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Must Be My Lucky Day

Category: Gay Male
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He didn’t move. He just sat on his girlfriend’s bed and kept his eyes on her open closet. Eighteen-year-old Edward had only one thing on his mind. But his girlfriend would never accept it even if she was more open-minded than anyone else. The young black man tried to repress his temptation, but it always fought back and sought its victory. One look at Cheryl’s beautiful red dress and he would do anything to wear it.

He memorized even the tiniest details. The halter neck, the long skirt, and the sleeveless sides made him appreciate his girlfriend’s choice of clothing. So much so that he couldn’t wait to try it on.

When she entered her own room, Cheryl asked, “Is there something wrong?”

Edward immediately replied, “No, nothing’s wrong. I’m just relaxing.”

His blonde girlfriend giggled. “Well, I hope you enjoy your stay. I have to go out and see one of my friends down the block. It’s nothing serious, but it’s important. It’ll only take an hour or so. I can trust that you won’t do anything stupid in this house.”

Edward smiled. “Trust me. I’ll be fine.”

“That’s good. I’ll be right back.”

She gave him a kiss and left the room. Edward could hear the front door from downstairs opening and closing. He took a long deep breath. He knew that this would be a good opportunity to imitate Cheryl’s current persona by trying on her red dress, but he still tried to ignore his temptation. He slowly tapped his fingers on the bed. He continued to stare at the dress hanging from the open closet. He began to tremble. If he ignored his most powerful aspiration for much longer, then his regret would be in the form of a gloomy condition.

He finally stood up from the bed and stepped closer to Cheryl’s closet. He grabbed the red dress and raised it up to his body. He looked in the mirror to see that the dress might suit him after all. He was a slim young man with a thirst for femininity. He took off his shirt, pants, and even his boxer shorts. He remained incredibly careful when putting on the dress. He didn’t want to leave any obvious evidence that he had worn it in secret.

It felt just right. Edward looked in the mirror to see that he looked rather stunning in his girlfriend’s dress. His long dreadlocks could have been seen as a woman’s hairstyle now that he found himself in the apparel of the opposite sex. He couldn’t help but smile. The skirt ended at his knees and the halter neck felt comfortable. He breathed a sigh of relief. Feeling so girly made him want to buy this particular dress for himself.

He turned away from the closet and set his attention to the open balcony. He stepped out of the bedroom and stayed on the balcony. He gazed at the gorgeous scenery that Cheryl would see every single day. The mansion was situated on the hillside along with many other homes owned by people who prospered. Edward received a clear view of the distant ocean down below. The coast was tranquil, with plenty of beachgoers spending their day on the sand. The cool ocean breeze made Edward feel composed. Living in the city of Malibu was a dream come true. He felt grateful that he belonged to a rich family just like Cheryl. And now, the familiar experience had been further enhanced thanks to the red dress that made him no longer fear his future decisions.

He closed his eyes for a moment. He felt so much like a woman that he imagined walking across the seashore wearing this exact dress during sunset. If only he had the time to do so. Seeing as how Cheryl did mention that she would return home in an hour or so, he couldn’t take such a risk today.

Sighing, he turned around and walked back inside the bedroom. And suddenly, he gasped. He spotted someone standing at the open doorway. He stood frozen. He didn’t expect Cheryl’s father to arrive home from work at this time. He didn’t know what to say. Vincent just stood there looking rather amused at his most recent discovery.

With eyes wide open, Edward now regretted his decision to wear such beautiful attire. “Uh…hello…I…”

Vincent chuckled. “Why are you wearing that?”

Edward shivered. “Forgive me, but…I was just trying it on. I, uh…I thought it would look good on me. But don’t worry. It’s not like I do this all the time. I’m sorry. I shouldn’t be wearing this. I know that Cheryl likes this one very much. I’ll just take it off.”

Vincent stepped closer. “Take it off? Now why would you do that?”

“Well, it’s because it’s Cheryl’s and I had no right to wear it without her permission.”

A little smile formed on Vincent’s face. “Oh, don’t worry. I must say that it DOES look good on you.”

Edward tried to laugh, but failed. “Yeah, I’m sure I look good. But I don’t think I should wear it anymore.”

“No, don’t do anything. Just stay like this. It suits you very well.”

“It does?”

Vincent’s baritone voice seemed very soothing. “As a matter of fact, I think I like you this way more than your true self.”

He now stood just inches away from Edward, who tried to calm himself after getting caught.

“Wait…you like me this way?”

Vincent eyed him from top to bottom. “You look better in this dress than my daughter. Maybe I should persuade her to give this to you as a gift.”

Edward couldn’t look away from Vincent’s hypnotic stare. “I don’t think that’s a good idea.”

Vincent slowly licked his lips. “I’m so glad that you’re wearing this. You look absolutely perfect right now.”

Edward felt like he was going to faint. Standing in front of Cheryl’s forty-three-year-old father was just too much to handle at the moment. The middle-aged white man did look very handsome. His tall stature and broad shoulders made him appear to be an ideal catch for single women. Edward, who was a few inches shorter than Vincent, didn’t know whether to stand still or to just put the dress back in the closet.

He asked, “So should I just put it back in the closet?”

Vincent gave a light but almost devious chuckle. “Stay where you are. This must be my lucky day.”

He grabbed Edward by the arms and turned him around. Shocked by the sudden move, Edward couldn’t help but feel speechless.

Vincent whispered in his ear, “Don’t be afraid. Just be your sweet self.”

Edward could feel the older man’s hands sliding down the dress before they pulled up the skirt and reached down between his legs.

Edward gasped as soon as Vincent closed his fingers around the exposed cock. Feeling incredibly nervous didn’t help with his situation. All he could do was stand still as Vincent, from behind, locked him in a tight embrace while stroking the cock that experienced a slow erection. 

“Vincent…what are you doing?”

“Hold still. Let’s see how well you can act like a girl.”

“But, I-“

“Just become what you’ve been pretending to be.”

Edward couldn’t say anything else. He looked down as Vincent continued to caress the younger man’s cock. He started to imagine his dick being replaced with a woman’s vagina. And instead of Vincent stroking it, he rubbed the clit hard with his fingers. Edward closed his eyes. He began to moan like a young woman.

“Oh, Vincent…I like it.”

He didn’t know why he said it, but he knew that it had everything to do with Vincent’s thirst for someone’s simple submission. He continued to moan in a more girly manner. He trembled in Vincent’s arms. The feeling between his legs made the situation more exhilarating than usual. Vincent’s fingers gained more speed, while Edward gained a little more animation now that the truth had been revealed in Cheryl’s father’s eyes. He soon recognized the feeling that women received when they said they “got the tingles.”

He could feel Vincent kissing him on the neck, another erogenous spot that made the young man easier to submit.

He even started to talk like a female. “Oh, yes. I like it. I like it very much.”

Vincent chuckled. “I like you this way.”

Edward took quicker breaths. He could feel his cock about to erupt in a few seconds thanks to Vincent’s fast fingers. He didn’t even care if he made a little mess on Cheryl’s dress. The desire to be used by Vincent grew even more.


And then, Edward’s wish began to come true. Vincent still didn’t stop stroking Edward’s cock even as big blobs of cum shot out of the tip and landed on the hardwood floor. Edward moaned in his newly formed feminine attitude. He looked down to see his own semen in the shape of small thick puddles.

“Holy fuck, it actually happened.”

Vincent turned him around to give him a rather more devious stare than before. “We’re still not done yet. Come here.”

He brought Edward closer to Cheryl’s king-sized bed. He loosened his belt. “Don’t go anywhere. I still have my own load to blow.”

Edward watched as Vincent took off his pants, boxers, and shirt before tossing them to the side. Edward now felt like a shy woman with the red dress on. He felt weak in the knees. He dreaded the outcome of this situation.

Vincent sat on the edge of the bed. “Take a look at my cock.”

Edward was mesmerized by the sheer length of it. “It’s so big and so long.”

Vincent smile grew bigger. “Yes, it is. I want you to sit on it right now.”

Edward took one step back. “Should I really be doing this? I mean, Cheryl could come back home and find us here.”

“Forget about her for a moment, and just think about what her FATHER wants from you. Sit on my cock.”

Edward took a deep breath. He didn’t run for the door. Instead, he obeyed. Still wearing the dress, he took a seat on Vincent’s lap. The two men now faced each other. Edward lowered himself down on the fully erect cock and readied for the inevitable sensation. Once it touched his hole, he tried hard not to squirm. Vincent just sat still while Edward slid the cock deep inside him.

He almost screamed. Having another man’s dick shoved into his hole was so unreal.

Vincent remarked, “Don’t give up. Move up and down. Be the woman you were destined to be.”

Edward moved his body up and down on the giant cock. He did it slowly at first. The penetration made him feel so vulnerable to Vincent’s commands. His submissive behavior matched with his girlish appearance. He brought his clenched fists up to his chest as the unfamiliar sensation from down below gave his feminine side a more determined push into reality. He moaned like a young woman losing her virginity on the spot.

“Oh, yes! It feels so good!”

His movements picked up speed. He bounced up and down on Vincent’s vertical dick, his inner weak spot being touched with every direct plunge. He imagined himself as the wife who pleased her husband after his hard day at work. He had the correct mentality as well. He didn’t stop. He let his girlish demeanor take control of him.

Vincent whispered, “Oh, you’re good. You should stay this way.”

All of a sudden, he grabbed Edward and brought him down on the bed. Edward lay flat on his back and watched as Vincent towered over him. He kept his cock deep inside the young man, and this time, it was his turn to make the movements. He began his pelvic thrusts. The thrilling sensation from within Edward’s body had grown more powerful this time.

“Oh, shit! It’s amazing!”

He no longer cared if he created a mess on Cheryl’s red dress. He just let Vincent take control while enacting the same sort of behavior that Vincent had yearned for.

They spent their time in Cheryl’s bedroom perfecting their proper roles. Vincent’s deep thrusts became a clear balance with Edward’s compliance. 

“Fuck me hard!”

Edward didn’t have a care in the world. He overlooked his girlfriend’s existence right when her father accepted his secret. He was pleased that Vincent preferred his unknown side of his life, though it did become a rather strange feeling. Vincent had been the only one who discovered Edward’s secret, and end result took place in such a short time. The thirst for Vincent’s cock didn’t expire at all. In fact, Edward adored his new personality even if only one individual had shared his satisfaction.

“Oh, yes! I love it hard!”

Vincent didn’t stop. Minutes had passed and he showed no signs of exhaustion. The fast-moving cock created a burning sensation from within Edward’s tight hole. The pain and pleasure of it didn’t force Edward to struggle. He just let it happen. He hadn’t felt this way before, and he had hoped that it would end much later. 

Several more minutes had passed, and Vincent finally gave the signal that he would be finish his performance.

“Here it comes!”

His last thrust was the most powerful.

Edward gave one of the loudest girly screams ever produced in Malibu. “Fuck, yes!”

He squeezed his eyes shut as both men reached their breaking point. Vincent finally stopped his infiltration. Edward relaxed, knowing that Vincent had just flooded his inner walls with ounces of thick warm cum.

And it was all over. Vincent finally pulled his exhausted locomotive out of Edward’s hole.

The burning sensation inside the young black man still lingered. “Shit…this really happened.”

Vincent got out of bed and put his clothes back on. “You’re truly one of a kind, Edward. You should stick around more often. I’m happy to see that Cheryl chose you as her boyfriend.”

He left the room without saying another word. Edward was now alone on Cheryl’s bed. The eighteen-year-old role-player breathed a sigh of relief. He closed his eyes for a moment. He still couldn’t believe what just happened between him and his girlfriend’s father. All it took was for him to dress up as a young woman and submitting to Vincent’s demands. Mixed emotions overwhelmed his thoughts. He felt glad that he had the chance to wear his girlfriend’s dress, but he also felt embarrassed for getting caught and being used by her father. Nevertheless, this had become quite an interesting experience. He didn’t know how a woman would act it taken by another man, but he did have an idea of it after what transpired in this room.

When he opened his eyes again, he turned his head to see Cheryl standing at the open doorway. The utter shock displayed on her face made him want to flee the scene and never come back.

She asked, “What the hell happened?”

Edward knew that she had just noticed him wearing her red dress and being surrounded by thick white cream embedded on the sheets.

He could only respond with, “I sorry, but…I don’t think you’ll believe what I’m about to tell you.”

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Muskan wrote

Very nice and erotic story I my self felt erection while reading the story