Mother's Sissy, Teacher's Pet free porn video

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Mother's Sissy, Teacher's Pet By Sandy Brown January 15th, 2012 Dear Ms. Brown, I am Sandy's homeroom and science teacher. I thought I would mention to you that I noticed that Sandy had a small amount of nail polish on the base of his fingernails today. I assume that he was having some fun with you over the weekend, and that before he left for school you used nail polish remover, but inadvertently left some polish on. The color is very pretty, and I'm sure he looked adorable, but I was letting you know about the oversight because I'm sure you would not want him to suffer any teasing from his classmates. Warmest regards, Susan Findley January 16th, 2012 Dear Ms. Findlay, Oh, my! Thank you so much for your email, and your understanding tone! Yes, your supposition was correct. I was doing my nails this weekend (I know, so old-fashioned of me - everyone else seems to go to one of the innumerable nail salons in town; I will confess that I get some pleasure from shaping, buffing and painting my own nails!) and Sandy seemed to be paying quite a bit of attention. I couldn't resist teasingly asking if he would like me to do his as well. Imagine my surprise when he agreed! But I was so glad he did; we had such a fun time all weekend parading around the house with our matching nails! I know he is at an age where the last thing most boys would want was to be matching anything (let alone nail polish!) with their mommy, but he did seem to really enjoy it! And it was all just innocent fun! Anyway, should we have another 'girls' nail session' in the future, I will be extra careful to make sure ALL of the polish is off before school! Thanks again for being so kind and understanding, Best, Dee Dee Brown January 17th, 2012 Dear Ms. Brown, Your Sandy is such a sweet, precious, gentle boy; I can totally imagine him having a great time with his pretty pink nails! I think it's such a shame that boys like Sandy can't get more of an opportunity to express their more, umm, sensitive side, don't you? He is lucky to have such an understanding mother! I do hope you get to have more 'girlie' sessions in the future! Fondly, Susan January 17th, 2012 Dear Susan, An understanding mother, AND an understanding teacher :) And please call me Dee Dee! Warmly, Dee Dee January 27th, 2012 Dear Dee Dee, Someone smelled awfully sweet in class today! I don't think it's a problem, but just letting you know that it was noticeable! Fondly, Susan January 28th, 2012 Dear Susan, Oops! I gave Sandy a bath last night (yes, yes, I KNOW he is too old for me to be giving him baths, but sometimes I can't resist treating him like my baby!) and afterwards I couldn't resist putting a little of my perfumed body powder on him. Don't you just love doing that after a nice relaxing bath? He smelled heavenly! I guess I thought it would have worn off overnight. Anyway, if I can share a secret between 'us girls', I'm not sure I will be dusting him with my powder again anytime soon, because, frankly, PART of him seemed to be enjoying it just a bit too much, if you know what I mean.... Xoxoxo Dee Dee January 28th, 2012 Dear Dee Dee, Oh my, I can just imagine! Even boys who are a little girlish, well, at that age, every little thing seems to be so, umm, stimulating! I'm sure you handled the situation with aplomb! Fondly, Susan February 12th, 2012 Dear Susan, I am writing you for a little advice. I am DYING to get Sandy's ears pierced! I just think he would look so adorable with a pretty pair of earrings in his delicate ears. I would keep it simple and subtle for school, just a pair of gold studs (but I would be lying if I didn't admit that I picture him with a pretty pearl in each ear!) What do you think? Would it be a problem for him at school? I love my pretty boy, but I do not want him to be picked on! Xoxox Dee Dee February 13th, 2012 Dear Dee Dee, So nice to hear from you! Earrings for our pretty boy? Oh, I think it's a LOVELY idea! To be honest, I think it is possible that he may encounter a bit of teasing. But my experience has been that that dies down after a few days, when everyone simply gets used to the fact that one of the boys is wearing something a bit girlish. Has he expressed an interest? Love (lol, someone had to go first!) Susan February 14th Dear Susan, Speaking of love, Happy Valentine's Day!! If you have someone special in your life, I hope you two have a great day. Anyway, thanks for your email! Although almost all of my earrings are for pierced ears, I do a have a few pairs of clips. I walked in to my bedroom the other day and found Sandy playing with a pair of my mabe pearl clip-ons. I gave him a big hug and asked him if he would like to have his own earrings, just like Mommie. He got very shy and didn't say anything, but he did nod 'yes'. Ok, I think you have given me the courage to go ahead! I will keep you posted! Love, Dee Dee February 15th, 2012 Hi Dee Dee, Happy belated Valentine's Day to you too! No, there is no one romantic in my life at the moment. LOL, sometimes I think I might end up as the stereotypical spinster school marm! How about you? Sandy never mentions his dad.... Love, Susan February 21, 2012 Dear Dee Dee, Well, I see that you did it! Thankfully, Sandy's new earrings were a big hit with most of the girls in the class, who of course noticed right away. I have to be honest and tell you that some of the boys were making fun of him, calling him a sissy and talking to him in a lispy voice, but I tried to put a stop to that right away. Before he went out for recess, I kept him back for a minute and talked to him privately. I told him I thought he looked very pretty with his new earrings. (Yes, I used that word intentionally; I wanted him to know that it's ok for a boy to be pretty!) I also told him that sometimes kids (especially boys) could be mean and stupid, and he should just ignore anyone who was teasing him. He hugged me and thanked me. I tried to keep an eye out in the playground, but as far as I could tell, he was just hanging with the girls and they seemed to be very friendly to him. If there is any more trouble with the boys, I will let you know. Love, Susie PS I do think it is good that you kept him with simple gold studs. Have you gotten him anything more fun for home? February 22th, 2012 Susie, Thanks for the report! I was very nervous all day! I guess a little teasing by the boys is only natural. Sandy didn't say anything about it. He did say that lots of the girls liked his new look. In addition to the gold studs, i did get him a pair of pearl studs and a pair of small gold hoops. I would love to get him a pretty sweater set to wear with the pearl earrings! I would also love to get him some more fun things, including a pair of big hoops and some dangly chandeliers! Oh, my, I hope I don't get too carried away! Please tell me if I do!!! Love, Dee Dee PS. The only romance I have in my life is my beautiful boy, who bought me the most darling Valentine's Day card! Sandy's father has been gone for a long time....He was a mistake that is only mitigated by the fact that it resulted in my son.... March 1, 2012 Dear Dee Dee, The sweater you dressed Sandy in today looked so yummy and soft that I couldn't resist running my hand over his back to feel that cashmere. Imagine my surprise when I felt his training bra underneath!!! Dee Dee!!! You naughty girl! How did you get him in a bra?? Xoxoxo Susie March 2, 2012 Susie Dear, Can I miss you even though I have never met you? We might have to rectify that situation! Anyway, how did I talk him into it? Well, I didn't! I had gone out the other day and picked him up a few things in the girls department, including a few training bras. Yesterday, when he was getting ready for school, I told him I had some clothes for him. I gave him the cashmere sweater, and for under it, a sweet white cotton blouse with a Peter Pan collar. Before he put that on, I handed him the training bra and just said, "Honey, this goes under your blouse. Let me show you." Very matter of fact, like there was no choice in the matter. I love the fact that he is so obedient, and will do whatever Mommie says! I just have to remember to pay attention to his gym schedule! Love, Dee Dee March 9, 2012 Dee Dee, Love Sandy's new haircut! I think a bob is very flattering for him. When I complimented him, he told me quietly that it looks just like yours! I am so curious, my Dear! BTW, I also noticed the eyebrows. Very nice - not too much, but the thinner, shaped brow really brings out his eyes! Love, Susie March 10th, 2012 Susie Q, Oh, I had such fun taking him to my salon! I'm so glad you like his new hairstyle and brows. Of course I was thinking of you, hoping you wouldn't think I had gone too far....I know it is naughty of me to have too much 'Mother-Daughter' time with Sandy, but I just couldn't resist! After we had our hair done together, I just had to take him for a mani- pedi! I took the polish off of his fingernails before school, but left his toes done in the prettiest pink! Love you, Dee Dee March 17, 2012 Dear Dee Dee, I wanted to let you know about Sandy's day today. During recess, Sandy was, as usual, hanging out with the girls (He really spends no time with the boys anymore. I think it's just as well....) Anyway, it seems that one of the 'faster' girls in the group had taken her mother's lip gloss, and this group of girls was taking turns trying it on. Since it was on the playground and not in the classroom, I chose not to say anything. Anyway, it was Sandy's 'turn' and he tried the lip gloss (a noticeable, strawberry frosted shade) on just like the 'other' girls. I remember when he came in the first day with his earrings, the girls kind of made a big deal out of it. But now, it was just like he was one of the girls. They all came back into the classroom wearing their lip gloss. I wasn't sure what to do. I finally said that, at eleven years old, they were not allowed to wear makeup in class unless their mothers gave permission. And that in my opinion, lip gloss counted as makeup. One of the girls said, "Does that include Sandy?" And there was some giggling. I said, "Yes, no makeup for girls OR boys without their mother's permission!" He was a little embarrassed, but I suppose if he was overly sensitive to the subject he would not have put the lip gloss on in the first place. I had them all take the lip gloss off, but you should know that he looked prettier than any of the girls! Oh, I just wanted to hug him to death! Love, Susie March 18th, 2012 Susie Q, Oh, I don't know if I should admit this to you, but when I read your email about Sandy wearing the lip gloss, it made me a little hot! I am not sure WHY it turns me on to think of my son turning into a feminized sissy, but it does...and I do not know why I feel like you would understand, but I do...oh, I HOPE you do! So, I have been getting up my nerve to ask you this....would you join Sandy and me for dinner at our home on Saturday night? I know that it is probably not totally appropriate for a teacher to be eating at her student's home, but I am hoping that you will make an exception in this case.... Kisses, Dee Dee March 19th, 2012 Dear Dee Dee, I thought you'd never ask! Of COURSE I would love to join you and Sandy for dinner! How shall I dress? Love, Susie March 19th, 2012 Dear Susie, Oh, wonderful! Sandy and I will both so look forward to it! Dress? Giggle, wear something sexy! Xoxoxo Dee Dee March 23rd, 2012 Dearest Darling Dee Dee, Where do I begin? With that delicious good night kiss? That was the first time I have ever kissed a girl! Can I just say, "yum!" Or should I start with Sandy? I LOVED what you did with him! The combination of dressing him younger than his age, and then putting makeup on him, was, well, hot! I had been wondering what he would look like in a dress, and wondering if you would dress him like a girl for dinner, And I was so glad you did! The burgundy velvet dress with the white lace trim was adorable! And the white tights and black Mary Janes were perfect! And i loved the matching hair bow and pretty little barrette you put in his hair! So perfect with his pearl earrings! But having him dress like a little girl, and then adding blush, mascara, pink frosted lip gloss and even some pretty blue eye shadow was just perfect! I think pale pink lipstick and a little blue eye shadow is just perfect for dressing up a younger girl for a special occasion! When you wrote before that having your son become a sissy turned you on, to be honest, I was not sure that I followed. But after seeing him last night, oh, I do, I do! I'm sure that now that you have experienced the pleasure of dressing him this way, you are just dying to keep him in dresses! And I must say, once he got over his shyness at having me see him like that, he seemed totally comfortable dressed that way. And such a little lady, with his knees pressed together! I love the way he plays with his hair, absentmindedly pushing it behind his ear, just like a little girl! I know it will be hard for you to put him back in boy 's clothes for school, but, at least for now, that seems like the right thing to do. Next time, dinner at my house. Come to think of it, how about a slumber party! Are you two free next Saturday night? I'll bet Jamie would love to try different makeup and hairstyles! I have a guest room that he could use, and well, a king sized bed for you and me... Love, Susie

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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

3 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

3 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

1 year ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

3 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

2 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 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 School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

1 year ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven 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 brother.) James: AKA. Auntie...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

1 year ago
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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...

3 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...

2 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...

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