Sheery in DKNY bodysuit and pantyhose

As usual, I like to write here when I’m in the mood. That is, fully crossdressed and feeling like miss me. Over the years though, (and it has been quite a lot of years writing here) I’ve gone from slipping on some pantyhose and maybe lingerie to full-on shaving, makeup, wig, perfume and paying attention to those little details to transform myself into a more feminine persona. Oh yeah, and a spray of Chanel No. 5 really does help with that.

I know I’ve dived into this before but the more I’m transformed into a woman and see more of a woman in the mirror, I can’t help but to convince myself I just might actually pass for one. It’s definitely a feeling of empowerment and, not to mention, quite a high that I get off of. I don’t know, I would say kind of like an adrenaline rush I’m having even though I’m not actually out in public strutting my stuff if you know what I mean.

Of course all of this makes me incredibly horny yet in a way that truly distinct from my usual male self. It is just something about smelling that perfume or noticing that flavor from my lipstick or even noticing that warm silky feel of the pantyhose draping my legs. Or is it the wine? It is as if it is an experience of being an actual woman who feels turned on which, in itself, I can say is truly a pleasure I crave.

Then it’s moments like these that I occasionally break out the Fleshlight (with that little thing so I can mount it on my refrigerador) and desire nothing more than to be rammed in my backdoor, ironically, while standing in my heels and fucking my little toy. I have natural female-like boobs, too, (weird genetics) so I also like to pull down my bra and push my breasts together wishing a cock would squeeze right between and come right in the middle of them. Oh, and then I like to give a soft rub on my nipples which gives me mini-orgasms.

You can say my masturbation has evolved over the years.

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Rumpy Butt Plug

I’m not afraid to admit that I like to get it on… alone. Hey, it’s actually healthy for the sex life to keep the juices flowing and release all that tension when needed. In fact, a lot of you out there seem to agree since my most popular post is some ideas for your kinky mastubation. So I’m not alone here in liking to get down and dirty without the typical wake and wank. A little creative masturbation can actually be quite a thrill.

Hence, I came upon (literally) a new little friend of mine, the Rumpy Butt Plug. You can see, it’s not your average drain stopper, actually looking more like a fat dildo. And so there is nothing like putting a new toy to test, especially one that looks like it can tear quite a hole in you and then some.

The Rumpy has quite the dimensions for a plug: 6 inches (15 cm) of insertable pleasure, 2.25 inches (5.7 cm) in diameter of the large bulb and roughly 1.75 inches (4.5 cm) in diameter of the large penis-like head. It’s nice and smooth with no rough spots or edges and made of a soft PVC that has some flex to it. A pretty sight it is!

Now for the trial. To get into the mood, I slip into some hold up stockings and a bra and a little perfume to top it off. Then I lube up the Rumpy and my asshole very well and attempt to get that bad boy inside. The head of the plug slipped in after a few pushes and gave me quite the jolt when it did. It definitely is unlike anything I ever put up my ass before and I’m thinking with wide eyes “This thing is no joke!”

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Sheery the Crossdresser

Dear Mrs. Rainwater,

I’ve always been very curious when recalling my path leading up to becoming a crossdresser (and likely a future transvestite roaming the streets). It all seems to trace back to you as my teacher in my very first year of school when I was just five years old at the time. Actually those memories of you are still quite vivid in my mind.

I remember you would always wear those blue tights with sandals that would let those glorious hosed feet show. On those days, I would obsess over those gorgeous blue legs adding to the innocent boyhood crush I had on you. Of course, how could I forget, there was that one day where you lined up me and all of the other students and gave each one of us a big kiss on the cheek in appreciation of having us as students.

I’m sure you’re aware that doing that today would send you right to jail. However, I took it for what you intended it to be: reaffirming that crush I had on you was the real thing, even though I was five.

Since then, I wanted to be just like you, starting with the tights.

I became so obsessed with tights, that is, starting with the pairs I stole from my sister, who was catching on to my love for them. Then one day, I scrounged up my allowance money to buy my own pair of L’Eggs Sheer Energy pantyhose in an off-black color. My very own shiny, sensual, nylon-covered legs gave me such a thrill, almost as much as that smooch you laid on me years before.

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Sheery in a camisole and pantyhose

Usually when I post here, I’m very much “in the mood.” That is, not just dressing the part but living up to it so to speak. It is usually morning time, I’ve had my cup of coffee and am in my cute satin robe that just barely covers my ass. Of course, I have on silky pantyhose, high heels and, to feel extra sassy, throw on some lipstick (now a regular thing).

While it is a major turn-on to see my silken self shine, I’ve embraced my feminine role enough now to go beyond the usual crossdresser frolicking and into a realm which hasn’t been penetrated to the full extent yet (excuse the pun).

Namely, I can’t stop thinking about that feminized penis that wants to violate me and make me believe I’m a true woman.

Maybe five or six years ago, the thought sex with another crossdresser would have never even crossed my mind. I was a happy-go-lucky crossdresser content with throwing on a pair of nice pantyhose with a cheap bra and panties, wank it then call it a day. You know, the typical practice during the some twenty years prior.  Then one day something dawned on me, or you can say the little girl in me was starting to bloom.

It feels quite sexy to look like a woman in her skimpies and admire it in a mirror but what would it be like to feel and take pleasure like one? Rolling around in nylon and lace isn’t quite the same so there I was one day, laying in bed (lingerie, hose and all) getting into various positions and pretending I was on the receiving end of a good pelvic clapping. The fact that it made me question my, at that time, heterosexual self (I’m not gay, am I?) actually made it even more alluring.

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Naked in Pantyhose

Odds are that if you are reading this right now then you quite have the pantyhose fetish. You probably even have on a pair right this moment slowly massaging your growing hard-on as you are reading on these words like an erotic fantasy. Don’t be shy or afraid to admit it (I’m not as I am writing this). Let your lust for silky nylon take over and dominate you.

Now I ask, is that all you have on, just a favorite pair of pantyhose from a cache full of others of varying types?

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The Pantyhose Mermaid and Silicone Dildo accessory

So there you are all dolled up in that skimpy dress, favorite pantyhose and super tall heels and you can’t resist what is looking back at you in the mirror. It gets just a tad boring though with the hand to penis thing that you’ve done for, oh, the 10,000th time in your life. You’re a crossdresser for God’s sake so you are use to an alternative sexual lifestyle.

Why not explore this further? I’ll even let you have a look at my little bag of tricks. Here’s one of them if you haven’t seen it yet but I’m sure you’ll have some fun with these others.

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Skinkiss Pantyhose Model
What I aspire to be. Sigh…

I was lying awake in bed with my little camisole top, panties, some super silky bronze Elly 40’s and daydreaming.

What would it be like to model pantyhose and be immortalized on that package sold all over the world? I have a thin, athletic figure and nice legs. It’s time for a new profession.

There I am in a studio with odds and ends furniture, bright lamps all around, a professional photographer, the assistant, a makeup artist and me, the model, in the middle of everything.

Having nothing on but a barely noticable bra, I’m given a pair of shiny 30d pantyhose to put on, the real star of the show to take place on my body.

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Fuscia Baby Doll and Pretty Polly Pantyhose
Fuscia Baby Doll and Pretty Polly Pantyhose

Pantyhose enthusiasts (or fetishists, perverts, weirdos if you’re so inclined) generally have a routine whenever there is a day off with some time to kill or the wife and kids have left you alone for a few days. Ah, yes, now free to see the “mistress” that is our beloved woman´s garment. Yes, that includes myself if you couldn’t tell already. So here’s a little insight to a hot date with a longtime love affair…

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The lovely transvestite, Lauren Close
Credit: Lauren Close (Flickr)

As is customary, we as crossdressers or transvestites find those moments where we can’t resist entering our inner woman and bask in the satisfaction that immediately results. For me, that means stripping naked, shaving (not just the face honey), a shower and choosing some silky little things that I’m in the mood for.

Let’s see, some Wolford tights and heels making my legs unbelievably sexy, check. I’ll go with the nude today.

Hmmm, a black teddy, see-through in the bust area. Check.

Long black gloves, brown wig and lipstick. Check.

A little perfume to top things off (you really have to try this). Done.

It’s incredible the intensity it brings admiring that “model” in the mirror, turning around for the butt view and making yourself more “wet” by the moment. Now that I’ve successfully seduced my better half, time to take it further.

Auto-erotic time since no one else around? Check.

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