Unexpected Sissy Transformation
- 2 years ago
- 13
- 0
It’s Just Dinner At The Lakehouse: My Sissy Transformation Part 2 free porn video
The week flew by and before I could blink it was Friday. The blur of a week was mostly spent getting everything I needed to make sure the weekend at the lake house would be a success. I got new clothes, invested in more high-end crossdressing products, and went down a research rabbit hole of sexuality. One dinner party sent me on a downward spiral.
Does this make me gay? Is it fucked up that I kind of liked it? What the fucks wrong with me? Unfortunately, the Internet could only help so much so either I’m going through a sexual identity evolution, or I have a rare form of cancer. Thank you Web MD for the latter. The one thing that was becoming clearer was why I would continue this masquerade.
Sure, this started because I wanted to be a loyal friend, but a new incentive presented itself and has developed into an obsession. I needed to know what was going on with me. I did what I did for my friend, but having fantasies and dreams about it every night since cannot be covered by the loyal friend card.
Also, Rock and I have been… different. A lot of the week was spent planning but not in our usual keep crusader, sidekick way. And worst of all, I didn’t tell him about Dudley.
“Jesus Nick, how many bags are you bringing?”
Rock was struggling to get my luggage in the car. His short and chubby stature made it difficult to lift my bags trunk level. I walked over in my Daisy Duke shorts, my leather boots clinking on the cement each step. I grabbed the bag with one hand and in one motion, swung it into the trunk. An older man across the street who was watering his flowers looked on in astonishment.
“She, uh, works out. That CrossFit stuff.” The old man nodded nicely.
“As I said, I never did this before. Who knows what’s going to happen? I brought extra everything,”
I said, swinging the passenger door closed.
“You’re a real bitch today. If this is what having a girlfriend is like, I’m glad I haven’t had one yet. I think.”
After I checked my make-up in the mirror I flipped the flap up and noticed Rock staring at my long legs.
“Dude… Seriously?”
“I was looking at your new boots!”
“ I got these like three days ago, tried them on, and you didn’t say shit.”
“Christ, did those new clothes come with a fake period or did you pay extra for that?”
“Aw, look at us. Arguing like a fucked up couple. I’m so proud of you,” I said sarcastically.
The rest of the drive felt like old times. As we plotted and planned, songs came on the radio and triggered memories of far simpler times. But as soon as there was even a second of silence, my uninhibited taboo thoughts rose to the surface, flooding my brain and stiffening my restrained cock. I felt the thong tighten on my tucked cock as I adjusted my posture, fidgeting uncomfortably. As we drove up the long dirt path I could make out Rock’s family in the distance, unloading their bags.
The seven-bedroom house sat majestically on the edge of the lake like a scene off of a postcard. I remember being there once as a kid but didn’t appreciate its beauty until now. And of course, there’s was Dudley grinning ear to ear. I stepped out of the car pulling my bunched-up shorts down so that they barely covered my ass. I had a tight belly shirt on that perfectly snuggled my new silicone inserts. More than ever I looked every bit the part, as evident by the jaws that dropped when I walked over to hug Veronica.
“Oh, darling! You look absolutely radiant!" Bitch hated Nick but couldn’t get enough of Melissa.
“Veronica! So happy to be here. This house is breathtaking,” I flushed as we pulled each other in for a hug. The feel of her breasts on my silicone inserts was delightful.
“Oh, it’s our little slice of heaven. Dudley dear, come to say hi to Melissa.”
Sure enough, Dudley was there with a shit-eating grin. His long lanky body looked odd in beach shorts and a tank top. As he approached, he removed his Coke bottle glasses and winked.
“Hey, Melissa. How are you feeling?”
Suddenly, without warning, Dudley shoved me to my knees and grabbed me by the back of my head. In one motion his shorts were on the ground and his long cock was flapping in front of my face. Shocked, I looked up at Veronica who was smiling proudly.
“Go ahead, Dudley dear. Shove that cock down that sissy whore mouth.”
With that, Dudley grabbed his cock and shoved it past my puffy lips wasting no time establishing a rapid rhythm his strong grip moved my mouth forward until his shaft found my throat, and his balls slammed against my chin.
“That’s my big boy,” Veronica glowed.
Astounded by what was happening, I shifted my eyes toward Mr. D.
“You’re a chip off the old block, Dudley. Cum down its throat.” What the fuck is going on here?
I realized the entire family was there watching Dudley face fuck me. Even Grandpa was grinning, rubbing his massive bulge. They started chanting his name.
Dudley, Dudley, Dudley…
“Hey. Melissa. How are you feeling?”
“Huh,” I replied snapping out of the daydream.
“Last we saw you, you were suffering from a migraine,” Mr. D chimed in as he lowered gear from his car’s roof rack.
“Oh. I’m feeling much better, thank you.”
“You look good,” Dudley replied as he looked me up and down. I felt Rock’s hand wrap around my exposed waistline.
“Hey, everyone! It was a long drive so I think Melissa and I will go get settled in.”
After a few quick hugs, Rock was shuttling new through the expansive lake house and up the stairs to our room. The house was immaculately clean with mid-century modern furniture accenting every room. Our room was tucked away toward the back of the house with large floor-to-ceiling windows overlooking an in-ground pool and hot tub. As soon as the door closed, Rock was standing close to looking up into my hollow eyes.
“Dude, are you OK? You're pale as a fucking ghost and you froze out there.”
“I, uh… I don’t know.” Rock was holding my hands, a look of confusion and concern on his chubby face.
“I’m worried about you.” Those words snapped me out of it, and as soon as we both realized what was happening we each let go and took a step backward. A knock at the door made me jump so high I almost knocked my head on the ceiling fan.
“Dinner in five, kids.”
“I… I’m going to go get the rest of our stuff and I’ll meet you downstairs?”
I nodded. “I’m cool, Rock. Really.” He nodded back and left. I glanced over at the long mirror across from the bed and couldn’t recognize it. Sure I always talked a big game, but Melissa was the game. She was tall, beautiful, confident, and obviously desirable. I knew then what I needed to do. I had to lean into that, not pull away. Own it, and work it.
I changed clothes, threw on some pantyhose and a short skirt, exchanged my crop top for a tight black blouse, and slid into some four-inch heels. I walked back to the mirror, smiled, and shifted my waist ever so slightly to get a look at my ass. You got this, Melissa.
Dinner went amazingly well. Once again, Melissa was a huge hit. She was quick-witted, intelligent enough to participate in current event conversations, and she even had some nice zingers for Dudley who was trying to poke her every chance he could. Most importantly, Rock and I had a rhythm back. We were far beyond the awkwardness of our last debut. We were comfortably holding hands, and when I snuggled into his chest with his arm around me during a conversation about how we first met, it came across as completely natural. Mr. D looked on, a proud father who obviously had very few expectations of his older boy and was quite satisfied to see him acting like a real man, with a real woman by her side. Well, maybe not that real.
“Melissa, I can’t begin to express how happy I am that Robert found someone of such a noble profession. As I understand it, registered nurses do a lot more work than doctors,” Mr. D shared proudly.
“It’s true, Ron! A nurse has so many different layers to their job while doctors are pretty narrowed in on specific things.”
“So true, and in your profession Melissa, how much do you charge per hour?”
Dudley’s clever way of reminding me that he thought he knew who I was.
“Oh, we don’t charge by the hour. I mean most of my patients don’t even need an hour worth of service. One in particular last week didn’t even need twenty seconds!” Dudley turned white and dropped his fork to the floor. Don’t try it, my little shit.
“Melissa, it is a blessing to have you with us. In fact, such a blessing that I’d hate to ask you this favor, but I must!” Veronica leaned forward within a whisper's distance as the rest of the dinner party trailed off onto other conversation. I leaned in nervously unsure of what would come my way, fearing the worst. Last time we compared asses, is vagina next on the list?
“It seems our nurse could not make it with us on this trip. And grandpa could use a nurse’s care. Would you please be able to bathe him tonight after dinner?”
“Oh, I’m sure I don’t think that would be a problem. Not something I haven’t done before,” I replied with a nervous giggle.
Mr. D and Rock helped get Grandpa up the stairs to the larger bathroom. Along with various medical issues, Grandpa suffered from dementia and was pretty much a mumbling vegetable. I was relieved, hoping this would be a chance to loosen up and let my guard down. Physically my feet killed and my cock was way past tired of being tucked. Not to mention the mental gymnastics needed to not slip-up around the family. Granted, our prior encounter had Grandpa groping my ass, I’ll take a weak horny old man over Mr.D’s conversations about women’s need to return to a more ‘practical place’ in our society, also known as the kitchen.
I started the tub water and kicked off my heels. I checked myself out in the mirror as Grandpa stood hunched over in the center of the bathroom staring blankly at the tub. Feeling super confident after I killed it during the dinner, I smiled at my reflection and spun around.
“Ok, Grandpa. Let’s do this.”
I unbuttoned his shirt exposing a soft hairy body. I ran my hand down his arm which had faded tattoos, no doubt ink he received well serving overseas. I instantly became sad for him. He was a man that lived a long life and had a million stories that no one will ever hear again. Tossing his shirt to the side, I started undoing his belt, realizing just how tight his pants were around his waist. For easier leverage I got on my knees, feeling the cold tile rush through my body. I unbuttoned his pants and tugged as hard as I could forgetting that his crotch was only an inch from my face. It was then I realized why the pants were so tight, grandpa had a massive cock.
The smell hit me first, a musky stench smacking me in the face. I was suddenly face-to-face with six veiny flaccid inches of eighty-year-old uncut cock. His balls hung low layered with wrinkles from his stretched scrotum. It was a cock that still presented proudly despite its age. In complete awe, I took it in my hand and examined it. I was immediately taken aback by the weight of it. A fleeting thought came, What are you doing Nick? But it quickly faded and lost myself. A raw animal-like craving took over my senses. Every part of me wanted to take him in my mouth. No one will know. So did. I ignored the smell, lifted his heavy shaft, and guided his fat head into my mouth.
The salty taste filled my mouth as I slowly sucked. Then I took more until his head was down my throat. My right hand reached under and began massaging his large balls. Abandoning any common sense or decency thought I had, let go and surrendered to the intense obsession I’d had for the last five days. As if was in a trance, I quickly it was awoken by the feeling of his stiffening cock. Holy fuck he is getting hard!
I jumped up, fear sending shockwaves through my body. Grandpa now he had nine inches of hard steaming cock pointing right at me. took a breath and turned once again finding my reflection in the mirror. Ashamed, I lowered my head and turned on the water. ’ll splash some cold water on my face and this strange nightmare will end. That’s when it happened. It was… one of the most life-altering experiences I’ve ever had. I felt hands wrap around my body and a cock plunge in between my legs.
“What the…no, no, no,” I said panicked.
“Errrrrr,” moaned the old man as he clumsily tried to caress me.
“Grandpa Dolan! Stop, you… you aren’t…”
I could see his face in the mirror. His blank stare was now a passionate rage. His surprising strength kept me pressed up against the porcelain sink, my face now pressed to the mirror. I felt him yank my skirt up and tear my pantyhose exposing my thick ass. Then his fat head poked my ass hole. It poked again. And again.
“Waaaaait!” His fat head finally stretched my asshole and he entered me. The pain was immediate and my body shivered, nerves trembling from my toes to my fingertips. His large hands wrapped around my hips as he began to fuck my ass quick and hard. After a few thrusts with his massive cock, the pain began to subside ever so slightly giving way to an overwhelming pressure inside me.
My dick stiffened as I felt his balls barricade into mine with every push. My ass was open and more accepting of his meaty dick, but the pressure overwhelmed me and I let out a bellowing moan. A moan of enjoyment? I looked up in the mirror and caught his eye. And I whispered, “Fuck me.”
His eyes widened and his rhythm quickened.
“Fuck… me,” I moaned slightly louder. “Fuck me, Grandpa Dolan!”
Smacking sounds echoed in the large bathroom As he slammed his cock into me with relentless force. I braced myself, as I felt his cock stiffen. I knew he was ready, I was too. I backed my ass into him to ensure I was taking it all and that’s when I felt him unload deep inside me. His warm cum, a load that has been waiting for years, filled me. My dick then erupted and shot cum right into the mirror.
My body jerked uncontrollably as I threw my head back, lost my senses, and fell to my knees. I stayed there for a few seconds, shivering, feeling my asshole clench as it tried to shrink back. Grandpa stood there again, gazing at the mirror.
I got myself together, took off my torn pantyhose, and helped Grandpa Dolan into the bath. I spent the next ten minutes bathing him thoroughly well my mind state stuck in some trance. So many thoughts were racing through my mind while my gaping sore ass served as a reminder of what I just did. I tried grandpa off put on his pajamas and walked him to his bedroom where Veronica was waiting.
“Everything OK, sweety?”
“Huh,” I responded in a daze.
“The bath dear. I thought I heard some rustling going on in there.”
“Oh. Well, your father-in-law could sure be a mouthful… HANDFUL, I mean!”
“Ah. Yes, I’ve heard that from quite a few nurses. Melissa, thank you so much you really are a saint.”
“No problem, Veronica.”
I left and turned toward the hall to go back to my room, but couldn’t. Instead, I walked outside to get some air and sat on the old bench swing. I couldn’t wrap my head around what was going on. Dudley taking advantage of me is one thing, but choosing to fuck Grandpa Dolan was sick, twisted, and a whole other ball game. Melissa wasn’t just a hustle anymore. She was becoming something more. She was experiencing, feeling, and taking more mental inventory than I ever thought I would allow.
“Nick?”
I could hear Rock’s whisper in the distance searching for me.
“Here…” We made eye contact and he shuffled over quickly and sat on the bench with me.
“Dude, you look terrible. Are you… crying?”
“Rock, I… this is...” I couldn’t string a sentence together.
“Nick, what’s going on?” His sincere look of concern was almost encouraging. This is the one person on this planet I knew I could trust.
“A lot is going on right now, Rock. I almost don’t know where to start.” He put his hand on my leg and the warmth of his touch was comforting.
“That’s it! We are done. We’re leaving tonight and you don’t have to do this anymore. This was fucked up of me to ask in the first place and it’s gone way too far.”
“No. It’s OK. This isn’t the problem,” I said tugging on my clothes and wig. "It’s way beyond this, dude.”
His big green eyes looked into mine, cloudy with mascara, running down my face.
“Nick, You’re my best friend. I don’t know what’s going on, but I can’t see you like this.”
“Stop,” I interrupted my voice shaking. I place my hand on top of his. Our eyes locked.
“Call me Melissa…”
In that moment everything froze. We both leaned in keeping our eyes locked, and when our lips met, our tongues entangled without hesitation. I felt his hand on the side of my cheek and instinctively reached up and put my hand behind his head bringing him in deeper. Instantly I was calmed, a rushing sense of thrill mixed with familiarity and safety. As we pulled away from each other we maintained eye contact and both said the same exact thing.
Fuck…
Mila
- 01.12.2022
- 11
- 0
- Category:
- Crossdressing
The Sissy Diaries 2 My Total Transformation
- 4 years ago
- 8
- 0
Sissy Stepson 10 Stepmother s Sissy
- 3 years ago
- 30
- 0
