Sissy Night At Brucy's free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
• We moved into auntie’s place, who is desperate for sexual relief, she being single. Dad discovers me dressed in auntie’s clothes and makes me fuck the neighbor and more. I am still in college and have friends who think outside the box.
• This happens on a Friday morning and I stay home for the weekend to pleasure Harry our neighbor, who loves my dressing and looking gurly. Daddy thought my long blonde hair to my waist was sexy, and with my plump butt, skinny by some opinions, was perfect hand material for Harry to caress since I was a young person. I grew up and now being 18 was a bit taller and would fit into aunties lingerie like we were the same size. Once I started to visit her drawers on a regular basis, I had more regular orgasms that made me want more. Her panties were so soft and silky that I would get hard just thinking about them, kind of like being in love with my auntie. And knowing how I could feel her through the smell of her body left on the lingerie I could tell she was hot; she wanted the highest form of sexual passion that she could get. Even though I knew I would be an easy lay for Harry, I hoped that I could tease him and maybe her into an extremely high and hard state that we all would be happy about. Daddy got sidetracked about young boy sex and his sister, my auntie was about crossing the gender boundary, they did this with Harry. She was bisexual from her c***dhood, and I was also in that path knowing that sucking a cock was just as pleasurable as sucking a pussy. My auntie loved her pussy to be sucked and licked, especially by a male, her nephew, who wantonly lives the other side of being a male, near the female view of seeing the world of sexual satisfaction. To be penetrated is the first thing, pretty much, and then how does one enjoy the friction between the probe and the enclosing human flesh. My butt was never the same after Harry and Daddy made me their queen by getting off in my ass, and making me love it, as they kissed me deeply and made me suck their lips and taste their cum as he fed me his cock covered with his cum from my ass, breeding me in a sense. The three of us had many orgasms together and ate freely of our fluids, aunties smell made me grovel in the a****l consciousness of base human sensory awareness she tasted so good. We used to sleep together in bed and wake up in the middle of the night with our hardons poking each other in various places. I loved getting fucked in a sandwich with Auntie giving me her luscious tits to suck on and Harry and Dad fucking my ass till I would cum on Aunties stomach, lick it off, and share some with them all. She was always ready to then sit on my face, so I could tongue fuck her pussy and swallow her juices running down my throat.
• One day Auntie was home alone, and I came home from college unannounced and found her dressed in lingerie watching a lesbian porn video while getting herself off. She heard me coming in the door and shouted out to come in to her bedroom where she was splayed on the bed with a big dildo up her pussy, moving her hips in rhythm to the music on the porn video. I looked at the screen and saw two trannies getting flogged by two mistresses with some short whips that were making their asses framed by their pulled down panties red. Auntie said, “Nephew, would you be my tranny slave, can I dominate you into submitting to my deepest darkest sexual depravities?” I nodded slowly as I looked at her watching the video and getting off on the idea of her being in command. I needed her to lead me into the depths of her desires, unbounded by societal norms. I was also looking to be released from our constricting norms, especially when it came to crossdressing, I so wanted to crossdress with my friends from college, it would be so fun to party with them. Maybe they would be interested and maybe Auntie could make us all submit. Auntie could see the wheels turning in my head, she suggested that we get a shower and wait till my father came home. After my shower Auntie called me into her room, she said, “I have a sexy outfit I would like you to try on, it was a maid uniform with stockings, girdle, bra, slips, and ruffled skirt and heels. I was drawn to the garments laid out on the bed. Auntie said I first had to go back into the shower and shave all my body hair off as close as possible, especially on my face. Once out of the shower she powdered me and put on some body lotion which made me smooth. Then she had me put on the lingerie and sit so she could make up my face. I loved the look as she gave me a feminine workover and then a blonde wig, with long curly locks. Once this was finished, came the blouse and skirt, and heels. They were high, I had trouble walking in them. Then she gave me a duster and said, “ok sweety, time for you to do the chores, start cleaning and don’t miss a surface your father will be home any minute and I want the place clean.
• After a while I got into it, feeling like a sexy slave that is taking care of his aunty. My mind was drifting in the sexual delirium of the moment, until I heard the front door open. My father was standing there with an open mouth, big eyes, and a smile from ear to ear. He acted like he saw his dream c***d. Coming into the living room, my Auntie was sitting on the couch sipping her martini and looking through glamour magazines. She saw my father and smiled and said, “brother I hope you like what you see,” my father nodded affirmative, he responded with, “where did you find her, she looks beautiful, kind of makes me harden up a bit. Auntie said, “don’t you recognize her, she is from around here”, my father took another look. Then he had the look of cognition and came over and kissed me deeply, knowing I am his son but not knowing the whole deal.
• Dad put his things down and asked Auntie what is up for this weekend. She said, “Brother I have a proposition for you, knowing how you love to taste the extreme side of sex in an orgy setting. I have invited your son’s four college friends and Harry over for the weekend and I am going to be your mistress who will have my way with all of you at once, how about that?” Dad looked at me we both smiled like we feel into the candy shop and wondered what events we were about to jump into. Auntie told my dad to go shower and shave everything neck to toe. He wandered off to carry out his tasks.
• Auntie told me to call my friends over and go over and get Harry directly. Well this was easy to call my friends, I simply texted them in a group text. “Guys, up for some tranny orgy fun with my mistress aunt this weekend, come over dressed and ready to stay.” They all affirmed in 30 seconds, and then I was off to Harry’s who lived 4 doors down on the same side. I pass Joanne walking down towards my house, Auntie’s friend who looked at me real hard, trying to understand what male is dressed as a tranny. Our eyes locked and then we were past each other, I did not get called out on the charade, good thing. I arrived at Harry’s and knocked on the door, there was a long delay and I finally her him opening the door. He looked out and saw me fully dressed and intuitively knew it was me. Oh, my sweet Brucy, some right in, and I ran into his house to get out of the street, hoping no one would see me. Once inside I got a full view of his outfit, which was kind of old lady like, he was dressed in skirt, stockings, low heels, white blouse with ruffles, large boobs, wig, and makeup. I said, “when did you start dressing like this, I love your outfit.” He said, “when I was about 10 I got into my mom’s clothes and started getting off on dressing like a female.” I have been doing it for 50 years since then, and love it as much as I can get, but I do not go out.
• He looked me over and said, “your dada had told me you were into crossdressing and I see you look genuinely nice and it fits you and your build and personality. “How was it coming over to my house?” “Well, I passed Joanne from across the street and she gave me a hard stare trying to recognized me but she couldn’t.” Harry said, “Oh that old lesbian has been trying to see what her neighbors have been up to forever, I see the females who visit her house, they are always well dressed and have on sexy outfits. They come in and then leave after several hours. Occasionally she has a weekend party, and they stay all weekend, never any males though.”
• Then I knew why she was looking at me, she wanted to see if she could hook up and suck my pussy, which would have been fine with me. Anyhow Harry and I were to go back on the street dressed in our tranny outfits, to go back and get with Auntie. Harry brought a bag full of stuff and out the door we go, as soon as we turned toward my house, who is coming the other way, but Joanne, she was about 500 feet up the street, just about past my house and in the dim twilight she was staring at us two real hard. We slowed a bit but kept moving, looking like a couple of whores out for the night, giggling about something we were about to do or say. Joanne got about 50 feet in front of us and she blurted out, “Harry that is you, I can’t believe what I am seeing, you look cute all dressed up, kind of like a 2 bit whore, but I like the look. And who might you have walking beside you down this street, do I know you too?” I looked away hoping she would drop the issue and no she did not. We got to about to cross her path and she stopped us and wanted to know who I am and then she recognized me, “Brucy, I can’t believe what I am seeing, you look cute and sexy in that outfit.” When did you start dressing, it looks like it becomes you?” I felt like melting right into the sidewalk and a side effect was that my cock was getting hard in my panties covered with my girdle. She then started to go on about how society was loosening up and men could dress however they wanted these days without any repercussions from anyone else, Harry and I both agreed heartily and said, Thank you for the recognition and enjoying our interests as much as we do, we thought you were going to call us out and ridicule our dress and report us to somebody, don’t know who.” She said, “oh no, I fully support men who crossdress they get to feel like I do with more, they have a clitty that is bigger than mine, and an ass pussy that can get filled like my pussy, just they can’t have k**s, not that I want any.” Harry looked over at her and said, “you look pretty good yourself, the years have kept you well, I also notice that you have quite a few girlfriends that come by to see you, and Joanne blushed and got shy. “Well you know I am interested in girly things, but more as a female, I am like a female sissy, I love all aspects of feminine clothes, lingerie, and loving a female, guess you could say I am a submissive lesbian and all those girls you see come over are my mistresses who have learned to dominate me in my house. They make me do the dirtiest things to please them and I willingly oblige them with enthusiasm. If they make me scrub the house, I am on my knees, hopefully looking up their skirts and seeing their pussy through their nylon panties. I dress in a maid’s outfit like yours Brucy, and have to be very careful not to rip my stockings otherwise I will get a sever whipping, which I love by the way. I crave the feeling of letting go and swimming in my mistress’s desires for me.” Well, Harry and I were taken back for sure, we never expected our little neighborhood walk would be getting intimate with another neighbor.
• Harry looked at me and said, “Joanne, you are so precious in that you shared your inner secrets with us so willingly, we thought you might want to join us at Brucy’s house in about 2 hours or so, you will like the party from what you have been telling us. Why don’t you come over, and dress in your best submissive garb, you will need it.” Joanne looked surprised and nodded that she would see if she could make it, and off we went to our respective houses. Harry and I arm in arm on our way to a sexual playground and Joanne alone to get ready.
• Once back to my house Auntie was all decked out in her mistress outfit, she had on mostly black, pvc, with big boobs, zippers in all the right places, a hood that accented her head with a pony tail out the back. He high heels were high, and fishnet stockings extended down from her PVC outfit to her toes. Harry and I were excited to see how she looked, so much different than when we left. I said, “where is dad, is he ready for this event?” Auntie said, he is just about ready, sit down and have a drink, Harry went over and kissed Auntie’s hand and knelt on one knee saying he was at her service. Auntie liked this entrance and said, “you will serve for sure, and you better like it, or you will be sorry.” Harry smiled a knowing look, and moaned a bit, knowing that the pain would be a perfect pleasure.
• Dad came down and peeked around the corner, we said, “come out sissy, we want to see your outfit” and out he came from around the corner. He was dressed like I was, in a black maids outfit, frills, stockings, girdle, panties, ruffles, big boobs, wig, pony tail, makeup, and looked ready to suck any cock or pussy put in front of his face.
• Auntie asked Harry and I what took us so long to come back, and we reported about running into Joanne and our intimate conversation. Auntie said, “bonus for sure on your way back, hopefully Joanne will come over, I would like to dominate that bitch and make her learn a new level of submission. I have been ogling her for years and see all those other mistress whores she entertains every weekend, and she acts like nothing is happening and nobody can figure this out.
• A loud knock at the door erupted making us jolt, and we knew it was my college tranny friends that were there, we all went to let them in. Opening the door, we saw 5 people all dressed as females and all looking passable. They introduced themselves, Danny, Billy, Jonny, Pat, and Betty. I said, “you all look so nice, really gorgeous, dressing in your submissive wear, and you brought along Betty, who is she. Danny said, “Betty was hanging out with us at Billy’s where we were getting ready and she wanted to come along. She is a prefect lesbian sissy submissive and we thought she would fit in with us other male submissive sissies at this party. Auntie said, “please come in all, let’s get this party moving.” We all are moving into the living room where on the screen was a video of the last party we had, where Harry, dad, and I were servicing Auntie in many ways. All of my friends felt right at home seeing the video, since they wanted to taste this for themselves.
• Aunty pulled Betty to her and give her a big kiss, open mouthing her with a deep tongue action. This got everyone’s attention as they got warmed up to each other. Betty was swooning in Auntie’s arms the two of them embracing tightly. I was totally enjoying the lesbian sissy scene and was getting hard feeling my decent into the abyss of subservience and submission. Betty too was weak at the knees enjoying her newfound mistress and filling her needs. Auntie pushed Betty to her knees so Betty could lick Auntie’s pussy through the PVC suit, she pulled down the zipper exposing her pussy and let Betty lick for about a minute, Betty was so humble and licking so hard we were all stunned at her submissiveness.
• The four trannies got comfortable and folks started taking off their clothes, when Auntie said, “hold everything, this is my event, I get to tell you what you can do. No action without permission, got it?” Everyone nodded and stood waiting for Auntie to say, “ok Brucy, I want you to undress all of your friends down to their lingerie. Harry, I want you to undress dad and Brucy down to their lingerie.” And we all got to it, carefully exposing the girdles, bras, stockings, panties, and corsets to our group. We were all starting to feel that sexual vibe in the air, the sissies were showing their hard cocks through their panties with more than one sliding of hands along their cock undersides to enhance the sexual tension. I looked over and saw Auntie feeling up Betty’s big tits like she wanted to own them, pinching the nipples thought the bra, making Betty whimper with passion. They both kissed again, and Auntie pulled away and said. “OK sissys’s I want you all to scrub the kitchen floor on your hands and knees using these sponges, and she gave us all a sponge, then the 6 of us got on our hands and knees and started to scrub while Auntie and Betty sat back on a chair to watch. Auntie had her hands in Betty’s crotch feeling her pussy through her panties, which were getting wet with Betty’s juices. We were all hard and started bumping into each other, I hit Harry’s ass with my face and ran my tongue up his crack. Pat hit my ass and did the same, I tried to spread my legs as wide as possible. Jonny and Danny were head to head and decided to kiss each other expressing their sissy selves to all. Billy was alone and started to feel his cock, sitting on the floor to jerk off, and mistress caught this and said, “stop, I told you nobody does anything, even jerking off, without my permission.” You want to jerk off, then come over here and jerk off Betty. Billy crawled over and started to feel Betty’s pussy and turn her on, Betty looked at Auntie and said, “Auntie you are much better than Billy, can I please have you as my lover.” Auntie looked pleased and said, “Danny go over and suck Brucy and Harry at the same time and Billy came over and started sucking us both. This gave me a chance to look at Auntie and she said, “ok you can kiss Harry, but don’t cum yet.” Harry and I both were totally into kissing and having Billy suck our sissy cocks, which were about 7” each into his wide open mouth, he was laying on his back as we knelt on either side of his face. I was getting really turned on and started feeling Harry’s boobs and him mine, Auntie did not say anything, so we kept doing what felt good.
• The others were about finished with the floor cleaning and we knew this would play into our activities of the evening somehow. Auntie said, “ok now I want you all to strip down to your panties, bra, stockings, and garters, keep your shoes on. Then I want you to line up head to cock and sock each other in a large circle, head to cock, eating each other. Harry leaned over and started to suck Billy, while Billy continued on him, I went down on Billy, then Jonny on me, and Dad on Jonny, and then Pat to complete the circle of 6 sissy crossdressers in a circle sucking each other. Mistress said, “ok now that you are joined, put 3 fingers in the asshole in front of you.” We all slowly did this and I felt so full, it was great, I was hoping to get fisted this evening and was very close to it, Jonny’s hands were not so big and I could easily open up to have him in me. Mistress said, “it looks like you all are enjoying this activity, Betty is there anything you can add to make this a memento of an act, and she said, “Everyone kiss and tongue the asshole in your face now, and then fist that asshole, slide your fit up inside that asshole and stretch it wide, feel your hand going up inside that person, make them feel invaded and hit all of their orgasm points, don’t; jerk them off, make them cum with your hand inside them.” We all followed her direction and got our arms up each other’s assholes, stretching and pushing. Mistress then said, “ok sissies, you have done well, and she took her whip and started to beat us a bit, whipping our butts and making us squirm in pleasure/pain. I loved feeling the whip across my reddening cheeks. WE were all ready to cum at a moment’s notice waiting for Mistress to give us the word. She said, “Betty tell them what to do” and Betty said, “ok, cum now and then drink the piss from the cock in front of you.” We were over the top with depravity and thanked her. We all came at once ooooohhhh ahhhhhh, cumming is so good, as we all swallowed the cum into our throats as it filled them up and over flowed down our chins only to be pushed back in our mouths as Betty helped cleaning us up. Then she said, “ok piss now sissies, piss as much as you can piss, and drink that piss, the warm nectar into your mouths, down your throats, moan like you miss it, yearn for it, tell your pisser to fill you up.” We all started telling our pisser, “please fill me, I love your piss, I have wanted this forever, give me your nectar, I want it so bad.” Then Betty started pissing all over us and was joined by Mistress, therefore we cleaned the floor, so it was clean for a pissing party. As we were all pissed out, we were so satiated that we did not hear the knock on the door. Joanne had come over brining two of her lezzy mistresses and they had just let themselves in since no one answered the door. They were standing there smiling and enjoying the fisting action and pissing, feeling their pussies, and making Joanne kiss them. Auntie looked over as she had finished pissing and said, “Well you are just in time for chapter 2, stand by.”

Same as Sissy Night at Brucy's Videos

2 years ago
  • 0
  • 173
  • 0

The Knight and the Acolyte Book 8 Chapter 9 The Knights Passion

Book Eight: Labyrinth of Love Chapter Nine: The Knight's Passion By mypenname3000 Copyright 2016 Knight Kevin – The Free City of Grahata, Yalut Island The night wore on as we stood our watch in the overgrown Labyrinthine Gardens. The trees and bushes were so thick, the stone buildings of Grahata were completely obscured. There was almost no light, the night sky half-overcast, the moon struggling to shine through black clouds. But our eyes had adjusted to what light there was. The...

2 years ago
  • 0
  • 44
  • 0

Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

4 years ago
  • 0
  • 38
  • 0

Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
  • 0
  • 41
  • 0

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...

1 year ago
  • 0
  • 30
  • 0

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
  • 0
  • 37
  • 0

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
  • 0
  • 44
  • 0

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...

3 years ago
  • 0
  • 41
  • 0

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."...

1 year ago
  • 0
  • 54
  • 0

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...

2 years ago
  • 0
  • 56
  • 0

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...

4 years ago
  • 0
  • 37
  • 0

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
  • 0
  • 36
  • 0

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
  • 0
  • 51
  • 0

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
  • 0
  • 35
  • 0

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
  • 0
  • 37
  • 0

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
  • 0
  • 41
  • 0

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...

4 years ago
  • 0
  • 31
  • 0

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...

3 years ago
  • 0
  • 60
  • 0

Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
  • 0
  • 42
  • 0

Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

3 years ago
  • 0
  • 44
  • 0

Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

2 years ago
  • 0
  • 40
  • 0

Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

4 years ago
  • 0
  • 52
  • 0

Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
  • 0
  • 35
  • 0

Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
  • 0
  • 50
  • 0

Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
  • 0
  • 38
  • 0

Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve 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....

4 years ago
  • 0
  • 29
  • 0

Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

3 years ago
  • 0
  • 38
  • 0

Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

3 years ago
  • 0
  • 41
  • 0

Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

2 years ago
  • 0
  • 36
  • 0

Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

4 years ago
  • 0
  • 34
  • 0

Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

2 years ago
  • 0
  • 42
  • 0

sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
  • 0
  • 35
  • 0

Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

4 years ago
  • 0
  • 31
  • 0

Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

4 years ago
  • 0
  • 56
  • 0

Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - 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; 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...

3 years ago
  • 0
  • 29
  • 0

Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
  • 0
  • 33
  • 0

Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
  • 0
  • 33
  • 0

Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
  • 0
  • 35
  • 0

Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - 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...

1 year ago
  • 0
  • 32
  • 0

Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

4 years ago
  • 0
  • 34
  • 0

Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
  • 0
  • 41
  • 0

Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
  • 0
  • 42
  • 0

SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
  • 0
  • 47
  • 0

Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
  • 0
  • 40
  • 0

Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
  • 0
  • 31
  • 0

Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
  • 0
  • 33
  • 0

Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
  • 0
  • 39
  • 0

Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
  • 0
  • 63
  • 0

Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
  • 0
  • 38
  • 0

Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
  • 0
  • 35
  • 0

Sissy Farm Chapter Eight

Sissy Farm - 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 Jamie, ...

2 years ago
  • 0
  • 57
  • 0

Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
2 years ago
  • 0
  • 30
  • 0

Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
  • 0
  • 35
  • 0

Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
  • 0
  • 32
  • 0

sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
  • 0
  • 25
  • 0

Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

3 years ago
  • 0
  • 36
  • 0

Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine 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...

2 years ago
  • 0
  • 37
  • 0

Sissy Gets A Black Master

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

2 years ago
  • 0
  • 176
  • 0

Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

Porn Trends