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Annie's Super Sissy Idea List!

DINKY PEG said:
A BIG THANK YOU SWEETANNIE40 for sharing your experiences and long list of sissy idea for budding sissies and the like. Will study the list contents carefully and use as best fit. thanks again xx Dinky
Click to expand...

You're welcome, Dinky. You are encouraged to see how many you've already done and post your "score" for fun. :)
 
If I counted right, I've done 110!!!


My List

L1. Get healthy. Nothing is sexier than someone who is taking care of themselves. (I've lost some weight recently so I'll count this one)

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.

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.

L5. See a therapist.

L6. Establish a budget.

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? (Wife know, doesn't like it. I've told several women as platonic friends over the years)

AND NOW FOR THE FUN STUFF... UNDERWEAR

F1. Figure out your sizes for women's clothing and lingerie.

F2. Go to a lingerie store or women's clothing store that includes intimates and explore the different materials, colors, cuts and shapes.

F3. Buy a pair of panties.

F4. Enjoy your panties.

F5. Put on women's panties.

F6. Buy a bra.

F7. Enjoy your bra.

F8. Put on the bra.

F9. Buy thigh high stockings or pantyhose.

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.

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.

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.

F67. Visit a lingerie store (like F66) but quietly admit to the salesgirl that you're buying for yourself.

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.

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.

F73. Go to all doctor and dentist appointments wearing lingerie instead of guy underwear.

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.

F77. Open up your breast forms package, read all the directions, shower and dry off, and then apply them.

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...

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).

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.

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).

E13. Visit an adult store. Get a feel for it (do you feel comfortable enough?). Ask the attendant for "toys for feminine play"

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.

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.

E18. Study how to be feminine. Start at the beginning like all girls: CosmoGirl, TeenVogue, etc.

E20. Visit lingerie, women's clothing, and fetish clothing web sites. Sign up for their email newsletter.

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.

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

E32. Walk in your high heels.

E35. Purchase women's perfume.

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.

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....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.

S20. Do a second sissy mistress call.

S21. Masturbate but don't cum.

SOME ADVANCED THINGS...

A1. Come out to a platonic female friend.

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

A10. Watch how women move when you are out in public.
 
SweetAnnie40 said:
Come on, girls... did nobody dress for Halloween?

Okay, easier question, what do you desperately wish you could have dressed up as AND to go where? AND to do what? ;) :devil:
Click to expand...

Well, if I had longer hair I would love to be gowned as a beautiful starlet from the golden age of Hollywood at a swank studio party.....something that leaves my shoulders bare....the thought of Katherine Hepburn wearing a man's suit telling me hw hot I looked....oh my
 
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Jerseyshore said:
Well, if I had longer hair I would love to be gowned as a beautiful starlet from the golden age of Hollywood at a swank studio party.....something that leaves my shoulders bare....the thought of Katherine Hepburn wearing a man's suit telling me hw hot I looked....oh my
Click to expand...

Nice!
 
SweetAnnie40 said:
Nice!
Click to expand...

TY....I mean Hepburn for crying out loud, looking like her tomboy self looking in my eyes, knowng like so many others in Hollywood that Kate preferred women.....If I was a woman who crushed on women all my life but never took the plunge....I would die!
 
After having it about a month, I finally did my mask treatment. It was a nice experience. My pores look great. Have to see if I can do it twice a week.
 
Okay, sissies, is there anything I've missed in the list? Surely there are other sissy deeds or fantasies I couldn't guess you sissies would like to do?
 
I don't know if this is the right thread but I didn't want to start a new one and I appreciate that Sweet Annie has given us sissies a welcoming place here on the forums to share.

I also thought this might spark some ideas for people on sissy things they might want to get so I guess it fits the Sissy Idea List theme. :)



I'm sure we all have several items that were *special* in our wardrobe collections based on how hard it was to get, whose it was, or its design. Just as a fun mind exercise, I'm going to bring up a few that really rocked my world and deserved to be saved from the purge cycle (but sadly weren't).

Nylon black bodysuit - I grew up calling them teddies but the industry seems to be inconsistent on that score. Like a one-piece swimsuit but lingerie. My favorites came from the 80s/90s era when nylon teddies with lace trim were pretty available in local stores (sadly not any more). I found this a few years ago at Torrid and must have bought 3 before they stopped carrying them. (Sigh, the disappointing flow of fashion). It had a sheer mesh that would be above the breasts and I could get it in my size. Loved those. Hmmm looking. Ah, someone is selling one used (https://poshmark.com/listing/Torrid...VjL3ACh2xswd-EAQYAyABEgLAxvD_BwE&gclsrc=aw.ds) Wish I was in lingerie-buying mode instead of considering the latest purge... not quite my size.

Satin g-string panties - I think women got over the 'satin' in their panties and went for more practical microfiber, or at least that's what all the stores seem to have done. You used to be able to get them (like the one in my avatar) fairly easily but they just don't carry them in the local stores anymore. You can find them on ebay still or get similar from sissy specialty websites (though I much prefer wearing something made for a woman, not something made for a man - it's really an integral part of my feminine experience).

Wedding dress - Probably the greatest find of my sissy 'career'. I discovered consignment shops and after visiting them about monthly for six months, I came across MY wedding dress. Satin, old-school style like when I was young and impressionable. The experience of getting the nerve to ask the female store owner if I could try it on, dressing in my panties, bra, thigh highs and garter belt before I went there, then wearing it in the store - still almost makes me swoon. I had that for a couple years even though it was quite difficult to hide in my house and I hated to not hang it up as it deserved. This picture is not the one I had but pretty similar in overall design: lots of satin, full arms, full chest coverage, several layers of crinoline to poof out the skirt. Mine had additional lace overlays over the breasts. Lost count of the number of times that dress, my lingerie, a big cock dildo and I had "wedding night"! (https://i.pinimg.com/originals/31/ce/75/31ce7571106b5380c7118f139c073770.jpg)

Red one piece swimsuit - To my shame, this was someone else's in college and I took it. I still feel bad about that knowing they aren't cheap. I never knew the name of the original owner so even wanting to anonymously compensate her was impossible after that year at college. One of my real regrets.... even though it brought me much sexual joy. It was a red, racerback one-piece women's swimsuit that actually fit me (not ever to be assumed). I was in a dorm with three other guys (common bedroom) but found a way to wear that to bed and strip down to it under the covers. Again, many a very intense sissy time was had in that poor girl's swimsuit: https://m.media-amazon.com/images/I/71V8-WGYFGL._AC_UL1500_.jpg

Satin Corset - This is the one that I never actually bought but will always remain as a favorite memory. I've likely told this story before here or elsewhere but I was traveling for business to Washington DC and there was a store called Dream Dresser. It was a straight-up fetish store and had sissy dresses hanging on the racks, corsets, bondage gear, etc. I didn't have much cash I could privately spend on such things but I did go there wearing my panties to check it out. The girl working there helped me try on a corset, telling me to strip to my underwear, and never commenting on the erection I had in my red satin panties. She put it on me and the shortness of breath/compression/and bodyshaping were amazing. She told me how to put it on if I was doing it by myself. I couldn't afford to buy it but made sure I bought some nylon bloomers and sissy panties. Sadly they closed before I could get back with a stock of cash. I did eventually get another corset elsewhere and loved wearing it with a satin sissy dress I had at the time by the way if gave me a feminine figure and made the dress look sexy hot. It looked fairly similar to this, not quite as much ornamentation on the waist but full breast coverage: https://www.unitedcorsets.com/media...5683624a9/e/l/elegant-pink-satin-corset-1.jpg

I'll likely think of something else eventually but I'll add that later...
 
Gemsissy said:
I don't know if this is the right thread but I didn't want to start a new one and I appreciate that Sweet Annie has given us sissies a welcoming place here on the forums to share.

I also thought this might spark some ideas for people on sissy things they might want to get so I guess it fits the Sissy Idea List theme. :)



I'm sure we all have several items that were *special* in our wardrobe collections based on how hard it was to get, whose it was, or its design. Just as a fun mind exercise, I'm going to bring up a few that really rocked my world and deserved to be saved from the purge cycle (but sadly weren't).

Nylon black bodysuit - I grew up calling them teddies but the industry seems to be inconsistent on that score. Like a one-piece swimsuit but lingerie. My favorites came from the 80s/90s era when nylon teddies with lace trim were pretty available in local stores (sadly not any more). I found this a few years ago at Torrid and must have bought 3 before they stopped carrying them. (Sigh, the disappointing flow of fashion). It had a sheer mesh that would be above the breasts and I could get it in my size. Loved those. Hmmm looking. Ah, someone is selling one used (https://poshmark.com/listing/Torrid...VjL3ACh2xswd-EAQYAyABEgLAxvD_BwE&gclsrc=aw.ds) Wish I was in lingerie-buying mode instead of considering the latest purge... not quite my size.

Satin g-string panties - I think women got over the 'satin' in their panties and went for more practical microfiber, or at least that's what all the stores seem to have done. You used to be able to get them (like the one in my avatar) fairly easily but they just don't carry them in the local stores anymore. You can find them on ebay still or get similar from sissy specialty websites (though I much prefer wearing something made for a woman, not something made for a man - it's really an integral part of my feminine experience).

Wedding dress - Probably the greatest find of my sissy 'career'. I discovered consignment shops and after visiting them about monthly for six months, I came across MY wedding dress. Satin, old-school style like when I was young and impressionable. The experience of getting the nerve to ask the female store owner if I could try it on, dressing in my panties, bra, thigh highs and garter belt before I went there, then wearing it in the store - still almost makes me swoon. I had that for a couple years even though it was quite difficult to hide in my house and I hated to not hang it up as it deserved. This picture is not the one I had but pretty similar in overall design: lots of satin, full arms, full chest coverage, several layers of crinoline to poof out the skirt. Mine had additional lace overlays over the breasts. Lost count of the number of times that dress, my lingerie, a big cock dildo and I had "wedding night"! (https://i.pinimg.com/originals/31/ce/75/31ce7571106b5380c7118f139c073770.jpg)

Red one piece swimsuit - To my shame, this was someone else's in college and I took it. I still feel bad about that knowing they aren't cheap. I never knew the name of the original owner so even wanting to anonymously compensate her was impossible after that year at college. One of my real regrets.... even though it brought me much sexual joy. It was a red, racerback one-piece women's swimsuit that actually fit me (not ever to be assumed). I was in a dorm with three other guys (common bedroom) but found a way to wear that to bed and strip down to it under the covers. Again, many a very intense sissy time was had in that poor girl's swimsuit: https://m.media-amazon.com/images/I/71V8-WGYFGL._AC_UL1500_.jpg

Satin Corset - This is the one that I never actually bought but will always remain as a favorite memory. I've likely told this story before here or elsewhere but I was traveling for business to Washington DC and there was a store called Dream Dresser. It was a straight-up fetish store and had sissy dresses hanging on the racks, corsets, bondage gear, etc. I didn't have much cash I could privately spend on such things but I did go there wearing my panties to check it out. The girl working there helped me try on a corset, telling me to strip to my underwear, and never commenting on the erection I had in my red satin panties. She put it on me and the shortness of breath/compression/and bodyshaping were amazing. She told me how to put it on if I was doing it by myself. I couldn't afford to buy it but made sure I bought some nylon bloomers and sissy panties. Sadly they closed before I could get back with a stock of cash. I did eventually get another corset elsewhere and loved wearing it with a satin sissy dress I had at the time by the way if gave me a feminine figure and made the dress look sexy hot. It looked fairly similar to this, not quite as much ornamentation on the waist but full breast coverage: https://www.unitedcorsets.com/media...5683624a9/e/l/elegant-pink-satin-corset-1.jpg

I'll likely think of something else eventually but I'll add that later...
Click to expand...

Great post.

For me, it has to be the first and still only real quality wig. I got it at a higher end wig store and it set me back some real money. My funds for this activity come from leftover cash from things that occur in my other life. So it takes a bit of time to squirrel away money for an expensive wig. I treasure it. Take really good care of it. And wear it for more special occasions rather than a short in-bedroom selfie experience.
 
Looking for bright spots in the pandemic, I have a couple sissy ideas for you girls to try.


1. Put on lipstick under your mask and go out in public and do several errands.

2. Put on full makeup and wear your mask... not too many people should notice ;)

3. Put in a ball gag under your mask and go out in public where you pass by or are near women.

4. Put a vibrating butt plug in your pussy, turn in on random or low pulse, put on full lingerie and then your public clothes. Go run as many errands as you can before you cum in your panties.

What have YOU dared to do or wish you would?
 
SweetAnnie40 said:
Looking for bright spots in the pandemic, I have a couple sissy ideas for you girls to try.


1. Put on lipstick under your mask and go out in public and do several errands.

2. Put on full makeup and wear your mask... not too many people should notice ;)

3. Put in a ball gag under your mask and go out in public where you pass by or are near women.

4. Put a vibrating butt plug in your pussy, turn in on random or low pulse, put on full lingerie and then your public clothes. Go run as many errands as you can before you cum in your panties.

What have YOU dared to do or wish you would?
Click to expand...

Some good ones to try.
 
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