Young Sissy Brother/Son free porn video

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Young Sissy Brother/Son It was the first day of summer vacation. Fun to say the least! Then I heard my younger sister, the brat, yelling at me. "Why don't you want to play with me? I have all my dolls set up to have a tea party and I need another person to help." "Bree, I don't want to play with you (ever) and your stupid dolls. You're 12 now, so act your age." "My dolls are not stupid. Mom, mom, can you help?" "Kids, I'm already late for work and I can't have you two fighting all summer. I will not allow this to happen. Understand. Alan, you could play and help your little sister say for an hour or so, Ok, honey." I hate when my mom calls me "honey." She will expect me to corporate and if I don't, the "honey" niceness quickly changes. "Ok, Ok, just an hour. 15-year-old boys don't play with dolls, just for your information." "Thanks Alan. With your dad traveling this week, I will need your help. In Bree's bedroom she had all of her dolls arranged around a doll table with tea settings in front of each doll. Ugh. "Ok Alan, you have these three dolls, and you are so excited to be invited to your first tea party. Now tell me what each one is going to wear." Ugh. "Bree, this is so stupid. I don't want to dress your dolls for your tea party." "But you told mom that you would play with me." "Ok, Ok, just for a few minutes." "Now, how will you dress Angel, my favorite doll?" "With her blonde hair, I would have her undergarments be black. And then I would have her wear a red dress." "Oh, Alan, I think you have an eye for fashion. How do you know so much about colors and fashion?" "Uh, I don't. I guess I just watch mom and other girls and see how they dress. It is not rocket science." "Hmmm, Ok, if you say so." The two kids played nicely for a while, and then Alan decided he had enough, so he left to go play video games in his room. Bree was upset. She vowed to get even with her brother and force him to play more with her this summer. Hmm, she had to think of someway to have leverage over him, to make him do what she wanted. He does seem to have an eye for fashion, maybe he likes women clothes, she giggled. As Bree was putting away the laundry, one of her household tasks, she noticed that a pair of her panties were stuck to some of Alan's sox. Oh, that's funny. My panties ending up in Alan's sox drawer. Then it hit her. I could blackmail him. I could tell mom that Alan took, no borrowed, a pair of my panties for who knows what! Yes, that's it! At dinner that night, Bree mentioned to her mom that they needed to talk. "Oh, ok, Bree, sounds serious." "Well, how do I begin. Mom, I think Alan really liked playing with my dolls and I found out that he knows a lot about fashion. He told me that he watches you and other girls and how they dress!" "Really!" "Yes, and, and, what I wanted to share with you, is that someone has been in my things, my clothes! They are not how I left them, and I think I'm missing a few items!" "Oh, I see. Ok, well, let me think about this. I may have to talk with your brother about leaving your things alone." The next day Alan was taking a shower in the morning, so his mom had an opportunity to quickly look into Alan's bedroom. As she lifted the mattress, she was shocked to find a pair of Bree's Barbie doll cotton panties! OMG, Bree was right about Alan stealing and then probably wearing girl's clothes. I wonder if he has been in my things. I better pay attention. Anyway, what do I do? Just then Alan came out of his bathroom. "Mom, gee, what are you doing here. I'm not even dressed!" "Alan, we need to talk. Bree shared with me that someone has been in her things, her intimates. And now I found a pair of her panties in your room!" "Mom, mom, you have it all wrong." "Mister, I don't think so. And now I want to you go and give Bree back her panties and apologize and tell her you will not take or wear her things again, understand." "No, now! I mean now!" I had no choice. I could see the smoke coming out of my mom's ears. With my towel wrapped around me, I took Bree's panties from my mom and walked down the hallway to my little sister's room. Bree, of course was all smiles. I hated her even more. "Yes?" "Here are your panties." Oh, cool. Thanks" "Say, if you ever want to wear them or borrow anything else of mine, just let me know, brother." I could have killed her right there. At breakfast mom reminded us to be on our best behavior today and not fight, or else. "Bree, what are you going to do today?" asked my mom. "Sara is coming over today. She has a new makeup kit, and we are going to try some new looks and things. It will be so fun. And Alan, you could join us if you want. With Sara being the cutest girl in school, I'm sure you love to spend some time with us." "Bree, no teasing and I mean it. Ok, I'm late again I need to go. And Alan, behave yourself." Sara was the cutest girl in junior high. She was 13, a year older than Bree, but Sara looked 16. Every boy was shy around her, even the older boys. Alan did sorta wait around till Sara appeared at their front door in the afternoon. She had a large makeup kit with her. It looked heavy. Sara, with her sparkling eyes and cute smile, asked Alan to help carried her makeup kit upstairs to Bree's bedroom. "No, problem Sara. I can do this." After about an hour, the girls took a break and came into the kitchen for a snack. Alan of course was still "hanging around ." "Oh, hi Alan. I was hoping you would still be here," said Sara. "I need you would do me a big, big favor." "Sure, what do you need." "Well, it's kind of embarrassing, but I want to try three new lipstick glosses. Would you mind if I kiss you three times?" (Kiss me three times)!!! "Yes, each time with a different shade, Ok." "Yea, sure, I could do that." "Great, let's go upstairs then." Alan followed the two girls upstairs like a little puppy looking for a special treat! In Bree's bedroom, the girls had makeup items spread all over the room. "Alan, please sit here down on the floor." Sara applied some lip gloss to her lips and then kissed Alan each time with a different gloss. Alan was in heaven. Then Sara wiped her lips clean and applied a deep red lip gloss to Alan's lips! "What, what are you doing?" " I want to see how it feels and tastes from a boy's point of view. Relax, Ok." Sara then kissed Alan again. What Alan did not know, was that Bree took a pic of Alan with his lips painted a bright red. After the kiss, Sara wiped Alan's lips clean, but did not do a very good job of it. Later in the day, June (mom) finally comes home from work. She quickly noticed Alan's lips. "Alan, what is on your lips?" "Nothing, oh ya, Sara kissed me with a new shade of her lip gloss." "Really, Sara kissed you!" "Mom, that did not happen," injected Bree. "Sara and I came back into my bedroom after a break and we caught Alan trying on lip gloss. I even took a pic. See." "Alan, how do you explain this picture? Hmmm." "Bree is lying, that's not what happened." "Oh, I see the lip gloss just appeared on your lips. Anyway, why don't you go to your room. I need some downtime. I will deal with you later, young man, or should I say young lady." That was it, I spun around and stormed to my room. My sister is going to pay for this I said to myself. As June took off her work clothes, she did notice for the first time that some of her things had been handled. Both her clothes and her lingerie! Yikes, what am I going to do with Alan? His dad will kill him. June decided she needed a strategy and a plan to help her son. That night she looked on the Internet. All the answers and solutions were about "Petticoat Discipline," where you correct a young boy's interest and desire to wear and experiment with his mother's and or his sister's clothes by indulging him so he eventually tires of the "game." Well, I don't want Alan to wear my clothes. And since he is only 15, he is closer to his sister Bree. Yes, Alan should be a tween before a teen. In fact, maybe being a tween for a while will embarrass him more. I sure hope so. Now, how do I proceed? How do I get Alan to wear some of Bree's clothes like a tween? At dinner that night, June announced some major changes for the family for the summer. "Children, we are going to have some new rules for the summer. I don't want to come home every day to find you two arguing, so starting tomorrow each of you will be in charge of the other (completely) for half of the day. Even if you have friends over, you have to do what the other one says. No arguments or disagreements. Understand, or there will be severe consequences." Both kids were thinking about what they would make each other do when in charge. June had already spoken with Bree, who was to implement June's plan to feminize Alan like a tween! Alan announced that he wanted the mornings when it was nice and cool outside. In the morning then, Alan had Bree play outside games with him. She wasn't very good, but it was fun teasing and making fun of her. After lunch, Bree announced now it was her turn and that she wanted to play dress up. "What?" "Dress up. You know, we try on different thing's and act (girly)." "Like what kind of things?" "Come up to my room little brother and I will show you." To be continued...

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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

2 years ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

2 years ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

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