Sissy Therapy free porn video

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My advertisement read: MEN Interested in sex with other men but don't know how to proceed? Looking for a safe, friendly way to find out if this is for you? Obsessed by online bi/gay/sissy/crossdressing porn but frightened to meet someone? Is your marriage at risk because of your desires? I can help! One four-hour sexual therapy session will help you to decide if this is right for you, and will help you to understand your desires. Don't suffer alone, I can help! Email [email protected] or call 555-252-5252 and make an appointment today! I was continually short of cash and my dead-end job was going nowhere so I decided to so something about it. I had a small house but it was just me there so it was relatively easy to put in a desk and smarten up a room to make it look like an office. I put in a couple of old armchairs and a box of tissues (people always cry during therapy, or so I had read) and that should do it. I smartened up my bedroom, got a deal on condoms and a variety of cheap lingerie, makeup and wigs, and thought that was sufficient. I had been helping friends for many years with coming out as gay and many more who just wanted to experiment, so it was natural to try to start a business. Where I live there were no restrictions on calling yourself a 'therapist' but obviously I couldn't claim to be qualified in any way, and wouldn't lie about that if asked. Another issue was not to be accused of prostitution of course so I'd need to emphasize the therapy, learn open listening and to let the client talk through his issues with respect to sex and desires. Admittedly there could be a fine line here but I needed to take a risk otherwise I'd be stuck in this rut forever. Still, I'd be doing much of this already for free, so I thought I might as well get paid for it. I've always been a huge believer in wrapping. How something is presented is at least as important as what it actually is. Yes, I looked at book covers, in other words. So it was vital how I came across. I didn't want to go completely fem but I didn't want to appear as a vanilla man either. I decided on an androgenous, non-threatening persona. I had longish hair so wore it down, with a slight curl at the shoulder-length ends, and used clear lip-gloss with just a hint of pink and some glitter, but relatively subtle. I had just the faintest touch of blusher as well. I wore tight- fitting tops that could be seen as blouses or perhaps somewhat feminine shirts and tailored trousers that were a bit clingy to show off my assets. I was 47 when I started so no youngster but then again I wasn't going for teens who were confused about their sexuality. My preferred clientele were married men obsessing about sissy porn, edging themselves for hours every day who needed some sort of resolution. I would be 100% fine if, after being confronted with the reality of the situation they decided to spice up their own married sex lives and I could advise on that. However if they wanted to actually take a walk on the wild side (as Lou Reed would have it), then that was fine with me as well. At least for a few hours. As long as these men admitted to me what they were feeling and, more importantly of course, admitted this to themselves to allow them to move forward. I wasn't a fitness fanatic but I did go to the gym 3-4 days/week so was trim and somewhat athletic looking for my age. I concentrated on legs, core strength and abs and kept arms and chest trim but not overly muscular. I always went for fitness and endurance instead of bulk. This left me with a decent body and because I was careful what I ate and drank, I could get away with almost everything I needed to wear to make myself desirable to either sex. I had no significant other, having been divorced for many years, and mainly had male lovers. I considered myself bi but preferred dressing en femme, and have had a few 'lesbian' affairs with women but always found myself back with men, usually those who also liked to dress up. There's something so erotic about being with another man when both of you are shaved, clean and dressed, and want to take your time with each other. There's such a thrill from introducing men to this sort of loving, to get them to open up, to admit to themselves how they feel, that this business idea really seemed to be a way for me to get paid to do something I loved. The setup costs were minimal so it was worth trying. Advertising was tricky. Gay clubs and bars - not needed! Online? I needed to go where the customers would be. There were so many porn sites that catered for sissy and crossdressing porn that might be ideal so I tried there first, but with ad-blockers and the high prices, it just didn't seem worth it. So I went with my own blogs on Tumbler and BDSMLR to start. I got established by posting sex images then peppered my advertising throughout, maybe every five posts was an advert for my therapy. I couldn't believe the response! Sadly most of the calls and emails were horny men wanting to hook up for a 'date' so I rewrote my advertising to make it explicit that this was a serious therapy business and not prostitution. This got rid of a lot of the timewasters and my website also proved popular (although at first it only had the original advertisement, I was later able to include 'case studies' as examples). It seemed to be happening very quickly but I took the plunge and agreed my initial appointment. At the start I asked for cash only because I didn't know how to sort out credit cards, bank transfers etc, so Larry knocked on the door with an envelope with cash. He was probably mid-50s, decent shape overall but a bit heavy, and seemed pleasant enough. I let him in, offered him a glass of water and we sat down on the armchairs facing each other. "Larry, tell me why you're here." It seemed like a good opening line. Larry immediately looked crestfallen. "It's taken over my life, Shelly. I'm obsessed. For God's sake, I have a wife, two lovely kids, I don't understand it. I...well, it's just like your advertisement. It's all I think about. I even dream about being with another man, dressed up as a woman, and, and..." Wow that was fast. I was happy that I had put the box of tissues in the room and I handed it to him. Less than a minute in and he was crying. I told him to take his time, that this was a safe place and whatever was said here, stays here. I should have probably started with that but I was learning on the job. Once Larry was composed I said, "I understand Larry. It's a tough place to be. Tell me about your marriage and sex life at home. How often do you have sex with your wife? Is it intercourse or more than that? How long do you spend with her?" I thought that would be important to know. "It's been a long time, Shelly. She's accused me of having an affair, of no longer being attracted to her, of having lost all sex drive, I don't know. I just, well, as I said, I'm obsessed. I can't tell her of course, could you imagine?" I certainly could but it wouldn't be an easy conversation. "Last time my wife and I made love it was quick, both of us were quite drunk, and I don't think it was great but I don't remember much of it. It was a few months ago to be honest and we haven't done anything since then. I, uh, masturbate at least once a day but spend hours on the computer in my office. I can't seem to help myself and when I saw your note, well, it's me exactly." Larry looked at me with his big, sad brown eyes, clearly desperate. I briefly thought, 'A bit of willpower would help!' but put it out of my mind. Bad therapist! "Tell me about your fantasies Larry. Are you the aggressor? Are you more submissive with your male lovers in your imagination or do you take the lead? Describe one of your scenarios to me. Use lots of details so I can understand it." "My usual one is that I check into a bland corporate hotel with a small bag. I spend a few hours bathing and shaving myself from the neck down, including an enema cleanse, flowery moisturizer all over and then I put on lingerie and women's clothes, including jewelry. I make up my face, use perfume and put on a wig, usually light brown, down past my shoulders. My make up is a bit heavy and dramatic, almost slutty, with garish red lip gloss. Not like yours...anyway, I get ready, maybe have a glass of white wine while making sure everything is perfect. At the same time my lover has also checked in and is doing the same thing in his own room. Neither of us can pass, we're not feminine looking but we don't care. I don't have a gaff or anything like that but I have a lacy bra with breast inserts." My goodness, Larry's story is certainly detailed. I was expecting something about sucking dick but this is exceptional. "Thank you Larry, the detail is great, please continue." Larry is looking a little uncomfortable so I add, "Seriously, this is just us here. The detail helps me to understand you and how I can best help. This is why I only book for four-hour slots, take your time, there's no hurry at all." Larry's discomfort seemed to have more to do with his erection than his story. "Larry, I can see that you're, uh, a bit excited as you give me the details and that's perfectly fine. Me too. It's totally natural and your story is extremely hot. Just let your erection occur and try not to be embarrassed." I undid the side buttons on my trousers and eased them down over my hips to expose my light blue satin panties with little red roses on the band. My erection was clearly outlined inside the tight underwear. "This is more comfortable for me, as long as you don't object. Feel free to, uh, free yourself similarly if that helps." Larry went silent for almost 30 seconds as he stared at my crotch from his chair. "Uh, sure Shelly, that's fine." He hurriedly fumbled with his belt buckle and fly then pulled his pants down below his tight white briefs. He was hard with a small wet spot at the tip of his erection. He seemed a bit smaller than average but it was difficult to tell. "That will be much more comfortable, Larry. Please continue." I crossed my legs man-style to leave my crotch framed by my legs. Larry managed to drag his eyes up to mine. "Uh, so, yes, we get ready for each other. Neither of us have, well, had an orgasm for at least three days, that's our 'three day rule' we use for when we meet. We always book on the same floor but not always next to each other so one of us has to walk down the hall to other's room. I, well, I always imagine that it's my turn. I'm in a knee-length formal dress with black high heels, pearl choker and matching earrings. I see an older woman walking towards me and I blush as she smiles and even comments on how pretty I look. I thank her and keep walking. I lightly knock at the door and he opens it. I usually call him Nick. Taller than me, thin and muscular, he opens the door wearing a light green dress, strawberry blonde wig, full makeup, and sparkly red shoes. I quickly come through the door and Nick locks it then we stand and just look at each other for a minute. We air kiss and Nick opens the bottle of champagne and we toast each other." "Nick takes the lead, takes my glass from me and lightly traces my face with his fingertips. He compliments me and tells me how beautiful I look, looking at me in my eyes the whole time, then kisses my ear and whispers if I am excited to see him." "This is all wonderful, Larry, I love the scenario. Two quick things - do you and Nick have fem names? Also, have you considered doing this with your wife? Hotels can be great fun, you can be anyone. Or even just the touching you described and whispering. Women love to be treated as princesses sometimes, with loving respect as you describe. Couldn't hurt, could it?" Larry looked confused then said, "Why not? You mean treat her as I treat my imaginary Nick?" "Exactly! Yes. Just like that. The whole buildup isn't so important of course but what matters is how you treat her. It's an easy thing to do." Ah, I remembered my special notebook and opened it and scribbled, 'Treat wife like your fake lover - Larry' to remind me. Then I crossed out Larry and put his name at the top of the page. I was hoping that Larry didn't notice that the book was otherwise blank. "So, uh, then we make love. That's it." I laughed softly. "Not in a million years, Larry. I need to hear it all. From when Nick was whispering. And tell me his and your fem names." Larry blushed and said, "Nick is Nikki and I'm Laurel. Uh, so Nikki whispers to me, 'Laurel, you're so lovely tonight.' He pushes against me and I can feel his, his erection, through his dress and mine, pushing against me. Against mine. He holds me tight and kisses me, gently at first, then his hands move down and he pulls me into him as we kiss, massaging my ass as he rotates his hips slowly. I gasp in his mouth as we slip against each other." I look down and see the wet spot grow as he fidgets in his chair. I deliberately move my hand down and trace my cock with my fingertips and let out a low moan. "Don't stop now, Laurel. Both of you still in your dresses, Nikki pushing against you, holding your ass. Your hard cocks rubbing against each other through the thin layers of your dresses and panties. Nikki kissing you, thrusting his tongue in your mouth. What next?" "Nikki unzips my dress and I stepped out of it. He turned around so I can unzip him and then we came together, wrap our arms around each other. His panties leave most of his ass bare and I knead his globes as he does mine. He licks my ear and says, 'I've been thinking about you Laurel, about your perfect ass, about your talented tongue. I want to suck you, to tease the head of your cock in my mouth, then rub my cock against yours. I want to dribble lube onto your ass and rub my cock up and down your crack. Then...what would you want me to do with it, Laurel?'" I think Larry needed some reassurance as he didn't know if he should pull up his pants and run out of my house or come in his underwear. I stood up and slipped my pants off, leaving on my low heels, showing off my lovely legs (if I do say so myself). I reached into my panties and adjusted my erection so it pointed straight up onto my stomach and smiled at Larry. "Feel free to get more comfortable Larry. Shall we move into my other office?" I didn't want to frighten him more to call it my bedroom but I didn't want to continue my therapy session in the office. Something a little more informal would be good, I told myself. Larry took off his tennis shoes and socks and slipped off his pants then followed me out of the office and to my bedroom. I was happy that I had cleaned up and tidied everything. My king-sized bed had clean sheets and looked pristine. Of course Larry wasn't Laurel and was in his tighty whites and flannel shirt, with me in my panties and blouse. Still, it was more than enough. I sat down on the edge of the bed and patted the area next to me. "Come sit down here, Larry." He was obedient which helped, and he wasn't about to attack me. Thank goodness I didn't have to put up with that for my first patient. Larry sat down and I touched his cheek. "I'm a man Larry. This is real, this is my house, and it's just you and me. You've told me some of your fantasy, you and Nikki. Now it's you and me, two men together in my bedroom, sitting on my bed." I traced his lips with my fingertip. Who knows, he had nice full lips, he might transform well. Good enough anyway. "Do you want to touch me?" I stood up in front of him and peeled off my blouse. I was hairless from the neck down of course but apart from my hair, face and panties, I was definitely a man. "Do I turn you on?" I took his hand and put it on the front of my panties, over my hard cock. "Is this what you want really, Larry? Or is it all just pretend? Is this too real for you?" I quickly took off my satin panties and kicked them across the room and stood in front of Larry, completely nude, my cock sticking straight out, angled upwards. "Do you want to touch it?" Larry seemed nervous but I let him make the first move. He hesitantly reached out and took my shaft in his hand. "That's it, touch my penis Larry. Do you like it?" "Yes, Shelly, it's hard but soft. It feels so warm, almost hot." "At long last, after all that time obsessing over videos, your first cock. Feel it all over, feel the head. Hold my balls in your hand, Larry. You like? Does this turn you on? Or would you prefer a warm, wet vagina, attached to a lovely pair of breasts?" So much for my therapy, having Larry choose. Given the choice myself, naturally I'd have both. Poor man... Larry's answer was to learn forward and take the head into his mouth and run his tongue over the spongy head, then all around until concentrating on the underside. Oh boy, for a beginner he definitely was turning me on. "Oh, Larry! Yes, suck me, suck my cock. Yes, your first. You have my penis in your mouth. Think of that, Larry. What does that make you?" Larry slowly withdrew the head from his mouth, a line of spit forming then breaking as he pulled his head back. "Shelly, I'm a cocksucker. I'm a sissy faggot." I pulled him up and savagely kissed him, rubbing his ass. "Larry," I whispered in his ear as I ground against him, "does it turn you on when I call you a fag? A sissy cocksucker? Tell me..." I pushed him down on the bed and took off his briefs. "Oh Shelly, yes it does. I think this is part of the attraction, to do something dirty, forbidden. I know it's not really like that, not anymore, but it feels that way. I like the humiliation, the, the...compulsion no matter how dirty it is, the pure lust, the..." "Lick my ass, Larry. Start at the crack and work your way down." I quickly got on all fours and Larry got behind me, following my instructions. My orders. "Yes, good boy, get your tongue in there. Did you know that you'd be licking a man's ass today? Working your way down to his rosebud, his anus? Keep licking, Larry." He was doing a good job, lots of spit as he worked his way down. "Now tease me Larry, run your tongue and thumbs around the hole, ahhh...yes, oh! - now push your tongue in, yes. Musty, Larry? Your tongue up my ass? Does this still turn you on or are you disgusted?" Larry stopped licking for a few seconds. "I've never been more turned on, Shelly, it's like I was born to this, it's better than I ever imagined. So dirty, so, ohhh..." and with that he pushed in again. I guided Larry down to my balls where he lovingly sucked each one. I thought, yes, my therapy worked, this man is definitely bi if not gay. Maybe just bi and men are new to him so he's going a bit nuts? Whatever. I wondered if it would always be this way, if my advertisement was self- selecting, if everyone was at least partly bi. Then I stopped musing as Larry started sucking my cock. He did a decent job as well and I made him swallow my cum. I told him that sissies didn't suck and spit, they craved cum, the taste, the smell, the feel. That it was his reward for turning me on so much that I couldn't help but give in to his sexiness, his allure. Not to mention my cock in his mouth. Afterwards I got him on all fours and lubed up his ass for a thorough massage and teasing session. Anal wasn't going to happen this time with Larry so I worked a finger or two in his hole, talking to him about being ass-fucked, then pulled his legs over his head and jerked him off into his own mouth to finish. A satisfied customer! We took a quick shower together and we had a short talk. I convinced him (using my notes! Well, my only note...) to do most of the things we did today with his wife tonight. Spend time tracing her face, her body, suck her toes, tease her thighs then roll her over and rim her ass. Don't even consider your own pleasure, I emphasized, just concentrate on her tonight, and make sure she comes many times. Don't even bother to fuck her unless she insists after she's come at least three times. I asked Larry to phone me the next day and he dutifully did. Said that he was up half the night with Denise. He told her that he saw me (and he told Denise that I was a therapist, didn't go into more details) and understood what was missing from his marriage. I didn't see Larry again but we exchange messages once in a while. He's more deeply in love with his wife than ever and once a week he dresses up and they have a lesbian night, complete with a strap-on for Denise to use on her husband. Larry managed to meet a few men through a local bar and has a few one-night stands to satisfy his cock desires. So far he hasn't told Denise, but is working his way up to suggesting a threesome, all of them dressed as sissy sluts. It's nice to have a positive outcome for your first patient. There's been many more since then, please let me know if you're interested in their stories! *** Love, Lyon xxx

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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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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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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...

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...

3 years ago
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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...

2 years ago
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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
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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
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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
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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
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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
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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
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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
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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
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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...

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