Valentines Trap

Hey there dudes and dudettes!

It is Valentines day, the day of love, and of course I made a caption for this special day!
This is actually a requested idea by Li3L4, and I have to say I quite liked it!

I hope that you all enjoy the cap, and that you have a good Valentine's, whether it be together with your partner or alone!

There should also be coming another Valentine's cap later this week, so stay tuned!

And with that I hope to see you all next time, and stay happy and healthy!

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"Stupid Valentine's Day, probably the most idiotic day of the year" Lyle grumbled to himself as he slowly made his way across campus, looking in disdain at the happy couples around him.

"Pshh, don't these idiots know this is all just a scam? This whole freaking day just exists so florists can sell more overpriced flowers and shops can sell cheap chocolate that nobody usually buys."

He continued to grumble to himself, his feelings towards Valentine's Day clear, and not at all influenced by the fact that he had no significant other to spend the day with like every year.

But just as he was about to leave the college grounds he was stopped by someone from behind.

"Hey Lyle, wait up!" a girl shouted, making said guy turn around, and in doing so he saw that Riley, one of the most popular and beautiful girls in his class, was the one wanting his attention.

"H-Hey Riley" he stammered a bit, confused about what she wants from someone like him, after all they hardly speak to each other in class, and he is far from popular "What's up?"

"Oh, nothing much" the beautiful blonde replied, giving him a smile as she played with her hair.

"I just wanted to know if you are free today? If so maybe you wanna come over to my house?"

This shocked Lyle, and inwardly he was shouting yes, thinking he finally got someone to spend Valentine's Day with, and so he immediately agreed to Riley's invitation.

"O-of course. I would love to!" he nearly shouted, barely able to contain his excitement, making the blonde giggle. "Great, it's a date then! Just come over in around 3 hours, alright? See you later!"

With that Riley made her way home, giving Lyle a small wave before she left.

Meanwhile the boy in question hurried back home, thinking about how great of a day this was before he changed into fancier clothes and went out to buy flowers and chocolates.

And as he promised three hours later he was in front of his classmate's door, chocolates and roses in hand as he was ringing the doorbell and nervously awaited for Riley to open.

"Oh hey Lyle, just on time!" she said as she opened the door, leading him into the living room before taking a look at his presents. "Oh, thank you, they are wonderful. But you shouldn't have!"

With that Riley grabbed the roses and put them in a vase and put the chocolates away before the two spent nearly an hour chatting away, with Lyle being quite nervous all time long.

He became even more nervous, but also quite excited, when after some time Riley started to scoot closer and closer, her hand playing with the hem of his pants as she gave him a sultry look.

"Say, Lyle, why don't we take this date of ours upstairs?" she whispered into his ear, and without losing any time he agreed as they made their way to her bedroom where Lyle began to undress.

But as he was standing nearly naked in front of his date he just saw her looking him up and down, biting her lip and avoiding his eyes. "Is something wrong?" he asked, unsure what the problem was.

"No, it is nothing, it is just..." she started, sounding quite unsure before letting out a big sigh.

"It is just that I really like feminine-looking guys, you know?" Riley finally said out loud.

"What?" Lyle just said, confused as he did not understand what his date was getting at.

"I just would really love it if I could dress you up in some of my stuff" said Date quietly answered.

"You know, just for a bit of fun!" she hurriedly continued, stopping him before he could retort. "Please? I will make sure that it is more than worth it for you in the end! I will give you a night you won't be able to forget in a long time!" Riley began to beg, giving him a pleading and needy look.

This made Lyle hesitate, after all he did not really like the idea of getting dressed up as a girl, on the other hand a night with Riley he would not forget sounded VERY tempting to him.

"Alright" he finally said after making his mind up. "But you better make good on your promise!"

"Yay!" Riley cheered at her victory, giving Lyle a short kiss on the lips. "Don't worry, I will! Now just take this and make sure to shave!" she continued, handing him a razor and cream.

With a bit of reluctancy he grabbed the items and made his way to the bathroom, where he began to shave, though he was irritated that he now smelled like flowers thanks to the cream.

When he returned from the bathroom Riley smiled at him in satisfaction as she saw his hairless body before she grabbed some breast- and hipforms that made Lyle's eyes go wide.

"Don't worry, this is all just part of my fantasy" she said, and before Lyle could say anything she attached the forms to his body, never mentioning the glue they were slathered in.

Next she grabbed a corset, and without any other warning she wrapped it around his torso and pulled it tight, creating an hourglass figure that made Lyle struggle to breathe properly.

"Wow, this is making me so hot right now" Riley whispered sensually, making Lyle forget most of his troubles as he just imagined what reward would come after this whole ordeal.

Said ordeal meanwhile continued as Riley started to dress Lyle up in some of her clothes.

She started by grabbing a pair of black lace panties with a hole in the back and pulling them up his legs, making sure to tuck his privates back with some glue she secretly put on them.

After the panties were in place Riley grabbed a short shoulderless black dress that she pulled over his head, struggling a bit with his new breasts, before pushing the black sleeves up his arms.

The dress in question was quite short, just barely reaching over his ass, threatening to reveal his panties with every large step, while being quite tight in the chest area, leaving a lot of cleavage.

Once she was happy with how the dress fit Riley put some red thigh-high fishnet stockings onto Lyle's legs before she finished the outfit with some plaform dolly shoes with red hearts on them.

"Wow, you are turning out perfectly" Riley said, her eyes full of excitement as she ran her hands all across his body, making Lyle shiver from the contact and look forward to his date's promise. "Now we are just missing some makeup, then we can have some fun" she continued, putting a heavy emphasise on the word fun, and her voice sent tingles down Lyle's spine.

With that she began by smothering his face in foundation, before she took some tweezers to put his eyebrows into thin feminine arches, followed by gluing on some big fake lashes to his eyes.

Next Riley covered the new lashes in mascara before giving Lyle some doe eyes with the help of black eyeliner, which was quickly complemented by some slightly blue eyeshadow.

After that came the lips, which she applied generous amounts of pumper to before covering them in multiple layers of gloss before she grabbed a glue-filled red wig and attached it to his head.

For the final part of Lyle's transformation Riley clipped some earrings to his ears alongside grabbing a few necklaces she put around his neck that put further emphasis on his cleavage.

"Aand we are done!" Riley happily announced, making Lyle excited as he was now closer than ever to his deserved reward. "Common, give me a pose so I can show you the results!" she continued.

Lyle did as he was told, going as far as to make a feminine pose he saw some models do to make his date happy, and from her giggles his work was appreciated as she took picture after picture of him.

"Oh, you look amazing like that, Layla! Chad surely will be satisfied to have you as his date!"

"Yeah, well, I-- Wait... Layla... Chad... date?! WHAT?!" Lyle began to say, only for Riley's words to finally sink in. Causing him to shout out in shock and confusion, not knowing what she meant.

"Yes Layla, date" Riley explained, acting as if this was the most obvious thing in the world.

"You see, I have no interest in Valentine's day. It is just that Chad - you know, the school's quarterback - pestered me about a date for weeks now, not taking no for an answer!" she ranted.

"But luckily I convinced him that my friend would be happy to be his Valentine's. That is you by the way, Layla. And if you want the solvent to the glue and those pictures you better do as I want!"

Finally the gravity of the situation hit Lyle, but before he could protest or beg the doorbell rang.

"Oh, that must be Chad!" Riley said before grabbing Lyle's hand. "Common, don't keep your date waiting, Layla!" she continued as she dragged the poor feminized guy downstairs to his fate.

And as expected Chad was at the door, handing Lyle some flowers and chocolates – the same cheap gas-station stuff he gifted Riley – that Riley quickly took inside to deposit them appropriately.

"Now you two have a nice date!" Riley shouted as Chad led Lyle to his car, the quarterback's much taller and muscular figure easily dwarfing the feminized guy as his big hands fondled his ass.

"And remember Layla: Take all the time you need to make your date happy, alright?"

With those parting words Riley looked on as Chad escorted Layla into his sportscar, happy to know that her plan to get out of Valentine's Day seemed to work perfectly.

"Well, I hope you are ready for that macho guy, Layla" she said to herself as she made her way back into the house. "Because the other's girls told me that all his dates start straight in his bedroom."

And as if to prove her point the last thing Riley saw before she went inside was Chad grabbing Layla's head and pulling it towards his lap before he started pulling out the driveway.

"But luckily that is not my problem" she finished thinking to herself as she went upstairs, grabbing some ice cream before changing into her pajamas to spend Valentine's Day watching her favorite shows.