houses, rather elegant ones. He was glancing at the residences with curiosity, as they looked pretty upscale. Obviously, a person able to pay 600 dollars for one hour had to be well-off.

Finally, he found the right location. It was a very elegant mansion with a formidable yard around.

Sage swallowed hard. He noticed that the gate was... open. How very convenient. He carefully went inside and, using the marble stone pathway, headed toward the main door.

As he stood in front of it, he tried to calm his nerves. He took off his scarf and unbuttoned the coat, so the client could see what he wore under. Feeling his hands getting sweaty, he knocked on the door.

It was 6:57 PM.

Almost instantly, he heard the sound of heavy steps coming from somewhere inside the house and the door opened. Nobody asked "who's there?" so he was in the right place after all...

The man who opened the door had light coming from behind him, so Sage couldn't see his face too clearly at first. He only noticed that the man was... really tall, probably around 6'4''.

"Hello, I'm Fae," Sage said shyly, almost afraid to look the man in the eyes.

"Hello, Fae. I'm Quinn. Please - come on in." The voice was low, deep and welcoming.

Sage hesitantly went inside, and stopped in the wide antechamber, not knowing where to go.

The owner of the mansion closed the door and said, "Please, come with me." His voice now sounded matter-of-fact.

He led Sage upstairs. Sage used this time to admire the silhouette of the man. He had wide shoulders, long muscular legs, and narrow hips. He also had short ink-black hair.

They went into a large, rather luxurious bedroom located on the second floor. There was one big bed in the middle and some dressers along the walls. There was also a giant panoramic window behind with a view of the large green yard and a swimming pool, still visible even though the sun was setting already at 7PM.

Only then did Quinn face Sage, in the full light of a large, modern chandelier.

The man turned out to be... wow.

Sage was surprised that a person looking like that even wanted to find an escort and not just... go to the first bar on the corner and return with a date. Quinn was a looker! Classically handsome, with perfect jawline, tanned complexion, slight five o'clock stubble, straight nose, and perfect eyebrows. His eyes were piercing icy blue - although they seemed a bit red, as if the man had conjunctivitis. And he had some muscle on him! The man was a really fine specimen of a man, and Sage stared for a while in astonishment.

"Wow, you really are... attractive. What am I even doing here?" he blurted out, letting his natural honesty take over. And he felt stupid right away for saying that.

The man raised one eyebrow and smiled ruefully. "Well, thank you, Fae. It's complicated, but let's leave it at that," he replied tersely.

Sage bit his lip. It was just too good to be true. The man had to have some flaws, right? He probably was some brutal rapist, killing young femboys and burying them in his impressive yard. Or some sex trafficker! Or a sadist...

"Sorry, I shouldn't ask," Sage cleared his throat, feeling stupid all the time.

"No, that's... not a problem. I'm just in a situation where I don't want to engage in any relationship. And people that I could pick up in bars or clubs tend to demand to exchange phone numbers, and they call me later so... I just don't want to have that for now."

"I understand it perfectly. In some situations, it's probably the best solution," Sage said in an official tone, eyeing Quinn.

Suddenly he realized that the owner of the house had... a very sad gaze. As if something was bothering him. His energy seemed a bit low, and he had dark circles under his eyes.

"Are you of age?" Quinn asked quietly.

"Yes, I'm nineteen and three months to be precise."

A moment of silence.

Quinn sighed and slightly tilted his head.

"So, we have an hour, minus three minutes. I prepared a dress I wish for you to wear. You are welcome to go to the bathroom and change into it," he said, clearing his throat.

Sage blinked dumbfoundedly. "A dress?"

"Yes. From what I saw on your profile you are 5'5'' and weigh 120 pounds. That should be fitting..." He pointed toward the bed.

Only then Sage noticed a pink, flowery dress lying there. Also, a blonde, long-haired wig...

He swallowed, and hesitated for a second, but... that wasn't really the problem, was it? He already came here crossdressed, so why not take this one step higher?

"Do you have some shoes for it? Mine won't look good with that dress."

Quinn's lip corner twitched. "That's a very good observation, Fae..." His voice was almost warm.

"My real name is Sage," Sage admitted, blushing.

"Oh, okay. My real name is just Quinn." He smiled but still with some sadness in his eyes. "So, Sage..." He headed toward the closet and took out a box. "I think these may fit." He lifted out sandals with small heels.

Sage knew they probably would be a bit too small, but said nothing. He was glad he chose a pink bra and panties set for today, as they would be a match for this dress.

"Okay, where's the bathroom?"

Quinn made a gesture to his left, not saying anything.

Sage went there, still feeling pretty nervous. So, the man wanted him to crossdress or maybe role-play somebody? An ex-girlfriend perhaps? Sage hoped they split on good terms and Quinn didn't want to reenact some revenge.

The moment he was in the bathroom alone, he took his clothes off. He checked his small blue backpack and pulled out a box of wipes that proved to be very gentle for the delicate skin around his anus and - nice smelling too. He quickly wiped his ass - just to be sure, and took the dress in his hands. He stared at it for some time. It was just a nice dress for a rather slender, medium-height woman.

He pulled it on over his head and checked himself in the mirror. The dress had a big cleavage and his pink lacy bra was almost visible - almost. Thanks to Sage's naturally slim waist, and a bit of feminine hips, which still had some fat deposit from the time he was under HRT, he looked pretty good, like a young girl.

He tied his hair in a single ponytail over his nape and put on the wig. It was obviously new. It smelled of freshness. It even had a small label under it, saying it was 100% European Natural Hair. The sandals were a bit too small, and his big toes were hanging a little over the edge in the front, but not too much, he still could walk normally, and it didn't look funny. He only wished he painted the toenails pink, not blue.

Sage again checked himself in the mirror. He looked surprisingly good. He was happy he at least decided to use pink lipstick as it all fitted perfectly now.

Now, it was that moment. Sage took a deep breath and went outside, holding a small lube sachet and a condom in his clenched, sweaty hand.

Quinn was sitting on the edge of the bed, with his head lowered, staring blankly at the floor. He didn't look... enthusiastic or happy. He raised his head and fixed his eyes on Sage. It was a strange feeling, the man looked dejected!! Not like a person waiting to have hot sex, for sure! What was going on here?

Quinn didn't comment on Sage's looks, he didn't say anything.

Sage slowly came closer, nervously swallowing.

"What do you wish from me?" he asked quietly.

"I want you to suck me off," Quinn said in a calm, impassive voice, and he slowly stood up.

They were now four feet from each other. Their eyes met. Quinn face didn't change.

Sage let a small breath out and slowly nodded.

But he still stood there, not able to move, or take the initiative.

Quinn was obviously waiting, observing Sage, who still stood like an ice statue.

"Is... there a problem?" Quinn finally asked, tilting his head slightly.

"No, of course not. Sorry, I'm just mentally preparing." His quiet chuckle came out very tense.

Quinn raised his eyebrows. "Did you... even do that before?"