The Reluctant Escort: A Crossdressing Erotica Story

Here’s an excerpt for anyone who’s interested:

Just under a minute later, Minchin found himself back on the bed with the black man, coyly averting his eyes from him and making himself look as small as possible to reinforce his identity as a shy, retiring woman.

The man still didn't say anything. He just stared at Minchin, looking at the smaller man with a slightly love-struck expression.

Again, Minchin spoke first. "Daddy?" he said, ignoring the bitter taste in his mouth from having to refer that way to another man. "Would you like us to do tonight?"

The man's eyes met Minchin's own, smoky set. "This is my first time with a shemale," he admitted, and Minchin felt his last shred of dignity wash away.

"Okay..." Minchin said, quickly recovering. "That's no problem."

The man fell silent again, and Minchin had to bottle his frustration to keep himself from fidgeting.

"Kimberly..." the man began. It took Minchin a split-second to realize that the guy was talking about him.

"Yes?" Minchin asked, his voice low.

"I want to kiss you," the black man went on.

Minchin closed his legs even further as a nervous reflex, and willed his heart to stop beating so furiously. "Then kiss me," he said.

The man reached his giant hands cautiously out toward Minchin. He snaked an arm around the smaller man's waist and brought him closer to him. Then, he moved his mouth closer to Minchin's.

The two men's lips met, and a slow, tentative make-out session began.

There was something in the man's soft and slow style of kissing that told Minchin that there was a certain amount of love and affection in each movement of his lips upon Kimberly's. There was something about that particular realization that made Minchin have to stifle a vomit.

The man's lips met Minchin's again and again, and Minchin met each of his soft kisses with one of his own, stifling his desire to bring up every meal he'd had for the last decade all the while.

After about forty seconds of this, the man changed things up a bit by cupping one of Minchin's cheeks with his hand, and adding his tongue into the action.

Minchin - trapped in the role of having to play a passionate, willing woman - had to not just withstand the fact that he was being tongued by another man, but also had to act like he was enjoying it. Minchin did this by beginning to produce soft, feminine moans which increased the intensity of the black man's kisses even more.

Three minutes later, Minchin felt the hand around his waist fall away. This worried Minchin, because it was a high priority for him to know where this guy's hands were at all times to prevent any nasty surprises.

Minchin knew the runaway hand's position the moment it began to squeeze his left boob. The soft mass of flesh on Minchin's chest was squished, bounced, and jiggled inside the man's thick fingers, reminding Minchin over and over about the two heavy masses on his body that he so desperately wished were not there.

After a full minute of this, the man's hand began to slow its pace. Then, it pulled down the cups holding up Minchin's bosom and popped both his tits out. With nothing to support them, they flopped downward into their natural(?) positions atop Minchin's breast bones.

As Minchin and his new 'daddy' continued to suck-face with each other, the hand on Minchin's tit started concentrating its efforts upon the unwilling-shemale's now rock-hard nipple. The man began to rub it between his thumb and index finger, attempting to stimulate Minchin as one might a woman.

If Kimberly King was a really a regular woman, the man's efforts to stimulate his nipples might have had the desired effect. Instead, all the man managed to do was irritate the fuck out of Minchin, who still found the new position of his nipples - being pushed away from his body by two, soft, gelatinous masses - horribly strange.

Still, Minchin knew that his job here tonight would be to put on a show, and put on a show he did. He moaned into the man's mouth as the man continued his attempts to stimulate him, and his lover, encouraged by the audible feedback, began to moan deeply into Minchin's mouth himself.

Finally, the man took his mouth away from Minchin's.

As the guy moved his face down to Minchin's tits, Minchin dry-vomited. Kissing this burly African man was one of the most disgusting things he had ever done. Even after the kiss, the feel and taste of the man's tongue in his mouth haunted him, right up until the moment another horrific situation presented itself.

The man started licking Minchin's tits.

Minchin felt the guy's warm, slimy tongue slide over one of his nipples repeatedly. He thought the guy was done at one point - something Minchin was insanely happy about - but it turned out that he hadn't stopped and was just moving his face over to start licking the other boob.

Minchin moaned out loud and screamed silently as the man began flicking his tongue from side to side over his tits, still continuing in his quest to stimulate Minchin the way one would a normal woman. If one were to have looked inside Minchin's g-string, one would have seen that his efforts were not successful: Minchin was as soft as a piece of rubber, and his dick felt no pressure whatsoever to change.

After five straight minutes of having to endure the irritation that came with having his boobs licked, something even worse happened.

The black man slid his hand in between Minchin's legs, and began to rub the crossdressing criminal's crotch. His hand traveled over the flatness underneath Minchin's white, lacy g-string for thirty seconds, until it finally decided to take things to the next level.

The man slid his hand into the front of Minchin's g-string, while continuing to lick the little guy’s melons. There, the hand began to explore, trying to figure out exactly what kind of equipment 'ts-kk' from Finding Arrangements had down there, and how she had it stowed away.

Within seconds, the man found the tape Minchin had used keep his balls inside the two canals from which they had long ago descended. After that, the man discerned the configuration of Minchin's long, impressive shaft, taped down over his scrotum and sitting just inside his ass.

Then, something that happened that gave Minchin one of the greatest shocks he'd ever received.

The man ripped a piece of tape off Minchin's scrotum in one, quick, unexpected movement.

As Minchin felt his right testicle come free, the world began to spin before his eyes. The guy had managed to take a thousand or so of the fine hairs on Minchin's scrotum along with the tape, causing him to feel as though he'd just been waxed on one of the most sensitive areas of his body.

Minchin's entire body went rigid as he braced himself for the removal of the second piece of tape.

Again, the pain was sudden and excruciating as the tape came free and his ball dropped out. Sting accompanying the movement caused Minchin to whimper like a little girl.

Without even asking for permission, the man then freed the rest of Minchin's penis, and it suddenly dawned on the crossdressing criminal what this guy intended to do.

Minchin has listed himself as a shemale on the website where this was all arranged. Unlike his tryst with Benjamin Davis, his dick wasn't to be kept out of the action here. Daniel Minchin's penis was going to have to be involved in the terrible events that were transpiring there that night, and, suddenly, Minchin knew it. He was about to object to his penis being involved in the night's activities, but it was too late.

Minchin's enormous, flaccid member entered the man's hand. When the warm skin of that hand quickly wrapped around the shaft and gave it a gentle squeeze, Minchin experienced the ultimate humiliation. Nothing he'd done with Davis had ever been as bad as what he knew was about to happen.

For a moment, Minchin's lover ceased his activities around the sole set of boobs in the room, and looked the owner of those boobs in the eye. "I was happy when I read your profile," he said, as he started, to Minchin's horror, to tug gently at Minchin's dick.

Minchin closed his eyes for a moment and wished upon wish that his penis - now in the possession of a large black man - would not become erect. If this ugly bastard somehow managed to get him up and make him hard, Minchin's entire world would be thrown into chaos. Minchin was a straight man, and a straight man getting a hard-on while being fondled by a burly black man was not something that happened. On the off-chance it did, Minchin's view of himself as a ladies man would be annihilated in an instant, as would his right to ever again call himself a man.

"Why were you happy?" Minchin asked the guy, Kimberly King's voice unsteady.

"It's not often I see girls like yourself so well-endowed."

Minchin feigned a chuckle that came out hysterical.

"Most girls I've been with," the man continued, still jerking Minchin slowly, "have all had what people like me call 'baby dick syndrome."

By 'people like him', Minchin figured he meant tranny chasers.

The man moved his hand down and cupped Minchin's soft penis and testicles from below. With the index finger of his other hand, he began stroking the length of his lover's shaft.

"I'm glad to meet a girl that doesn't have a baby dick," the man said. "I love a well-hung tranny."

Minchin smiled his first genuine smile of the night. At least there was one saving grace in all of this: having a giant dick was something Minchin was immensely proud of, and he loved hearing it, even if someone was referring to it as a tranny-dick. "Thank you," Kimberly's voice replied.

The two men locked lips again for a time, before the man stopped and looked at Minchin's crotch. "Why aren't you hard?" he asked, eyeing the still flaccid member sandwiched between his fingers. "Are you non-functional?"

Anger rose in Minchin's chest. "No," Kimberly replied, her voice low and bitter. "I'm not non-functional." Minchin, the narcissist that he was, was not going to let anyone in the world believe that he was impotent; not even this asshole.

"Then what's wrong?"

"I just took my hormones for the evening. I'm always soft when I do that."

A crease formed between the man's eyebrows, but he eventually shrugged and resumed stroking.

After a while, though, the man seemed to become agitated about the fact that he couldn't get Kimberly up. As such, he tried a different tactic to get the job done.

He removed his lips from Minchin's, and then lowered his face toward Kimberly's giant dick. Then, still stroking the penis, he began to speak to it. "Come on, little one," he said to the crossdresser's dick in a hushed tone, as one would speak to a very young baby, or when addressing a particularly skittish animal. "It's okay. I'm not going to hurt; your daddy would never do something like that. I'm going to protect you, and make sure that you have a good time. Come on, beautiful thing. You can do it. I know you can."

Minchin had to resist the urge to drive his fist into the side of the guy's head for doing that to his dick. There was something about the way he babied it - about the way that he treated it like it wasn't a symbol of Daniel Minchin's power and strength and instead as something that was weak and helpless - that made Minchin want to fly into a rage, consequences be damned.

As the man continued to whisper soft, calming words to his penis, Minchin realized that the worst was still yet to come.

All of a sudden, before Minchin could stop it, the man put his mouth around his impressive shaft. He felt his dick fill the man's warm, slimy mouth, just before he began to move his head up and down in rapid succession.

Thirty seconds later, the unthinkable happened.

Minchin's penis began to harden.

As his member grew increasingly more stimulated by the man's twisted actions, its size grew more and more.

Eventually, Minchin was as hard as a rock, and his spirit was irrevocably broken.

"What a good girl!" the man told Minchin's penis, feeling its new stiffness and girth with one hand. "I knew you could do it!"

Minchin barely heard that words that were being spoken, because, inside, he was dead.

The guy tugged on Minchin's wrinkled penis very slowly and gently for a time, before sitting back from the humiliated conman, leaning on his hands, and unzipping his fly. "Your turn, princess." He placed a firm hand behind Minchin's head and pushed it downward, indicating that the crossdresser should put his mouth where he wanted it to be, and start doing the job he was hired to do.

Minchin, almost utterly inside his own head at the moment, barely registered what it was the man wanted him to do. It took him a full thirty seconds to gather himself, before helping his lover out of his pants, and leaning over the enormous bulge in his underwear without even a hint of resistance.

Minchin began pashing the guy's bulge through his underwear. He watched that bulge grow bigger and bigger with each contact his lips made. When the dick had apparently reached full size, Minchin's eyes began to bulge out of his head. This guy's dick was enormous: the biggest that he had ever seen. And, somehow, Minchin was going to have to stuff its entire length into his mouth. This was not going to be fun.

Minchin kissed the head of the guy's penis, just as his hand found its way back around his dick. He started tugging on it again, despite Minchin's attempts to inch it away from his grasp: Minchin's new daddy seemed to consider it extremely important that his baby didn't go soft.

Moments passed as Minchin procrastinated. He was not looking forward to what was going to come next.

When he'd worked up enough gumption, Minchin did it: he removed the man's penis out of his underwear, and the dark, circumcised horror was revealed.

The firm hand started pushing on his head again, and Minchin knew he had to obey.

Within the next few moments, the crossdressing criminal was living his worst nightmare:

Daniel Minchin was sucking a black man's cock.

He did that for almost twenty minutes, and then pulled away.

The men then mutually masturbated each other, until Minchin's daddy scooped his baby up in his arms, and moved her small, malleable body further onto the bed. Standing on the side of that bed, the man pushed Minchin's stockinged legs apart and forward, until the conman's legs were above his head, his ankles were around his lover's neck, and his body was folded into a v-shape.

Now that Kimberly had been optimally positioned, the African man's eyes locked onto the giant schlong sticking out of Minchin's crotch. He smiled at it and gave it a little massage as a reward for being a good girl and staying hard. After that, Minchin's asshole came into his crosshairs.

The guy spent the next several minutes lubing Minchin's ring up, while Minchin just laid there, barely conscious of his surroundings. When Minchin had been sufficiently lubricated, the man stared into Kimberly King's vacant eyes, and pointed at his own dick. "Do you think you can handle it, baby?"

Minchin shook his head.

The man laughed, and leaned down over the recumbent Minchin. "I'll be gentle."

Minchin gulped, and whispered incomprehensibly in reply.

When the man's enormous dick slid into his asshole, Minchin's mind snapped back to reality.

When the guy started pumping his dick into his asshole, Minchin had to stop himself from reaching over to the pair of scissors on the bedside table and shoving the sharp end into the man's neck.

He managed to restrain himself, before adjusting the position of his ankles on the man's shoulders, and resigning to being fucked up the ass by another man. Again.

With each terrible pump, Minchin's earrings jangled; his tits jiggled; and his dick flapped weakly against his own, flat stomach.

A minute into the torment, Minchin found himself moaning, like a woman, involuntarily. He couldn't help it, and there was nothing he could do to stop it. There was just something about what this giant black man was doing to him that forced those high-pitched, effeminate moans out of him. Whether it was the pain from being fucked by this man or something else entirely, there was little difference - Minchin just couldn't keep himself quiet. All he could do was to lower the volume, so the women in the apartment next door - the ones he'd pictured having a pillow fight earlier - couldn't hear his shame.

As Minchin lied there, being raped and violated by his own choice, the man's eyes did not waver from the crossdresser's. Being fucked up the ass by another man was one thing, but, to Minchin, being constantly watched while the deed was being done was ever worse. He decided at that moment that, if he ever managed to bring himself to have anal sex with a man again, he would never allow it to happen in this position.

After fifteen solid minutes of this man hammering his dick into Minchin's ass again and again, finally, he was done.

With a deep, low roar, he pulled his dick out of the defeated Minchin's asshole, and came all over his stomach and breasts.

Minchin felt the thick, hot streams of jizz dribble down over his hairless skin and over his nipples, and he barely prevented himself from vomiting again.

The man returned himself to the bed, and leaned over Minchin, smiling down at him from above. Then, he grabbed ahold of Minchin's dick, and started tugging.

Minchin wasn't surprised at all when he felt his flagging dick become solid once again. After seven minutes of solid wanking, Minchin finally came himself, adding more sticky goo to his already defiled stomach.

The man then lied beside Minchin, and brought the smaller man into his arms. He held him there and stroked his hair for forty minutes before Minchin finally managed to extricate himself to have a shower.

In that shower, while the scalding hot water poured down over his body, Minchin cried like a little girl - emitting horrible, gut-wrenching wails - until, finally, he decided that he was clean.

An hour later, Minchin was outside the man's door. His lingerie was back over his body; his tits were away; and Minchin was once again inside his ladies coat.

The black man played with Minchin's earrings, and smiled stupidly at him. Minchin felt obligated to return the man's dumb, love-struck expression.

When the guy placed both his hands on the sides of Minchin's face and moved in for a kiss, Minchin breathed a sigh of relief into the man's mouth.

Finally, it was over.

"Ooooh!"

Minchin pulled his lips away from the man's mouth to find two attractive and obviously drunk women leaning out of their door, staring at him.

When Minchin and his sugar daddy spotted them, they ducked back into their apartment.

Then, the humiliation hit Minchin right in the gut:

Two gorgeous women just saw him locking lips with another man.

Minchin bid tonight's lover a short farewell, and greedily took the $3000 that was his payment for tonight's services out of his hands.

Minchin counted every note until he was satisfied that he had received the exact amount they had agreed upon.

"I'll call you," the man said.

Minchin resisted the urge to tell him that him saying that made him want to change his phone number. Instead, he smiled coyly, rotated on his heels, and made for the elevator, hoping that, when it deposited him on the bottom floor, he would never have to see this place again.

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