Dressing Up Part 3 free porn video

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It has been nearly two years since my sisters caught me dressing up. Since then my mother had put me on a strict diet and gave me pills to make me into a girl. I have been transitioning slowly and now have a girly figure. I love my round ass and small soft breasts.

I now have my own wardrobe with many sexy clothes that I just love wearing. Mom has also made sure that my sisters look after me every once in a while, and they had all been really good to me.

It was just after my eighteenth birthday and Jessica decided it was a good idea if I was a true girl and had sex. Not me fucking a girl, but a big guy fucking me. I wasn’t really opposed to the idea, it, in fact, turned me on. Jessica said she has a few bisexual guy friends that would love to fuck me, but first I would have to dress more girly than I have ever dressed before.

Jessica took me to her bedroom where Tina and Haley were waiting. I loved my sisters and I had now been naked in front of them many times. Since they had caught me two years ago I have been naked or dressed up in front of them many times. I had even slept with them in the biblical sense a few times.

I was told to strip and Haley giggled when she saw how hard I was in front of them.

“Nat,” as my name was now. “I want you to wear these sexy leopard print bra and panties, I got them especially for you.”

Haley held out a small packet and handed it to me. The panties were a thong and after tucking my cock between my legs as I had done every day for the past two years, felt the string go up the crack of my ass. The bra fit perfectly, cupping my small breasts and making them look bigger than they were. My sisters all looked at me with approval.

Tina stood up and took my hand. She lifted a black lace dress that left plenty to see. She helped me step into the dress and zipped up the back. My body was clearly seen underneath the dress and the leopard print underwear looked amazing through the dress. I did look fine and I have to say that would have fucked the girl looking back at me in the mirror.

Jessica gave me a pair of shiny black heels to finish off my outfit. The whole outfit together looked amazing and I felt proud of wearing it all.

Led me by the hand to the toilet, my other sisters followed. She took out her makeup bag and laid out the contents. She spent the best part of half an hour doing my makeup, it was flawless. I looked more feminine than I already did, making my cock twitch against its flimsy covering.

Tina stood behind me and pulled all my long hair into her hand. I watched in the mirror as she deftly braided my hair into a thick braid. It looked stylish as well as sexy, it was similar to Angelina Jolie’s braid in Tomb Raider.

All three of my sisters seemed pretty pleased with the way they had dressed me up. I was pleased too and knew that whoever it was that Jessica had arranged for me to be with would love me.

The front doorbell rang, and Jessica jumped and pulled me close to her.

“That will be Jason. He’s a really cute guy but also very effeminate. He is bisexual so if you want to do anything to him, he will let. Just remember, this for you to explore your sexuality with him. Don’t be shy and if you want to take charge, just remember he’s a big guy so don’t try hitting or anything like that, because if he hits you back, he’ll knock you out.”

We all trooped downstairs, Jessica leading me by the hand. I was told to answer the door, but mom had already beaten me to it. I think Jason felt a bit uncomfortable telling mom that he was there to fuck her son, but mom always knew how to put people at ease.

Jason was tall, about six feet one. He wasn’t fat, but by no means skinny. He had muscles and at the same time, he was soft and almost ladylike. He wore loose fitting clothes and, in an attempt, to look manlier he had a Mohawk. He was pretty, and he seemed to shift when he saw me. He drawled slightly that made my cock twitch. I walked over to him and in front of my sisters and mother gave him a peck on the lips.

Mom seemed to usher my sisters out the room and I knew at least Jessica would be back to watch. As my mind wandered, Jason’s hands roamed my body and he seemed to find my treasure between my legs.

Without thinking or asking Jason pulled my cock free and wrapped his lips around it. It was the first time a guy touched me, let alone sucked me. It felt amazing and he seemed to grip my ass as he sucked and slurped on my dick. I slid my hand through his hair and started to move my ass. He seemed to like it and moaned his approval. I heard the door creak and saw Jessica sneak in. She gave me the thumbs up sign and took a seat in the corner of the room.

I started to lift my dress, but Jason took my hands away.

“Keep it on, you look so sexy all dressed up.”

I smiled and kissed him. He pulled me close and held me in his bearlike grip. He let go of me and stripped off. He had shaven his whole body and his cock, which wasn’t that big was bald. I took my seat on the couch and wrapped my hand around his hard cock. I could feel the blood pumping through his cock and I measured it in my hand.

Trying not to seem obvious I stroked his cock, measuring its length in my hand. Then I took his cock into my mouth as I wrapped my hand around my own cock. I made it seem like I was sucking him off and jerking because I was horny. I was horny, but really, I couldn’t resist comparing how large our cocks were, mine was bigger.

I sucked on his cock as best as I could, rolling my tongue around his bulbous head. He seemed to groan loudly, digging his finger into my braided hair and holding my head. He seemed to really enjoy me sucking him off and he started saying naughty things to me that really turned me on.

He pushed my head away and made me get onto all fours on the couch. He pulled my panties right down and buried his face in my ass. His tongue lapped at my butthole, making me squirm. As he licked my ass he jerked my cock.

I felt him move and take up position behind me when Jessica stopped him.

“Oh no, not like that Jason. If you’re going to fuck her, you’re going to wear a condom. No condom, no ass.”

Jason gave a sort of grunt as Jessica handed him a small red packet. I watched as Jason ripped it open and pulled out the condom from inside. I watched as he pulled it on and took up position once more.

I felt him spread my ass and slowly push his cock up my butt. Since I started dressing up I had been experimenting with putting things up my ass, but I never had a real cock up my ass before. He wrapped his arms around my waist as he started to slowly fuck me. I could feel his chest against my back as his cock seemed to slide easily in and out my butt.

He slowly started to pick up speed, slamming his cock as deep as he could. His grunts and whimpers turned me on so much that I had to jerk myself off. He seemed to pause, then grunted loudly as I felt the condom expand in my ass. I was a bit disappointed as he pulled out his cock and pulled off the used condom.

He sat back exhausted and I was left slightly unsatisfied.

“Okay, my turn.”

He looked at me like I was mad, but I wasn’t having any of it. I turned him over and spread his ass. Once again Jessica interjected. She held a condom in her hand and lovingly rolled it onto my cock. She kissed me on the cheek and gave me a pat on the ass.

Jason lay back on the couch, his legs spread, his ass open for me. I pushed my cock into his ass slowly, him being the first guy I ever had sex with. He grunted as I slid my cock in as deep as I could. It was warm and tight, like I was his first guy too. I held the back of his thighs as I started to build up a rhythm. His ass felt so good that I was soon pounding him as hard and fast as I could. His grunts and groans only made me try to fuck him harder.

Jason pushed me back, making my cock fall out his ass. I watched him get on all fours, shaking his ass at me. I took up position behind him and pushed my cock back in his ass. I grabbed his hips and started to slam my cock inside him as hard as I could. He grunted loudly, making me fuck him harder. I groaned loudly as I fucked him, knowing I wouldn’t last long.

I felt a hand on my ass and Jessica seemed to force to slow down.

“Relax, Nat. If you feel like you are going to cum, pull your cock out and take off the condom, then cum all over Jason’s ass. I want to see you cream all over his butt.”

I giggled and continued to fuck him as hard as I could. I knew I was close, but I it felt so good that I couldn’t pull out. At the last second, I pulled my cock out and pulled off the condom quickly. I pulled it off just in time as my cock seemed to explode, shooting cum all over Jason’s ass and back. I couldn’t stop cumming as my cock twitched and my body shook.

I fell onto the floor, panting and trying to catch my breath. Jason seemed to enjoy it and turned around and gave me a peck on the lips.

“Thanks cutie, that was amazing. Maybe I can come by again and we can have another round?”

I blushed, and Jessica seemed to interject once again.

“Thanks, Jason. If you want a shower there is a bathroom down the hall. For now, I need to take Nat to get washed and cleaned up.”

Jessica took me by the hand and led me upstairs. She led me into the bathroom when she helped me strip off. She stripped off too and made me stand still as she untied my hair.

She led me into the shower where she turned on the water and started to wash me down. She took care to wash my every crevice. Her finger penetrated my ass as she stroked my cock, making me quiver all over again. She knew what she was doing and soon have me Cummings all over her hand.

She washed me thoroughly, making sure every inch of my body was clean. After our shower, she dried me off and pulled me close and gave me a peck on the lips.

“Nat, you are now my little sister and as the youngest, I have to look out for you. That means only the boys I pick for you are good enough, and I know there are many girls, including our sisters that would love to sleep with you. I just want to make sure you aren’t taken advantage of.”

She gave me a pat on the butt and told me to go to my room. Once in my room, I saw Haley lying there on my bed, naked. She gave me a wicked grin and patter the bed next to her.



 

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It was a few days after fully dressing up and I knew I was hooked. I never felt more like myself or wanted to be more girly.With encouragement from my two best friends over the phone, I started wearing panties full time, I just had to make sure I didn’t change in front of my family.After a few days, I had gotten used to tucking my cock between my legs and loved feeling the tip of my cock against my ass.It was a Thursday, and as usual, my sisters were all in college until late and mom was out...

Incest
4 years ago
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Dressing for Ann

When I was a teenager we lived in a flat in an apartment block. There were four floors with a common entrance from the street and two flats on each floor. No lift/elevator just stairs. This arrangement was called a “close” in Scotland.Neighbours tended to look out for each other, taking in parcels, watering plants when people were on holiday etc. One year my mother “volunteered me” to look after the flat of a family on the floor below us. They were going on holiday for ten days and needed their...

4 years ago
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Crossdressing With My Mami

Hii, mere naam ankit hai. Main mumbai ka rahnewala hoo. Yeh kahani meri or meri mami ki hai jab hum sath me crossdressing kiya karte hai. Meri mami ma naam sabita hai. Unki lambai 5ft or woh thodi moti type ki hai. Unka koi baby nhi. Lekin fashion ke mamlo me save age rahti hai. Jab mai 10std me padta tha tab meri mami or mama culcutta se mumbai aaye. Yaha aane ki unki ek hee wajah thi paisa. Mujhe pahle se hee porn video dekhna achcha lagta tha. Mujhe femdom, bdsm, bondage jaisi porn bahut...

2 years ago
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Terrace View Apartments

Author's note: this is actually an older story that I wrote almost 15 years ago. A gentleman who has been encouraging me to write these sissy stories suggested that I post some of my older work online here, so that all of my stories would be available to read in one place. I hope that you enjoy this story; Sissy Michelle The Terrace View Apartments: Chapter 1 - Danielle I got a great job, right after I graduated from college. And while the job required that I relocate from my...

2 years ago
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Terrace Height Apartments

Many would have considered the Terrace Heights Apartments a dump. It was a square five-story building that stood atop a small ridge in southwestern Madison WI. The exterior was covered fake fieldstone, including the small balcony outside each apartment. That fieldstone was dirty and weathered from years of neglect. The first floor hallway was dimly lit. The dark green paint on the walls didn’t help any. The area off that hallway which held the vending machines was lit by the lights inside the...

3 years ago
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Book 1 Milady and the DragonChapter 7 Partings

Collin pulled her closer against his chest, his hands softly caressing her breasts, he heard her moan, he came awake, for a moment confused, looking at the sleeping woman in his arms he smiled softly at her. This was what he wanted, to feel her warm body and see her sweet face as he woke each morning, to hear her gentle breathing and feel it against his skin. His hand lay on her stomach, he gently rubbed his hand back and forth, A hatchling, no he corrected himself, a child, a human child,...

2 years ago
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The Three Signs Book 1 CathyChapter 15 Partings

After the first month or so of school, memories of the summer holidays had faded quickly. The study workload had increased dramatically, and I was glad I had taken the time to set myself a strict program. With schoolwork, practice for my next piano grade exam, and rehearsals and playing at the Mirage, Friday nights were my only regular free time. After the blow-up with Katey Jackson, I didn’t bother going to the youth group meetings on Sunday nights, which gave me some time to get things...

4 years ago
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Female DelightsChapter 2 Partings

The trouble came when EK0803 was assigned to wait on table at a banquet and was grabbed by an old retired army officer who had been a close friend of the Emir's father. He was now almost totally unable to perform sexually, and when he failed with EK0803 it was natural that he should blame her. He complained loudly to the Emir in front of several other guests and the Emir decreed that she should be given to the old man as some small recompense; he could then do with her whatever he wished....

3 years ago
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Dressing Up For The First Time Part 2

Dressing in my sisters clothes became a regular thing after about 2 months of doing it, I would use her vibrator on my ass at least once a week. My family was gone more often so it gave me plenty of time to prefect doing my make up, hair and shaving my legs. One night when my family WAS home i was looking for a pen to write a card. I went to my parents room to look for one and on my step mom's dresser was a small blue key, i had no clue what it would go to and for some reason it seemed...

2 years ago
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Dressing up as a girl

When i turned 16, I moved out. I was pretty skilled so i made good money freelancing. After i moved out i would often cross dress. I would buy nice dresses and lingeries then try them out. At first it was in my apartment only, but slowly i pushed myself. I would go out dressed as a girl. No one could say i was a boy from the inside. One night i wore a nice skirty dress and red panties then went towards a nearby park. It would make me alot excited. Although i never felt sexual attraction or...

4 years ago
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Dressing with Auntie Heather

Dressing with Auntie Heather It all started when I was a young, teenage boy. Just discovering my sexual urges by fantasizing about the girls in my class. For some reason I kept flashing on their cute little skirts and legs. Oh, how sexy their legs looked to me. Once in a while, I'd catch a glimpse of them while crossing their legs; you know that little flash of panty. It would just send shivers up my spine and then down directly to my cock. Thus the start of my fetish for woman's...

4 years ago
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Dressing Room Slut

(Chocolate Harlot in orgy with the band & Yolanda)I unloaded the gear from the van, time was getting on, and there was a lot to do before the set. I was a roadie for an up and coming band and tonight was to be their biggest venue so far. I humped the guitars, drums, amps, lights etc into the hall that the boys were playing in that night. As I worked I watched the early arrivals trickle in. They looked like the usual crowd, mostly teens and early twenties, but with a smattering of older...

3 years ago
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The Partnership

THE PARTNERSHIP June recognised the woman she was standing beside at the counter of the department store. She could not remember her name but knew she had seen her somewhere before. They were both in the lingerie department about to pay for their goods. In the woman's arms were two outlandish night dresses and several pairs of underwear that were definitely too big for her. "For the mother-in-law?" June inquired, and the lady replied, "Actually no, for my husband." June just...

1 year ago
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Dressing My Son

I had been suspicious of Mark's visits to my panty drawer for quite some time, but it wasn't until I bought that nanny-cam that I could confirm it. You can imagine my surprise when I began coming home from work and finding video after video of my f******n year-old son dressed in my bras, my knickerss, my dresses and high heels. That was the kind of behavior you might expect from a little girl, not a young boy. What amazed me most was how often you did it, how shameless he was in what he took....

3 years ago
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Tales From Mist WorldChapter 14 A Rude Awakening and Departure

Jake’s dreamed of him and Catherine standing on the bridge of the Karenna sailing the skies. In the dream, Catherine was holding their infant son. The eels were there along with many tiny eels floating around them. The dream changed, Jake was laying in his bed. Catherine was lightly stroking his face. Then she kissed him and covered him with a blanket. The dream ended and he drifted deeper into slumber. He was awoken by a knock on his cabin door. Jake sat up looking around. It took a few...

3 years ago
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Dressing Room With a Personal Touch

It was late afternoon. I was busy arranging new arrivals at the back of the store for window display and upcoming Spring theme when a distinct accent was heard coming from the front of the store. At eighteen, I was in love with the concept of latest fashion and fairly confident of my ability to come up with visuals that would draw the eye and guarantee sales. I could hear my name being summoned softly over loudspeaker. Adjusting my black skirt and white top with a sigh, I headed up front,...

Seduction
3 years ago
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Sexual Participation

Image of perfection Object of an affection in sexing Fantasizing freaky positions of you in submission Pushing pulling twisting and moaning A Place where I could store my erection Splendid features Tongue kissing fucking Look up cause I got mirrors on the ceiling Reflecting your ass bouncing silly Soon as you come in right away If you’re willing Splay your legs open Game played by 2 My sexual motivation Got you yelling spots for me to do? Amazed by the way you grind Just for fun I bet ill...

1 year ago
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Private compartment

"I'm sorry, Mr. Sands," the conductor explained, "I know you have a reservation for a private berth, but due to over booking all we have left is a compartment for two!!!" "Your berth mate is a nice young man, so we hope you can see your way clear to accept these alternate accommodations at no cost to you of course!!!" The train was about to leave the station and Vic Sands was just finding out that his reservation on the Overland Chief from Chicago to Seattle was not being honored because of...

Gay
1 year ago
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Dressing room fun with my mom

This is a story and all over 18.My name is Jess and I’m 23 and this story of the day things between me and my mom when we want shopping together.Frist let me describe myself, I’m 5’9 slim but in shape, I have a bubble butt witch both guys and girls like and 40 f breasts and guys and girls love to look at them when I wear bikini tops and small tops and I always have a shaved pussy too.Now let me describe my mom, she 5’7 with a plump body and she is 45 years old, she has big breasts too and I...

4 years ago
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Dressing to Please my Son

Jenny had been divorced for about three years now and hadn't dated much. She owned a small but comfortable house where she lived with her two c***dren, Tony and Debbie. Debbie was 19 and away from the house often, partying with friends. Tony was 18 and spent more time in house than his sister.Jenny hadn't dated much since the divorce and when she did it usually left her feeling unsatisfied. She was beautiful with her red hair and fantastic, 50 year old body. She had rather muscular legs, curvy...

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