Have you ever watched one of those videos where the cute-as-can-be sissy is sitting back on her knees, riding a dildo for all she’s worth, when all of a sudden her limp—or possibly caged—clitty begins to leak a little—or sometimes spurt a lot of—cum while she experiences one of those earth-moving sissygasms? Her post-orgasmic spasms appear to reverberate throughout her entire body?

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I don’t know about you, but I become extremely envious while watching her achieve something that I’ve always considered an unlikely, if not a near-impossible dream. These frustrating fantasies about having that elusive sissygasm is about to change for me—hopfully sooner, rather than later. I’ve decided I’m ready to have one!

The Definition of a Sissygasm

Before we travel too much further down this feminine-like orgasm path, let’s define what exactly a sissygasm is. Over the past year or so I have, more-or-less, moved past masturbating like a male in exchange for cumming more like a lady.

With my limp clitty tightly tucked downwards into the open-ended liner of my panties—like it is situated 98% of the time anyway—I gently rub (or ‘nub’ if you will) the underside tip of my panty-encased clit with one, meticulously manicured finger. Although this is an exquisitely feminine way to cum—much different than jacking it—it’s NOT a sissygasm (as we’re defining it here anyway).

Most would define a true sissygasm as a hands free orgasm, aka HFO. It is achieved from anal (sissy pussy) penetration only, typically from stimulation of the prostate gland/P-spot with a prostate massager, dildo or maybe even a real cock.

If you’re looking for a prostate-massager that will do the job, TooTimid has a really good selection of them.

Many, if not most, sissies report that achieving a sissygasm is not so easily accomplished and… I can certainly confirm that. Still, with practice, we sissies have more than ample video proof that it can be done.

The consensus of sissies (and others) who experience these types of orgasms on a regular basis is that once you are able to get off this way, the typical ‘manly’ ways to cum are relegated to the ‘inferior’ category.

A Sissygasm Disclaimer

As I write this, I’ve yet to experience my first real sissygasm so… what exactly qualifies me to write on the subject? In the truest sense, I’m not qualified one fucking bit at all. But, I have read and studied-up on sissygasms quite a bit. If you’re reading this, maybe you have too.

But more importantly, I’ve made a commitment to having my first girly-girl O, sometime in the not-to-far-off-future. In any case, by the time you wind reading this article, hopefully I will have been lucky enough to have had my very first sissygasm.

To that pleasurable end, I’ve purchased a Nexus Revo 2 rotating prostate massager. In addition, I’ve made a vow to myself to remain limp—with the help of limp clitty training hypno—and chaste until I finally do have that first sissygasm. Keep those pretty little fingers crossed for me sweetie!

Relocating Your Erogenous Zone

It appears that the main concept behind achieving a sissygasm is to psychologically move your erogenous zone back, from the base of your sissy clitty, across the perineum, to your sissy pussy. It’s imperative to STOP thinking of your smallish—and hopefully shrinking—penis as your primary, or even secondary sexual organ.

Are you a man or a sissy? Sissies don’t jerk their clitty’s so it’s time to come to terms with who you really are. How are you ever going to be able to cum like a girl if you continue to think and act like a man? I realize that this major shift in mindset—from M to F—is NOT for every sissy. It certainly wasn’t for me until fairly recently.

If you’re not willing to give up jacking off and fucking girls, then that’s perfectly okay. All it means is that you’re not yet ready to fully embrace womanhood and learn to cum like a lady.

Once you begin to mentally relocate your primary sex zone to your pussified ass, it’s time to support and enhance that feeling with something physical. That means sticking your favorite toy up your sissy pussy while refraining from touching that (preferably limp) sissy clitty.

BTW, TooTimid has a nice variety of dildos.

Setting Up The Sissygasm Scenario

Since we both know that our brains are the most powerful sexual organ, it makes sense that a sissygasm should begin in your head. Attempting to attack your P-spot with a dildo, trying to force an orgasm rarely works. Starting things off with a sexy scenario is the preferred way.

I like to get all dolled up; full make-up, bra, panties, nylons and heels. Then I begin to visualize my most favorite erotic fantasy through my mind. You may prefer to watch a video. Only after I’m physically, psychologically and sexily set-up do I insert the Revo 2 into my pussy.

It typically takes a genetic girl some time to get warmed up… and then even more time to eventually orgasm. It’s the same with us sissies. Enjoy the pleasure you’re allowing your sissy pussy to experience without harboring expectations that you need to cum. Let your mental fantasy run wild and see what transpires.

Achieving a sissygasm can be a challenging climb, especially while wearing heels. The first one may take awhile. However long it does take, my admittedly novice advice would be to just relax and thoroughly embrace, and enjoy the process. That’s how I’ve decided to approach things.

The Three P’s To Achieving a Sissygasm

• Practice
• Patience
• P-spot

Achieving a sissygasm on your first try is not the normal experience. For most sissies, and even real men, it takes a good amount of practice. That’s the first “P”, practice. Sissygasms should be treated just like any skill you would endeavor to master. It will take committed, consistent practice over a period of time to get good at them.

As I alluded to in the previous section, some patience will also be required. Move on from the narrow-minded, unfulfilling male mindset of getting sexual relief as quickly as possible. As a sissy, you want to bask in patient, pleasurable sexual excitement. Let your sissygasm happen—rather than trying to make it happen.

The third “P” to achieving a sissygasm is the P-spot that you will want to stimulate. Stick a finger up your pussy a couple of inches and you will feel a smallish, roundish ball that is located towards the front of the body. That’s your prostate gland. Every sissy’s P-spot will be in a slightly different place. With patient practice, you will eventually find where that seriously significant spot is.

What you use to stimulate your P-spot is a decidedly very personal matter. It could be a prostate massager—there are so many to choose from—or some sort of regular dildo. Some sissy’s have luck using just their finger. If you’re into men, maybe you can find a boyfriend who can hit your P-spot with a perfectly placed movement or motion.

Chastity and Sissygasm - The Dynamic Duo

If you’re the hopelessly impatient type, staying chaste for an extended period of time can speed up the sissygasm process. Depending on how old you are, that ‘extended’ period will vary. One week may seem like an eternity if you’re younger. An older sissy like me—who also listens to a lot of limp clitty training hypno—won’t bat a fake eyelash at a month.

As many sissies will arduously attest to, remaining in chaste mode—preferably with the help of a chastity device which you can find over at Oxy—for a prolonged period of time can create an undercurrent of ongoing desire that can be highly erotic in its own right.

Some would argue that this is the preferred state that any sissy worth her lingerie should be constantly striving for.

And when that elusive, mind-shattering sissygasm does eventually materialize, I’m thinking all that waiting will be worth it… and then some!

Sissygasm Update – July 2020

Since originally writing this article I’ve gained more understanding involving the process of achieving a sissygasm. If sissification is a process, then having a sissygasm should serve to re-emphasize that same word… process.

After years of perfecting the art of cumming like a man, I can personally attest that rewiring your brain and retraining your body to orgasm in a more feminine-like manner can be a daunting task.

When it comes to sissygasms, I’ve come to three conclusions…

1. You gotta be completely committed and dedicated to having one.
2. Although in theory it sounds like a good idea, staying completely chaste until it happens doesn’t necessarily work so well in real life.
3. It might be wise to find a ‘bridge’ type of orgasm—something between nubbing your clit in your panties and a full-on legitimate sissygasm.

I talk about practice earlier in this article. That translates to a metric ton of consistent and dedicated practice!

Remaining totally chaste for a lengthy (more than a month) period of time—for me anyway—turns up the sissy-sex-barometer to levels where it’s difficult to think about anything other than sissification.

Finding yourself in a never-ending erotically aroused state sounds nice (and it is), but it can seriously interfere with one’s ability to concentrate on the non-sissy parts of your life.

I recently found myself in that predicament—after three weeks of remaining chaste—I was too horny to think. I didn’t want to completely destroy the sissy erotic zone I was experiencing with an orgasm, but I felt the need to take at least a little of the edge off. But how?

While getting ready to practice yoga at home one day, I decided to lay down on my yoga mat in a plow position (on my back, legs positioned horizontally over my head) while naked. Just for fun, I wanted to see how close I could get the tip of my sissy clit to my mouth.

Since I was so incredibly horny, I couldn’t resist the temptation to reach up and very lightly diddle the very tip of my clitty between my thumb and forefinger. Partly because my nails happened to be long and painted that day, the sensation was incredible. Just an light flick my nail on the very tip of my clitty proved to be overwhelming.

I felt a modified orgasmic-like contraction and after 5 seconds or so, a small amount of semen began to drip out of my sissy-clitty, directly into my mouth. The scene was similar to the one above (except that it wasn’t a steady stream—and I’m not a blonde).

This continued about 6 more times in succession within the span of 30 to 40 seconds. It felt something like an drawn-out variety of a ruined orgasm—except strangely satisfying in its own, unique way.

Afterwards, although the sexual edge had subsided somewhat, I hadn’t lost all of my sissy mojo, only a small segment of it—which enabled me to now focus on other important aspects of my life.

The interesting thing is that after this protracted orgasmic experience, I definitely did NOT feel that I had, in any way, shape or form, just cum like a man. It felt deliciously all sissy.

Have I inadvertently stumbled upon some missing sissy psychological link that will serve as a bridge to eventually experiencing that elusive sissygasm? It’s way too early to tell… but I’ll keep you posted.

In Search of the Perfect Chastity Device?

If you think that a chastity device might help in keeping you chaste for and extended period of time (how could it not?), then you might want to check out my Sissy Chastiy Devices page. On it, I go over the many different types and styles of chastity cages that are available.

It can be said that sexy lingerie to a sissy is like whipped cream to strawberry shortcake. A sissy without at least one matching bra and panty set would be like an eskimo without an igloo. The truth is that sissies and lingerie go together like… okay, enough of the corny phrases already.

Seriously, lingerie is very close to the top of the list of ‘must have’ feminine attire as a sissy begins to accumulate a wardrobe. One problem is that lingerie, like most other women’s clothing, can be expensive for a girl just starting out on her sissification adventure.

Enterprising merchants have capitalized on the burgeoning sissy market so you will not find it difficult to come across several places online where you can buy stunning sissy lingerie. There are two main ways to go:

• Regular women’s lingerie
• Specialty sissy lingerie

Initially, you may be inclined to look past genetic girl’s feminine undergarments since most every sissy is painfully aware that girls are built different than boys. Women’s clothes are obviously not designed to fit a man properly. But we’re not talking regular clothing here—were interested in lingerie for sissies at the moment.

Just so you know, TooTimid.com is the perfect place to buy your lingerie.

The difference between the two being that bras, panties, babydolls, nylons and garter belts are, for the most part, smooth and stretchy. Their more-or-less elastic qualities will likely conform to your sissy body just fine. The advantages of choosing regular women’s lingerie over specialized sissy lingerie are:

• Greater availabilty
• Lower prices
• You’ll feel more feminine wearing lingerie designed for females

Of course there will be more bras and panties to choose from simply because there are a greater number of real girls compared to us sissies. A specialized sissy store caters to the exclusivity factor which, because of the perceived greater value, leads to sissy lingerie prices rising faster than a homesick angel.

There is certainly a case to be made for buying sissy stuff at a store that caters to sissies specifically but, when it comes to sissy lingerie, not so much.

What about the so-called sissy type of panties that are designed with a pouch or extra material so as to accomodate the presence of male junk. To me, that’s missing the whole point of sissydom.

Sissy Girl Etiquette Guide Pdf

Proper sissification necessitates showing a flat, feminine front which means tucking your sissy clitty back between your legs. A traditional pair of women’s panties, depending on the cut, will hold things back in place fairly nicely.

Bra’s of course are a different animal in that you can buy the type with pockets that are designed to hold breast forms. If you are to the point with your sissifcation endeavors that you are ready for breast forms, then a special sissy or crossdresseer store might be an appropriate choice for you.

From personal experience, there are many styles of bras—without pockets—that will work perfectly with breast forms.

Overall, if price is an important factor for you, then you will be better off sticking to regular women’s shops when looking for sissy lingerie.

Why Sissies Prefer To Buy Lingerie Online

People in general love to purchase stuff online because it’s so convenient and the shipping times can be pretty damn fast now-a-days. Sissies shop online for the same reasons but also because… they can remain incognito and avoid the embarrassment and awkwardness that comes with dealing directly with retail sales people, who are typically women.

Sissy Girl Etiquette Guide Printable

But there are some seriously sound reasons for you to NOT shop online sweetie. Your sissification program is a process. Part of that process is to slowly but steadily began to embrace the fact that you are a girly-girl at heart. One sure way to do that is put youself in an environment where you can let your sissiness shine.

But the title of this article is “Sissy Lingerie on the Cheap” and women’s retail stores are anything but cheap. Yes, the majority of them are not inexpensive, that’s for sure, but a few of them are. So I’m giving you two very good reasons for buying your sissy lingerie locally:

• A way to shop that will expose your sissiness in a subtle way
• Bargain prices

Types of establishments that comply with both of the above elements are none other than your local thrift store.

Why Buy Sissy Lingerie at a Thrift Store?

The prices are better than right AND you’ll be hanging out in the lingerie/intimates aisle. The cool thing is that you won’t be dealing directly with a salesclerk. Sure, people will still see you, but that’s the point.

You need to start conditioning yourself to the fact that you absolutely belong in the women’s section of the store. Do it once and the next trip will be easier. You will soon come to the point where you don’t give a rat’s ass what anyone thinks.

Besides, you could be buying that sexy black bra for your girlfriend or wife; nobody knows or really cares, if you want to know the truth. You will have to deal with a real, live person at checkout but rest assured, they’ve seen it all… and then some.

Depending on the thrift store, you can find some really nice bras, babydolls, camisoles, teddys and negligees. You won’t find many (if any) panties however, due to health and sanitary reasons.

Where to Buy Inexpensive Panties

Depending on what state (in the US) you live in, there’s a fairly good chance that there is a 24 hour Walmart close to you. You will find plenty of pretty panties to choose from at Walmart. The idea is to go early in the morning when the store is more or less deserted, but not so early enough that the the speedy-self-serve checkout stand isn’t open yet. That way you won’t have to deal with a check-out person.

But even if you have to go through the regular check-out line, please believe me when I say this: Walmart employees do not care! Regardless—just like I mentioned earlier—it’s good practice for you to purchase your sissy things in front of a real, live people.

If you’re a bit nervous or embarrassed, that’s only a sign that you’re serious about owning up to your sissiness; and that can be quite empowering.

You can also find reasonably priced panties online at B2BODY (formerly Barbra Lingerie). Their thong panties are satin-like-sexy and the front panel is fairly wide so full coverage is not an issue. These panties also sport an open-ended crotch liner/gusset so as to make tucking super-easy.

There are many, many other places online where you can shop for lingerie on the cheap. eBay and Amazon are, obviously, two of the usual suspects.

What Type of Panties are Perfect for Sissies?

As a sissy, it is so very tempting to fall in love with the most slinky, skimpy and sexiest of panties. I know it is for me. Keep in mind darling that your sissy panties (unlike a genetic girl) will need to possess two attributes; sexiness and functionality. What do I mean by functionality?

In order to achieve that flat, feminine front, you will be tucking your sissy clitty back between your legs, with your balls pushed up on either side. This will require a large enough panty panel in front to securely hold everthing in place without allowing your nuts to squish out to the sides. Because of this potential problem, it’s wise to buy one pair of panties at a time until you find ones that work best for you.

So sweetie, if you’re willing to delicately step out of your comfort zone—just a little bit—it’s very possible to find some absolutely beautiful lingerie that won’t bust your sissy budget.

If you do happen to harken to my suggestion and waltz into your favorite thrift store, bravely heading straight to the lingerie section, please remember this: act like you belong there… because you do!

Corsets Are Lingerie Too!

When adding to your intimates collection, don’t forget to include corsets and waist cinchers on your lingerie list. Besides being a super-sexy form of lingerie, they will also help you to acieve that much-sought-after-wasp-waist. The Sissy Guide to Corset and Waist Training will answer many of your questions about these alluring undergarments.