Crossdressed in public
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Crossdressed In Best Friend’s Mom’s Clothes 11 free porn video
As I had fallen asleep - I started dreaming...
...I was licking Roxy’s pussy again.
“You’re such a good pussy licker!” and I kept going. She stopped me and pushed me onto my back. “Now I’m gonna suck your pussy, Caroline!”
I tensed up and was scared. She was sitting on my stockinged legs and grabbed my skirt and pulled it up. I only had on some pink panties. And in the dream, I had a huge cock. Her face looked shocked and was stunned.
“I'm so sorry, Roxy. I meant to tell you that I’m a guy!” The embarrassment, felt like forever.
I saw her face turning angry as hell. And she started shouting at me.
“What the fuck is that?! I'm not into shit like this! Fucking queer boy! I let a guy suck me! Oh fuck no...Fucking bitch!”
She started slapping me in the face. It made me cry so much. Then all of a sudden she was sitting on me with my huge cock in one hand - and her pretty folding knife in the other.
“This is what you get for taking the fucking piss out of me!”
I saw the knife swinging from above her head and down towards my big cock, and I was full on screaming. And right before she hit it, my eyes pop open.
I looked around. ‘Oh holy shit. Fucking nightmares!’
I just rested in bed and slowly woke up as I heard the birds outside. Enjoying the sun shining through the window, and felt the sun’s rays hitting my pantyhosed legs. It felt so good. Mmm. Suddenly I realised there was an arm wrapped around my stomach with a hand holding my tit. I then realise that Roxy was spooning me in her little brother’s bed.
‘No no no no no...This can't be happening!’ I heard her sleeping and felt her warm breath on the back of my neck. My nipple was so hard in her hand - it turned me on. But had she found out that I’m a guy? And how did I not sense her lay down with me? Guess I had a little too much last night. I couldn't take the thought from my dreams and wanted to get out of there. I tried slowly and gently lifting her arm away, but that just woke her up.
She yawned and said. “Mmmm...good morning, princess...thanks for last night! I hope you don't mind that I’m sleeping here with you? Just got so lonely in the living room!”
I made a little cough sound. “Ehh...it’s fine. Well rise and shine! Do you want some coffee?” I tried to get up, but her arm around me hold me back.
“Shhh...what's your hurry, princess?”
Her hand on my tit was gently rubbing my hard nipple. I bit my lips. Luckily, she couldn't see my face. I then felt her face move close to me, and her mouth was whispering right into my ear...
“You are so fine, Caroline...Mmmm!”
It tickled inside my body, in a good way when she spoke. Her purple pantyhosed legs were rubbing against mine. This was too much for me.
“Please don't...No, don't!”
I felt her arm going down my black bodystocking, and all the way down to my dark blue dotted skirt, and pulled it up over my stomach and said “Don't what? I can see you like it, Caroline!”
Her hand glided from my black pantyhose thigh and slowly up to my small erect dick. I could feel her hand searching for a pussy at first. Her fingers then wrapped around my dick. I heard a little gasp from her. I was so in shock right there, I froze completely. I think 10 seconds went by where she just pressed on it and squeezed it.
“Holy fucking shit...that's a surprise!”
I feared the worst and closed my eyes and wanted to cry.
“Mmmm...I like a pretty surprise like you. Naughty princess!”
I couldn't believe it! I feared what she might say or do, after all she is a lesbian, and been to prison for stabbing a man in the leg.
“I’ve never met anyone quite like you, Caroline!” she unbuttoned my body stocking at my crotch, and started playing with my tiny erect dick outside my pantyhose. I was in full lust and instantly started moaning. “Oh wow...that's the spot right there. Mmmm...that is a hot little clit you got there...so sensitive!” She kept on rubbing her pantyhose feet with mine.
My god, the feeling of being with pretty Roxy like this was turning me on so fucking much.
“Kiss me, you fucking tease!”
I turned my head and she placed her lips onto mine and we gently kissed. Then her tongue touched mine and it felt so sexy and passionate. So very different from a guy. So gentle and full of love. She even tasted sweet. My hosed feet pointed and felt hers do the same. Oh my god, I love this girl! She pulled my pantyhose down just under my erect dick so my balls were still under the hose. We kept on kissing as she started jerking my dick. My breathing was getting heavier as she played with me. I broke away from her kiss and straight on to moaning.
“Ahh. Mmmm yess...Ahh, Roxy! Your fingers feel so soft against my tiny dick!”
My dick got slapped like 3 times in a row. Each time my body twitched as she hit me.
“Fuck...you are such a bitch! A sexy motherfucking little pantyhose slut! Aren't girls like you referred to as sissy whores? Are you like that, princess?”
My face turned red, and as I was moaning I said “Mmmm Yes...Roxy! AHH! I’m sorry...AH!”
“Don't be, princess. I don't care about that! To me you're a beautiful girl, that also happens to be a sissy whore! Mmmm, I like you, Caroline!”
As she said that, she got up on her knees in bed, put her head by my tiny dick and placed her pussy down on my mouth as I laid down in bed. 69. She rubbed her pussy against my face. I stuck my tongue out, immediately tasting her delicious wet pussy. It got me so fucking horny.
“Now don't judge me. This is my first time sucking a dick!”
Oh my god, she was really gonna suck me! I felt her lips sucking themselves onto my little erect dick. She now had it inside her mouth. And oh boy, it felt amazing! I’m sure she tasted my leaking pre-cum, and soon after I felt her trying to suck it out of me like a straw. My black nyloned legs were shaking while she sucked me, and she was thrusting her hips in my face. Her moaning, while sucking me, sounded so nice. And soon after she was cumming.
“Open your fucking mouth, slut! ARGHH! Mmmm...Cumming...Ah...AHH!”
Her juices rained straight down my throat and I happily accepted it. It drove me so crazy, and felt my dick was about to cum. She pushed her head against my cock, sucking hard. And of boy did I cum! That orgasm was one of the best in a long time. I cummed so much. But she kept on swallowing it all. As I was done cumming, she sat up in bed and looked at me with a smile. Then she leaned into kiss me. My cum was swapped into my mouth from a stunning-looking Roxy. We kissed for like 2 full minutes, and I was blown away. I was in the clouds right now. I just laid there staring at the ceiling, and she cuddled up beside me.
“Mmmm...your cum taste kinda good, Caroline. My naughty little princess!”
“Thanks, I think. I love sucking your tasty pussy, Roxy!”
She had her head by my tit and was gliding one finger over my bodystocking-clad stomach. “I know you do. Mmmm!”
We were just lying in bed enjoying the moment. After a while, I got up and said “I'm gonna make myself a coffee. You want one too, Roxy?”
She nodded with a smile as she cuddled up under the blanket. I boiled some water and made some instant coffee. I brought the coffees into the bedroom, and handed her the cup.
“Thanks for the lovely sex, Caroline. Or is it...?”
I felt a bit embarrassed. “No, my real name is Brian!”
“Ok, let's stick with Caroline...I like her!” I blushed. “So tell me how you become this pretty girl!”
I guessed I really liked her because I told her the most of my story. How my stupid mom left me and about my stepdad, Steve. And even how I lived with Margaret to become her maid and train to be a good girl. I just didn't mention the guys I’ve fucked - like my long-time best friend, my stepdad, and her little brother. Though I’m sure she knew the last one.
“Wow...your mother Margaret sounds kinky as hell. She did a great job with you!”
“Yeah, she is great...but I’m beginning to want to find my own ways!” She drank some of her coffee. And I asked her “Ehh...So...are you not angry at me? Ehmm...Well, for being a guy?”
She looked at me with a huge smile. “Listen...the only thing I see in this room are 2 horny girls that just had amazing sex. You are more of a girl than a lot of my previous girlfriends! Even with that little slutty clit between your fine pantyhose legs!”
Oh god, hearing her like that was the best feeling ever! I giggled and smiled. She put her coffee down on the bed table, and was about to suck me again, but we got interrupted by the front door opening, and heard Peter and Michael talking. I got under the blanket, but Roxy didn't seem to care one bit. Peter entered the room first and saw his sister only in her purple pantyhose with a hole at the gusset. He then looked over at me. “Have you been having sex together?”
Then Michael popped his head inside the room. His jaw dropped instantly when he saw Roxy. “Holy damn! You are the most beautiful woman I’ve ever seen, Roxy!”
Roxy was pissed. “Shut it, Michael! What the fuck do you guys want?”
Peter stared at me, and my tits that were hanging out from the body stocking. I hadn't realised they were showing. “Ehh Caroline...your tits are showing!”
Michael then looked at me and my tits - and his jaw dropped again. I quickly covered myself with my bodystocking. “Holy fuck...I’m gonna faint! 2 beautiful women!”
Roxy pushed Michael out of the room, and slammed the door in his face. “What you want, Peter?”
“Chill, sis. Just gonna grab my bag and we are off!” He faced me again. “So Caroline, ehh. I guess this is goodbye? Was nice knowing you!”
Roxy was still pretty angry. “Dude, cut the shit! First, you fuck her and then leave, and trying to play it all dramatic. Get out of here and leave her alone! I thought you were better than this!?”
He nodded. “Yes, I agree. And that's why I came to apologise for taking advantage of you. Ehh, even if you are...You know...And that's it! I hope we can be friends when and if I get back?”
I looked at him and saw he really meant it. “I forgive you, Peter. And I wish you the best!”
He grabbed a huge military bag from the floor and said bye.
“Bye, and don't get yourself killed, brother!”
And Peter and Michael left again. I felt kinda sad because I really liked Peter. But I had Roxy to comfort me. And she was something else. I was starting to form a crush on her.
She put her jeans on and top on. “Hey Caroline. I'm gonna go make Jeff a visit, and get some stuff in town. I need some new clothes too. So I don't know when I’ll be back!”
“That's ok. I'll need a talk with my mom. Here is my number. Call me when you get back! If you want to of course...not my apartment!”
“I don't wanna be alone later. I will call you, princess!” She kissed my cheek and off she went too. I heard the car start up and leave.
I put a little music on and tidied up the place, while I thought about all the great things that had happened. Mmmm, I felt so comfortable as a pretty girl. Walking around in nice outfits all day. With my gorgeous pantyhose and nylons. I loved doing my makeup and doll myself up. I really loved being a girl with all my heart. All this thinking about it reminded me to take my drops.
After I cleaned the place, I put my leather jacket on and my black high-heeled ankle boots (they still felt a bit moist from Roxy drinking pink from my heel), grabbed my purse and key and locked up, and bicycled home to mom.
I arrived like a half an hour later at home. I walked inside and saw mom in the kitchen in her red bathrobe. And she had black nylons on, in fluffy red slippers.
“Hi mom!”
“Oh hi there! Where have you been, sweety?”
“Over at a friend’s!”
“Really...dressed like that? So he knows your secret?”
I didn't wanna tell my mom about Roxy. “Ehh yeah, he knows!”
She crossed her legs and her robe showed her leg more and I saw her in stockings. Not pantyhose today. She looked so sexy in those. “So he fucked my little girl hard? Hmm Yess...he did...I see it in your eyes!”
I nodded while I stared at her dangling her pretty slipper with crossed stockinged leg. “So you haven't missed mommy at all?”
I took my leather jacket off and threw it over the chair. “Oh god yes...I missed you. But you work all the time! I gotta be honest...I think I’m ready to move on!”
She laughed right in my face. “You are ready to move on when I say you are! You look so pretty today, Caroline! Come over to mommy!”
I stood right at her side and got smacked on my ass.
“Get down on your knees in front of me, and rub my tired nylon feet!”
I pulled one slipper of her nylon foot and rubbed one to start with.
“Ahh yes. That feels nice. Mmmm! So you like watching mommy getting fucked by your dad?”
I took the other foot out and placed her feet in my lap, massaging her pretty toes. “It looked so hot. Did his cock feel good inside you, mom?”
“Oh yes, sweety. He made me cum multiple times with his big cock!”
My dick was getting erect while we talked about it, and it was really nice touching mommy's pretty nylon feet again.
“Anyway, Caroline. Me and your father...we just started talking when he came by to visit you with some clothes. I asked him inside and offered him a drink. And one thing led to another. I think I’m in love with your dad, Caroline!”
What was she talking about? How could she be in love after one night? “So this was not a one nightstand?”
“No...I really wanna see if we can get a relationship going! He is a good and sexy man. He’s coming over tonight again!”
I found it all a bit strange. “But is this not going too fast you think?”
“Well you just told me you wanna move on! And I don't wanna lose time! I'm not 30 anymore. So your timing couldn't be more perfect! I can't do more for you anyway. You’ve turned into such a pretty girl...and cute! I've done my part...I need to focus more on my shop!”
I looked down at her black nylon feet, and felt a bit sad. I was gonna miss this incredible sex with Margaret. “Nice to hear it’s going good with your shop! I'm gonna miss this so much, mommy!”
She reached out with her hand and raised me from the floor. “Let's do it one last time, my pretty girl!” She led me into her bedroom and laid me in the middle of the bed. She then bound my hands to corner of the bedpost with a red robe. She pulled my dark blue skirt with white dots off me, and was now laying in bed with my black bodystocking and black Wolford nylon pantyhose underneath - and heels on. Then Margaret pulled my nylonclad legs to each side and bound them as well to the other corners of the bed. Then I got blindfolded.
“What are you doing, Margaret?”
“Keep your mouth shut!”
I felt her pull my bodystocking to one side freeing my tiny dick. She then pulled my dick out of my pantyhose and did something to my small penis and tucked it away again. “I'll be back later, Caroline. Take a nap or something!” Then I heard the door shut.
I wiggled my body and tried to get free, but I was bound tightly to the bed. And as soon I realised that I can't get out, I relaxed and eventually fell asleep.
~*~*~*~*~*~*~*~*~*~
I woke up with a shock when the door slammed again. For a moment I forgot where I was. Then my bound nylon feet got sucked on each of them. And oh god, it felt amazing as they started sucking. After a few minutes of getting my nylonclad feet sucked, I felt someone grab my tit and squeezed it. “Ahh...”
“Shh, Caroline!”
It was Mom. But I didn't feel like mom's hands! These hands grabbing my tits were from a man! I then felt someone get in the bed, and then I got a pussy rubbed in my face.
“Suck my horny pussy, sweety!”
I stuck my tongue out and sucked her good, and I forgot how good it tasted. She grinded her crotch in my face. I felt someone else getting in the bed and kneeled down between my legs. My nylon feet got caressed and then tickled. Oh my god, it felt so good! My tiny dick got erect instantly!
His hands were touching my legs, going up to my crotch and unbuttoned the bodystocking.
Mom was getting more wet and gently started moaning. I loved the sound of mommy moaning, it always turned me on like crazy.
Then he said “Mmm yess! Look at the small dick with a pretty bow on it! Poking those pretty pantyhose. Ahh yess. My sweet daughter!”
I knew that voice. It was Steve! My body was twitching a bit with all of the excitement I was getting. How did it all turn out like this? Margaret’s wet pussy was running down my cheeks. And as I kept on sucking mom, I blurted out “Oh god yes, daddy. Mmmm!” I started moaning too. Then my pantyhose got ripped open and he stroked my erect dick.
“God, I love how you look in your pretty black pantyhose and bodystocking. Mmmm...daddy's pretty girl!”
Mom got up and pulled my blindfold off. The light was bright at first, but when my eyes adjusted, I saw daddy infront of me with his big stiff cock. But then mom stuck her ass in my face while kneeling down. “Suck my ass, you little slut!”
I spit and sucked it for her.
“Ahh yes, bitch! Mmmm...get in there!” and she pressed her ass against my face where I couldn’t breath. “Give me your delicious cock, Steve!”
“Yes, my love. Suck it. MMmmm!”
I couldn't see anything with my mom’s ass in my face. But it sounded fucking sexy! And he definitely was fucking mommy’s mouth, because I heard a lot of gagging and gasping for air!
They stopped and I heard mom say “Give our pretty daughter your delicious cock in her needy pussy! Show how much we love our little girl!”
My butt-plug was pulled out and I felt a dick poking my hole. “Arghh...Daddy. Mmmm yess...Please...” I didn't get a chance to say anything else before he showed his stiff cock in me. My nylonclad toes were wiggling and my feet curled up from the sheer pleasure of his beautiful cock penetrating my pussy. I screamed out. “AAHH!! Fuck yess! Please fuck me, daddy!”
Mommy then started sucking my little dick. Holy fuck, it came to me as a big surprise! The lust I was feeling was insane!
Dad fucked me harder and faster. “Ahh yess, you like that, my pantyhose slut. Feeling daddy inside you. Ahh...Ahh...Mmm!”
God, the feeling of getting sucked and fucked at the same time was too intense. And I cummed so hard in mom’s mouth. “Arhh...I’m cumming! AHHH...Uhmm...ARhh, god yes...”
...and of course, mother swallowed it all down and looked so satisfied. Mother got on top of me with her ass at my dick. “Fuck me now, Steve!”
“Mmm yes, baby!” He pulled out of me and I heard mom moan as soon he stuck his big cock inside her. “Oh this is so good. Fucking 2 pretty girls at the same time. Mmm yess!” He changed like every 5 strokes - then her pussy, then my girly pussy. I felt great.
Mother started rubbing her clit and screaming. “My god...ARhh fuck...I love your big cock, Steve! Arghh...cum inside me!”
It was so sexy listening to them both climax. Her whole body was shaking and my dad cummed inside of her.
“ARGHH...Arhhh Fuck yes...MMMM!”
My dad pulled out of mom and into my ass with his sloppy cum-covered cock. Mom instantly got up in bed and hovered her pussy over my mouth and said “Open your pretty mouth, Caroline. Be a good girl and swallow daddy's cum out of mommy's wet pussy!” She pushed out a huge load of cum right into my open mouth. The taste was amazing - a sweet mixture of wet pussy and cum. It felt so good going down my throat. Such a nice threat for a horny little pantyhose sissy.
Dad was still fucking me gently and I moaned quietly. “Mmmm Ahh...! Thanks Mom. Ahh, thanks Dad! Ah...Mmm!”
Mom got down from the bed and leaned over and kissed me on my cheek. “You’re welcome, Caroline. Mommy gonna take a long warm bath!” and she left the room.
My dad’s sloppy cock got stiff inside me again. And as he kept on thrusting my pussy, he untied my legs. He gathered my nylon feet by his face and sniffed them good while he was fucking me.
“Oh I missed my pretty girl...and your gorgeous nylon toes. Mmmm, Caroline!”
He put my nylon toes in his mouth, and I watched with pleasure. I was moaning loudly again as I felt his big cock going deeper inside of me. He stared at me while I just laid there taking his big cock.
“Mmm...I love your big cock...AHH...in me, daddy!”
He pushed my nylonclad legs almost to my tits. He stood up in bed and almost jump-fucking me, thrusting his cock even deeper than before. My feet curled up instantly, followed by a loud scream when he hits me. “Arghh yess...I love looking at your lewd face as I fuck my daughter hard! ARghh Ahh...Fucking you in that tight sissy hole. Ahh argh...Daddy is gonna...cum inside your little slut pussy...ARGH...AHH...! Take it, bitch!”
And I did.
He cummed so hard in my pussy and he hit something inside me. Of course, my body shook violently, and after thrusting me twice more, another load of cum shoots out of my tiny dick and up my body stocking. My dad saw it, and fucked me hard again as I came. The feeling was empowering. My whole body was numb of pleasure, and couldn't even scream! I just took it.
“Fuck...! Love when you cum, sweety! Ahh mmm...cumming hard from only fucking your pussy. Daddy’s girl, mmm!” He pulled out and felt his huge load of cum just oozing out of me. I was totally done after the fucking. I just laid there breathing heavy, as dad untied my arms.
“Thank you, dad...I really enjoyed that!”
“You’re welcome, sweety. So you know this was the last time, right? Because you know...Margaret and me wanna see if we can get things to work!” He sat his naked ass down beside me in bed, as I laid there.
“Yeah, I kinda figured that out! It’s ok, dad! If someone deserves happiness, it's you and mom. I’m happy for you guys!”
“Thanks, Caroline. I knew you would understand!”
“How did you and mom decide to fuck me?”
He looked at me and said “We really wanted to give it a shot, But as we both had been dumped from a marriage, we agreed to tell each other everything. That included you! So we agreed to give you one last ride!”
“I'll accept that. It was really nice getting fucked by you again, dad. Mmm!”
“Oh yes, baby, it was. Anyway, I’m moving in here in the weekend. And since I bought the apartment, I’m leaving it for you!”
I sat my ass up in bed. “What? You can't mean that, dad?! Save it for later...if it’s not working out with you and Margaret!”
“No. We really wanna believe in this. So I don't want anything to fall back on. I really love this woman, Caroline. So please take the bloody apartment and make it your own place!”
I hugged him so hard. My own apartment, with 3 rooms, a big bathroom, a huge living room with a kitchen, and big balcony with the best view over the city! I couldn't believe it.
My dad handed me a key. “I really wish the best for you, Caroline!”
I took it, sitting there with cum dripping out of my pussy while covered in cum. This was a nice moment.
Mom stepped in the room. “The bathroom is free. Go clean yourself up, Caroline!”
“Yes mom!” And went to the bathroom and took my clothes off, and jumped in the shower. I was really getting my dad's place. Moreover, I was happy for them! That the people I really loved had found their own love together. My dad needed a woman like Margaret, and Margaret definitely deserved the best with all she had done for me. She’d turned me into an obedient pretty pantyhose girl.
It came to mind that I really fancied Roxy. I loved the fact that she’s into pantyhose feet too. She even enjoys wearing pantyhose too under her tight jeans. Mmm, that ass. She knew what she wanted, and could defend for herself. And she blew my mind when she didn't get mad that I used to be a guy. She just sucked my clitty and sucked all judgemental thoughts in my head out. I missed her already, and got hard just thinking about beautiful Roxy.
After the shower, I went to the bedroom to change. I put on some black opaque pantyhose and decided to spice them up with some glitter fishnet pantyhose over my opaque hose. Then found a white tank top and a black long-sleeved lace top. I picked out a silk skirt with like zebra print on it. It was a bit long and went under my knees, but that didn't matter because the skirt felt so light and the feeling of the silk rubbing my pantyhosed legs was amazing. I then applied my makeup with eyeshadow and mascara, then a nice subtle lipstick. Sprayed myself with perfume and put on my glasses. I pulled out a white pair of ‘Puma’ sneakers, and put my pretty pantyhose feet in them. Looking at myself in the mirror for one last check and adjustments - and I was perfect! I walked into the kitchen where I found mom and dad in bathrobes and eating toast with eggs, it was like 8 in the evening.
“Oh sweetie, you look so pretty!”
“Thank you, mom!”
“Damn yeah. I would fuck you again if I hadn't found real love right here!” He looked at mom and they started kissing. He-he! Oh god, they were really in love.
“I guess, thanks dad! Again, thanks for everything. I better get going. Someone is waiting for me!”
Mom turned around. “Who is waiting for you? Is it that Peter guy? He was a nice boy!”
“Ehh, not really...”
“Well then who is it?”
I grabbed my purse and leather jacket. “Doesn’t matter right now. Not sure if she likes me back!”
“What? Really a girl? You need to bring her over. I wanna meet her!”
“I really gotta go. And stop, Margaret...probably won't turn out anyway!”
“Ok...I’ll keep my mouth shut. But I just want you to be happy!”
Now I felt bad. “I know...sorry mom! I gotta go. I'll call you soon. Bye!”
My dad just waved at me. “Bye hun!”
And off I went on mother’s bicycle.
...I was licking Roxy’s pussy again.
“You’re such a good pussy licker!” and I kept going. She stopped me and pushed me onto my back. “Now I’m gonna suck your pussy, Caroline!”
I tensed up and was scared. She was sitting on my stockinged legs and grabbed my skirt and pulled it up. I only had on some pink panties. And in the dream, I had a huge cock. Her face looked shocked and was stunned.
“I'm so sorry, Roxy. I meant to tell you that I’m a guy!” The embarrassment, felt like forever.
I saw her face turning angry as hell. And she started shouting at me.
“What the fuck is that?! I'm not into shit like this! Fucking queer boy! I let a guy suck me! Oh fuck no...Fucking bitch!”
She started slapping me in the face. It made me cry so much. Then all of a sudden she was sitting on me with my huge cock in one hand - and her pretty folding knife in the other.
“This is what you get for taking the fucking piss out of me!”
I saw the knife swinging from above her head and down towards my big cock, and I was full on screaming. And right before she hit it, my eyes pop open.
I looked around. ‘Oh holy shit. Fucking nightmares!’
I just rested in bed and slowly woke up as I heard the birds outside. Enjoying the sun shining through the window, and felt the sun’s rays hitting my pantyhosed legs. It felt so good. Mmm. Suddenly I realised there was an arm wrapped around my stomach with a hand holding my tit. I then realise that Roxy was spooning me in her little brother’s bed.
‘No no no no no...This can't be happening!’ I heard her sleeping and felt her warm breath on the back of my neck. My nipple was so hard in her hand - it turned me on. But had she found out that I’m a guy? And how did I not sense her lay down with me? Guess I had a little too much last night. I couldn't take the thought from my dreams and wanted to get out of there. I tried slowly and gently lifting her arm away, but that just woke her up.
She yawned and said. “Mmmm...good morning, princess...thanks for last night! I hope you don't mind that I’m sleeping here with you? Just got so lonely in the living room!”
I made a little cough sound. “Ehh...it’s fine. Well rise and shine! Do you want some coffee?” I tried to get up, but her arm around me hold me back.
“Shhh...what's your hurry, princess?”
Her hand on my tit was gently rubbing my hard nipple. I bit my lips. Luckily, she couldn't see my face. I then felt her face move close to me, and her mouth was whispering right into my ear...
“You are so fine, Caroline...Mmmm!”
It tickled inside my body, in a good way when she spoke. Her purple pantyhosed legs were rubbing against mine. This was too much for me.
“Please don't...No, don't!”
I felt her arm going down my black bodystocking, and all the way down to my dark blue dotted skirt, and pulled it up over my stomach and said “Don't what? I can see you like it, Caroline!”
Her hand glided from my black pantyhose thigh and slowly up to my small erect dick. I could feel her hand searching for a pussy at first. Her fingers then wrapped around my dick. I heard a little gasp from her. I was so in shock right there, I froze completely. I think 10 seconds went by where she just pressed on it and squeezed it.
“Holy fucking shit...that's a surprise!”
I feared the worst and closed my eyes and wanted to cry.
“Mmmm...I like a pretty surprise like you. Naughty princess!”
I couldn't believe it! I feared what she might say or do, after all she is a lesbian, and been to prison for stabbing a man in the leg.
“I’ve never met anyone quite like you, Caroline!” she unbuttoned my body stocking at my crotch, and started playing with my tiny erect dick outside my pantyhose. I was in full lust and instantly started moaning. “Oh wow...that's the spot right there. Mmmm...that is a hot little clit you got there...so sensitive!” She kept on rubbing her pantyhose feet with mine.
My god, the feeling of being with pretty Roxy like this was turning me on so fucking much.
“Kiss me, you fucking tease!”
I turned my head and she placed her lips onto mine and we gently kissed. Then her tongue touched mine and it felt so sexy and passionate. So very different from a guy. So gentle and full of love. She even tasted sweet. My hosed feet pointed and felt hers do the same. Oh my god, I love this girl! She pulled my pantyhose down just under my erect dick so my balls were still under the hose. We kept on kissing as she started jerking my dick. My breathing was getting heavier as she played with me. I broke away from her kiss and straight on to moaning.
“Ahh. Mmmm yess...Ahh, Roxy! Your fingers feel so soft against my tiny dick!”
My dick got slapped like 3 times in a row. Each time my body twitched as she hit me.
“Fuck...you are such a bitch! A sexy motherfucking little pantyhose slut! Aren't girls like you referred to as sissy whores? Are you like that, princess?”
My face turned red, and as I was moaning I said “Mmmm Yes...Roxy! AHH! I’m sorry...AH!”
“Don't be, princess. I don't care about that! To me you're a beautiful girl, that also happens to be a sissy whore! Mmmm, I like you, Caroline!”
As she said that, she got up on her knees in bed, put her head by my tiny dick and placed her pussy down on my mouth as I laid down in bed. 69. She rubbed her pussy against my face. I stuck my tongue out, immediately tasting her delicious wet pussy. It got me so fucking horny.
“Now don't judge me. This is my first time sucking a dick!”
Oh my god, she was really gonna suck me! I felt her lips sucking themselves onto my little erect dick. She now had it inside her mouth. And oh boy, it felt amazing! I’m sure she tasted my leaking pre-cum, and soon after I felt her trying to suck it out of me like a straw. My black nyloned legs were shaking while she sucked me, and she was thrusting her hips in my face. Her moaning, while sucking me, sounded so nice. And soon after she was cumming.
“Open your fucking mouth, slut! ARGHH! Mmmm...Cumming...Ah...AHH!”
Her juices rained straight down my throat and I happily accepted it. It drove me so crazy, and felt my dick was about to cum. She pushed her head against my cock, sucking hard. And of boy did I cum! That orgasm was one of the best in a long time. I cummed so much. But she kept on swallowing it all. As I was done cumming, she sat up in bed and looked at me with a smile. Then she leaned into kiss me. My cum was swapped into my mouth from a stunning-looking Roxy. We kissed for like 2 full minutes, and I was blown away. I was in the clouds right now. I just laid there staring at the ceiling, and she cuddled up beside me.
“Mmmm...your cum taste kinda good, Caroline. My naughty little princess!”
“Thanks, I think. I love sucking your tasty pussy, Roxy!”
She had her head by my tit and was gliding one finger over my bodystocking-clad stomach. “I know you do. Mmmm!”
We were just lying in bed enjoying the moment. After a while, I got up and said “I'm gonna make myself a coffee. You want one too, Roxy?”
She nodded with a smile as she cuddled up under the blanket. I boiled some water and made some instant coffee. I brought the coffees into the bedroom, and handed her the cup.
“Thanks for the lovely sex, Caroline. Or is it...?”
I felt a bit embarrassed. “No, my real name is Brian!”
“Ok, let's stick with Caroline...I like her!” I blushed. “So tell me how you become this pretty girl!”
I guessed I really liked her because I told her the most of my story. How my stupid mom left me and about my stepdad, Steve. And even how I lived with Margaret to become her maid and train to be a good girl. I just didn't mention the guys I’ve fucked - like my long-time best friend, my stepdad, and her little brother. Though I’m sure she knew the last one.
“Wow...your mother Margaret sounds kinky as hell. She did a great job with you!”
“Yeah, she is great...but I’m beginning to want to find my own ways!” She drank some of her coffee. And I asked her “Ehh...So...are you not angry at me? Ehmm...Well, for being a guy?”
She looked at me with a huge smile. “Listen...the only thing I see in this room are 2 horny girls that just had amazing sex. You are more of a girl than a lot of my previous girlfriends! Even with that little slutty clit between your fine pantyhose legs!”
Oh god, hearing her like that was the best feeling ever! I giggled and smiled. She put her coffee down on the bed table, and was about to suck me again, but we got interrupted by the front door opening, and heard Peter and Michael talking. I got under the blanket, but Roxy didn't seem to care one bit. Peter entered the room first and saw his sister only in her purple pantyhose with a hole at the gusset. He then looked over at me. “Have you been having sex together?”
Then Michael popped his head inside the room. His jaw dropped instantly when he saw Roxy. “Holy damn! You are the most beautiful woman I’ve ever seen, Roxy!”
Roxy was pissed. “Shut it, Michael! What the fuck do you guys want?”
Peter stared at me, and my tits that were hanging out from the body stocking. I hadn't realised they were showing. “Ehh Caroline...your tits are showing!”
Michael then looked at me and my tits - and his jaw dropped again. I quickly covered myself with my bodystocking. “Holy fuck...I’m gonna faint! 2 beautiful women!”
Roxy pushed Michael out of the room, and slammed the door in his face. “What you want, Peter?”
“Chill, sis. Just gonna grab my bag and we are off!” He faced me again. “So Caroline, ehh. I guess this is goodbye? Was nice knowing you!”
Roxy was still pretty angry. “Dude, cut the shit! First, you fuck her and then leave, and trying to play it all dramatic. Get out of here and leave her alone! I thought you were better than this!?”
He nodded. “Yes, I agree. And that's why I came to apologise for taking advantage of you. Ehh, even if you are...You know...And that's it! I hope we can be friends when and if I get back?”
I looked at him and saw he really meant it. “I forgive you, Peter. And I wish you the best!”
He grabbed a huge military bag from the floor and said bye.
“Bye, and don't get yourself killed, brother!”
And Peter and Michael left again. I felt kinda sad because I really liked Peter. But I had Roxy to comfort me. And she was something else. I was starting to form a crush on her.
She put her jeans on and top on. “Hey Caroline. I'm gonna go make Jeff a visit, and get some stuff in town. I need some new clothes too. So I don't know when I’ll be back!”
“That's ok. I'll need a talk with my mom. Here is my number. Call me when you get back! If you want to of course...not my apartment!”
“I don't wanna be alone later. I will call you, princess!” She kissed my cheek and off she went too. I heard the car start up and leave.
I put a little music on and tidied up the place, while I thought about all the great things that had happened. Mmmm, I felt so comfortable as a pretty girl. Walking around in nice outfits all day. With my gorgeous pantyhose and nylons. I loved doing my makeup and doll myself up. I really loved being a girl with all my heart. All this thinking about it reminded me to take my drops.
After I cleaned the place, I put my leather jacket on and my black high-heeled ankle boots (they still felt a bit moist from Roxy drinking pink from my heel), grabbed my purse and key and locked up, and bicycled home to mom.
I arrived like a half an hour later at home. I walked inside and saw mom in the kitchen in her red bathrobe. And she had black nylons on, in fluffy red slippers.
“Hi mom!”
“Oh hi there! Where have you been, sweety?”
“Over at a friend’s!”
“Really...dressed like that? So he knows your secret?”
I didn't wanna tell my mom about Roxy. “Ehh yeah, he knows!”
She crossed her legs and her robe showed her leg more and I saw her in stockings. Not pantyhose today. She looked so sexy in those. “So he fucked my little girl hard? Hmm Yess...he did...I see it in your eyes!”
I nodded while I stared at her dangling her pretty slipper with crossed stockinged leg. “So you haven't missed mommy at all?”
I took my leather jacket off and threw it over the chair. “Oh god yes...I missed you. But you work all the time! I gotta be honest...I think I’m ready to move on!”
She laughed right in my face. “You are ready to move on when I say you are! You look so pretty today, Caroline! Come over to mommy!”
I stood right at her side and got smacked on my ass.
“Get down on your knees in front of me, and rub my tired nylon feet!”
I pulled one slipper of her nylon foot and rubbed one to start with.
“Ahh yes. That feels nice. Mmmm! So you like watching mommy getting fucked by your dad?”
I took the other foot out and placed her feet in my lap, massaging her pretty toes. “It looked so hot. Did his cock feel good inside you, mom?”
“Oh yes, sweety. He made me cum multiple times with his big cock!”
My dick was getting erect while we talked about it, and it was really nice touching mommy's pretty nylon feet again.
“Anyway, Caroline. Me and your father...we just started talking when he came by to visit you with some clothes. I asked him inside and offered him a drink. And one thing led to another. I think I’m in love with your dad, Caroline!”
What was she talking about? How could she be in love after one night? “So this was not a one nightstand?”
“No...I really wanna see if we can get a relationship going! He is a good and sexy man. He’s coming over tonight again!”
I found it all a bit strange. “But is this not going too fast you think?”
“Well you just told me you wanna move on! And I don't wanna lose time! I'm not 30 anymore. So your timing couldn't be more perfect! I can't do more for you anyway. You’ve turned into such a pretty girl...and cute! I've done my part...I need to focus more on my shop!”
I looked down at her black nylon feet, and felt a bit sad. I was gonna miss this incredible sex with Margaret. “Nice to hear it’s going good with your shop! I'm gonna miss this so much, mommy!”
She reached out with her hand and raised me from the floor. “Let's do it one last time, my pretty girl!” She led me into her bedroom and laid me in the middle of the bed. She then bound my hands to corner of the bedpost with a red robe. She pulled my dark blue skirt with white dots off me, and was now laying in bed with my black bodystocking and black Wolford nylon pantyhose underneath - and heels on. Then Margaret pulled my nylonclad legs to each side and bound them as well to the other corners of the bed. Then I got blindfolded.
“What are you doing, Margaret?”
“Keep your mouth shut!”
I felt her pull my bodystocking to one side freeing my tiny dick. She then pulled my dick out of my pantyhose and did something to my small penis and tucked it away again. “I'll be back later, Caroline. Take a nap or something!” Then I heard the door shut.
I wiggled my body and tried to get free, but I was bound tightly to the bed. And as soon I realised that I can't get out, I relaxed and eventually fell asleep.
~*~*~*~*~*~*~*~*~*~
I woke up with a shock when the door slammed again. For a moment I forgot where I was. Then my bound nylon feet got sucked on each of them. And oh god, it felt amazing as they started sucking. After a few minutes of getting my nylonclad feet sucked, I felt someone grab my tit and squeezed it. “Ahh...”
“Shh, Caroline!”
It was Mom. But I didn't feel like mom's hands! These hands grabbing my tits were from a man! I then felt someone get in the bed, and then I got a pussy rubbed in my face.
“Suck my horny pussy, sweety!”
I stuck my tongue out and sucked her good, and I forgot how good it tasted. She grinded her crotch in my face. I felt someone else getting in the bed and kneeled down between my legs. My nylon feet got caressed and then tickled. Oh my god, it felt so good! My tiny dick got erect instantly!
His hands were touching my legs, going up to my crotch and unbuttoned the bodystocking.
Mom was getting more wet and gently started moaning. I loved the sound of mommy moaning, it always turned me on like crazy.
Then he said “Mmm yess! Look at the small dick with a pretty bow on it! Poking those pretty pantyhose. Ahh yess. My sweet daughter!”
I knew that voice. It was Steve! My body was twitching a bit with all of the excitement I was getting. How did it all turn out like this? Margaret’s wet pussy was running down my cheeks. And as I kept on sucking mom, I blurted out “Oh god yes, daddy. Mmmm!” I started moaning too. Then my pantyhose got ripped open and he stroked my erect dick.
“God, I love how you look in your pretty black pantyhose and bodystocking. Mmmm...daddy's pretty girl!”
Mom got up and pulled my blindfold off. The light was bright at first, but when my eyes adjusted, I saw daddy infront of me with his big stiff cock. But then mom stuck her ass in my face while kneeling down. “Suck my ass, you little slut!”
I spit and sucked it for her.
“Ahh yes, bitch! Mmmm...get in there!” and she pressed her ass against my face where I couldn’t breath. “Give me your delicious cock, Steve!”
“Yes, my love. Suck it. MMmmm!”
I couldn't see anything with my mom’s ass in my face. But it sounded fucking sexy! And he definitely was fucking mommy’s mouth, because I heard a lot of gagging and gasping for air!
They stopped and I heard mom say “Give our pretty daughter your delicious cock in her needy pussy! Show how much we love our little girl!”
My butt-plug was pulled out and I felt a dick poking my hole. “Arghh...Daddy. Mmmm yess...Please...” I didn't get a chance to say anything else before he showed his stiff cock in me. My nylonclad toes were wiggling and my feet curled up from the sheer pleasure of his beautiful cock penetrating my pussy. I screamed out. “AAHH!! Fuck yess! Please fuck me, daddy!”
Mommy then started sucking my little dick. Holy fuck, it came to me as a big surprise! The lust I was feeling was insane!
Dad fucked me harder and faster. “Ahh yess, you like that, my pantyhose slut. Feeling daddy inside you. Ahh...Ahh...Mmm!”
God, the feeling of getting sucked and fucked at the same time was too intense. And I cummed so hard in mom’s mouth. “Arhh...I’m cumming! AHHH...Uhmm...ARhh, god yes...”
...and of course, mother swallowed it all down and looked so satisfied. Mother got on top of me with her ass at my dick. “Fuck me now, Steve!”
“Mmm yes, baby!” He pulled out of me and I heard mom moan as soon he stuck his big cock inside her. “Oh this is so good. Fucking 2 pretty girls at the same time. Mmm yess!” He changed like every 5 strokes - then her pussy, then my girly pussy. I felt great.
Mother started rubbing her clit and screaming. “My god...ARhh fuck...I love your big cock, Steve! Arghh...cum inside me!”
It was so sexy listening to them both climax. Her whole body was shaking and my dad cummed inside of her.
“ARGHH...Arhhh Fuck yes...MMMM!”
My dad pulled out of mom and into my ass with his sloppy cum-covered cock. Mom instantly got up in bed and hovered her pussy over my mouth and said “Open your pretty mouth, Caroline. Be a good girl and swallow daddy's cum out of mommy's wet pussy!” She pushed out a huge load of cum right into my open mouth. The taste was amazing - a sweet mixture of wet pussy and cum. It felt so good going down my throat. Such a nice threat for a horny little pantyhose sissy.
Dad was still fucking me gently and I moaned quietly. “Mmmm Ahh...! Thanks Mom. Ahh, thanks Dad! Ah...Mmm!”
Mom got down from the bed and leaned over and kissed me on my cheek. “You’re welcome, Caroline. Mommy gonna take a long warm bath!” and she left the room.
My dad’s sloppy cock got stiff inside me again. And as he kept on thrusting my pussy, he untied my legs. He gathered my nylon feet by his face and sniffed them good while he was fucking me.
“Oh I missed my pretty girl...and your gorgeous nylon toes. Mmmm, Caroline!”
He put my nylon toes in his mouth, and I watched with pleasure. I was moaning loudly again as I felt his big cock going deeper inside of me. He stared at me while I just laid there taking his big cock.
“Mmm...I love your big cock...AHH...in me, daddy!”
He pushed my nylonclad legs almost to my tits. He stood up in bed and almost jump-fucking me, thrusting his cock even deeper than before. My feet curled up instantly, followed by a loud scream when he hits me. “Arghh yess...I love looking at your lewd face as I fuck my daughter hard! ARghh Ahh...Fucking you in that tight sissy hole. Ahh argh...Daddy is gonna...cum inside your little slut pussy...ARGH...AHH...! Take it, bitch!”
And I did.
He cummed so hard in my pussy and he hit something inside me. Of course, my body shook violently, and after thrusting me twice more, another load of cum shoots out of my tiny dick and up my body stocking. My dad saw it, and fucked me hard again as I came. The feeling was empowering. My whole body was numb of pleasure, and couldn't even scream! I just took it.
“Fuck...! Love when you cum, sweety! Ahh mmm...cumming hard from only fucking your pussy. Daddy’s girl, mmm!” He pulled out and felt his huge load of cum just oozing out of me. I was totally done after the fucking. I just laid there breathing heavy, as dad untied my arms.
“Thank you, dad...I really enjoyed that!”
“You’re welcome, sweety. So you know this was the last time, right? Because you know...Margaret and me wanna see if we can get things to work!” He sat his naked ass down beside me in bed, as I laid there.
“Yeah, I kinda figured that out! It’s ok, dad! If someone deserves happiness, it's you and mom. I’m happy for you guys!”
“Thanks, Caroline. I knew you would understand!”
“How did you and mom decide to fuck me?”
He looked at me and said “We really wanted to give it a shot, But as we both had been dumped from a marriage, we agreed to tell each other everything. That included you! So we agreed to give you one last ride!”
“I'll accept that. It was really nice getting fucked by you again, dad. Mmm!”
“Oh yes, baby, it was. Anyway, I’m moving in here in the weekend. And since I bought the apartment, I’m leaving it for you!”
I sat my ass up in bed. “What? You can't mean that, dad?! Save it for later...if it’s not working out with you and Margaret!”
“No. We really wanna believe in this. So I don't want anything to fall back on. I really love this woman, Caroline. So please take the bloody apartment and make it your own place!”
I hugged him so hard. My own apartment, with 3 rooms, a big bathroom, a huge living room with a kitchen, and big balcony with the best view over the city! I couldn't believe it.
My dad handed me a key. “I really wish the best for you, Caroline!”
I took it, sitting there with cum dripping out of my pussy while covered in cum. This was a nice moment.
Mom stepped in the room. “The bathroom is free. Go clean yourself up, Caroline!”
“Yes mom!” And went to the bathroom and took my clothes off, and jumped in the shower. I was really getting my dad's place. Moreover, I was happy for them! That the people I really loved had found their own love together. My dad needed a woman like Margaret, and Margaret definitely deserved the best with all she had done for me. She’d turned me into an obedient pretty pantyhose girl.
It came to mind that I really fancied Roxy. I loved the fact that she’s into pantyhose feet too. She even enjoys wearing pantyhose too under her tight jeans. Mmm, that ass. She knew what she wanted, and could defend for herself. And she blew my mind when she didn't get mad that I used to be a guy. She just sucked my clitty and sucked all judgemental thoughts in my head out. I missed her already, and got hard just thinking about beautiful Roxy.
After the shower, I went to the bedroom to change. I put on some black opaque pantyhose and decided to spice them up with some glitter fishnet pantyhose over my opaque hose. Then found a white tank top and a black long-sleeved lace top. I picked out a silk skirt with like zebra print on it. It was a bit long and went under my knees, but that didn't matter because the skirt felt so light and the feeling of the silk rubbing my pantyhosed legs was amazing. I then applied my makeup with eyeshadow and mascara, then a nice subtle lipstick. Sprayed myself with perfume and put on my glasses. I pulled out a white pair of ‘Puma’ sneakers, and put my pretty pantyhose feet in them. Looking at myself in the mirror for one last check and adjustments - and I was perfect! I walked into the kitchen where I found mom and dad in bathrobes and eating toast with eggs, it was like 8 in the evening.
“Oh sweetie, you look so pretty!”
“Thank you, mom!”
“Damn yeah. I would fuck you again if I hadn't found real love right here!” He looked at mom and they started kissing. He-he! Oh god, they were really in love.
“I guess, thanks dad! Again, thanks for everything. I better get going. Someone is waiting for me!”
Mom turned around. “Who is waiting for you? Is it that Peter guy? He was a nice boy!”
“Ehh, not really...”
“Well then who is it?”
I grabbed my purse and leather jacket. “Doesn’t matter right now. Not sure if she likes me back!”
“What? Really a girl? You need to bring her over. I wanna meet her!”
“I really gotta go. And stop, Margaret...probably won't turn out anyway!”
“Ok...I’ll keep my mouth shut. But I just want you to be happy!”
Now I felt bad. “I know...sorry mom! I gotta go. I'll call you soon. Bye!”
My dad just waved at me. “Bye hun!”
And off I went on mother’s bicycle.
Annalisa
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Crossdressed In Best Friend rsquo s Mom rsquo s Clothes 8
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