His Shooting Star

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A Delivery Boy Gets An Unexpected Tip.
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His Shooting Star

It was a typical Friday evening. Delivering pizzas was always on the menu for Rodge. He was off to deliver downtown, to a hotel in the rich neighborhood down the street from the red light district. For sure, he was about to get a generous tip.

Rodge soon arrived, made his way to the 17th floor and knocked on the customer's door. When it opened, he found himself face to face with one of his favorite TV stars, Erika Diamond. She was a bob cut blonde and muscular, but a very feminine, blue-eyed sexy woman.

Shocked, but trying to remain professional, he fumbled his words a bit trying to do his job and not gush. But this was his one fated opportunity to meet her, he couldn't pass it up. As starstruck as he was, he managed to express his fandom and love of her work. She smiled and invited him in.

His wits still about him to some degree, Rodge declined because he was on call for the night. However, at her insistence, he stepped in for a minute.

Erika placed the pizza on the table and coyly brought up the subject of his tip. She was clearly flirting and Rodge was in utter disbelief of the moment. But things became clearer when he noticed as she bit her lip and pulled down her pant zipper.

He wasn't prepared for what he saw. Erika had a seven inch surprise for him; A hard throbbing cock that stood at attention pointing at him as if he was its target. He had never been with such a woman before. He had never even considered it. He was straight. He had no problem with anyone in any walk of life, but he was firm in his own sexuality. Panic set in and he figured he had to make a break for it.

Rodge slowly backed up as Erika walked towards him. His back hit the door and as soon as he realized it, turned around to open it and run away. But she slammed it shut and put her other hand over his mouth. After locking and sealing off his only means of exit, she ran her hand all over his body firmly squeezing his genitals while grinding against him from behind.

Erika undid his pants and pulled them down enough to reveal his penis and his behind. Still holding him in place by gagging him with the one hand, she reached for her lube, took a handful and forcefully lathered Rodge's ass hole as well as her cock. Then, she reached around and grabbed his, got a good grip and slid herself into him.

The whole time, he was having conflicting thoughts and feelings. It's a woman with a penis, but it's also a celebrity, she's forcing herself on him, but is he actually enjoying it?

Erika's grip on Rodge's dick with the motion of fucking him, turned it into a handjob. She thrust in and her hand went down the shaft. She pulled back and her hand jerked upwards. He was being pleasured doubly. This kept him trapped in his mental battle of pleasure versus sexuality.

The motions got faster and more intense. Muffled, he could tell her neither to stop, nor that he was about to cum. But she knew based on his moans, so she went faster and harder finally exploding inside his ass. At the same time, jerking him off making his cum splatter on the door.

Rodge fell to his knees. Erika mockingly said "There's your tip", opened the door, kicked him out and locked the door behind him. He lay there trying to understand and believe what he had just experienced. That moment was quickly interrupted as he heard voices coming down the hallway. Rodge did up his pants and walked away trying to act normal as he left.

He got to his car and sat for a few minutes before making his way to his next customer. He reflected on what he was just put through. Did this make him less of a man to be dominated by a woman like that? Is he a homosexual now because he had an orgasm by a shemale? A ladyboy? A woman who wasn't always a woman? Rodge shook it off, refocused on his job and finished his shift.

The very next evening, he got a delivery call to the same hotel and room. He was specially requested by the customer. Obviously, it was his celebrity crush wanting to take advantage of him again. Rodge was very tempted. As much as he didn't want to admit it, he realized that he thoroughly enjoyed the night before. It felt good. Not only being pleasured, but having no control over it. Having his hot celebrity crush have sex with him, regardless of what was between her legs. But he was still apprehensive. Though, he did realize that she was someone famous. And no one in her position would take things too far and jeopardize their status. A feeling of calm settled in as he ascertained that he was safe. He went ahead to meet her again.

All through the drive there, he felt nervous energy. This time he knew what he was in for. He kept blocking out the fact she had a penis and focused on the fact that she was otherwise, a regular woman. Plus, it wasn't lost on him how lucky he was to be having sex with a celebrity.

Rodge finally arrived and eagerly, but nervously knocked on her door. Erika didn't hold any intentions secret this time. She was dressed in lingerie, ready for a night of debauchery.

Erika served him wine. She was happy at his willingness to participate this time. This left him a bit bewildered. Last time he was used aggressively and then thrown out like used trash. This time was definitely going the way of something more romantic. It was clear, she was going to take her time with him this go-round.

Erika leaned in, took Rodge's glass and put it down. She began to kiss him. All was going well, until he opened his eyes and saw the bulge in her panties. Instantly, his inner conflict began once again. But this time there was a way out. It wasn't being forced. This only made it worse, however. It was as if he were two people and one was trying to run for the door, while the other was holding him back. He sat there frozen in indecision.

With him petrified and unable to refuse, Erika began to lick his neck, sliding down to suck his nipples, which were extra sensitive and made him cry out in delight. The whole ordeal made him rock hard and put him on the precipice of orgasm. For some reason, the inner battle was turning him on remarkably. It was like once again being forced to enjoy it, but this time not by her. By part of himself.

Erika undid his pants and Rodge's erection popped out, ready for her mouth. She took a little taste of the precum, then engulfed his cock in her mouth. She sucked and glided up and down on it while staring up into his eyes. Thoughts swirled within him. "She's a transwoman, I'm straight, what's going on, I can't resist, do I want to?". It served to make the experience exponentially better. Before he could cum, she popped his dick out of her mouth, lay back, pulled off her panties and declared, "your turn".

The blood drained from Rodge's face, his eyes widened. This was something he couldn't ignore or convince himself of that she was just another woman. But upon actually being there gazing at this gorgeous woman with a hard cock, he couldn't deny how turned on he was. He WANTED to suck it. He had no idea what to do, except to do unto her what he would want done to him. So, he gave her the blowjob he would want. And it proved to work, for Erika writhed in ecstasy, enjoying it all while Rodge tasted semen for the first time. He was already an expert. Several minutes later, Erika pulled him off, afraid she was going to blow her load. They kissed deeply. Then Rodge proceeded to suck on her breasts. Her implants seemed so real that it comforted him, easing his thoughts of being with a transwoman. She turned over and beckoned his cock into her. He grabbed her hips and started to thrust in and out of her. From this position and viewpoint, he could only see a regular woman and this gave him back a sense of control. He pounded her with all his might.

They switched places. The memories of last night suddenly came flooding back. This time Rodge decided to just let go and enjoy every minute of it with full willingness. Neither of them came, except for a decent amount of milked semen from all the anal activity. How their sex would end would spike Rodge's inner conflict to its apex.

Erika took out her masturbation sleeve. She interlocked her legs with Rodge so that their balls pressed against each other. He recoiled for a moment. His genitals hadn't ever come into contact with ones like his own. He couldn't escape now. He was at the point of no return.

Erika lubricated the sleeve and put it on, but then she stretched it and brought Rodge's member into it as well. Their balls and cocks were pressed right against each other tightly. She began to gyrate and grind, gripping the tool for leverage. Rodge felt the unbelievably wonderful sensations of rubbing against another cock. He was in such a battle with himself at this point. This was beyond anything he'd experienced before. There was no way to pretend this was an average woman anymore.

The experience kept getting more and more intense and impossible to stop. He was helplessly scissored with Erika and got to a point where couldn't tell if he was trying to escape or grind with her. Rodge's feelings and sensations were so heightened with the need to leave the situation and at the same time to contribute to it. They both let out an earth-shattering roar as they came simultaneously. Rodge felt the contractions from both penises as they both pumped out globs of semen all over the encapsulation of the silicone toy.

The orgasm seemed as if it wouldn't end and neither of them wanted it to. However, it eventually did. They both fell back to recover, their penises still tightly bound together. Erika then slid off the sleeve to find both of their dicks covered in white foamy cream from all the friction. Rodge looked at it and verbally mulled over if he was now gay or not. Erika responded, telling him that he this didn't make that so. Lots of straight men have this fetish. She just helped him discover that he did as well. She grinned.

Rodge, relieved, but still confused, kissed her. They exchanged contact information while sharing a cigarette, then hugged and he left. From that day forward, he had a whole new perspective and fetish to explore. He often hooked up with transgirls comfortably and was grateful to his celebrity crush, or as he called her, his "shooting star", for introducing him to the sensual world of she-cock.

END

Written by PrinceJupiter

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PrinceJupiterPrinceJupiter5 months agoAuthor

@Anonymous, Thank you for your comment. It did feel rushed, even after trying to flesh it out more, but I just ran out of ideas. I might try again and update the original text one day. Thanks for reading!

AnonymousAnonymous5 months ago

I liked it. Especially the sleeve part. But if I may suggest a little more description and character development? It felt rushed.

I look forward to more from you. Thank you for writing.

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