🌸🌸 My First Time with my Married Neighbor 🌸🌸
(This is based..
🕑 Added 2023-06-18 18:43:34 +0000 UTC
🌸🌸 My First Time with my Married Neighbor 🌸🌸
(This is based on the true story of losing my virginity to the straight daddy who helped usher me into my femininity)
When I started dressing up secretly as a girl, I had no idea how much attention I would start getting. I’m Cassie, I’m 18 years old, I’m thin and small with medium length brown hair and green eyes. I very recently started wearing makeup and dressing androgynously in my day to day life. And in the privacy of my bedroom, started wearing bras and panties and wigs and dipping my toes into what it would be like to be a pretty doll for men. I always had a thing for daddies due to their tough nature and my need for validation from a big strong man.
My neighbor Greg in particular had always caught my attention. He was an older guy, in good shape. I always saw him working outside without a shirt and would occasionally talk to him about whatever was going on in my life. He always seemed interested in what I was saying, didn’t seem to have any aversion to me being a very obviously pre-transition trans girl. He complimented me often about my makeup and would call me pretty and beautiful. I really wanted to tell him about my secret.
I remember one night seeing a suspiciously tall woman walk out of his house. Looking back now, I wonder if she was a trans woman. I always fantasized about being with a straight man. And he was really cute! He was taller and looked like a real man next to me.
I was already picturing myself in lingerie as I sucked his dick and played with his balls. Now I was fantasizing about being his personal slut. My dick was hard and leaking through my panties. This was one of the days where I had the house to myself for a couple hours and could get completely dressed up and walk around the house and not worry about being caught.
I was laying in my bed contemplating my transition from awkward boy to a pretty girl with long hair, done makeup and smooth skin and long nails. Being home alone I was dressed in a black skirt that barely covered my pink panties, a bra, and black thigh highs. I could already imagine what I would look like if I started taking hormones. I knew that I could find the man of my dreams if I were to go all the way. I was willing to go to great lengths to earn that attention.
I even gave herself a girl name to use on the internet, 'Cassie Reef'.
One day my body will match my name.
Just then I heard a knock on the door. I assumed that it was a delivery and rushed over to open it and throw any girl clothes into my hiding spot before anyone else found them.
I was very surprised to see Greg answer the door. I was in total shock. He looked at me with confusion, he didn’t recognize me at first. He said that he was here because some mail of ours had been delivered to his address. I saw the look on his face change from confusion to curiosity when he realized that it was me. ‘Cassie, you look gorgeous, I didn’t know that you dressed like this ’
I gave a nervous laugh and said “yeah I’ve been doing it for a while.“ He tells me that he’s very supportive and that I look great. I can feel the sexual tension in the air as he looks me up and down. I feel so small. I can’t help but to look at the bugle in his pants and then back up at his handsome face. ‘You know I won’t tell anyone about your secret’ he tells me. “That’s good, I’ve really wanted to open up to people, you know you can come inside if you want and I can show u more,” I say.
I needed to compose myself. I couldn’t believe what was happening. He steps inside and his presence is so massive compared to me. ‘I see you as more than a neighbor, but as a good friend’ he says to me.
‘Why don't you take a seat on the couch’, I say.
I walk by slowly swaying my slim little hips. As I’m standing, I feel his hands grab my hips and his erection grind against my ass.
I was surprised at first but then began pushing my ass back onto him.
"Oh Greg! I can feel it! Your cock is so big! Oh fuck you’re making me melt." I barely got out.
"Don't worry, I’ve known about you for a while. It’s obvious that you’re a beautiful girl who still needs a bit more confidence to be yourself. You’re a boy right now but a sexy little slut to me. And I intend on treating you that way! "
I desperately needed to be penetrated by this man.
I looked up at him with wanting eyes. I never knew how good it would feel to be daddy’s.
‘I'll be your good girl, I promise.’
"I like that. I think it's time for some practice.
“We can start off with you giving me head, once you’ve proved that you’re a skilled sissy boy, we can move move on to anal training." He informed me.
"Now why don't you be a good girl, drop down to your knees and show daddy what you can do."
I rubbed my face all over his crotch while purring in pleasure. I can’t believe I could make a real straight man this hard and horny for me.
"Now take it out and start playing with it like a good little slut my kitten." He commanded. His dick bounced out and smacked my face, I had no idea that my neighbor was so big. ‘If only my wife were as beautiful as you’ he said to me.
I placed it in my warm wet mouth and looked up at him for his approval. I was getting all the approval I ever wanted sucking daddy’s fat veiny cock.
I was moaning in desperation to please him.
I was working hard to get him to cum.
I looked up at my new daddy and asked innocently, "did I do good daddy?"
“So tell me, have you had anal sex yet?" He asked.
"No I haven’t. I have a few dildos but none as big as your fat daddycock." I admitted.
"Okay, if you have a butt plug, start wearing it 24/7, your training will go a lot smoother if you stay stretched out!" He advised.
I lifted up my skirt with one hand and pulled my thong to the side with the other to show that I was already wearing one. His mood changed and he became insatiable with my body.
He took hold of it and slowly pulled on it. Once removed, my pussy was on full display.
He pulls my little pink thong down my legs to about mid-thigh. He steps back to admire the view.
I had delicate thin legs and a tiny peach ass. I looked back and saw his large hands grip his strong dick. His whole body looked hard and intimidating. I can’t believe that someone like that could want a cute little flower like me.
He moved close enough to take hold of my hips letting both thumbs caress my soft ass cheeks. Bending over, he took a long slow wet lick up my thigh and kissed my balls and the back of my penis, until he reached my tight little hole and aggressively shoved his tongue inside. I started moaning 'Oh daddy!' He alternated between my juicy pink hole and my shaved smooth balls, I was begging for more.
"Oh daddy that feels so good! Fuck yes turn me into your personal cum slut! Spit on my boypussy daddy, your cock is so big. You're turning me into such a bitch! Please daddy fuck me with your big hard cock. Fuck the boy out of me forever! Make me a real girl please! Make me your real girl!" I begged and pleaded as I shoved my hole onto his invading tongue.
He replaced his tongue with his thumb and applied pressure. His thick digit slipped in working my hole, stretching it, I moaned even more. He removed his thumb and spit on my hole before returning his finger to finish stretching me out.
After a while he slid his other finger in too and really opened me up for what was about to come.
He worked my boycunt till I felt ready and placed the head of his cock against my asspussy, teasing the opening until I couldn't take it anymore.
He pushed in slowly, he fucked me at a slow and steady pace.
I started begging him to go harder.
"Fuck me daddy! Oh god fuck my hole harder daddy! I need it! Take me and destroy my hole! Own it daddy, it's what I need! OH GOD YES JUST LIKE THAT!" I screamed that last part as he started fucking me deeper and harder.
"You're mine, you hear me slut? You’re a girl forever now" He proclaimed and smacked my naked ass twice.
‘Oh fuck! Yes daddy! I'm so yours! Please own me. You’re fucking me so good, don’t ever stop! Yes daddy it's your pussy whenever and wherever! Oh fuck I'm cumming! My little clitty is cumming for you daddy! Please cum in me daddy! I need you to breed me so I'll be even more beautiful!" I submitted.
When he came, I could feel his fat cock pulsing inside my hole. I felt so good as my cum spilled out of my soft little girl dick. After daddy finished filling me full of cum, he pulled out and looked at my stretched out cummy used hole. I was leaking his cum down my leg.
He turns me over and gives me the biggest kiss. ‘Do you want to continue being my sissy slut?’ he asked. “Yes daddy,” I exclaim back.
‘Tomorrow, come over to my place, I’ll get you some new outfits to wear for me’
“Okay ☺️, ily daddy,” I say to him as he holds me in his big arms.
