Annie's Super Sissy Idea List!

[SweetAnnie40]

Thanks, and thankss for composing that list. I did come out to my sister. When I first told her she was so excited for me and allowed me to use her address for packages. However, when I finally found the nerve to dress in front of her the response was luke warm, "you just look like you in a skirt". It really crushed me and I honestly dont enjoy dressing as much since.

That is just terrible. How long ago was this? I would encourage you to revisit that and explain to her that you need her support. How did you come out to her? I mean, are you just a cross-dresser to her? Explain how important and amazing her acceptance was when you first told her and you want to continue to share this with her support but admit that you're fragile about how you look. Maybe she can suggest little ways to reduce how much you "just look like you"? Better fitting clothes? More strongly feminine clothes? Did you do anything besides the clothes when you dressed in front of her? A wig, makeup, breast forms or something to give you a chest, heels, any or all of these would help you feel and look more feminine. She could help you master any or all of them as well.

Just too sad to be accepted and then lose it. Let me know if you talk to her again or want any other suggestions.

I will say that my hubby had a similar experience with a platonic female friend who was letting him order packages to her house. He bought some latex, thigh high boots (not really his style but he wanted to try them). They weren't a great fit and she admitted they looked like fishing waders. He told me that it wasn't a good feeling but he knew she was being honest with him.

 

[Bob_Aganoush]

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.

What a great list, I can only imagine how long it took you to put this together. Thanks for taking the time to share it with all of us.

 

[Jenna2641]

Feminizing Workouts

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.

I been trying to get back into my exercise routine lately, which means you might not have seen me online in the mornings as much. When I read Annie's list I noticed L2 right away. I was pretty much doing that as part of my normal routine at my local gym. I was going to the gym every morning at 5:30am Monday through Friday as part of my regular routine. As part of one of the gym games I participated in years ago, I tried many of the different classes, some of them dominated by women gym patrons. I was all about trying anything that would get me active. As you can imagine, with the majority of the classes being women, the exercises had a feminine target. That kind of made it a bonus.

The ladies didn't mind at all & I just became another one of the girls. Other men have joined the groups from time to time and of course, I have done other classes, spin, P90X, etc. that have a more diverse gender mix. It is all about staying active (and controlling cholesterol without drugs).

Anyway, with COVID, I have been denied that outlet. I been trying to keep up with my running, but it is so easy to let a routine get disrupted when you have to motivate yourself. Well I am back on an exercise trend. I have gotten 4 runs in, but I want a little more. I just completed my first feminization workout that I hope to work into a regular routine of running & myophacial rolling.

I made a blog entry about it on XHamster here:

https://xhamster.com/posts/10015817

But if you want to jump to the original blog entry by Lucille, you can find it here:

https://feminizationsecrets.com/feminizing-workouts-transform-body/

Being healthy is good for everyone. Exercise is a good part of it. Annie listed plenty of reasons for it. Both as a person & exploring your feminine side. I hope these blogs help you consider it as part of your feminine exploration!

Hugs, Jenna

 

[Marty Fisher]

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.

WOW!!! Do you know how many of us closeted married sissies would LOVE to be married to a woman like you?!? Each and every one of us!!!!!!!! Your hubby is a lucky sissy!

 

[Iwantitnowpleas]

This happened about 10 months ago. I think that ship has sailed, I'm pretty sure neither of us wants to go through that again. She had seemed so okay with it when it was only an idea. Reality so often doesnt live up to imagination.

Now hiding a wedding dress....well after I place it ib the garment bag I caeefully fold it then place it in an old suitcase that then is hidden in our cavernous attic.

Part of me wishes I hadnt started reading this thread. The old urges have resurfacedas strong or stronger than ever.

That is just terrible. How long ago was this? I would encourage you to revisit that and explain to her that you need her support. How did you come out to her? I mean, are you just a cross-dresser to her? Explain how important and amazing her acceptance was when you first told her and you want to continue to share this with her support but admit that you're fragile about how you look. Maybe she can suggest little ways to reduce how much you "just look like you"? Better fitting clothes? More strongly feminine clothes? Did you do anything besides the clothes when you dressed in front of her? A wig, makeup, breast forms or something to give you a chest, heels, any or all of these would help you feel and look more feminine. She could help you master any or all of them as well.

Just too sad to be accepted and then lose it. Let me know if you talk to her again or want any other suggestions.

I will say that my hubby had a similar experience with a platonic female friend who was letting him order packages to her house. He bought some latex, thigh high boots (not really his style but he wanted to try them). They weren't a great fit and she admitted they looked like fishing waders. He told me that it wasn't a good feeling but he knew she was being honest with him.

 

[CaffeinatedHub45]

What an amazing list! I've done some, but this is a definite check list of more things to do. My wife is already talking about the shopping tasks.

 

[Easyvirtue]

I can’t stop thinking about this list. My wife will not tolerate my fetish any longer, but I’m so sexually charged by reading this list I’m going to indulge myself because I deserve it!

 

[SweetAnnie40]

I can’t stop thinking about this list. My wife will not tolerate my fetish any longer, but I’m so sexually charged by reading this list I’m going to indulge myself because I deserve it!

Be careful, be discreet, but enjoy your girlie self, sweetie.

 

[Easyvirtue]

Be careful, be discreet, but enjoy your girlie self, sweetie.

Thanks for your encouragement! XOXO

 

[dawndavis66]

What a Fun List!

I think I did pretty well on this list:

L
1,2,4,6,7,8,9,10

F 1,2,3,4,5,6*,7,8,9,10,11,18,19,20,21,21,23,27,28,29,30,31,32,33*,34,35,42,43,44,48,49,50,51,52,53,54,55,56,66,67,69,70,71,72,76,77,78

E
1,4*,12,13,15,16,17,19,20,21,24,25,32

S
2,12,13,14,

A
1,2,3,4

I think this adds up to 75.5

F6 bra buying - recommend Lane Bryant. Good experiences.
F33-35 -- Ankle strap is spot on. Learned that the hard way.
E4 -- pretty smooth all over but still have hair in pits, brows are trimmed but not shaped, and stubble on calves and shins. Gave myself a half point.

 

[Easyvirtue]

What was the experience at Lane Bryant like. Did you let them know you were there for yourself? They have some beautiful bralettes I’m looking to purchase.

 

[dawndavis66]

What was the experience at Lane Bryant like. Did you let them know you were there for yourself? They have some beautiful bralettes I’m looking to purchase.

Great experiences.
Once as a guy. She fit me for a bra despite not being certain what size my inserts were. She measured me asked me questions about their size and recommended a D cup. I tried on a 38d in dressing room and it fit well. She was right on cuo size as my forms fit perfect.
Second time I was fully femme. Measured, used room, etc. All good. So I bought panties too at checkout.

 

[SweetAnnie40]

Great experiences.
Once as a guy. She fit me for a bra despite not being certain what size my inserts were. She measured me asked me questions about their size and recommended a D cup. I tried on a 38d in dressing room and it fit well. She was right on cuo size as my forms fit perfect.
Second time I was fully femme. Measured, used room, etc. All good. So I bought panties too at checkout.

My hubby has had excellent experience with Lane Bryant and Torrid in particular. Very supportive of cross-dressers, could use changing rooms, got advice, measurements. Top notch.

 

[SweetAnnie40]

I think I did pretty well on this list:

L
1,2,4,6,7,8,9,10

F 1,2,3,4,5,6*,7,8,9,10,11,18,19,20,21,21,23,27,28,29,30,31,32,33*,34,35,42,43,44,48,49,50,51,52,53,54,55,56,66,67,69,70,71,72,76,77,78

E
1,4*,12,13,15,16,17,19,20,21,24,25,32

S
2,12,13,14,

A
1,2,3,4

I think this adds up to 75.5

F6 bra buying - recommend Lane Bryant. Good experiences.
F33-35 -- Ankle strap is spot on. Learned that the hard way.
E4 -- pretty smooth all over but still have hair in pits, brows are trimmed but not shaped, and stubble on calves and shins. Gave myself a half point.

Looks like you've been having a very focused sissy lifestyle and I'm sure enjoyed it all the way. How many (approximately) made you feel aroused vs. how many actually got your clit stiff vs. how many did not arouse you? Just wondering.

 

[dawndavis66]

Looks like you've been having a very focused sissy lifestyle and I'm sure enjoyed it all the way. How many (approximately) made you feel aroused vs. how many actually got your clit stiff vs. how many did not arouse you? Just wondering.

Hi Annie, thanks for responding.
I am not sure focused is the right word as I only get to dress up occasionally. But, over the years I have built up a bit of a wardrobe despite several purges. I have gained some confidence in makeup and if not for COVID I would have continued expanding or exploring my horizons.

To answer your question. I would say all aspects arouse me. Certain processes more so than others -- the act of putting on makeup -- hard. Rolling stockings up leg -- hard. The rush seconds before getting out of the car or opening a closed door -- hard. Air flowing up skirt or dress -- hard.

Some activities are just normal now so I am not conscious or I am occupied by tasks at hand -- like wearing things under my boy clothes.

 

[Willieceedee]

Thanks for the list Annie! Like some of the contributors, I have done several things on the list.

I think the most amazing thing of all for me, was once I started to dress up, I found it was an incredible amount of work. From shaving my body and legs, to doing make up, and then dressing. (My goal was to become passable...not going to happen!). Then the shopping. OMG that was exhausting until I found the right stores and my dress sizes. I can see fun side of shopping and finding the right outfit.

Two recommendations;

First is shopping. I took a tip off another site and went to the Goodwill. There are alot of nice outfits for darn cheap. Yah you should wash them first. But if they are not the right size, you dont spend and arm and a leg. I started there. The sales girl was helpful too. I said I was looking for stuff for my wife. I think she saw through the act but was polite. I got all sorts of dresses, slacks, tights and yes they do have underwear and lingerie. I even found a wedding dress but it didnt fit.

Also accessories. They really make an outfit. Help you feel more feminine. Cheap jewelry, a purse.

 

[SweetAnnie40]

Thanks for the list Annie! Like some of the contributors, I have done several things on the list.

I think the most amazing thing of all for me, was once I started to dress up, I found it was an incredible amount of work. From shaving my body and legs, to doing make up, and then dressing. (My goal was to become passable...not going to happen!). Then the shopping. OMG that was exhausting until I found the right stores and my dress sizes. I can see fun side of shopping and finding the right outfit.

Two recommendations;

First is shopping. I took a tip off another site and went to the Goodwill. There are alot of nice outfits for darn cheap. Yah you should wash them first. But if they are not the right size, you dont spend and arm and a leg. I started there. The sales girl was helpful too. I said I was looking for stuff for my wife. I think she saw through the act but was polite. I got all sorts of dresses, slacks, tights and yes they do have underwear and lingerie. I even found a wedding dress but it didnt fit.

Also accessories. They really make an outfit. Help you feel more feminine. Cheap jewelry, a purse.

Great advice, Willie! Thanks for contributing.

 

[CaffeinatedHub45]

This thread has been in my head since I first saw it, and I shared it with my wife. I have started shaving every day again, and I'm not just talking my face

 

[SweetAnnie40]

This thread has been in my head since I first saw it, and I shared it with my wife. I have started shaving every day again, and I'm not just talking my face

What was your wife's reaction? Any suggestions for something I missed?

 

[Kate_part2]

I had a bf in college who liked to wear nylons but was too chicken to buy them. We'd go into the store together, look at them all, but I'd buy them. Looking back, I wish I would have explored more of this with him.

 

[Iwantitnowpleas]

I had a bf in college who liked to wear nylons but was too chicken to buy them. We'd go into the store together, look at them all, but I'd buy them. Looking back, I wish I would have explored more of this with him.

I remember in high school going into a drug store and buying pantyhose. I acted like they were for my Mom.

Goodwill, I have bought several pairs of cute shorts and jeans there.

I'm very thin, Forever21 became my fave. Buy online with free store pickup They have amazing sales! . I'm sure the girls working there figured me out. The store was in the mall and I would try and go in when different ones were at the counter. I'm wearing a cute V neck top and pink mimi skirt from there right now. (Wife is asleep)

Macy's also has free store pickup. I didn't use it as much (not as cheap) but I found the prettiest dress and swimsuit there.

 

[Willieceedee]

I finally had time to go through your list Annie, and got to 74. I never had the guts to go out as a CD, walk around in woman's clothes or go into a store and ask for help. I am no where near passible. I did have a female confidant who helped me. She was such a joy and far bolder than I. We once went into VS to have a look and made it plainly clear to the salesgirl who we were shopping for. It was both exciting and a bit embarrassing. I walked out with about $300 worth of stuff and she got the points!

 

[stargame]

I am going to try F74.
That sounds sexy.

 

[SweetAnnie40]

I am going to try F74.
That sounds sexy.

You'll have to tell us all about it.

 

[SweetAnnie40]

If you've done items on the list, tell us your stories. How did it go? When did you cum?