Annie's Sissy Help Line

Hello all you beautiful gurls, sissies, crossdressers, and transvestites!

Becoming feminine and enjoying sexual pleasures is a huge fetish for men. My husband is a confessed sissy so I've learned quite a bit and learned to appreciate how sexy a feminized man can be. I've been pretty open about this in my personal thread (Annie's Room: http://forum.literotica.com/showthread.php?t=1476585) and it has attracted a lot of interest from you beautiful sissy boys. In an attempt to give you all what I can and not make answering your PMs a full-time job, I'm going to post advice, suggestions, and answers to questions that I receive.

Everyone's story is a little different but so much of it is the same... desired this since puberty, married, never told wife and you think she probably would divorce you, want it more and more over time, often also think about cocks but not the men they are attached to, want to be encouraged/forced by a beautiful woman.

Hopefully what we discuss here can help you with your journeys and I think we'll have fun along the way.

So post your questions and I'll answer them all to the best of my ability (or ask my hubby when I'm stumped and need a sissy's perspective).

Home of Frequently Asked Sissy Questions

Will you make me a sissy, tell me everything to do, make sure I cum a lot, while I respond with maybe a short sentence pushing you to do more?

Sorry to start with the harsh one, but the answer is no on many levels. While I feel I am a kind and generous person and I do enjoy playing around on literotica, I tend to reserve my attentions for those who participate equally and honestly are other women. Asking anyone on here for something is something you have to be polite about and make sure you are reciprocal otherwise you're just being rude wanting to jack off in your panties. You don't need me for that.

I'm a sissy and really want to explore my bisexuality. My wife doesn't know and says she doesn't understand gay people. What can I do?

Well, if you can't constrain these desires to fantasies and masturbation, I think you're looking at a hard road. Are you willing to cheat on your wife to satisfy these desires? Even with as much as I focus on it, sex is a fraction of your life. Are you willing to throw the rest away for some orgasms? The more honest approach would be to tell her as sensitively as you can. Natural questions (whether she asks them or not): "are you gay?" "Do you not want me anymore?" "Are you already cheating on me with men?" "What could you imagine I would do with this information?" - she's not there to play a role in your fantasies so you need to focus on your connection to her, that you have desire for her and always will, but you have more as well. You understand that it doesn't make sense to her and it isn't something you chose. You might be best off just telling her and letting her know that you'll never act on anything without her full support. (Okay, that last bit is manipulative... what spouse doesn't want to support their spouse fully? That's the argument that got me on my husband's side and helping him with all his femme stuff).

What is a Sissy?

I try not to get anal about terms and semantics so a Sissy is whatever you want it to be. I think declarations of what is or is not a sissy are kind of rude. Embrace what you want and have fun.

Okay, what is a Sissy to you?

In my book (and this is basically all modeled after my husband who claimed the term sissy for himself long ago), a sissy is obsessed with the feminine sexual experience; being desired, being beautiful/sexy, wearing attractive and sensual clothing, wanting to feel like a woman in bed. So that includes wearing women's underwear, dresses, etc etc but not fetish-wear like "panties made for men". The whole point is wearing something made for a woman. Makeup, breast forms, body shapers can help the illusion go further. In my husband's case it also includes strapon sex with me "making" him suck my strapon cock and then me fucking him.

There are so many "optional add-ons", some my husband has, others he doesn't. Hubby loves cum play, gobbling his own cum, and swallowing cum from another man. He loves playing with another man's cock (sucking, being fucked). He is not interested in kissing another man or having a relationship with another man. He enjoys "lesbian play" where we ignore his cock and are two women in bed together... which is frankly how we connect best and have loving relations. We've played with some bondage, some chastity, some denial, some cuckolding. He's enjoyed them all but doesn't push for any of that to become a permanent part of our experience.

Other sissies I've talked to get into other areas that Hubby and I do not: "worn" panties/bodily smells, tampons/pads, permanent chastity, deep humiliation, small penis humiliation, etc.

how do i become a sissy?

Hmmm, interesting question. I can answer a couple different ways. I think guys become sissies very early on when some event or happenchance ties their erotic development to women's underwear. Maybe it is their mother's or a sister or a friend but all those rushing hormones 'imprint' in a way on the sight, feel, or something smell of those things. I think this often happens before the guy even begins to realize they are in puberty and feeling sexual. Once it starts, every masturbation rubbing sister's panties leads to wondering and finally trying them on, then every masturbation wearing her panties... just a huge pleasure reinforcement loop.

If you're asking, what do sissies do so you can do that, I would say primary is developing a desire and then an undeniable need to wear girl's/women's panties. This evolves to trying other things: bras, stockings, camisoles, (the rest of the lingerie world), dresses, heels, makeup, etc. etc. etc. There are lots of other things to do but that seems to be the core experience for any sissy I've talked with.

How women feel about a man (who is otherwise quite manly in mannerisms in public) having a private secret like this?

Naturally, I've been empowered to speak for ALL WOMEN EVERYWHERE! Okay, I can only give you my view. It can be a shock. The longer it has been a secret, the bigger the shock. After the shock, I guess it comes down to how much being with a traditional, cis-male partner is important to her own self-image. A deeply religious woman might have a very difficult time imagining that you could be both a 'regular guy' in public but want to be a lingerie-wearing sissy in private. I've talked to enough people to have heard the stories about divorces which sadly are all too common when a man has hidden this for a long time but gets caught or confesses. Really the hiding and secrets can be the worst part because that attacks her trust in you which is a very deep thing, and something when damaged is very hard to repair. It would be much better if you let her know that you enjoy feminine stuff but it isn't the only thing that arouses you and it has nothing to do with being attracted to and aroused by her. If she feels you've been honest and not hiding anything and that she doesn't need to deal with it unless she wants to, that's probably the lowest pressure scenario. Dealt with while you're dating or courting is really the best, before she makes a big commitment (marriage, merging lives, children, etc.). It is a risk that it will be a deal-breaker for her, but unless you're willing to hide and do without it for most of your life, you have to take that risk.

An important part is how much you want it to be a part of your sex life with her. Probably best case would be an occasional fun time you enjoy and hope she has fun with it too. Make sure lovemaking is most about connecting with her, showing her your love and desire for her through your sexual actions, and never making her seem second class to a fetish item. Introduced this way, you might get to enjoyable levels of acceptance (her buying you panties as a treat for example).

If you want her to be your dominatrix and force you to dress like a slut and pimp you out for cocks... well, that should probably be the starting point for your relationship and then see if she wants to do dinner and a movie after the sex show is over.

How can I get my conservative spouse on board?

Continuing from the previous question, but assuming a very conservative wife... I think all those thoughts are still valid. You have to be very clear about what putting on panties (or whatever) means to you and what you enjoy. She probably won't understand it but if she can see that it is harmless, will remain in private, she doesn't have to participate, it won't risk the family because you're making dates for sex outside the marriage, etc., you have a chance. Sadly, I realize that most of you sissies really crave a lot of experiences and her simple acceptance of you instead of a "holding her nose' avoidance can be one of the most powerful experience. You might get lucky and she comes to accept some level of it with you but you have to understand if telling her your sissy secrets is so important that you will risk divorce or worse. I could say its just sex but sex plays a huge part in my life so I get that it is a hard choice. If you really love each other, I believe you'll find a way to stay together with it whether that is all you dreamed of or not.

Any advice or recomendations for sizing & find yoga pants for running with a more gender nuetral look, but definite feminine feel?

Fit with women's clothing on men is always tough. Hubby learned long ago that he can try things on over his panties in the women's fitting rooms. He is always very polite and responsible and never makes it a sex thing and they just want the sale. At least in the U.S. it has been years since he got anything but full support from the sales women. So for fit, I highly recommend trying them on that way. As to gender neutral, that's a bit of a matter for taste, I guess. You could go basic black but that is sort of the girl's style these days. If you go away from that, they are pretty much trying to be athletic + girly so the accents tend to be neon colors or such. There is a design I see women wear that could be unisex to the casual observer which has panels of either semi-transparent or just a lighter color grey/grey-brown with a basic black legging. Maybe give those a try?

I want my wife/SO/girlfriend to say certain things to me during sex but she's reluctant/it feels silly/etc. How can we find a compromise that get me the thrills I'm craving?

(Kudos to BuckyDuckman for the question and advice, paraphrased here)

Have your wife ask easier, more open-ended questions that don't require her to say things she isn't comfortable with. "Do you like that?" "Does that feel (or taste) good?" She might feel a little self-conscious or embarrassed but that isn't a bad thing.

As she gets comfortable, she can ask leading questions like: "What are you?" which allows you to reply with whatever turns you on: "I'm a cock-sucker." or "I'm a sissy slut." or whatever really turns you on.

I looked on Amazon for a skirt but I'm not sure what might work best for me. I admit ( as you can see in my profile) that I'm a chunky girl - i have about a 48in waist (5'9, 255). I was wondering if there was a type of skirt , like a 1 size fits all wrap around skirt that i could get or if you have any suggestions on type and size of skirt that might work for me.

Hmm, for your body type generally I would suggest creating long vertical lines and not wearing a skirt which would create a distinct line around the feature you want to minimize. Of course you have your spanx and other shaping underwear you could wear to improve your situation (just like a real woman) or go all the way with a corset. If you go ahead with a skirt, I would suggest you get what turns you on the most rather than what might look best on you if you aren't going to be seen by anyone. If you are still focused on your appearance, go long, floor length and flowy. Short skirts and skirts with too much defined form won't be flattering. A flowing dress or skirt would hide the lower part of your tummy. If you wear size appropriate but large breast forms, they would gather the attention above your waist.

Why do you think i want to be a sissy fucktoy so bad ?

Well, that's really the BIG question, isn't it? Why do you sissies feel compelled to play with panties, dare to put them on, want to wear more and more feminine things, and eventually have sex like a girl?

I suppose psychologists would have their theories and I'm sure there are hundreds of books out there about how people develop fetishes, non-typical gender self-images, and such. My only credentials are living with a man for over twenty years who came out as a sissy three years ago and has been living his sissy life with my support (when we have privacy) since then. We've talked about it a lot. For him, when he was first experiencing puberty, he had no guidance or role model or anything to help him. This was even before the horrible teacher of the Internet (gasp)! So he had these nameless, formless desires along with a sense of being completely unattractive (he was heavy-set as a kid and had a terrible self image and no fashion sense). Somehow his mind got fixated on how attractive women and girls were. He wanted to feel attractive, to feel like someone might actually want to have sex with him. He wanted to feel what girls feel. He can't remember if that conclusion and early fumbling attempts to pleasure himself as he discovered masturbation came first or his first trip to his parent's bedroom and his mother's underwear drawer. At first it was rubbing his penis with a pair of full cut nylon panties. Eventually he put them on (again, feel like a girl) and fantasized about spreading his legs and lifting his dress on prom to ... well things were still a bit fuzzy for him but you get the idea. Some sense of not wanting to be caught/ being rushed became erotic and soon he would put on every pair of his mother's panties he could and the struggle in all those panties to pull them down and pull them up and risk of being caught all became very mixed in what was getting him to cum. Ever since then, he's had all the typical sissy attractions, fantasies, and lots of real world sissy experiences. He'd never actually touched another cock until two years ago when we agreed to let him have that experience and found a male friend of a friend who was bisexual and interested. Before the pandemic and before our son and his girlfriend moved back into the house, we would have play times weekly with our friend with hubby sucking and being fucked at first and later, I would decide that some nights were my turn. But I digress.

Some combination of early thoughts trying to figure out this sex thing and choosing to look into panties started it all. Then every time he masturbated in panties or had sissy fantasies, it all just reinforced itself. (Frankly, I'm surprised that we had as "normal" a sex life as we did for the first ~20 years of our marriage.)

It isn't an answer but maybe my husband's experience might provide some perspective. In the end, it doesn't matter why. I haven't talked to a sissy yet who could seriously say they could give it up tomorrow and never think about it the rest of their lives. Sissies are hooked and hooked hard. Luckily it is a rather sexy addiction that causes no health problems, doesn't have to be expensive, and can be done in private for the most part.

Do you have any suggestions of maybe some type of perfume that i could buy to help me smell pretty ? Preferably something available at the drug store, unless you can convince me get something at Macy's or maybe Bath and Body Works.

The weakest/most subtle class of perfumes are eau de toilette so you should probably stick to those if you're concerned about a spouse or others smelling your feminine scent. I'd advise putting a tiny amount somewhere that isn't normally exposed (nipples?) but you can lift your shirt and smell to please yourself.

As to which perfume, there are literally hundreds of varieties at all price points. Go where you prefer to shop and see which scent appeals to you. Try to go subtle. (Most men seem to like the overpowering, cheap "stripper scents"). Using just a tiny amount that only you know about should be lovely. If you live alone, have privacy, etc. you can indulge more traditionally with a light dab behind each ear or on each wrist. Be ready to shower to unperfume yourself.

SweetAnnie, please help a gurl out who won’t pass as a woman. How can I truly embrace my feminine side. I have no one to share my feelings and desires with. I long to have a girlfriend to confide in, shop with, be my guide as I embrace my gurly side.

Feeling feminine is how you think about yourself. Don't worry about passing some arbitrary test in the mirror. Do things that make you feel feminine. Wear things you find very feminine. Pamper yourself in feminine ways. Most of the items in my Super Sissy List aren't about passing as a woman. If dressing up in satiny lingerie, dresses, high heels, and feeling a big cock dildo thrusting in your pussy makes you feel super feminine (and how could it not? then do that. So you don't need a 'partner in crime' to feel feminine.

You're welcome to share your feelings and desires here in my Sissy threads and I hope I (and the others) can provide you some level of support. Finding a girlfriend to embrace your girly side is a challenge certainly. If that is going to be front and center in your potential relationships, then you have to start with that. Seek out sexually open and gender-fluid communities. Whenever the pandemic is over, attend more fringe events/festivals. Make friendships without expectations. Be who you are inside. When you meet someone, there won't be any anguish about hiding yourself or whether they care about it. Really that's the best way I think it could possibly be approached for a sissy.

Next question?

Speaking of Humiliation

Humiliation can be part of the sissy experience, reinforcing and enhancing the feminization experience by also making it an emasculating experience. Hubby and I haven't played with this much because I personally find it difficult to say those things to the man I love even if I know it gives him pleasure.

Here is a little something you might enjoy if you like humiliation...

"Thank you for being so honest. It is a rare person who could admit how totally inadequate they are to please women and how utterly unmanly they are. You are clearly a total sissy: not a man and not a woman. Every time you think of panties or when you dare to put women's lingerie on yourself, you are confirming you are a sissy, not even a pathetic man but just a simpering sissy whose cock barely shows in panties. Sissies deserve to be emasculated... shaved smooth, dressed in clearly sissy clothes... nothing a woman would wear but satiny sissy dresses... I'm sure I'm just confirming what you know deep down is the complete and utter truth of you. A real man would never put on panties. A real man makes a woman moan when he fills her with cock. A real man has confidence and carries himself like a man. You're none of those. And when you put on panties and when you read these words, hear me telling you these things, you can't help but rub your little clitty, squirm and squirt, getting your panties all wet."

Hello Annie, thank you for sharing in this way, your interest in and desire for men who enjoy wearing feminine clothing is, in my experience, a rare thing in a sexually attractive woman and your ever expanding PM inbox is a result! I think here is a good solution, and I will check in and enjoy the posts I know!

The range of sissy 'definitions' is interesting but perhaps a distraction. In my youth sissy was quite a derogatory term, someone who didn't stand up for anything, didn't like 'masculine' things and looked and sounded a bit girly to all those burly blokes... no political correctness in the mining towns of Yorkshire!

My own place on the continuum? I love the sensations that lingerie, skirts and heels all bring, so different and slightly taboo of course. I do have wigs and makeup but I rarely go there, am not that convincing unless I spend ages and usually it adds nothing to the sensual feelings that are generated by a nice dress or a swishy skirt glowing around nylon covered thighs. I am only attracted to the female form... something that many find odd, but that's the way it is! We all have a niche on the continuum and that is just fine and dandy!

Pretty sure this thread is going to explode....mmmmmmmmm

LucyCanyon said:

Hello Annie, thank you for sharing in this way, your interest in and desire for men who enjoy wearing feminine clothing is, in my experience, a rare thing in a sexually attractive woman and your ever expanding PM inbox is a result! I think here is a good solution, and I will check in and enjoy the posts I know!

The range of sissy 'definitions' is interesting but perhaps a distraction. In my youth sissy was quite a derogatory term, someone who didn't stand up for anything, didn't like 'masculine' things and looked and sounded a bit girly to all those burly blokes... no political correctness in the mining towns of Yorkshire!

My own place on the continuum? I love the sensations that lingerie, skirts and heels all bring, so different and slightly taboo of course. I do have wigs and makeup but I rarely go there, am not that convincing unless I spend ages and usually it adds nothing to the sensual feelings that are generated by a nice dress or a swishy skirt glowing around nylon covered thighs. I am only attracted to the female form... something that many find odd, but that's the way it is! We all have a niche on the continuum and that is just fine and dandy!

Click to expand...

Thanks, Lucy. Agree that all gurls and sissies have their own combinations of factors that are either part of it or not part of it and people have the right to own any term they want. Using it as short-hand to a sort of 'average' of this sort of lifestyle is inevitable and okay as long as people clarify when it is needed.

SweetAnnie40 said:

Thanks, Lucy. Agree that all gurls and sissies have their own combinations of factors that are either part of it or not part of it and people have the right to own any term they want. Using it as short-hand to a sort of 'average' of this sort of lifestyle is inevitable and okay as long as people clarify when it is needed.

Click to expand...

I'm guessing that the fact you became such a beacon for the Sissy community tells us that there is a real need for this thread - not another picture thread, but somewhere where we can talk openly about fears, experiences, emotions, concerns and become comfortable in our own skins

In many ways sissy can be a lonely place to be, as females / wives / girlfriends don't always understand. There are the lucky ones (and I am one) who have someone who embraces and builds on my sissydom, but there are more who have to deal alone, and many who can't talk openly about it

Sure we all have our own 'flavor' of sissy, but that's cool, as you say there are many many common themes, and variety is the spice of life!

So thank you Annie, in a few days of being back you have started what I hope will be one of the most useful, supportive threads, and I have already seen posts by others - LucyCanyon, SissyTrish etc who also have a lot to give

SweetAnnie40

I was just thinking of you recently...

I was going to send you a PM.

Love you!

Paris.

SweetAnnie40, so glad to see you back.

Subscribed. Eager to learn from others!

Thanks for starting this thread. I will visit here often as most of the things you said in your opening apply in some way to me. Not all, but most.

Iris_66 said:

I'm guessing that the fact you became such a beacon for the Sissy community tells us that there is a real need for this thread - not another picture thread, but somewhere where we can talk openly about fears, experiences, emotions, concerns and become comfortable in our own skins

In many ways sissy can be a lonely place to be, as females / wives / girlfriends don't always understand. There are the lucky ones (and I am one) who have someone who embraces and builds on my sissydom, but there are more who have to deal alone, and many who can't talk openly about it

Sure we all have our own 'flavor' of sissy, but that's cool, as you say there are many many common themes, and variety is the spice of life!

So thank you Annie, in a few days of being back you have started what I hope will be one of the most useful, supportive threads, and I have already seen posts by others - LucyCanyon, SissyTrish etc who also have a lot to give

Click to expand...

Thanks, Iris. I do try to share what I can and give support when I can. Hope this thread helps people.

Paris54 said:

I was just thinking of you recently...

I was going to send you a PM.

Love you!

Paris.

Click to expand...

Hi Paris! Nice to hear from you again. Drop me a PM any time. Kisses

BlackSatinKnight said:

SweetAnnie40, so glad to see you back.

Click to expand...

Thanks, BSK. Idle question: what's the most satin you've worn at one time? Is it just panties or have you slipped into satin lingerie, satin pajamas, a satin kimono?

irishblade said:

Subscribed. Eager to learn from others!

Click to expand...

Thanks, irish. Any questions for the FAQ?

amysboytoy said:

Thanks for starting this thread. I will visit here often as most of the things you said in your opening apply in some way to me. Not all, but most.

Click to expand...

You're welcome, ABT. Feel free to send me questions for the FAQ.

SweetAnnie40 said:

Thanks, BSK. Idle question: what's the most satin you've worn at one time? Is it just panties or have you slipped into satin lingerie, satin pajamas, a satin kimono?

Click to expand...

Panties and a satin camisole with a garter belt and sheer stockings. All under my street clothes for work.

BlackSatinKnight said:

Panties and a satin camisole with a garter belt and sheer stockings. All under my street clothes for work.

Click to expand...

I'm sure you enjoyed that very much. Thanks for commenting.

SweetAnnie40 said:

I'm sure you enjoyed that very much. Thanks for commenting.

Click to expand...

Loved it, wish I had the opportunity to be as bold again. It was a “perfect storm” where I had the freedom to dress that way. I’ve worn panties and even pantyhose since, but never that delicious a combination again.

BlackSatinKnight said:

Loved it, wish I had the opportunity to be as bold again. It was a “perfect storm” where I had the freedom to dress that way. I’ve worn panties and even pantyhose since, but never that delicious a combination again.

Click to expand...

How often do you get to dress in lingerie when you go out?

BlackSatinKnight said:

Panties and a satin camisole with a garter belt and sheer stockings. All under my street clothes for work.

Click to expand...

Sounds delightful, and I do a similar thing though not always with satin, sometimes lacy panties and cami, but it does feel good to have the secret knowledge of what's underneath.

I don't wear socks so anyone looking would see the nylons, often sheer black, anyone ever notice you?

Delighted to join

Hi,
Thanks for this thrilling opportunity to explore my sissy urges.
Norma

Iris_66 said:

How often do you get to dress in lingerie when you go out?

Click to expand...

Hi Iris, hope you are well!

Have been working back in my own office this last two weeks after a lot of frustrating home working... 6 days alone in my own room and yet to wear trousers, socks or indeed anything male below the waist! Great fun on video meetings!!

Having fun still?
Lxx

LucyCanyon said:

Hi Iris, hope you are well!

Have been working back in my own office this last two weeks after a lot of frustrating home working... 6 days alone in my own room and yet to wear trousers, socks or indeed anything male below the waist! Great fun on video meetings!!

Having fun still?
Lxx

Click to expand...

Hi Lucy

Glad to hear you are safe and well, and enjoying return to work

I took the opportunity to wear lingerie during lockdown, and so am the opposite to you, return to work = return to drab

It was a once in a lifetime to have all that time off, but offset with financial uncertainty and worry, but still positive, still here, and still enjoying weekends!!

New question added to the FAQ (second post in this thread)