Unexpected Sissy Transformation
- 3 years ago
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It’s Just Dinner: My Sissy Transformation free porn video
I bet you're wondering how I got here. It was only six months ago that I was your normal American guy living every bit of his bachelor life to the fullest. Good job, good friends, good looking...not a worry in the world. But now here I am, standing in front of a mirror wearing a wedding dress trying to figure a way out of this. Nope, that wasn't a typo. I said wedding dress. Hmm, my body is better suited for mermaid style over ballroom. Ugh, see that's the stupid shit that I’ve been saying for the past six months, living in this distorted fucking reality. Let me start from the beginning, and maybe you could help me figure a way out of this shit.
Six months ago my buddy Rock and I were slouched on our beat-up couch playing video games and smoking some weed. You know, a typical Saturday for two best buddies out on their living the good life. I’ve known Rock since I saw him getting his butt kicked on my way home from school in second grade. I tried to help, which promptly led to me getting my butt kicked and we’ve been joined at the hip ever since. His real name is Robert, but people call him rock because he’s not the sharpest tool. He’s short, chubby, not great with the ladies but very funny and likable which always made him the perfect wingman. Still, he’s a loyal friend and one of the best dudes I ever met, even if I always kick his ass in video games.
“Fucker! How do you do that?!”
“As I tell ya Rock, natural talent can’t be taught.” I took a long bong hit to relish my victory and passed it over to Rock who quickly declined.
“What’s with you? You’re losing worse than you usually do and now you’re not even smoking. Known you too long buddy, somethings up.” He shuffled uncomfortably in his seat before he stood up and started pacing the room.
“Okay. You know how tonight I have that stupid dinner with my family?”
“Oh ya. How’s good ole Mr. D? Been years since I saw your dad. And your super cute mom!”
“Bite me, asshole,” he said fighting back laughter. “Seriously. Well, I’ve kind of been telling them that I have a girlfriend for the last couple of months. I’ve been dodging their requests but now I have to deliver tomorrow.”
“That’s it? No problem buddy, I’ll scroll through my numbers and find a prime girl for you.”
“I already considered that. I even considered buying a… You know…?
“A…what? New hair trimmer,” I said sarcastically.
“No, Nick! A lady of the night.”
“Christ, what is this 1950? A hooker! That’s a good idea too.”
“Jesus, don’t say it like that. Yeah well, both are out. I told them I’ve been with this girl for months Nick. Whoever the girl is, needs to know about me. You know my family with the questions and stories and shit like that.”
“Ah, I get it. Quite the pickle you’re in pal.” I laughed as I pulled another long hit from the bong. “We’ll just need to figure out how to advance science a few decades ahead, take my brain, and put it in some chick’s body. Then we are golden!” Rock laughed and then froze suddenly.
“That’s it.”
“What’s it?”
“You’ll be my date!” I began laughing uncontrollably.
“No, no, hear me out. Remember last Halloween when you went to that party as a girl?”
“Excuse me sir, not a girl… I was a prostitute, maybe you would call me lady of the night.”
“Oh, whatever! The point is, nobody knew it was you, and you had to put on a different costume because you kept getting hit on by dudes.”
“Don’t remind me! A real burden being blessed with this perfect ass.” I replied with a laugh as I pull one more hit.
“Dude, I’m serious. You could trick my family. And it’s just for one night. It’s just dinner!
“You’re serious aren’t you? This has the terrible plot of every bad comedy made in the last decade. No way this works.”
“Nick, look at me. I’ve never got a hot girl in my life, so you showing up makes sense.”
“I’m hurt!”
“You know what I mean! And nobody knows me like you. You’ll be able to dodge my military dad‘s interrogation tactics.”
At this point, I thought Rock lost his fucking mind. Okay, I do make a very passable chick. I’ll admit that, but doing that at a family dinner is a way different ball game. I was about to say no, but I had a flashback to the day when I was walking home from school. I’ve always looked out for him, and I’ve always had his back.
“Okay, you little turd. I’m in, but this time only. It’s just dinner right?”
“Right!”
Later...
“Are you almost ready? It’s six o’clock.”
“Seriously? I’m doing this for you and you’re going to rush me,” I replied frustrated from the other side of the bathroom door.
“Sorry, I’m just nervous.”
Struggling a bit, I finally yanked the super tight cocktail dress past my hips. To say I had second thoughts while adjusting my tights is an understatement. I had seventh, eighth thoughts. By the time I got done with my makeup, I was ready to back out.
“Listen Rock, I just don’t know.” And that’s the moment I knew I had to go through with it. Looking into those big green eyes, just as sad as the day he was getting pummeled by a group of assholes.
“You…um… you look… like a prostitute,” he said.
“Told you!”
“No, no! You look great. Not that I’m checking you out… just… passable.”
“Well, thanks. The wig itches and these heels kill but it’ll be over soon. Remember, I’m going to pretend I have a headache half-way in so we can bounce early.”
“Got it. I have notes here. Um, your name is Melissa but I call you Missy. We met in college and reconnected at a reunion and we’ve been happily dating for the past four months.”
“Nailed it.”
That’s when I noticed Rock was checking me out. I wanted to tease the loser but I felt bad. Poor guy can’t get a date and despite his tall tales of women, he meets I don’t think he’s even touched a girl. Now he’s resorted to this. I also couldn’t blame the guy. I looked damn hot.
“Well, let’s go, Missy.”
As we left the apartment our first big test was no more than ten feet away. A group of guys who live in the same building we’re hanging out in front of their cars as we strolled by. I felt their eyes on me instantly and I tried not to make eye contact, which was fucking impossible. It was silent as we crossed in front of them. All I could hear were my heels hitting the pavement.
“Yo, Robby!”
Fuck, we didn’t even make it ten feet before getting busted. Never going to live this one down.
“Nice one!”
The morons fell for it. And those were guys that saw me every day. A sense of relief flushed over Rock as he smiled, and nodded back before opening the car door for me. Test one passed, and I was a ‘nice one’.
You would think it would’ve been an awkward car ride but not us. Rock and I pulled off jokes and capers our whole life and we were locked in. It was like two Navy Seals on a stealth mission. We game-planned and talked about his family. A military dad strict as can be, a hot Betty Crocker mom (okay I added the hot part). A little annoying brother who I remember kicking around years ago, and a senile grandfather. Bases covered.
We approached the door and I instantly remembered everything about the house despite it being a few years. I was here every Saturday growing up and his family was pretty much an extension of my family. Right before the door opened rock grabbed and held my hand. Eek, totally forgot we would have to touch each other! The door swung open in there they were, Mr. D and Mrs. D as if they were cut straight out of a fucking Martha Stewart magazine. Mr. D, or Ron, is a tall man, but with my heels, we were almost eye level. His wife, Veronica, is a former beauty pageant contestant with a perfect smile and slim build. It’s a struggle to wonder where the hell Rock came from.
“Welcome! Oh, Robby, sweety it’s so good to see you,” Veronica exclaimed as she hugged Rock tight. And this must be Melissa! Wow. You are stunning.” Veronica pulled me in tight for a hug which feels very different in this get-up. I felt her ample breasts press into my fake silicone boobs as she planted a big kiss right at the corner of my mouth. A huge difference from when she would disregard me and call me the “Bad Influence“.
“Hello, dad…umm… sir."
“Robert. Good to have you. Melissa…”
A massive cold front from good ole Ron! I could feel his eyes burning through me. That military background being put to use. He was taking it all in and investigating me before I even said a word. There’s no way this is going to work!
“Veronica… Ron, thank you so much for having me over to your beautiful home. Robby has told me so much about you and it’s a joy to meet the family who raised my amazing guy.”
Damn, I should’ve won an Oscar.
“Well aren’t you the sweetest thing. Get on in here, dinner is almost ready!”
The house was pretty much as I remembered it. We walked into a large foyer plastered with family photos. Most of them were of Rock and his little brother, Dudley. Of course, there was none of his childhood best friend. Unfortunately, the Dolans never quite warmed up to me. When that little shit Dudley came in the room it was then I noticed Rock’s sweaty hand clinging to mine for dear life. You see his mom is sweet, but she was an airhead, his father couldn’t care any less, and his grandfather was a vegetable. That little pube Dudley was the hurdle. I put my other hand on Rocks’ back and rubbed it gently.
“Dude, relax,” I whispered. He nodded and took a deep breath.
“Melissa, this is Robbie‘s little brother Dudley.” He still had that menacing smirk just like he had as a little squirt before we kicked his butt.
“Nice to meet you, Dudley.”
“Charmed.” He replied with sarcasm as he looked me up and down.
“Guys? Do you think you’re fooling me?” I could feel Rock stiffen with fear. Leave it to Dudley to see right through this asinine scam.
“Uh…what… what are you talking about loser?”
“I see exactly what’s going on here.”
That’s it, busted. I started feeling a wave of relief. As embarrassing as this is at least we can end the charade and I could untuck my dick. So uncomfortable, no clue how trannys do this all day.
“There is no way you got a chick this hot. You’re paying for it.”
“Dudley, how dare you! Melissa, I am so sorry. Why don’t the men get settled around the table and you can come to help me in the kitchen, dear.”
“Not a problem. I guess I’ll take that as a compliment,” I replied as Dudley winked at me. Gross!
I followed Veronica into the kitchen where she had a gorgeous bread ready to go. I wanted to grab the turkey leg and shove it in my mouth, but have to act like a lady and all that bullshit. Veronica was straight out of a home catalog. Perfect body, with the housewife dress, short blond hair, and blue eyes. We started plating the food as Veronica went on and on about how great Robby is.
“I knew eventually he would find the right girl. And you were friends first you say?”
“Yep, I guess you could say I was right under his nose the whole time.”
“How wonderful! I’m very sorry about little Dudley.”
“It’s ok, as a beautiful woman such as yourself, I’m sure you know we get used to that sort of thing.” Oops, don’t hit on her dummy!
“Oh! How sweet. But I will admit, he is right. You are striking.”
“Thank you, ma’am.”
“My pleasure, but I have to ask. Sorry if this is being a bit forward but ‘girl talk’ and all, how do you get your ass so shapely and tight?”
“Oh, I uh…”
“May I?” Before I could even reply her hands were on my ass.
“Wow, so strong but also soft! Enjoy it while you can honey. Mine is like a deflating balloon after a birthday. Feel!”
She grabbed my hands and pulled them around her waist until I was cupping both cheeks.
“See?”
“I, oh, yes. Yes, you know the misconception is squats are good for buttocks development but it’s all about lines.” The only reason I knew that was because I stumbled across some hot girl's YouTube video.
“Yes! I was telling my friend Barbara that very same thing,” she exclaimed as she released me. “Let’s get this food out, can you grab that plate for grandpa?”
I grabbed the food and headed for the dining room hoping this massive boner wouldn’t pop my tuck tape! I walked around the table and over to grandpa who was sitting and smiling, his mind seemingly wandering off into the distance. When I lowered the plate in front of him I felt his cold wrinkly hand run up my leg, under my dress, and grab a handful of my ass. Instantly I froze and looked around to see if anyone saw, but they were far too busy with their trivial conversation to notice him massaging my ass. I looked down and of course, right there was a big fat hard-on under his cheap khakis. I rushed away just as his fingertip started poking my asshole and sat down next to Rock.
“Dude, your grandfather just groped the shit out of me.”
“Don’t worry, he does that to all his nurses. He has no clue what’s going on.”
“Oh, gee! Thanks, that makes me feel so much better.” Dinner went surprisingly well. It was your typical dinner conversation about current events, Mr.D’s work, Dudley’s school, and a lot about Rock and Melissa. Melissa was an instant hit, and everyone liked her/me. The best part is that we were in the homestretch, and it was time for my sudden “headache”.
“Oh, Melissa hun. Do you need anything? We have Motrin upstairs,” Mrs.D said with a sympathetic smile.
“That’s okay, mom, I think we’re just gonna call it a night and I’ll bring Missy home.”
“Nonsense, we didn’t have your mother's cake yet.” Mr. D’s military background rarely let him stray from a well-organized plan. “Besides, there’s something I want to talk to you about. Dudley will show Melissa to the upstairs bathroom where we have some medicine, mother will clear the table, and you and I can step outside." I grabbed Rocks leg under the table and squeezed.
“Er… Uh… yes, sir.” Shit!
I followed that little shit Dudley up to the bathroom trying to think of a way out of this. Instead of taking me to the bathroom, Dudley took me into his room. What used to be a room for a little boy was now decorated with video game posters, pictures of models, and food remnants of all-night gaming binges. Nerd.
“So, this doesn’t look like a bathroom.”
“The gig is up. I know exactly what’s going on here,” he said with an evil smirk.
“I , Uh…”
“Save it. I may be young but you didn’t think I was going to figure it out?"
Looking down at the floor defeated, I slowly raised my hand to take the wig off. At least now I can get out of this outfit.
“I knew you were a prostitute.”
Huh, I stopped.
Dudley reached into his pocket and pulled out the small cheat sheet of notes Rock had about the fake relationship and Melissa’s backstory.
“I knew there was no way he could get someone hot as you. And this proves it.”
“Listen, you little..”
“Shut it, whore! This is what we’re going to do, and listen close because we don’t have a lot of time. I’ll keep quiet, but you’re going to do something for me. You’re going to suck my cock.”
“You cannot fucking be serious! No way!”
“Do it or a giant shit storm happens downstairs in five minutes when I tell everyone the truth!”
I was standing there completely shocked as he was already undoing his pants feverishly. I was trying to think quickly but I couldn’t focus. All I could think about was Rock’s face when his family found out, and even worse if they found out it was me! Any chance of coming up with a quick out immediately vanished when Dudley dropped his draws and revealed a surprisingly huge hard-on.
“Er…no way, you’re just a high school brat. I’m not going to Jail.”
“I may look young but I’m eighteen, and last I checked eighteen is the age of legal consent in this state, bitch.”
I tried thinking of what to do, but his surprisingly huge cock was pointing at me like a rifle. Instantly it was like I was transported out of my body, watching it like a terrible porn scene. I walked over and I got on my knees. With his head right at the tip of my lips, I opened up, closed my eyes, and took his cock in my mouth. Immediately, I felt him quiver as I quickly sucked hoping the faster I went the quicker it would go. The musty smell of his balls filled my nostrils as his cock found the back of my throat. I felt his hands grab the back of my head and the little shit began to fuck my face, his long shaft gliding in and out as his mushroom head forced its way down my throat.
He popped his cock out of my mouth, lifted it with his hands, and presented me with his balls which I assumed he wanted me to lick. Completely humiliated I tried to ignore the stink of his balls as I took them in my mouth rolling them around. He moaned in pleasure as I fought back the feeling of wanting to throw up. He shoved his cock back in my mouth and fucked my face even harder. I could feel the rhythm change and his body tense up as he shot a huge load down my throat holding my head and not letting me move. The warm come filled my mouth as I gagged. Come was oozing out of the side of my mouth back onto his big dick as I finally pulled away. Dudley plopped down on his bed, exhausted and with a big smile. I fell back sitting on his carpet struggling to get his entire load down my throat.
“You are a professional,” he said with a satisfied sigh.
I shot up and scrambled toward the bathroom. I looked at myself in the mirror and did what I could to fix my makeup and keep myself from throwing up. I looked like a porn star I've just finished sucking off of football. I hurry downstairs where I found Rock and his father just coming in from the deck.
“Oh, Melissa, you don’t look so good. You’re pale as a ghost and quite sweaty.”
“I’m sorry, Veronica but I’m not well. I need to go.“
“Oh, funny. Let’s get you home,” Rock said nervously.
“Yes, best to go home. We’ll see you next weekend,” Mr.D said.
“Next weekend!”
As soon as the car started and we pulled out of the driveway I ripped into Rock.
“Are you fucking serious? You told him we would go to your lake house for the weekend!”
“Melissa… I mean… Umm…You have to understand. My father has hated me my entire life. When we talked outside he said how proud he was of me that I’m getting serious with such a nice woman.”
“Do I need to remind you fuck-o, I’m not a nice woman? I’m your best friend since second grade!”
“Listen, he wants to take us up there because he wants to give us the lake house!”
“Wait, what?”
“He wants to give me the lake-house and he wants us to all be there when he does it. That house is his pride and joy!”
“Wow, that must mean a lot to you.”
“Everything.”
“Well count me out. This is fucking ridiculous. I’m done.”
“What happened back there? Everything was going fine. You looked like you were enjoying getting over on them.”
“Just stop. I said I’m done. Tell them Melissa dumped your fat ass.”
We didn't talk for the rest of the ride. When we got back to our apartment he went straight to his bedroom, and I went to the bathroom. I looked at myself in the mirror at some version of a trashy college coed. My body still looking tight in the cocktail dress but my face a complete mess. Reflecting on the night, I was horrified, but not for the reasons you would think. I was groped by an old man, fondled by my best friend's mother, and face-fucked by Dudley. I could still feel those old weathered fingers poking my asshole. I could smell Dudleys balls and still feel the warmth of his cum down my throat. What horrified me was simply, that I didn’t hate it. And that’s when I noticed my dick getting hard. Completely confused, I reached for my phone. Normally during these times, I would go to my best friend, but now even that seemed impossible. I sent Rock a text and confirmed I would go.
He responded with texts of praise and thanks, but I didn’t have the energy. I crawled into bed appreciating the silence. And as I relaxed, I reached down under my sheet and reflected a little more on the night.
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