This Will Help (TG Caption)

This is my first caption, hope you enjoy.

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Charlie anxiously stood outside La Bella, a fancy Italian restaurant.

He looked at his watch, it read: 7:07.

It was winter and Charlie was beginning to shiver from the cold but the fact that Gwen would soon be there made it all worth it. Charlie had met Gwen a few months ago through an online dating site. After a few rocky messages back and forth the two had hit it off. Not one to play the waiting game Charlie was quick to ask her out, agreeing Gwen gave him her number and since then they had been on a handful of dates.

Tonight though was different. Tonight Charlie was going to ask Gwen if she'd want to go a step further and make their relationship official. So far he'd seen no reason as to why she would say no. They shared almost everything in common, every date they had been on she enjoyed and at the end of each one suggested another.

Charlie looked at his watch again: 7:09.

"Charlie!"

Charlie turned around and there she was walking towards him. He smiled and waved.

"Thought the cold would have made you think otherwise."

"What me? Oh come on, a little cold never hurt anyone... actually that's probably not true... anyway let's go in."

Charlie nodded as he got the door for her.

After sitting down, ordering and catching up Gwen noticed that Charlie seemed a bit nervous. Nothing major but definitely unlike him.

"Ok, what's up?"

"Huh?" Charlie replied.

"You seem odd, is everything alright?"

"Oh... yeah... everything's fine."

Gwen looked at him inquisitively. After a moment of silence Charlie finally mustered the courage to ask.

"Ok, to be honest I-"

He was cut off by the waitress arriving with their food. She placed their respective dishes in front of them. Gwen smiled as she quietly thanked her.

"You were saying?"

Charlie looked down at his food then back up to her.

"Look, we've been talking for what? Three months now and have gone on six dates. I feel like we really share a lot in common and seem to really get one another. So with that in mind I wanted to see if you'd be interested in taking this relationship to the next level? You know, make it official".

Gwen looked at him somewhat blankly then down at her food. She glanced back up to him before finally opening her mouth.

"You're a really funny guy and definitely nicer than most guys I've dated in the past. I have really enjoyed spending time talking and going out. But I'm just not ready for a serious relationship. I'm too busy ya know? It's not that I don't like you or anything I just don't think I could make it work. I mean we can still hang out and be friends, maybe when I'm in a better place somewhere along the line but until then... no. I know that's not the response you wanted to hear, I hope you understand."

On the outside Charlie seemed unfazed by what she just said, inside however was another story. His mind was racing with numerous thoughts. Thoughts of sadness, of anger, or hopelessness. One question kept making its way to the top of his thoughts: "why would a girl have an account on a dating website when they don't want a boyfriend?!"

After a moment Charlie finally said something: "Sure, yeah I get you. It's not a problem... I figured I'd ask... seemed like the next logical step."

Oblivious to how Charlie really felt Gwen smiled, "I'm glad you understand. We shouldn't dwell on it though, let's eat." She stuck her fork into her plate of pasta.

Charlie returned her smile and did the same.

After holding back his series of emotions and phoning in the rest of the evening Charlie paid the bill and walked with Gwen to the door. He opened it and held it for her as a large gust of wind blew straight into them, it chilled him to the bone. Gwen turned to him and smiled.

"I had a fun evening, we should get together again really soon. I'll text you?"

"Same here and yeah that sounds good."

Gwen perked up and then gave him a hug. "Thanks for dinner, good night!" She let him go and walked off waving.

Charlie returned the wave and headed towards his car.

On his ride home he let loose all his pent up feelings. One second he would slam his fist onto the steering wheel yelling profanities the next mumbling to himself about how he could be so stupid in believing that she was actually interested in a serious relationship. After what seemed like an eternity of driving he finally pulled into his driveway.

Taking no time he undressed into his boxers and crawled into bed more depressed than he could remember. Like a robot he silenced his phone, plugged it into the charger and turned out the light. He laid his head on his pillow starring at the wall.

Slowly he began to murmur to himself: "How the hell did this happen? I just don't get it. We were perfect, we shared almost everything in common, we got along great. So many dates and texts and she's not ready for a serious relationship?! Why waste my time and yours then?!"

His eyes began to water slightly.

"I'm gonna have to do this all over again, months of skimming through accounts and swiping through pictures just to end up in the same place I am now."

He laid in the dark in silence for a long while.

"I just wish it would be easier for me to get a solid relationship. No matter what I do or what I say I always end up here."

Finally sleep overtook him.

His dreams that night were odd, even for him. He was alone in an open field of grass. Looking around there was nothing but grass and hills as far as he could see. As he started walking he spotted a patch of ground lite brighter than the rest. He slowly approached it and cautiously entered. Immediately he felt a lot better.

Suddenly a voice: "This will help."

Charlie spun around just in time to see a naked Gwen extend her index and middle fingers towards him and touch his forehead.

Charlie immediately woke up in his bed with intense stomach pain. It seemed in his sleep he had kicked his comforter and sheets off his bed. He turned on his light and sat up holding his stomach. It felt as if he belly was going to explode.

Charlie let out a few small gasps of pain, "Ah, damn Italian food, I knew I shouldn't have-"

The stomach pain shot out towards his sides. His hips suddenly expanded in a single violent movement while his stomach simultaneously arched in revealing an hour glass figure. His boxer's elastic band was stretched to the limit. Squirming from the pain Charlie fell back onto his bed. He began to see all the hair on his body recede into his skin as his legs began to shrink in length but grow in thickness. His arms, and shoulders started to slim down into a more dainty, feminine figure.

"What's happening!"

He raised up his hand in front of his face in time for him to see them morph into that of a woman's.

"No... No! No! No!"

Charlie began to feel a lifting sensation where his ass touching the bed. The shooting pains were giving way to a slow growing feeling of pleasure. Looking past his girly hands he started to notice his lower torso move a few inches off the bed. Charlie squirmed trying to see what was happening. Moving only increased the pleasure. He finally saw that he now had a plump feminine ass. He turned it again only to see a massive erection bulging out of his boxers.

Charlie starred at it in disbelief. Fixated on both his lower half and the ever increasing feeling of pleasure he barely noticed the tingling sensation on his face. His facial hair began to disappear as his lips plumped out, his nose shrunk and his face became softer and free of blemishes and acne. It wasn't long until the sensation reached his scalp did Charlie take notice. Long brown hair slowly started to crawl out from his head. It grew over his face and onto the bed only to flow off the edge.

Charlie did his best to fight back the pleasure which now seemed almost too much for him.

"No... why is this happening? Why-"

Charlie's voice cracked as his Adam's Apple disappeared from his throat. He tilted his head down trying to find while feeling around his for it. That was when he saw his chest begin to shake. A pulsating feeling overtook his upper half. Two large DD breasts slowly grew outward into his field of view. Each inch increased his pleasure.

It was too much, the blissful pleasure had reached orgasmic levels. Charlie tilted his head to his side as he curled his arms over himself to touch his shoulders. He closed his eyes and bit his lip. His penis squirted semen out as his boxers finally burst off his body.

"Yes... Yes! Yes! Yes!"

With his new feminine voice Charlie let out moans of intense pleasure as his penis and testicles receded into his groin leaving nothing but a wet, tight vagina. The ecstasy Charlie had felt during his, now her, transformation began to die down. Charlie looked down at herself. Her bare tits laying on her chest. She slowly got up and looked over at her nightstand. The alarm clock read 6:57am.

Charlie sat up and reached for her phone. She unplugged it, two text notifications popped up from Gwen.

The first read: "Hey Charlie I'm sorry about earlier, I know it must be hard for you. I just wanted to say I still consider you a really good friend and want to keep our friendship going."

The second, which arrived an hour after, read: "Please say something."

Charlie smiled as she opened up her phone's camera and took a selfie of herself. She quickly looked at it and put it in the conversation and wrote below it: "No problem we can still be friends. BTW thank you, this should really help." She rubbed her new vagina and pressed send.