Another Date (A Valentine's Day Revenge 2)

Hey there dudes and dudettes!

 I am back again with a new captain. This time a Patreon Request by "Jägerin110 who wanted to see a sequel to my cap A Valentine's Revenge, where Carl would be blackmailed by his sister to go on another ate while once again having to stand up his girlfriend for it!

I hope that you all like it!
And with that, I take my leave again, and until next time, stay happy and healthy!

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"Wakey wakey, sleepyhead" was the first thing Carl heard as he was awoken from his sleep, and he groaned as he slowly got up, his head throbbing from the voice.

“Leave me alone, Sarah,” Carl groaned out, his own voice sore and hoarse as he pressed his eyes closed as hard as he could to shield them from the daylight.

“Aww, don’t be like that,” his sister just replied as she opened the curtains, making Carl groan louder, but before he could hide under his covers, they were pulled away by Sarah.

“God, what the fuck do you want?!” Carl now shouted, wincing slightly as it just made his head hurt more, but he was fed up enough with his sister that he didn’t care much at the moment.

“Oh, I just wanted to tell you how good of a date you were last night,” Sarah said with a giggle, and despite his drunken haze, Carl knew exactly what his sister was talking about.

He clearly remembered how he was forced to go on a double-date with his sister as a girl and how their male dates awaited them at the door.

He clearly remembered how both men towered over them, how Jack took his sister's arm and led her towards the car while his own date Mack wrapped an arm around his waist.

He clearly remembered how Mack groped his ass all the way to the restaurant, how Mack’s eyes never left his cleavage or how Mack touched him on his legs.

He clearly remembers how he ordered drink after drink, hoping it would help him cope with Mack’s unwanted advances or at least make him forget this evening.

And apparently, the alcohol worked; at least Carl was unable to remember anything after they left the restaurant and headed to a nightclub for some dancing.

“In fact,” Sarah continued, ripping Carl out of his little road down memory lane. “Mack was so happy with how the date went that he wants another one soon!”

“W-What?” Carl replied in shock. “No. Forget it; there is no way I am going on another date. Nu-uh,” he vehemently denied, only to receive a smirk from his sister in return.

“Oh, I think you will go on another date, Charlotte,” she sang, taking out her phone that had pictures of Carl all dolled up. “At least if you don’t want your girlfriend to see your feminine side.”

That made Carl pause as his eyes widened, not believing that his sister would blackmail him like that. “Y-You can’t do that!” he squeaked out, but Sarah's grin just got wider.

“Oh, I won’t, Charlotte. But you know what you have to do for me in return, right?” she said, watching her brother go pale. “G-Go on a date with Mack…” he meekly let out with his head hung low.

“There you go! Good girl!” Sarah praised her with a giggle. “Well, now that we came to an understanding, I will leave you to your beauty sleep! I will let you know when your next date is, alright?”

With that, Carl’s fate was sealed, and for the next weeks, he was waiting anxiously, trying to forget about his situation, while every day the threat of being on another date hung over his head.

And 3 weeks later, just when he thought that his sister would not actually make him go on a date, the said girl burst into his room in excitement, and Carl immediately knew what this was about.

“Charlotte, guess what?” Sarah asked with a singsong voice. “You have a date with Mack again today, so it is time we get you ready!”

“What?! Sarah, no! I promised my girlfriend a date today after you forced me to stand her up on Valentine's Day! I can’t go out with Mack!”

“Oh, don’t be like that,” Sarah just said, waving her hands. “You can have a girl’s  night out on a alter date, but today you are going to go out with Mack!”

“NO!” Carl shouted, finding some confidence. “You know what? I am done! Come, send the pic you have off me. I will just say I lost a bet or made a dare!” he said with a grin, thinking he had bested his sister.

Though instead of cowing, Sarah just grinned and grabbed her phone. “Well, you can do that. But I think it would be hard to explain why the dare involved giving some guy head.”

Carl's eyes widened as he looked at the screen where he could see himself, his head positioned right at Mack’s crotch while the pants of the guy in question were around his ankles.

“Just look at you going to town! Up and down, up and down, up and down!” Sarah exclaimed in glee as Carl went completely wide. “Apparently, you were too drunk to remember, but luckily, a camera never forgets! So unless you want this video to go to your girlfriend, you better get yourself ready for your date!”

Knowing there was nothing he could do, Carl just undressed and took the items his grinning sister gave him, knowing he would be feminized once more.

Since he was still hairless from last time, Sarah immediately glued on the breast- and hipforms from last time before forcing a corset around his midriff, returning Carl to his previous curvy figure.

Next, she grabbed a corset from her closet and wrapped it around Carl‘s stomach before starting to pull on the strings, trying to make the corset as tight as possible.

Next came the underwear, and reluctantly, Carl pulled up the pink lace panties up his legs after he gave himself a tight tuckjob, followed by an equally lacy and pink bra.

After that, Carl grabbed the pink dress Sarah picked for him and put it on, the glittery pink latex dress once again being tight and short enough to leave nothing to the imagination.

“Oh, Mack is going to love your outfit!” Sarah laughed, and Carl turned red in embarrassment, not believing that he once again was looking like a convincing woman.

“Now I know that you don’t know too much about make-up yet, so let your big sister help you out a bit, alright, Charlotte?” Sarah said, and before waiting for an answer, she grabbed a variety of make-up utensils, from brushes to creams, and pounced on her brother.

And so Sarah began the make-up by generously applying foundation, giving him a a fair complexion, followed by some light blush added to his cheeks.

Since his lips were still swollen from the last injection, she just grabbed some lip-plumper and pink lipstick to make her brother’s lips appear soft and kissable.

Next came the eyes, for which Sarah glued on some fake lashes before covering them in mascara, followed by eyeshadow and eyeliner to give Carl the perfect smoky bedroom eyes.

She then attached some star-shaped earrings to his ears before she took the same wig as last time and once again glued it to his head, putting it into a high ponytail.

Lastly, she glued on some fake nails again that she painted pink with white polkadots before putting a thin necklace around his head and putting his feet into 6-inch white platform heels.

“Wow Charlotte, you look even better than last time!” Sarah laughed, and once again Carl could only stare in shock as he saw his reflection in the mirror, unable to believe the sexy girl staring back was actually him.

“I bet that Mack won’t be able to keep his hands off of you! And I bet you are looking forward to this, aren’t you, you little minx?” Sarah joked, and Carl could only swallow hard.

“N-No, I d-don’t…” he meekly said, making Sarah laugh out loud as she wrapped one arm around her brother’s shoulder and started leading him downstairs.

“Oh, don’t be so shy, put out on the first date after all! But this time you are better prepared” Sarah said, handing her feminized brother a white purse. “Here. There are coughdrops, lube and condoms. You know, the essentials” she said with a wink.

Carl recoiled, his eyes wide, but before he could say anything the doorbell rang. “Oh, that must be Mack!” Sarah exclaimed as she pushed Carl faster towards the front door.

“Well, have fun sis!” was the last thing she said before opening the door and pushing Carl into Mack, making sure that her feminized brother didn’t forget his purse before watching how Mack escorted Carl to the car, his hand never leaving the fminized guys ass.