Crossdressed in public
- 3 years ago
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Crossdressed In Best Friend’s Mom’s Clothes 7 free porn video
I got out of bed and went to the kitchen to make a cup of coffee. And as I did that, I saw a note on the kitchen table...
Good Morning, Darling. Mommy had to go early this morning. I wanted to let you know that you don't need to take those drops anymore, for now. And your father called. He asked if he could talk to you. But you were asleep. Please call him back. Cya soon. Kisses from mom.
I picked up the phone and rang him up, and sat down with my coffee.
“Hello, this is Steve!”
“Hi Steve, it’s Brian!”
“Hello Brian. Long time since I heard from you! Are you doing ok? You sound a bit funny!?”
I coughed and spook with a deeper voice. “Yeah sure...I'm doing just fine. Just a little cold. Thanks for asking though! How are you holding up?”
“You know, busy as always...too much work! But it's all good! You know I don't have to share my money anymore. Get it? He-he!”
I didn't know if that was sad or he meant it. “He-he, yeah. Living the life, huh Steve?”
“Sure do, son. Well speaking of money, I got some for you. Or rather said, it is from your mom and me!”
Why would they give me money? For the lack of not being there?
“Oh really? Well I got something I wanna tell you! So it's a good time to meet and talk about it!”
“What’s up? Is everything ok?”
“Yes, dad...everything is just fine. But I wanna tell you in person, than over the phone!”
“Well you can come anytime, I’ve got the day of work, so I’ll be home!”
“Let me finish my coffee and I’ll be over in an hour or so. Sounds good?”
“Sure do, son. Cya then!”
And I hung up the phone. I wanted to tell him about myself, and that I pretty much was Caroline most of the time now. And that was one of the reasons I wanted to let Peter know too! I didn't want to hide the fact that I’m mostly a girl now.
After I finished my coffee, I took a quick shower and found something to wear. I found a red top and a little black cardigan, to put over my top. It really only covered my arms, so my hard nipples were showing through the red top. Some black jeans I had cut up into very short shorts. And then I found some red opaque pantyhose. No panties or bra. Just light and easy! Plus, summer time was just around the corner, and it was a nice weather outside. I did my Gothy makeup with a hint of red eyeshadow on top off the black, a nice dark red lipstick, and put my glasses on. I had gathered some different coloured ones and picked out some red ones. At last, I put my blonde wig on, and adjusted it to perfection. Checking myself in the mirror, and I looked hot as always, but I was getting a bit tired of the wig. And now that my own hair was getting longer, I thought about using my own black hair. It was a little longer than shoulder length. It didn't look that nice, but for now I kept my blonde wig on. I found my black leather jacket, and some black ballerinas. I looked at myself in the mirror, and everything was perfect. My god, I loved to dress up as a smoking hot girl. Nothing better than to be Caroline! I sprayed myself with perfume and off I went.
I arrived at my stepdad’s apartment and took the elevator up to the 4th floor. I stood outside and was trying to get the courage to ring the doorbell. But then from behind me, I heard a voice saying. “Hello, can I help you Miss?”
I jumped scared and let out a little scream.
He laughed, “Ha-ha. Sorry Miss, I didn't mean to scare you!”
I turned around and saw Steve, with mail in his hands. But when he saw me, his eyes looked me up and down, and finished with a smile. I of course panicked again and lied. “It’s fine. I think I’ve got the wrong address. Sorry to bother you. I'll just be on my way. Have a nice day!”
“A fine girl like yourself couldn't bother me! I was waiting for my son, and he should have been here by now! I don't think he’s coming by today. So why don't you come inside for a cup of coffee as a sorry for scaring you?”
‘Pull yourself together and just tell him that you're Caroline!’ But no, I just had to say “He-he...I could use a coffee. Thanks, I’ll take the offer!” ‘He is going to be so disappointed when he knows it is me!’
He unlocked the door and he let me in first. “I’m Steve, by the way!”
I took my jacket off and hung it up. “I’m Caroline. Nice to meet you, Steve!” ‘Oh stupid Caroline...just tell him that it is you!’
I was about to take my ballerinas off, but he stopped me. “You don't have to take them off. It's pretty dirty anyway. I need to vacuum soon!”
I stepped inside and saw his apartment for the first time. It wasn't dirty at all, and it all looked very nice and modern. With nice exposed brick walls and beams. Huge window side and a nice big balcony with an amazing view over the city. And a new kitchen with a vintage look. I loved this place. Maybe I should have moved in with my stepdad? He was in the kitchen getting the coffee ready.
“So who you came to visit?”
without hesitation I told him some bullshit story. “My grandpa. But it must be on the fifth floor and not the fourth! He just moved in and his getting old!”
“Ah, I see. The floors look a lot alike and no proper signing of the door numbers. Milk and sugar?”
The more I lived as Caroline, I found many things different between Brian and Caroline. One of them was that Caroline liked milk in her coffee, and Brian liked it black.
“No sugar. But I would like some milk thanks!”
He opened the fridge, but he didn't have milk. “I seem to have run out of milk. No worries, there is a 7/11 just a block away. Wait here, I’ll be right back!”
“That's very kind of you, but you don't have to...I'll drink it black!”
“Stop it. It won't take long 10 minutes, and I’m back!” and off he went.
I thought that my stepdad looked more muscular. Had he been training or was it just my mind playing tricks? When I lived at home, he just seemed so nerdy, but now he looked more like a real man. He smelled good too. ‘Fuck...stop thinking things like that. He raised you pretty much from when you were 5 years old!’
I walked around the apartment. Huge living room with the kitchen, and 3 other doors. One door let to a nice bathroom with big hot tub. The other room was like an office with a lot of computer parts laying around. And lastly, his bedroom. I gently walked inside, and there was a person laying under the blankets of the huge king-size bed. It really scared me at first, but at a closer look, I saw it was one of those real-size fucking dolls! I always wanted one for myself, but that kind of money I could only dream of having. Those dolls were so expensive and I couldn't wrap my mind around that my stepdad had one of those. I got a closer look and pulled the blanket away. It had black long hair and a pretty face. It was just lying on the bed in a black corset with a garter belt, black stockings and black lace panties on. Those breasts could as well had been mine because they looked like the same size as mine. It was really amazing...but it had a bulge in her panties! At first I thought it maybe was a dildo. Then I pulled the panties aside, and to my surprise, the doll had a cock! My mind was blown. ‘Was my dad into chicks with dicks?’ I looked closer and she also had a pussy and asshole. I couldn't believe that my dad had a ‘fucking doll’ with a cock! ‘Did he know something about me? Why would he? Maybe he just liked that? Fuck, I wish I’d never seen this!’
I covered the doll and put the blanket back as before. I closed the door to his bedroom, sat down in his sofa, and all kinds of thoughts just went through my head of the doll I’d just seen. 3 minutes later, my stepdad was back with milk.
~*~*~*~*~*~*~*~*~*~
“Hi. Now let's get that coffee!”
“Thanks Steve. You’re too kind!”
He came and sat down in the sofa and placed the coffee on the table. I took a sip.
“Mmmm...that is really good coffee!”
“Should be. The beans are from Columbia. Rich in taste and smell!” He smiled at me. His eyes was staring at my hard nipples, almost poking through my red top. I should have put a bra on anyway. I blushed, and couldn't believe that my stepdad was checking me out like that.
“So you have a son?”
I don't know why, but Steve looked more buff and acting more like a man than I had seen before. I got kinda turned on by him.
“Yes. But it is my stepson. His mom left me for another man. That fucking whore!”
I didn't see that coming, him calling my mom a whore! And I just kept on being Caroline, not to make him suspect me. “Really? How could she leave a fine man like you?”
He laughed “Ha-ha. Thanks! But now I’m free of her, I kinda feel a lot better with myself!”
I glanced down at his black sweatpants and saw a huge bulge between his legs. Wow, Steve had a huge one! Mmmm.
‘No...stop it, Caroline...it is your stepdad!’
Without even realizing it, I crossed my red opaque pantyhose leg over my other leg. His eyes wandered all over my thighs and down at my feet. I was sitting there dangling my leg and was heel-popping with my ballerina shoe. I even saw him lick his lips a little. I then came to realize that I was full-on flirting with Steve. My own stepdad! And when I tried to stop myself, I accidently dropped my shoe, and my red pantyhose foot was showing. My face blushed, but then he picked up my shoe.
“Wow...that is one pretty foot. Let me help you!”
Steve gently grabbed my ankle and glided his finger over my hosed foot and very slowly put my ballerina shoe back on my foot. I smiled at him with a flirty look.
‘Why am I doing this? Pull yourself together!’ But I guess my mind wanted something else. So I dropped my shoe again. “Oops...clumsy me!” I wiggled and pointed my red hosed foot in his sight and he got a smirky look on his face.
“Yeah, clumsy you. Mmmm!” Then he adjusted his cock in his sweatpants, and I played so innocent.
“I'm so sorry...I didn't mean to turn you on like that! He-he!”
“Oh you bad girl. I can't believe this is happening! I love that I can see your black nail polish through those pretty red pantyhose. Mmmm, yes!”
I couldn't believe that my own stepdad said that about my feet! I popped my other shoe off and placed my feet by his stiff cock outside his sweatpants. His eyes got big and just stared at my red hosed feet. And I found his cock, and it was big one too! I started grinding my feet up and down his big cock, feeling it hard. Real hard! Mmmm!
“Oh fuck, that is so hot! Ahhh! My wife never did anything like this! Wow! Mmmmm...such pretty pantyhose feet!”
I wanted to see his big cock so badly! I wanted to feel it between my toes! I tried to stay as cool as I could, but my tiny dick got so hard too! Good thing it was tucked away and up in my tight fitting shorts.
“Shouldn't you pull that lovely cock out, Steve?”
Without a second to spare, he pulled out a real nice long thick cock. And I was surprised that Steve had such a beautiful cock - and he was even all shaven smooth.
“Wow. Girls most love that big cock?!”
“He-he...Well to be honest, I haven't been with anyone since my wife left me!”
I had no clue, but then again that maybe explains the sexdoll! My pantyhose feet gently grabbed a hold of his cock and started pushing up and down.
It felt amazing between my hosed toes. Even pre-cum oozed out of it and smeared in my pantyhose. Mmmm yess. That feeling that I was pleasing a man with my pantyhose feet was the best! His cock was so stiff, and I know I had small girl’s feet, but his cock was as big as my feet! He laid his head back in sheer pleasure, and I just kept going and going, grinding that pretty cock with my red pantyhose feet. My head was blowing inside with the thought of me doing this to Steve, and I wanted to taste his huge cock in my mouth! And as I saw more pre-cum come out, I thought ‘it is now or never’. I stood up and got in front of him, pulled my top down under my breasts, revealing my breasts and my rock hard nipples for him to see. His jaw dropped and he just stared. I got on my knees, Put his cock in between my small firm titties, and pushed with my hands against them, to grind my tits up and down his cock. And of course, my mouth downward to his big nice dick head filled with pre-cum, and stuck my tongue out. So everytime I pushed down on his cock, his nicely shaped mushroom head filled with pre-cum got smeared on my tongue. Fuck yesss! The taste was amazing, and my body started twitching a bit. He was moaning a lot.
“Fuck...You’re so beautiful...Ahhh Mmmm...I love your fucking tits...AHH!”
I just kept going up and down and tried to get every last drop of his pre-cum in me. Shit, he turned me on so much with his words...I had to have his big cock in my mouth! I let go with my tits and just opened my mouth widely and just swallowed his whole cock down all the way. I felt his mushroom head way past my throat, and I fucking loved it! I held it there and gagged on it, making it all wet of my saliva. I sucked it so hard and good. And as I would come up for air, I used both my hands jerking his pretty cock. Tears were running down my eyes and felt my mascara running, but I loved every second sucking my stepdad off.
“HOLY FUCK...AHHH!! Mmmmm Fuck...Yes! Suck it good! Uhhh, baby!”
He pushed my head back onto his cock and held me down and I was full on gagging on it. I felt my tiny dick getting harder and pushed my red pantyhose so hard that it popped out past my shorts. He grabbed a hold of my hair and pulled me off his cock. He got a bit wild and held a good grip on me as he pulled my head to one side. “You are a fucking little cocksucking whore, aren't you?”
I nodded eagerly. I shook my head and he slapped me on my cheek. Not hard, but in the good kinda a way.
“Answer me, little slut!”
I nodded again. “Yes I am! I love sucking cock. And especially yours, Steve. Mmmm!”
And he shook my head again - but then my blonde wig fell off. My black shoulder-length hair was now exposed. He froze and I froze. He looked at me real good. I was so fucking busted! I was ready to lay down and die, but his face got a huge smile on.
“Holy shit...You just became 10 times hotter! Man, how is that possible? Suck me till I cum in that little slut mouth of yours!”
He threw the wig over the side of the sofa and grabbed my real hair instead and pushed me down over his big tasty cock. He didn't know anything - Must have been all the makeup, my glasses and my long hair! I was in heaven. So I gave it all I had - and I craved his cock! He held real good on my head and fucked my mouth so hard my tits were bouncing. Mmmm, I felt beautiful and loved every bit of being a girl. I loved sucking my stepdad’s cock. In fact, it felt so good that I didn't even feel that I cummed on myself and my red pantyhose. I was enjoying every stroke his cock hit me with, deep down my throat. He went on for 5 minutes - and then he couldn't hold it anymore. He didn't even moan, more like grunting noises - and a huge load of cum squirted out of his cock and he kept on fucking my mouth as he cummed. So much inside of my mouth - I tasted his delicious cum from deep down my throat and all over my tongue and even my lips! Holy fuck, I never sucked any cock like that before!
He gently let go of my head. “Shit...I’m sorry, Caroline...I got carried away! Hope you’re ok?”
I stood up and tucked my tits away as I gave him a big smile. “I'm all good, Steve! I love sucking cock, so don't worry about it!”
He looked down at my red pantyhose thighs and he saw huge wet stains on both of my thighs. My tiny dick had crawled away and inside the shorts again. “Wow...Ehmm, I see you came too? You really do love sucking cock! Dirty girl, he-he!”
I looked down at myself and saw the huge stains my tiny dick had made on my pretty red pantyhose - and my face turned red instantly. “Oh no...I didn't even feel that. I'm so embarrassed!”
“Come on, don’t be. Glad you enjoyed yourself too! Don't worry about that...I think I’ve got some of my wife’s old clothes...I'll be right back!” He went into his bedroom and came back very quickly, and had something in his hand. “Here you go. The bathroom is over there!” He pointed at it.
“Thanks!”
I walked into the bathroom and locked the door. I looked at the clothes he’d given me. It was a red mini-skirt with black little dots on, and a pair of black opaque pantyhose, still some of my favourite kind. I took my cum-stained shorts and pantyhose off and threw them on the ground. I cleaned myself with a bit a water and dried myself. I pulled those black pantyhose on, and on top, the red mini-skirt. It looked very good with my top and my cardigan, but I knew this was not my mother clothes! She almost never wore pantyhose and definitely no mini-skirt! Nope, this must have been clothes that were meant for his ‘fucking doll’. Good thing I was close to the same size, though they fit a bit snugly. I picked up my dirty stained hose and shorts and walked out into the living room. And as he saw me, he stared me up and down.
“Wow...Really beautiful, Caroline!”
I blushed “Thanks Steve. And thanks for letting me borrow this!”
“Ah, don't mention it. And just keep it. The least I can do after what you gave me!” And he winked at me.
“He-he! Where is your trash can?”
“Under the sink! Just one more thing!”
I went over and threw my cummed hose and shorts out. “What's that?”
He smiled at me. “You look way better without your blonde wig. So I would leave out the wig in the future!”
I was flattered that he liked me without my blonde wig. It just confirmed that I didn't need it anymore. But I never thought the idea would come from my stepdad!
“I appreciate your honesty...and I’ll for sure think about it! I really need to go now!”
“Ok, thanks again, you sexy lady. He-he!”
I walked out of the apartment and took the elevator down. I never ever in my life had any thoughts about my stepdad like that before. But I’ve never seen him as a real man like that! He had gotten more muscular and was more ‘man’ than ever - and that turned me on! I felt so lucky to have tasted his delicious cock. But I should have told him everything, and was sure he was gonna find out when he pulled my wig off. But that showed me even more that I looked like a girl than ever before. From that day, I decided to use my own long black hair.
~*~*~*~*~*~*~*~*~*~
I reached home and saw Margret's car outside.
“Hello mom!” I walked into the living room where I found her asleep on the sofa. She had on a blue skirt with white 40 denier pantyhose on, and a white silk shirt. I sat in the sofa by her pretty feet. I put them in my lap and caressed them as I watched TV. After about 30 minutes, she slowly woke up.
“Mmmm! Hi sweety. How was your day?”
“Real good, mom. And yours?”
“Ahh you know, busy busy busy...but you know I like my store. So it's all good, Caroline!”
“I know, mommy!” I took one of her hosed feet to my nose and sniffed them real good. “MMmm mommy, they smell so divine. I love the scent of your pretty pantyhose feet!”
“He-he...I know, baby! Sniff my dirty pantyhose feet. I think you need to taste them too!? I know you want too!”
“Yes, mom. Whatever you wish...MMmmm!”
I put her hosed feet in my mouth and started sucking them so good. I loved how her pantyhose feet felt and tasted. Sucking her big toe like a little cock. Oh my god, yess! But then we heard a knock on the door. I quickly jumped up and ran to my room. And Margret went to open the front door. I listened out my bedroom door.
“Hello Margret, is Brian home? I spoke on the phone with him today, but he never showed up. So I wanted to make sure everything was ok!”
“Hold on, let me check his room...give me a second!”
“Sure, no problem, Miss!”
I heard Margret approach my room and walked inside. “It's your dad outside! I don't remember him being this hot! Ehmm, what should I say?”
“Shit, shit! What do I do? I can’t talk to him like this! Just say I’m not home. Please?!”
“Ok. But I think you should tell him about this! You can't keep this a secret all the time!” she said as she looked me up and down.
“Yes, ok. But not now!”
She rolled her eyes at me and walked to the front door again. “I’m sorry, Steve, but he is not home. And I tried calling him...he’s not picking up his cell!”
“I know...I tried that too! Can you please give this bag to him? It’s from his mom and me! As I don't see him that often and he become so independent, I wanted to let him know with this present. Please let him know I have been here!”
“I sure will do, Steve. Have a lovely day!”
“You too, Margret!” and she closed the door.
I came out in the kitchen, where I saw mom put a bag on the dinner table.
“It's from your dad. He said he’s worried about you!”
It was like a mini sports bag. I went over and opened it. And I couldn't believe my eyes. It was a stack load of money in there, and a letter.
“Mom, look. How...I ehmm...! Why?”
I opened the letter...
Dear sweety. Mommy just wanted to let you know that I’m doing fine in my new life. I’ve got everything I wish for here in France. I felt sad that you didn't say goodbye to me at the airport. But I can understand. I wanted to give you this as gift, and maybe because I think that I haven't always been the best mom for you. Therefore I’ll give you 50 thousand dollars in cash. I've talked to Steve too and he put 20 thousand in as well. He told me that he never hears from you and that you’re living at your friend, Nico's, mom’s house. You’ve become so independent and probably a real good boy. I hope you don't end up disappointing the people you love, as I did. I hope you come visit me some time. If you do decide to come, I’ll send you a ticket for a flight. Take care, my sweet boy. Mommy still loves you.
I couldn't say a word and I teared a bit up. Margret took the note and read it too. “Oh wow! That is some gift! And a really nice start for a life, Caroline! We need to open account for you!”
I was in shock that I now had around 70 thousand dollars. “Yeah, I think I need that! When can we do it? Because I don't feel very safe with that kind of money in a bag!”
“Let me make a phone call to see if I can set up a meeting today!”
She called the bank right away, and when they heard what kind of money there was to talk about, they had time right away! So the rest of the day went with setting up an bank account for me.
~*~*~*~*~*~*~*~*~*~
The next day was like every other day - but I had 70 thousand dollars now! I didn't really want or need anything! I thought about my mom, and if the money would make me forgive her. I don't know! On one hand, it showed me how much she loved me, and on the other, she had mostly been a bitch to me. But people change, I can say that for myself. I changed a lot. Why wouldn't she be able to change too? Maybe her life had become better and my stepdad seemed way better too - and hotter! I just wanted to thank him so much. He is the one who’s really been there for me. And now Margret was the one who had shaped me into the Caroline I am today! She had been much more a mother to me than my own.
It was Friday, and I decided to ring him up. The phone rang and I got nervous. I didn't know what to say.
“Hello Brian. How are you?”
“I'm good, Steve. I just wanted to say thanks for the huge amount of money...it's way too much!”
“I know it’s a lot of money, but you’re doing so fine, k**...and I hardly see you anymore. I'm so proud of you, and I hope it's a good start at life!”
“Thanks, dad. You’re gonna make me cry!” and I almost did!
“Why don't you come over tonight, then we can drink some whiskey and just talk?”
“Ok, I can come over!”
“But come over this time...don't dodge me again!”
“Sorry dad. I had a friend that had some trouble and he needed my help!”
“Ok. Just come over when you can! Can we order some Chinese food?”
“Sure. I'll take a quick shower and be right over!”
“Cya soon!”
“Bye, dad!”
~*~*~*~*~*~*~*~*~*~
My mom was out on business again, so I had the house for myself. I took a quick shower and cleaned myself good. I dried my hair, and lotioned my body. At first I just wanted to go as boy me, but the more I thought about the last time I sucked my stepdad’s cock, the more I felt the urge to go as Caroline. Plus, I wanted him to know me for who I am now!
I was starting to feel so naughty and decided to be a classy little pretty slut. First, I lubed up my steel dildo with a pink diamond at the end. I stuck it in my newly clean-shaven pussy. Oh, it felt so nice, but cold going inside of me. As it was in, I looked in the mirror spreading my butt cheeks and clearly seeing the diamond shining in the light. Mmmmm. Then I found a black garter belt with 3 straps on each side, in black and light pink. And that was the main theme for tonight. I had bought a nice outfit, all matching, light pink and black colours for a special occasion like this. I know it was so wrong of my doing this, but it felt so fucking right in whole my body. I pulled the black lace garter belt over my bum. I opened a brand new pack of stockings - they were black 25 denier stockings with light pink reinforced toes and sole, and a pink seem going on the back of the stockings with pink lace borders, the rest was all black nylon. I slid them on my smooth pretty legs, and oh boy, did they feel amazing! Knowing that my dad would see me in those, turned me on so much. I had put both stockings on and attached the pink straps of the garter belt to my nice stockings. I adjusted everything so it sat nice and tight. Over the garter belt I pulled on some nice lace pink see-thru panties, encasing my tiny dick that was already semi-erect. Again, I had to look in my mirror.
Seeing my hard nipples and fine lingerie was turning me on, but I had to control myself! I found the pink dress that I’d been waiting so long to try on. It was a lace dress with the skirt part long in the back and shorter in the front, showing off my fine stockinged legs in the front. The dress had lace sleeves to my elbows, and the body part of the dress was more of a satin material and looked more like a corset, with a zipper in the front going down to under my belly button. I jumped into the dress, pulled it over my bum, and put my arms in those pretty lace sleeves. Then at last, zipping myself up to my small firm perky breasts, and of course my nipples were poking the fabric. I looked so stunning. I could have jerked myself of right there! But no, I was way too horny and wanted to show myself to Steve, thinking about his big cock in my mouth. I did my usual makeup, but with pink eyeshadow on top of my dark smoky eyes. I put on pink blush on my cheeks to make them pop, and nice bright pink lipstick. I put on my big black round glasses and it all fit together perfectly. I found a curling iron in Margret's room and made my black shoulder-length hair filled with curls. And WOW, if I must say so myself. I then pulled out some pink high heel platform sandals and put my pretty stockinged feet in them. I closed the sandals straps crossing my ankles. I went into Margret's room again and sprayed myself with one of her more mature smelling perfumes. I sprayed my neck, wrists, my breasts, and under my skirt - even a tiny bit on my feet and heels. I was so pleased with myself and I looked like a classy, nerdy, high-end prostitute - or just a real fine lady. I grabbed a bottle of ‘Pink’, from the liquor cabinet and called a cab. Then I put my leather jacket on. I borrowed a black little purse from Margret to put my stuff in it, and waited outside my house.
I was so excited on how this night was going to turn out.
Good Morning, Darling. Mommy had to go early this morning. I wanted to let you know that you don't need to take those drops anymore, for now. And your father called. He asked if he could talk to you. But you were asleep. Please call him back. Cya soon. Kisses from mom.
I picked up the phone and rang him up, and sat down with my coffee.
“Hello, this is Steve!”
“Hi Steve, it’s Brian!”
“Hello Brian. Long time since I heard from you! Are you doing ok? You sound a bit funny!?”
I coughed and spook with a deeper voice. “Yeah sure...I'm doing just fine. Just a little cold. Thanks for asking though! How are you holding up?”
“You know, busy as always...too much work! But it's all good! You know I don't have to share my money anymore. Get it? He-he!”
I didn't know if that was sad or he meant it. “He-he, yeah. Living the life, huh Steve?”
“Sure do, son. Well speaking of money, I got some for you. Or rather said, it is from your mom and me!”
Why would they give me money? For the lack of not being there?
“Oh really? Well I got something I wanna tell you! So it's a good time to meet and talk about it!”
“What’s up? Is everything ok?”
“Yes, dad...everything is just fine. But I wanna tell you in person, than over the phone!”
“Well you can come anytime, I’ve got the day of work, so I’ll be home!”
“Let me finish my coffee and I’ll be over in an hour or so. Sounds good?”
“Sure do, son. Cya then!”
And I hung up the phone. I wanted to tell him about myself, and that I pretty much was Caroline most of the time now. And that was one of the reasons I wanted to let Peter know too! I didn't want to hide the fact that I’m mostly a girl now.
After I finished my coffee, I took a quick shower and found something to wear. I found a red top and a little black cardigan, to put over my top. It really only covered my arms, so my hard nipples were showing through the red top. Some black jeans I had cut up into very short shorts. And then I found some red opaque pantyhose. No panties or bra. Just light and easy! Plus, summer time was just around the corner, and it was a nice weather outside. I did my Gothy makeup with a hint of red eyeshadow on top off the black, a nice dark red lipstick, and put my glasses on. I had gathered some different coloured ones and picked out some red ones. At last, I put my blonde wig on, and adjusted it to perfection. Checking myself in the mirror, and I looked hot as always, but I was getting a bit tired of the wig. And now that my own hair was getting longer, I thought about using my own black hair. It was a little longer than shoulder length. It didn't look that nice, but for now I kept my blonde wig on. I found my black leather jacket, and some black ballerinas. I looked at myself in the mirror, and everything was perfect. My god, I loved to dress up as a smoking hot girl. Nothing better than to be Caroline! I sprayed myself with perfume and off I went.
I arrived at my stepdad’s apartment and took the elevator up to the 4th floor. I stood outside and was trying to get the courage to ring the doorbell. But then from behind me, I heard a voice saying. “Hello, can I help you Miss?”
I jumped scared and let out a little scream.
He laughed, “Ha-ha. Sorry Miss, I didn't mean to scare you!”
I turned around and saw Steve, with mail in his hands. But when he saw me, his eyes looked me up and down, and finished with a smile. I of course panicked again and lied. “It’s fine. I think I’ve got the wrong address. Sorry to bother you. I'll just be on my way. Have a nice day!”
“A fine girl like yourself couldn't bother me! I was waiting for my son, and he should have been here by now! I don't think he’s coming by today. So why don't you come inside for a cup of coffee as a sorry for scaring you?”
‘Pull yourself together and just tell him that you're Caroline!’ But no, I just had to say “He-he...I could use a coffee. Thanks, I’ll take the offer!” ‘He is going to be so disappointed when he knows it is me!’
He unlocked the door and he let me in first. “I’m Steve, by the way!”
I took my jacket off and hung it up. “I’m Caroline. Nice to meet you, Steve!” ‘Oh stupid Caroline...just tell him that it is you!’
I was about to take my ballerinas off, but he stopped me. “You don't have to take them off. It's pretty dirty anyway. I need to vacuum soon!”
I stepped inside and saw his apartment for the first time. It wasn't dirty at all, and it all looked very nice and modern. With nice exposed brick walls and beams. Huge window side and a nice big balcony with an amazing view over the city. And a new kitchen with a vintage look. I loved this place. Maybe I should have moved in with my stepdad? He was in the kitchen getting the coffee ready.
“So who you came to visit?”
without hesitation I told him some bullshit story. “My grandpa. But it must be on the fifth floor and not the fourth! He just moved in and his getting old!”
“Ah, I see. The floors look a lot alike and no proper signing of the door numbers. Milk and sugar?”
The more I lived as Caroline, I found many things different between Brian and Caroline. One of them was that Caroline liked milk in her coffee, and Brian liked it black.
“No sugar. But I would like some milk thanks!”
He opened the fridge, but he didn't have milk. “I seem to have run out of milk. No worries, there is a 7/11 just a block away. Wait here, I’ll be right back!”
“That's very kind of you, but you don't have to...I'll drink it black!”
“Stop it. It won't take long 10 minutes, and I’m back!” and off he went.
I thought that my stepdad looked more muscular. Had he been training or was it just my mind playing tricks? When I lived at home, he just seemed so nerdy, but now he looked more like a real man. He smelled good too. ‘Fuck...stop thinking things like that. He raised you pretty much from when you were 5 years old!’
I walked around the apartment. Huge living room with the kitchen, and 3 other doors. One door let to a nice bathroom with big hot tub. The other room was like an office with a lot of computer parts laying around. And lastly, his bedroom. I gently walked inside, and there was a person laying under the blankets of the huge king-size bed. It really scared me at first, but at a closer look, I saw it was one of those real-size fucking dolls! I always wanted one for myself, but that kind of money I could only dream of having. Those dolls were so expensive and I couldn't wrap my mind around that my stepdad had one of those. I got a closer look and pulled the blanket away. It had black long hair and a pretty face. It was just lying on the bed in a black corset with a garter belt, black stockings and black lace panties on. Those breasts could as well had been mine because they looked like the same size as mine. It was really amazing...but it had a bulge in her panties! At first I thought it maybe was a dildo. Then I pulled the panties aside, and to my surprise, the doll had a cock! My mind was blown. ‘Was my dad into chicks with dicks?’ I looked closer and she also had a pussy and asshole. I couldn't believe that my dad had a ‘fucking doll’ with a cock! ‘Did he know something about me? Why would he? Maybe he just liked that? Fuck, I wish I’d never seen this!’
I covered the doll and put the blanket back as before. I closed the door to his bedroom, sat down in his sofa, and all kinds of thoughts just went through my head of the doll I’d just seen. 3 minutes later, my stepdad was back with milk.
~*~*~*~*~*~*~*~*~*~
“Hi. Now let's get that coffee!”
“Thanks Steve. You’re too kind!”
He came and sat down in the sofa and placed the coffee on the table. I took a sip.
“Mmmm...that is really good coffee!”
“Should be. The beans are from Columbia. Rich in taste and smell!” He smiled at me. His eyes was staring at my hard nipples, almost poking through my red top. I should have put a bra on anyway. I blushed, and couldn't believe that my stepdad was checking me out like that.
“So you have a son?”
I don't know why, but Steve looked more buff and acting more like a man than I had seen before. I got kinda turned on by him.
“Yes. But it is my stepson. His mom left me for another man. That fucking whore!”
I didn't see that coming, him calling my mom a whore! And I just kept on being Caroline, not to make him suspect me. “Really? How could she leave a fine man like you?”
He laughed “Ha-ha. Thanks! But now I’m free of her, I kinda feel a lot better with myself!”
I glanced down at his black sweatpants and saw a huge bulge between his legs. Wow, Steve had a huge one! Mmmm.
‘No...stop it, Caroline...it is your stepdad!’
Without even realizing it, I crossed my red opaque pantyhose leg over my other leg. His eyes wandered all over my thighs and down at my feet. I was sitting there dangling my leg and was heel-popping with my ballerina shoe. I even saw him lick his lips a little. I then came to realize that I was full-on flirting with Steve. My own stepdad! And when I tried to stop myself, I accidently dropped my shoe, and my red pantyhose foot was showing. My face blushed, but then he picked up my shoe.
“Wow...that is one pretty foot. Let me help you!”
Steve gently grabbed my ankle and glided his finger over my hosed foot and very slowly put my ballerina shoe back on my foot. I smiled at him with a flirty look.
‘Why am I doing this? Pull yourself together!’ But I guess my mind wanted something else. So I dropped my shoe again. “Oops...clumsy me!” I wiggled and pointed my red hosed foot in his sight and he got a smirky look on his face.
“Yeah, clumsy you. Mmmm!” Then he adjusted his cock in his sweatpants, and I played so innocent.
“I'm so sorry...I didn't mean to turn you on like that! He-he!”
“Oh you bad girl. I can't believe this is happening! I love that I can see your black nail polish through those pretty red pantyhose. Mmmm, yes!”
I couldn't believe that my own stepdad said that about my feet! I popped my other shoe off and placed my feet by his stiff cock outside his sweatpants. His eyes got big and just stared at my red hosed feet. And I found his cock, and it was big one too! I started grinding my feet up and down his big cock, feeling it hard. Real hard! Mmmm!
“Oh fuck, that is so hot! Ahhh! My wife never did anything like this! Wow! Mmmmm...such pretty pantyhose feet!”
I wanted to see his big cock so badly! I wanted to feel it between my toes! I tried to stay as cool as I could, but my tiny dick got so hard too! Good thing it was tucked away and up in my tight fitting shorts.
“Shouldn't you pull that lovely cock out, Steve?”
Without a second to spare, he pulled out a real nice long thick cock. And I was surprised that Steve had such a beautiful cock - and he was even all shaven smooth.
“Wow. Girls most love that big cock?!”
“He-he...Well to be honest, I haven't been with anyone since my wife left me!”
I had no clue, but then again that maybe explains the sexdoll! My pantyhose feet gently grabbed a hold of his cock and started pushing up and down.
It felt amazing between my hosed toes. Even pre-cum oozed out of it and smeared in my pantyhose. Mmmm yess. That feeling that I was pleasing a man with my pantyhose feet was the best! His cock was so stiff, and I know I had small girl’s feet, but his cock was as big as my feet! He laid his head back in sheer pleasure, and I just kept going and going, grinding that pretty cock with my red pantyhose feet. My head was blowing inside with the thought of me doing this to Steve, and I wanted to taste his huge cock in my mouth! And as I saw more pre-cum come out, I thought ‘it is now or never’. I stood up and got in front of him, pulled my top down under my breasts, revealing my breasts and my rock hard nipples for him to see. His jaw dropped and he just stared. I got on my knees, Put his cock in between my small firm titties, and pushed with my hands against them, to grind my tits up and down his cock. And of course, my mouth downward to his big nice dick head filled with pre-cum, and stuck my tongue out. So everytime I pushed down on his cock, his nicely shaped mushroom head filled with pre-cum got smeared on my tongue. Fuck yesss! The taste was amazing, and my body started twitching a bit. He was moaning a lot.
“Fuck...You’re so beautiful...Ahhh Mmmm...I love your fucking tits...AHH!”
I just kept going up and down and tried to get every last drop of his pre-cum in me. Shit, he turned me on so much with his words...I had to have his big cock in my mouth! I let go with my tits and just opened my mouth widely and just swallowed his whole cock down all the way. I felt his mushroom head way past my throat, and I fucking loved it! I held it there and gagged on it, making it all wet of my saliva. I sucked it so hard and good. And as I would come up for air, I used both my hands jerking his pretty cock. Tears were running down my eyes and felt my mascara running, but I loved every second sucking my stepdad off.
“HOLY FUCK...AHHH!! Mmmmm Fuck...Yes! Suck it good! Uhhh, baby!”
He pushed my head back onto his cock and held me down and I was full on gagging on it. I felt my tiny dick getting harder and pushed my red pantyhose so hard that it popped out past my shorts. He grabbed a hold of my hair and pulled me off his cock. He got a bit wild and held a good grip on me as he pulled my head to one side. “You are a fucking little cocksucking whore, aren't you?”
I nodded eagerly. I shook my head and he slapped me on my cheek. Not hard, but in the good kinda a way.
“Answer me, little slut!”
I nodded again. “Yes I am! I love sucking cock. And especially yours, Steve. Mmmm!”
And he shook my head again - but then my blonde wig fell off. My black shoulder-length hair was now exposed. He froze and I froze. He looked at me real good. I was so fucking busted! I was ready to lay down and die, but his face got a huge smile on.
“Holy shit...You just became 10 times hotter! Man, how is that possible? Suck me till I cum in that little slut mouth of yours!”
He threw the wig over the side of the sofa and grabbed my real hair instead and pushed me down over his big tasty cock. He didn't know anything - Must have been all the makeup, my glasses and my long hair! I was in heaven. So I gave it all I had - and I craved his cock! He held real good on my head and fucked my mouth so hard my tits were bouncing. Mmmm, I felt beautiful and loved every bit of being a girl. I loved sucking my stepdad’s cock. In fact, it felt so good that I didn't even feel that I cummed on myself and my red pantyhose. I was enjoying every stroke his cock hit me with, deep down my throat. He went on for 5 minutes - and then he couldn't hold it anymore. He didn't even moan, more like grunting noises - and a huge load of cum squirted out of his cock and he kept on fucking my mouth as he cummed. So much inside of my mouth - I tasted his delicious cum from deep down my throat and all over my tongue and even my lips! Holy fuck, I never sucked any cock like that before!
He gently let go of my head. “Shit...I’m sorry, Caroline...I got carried away! Hope you’re ok?”
I stood up and tucked my tits away as I gave him a big smile. “I'm all good, Steve! I love sucking cock, so don't worry about it!”
He looked down at my red pantyhose thighs and he saw huge wet stains on both of my thighs. My tiny dick had crawled away and inside the shorts again. “Wow...Ehmm, I see you came too? You really do love sucking cock! Dirty girl, he-he!”
I looked down at myself and saw the huge stains my tiny dick had made on my pretty red pantyhose - and my face turned red instantly. “Oh no...I didn't even feel that. I'm so embarrassed!”
“Come on, don’t be. Glad you enjoyed yourself too! Don't worry about that...I think I’ve got some of my wife’s old clothes...I'll be right back!” He went into his bedroom and came back very quickly, and had something in his hand. “Here you go. The bathroom is over there!” He pointed at it.
“Thanks!”
I walked into the bathroom and locked the door. I looked at the clothes he’d given me. It was a red mini-skirt with black little dots on, and a pair of black opaque pantyhose, still some of my favourite kind. I took my cum-stained shorts and pantyhose off and threw them on the ground. I cleaned myself with a bit a water and dried myself. I pulled those black pantyhose on, and on top, the red mini-skirt. It looked very good with my top and my cardigan, but I knew this was not my mother clothes! She almost never wore pantyhose and definitely no mini-skirt! Nope, this must have been clothes that were meant for his ‘fucking doll’. Good thing I was close to the same size, though they fit a bit snugly. I picked up my dirty stained hose and shorts and walked out into the living room. And as he saw me, he stared me up and down.
“Wow...Really beautiful, Caroline!”
I blushed “Thanks Steve. And thanks for letting me borrow this!”
“Ah, don't mention it. And just keep it. The least I can do after what you gave me!” And he winked at me.
“He-he! Where is your trash can?”
“Under the sink! Just one more thing!”
I went over and threw my cummed hose and shorts out. “What's that?”
He smiled at me. “You look way better without your blonde wig. So I would leave out the wig in the future!”
I was flattered that he liked me without my blonde wig. It just confirmed that I didn't need it anymore. But I never thought the idea would come from my stepdad!
“I appreciate your honesty...and I’ll for sure think about it! I really need to go now!”
“Ok, thanks again, you sexy lady. He-he!”
I walked out of the apartment and took the elevator down. I never ever in my life had any thoughts about my stepdad like that before. But I’ve never seen him as a real man like that! He had gotten more muscular and was more ‘man’ than ever - and that turned me on! I felt so lucky to have tasted his delicious cock. But I should have told him everything, and was sure he was gonna find out when he pulled my wig off. But that showed me even more that I looked like a girl than ever before. From that day, I decided to use my own long black hair.
~*~*~*~*~*~*~*~*~*~
I reached home and saw Margret's car outside.
“Hello mom!” I walked into the living room where I found her asleep on the sofa. She had on a blue skirt with white 40 denier pantyhose on, and a white silk shirt. I sat in the sofa by her pretty feet. I put them in my lap and caressed them as I watched TV. After about 30 minutes, she slowly woke up.
“Mmmm! Hi sweety. How was your day?”
“Real good, mom. And yours?”
“Ahh you know, busy busy busy...but you know I like my store. So it's all good, Caroline!”
“I know, mommy!” I took one of her hosed feet to my nose and sniffed them real good. “MMmm mommy, they smell so divine. I love the scent of your pretty pantyhose feet!”
“He-he...I know, baby! Sniff my dirty pantyhose feet. I think you need to taste them too!? I know you want too!”
“Yes, mom. Whatever you wish...MMmmm!”
I put her hosed feet in my mouth and started sucking them so good. I loved how her pantyhose feet felt and tasted. Sucking her big toe like a little cock. Oh my god, yess! But then we heard a knock on the door. I quickly jumped up and ran to my room. And Margret went to open the front door. I listened out my bedroom door.
“Hello Margret, is Brian home? I spoke on the phone with him today, but he never showed up. So I wanted to make sure everything was ok!”
“Hold on, let me check his room...give me a second!”
“Sure, no problem, Miss!”
I heard Margret approach my room and walked inside. “It's your dad outside! I don't remember him being this hot! Ehmm, what should I say?”
“Shit, shit! What do I do? I can’t talk to him like this! Just say I’m not home. Please?!”
“Ok. But I think you should tell him about this! You can't keep this a secret all the time!” she said as she looked me up and down.
“Yes, ok. But not now!”
She rolled her eyes at me and walked to the front door again. “I’m sorry, Steve, but he is not home. And I tried calling him...he’s not picking up his cell!”
“I know...I tried that too! Can you please give this bag to him? It’s from his mom and me! As I don't see him that often and he become so independent, I wanted to let him know with this present. Please let him know I have been here!”
“I sure will do, Steve. Have a lovely day!”
“You too, Margret!” and she closed the door.
I came out in the kitchen, where I saw mom put a bag on the dinner table.
“It's from your dad. He said he’s worried about you!”
It was like a mini sports bag. I went over and opened it. And I couldn't believe my eyes. It was a stack load of money in there, and a letter.
“Mom, look. How...I ehmm...! Why?”
I opened the letter...
Dear sweety. Mommy just wanted to let you know that I’m doing fine in my new life. I’ve got everything I wish for here in France. I felt sad that you didn't say goodbye to me at the airport. But I can understand. I wanted to give you this as gift, and maybe because I think that I haven't always been the best mom for you. Therefore I’ll give you 50 thousand dollars in cash. I've talked to Steve too and he put 20 thousand in as well. He told me that he never hears from you and that you’re living at your friend, Nico's, mom’s house. You’ve become so independent and probably a real good boy. I hope you don't end up disappointing the people you love, as I did. I hope you come visit me some time. If you do decide to come, I’ll send you a ticket for a flight. Take care, my sweet boy. Mommy still loves you.
I couldn't say a word and I teared a bit up. Margret took the note and read it too. “Oh wow! That is some gift! And a really nice start for a life, Caroline! We need to open account for you!”
I was in shock that I now had around 70 thousand dollars. “Yeah, I think I need that! When can we do it? Because I don't feel very safe with that kind of money in a bag!”
“Let me make a phone call to see if I can set up a meeting today!”
She called the bank right away, and when they heard what kind of money there was to talk about, they had time right away! So the rest of the day went with setting up an bank account for me.
~*~*~*~*~*~*~*~*~*~
The next day was like every other day - but I had 70 thousand dollars now! I didn't really want or need anything! I thought about my mom, and if the money would make me forgive her. I don't know! On one hand, it showed me how much she loved me, and on the other, she had mostly been a bitch to me. But people change, I can say that for myself. I changed a lot. Why wouldn't she be able to change too? Maybe her life had become better and my stepdad seemed way better too - and hotter! I just wanted to thank him so much. He is the one who’s really been there for me. And now Margret was the one who had shaped me into the Caroline I am today! She had been much more a mother to me than my own.
It was Friday, and I decided to ring him up. The phone rang and I got nervous. I didn't know what to say.
“Hello Brian. How are you?”
“I'm good, Steve. I just wanted to say thanks for the huge amount of money...it's way too much!”
“I know it’s a lot of money, but you’re doing so fine, k**...and I hardly see you anymore. I'm so proud of you, and I hope it's a good start at life!”
“Thanks, dad. You’re gonna make me cry!” and I almost did!
“Why don't you come over tonight, then we can drink some whiskey and just talk?”
“Ok, I can come over!”
“But come over this time...don't dodge me again!”
“Sorry dad. I had a friend that had some trouble and he needed my help!”
“Ok. Just come over when you can! Can we order some Chinese food?”
“Sure. I'll take a quick shower and be right over!”
“Cya soon!”
“Bye, dad!”
~*~*~*~*~*~*~*~*~*~
My mom was out on business again, so I had the house for myself. I took a quick shower and cleaned myself good. I dried my hair, and lotioned my body. At first I just wanted to go as boy me, but the more I thought about the last time I sucked my stepdad’s cock, the more I felt the urge to go as Caroline. Plus, I wanted him to know me for who I am now!
I was starting to feel so naughty and decided to be a classy little pretty slut. First, I lubed up my steel dildo with a pink diamond at the end. I stuck it in my newly clean-shaven pussy. Oh, it felt so nice, but cold going inside of me. As it was in, I looked in the mirror spreading my butt cheeks and clearly seeing the diamond shining in the light. Mmmmm. Then I found a black garter belt with 3 straps on each side, in black and light pink. And that was the main theme for tonight. I had bought a nice outfit, all matching, light pink and black colours for a special occasion like this. I know it was so wrong of my doing this, but it felt so fucking right in whole my body. I pulled the black lace garter belt over my bum. I opened a brand new pack of stockings - they were black 25 denier stockings with light pink reinforced toes and sole, and a pink seem going on the back of the stockings with pink lace borders, the rest was all black nylon. I slid them on my smooth pretty legs, and oh boy, did they feel amazing! Knowing that my dad would see me in those, turned me on so much. I had put both stockings on and attached the pink straps of the garter belt to my nice stockings. I adjusted everything so it sat nice and tight. Over the garter belt I pulled on some nice lace pink see-thru panties, encasing my tiny dick that was already semi-erect. Again, I had to look in my mirror.
Seeing my hard nipples and fine lingerie was turning me on, but I had to control myself! I found the pink dress that I’d been waiting so long to try on. It was a lace dress with the skirt part long in the back and shorter in the front, showing off my fine stockinged legs in the front. The dress had lace sleeves to my elbows, and the body part of the dress was more of a satin material and looked more like a corset, with a zipper in the front going down to under my belly button. I jumped into the dress, pulled it over my bum, and put my arms in those pretty lace sleeves. Then at last, zipping myself up to my small firm perky breasts, and of course my nipples were poking the fabric. I looked so stunning. I could have jerked myself of right there! But no, I was way too horny and wanted to show myself to Steve, thinking about his big cock in my mouth. I did my usual makeup, but with pink eyeshadow on top of my dark smoky eyes. I put on pink blush on my cheeks to make them pop, and nice bright pink lipstick. I put on my big black round glasses and it all fit together perfectly. I found a curling iron in Margret's room and made my black shoulder-length hair filled with curls. And WOW, if I must say so myself. I then pulled out some pink high heel platform sandals and put my pretty stockinged feet in them. I closed the sandals straps crossing my ankles. I went into Margret's room again and sprayed myself with one of her more mature smelling perfumes. I sprayed my neck, wrists, my breasts, and under my skirt - even a tiny bit on my feet and heels. I was so pleased with myself and I looked like a classy, nerdy, high-end prostitute - or just a real fine lady. I grabbed a bottle of ‘Pink’, from the liquor cabinet and called a cab. Then I put my leather jacket on. I borrowed a black little purse from Margret to put my stuff in it, and waited outside my house.
I was so excited on how this night was going to turn out.
Kaylin
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Crossdressed In Best Friend rsquo s Mom rsquo s Clothes 8
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Crossdressed In best friends mom clothes 3
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