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Annie's Super Sissy Idea List!

SweetAnnie40 said:
A couple years ago, my sissy husband and I did a little exercise. We tried to write down every little sissy thing he'd done, anything that gave him a thrill or made him feel 'girly-good', and even everything he fantasized about but hadn't or wouldn't do. I was trying to understand better what he needed and what he desired. I wanted to be warned if there were things I felt were too risky or things I could easily make come true for him or with him.

So here we have the Super Sissy Idea List. I'm taking some liberties to determine when there is a cut-off point where more in a certain direction is really a different fetish and I won't go further into it. Some I think complement 'sissy play' well, others make less sense or Hubby just wasn't interested.

For sissies, you can take this as a massive "Task List" or "Guided/encouraged by a woman task list". Considering the typical conditions you gurls live in (wife doesn't know or approve, not a lot of privacy, etc.), some of these might be out of your abilities but feel free to fantasize about them. I'm not going to go crazy putting these in any sort of detailed order so jump around, pick and choose.

Here we go!

=====================================================
(First Edition: 151 items!)
V1.1 152. (Added E33)
V1.2 154. (Added L10, E34)
V1.3 155, (Added E35)

TO START...

L1. Get healthy. Nothing is sexier than someone who is taking care of themselves. You don't have to become a fitness fiend or drop 50 pounds unless you want to, but use these desires of yours to help you take good care of yourself. You'll feel better and if you're anywhere close to being passable as a female, this will only help. Your partner/family will appreciate it. You'll have more energy and feel better about how you look.

L2. Do women's exercises. You can pick up a Women's Health magazine or cruise youtube etc to see what exercises tone and build a women's body. Men's bodies are different and build muscle differently but I think if you focus on the exercises that firm up your butt, tone your legs, etc. and not the he-man body-builder stuff, it can have a subtle feminizing effect. It has with my husband.

L3. Wear women's exercise gear (under male clothes if you have to). Jog bras, running shorts, exercise leggings, cute sneakers, etc. all make exercising easier and feel sexy.

L4. Eat well. This ties into #L1 but focus on your food. If you want to lose a few pounds, some small changes in your diet can help along with the exercise program. Again, you'll feel better. Even if your wife/SO disapproves of sissy play or doesn't know, she'll appreciate that you're making smart choices and that might pay off in other parts of your life. IF you get to advanced sissy play, having a regular diet and knowing your body will pay off.

L5. See a therapist. You should really try to understand if this is simply a fetish you enjoy sexually or if there are elements of gender, gender role, etc. at play. I don't know much about transgendered journies, what they work with doctors and therapists on, etc. but if that is really your path, you should know that now. Even if you choose to not act on the information, at least it will be an informed choice. Hubby also reminds me that its exciting to tell his female therapist about his adventures/desires while dealing with his feelings and life decisions.

L6. Establish a budget. You don't want sissy play to be a financial problem and it could get pretty expensive depending on how much you buy and do. If you're in a position of not having your wife on board, then it is even more important to find a way to give yourself a private budget which doesn't impair your family's budgets. Slip some money into a piggy bank every week, save up your small bills and change, allocate money for "hobbies", or however you go about it. The growing sissy savings should get you excited and eventually let you buy the things you dream of without money worries.

L7. Shave your face clean. Yup, the beard, the moustache, the goatee... whatever symbol of masculinity you're trying to hold on to in order to not admit to yourself or your wife/SO that you really are a sissy? Got to go.

L8. Take pictures along your sissy journey for your own enjoyment, to share with your spouse or platonic ally.

L9. Take care of yourself. Clean up well after play. Watch for long-standing moisture around your genitals (all that edging you'll be doing) or you'll develop stuff you don't want (skin fungus, yeast, etc.)

L10. Consider who you will include in your sexual sissy journey. Just yourself? Your spouse/girlfriend? A third person? If you want to experience real cock, you'll have to find someone to play with and I highly recommend you work with your spouse to select someone you can have a relationship with (not random strangers please!) Think about this long and hard and talk about it with your spouse. I don't condone cheating so if she isn't open to it, you'll have to remain with fantasies and toys.

AND NOW FOR THE FUN STUFF... UNDERWEAR

F1. Figure out your sizes for women's clothing and lingerie. There are conversion tables online or guides on how to measure your body to order women's clothing. Waist, hips, chest, cup size, etc. I assume you won't have the typical female proportions but only a minority of real women have that either so it will get you close.

F2. Go to a lingerie store or women's clothing store that includes intimates and explore the different materials, colors, cuts and shapes. See what attracts you and what doesn't. Both my hubby and I love satins, shiny nylons, and the like more than cotton, microfiber, or lace. But learn what you like, what feels good to your fingers and looks good, what gets you excited.

F3. Buy a pair of panties. Yes, you could ask to borrow a pair from your wife or some other ally who knows about you but you'd be tempted to just 'borrow' a pair which is not nice. Not only are the chances you wear the same size low and you might stretch or tear them, it is a violation of trust and privacy. They don't call them intimates for nothing so don't be a crud with something that is intimate with my body. So yes, buy a pair. You should have a good idea on size (#7) and what turns you on (#8). You can go to a big retailer if you want to be anonymous and use the self check-out lanes or you can be more daring and go to a lingerie boutique.

F4. Enjoy your panties. Find some private time you can get naked and just explore your new panties. See how they feel caressing your body. See how they smell, how they stretch and how they are shaped. Let them tease or caress your hard-on. Use them to jack off. Cream them (hand wash after).

F5. Put on women's panties. This is a huge threshold for sissies, the first time the actually put on women's panties. There is no excuse, no manly explanation at this point. Only a sissy would think to put them on and get so hard when they do, right? It is a big declaration that you are accepting what you are. Tease yourself, put them on slowly. Feel how they slide across your legs as you inch them upward. Feel how they grip your bottom and how they cover your erection. Touch your body, feeling the panties on you. Tug them, adjust them. Walk around in them.

F6. Buy a bra. Like #F3, borrowing one is not nice so get your own. You should know what turns you on the most (#F2) and what your size might be (#F1) so you can go somewhere to get one and do self-checkout if you are anxious.

F7. Enjoy your bra. Like #F4, appreciate this delicate creation of femininity for its material, how it feels to your fingers, how it feels teasing your naked body and teasing your cock.

F8. Put on the bra. Like #F5, this is another huge threshold the first time you put on a bra. Even more than panties which are kind of like men's underwear a little, a bra is absolutely only a women's garment so know when you put it on that you are really a sissy because normal guys wouldn't think of putting a bra on, right? ;) Enjoy the tug of the straps, the way your chest feels with the bra holding you. Put some panties, etc. in the cups and admire yourself in the mirror.

F9. Buy thigh high stockings or pantyhose. I hate pantyhose myself so my hubby and I both wear thigh highs. sexier and more comfortable to me. But choose what you like

F10. Enjoy your stockings.

F11. Put on your stockings.

F12. Buy a full slip, F13. Enjoy it, F14. Put it on.

F15. Buy a half slip, F16. Enjoy it, F17. Put it on.

F18. Buy a teddy, F19. Enjoy it, F20. Put it on.

F21. Buy a camisole, F22. Enjoy it, F23. Put it on.

F24. Buy a baby doll. F25. Enjoy it. F26. Put it on.

F27. Buy a bustier, F28. Enjoy it. F29. Put it on.

F30. Buy Shapewear (Spanx, etc.), F31. Enjoy it. F32. Put it on.

F33. Buy High Heels at least 4" in heel height (bonus points for getting stiletto heels). Get them with an ankle strap with buckle., F34. Enjoy them. F35. Put them on.

F36. Buy Women's sneakers/runners, F37. Enjoy them. F38. Put them on.

F39. Buy a Jogbra or equivalent, F40. Enjoy it. F41. Put it on.

F42. Buy Leggings, F43. Enjoy them. F44. Put them on.

F45. Buy sexy, short running shorts, F46. Enjoy them. F47. Put them on.

F48. Buy one or more skirts (short, leather, tight, flowy, etc.), F49. Enjoy them. F50. Put them on.

F51. Buy one or more dresses (nice but not catch attention, sexy/club dress), F52. Enjoy them. F53. Put them on.

F54. Buy a French Maid's costume (as fetishized or historical as you like). F55. Enjoy it. F56. Put it on.

F57. Buy a Sissy Dress (lots of layers, satin, etc. check them out online). F58. Enjoy it. F59. Put it on.

F60. Buy a Prom Dress (current or retro/vintage style). F61. Enjoy it. F62. Put it on.

F63. Buy a Wedding Dress (current or retro/vintage style). F64. Enjoy it. F65. Put it on.

F66. Visit a lingerie store that carries lingerie that fits you. Ask the most attractive salesgirl for some help. Tell her you want to buy your wife something sexy. Ask her what she thinks is sexy, what colors she likes to wear. (Be aware, if she's not comfortable, don't push it but most saleswomen want to be helpful.) Make sure it is your size and buy it. Bring it home, enjoy, and wear it. (Always be prepared to buy something from them when you go to a store like this. Even if it is something inexpensive like more panties or a pack of thigh highs. Reinforce with them that you are a serious shopper and not someone they have to worry about.)

F67. Visit a lingerie store (like F66) but quietly admit to the salesgirl that you're buying for yourself. You can ask similar questions for her guidance, ask her how to figure out your size (even if you think you know it). Again, make sure you buy something even if you aren't able to find the type of undies you're looking for.

F68. Join the Rewards Program for the lingerie store you are going to be visiting regularly. Not only can it save you some money or get you more goodies for your money, it is a sign of being a serious shopper. Set it up in a way you feel maintains your privacy as required.

F69. Wear each type of lingerie under your clothes during the day. Feel how feminine you feel all day and how you keep up a level of arousal all day. (If this is too distracting to what you need to do in your normal life, go to a bathroom and cum and refocus on your job/purpose).

F70. Wear your lingerie at home under your clothes, around your family, neighbors, etc. Enjoy your secret femininity, your secret sissy around them.

F71. Wear your lingerie at night. I understand this might not be possible but if you need to, you could wear it under your pajamas or t-shirt/shorts or however you sleep.

F72. Take an elaborate outfit of your lingerie with you in a bag or something to work. During the day, find a time to go to the bathroom or someplace with privacy and get naked. Enjoy putting on the lingerie and playing with yourself. Put your clothes on over them and finish your day. If you need to, before going home change back.

F73. Go to all doctor and dentist appointments wearing lingerie instead of guy underwear. Yes, this includes your annual physical. If the nurse or doctor sees something or pantylines or bra straps, etc. and comments, you can just say that they feel good to wear without getting into detail.

F74. Wear dark lingerie under light clothes so it can be seen. Go in public somewhere.

F75. Wear clothing that leaves you with clear panty lines. I recommend brazilian cut panties, something distinctly feminine.

F76. Research, budget, and purchase Breast Forms. Which kind depends on your budget but I would advise either a bra that takes inserts you can then wear (less expensive) or ideally ones that attach to your shaved chest (Hubby loves his and might wear out this first pair soon!). When you receive them verify the skin tone is a match (or close enough) and the size is correct before you open them.)

F77. Open up your breast forms package, read all the directions, shower and dry off, and then apply them. Watch yourself in the mirror to position them naturally and equally on both sides. Hold them in place until the adhesive secures. Explore them with your fingers looking down at the view all women enjoy. Feel how they feel as you hug yourself and move around. Watch yourself in the mirror and make your most feminine movements.

F78. Try on lingerie and clothing with your new breasts, enjoy the feel, find which things you might want a different size now. Check out your figure with lingerie or lingerie and women's clothing on.


SOME EXPERIENCES...

E1. Find a local spa who serves women and men. Make an appointment for a manicure/pedicure. Wear your lingerie under your clothes but not your stockings. Enjoy the atmosphere, chat with the employees, enjoy being among all the women. Ask them to put a clear nail polish on your toenails and fingernails.

E2. Revisit your spa and ask for pretty colors for your nail polishes.

E3. Visit your local spa and get a skin care treatment: exfoliation, etc. As always, wear your pretty lingerie in case they get to see it.

E4. Research hair removal techniques and select one process that you want to try. (Lucille Sorella's "Femme Secrets" web page is a great place to start for this any many other sissy topics). Begin with a discreet area of your body and work to whole areas, sensitive areas which can be tricky, and develop a routine until you are "brows down" fully shaved every day and your skin tolerates it.

E5. Visit the make-up counter at a specialty shop or a department store. You can use any excuse you like or be very straight forward with the ladies but request a sample makeover. Explain you want to find out what colors work with your skin and what a professional might be able to do to feminize your face. Get them to explain what products they are using, and maybe what the top three tips they might have for you to learn this at home. It's a lovely way to have women support your sissidom in a non-sexual way. As usual, be sure to purchase some of their recommendations. These girls have to make a living and you need to prove you aren't a flake. You want to make as many platonic allies as you can. (Remember the names of the ones you like the most and are most welcoming and helpful. Patronize them again.)

E6. Drive around in only bra and panties. (Try not to get pulled over!)

E7. Shop for high heels wearing stockings under your pants. Get a female sales associate to help you. Ask her for advice on what she thinks is sexy.

E8. Practice putting on or touching up your makeup using only the rearview mirror. (Bonus points if this is while you're doing E6!)

E9. Wear a bikini bottom to the pool. Your choice on how clearly it is a woman's bikini bottom based on cut and color (but you know they all look like women's swimsuits...)

E10. Lay out for a tan on your front and back wearing a bikini swimsuit. Make sure you tan long enough to have clearly incriminating sun tan lines but not "skin cancer" long.

E11. Visit strip club wearing thin trousers, thin button down shirt, thigh highs, garter belt, bra, panties. (bonus points if you wear heels instead of men's shoes). Talk with the dancers until you find one you're attracted to who is pretty. Get a private dance (tip very well) and tell her what you're wearing, letting her feel your garter clip clearly through your pants, your bra and bra strap. She can do all the touching. Think of things to talk to her about like you're trying to find the best color of lingerie for you to wear and if she has an opinion, etc.

E12. Pay for a cross-dressing experience with a female professional (escort, sex worker, dominatrix, lifestyle therapist, whatever is legal and attracts you). It could be a dress-up session, a humiliation session, bondage as sissy, role-play, pegging, shopping together, girlfriends-experience, make-over, boudoir photographs, etc.

E13. Visit an adult store. Get a feel for it (do you feel comfortable enough?). Ask the attendant for "toys for feminine play", videos for pegging and shemales, lingerie and where it can be tried on, etc.

E14. Re-visit an adult store (or visit a different one) and ask if you can try on the lingerie. If yes, find some outfits and try them on. Again, always buy something if at all possible to prove you aren't wasting their time for your jollies.

E15. Visit/re-visit an adult store and ask for help. You want to buy a dildo that looks like a cock but there are so many. Ask what the differences are and how to take care of them. Definitely buy one and some lube (adult store lube is crazy expensive, you're better off with KY Jelly from your local grocery or drug store). Ask if they have gaffes or cock rings. Also explore butt plugs.

E16. Revisit the adult store in some level of clearly feminine attire - full outfit+makeup+etc., or just a skirt, or just a dark filled bra under a light colored shirt. Enjoy your sissy identity in a sex environment.

E17. (Requires F76-F78). Wear a loose top you could wear with your breast forms. Take your breasts forms to a sexy lingerie shop (or women's clothing store with lingerie if you prefer). Explain that you want a bra fitting but want to use the changing room first to put on your forms. You should be practiced at this (from repeating F78). Ask them to fit you in the dressing room (unless you are bolder than any women would be!) Scratch that. Stick to the dressing room or they'll get embarrassed or feel awkward. As always, buy a lovely new bra in the size they recommend. Bonus points if you wear the breasts and the bra out of the store.

E18. Study how to be feminine. Start at the beginning like all girls: CosmoGirl, TeenVogue, etc. Read the trash on makeup, relationships, clothes, exercising, etc. It isn't really great information but I'm sure you sissies will gobble it up. It isn't bad for learning basics that women have had years to practice.

E19. Graduate to Cosmo, Vogue, and others which are just as trashy but aimed at women.

E20. Visit lingerie, women's clothing, and fetish clothing web sites. Sign up for their email newsletter. If you can order things safely, take advantage of their sales and discounts. Otherwise enjoy the stream of sexy things in your private sissy inbox.

E21. Buy some cheap makeup: lipstick, blush, foundation, eyeliner, mascara. Watch some youtube videos and follow along. Also look for youtube videos for drag or crossdresser makeup (they'll have more suggestions on getting that feminine illusion that a basic tutorial won't get to). Get proper makeup removal wipes and wash your face fully each time. Practice until you have found the best way to complement your features to be feminine.

E22. Introduce subtle elements of make-up to your look daily (clear nail polish, makeup shades that match your skin and lips.

E23. If you have long hair, learn how to style it in a feminine fashion. Again, youtube videos are your friend and lots of time to practice. Be prepared to jump in the shower if your spouse doesn't know or approve.

E24. If you have short hair, shop for a wig. Talk to the saleswomen in stores about styles, how you like to dress en femme, and what wig might work best for you if you wanted to walk around in public (no neon pink waist length wigs, you can buy that as your second one if you want it). Shoulder-length straight or wavy blonde hair in a natural color is a nice sexy choice. I don't own any so the store can counsel you on caring for the wig, how to attach it properly and ensure it looks natural.

E25. Shave your genitals. Either completely or a sexy little landing strip would be cute.

E26. Use the women's restroom in some public place. I'll leave it you to figure out how to do that safely.

E27. Always pee sitting down. Only men piss standing up.

E28. Go to a costume store or adult store and buy yourself a tiara and pageant sash. Dress up to your best at home and reward yourself with the crown and title.

E29. Purchase a princess style gown, pretty slippers, and watch your favorite Disney princess movie enjoying how the dress feels.

E30. (This isn't something hubby and I see as sexy but it has come up often enough talking with sissies to include it) Buy and wear feminine pads in your panties during the day. Do this every month for several days.

E31. (This isn't something hubby and I see as sexy but it has come up often enough talking with sissies to include it) Insert tampons into your bottom and wear during the day. Do this every month for several days.

E32. Walk in your high heels. The heel of one foot is placed directly ahead of the toe of the other foot. Walking down a line like this will give anyone a lovely swing of the hips (and bottom if you've got a good one). Practice daily until you can walk in heels down stairs, in grass, and around the house with confidence and even without thinking about it, that they are just an extension of yourself and walking in them is natural.

E33. Change out all your bathroom products for feminine versions. Razors, shaving cream, deodorant, pink toothbrush, shampoo, conditioner, etc.

E34. Purchase some Sissy literature and read it all. There are plenty of titles on amazon.com and other places.

E35. Purchase women's perfume. I recommend Eau de Toilette as the least strong to start with. Know that if you put it on too heavy, even a good shower might not get all the scent out so if you have privacy/relationship issues, be careful. A light touch behind your ear or on your wrist can be enjoyed for your playtime or renewed if you'll be a sissy for a longer stretch. Try to avoid the heavy "stripper perfumes" that men seem to go for unless that is just what turns you on most.


SOME SEX THINGS...

S1. Watch ten Cum-Eating Instruction (CEI) videos in a row.

S2. When you masturbate next wearing panties or more, taste a touch of your cum.

S3. When you masturbate next wearing panties or more, cum into a small glass or container. Begin to masturbate again as soon as you are recharged and then eat that cum at your peak before orgasming again.

S4. Repeat, pour your cum over a realistic cock dildo and suck it clean.

S5. After S4, when you masturbate for the first time, eat your cum immediately.

S6. Never orgasm from masturbating without eating your cum.

S7. If having sex with someone, 'clean up' by eating your cum out of her pussy, his/her ass, off his/her body.

S8. Watch sissy hypnosis videos for 5 minutes before masturbating.

S9. Watch sissy hypnosis videos for 5 hours before masturbating.

S10. Watch sissy hypnosis videos daily before masturbating.

S11. Cream in your pretty panties and then wear them all day. (Yes, those women over there can tell you are a sissy who creamed his panties. ;) )

S12. Get your dildo, watch cock-sucking videos (women sucking) and try to match their techniques. (Use a lot of spit)

S13. Get your dildo, watch cock-sucking videos (sissies sucking) and try to match their techniques. (Use a lot of spit)

S14. Get your dildo and your lube. Make sure your butt is clean. Put down a towel you can launder. Pull your lingerie/outfit out of the way enough to not get messy. Lube up more than you could imagine you would need and start slow. It may take minutes for your body to accept this cock you want to push in especially if you are a "size queen" and got a big guy. Eventually, you'll feel that amazing sensation of the cock sliding into you. Relax, let your body adjust. Eventually start moving it in and out. Slow-fuck yourself and watch in a mirror if possible. Work yourself up until you are touching your cock in your panties. Feel that cock fucking you and focus on that until you cum.

S15. Repeat fucking yourself until your body accepts it faster.

S16. Mount the dildo in the bathroom (or somewhere private with a handy flat surface for the suction cup mount). Bend over and fuck yourself back on his cock until you cum.

S17. Do what you need to in order to enhance the cock-fucking experience and see if you can get so worked up you cum without touching your cock.

S18. Wear your lingerie under your clothes and put your dildo and lube in your bag. Go to work or someplace like a public bathroom. Get private, strip to your lingerie, fuck yourself until you cream big. (bonus points if you brought your high heels along and wear them during this play time).

S19. Call a sissy mistress sex line. (Try Enchantrix Empire or sissyschool dot com as just one group my hubby likes). Check the different women out first in what they like to do phone calls about and make sure they match your desires. Explore what kind of calls they do (domination, girlfriend experience, encouraging lover, etc.) Reach out to ones you think might be good and converse in email a little. They'll want to know what you like and what kind of call you want. Once you pick one to have an experience with, agree on what to do during the call. (Unless you are very well off you probably don't want to spend hours with them ($$) so pick one or two experiences you really want a woman to do with you.) Hubby Tip: If you are concerned about how to pay and aren't fully open at home, you can purchase VISA gift cards at the grocery store and pay for the call that way.

S20. Do a second sissy mistress call. Try someone else unless you just loved the first experience. See if you want to make it a regular thing.

S21. Masturbate but don't cum. Okay, that's a broad way to put it but Hubby assures me that edging (stimulation without the release of orgasm) is very pleasurable and keeps him aroused generally for days. (Didn't have the heart to tell him I edge all the time when I want to feel horny all day lol). We've even had pegging sessions where we stopped before he would cum so he'd keep his 'sissy state' strong. Eventually chastity could be introduced to enforce this rule.



SOME ADVANCED THINGS...

A1. Come out to a platonic female friend. You can work up to this over time but hopefully you have a female friend you feel you can trust or can work up to a trust. Be clear from the start that you are married and this isn't trying to begin something sexual with her but that you need someone to understand and support you. You can describe yourself as a crossdresser if you need to. Don't abuse her trust by telling her overtly sexual things unless she asks about it. See if she'll go shopping with you to help find things that make you look feminine, get her advice, enjoy a woman in real life supporting this side of you.

A2. Build up to going in public as female/sissy. This is much easier if your spouse is an ally or you find a platonic female friend as an ally. Start by getting fully dressed/made up and driving around in your car.

A3. Get fully dressed/made up, drive in your car. Get out, walk around the car where people can see you, get back in, go home.

A4. Get fully dressed/made up, drive your car to the store, buy something, drive home.

A5. Use Halloween to go out femme for the first time or to push the envelope on dressing sexy or slutty or blatantly sissy.

A6. Sign up for female exercise program (limber you up, help you learn how to move your body in a feminine way, get healthier, feel sexier). Wear leotards or leggings or other feminine exercise wear. Talk to the instructor ahead of the first class to explain your situation and ensure she is okay with it.

A7. Sign up for female dance lessons (stripper dancing, sensual dancing, or the like.) Go either wearing your pretty undies under shorts and t-shirt or go in women's top and leggings/shorts. Talk to the instructor ahead of the first night to explain your situation and ensure she is okay with it. You can explain that you are a cross-dresser with your wife's support but want to surprise your wife by dancing for her. Make it feel as normal as possible.

A8. Ask the female dance instructor (or the women you are in class with if it isn't solo lessons) what you should wear when you dance for your wife. Tell them you were thinking of a cute skirt and top but want to be sexy. Do they have any ideas?

A9. Hormones and your body chemistry is a very serious thing. Consult your doctor to ensure they will not conflict with any other medication or medical conditions you have. You'll probably have to consult a therapist as well. You have to tell your spouse you want to do this. It does not mean you want to transition fully to become a woman with Sexual Reassignment Surgery but you simply want slightly more feminine features (sissies aren't women). Discuss any possible side-effects to libido, erections, penis size, breast tissue size, etc. Having said all that, if you can meet those requirements, prescribed hormones or natural supplements with hormones can make changes to your body that make you look a little more feminine, more curve in certain places, possible development of breasts, improvement in soft skin, etc. My Hubby has been taking a natural source at ~low doses and has developed small breasts and I'd say he is more "hippy" now. Women's clothing fits him a little better. It probably has contributed to his difficulty getting erect with me in any traditional sex attempt but he still gets fully erect and cums when I peg him or we do other things so the jury is out on that one.

A10. Watch how women move when you are out in public. Be careful to not be creepy about it but spot one or two moves each time as they walk or talk with people or best yet when they are flirting. Go somewhere private or home and mimic their moves. Practice walking that way. Wear a wig and learn the hair flip flirtation.

A11. Pierce your ears. Earrings are fun and a great way to enhance your femininity. Yes you could go with clip-ons but for the real female experience, you need to be pierced in both ears. You need to know if you are allergic to nickel (common material the posts are made out of) or stick to hypo-allergenic earrings. When you pierce your ears you need to have a pair of earrings to wear in the holes until they heal. You'll need to either be ready with your best Odell Beckham Jr impression or forewarn your spouse/friends that you're getting it done. Big but sexy step for sissies.


AND SOME NOT THINGS...

There are topics that pop up with sissies every once in awhile. I don't think these are common enough to be sissy things and they have ardent followers who are not sissies. I'll at least mention them, but they aren't part of the list: Adult Baby/Daipers, Cuckolding/Hotwife, Big Black Cock (geez pretty racist there), Bondage, Whore play, Domination/Submission, Orgasm Denial, Extreme Humiliation. Plenty of places to go for that besides here.
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WOW you are a true GURU girl! hope to see more posts like this
 
Another person's version...

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Another...

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Hotel Sissy Story

Gemsissy said:
I'm way behind lol...
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We wrote this story together now sent to literotica to be published if accepted

Hotel Le Marque: A Dual Account

You're coming up on your one year anniversary at Le Marque Hotel. It is a high end business with strict rules but you've personally helped celebrities, supermodels, and many beautiful people. Anyone looking at you would probably just see a slender man with a kind of pretty face in a sharp uniform (slacks, white shirt, jacket, black shoes). If someone looked very closely, they might see a hint that something else is happening under your uniform... luscious satin bra, matching panties, garter belt to thigh high stockings. You try to avoid panty lines but a girl can't be sure.

Only one person, Veronica, knows your secret and she's been very good at keeping it. She teases you when you're both on duty overnight making you show her your panties or showing you hers but it's just fun. She's very loyal to her girlfriend, Marcia, who you've met and think she's cute and very nice.

One of the most intriguing aspects of Le Marque are the *special* parties. They are very hush hush and only a select club know about them. As a hotel worker, you're more aware as you sometimes deliver food and drinks to the penthouse party rooms. The kind of parties can vary quite a bit. You've seen lesbian orgies, gay orgies, dommes and more all of which give you plenty of fantasies to masturbate to when you get home.

Tonight is going to be special for you too. It's almost midnight when Veronica comes over to you with a "serious trouble" look. You enjoy how she bounces in her tight dress uniform but quickly pay attention.

"We've got a special in the 1004 penthouse and we're having trouble with one of the orders. They'd requested a French maid for their playtime but apparently Joanie isn't quite what they wanted..." You know Joanie is buxom, very sexy, and very popular at the special parties. "What's wrong?" Veronica looks you over. "What's your dress size again?"

"12" I nervously said to Veronica. She smiled and took me down the corridor up one flight of stairs to a storeroom where several outfits were hung on a rack. She ordered me to strip down to my underwear and put one of the maid dresses against my body. "That'll do honey they'll love you on this." I put the outfit on and it fitted ok with a short skirt than showed off my smooth legs. Veronica lifted up the skirt to expose my panties and said "cute weenie... they'll have fun with that sissy. Now off to the kitchen and wait for their call".

Veronica came into the hotel kitchen and told me to get ice cream tubs out of the freezer and dishes and cutlery. I put everything on a serving trolley and took it to the lift. Veronica followed carrying juices and smoothies. The lift came down and Veronica looked me up and down and said l looked cute and sweet. But she didn't follow me into the lift, saying that she had to be on call at the desk for other hotel residents. I asked Veronica what to expect as she'd been in the penthouse party earlier. She laughed "wait and see sissy!"

The lift doors shut and began a quick climb six floors up. I rearranged my dress and lifted up my padded bra, as a bell rang as the lift past each floor. My knees shook and back got sweaty as l got nearer to the sixth floor.

The last bell rang and the doors opened to the penthouse apartment. Music was really loud and in the room were a dozen people dancing half naked. When rolled the trolley into the room two of the guests saw me and came over to inspect the trolley contents. One of them got overexcited saying: " Wow ice-cream lovely". The other guy ignored the trolley looking me up and down and asked me where was Veronica. I told him on call. So he said "never mind you'll do" and burst out laughing as he danced around the room.

You have a moment to look around though your face is flush with embarrassment. Sure you wear slutty lingerie all the time and even show to Veronica but being fully sissy dressed to a bunch of strangers? I mean you'd fantasized about it many nights as you'd masturbated but this was reality. You were standing in a penthouse full of men and women wearing nothing but sissy and slutty clothes and the quick make-up job Veronica had done on you.

Thinking back, you're starting to wonder if Joanie had even been scheduled on shift tonight. This might have all been a set-up by Veronica. Your relationship with your platonic-so-far girlfriend might be changing seriously and the thought of Veronica domming you gave you a little thrill.

As you look around and see men and women checking you out, your cock is full and throbbing in your satiny panties. It never was very big so your panties still look very girly on you. I come up to you wearing high heels and a tight, short skirt with panties but nothing else. My D-cup breasts are full and perky and my blonde hair brushes the tops of my shoulder blades. I have a drink in one hand. "Now, we have a few bets to settle. Anne Marie says sissies are the best pussy-lickers and I say only another woman can really eat you out properly."

With that I grab and fondle your ass through your panties before guiding you into one of the 'fuck pits' surrounded by couches and chairs with people ready to watch. A woman in a red dress downs her drink and joins us. There are some pillows on the floor.

"Now are you an eager slut or do we have to force you?" I ask playfully. You can see some people are starting to play with bondage.

So many thoughts came into my head l was dizzy with anticipation of all the things l had seen a sissy perform online in the safety of my laptop. Now I was in the BDSM world l had fantasized about but too shy to do in this situation. My knees trembled as l was lead onto the cushions and pillows. You had your hand between my legs and two fingers in my pussy hole. The woman in red stood over me and held my wrists together so to cuff me. You told me to get on all fours while you pulled down my panties to expose my ass.

Several people jeered and applauded at the sight of my pink bubble bum. You took hold of my hanging balls and squeezed tight making me yelp. The woman in red stood in front of my face with her pussy exposed in crotchless panties. She took my head and planted it between her thighs and ordered me to eat her out. You in the meantime were busy lubricating my pussy and preparing it for the gang bang.

I could only hear the excited voices of the party goers putting down their bets as l had my tongue deep in her pussy. The betting suddenly stopped and so did your lubricating my pussy ass. You took a metal butt plug and inserted it deep in my pussy and slapped my ass cheeks hard several times.

I heard more shouting from the party goers who crowded around in a circle in the widest area of the penthouse. The lady in red took my head and turned me to watch two naked guys wrestling in the circle. The lady told me they were fighting for a prize and the prize was my pussy! I was on all fours propped up on cushions so my ass was in the air. I watched sideways at the wrestling match between a fat guy against a tall thin guy. The thin guy was too quick for the fat guy who's cock was bouncing between his legs. The fight was over in minutes when fatty smothered skinny by rolling into him and getting him to submit.

I assumed then fatty would fuck me first but he didn't but instead made me suck his fat cock while a second match began. This went on for until there was a winner who was a black guy was a very long cock. He took over from fatty, as l had to suck him off. Fatty got behind my butt and worked his fat stubby member in my hole. The third wresting match began as l was being fucked hard by fatty and my throat full of a black cock.

Your mouth was full of musky black cock as he held your head and fucked you. You gasped air between thrusts when his cock would slither into your throat. The sensation of deep-throating a cock is thrilling you, your little pee-pee hard and aching. Add to that the hands of the guy behind you, gripping your hips and controlling you as he smacks into your ass, his fat cock pumping in and out of your slick pussy. You never thought you'd actually be double-fucked, actually have two delicious cocks inside you at once. The crowd howls as your pee-pee streams out cum as you orgasm, your balls getting so tight, the pleasure so intense you almost pass out.

The room starts to swim. Any time you can look away from the black man's body right in your face, you see people getting naked and coupling in all kinds of ways. Women with strap ons are fucking men, women are 69ing with other women, men are sucking each others cocks. You are a bit of a centre show but plenty of side action is happening.

The man behind you grunts and holds his cock deep in your pussy where you feel it throb and pump out cum. His cock wasn't that remarkable but his sperm load was immense, giving you a distinct feeling of being filled even when he pulls out, the cum oozing down your thighs. You can't see behind you but a woman's hands attach cuffs to your ankles, spread your legs and affix a spreader bar between your ankles. Someone kneels behind your bottom and you feel their mouth on you, tonguing and sucking cum from you.

"I knew you were a little slut," laughs Veronica. You jerk and look up to see her standing next to you as the black man continues to fuck your slutty mouth. She's wearing a dominatrix outfit of a tight satin corset that reveals her gorgeous breasts, satin panties, thigh high stockings, knee high leather 5" heel boots. "What more can I do with you, I wonder... Is there anything you won't do?" she asks herself rhetorically.

The man making you gobble his black cock stiffens and howls as his balls jump and cum blasts up his cock and down your throat. Half-way through he partly pulls out, filling your mouth with pungent sperm and finishing with some ropes over your face. Veronica, looking especially cruel, is delighted with your performance.

"I knew she was a little sissy slut," she calls out to the group. "But I never guessed she'd be such an eager cock-sucker and cum dump!" The crowd is appreciative of your performance and as degraded as you feel, you also feel a glow being a little porn star. "I think she needs a 5-way!!!!"

Two men come up to you, their cocks waving in your face but they pick your trussed body up, cum dripping down on your slut maid uniform. Veronica's quick makeup on you has gotten smudged with cum, drool, and sweat. You are placed on your back on a nice padded table with your bottom at one edge and your head leaning back over the other edge. Your legs are hiked up and attached by the spreader bar to hooks from the ceiling. A strap is place around your throat, securing you to the table, along with a strap around your stomach over your dress. Your wrists are no longer cuffed together. I walk over and secure your clit in a tiny cock cage making you groan as its unable to recover from your orgasm and grow.

"Gentlemen!" calls out Veronica standing on the opposite side of the table than I am. "Give me one!"

A stud with ripped abs pulls down his boxers to release his big cock. He strides over, teases your mouth with the tip of his cock before pushing it inside. He starts a slow fucking rhythm as you lick, suck, and gobble as much as you can.

"Give me two!"

Two other men pass through your limited view to stand on either side of your table. They each take one of your free hands and places it on their cock. You're surprised at how different all these cocks are but they feel so erotic. Without prompting, you start fondling and stroking them.

"One more!"

You are moaning and writhing in bondage on the table when you feel very firm hands grab your ass from an odd direction but then the tip of a cock pushes at your pussy. In the soup of cum it slides it easily, though it isn't as fat as the first one. Four cocks and you are in heaven, your clit aching in your cage as you suck, stroke, and get fucked.

"Now for number five!"

'Five?!?' you think quickly. 'Where the hell...'

Your question is answered when a second cock head begins to explore the opening of your pussy. He seems to coordinate with the guy thrusting from under you. It takes more than a minute before you yell around the cock in your mouth and your ass opens enough to let them both inside you. Your body is shuddering from the overload of erotic pleasure and being used as a total cock slut! The two guys standing over me with both my hands stroking their bone hard cocks kiss one another and the guy thrusting himself down my throat.

I'm no longer fully conscious but in some weird cosmic fuck zone!

Veronica realises my state and leans over to pinch my nipples hard to get me to attention. She leans over whispers in my ear that this is just the beginning of her plans so sissy better stay awake. The guy thrusting himself in my mouth shot his load making me gag as a dozen cum shots ejected down my throat. My mouth ached as he pulled out and slapped his limp wet cock across my face.

The two guys next to him were ready to shoot their loads. Veronica told them to save it as she wiped the cum off my face. My pussy hole was being stretched to the limit by the two studs riding together in unison. I'd stopped feeling their thrusts as my ass had gone numb with so much pounding. After a further period of being fucked they both pulled out and walked around to place their cocks across my face.
Veronica laughed as the two cocks slide over my mouth and nose. They seemed huge compared to my tiny clitty locked up in a cage.

Veronica shouted "see everyone the difference between real men and a weedy sissy girl with a clit of a dick!" The two guys moved away from my face and took the other two guys l had been stroking and proceeded to fuck them instead! I watched them from my upside down position riding alongside me. Veronica in the meantime loosened the straps and took down the spreader bar from the ceiling hooks releasing my aching limbs. She gave me a box of tissues to wipe my face and all the cum and sweat from my ass. She then took me off the table and sat me in a reclining chair.

"Sit there sissy, rest up for awhile. Here's a large glass of vodka mix as you're going to need it for the next few hours." You drink the strong drink and feel calmer but more heady. Watching the orgy around you, you are amazed. You knew these *special* parties got up to some sexy stuff but your eyes are glued to two handsome guys, one bent over and the other fucking him with... sensual thrusts while a woman sucks the receiving guys rock hard cock. Another guy is in some elaborate bondage including a mouth gag that also has a big protruding cock from it and a woman is fucking herself silly on the protruding dildo, much to the bound guy's frustration. The men are drinking a special cocktail and when you ask me, I explain that it ramps up their cum production and recovery time. As you watch you can see the results. These guys are almost never getting soft and the amount of cum in people's mouths, pussies, asses, and over their body is amazing.

"I've got a job for you, sissy," says Veronica, drawing your attention away from me. She hands you an ice bucket. "We need ice for the drinks. If the machine isn't working on this floor, go to the next floor down. Use the elevator."

You stand up, try to smooth out your sissy maid's dress and stockings and take the bucket from her.

"A couple more things..." she says before letting you leave. She pulls your panties down to your ankles (and you know you must keep them there around your high heels) and then inserts a cock-shaped vibe with a wide end into your ass. It fills you deliciously, making your clitty ache in your cage to be released. She slips a hot pink ball gag in your mouth and locks the straps in place behind your head. And finally, in a moment of kindness? she puts a little mask on you. You can see through the eye holes and it doesn't cover your gagged mouth but it might keep others from recognizing you immediately. There was a lot of the hotel staff who did NOT know what the *specials* were all about or come to the penthouse floor and certainly no one besides Veronica knew you were a submissive panty boy.

With that, she opens the door, grinning at the burning blush in your face.

Being seen as a total, cock-gobbling sissy slut in front of a sex orgy was one thing... being seen like this potentially by hotel guests? The hall outside is empty but still terrifying. You step out, your walk hobbled by your panties around your ankles, and the door shuts and locks behind you. At least the ice machine at the end of the hall wasn't too far away and few people came to the penthouse floor. You simper and hobble your way to the ice room but your heart sinks as you see and "out of order" sign on it. Blushing deeper and your heart racing, you know you have to go down a floor.

Waddling to the elevator, you touch the button and are relieved when it opens right away, staying at penthouse level when not in use. The car is empty so you hit the button for the 11th floor and ride the elevator down, heart still racing. Stepping out, you realize the ice room is at the far end of the floor. With no choice, you start mincing your way there. Halfway to the ice room, a guest room door opens up just in front of you. Two women step out, pretty, in their 40s, dressed to go somewhere nice for dinner. Their faces at first are just shocked at the sight of you but then they burst out laughing!

"What are you supposed to be?" asks one. With the gag in your mouth, you can't reply more than grunts and moans which isn't helping.

"Are you exposing yourself to women, little boy?" asks the other, lifting the skirt of your maid's dress and seeing your caged clitty. At that moment, the cock in your ass starts to vibrate making you moan in pleasure.

"What a pansy sissy slut!" concluded the first. She takes a picture of you with her phone and then they head to the elevator laughing.

The embarrassment and the hum of the vibe in your ass make walking to the ice room much harder and its hard to keep your panties from slipping off your high heels. Twice you have to stop, bend over and get them back around your ankles. When you reach the ice room, the now familiar out of order sign is there and you realize what Veronica is doing. You also realize you have no choice. You remember something that didn't seem like much at the time but now secures Veronica's hold over you. There was that one night that she convinced you to let her take pictures of you in your lingerie and trying on the women's hotel uniforms. Plenty to get you fired and you'd never even imagined Veronica would use the pictures that way but now, you think she just might. You have no choice but to obey her. You feel in your gut that you couldn't do anything but submit to her even without the blackmail material. This is who you are and you've been waiting for someone to take your leash.

Back down the hall, into the (thank heavens empty) elevator and down to the 10th floor. The vibe has turned off and must be controlled by remote. You head down the hallway, mincing in your sissy dress, panties around your ankles. The next Out of Order sign awaits you and you wonder how far Veronica was going to push this. The lower floors are much busier at this time of night and you'd be seen by dozens of guests and several other employees.

On the 9th floor, there is a guest room with its door propped open and club music coming from inside. You risk a glance and see some guys dancing with hot girls and drinking. With no choice, you mince fast past the door and hurry as best you can to the ice room. out of order. Turning back, you see the guys and girls loitering in the hall, waiting for you. The vibe restarts and goes strong. You feel it massaging your prostate and think that even in the cock cage, this might actually make you cum.

"Hey slut!" Calls one of the guys, shirtless, 20s, blonde, handsome. "Come here!"

You think about escaping down the stairwell but know you won't. Your submission has complete hold on you. You mince forward toward them, keeping your satin panties around your ankles, the vibe thrumming in your ass, your cock aching in your cock cage barely hidden by the super short skirt of the maid's uniform. The hot pink ball gag ensures that everyone knows you are a sex slut.

The four talk amongst themselves as one of the guys and one of the girls check you out, finding cum on your uniform, lifting your skirt to find your cage and your bottom plugged.

"You know, I think we can have some fun here," concludes one of the guys as he removes your cock-shaped butt plug vibe. "She obviously loves cock!" With tha they lead you mincing into their guest room, leaving the door propped open. On entering the guests room l noticed three girls dancing around wearing only bra and panties. They were clearly drunk having been out night clubbing and continuing their fun.
When they saw me being lead into the room they cracked up in hysterics shouting and pointing at me. The loudest girl shouted "who the fuck is that?"

"We found us a sissy that's what and she looked lost or someone's playing us a fucking big joke!" Said one of the guys as he pulled up my dress to expose my caged clitty. The sight of this made the girls scream with laughter!

One of the girls took hold of my hand and bargain dancing with me while another girl took a large dildo and inserted it in my pussy. The guys took hold of the girls and began dancing around the room and rubbing their bodies together. I saw the guys through my mask eyelets fingering the girls while the girls took out their rock hard cocks out. I watched three of the guys begin to fuck the girls from behind while the other guy stood next to me and began kissing the girl fucking my pussy with her dildo.

This orgy continued until it was broken up by a commanding voice coming from the doorway.

"Sorry to break up your party but l was looking for my cumslut sissy." It was Veronica and she was holding a leather whip and a collar and lead in her hands. Veronica took charge of me by tying the collar and lead to my neck and began whipping my ass cheeks hard as she lead me out of the room to the sound of cheering! I knew you weren't to be trusted," began Veronica with an edge to her voice you'd never heard before.

You want to beg, to make her stop. You make the noises as best you can with the ball gag and she seems to understand you.

"Oh, puh-lease," she mocked. "You creamed your little panties just fine and sucked cock like a porn star. And now you want to stop? I don't think so. I got paid for your performance at the *special* and then a bonus from those frat boys. You have more money to earn for me, sissy Suzie."

She walks briskly ahead of you in her starched hotel uniform, back-seamed stockings and 5" heels. You feel the collar on you and find the lock she put on it so you couldn't take it off. Seeing the leash leading from your collar to her hand was so humiliating along with stumbling along in high heels trapped in your dropped panties. The elevator opened and two women were there. It was pretty late in the evening by now and they appeared to be a little drunk.

"Walk of shame!" they sing-song together before giving you a hug. "We feel you girlfriend! Sometimes it ain't worth taking the time to pull up your panties!" One leaned in very close to stage whisper in your ear, "You eat out your girlfriend good and she might take you off your leash, honey!"

The doors opened on the sixth floor. "By-ee!" sang the women laughing at you. Veronica marched you down to one of the suites at the far end of the hall. You glance in the ice room and see the out of order sign. If she'd let you go, you would have paraded up and down every floor of the hotel. Veronica pulls up your panties, snugging them around your ass and caged cock. She also takes the lock off the back of the ball gag.

She rapped on the door and there was a chorus of masculine cheers from inside. The door opened and you saw a crowd of frat boys or jocks, each with a beer or drink in their hands. "PAARRR-TEEE TIIIME!!!" they howled. Veronica handed the leash to one of the men and took the ice buckets from your hands.

"You've got her for the rest of the night. Just call me when you're tired of her," she laughs and closes the door behind you.

The room is rather dim and full of eight, nine? guys. They are all talking which makes it hard to hear what they are saying. One of them moves you over to a bed and ties off your leash to one of the bed legs. You can kneel upright but not stand. There is a leather thing they bring out and you feel your arms being inserted into it.. You feel it being locked to your collar. Finally the ball gag comes out.

"Please, stop, I didn't agree to..."

"Were you already wearing panties?"

"Well, yeah, but..."

"Did you fight her putting you in this getup?"

"No, but you don't understand..."

"Didn't you gobble cocks like a fucking slut already tonight until you made them cum?"

"Yes, but please, I didn't want this. I don't want to be a sissy!"

"Too late," he grins, pulling down his sweats to release a fat cock which he inserts into your mouth.

The room was spinning as l sucked on the frat boy's cock which seem to get thicker as he forced it down my throat. He held the back of my head and began pumping away. The rest of the gang laughed and cheered at the scene of me in complete bondage tied to the bed. The guy held off and pulled out of my throat saying he wanted to save it for later but for now it was game time!

Three guys pulled a large round glass table out into the middle of the room. Others placed chairs around the table and they all say down with their beers, whiskey etc and glasses ready for the start of several drinking games.

I was untied and lead to sit under the table below the guy l had been sucking. He instructed me to crawl under the table towards the guy who won the first round of games. On his command l was to begin to suck his cock until he shot his load or held off.

The first game began as the cards were shuffled and handed out one by one. The guy who had the best hand won my throat and l saw his hand slapping his knee as to signal to crawl to his waiting cock.

The guys jeered as they could see me through the glass table open my mouth to take his 8" inch member. They continued the second round of games this time pouring whiskies out and quickly passing them round the table. The guy who drank five shorts the quickest won the game and my throat.

This was the pattern of play for the rest of the night. Only two guys prematurely came in my mouth while the others held off until they gang banged me on the bed. The night was one of the longest in my sissy life, as each of the frat boys took their turn fucking my pussy. The reality was very different than fantasizing being gang banged by so many young and horny guys. My ass was so sore from the constant pounding and my throat was raw l couldn't speak for several days.

The guys left me tied to the bed post in the morning as they left early to get the coach home from the match. I awoke to a slap on my sore ass by Veronica who untied me and pulled me up onto a chair.

"You look a sorry sight sissy! Enjoy yourself last night hey? How many did the dirty on you six or seven or in total more like a dozen...you cum slutty girl."

Veronica took off my cage and made me take a shower. Then she took me by my balls and made me eat her pussy as l knelt before her.

"You love my pussy don't you sissy girl...that's it lick my clit not much smaller than that tiny thing between your legs isn't it? Later this evening a couple of hours before your second shift l expect to have you join me with a couple of my gfs on the second floor room 22."

Veronica laughed and strolled out of the room leaving me on my knees face full of pussy cum and her knickers on the floor left as a token. By the time Veronica had cum three times, she seemed to be satisfied. Morning light was streaming through the hotel window. You know she got off duty a few hours ago and you hope she covered for you while you were trapped in this night of raw sex. She handed you some fresh lingerie and a somewhat more conservative dress, stockings, low flats.

Looking you over, the stern look had disappeared and it seemed like your friend was there with you.

"Well, I did my best for you. I saw this opportunity and well, I'd wanted to dominate you ever since the first time you showed me you wore panties. I'd asked you little questions here and there until I was sure that you'd get off on this."

"Does anyone else know?"

"Just Lyle in security. He helped me monitor your escapades in the *special* suite and in the hallways. I had to give him a ride to get him to promise not to say anything about you... and, girlfriend, if you want a big cock, I think he'd be glad to give you a ride too!"

"You watched me on the security cameras?" you gasped. You'd totally forgotten about the hotel's security system.

"Watched and recorded. Savng material for some other time or... other purposes."

You didn't like to think about what she could do with the recordings but you didn't say anything.

"So, girlfriend, where do we go from here? If you're done with all this, fantasy fulfilled, bucket list checked, I'll understand and we can just go back to being panty friends. If you want more..."

Your head is swimming. You loved having Veronica in on your panty secret even if she giggled at your little cock. You didn't want to lose a female friend but you knew the floodgates had been opened. Your mouth still reeked of cum and you absently rubbed your sore jaw.

"I don't know... I kinda hoped you and I could, you know..."

"Fuck?" she said surprised. Then she laughed, big bent over laughter. "Oh, dear, oh my, why, why would you think that? You think I want a thimble-dick struggling on top of me, no offense!" It was clearly something she couldn't even imagine so she wasn't trying to be cruel, just honest. Your face burned red. You knew you had a tiny cock but hated people to see it and the reaction women had to it.

Veronica got up and sat on the end of the bed to be next to you, taking your hand in hers. "Honey, I really like you a lot. You might be one of my closest friends. To be frank, I did think about us having sex but it was lesbian sex, you know, with that thing tucked in a little cage, out of the way. If you don't have to be a 'guy' about it, then maybe we've got something..." With that, she leaned in and kissed you.

After a long, long strenuous night of raw sex, her kiss, her intimacy was like a glass of cool water in the desert. This was affection maybe more. You kiss her back eagerly and then calm down. The kissing is different than you expected and you felt yourself getting into a girl-vibe, imagining you're another girl lesbian kissing her. As soon as you did that, got less pushing, more sensual, she sighed, "yeah... like that..." Your kissing continued for several minutes before she leaned back.

"So, do you want to go further? Do you want to date me on my terms?" Your brain screamed yes but you could also feel this was a very serious moment and question.

"Yes but what are your terms?"

She gave you a naughty smile. "We can date, as girlfriends. You come to work as a girl, live with me as a girl, and we can be together as girls. Your thimble stays locked in its little pink cage. You won't need it though you might miss it. I'll transform you so you can pass as a girl and live as a sissy."

You nod slowly, thinking that sounded pretty good but the thought of being locked up for a long time, never fucking, never getting hard, that's rough.

"Now, I'll clearly be in charge. Sometimes, that means "mistress" will come out and she can be pretty forceful. She might have you do all sorts of erotic, humiliating, and challenging things. If you're sharing my bed, I own you and "mistress" has complete control when she wants it. Any resistance, any back-talk, whining, complaining, or refusals will mean you need to be punished. I'm not sure if that's something you really don't want to experience or if you're kinky enough to really want to experience it. I'm sure we'll find out either way."

"I can hack the hotel records but the other regular employees will obviously know you're dressing as a woman. No cover story about transitioning. They'll know you are a little sissy. I'll handle our finances though with your performances, I think we'll be rolling in the money and have plenty for all sorts of wardrobe for you and toys."

"So, what's it going to be, lover? Be mine? Or back to just a panty boy and lonely nights?" It didn't take me long to realise what Veronica was saying to me and that I had a stark choice between being under her thumb completely and transforming into the sissy I always was or just remain a loser.

I meekly nodded my submission to her more than generous offer to be her gf but more so her submissive bitch ready to be of use to her in many ways that included making some ready money. The world was quickly changing around me and I was going to have to adapt pretty soon to dance to Veronica's tune! She had a dual personality one quite sweet and caring the other stern and demanding to the point of cruel. Was the journey going to make a better sissy out of me? From Veronica's point of view her sissy was such a submissive girl it would be easy to train her in any way she desired. Being quite into domineering sissy boys and training them into totally pliant bitches was great fun. But she also realised that it took time to get total control over sissy's mind and body.

There were dozens of methods to apply for her to gain such power but she'd made a great start on sissy. Now to apply a set of strict rules for her girl to follow with a few rewards and lots of punishments otherwise. Little did her new gf reckon on that the road was never going to be a smooth a her fem body! "I'd bet you were going to agree," she said happily. She pulled out her cell phone and called Lyle.

"Yes, can you come up to room 5040? I need you to witness some things."

As you waited she fetched a pile of papers from the hotel room's desk. Lyle arrived quickly and clearly had a tremendous hard-on in his uniform pants. Veronica wasn't kidding, he had a quite large cock.

Handing you a pen, she instructed you to sign a bunch of documents. You went to read what they were but she held them to cover their contents, just expose the signature block. You glanced up and Mistress was clearly in charge. "Sign them, now!"

Meekly, you complied, afraid of what you were signing into or signing away but this was really putting you completely in her control. Lyle dutifully witnessed each document and notarized them. Once you were all done, she secured the documented in a briefcase and turned back to you.

"Sissy, show Lyle your appreciation for his help in starting your real sissy life."

Lyle broke out into a wide smile, his hand touching his cock in his pants. Even after a night of raw sex, you felt your face blush at the thought of sucking a guy's cock in front of your friend Veronica. Lyle unzipped his pants and pulled his 8" semi-soft cock out of his briefs. He stepped up so you could smell him and feel the heat from his cock.

"Hurry up, Sissy! This tardiness will have to be punished if it continues."

Another mega meat to eat! was hurtling through my head as l took hold of his handsome huge member. How long was it going to grow? I muttered to myself as the first few inches met my quivering lips.

"Come on baby girl show Lyle what a cock sucking bitch you are" laughed Veronica.
Lyle stood over me as his cock grew not in length as in girth filling and widening my mouth. He ordered me to look up at him and he wanted to see the strain on my face as he began thrusting down my throat.

I almost blanked out as Lyle took the back of my head in his large hands to keep me under his control. What happened next was such a surprise tears ran down my face as shots of saliva ran out my nose. I struggled to cope with Lyle's cock as my throat was very sore from the previous nights events. Veronica could see that my breathing wasn't good so she whispered in Lyle's ear and he pulled out and slapped my face with his fat 10" incher.

Veronica took hold of my hair and pushed my face into her cunt and ordered me to eat her out while Lyle got behind her and started playing with her ass cheeks. I knew then he was going to fuck her ass while l licked her wet pussy.

Boy! Did she grind my face into her as Lyle pounded her ass. This continued for several long minutes before Lyle was ready to cum. He pulled out of Veronica as she made a great yelp and held my head upwards ready to be sprayed with his jiss.

Good god! Cum after cum shot out of Lyle like streams of cream string hitting my eyes and nose and mouth.

"Lick it up sissy girl it's good for you to taste a real man's seed something you've never produced from your pathetic DNA dribblings".

Lyle stood over me like a grunting giant and leaned over to Veronica who and gently kissed his lips. I was on my knees face full of cum wondering what she was wanting me to do once Lyle had enough. Over the following weeks my new "mistress" Veronica took total control over my life. She told me to eat better and lose weight as well as do more exercises. I moved out of my flat to stay at her place and she gave me a housework rota that l had to do each day. Veronica made sure l completed each task to her high standards of cleanliness and hygiene. If on inspection she found l had not done a good job she bent me over pulled down my knickers and wiped my ass cheeks hard.

The regime she set was at first very strict and punishing. Rewards were few and far between. Veronica began the first real sissy transformation and set the slutty bitch tasks to do everyday to get her slave ready for the many horny Alphas she wanted to please. sissy was unsure of what the many instructions she signed the contract between them. But she was soon to discover that they weren't anything like she ever could imagine! There were loving times as well, girlfriend with girlfriend. She quickly got you to be passable at a quick glance and you began going out on dates to the theatre, movies, dinner, dancing, and more. Anyone who gave you a second look could clearly see you were a sissy man and it never failed to make your cheeks blush with humiliation even when other stares were jealous that you were dancing with a knockout like Veronica. There were times when "mistress" didn't seem to be around that you snuggled watching Netflix or talked about clothes, makeup and more.

Finances were not to be discussed so you definitely felt like a 'kept sissy'. You were conflicted about this, part of you loving the freedom of it but part struggling against feel so controlled and in her debt. Working at the hotel was challenging as the other women teased you mercilessly, making you lift your skirts to show your panties and your caged thimble-cock. Every once in a while, Lyle would corner you and you'd have to suck his cock again. You weren't called for any *special* parties but Veronica said you had to meet her expectations with the dieting, exercise and more.

Six weeks into your new life, Veronica sat you down. You crossed your legs like a girl without thinking, smoothing out the skirt of your pink satin sissy dress. She gave you a cup of tea to drink while you talked.

"Time for your transformation to continue. I have a friend who is able to squeeze you into her schedule. It's an experimental procedure but you're in really good shape now and it will go perfectly."

You began to feel a little light-headed and she took the cup and saucer from you before you dropped it.

"Trust me, my love, when you wake up, you'll love it!"

You couldn't put a full thought together let alone speak and then the darkness consumed you. Impossible to say how long you were unconscious but it must have been weeks. You dreamed of things but couldn't remember them. When you finally wake properly, you are dry-mouthed and groggy. You shift and feel you're in bed under satin sheets. Opening your eyes makes you wince from the sunlight but you quickly realize you're in our bedroom.

Shifting again and you notice something very different. The sheets slide across your silk camisole and arouse the large nipples on your big breasts.

'Big breasts?!?' your mind shouts as your eyes go wide. Your arms reach up and confirm that you now have large breasts. They feel completely natural and you feel everything your hands and fingers do to them. Touching your nipples feels very good and you feel these weights on your chest are completely you, flesh and blood. You immediately wonder how women keep from touching themselves constantly!

Next, you gasp and your hands fly down to find panties and inside is still your little cock in its cage. You are still a sissy, just one with big beautiful breasts.

"DDs," states Veronica from the en suite bathroom. She pokes her head out wearing only a silk kimono. "They said you'd come around this morning so I've been staying with you. Everything went perfectly, but do you feel okay? Hungry as all get out I'm sure..." Her look is genuinely concerned for you as she comes and sits next to you on the bed, pulling the satin sheets tighter against your body under them and tight against your breasts. Yes my mind was in a tiswas that l couldn't fully comprehend that l had huge breasts! I could feel the weight of them every time l moved and when l sweated they got sticky.

Veronica spoke about how l'd get use to them and though it felt strange and l had get back aches l had see the benefits (more so the men would) and grow to love them.

I looked nervously at her and asked what about my clitty and balls? Will you want me to have them removed and have a fake vagina?

Veronica laughed at the idea and replied: "you're a sissy not a woman nor a real man and your tiny thing between your legs isn't a problem. Men like to see sissies and shemales with their tiny dicklets just to make them feel even more superior.
No worries babydick you can keep your sissy per pee but it'll probably get smaller size anyway once it's placed in your cage unless I decide to unlock you.

Recovery seemed like it took forever but it was really only a couple weeks before you felt strong again. I'd done some shopping to get you some basics (DD bras) but clearly you'd need a lot of new wardrobe. You couldn't get over how amazing it was to have real breasts, beautiful large breasts that were so erotically sensitive. I'd made you orgasm more than once just by dressing you and then suckling on your large nipples, your panties turning dark with the cum leaking out of your cage.

The women at the hotel were amazed and demanded to see them many times. They would make you take off your uniform leaving you in panties, thigh highs, garter belt and bra, and heels and make you take off your bra. They would play with your nipples and tease your breasts even to the point of making you wet your panties. Some were clearly jealous and began to tell rumours about you to the guests. You started getting propositioned for sex all the time by male and some female strangers and I ordered you to go ahead with them.

"It's about time you started making the extra money. I'll handle the money from the tricks. You just blow their minds and make sure they cum back again and again."

The End but just the beginning?
 
Yes, I want S16 tomorrow night. I'm in a hotel room and I'll have my 10" suction cup dildo with me. I need to moisturise my body, put on heels, nail varnish and lipstick and ride it, impale myself on it over and over again til I spunk hands free. What a proud little sissy tramp I'll be when I achieve that. 💋
 
OpenMouth said:
Yes, I want S16 tomorrow night. I'm in a hotel room and I'll have my 10" suction cup dildo with me. I need to moisturise my body, put on heels, nail varnish and lipstick and ride it, impale myself on it over and over again til I spunk hands free. What a proud little sissy tramp I'll be when I achieve that. 💋
Click to expand...

You go, girlfriend!
 
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