Sheery in bed touching herself

Sure I like to write, in a way to let out all my weird, perverted or just plain everyday thoughts into something I will more than likely look back on. So yeah, a public diary of sorts that I leave open to all who care… or not. I also do happen to keep a little notebook that I write in strictly on the topic of my crossdressing. I don’t know whether it’s the pen and paper or it’s as if I like to keep pretty damning evidence around but I kind of enjoy it.

So I happened to read through it the other day and an entry from a while back caught my attention (and jogged a memory). I won’t lie, I do get off on my crossdressing. I’ve even touched on masturbation methods here or there but this was actually a particular session that I remembered pretty well… I wrote in my journal while in the act of some self-intimacy which happened to be something I always had wanted to do when I write. Call it inspiration or whatever, maybe you can relate…

5/5 – As I write this, I am dressed in my new teddy and Neon 40 tights, red wig and some lipstick grinding away with my Fleshlight. I feel like a princess with a dick and feel no shame for it. No way!

I slip on a condom (to make things less messy so to speak) and grind harder, faster. Ooooh! I obviously love this feeling plus I love how I look in my beloved lingerie and pantyhose (+ wig and lipstick). I turn myself on with ease!

Now I’m shaking, ready to come but I delay it. This is quite possibly the best feeling… hot, en-femme and horny as shit about to come. That stretch on my pantyhose, taste on my lipstick and strain on my legs from my tall heels all magnify that orgasm yet to arrive… then it DOES leaving me shaking and trembling. OMG!

Needless to say, I remember not leaving a mess afterward!

Oh, I guess I could part now on this gem of an entry…

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Sheery in a DKNY bustier and Wolford tights

It’s not news that I have my own erotic fantasies whenever I’m dressed and (almost always) in the mood. Yes, there is that vision of hot crossdresser sex with that beautiful crossdressed lover having her way with me or even tying me up helpless as I am wrestling around in my pantyhose. Yet there is always that one little fantasy that I’ve had for as long as I can remember… getting hot and horny in front of the camera (and maybe with that beautiful crossdresser).

I’ve actually seriously considered this and have looked into creating a CAM website or a live feed of me all dolled up and ready to go… well wherever, whatever. My motivation is pretty much directly proportional to the level of how turned-on I am which, unfortunately, is not 100% of the time. I still pick at that itch from time to time browsing for that perfect web camera, or something I would look oh-so gorgeous in while on camera. Hell, I even thought of adding it as a part of this website. Maybe a little blinking red button to enter my private room for a little show if you know what I mean ūüėČ

However, more recently I’ve been hearing about OnlyFans where pretty much anyone gets in on the sexy camera action and, not to mention, have a little side gig or even a primary income source while doing it. It seemed really intriguing to me, especially not having to deal with website development costs and, in return, leaving around 20% of earnings for the OnlyFans take. And if it does not work out or is not suited for me, no real time or effort (or money) is wasted. Sounds like a deal a bit hard to pass up.

Now there may be some work in drawing fans to watch me, which I’m well aware of, but that might actually work in my favor. I would probably need some camera time under my (garter) belt to make me less nervous as I do my thing in front of the camera for the one or two peepers getting off on it. But, honestly, I can’t really think of anything more exciting than getting into femme mode, slipping into some sexy lingerie and pantyhose and finishing it off with hot miniskirt, heels and makeup. Then I would get to do my little striptease and… hmmm let’s see.

So what would I do exactly on camera and all hot and excited? I’m thinking one or more of these…

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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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The Fleshlight
Image: Fleshlight

I have to admit, I am quite the sucker for sex toys. There are just certain times when I am all alone and I need to get my jollies off right on the spot. Nothing unusual, perhaps most of us do the same.

In my case, being the crossdresser of course, I take it the extra step which usually involves slipping into a fine suntan shade of pantyhose, a lacy teddy, stilettos, top off with some makeup and then open the drawer to see which one of the fine tools I’ll be using today. Sometimes I feel like a Bottom and I’ll go for the bSwish vibrator set on high which gets me moaning.

Yet other times I want to be the Top, you know, chickie with a dickie sort of way.

So I pull out the Fleshlight, giving the hand a rest this time, except for holding up the bottle to drop a few squirts of lube inside. Time to party.

I’ve had this thing for a few months now and, honestly, it’s quite a marvel for the male who’s a wannabe female who’s sort of being a male at the moment. So figuring there’s been enough test runs on this piece of pseudo genitalia, I can finally give a sneak peak at how masturbation has been mastered a little more.

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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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B Swish Bgood Vibrator

Sure, as crossdressers, transvestites or weekend femme-seeking warriors, we like to dress the part and maybe prance around doing that walk that makes our hips shake. ¬†I’m willing to bet, however, that most of us haven’t had the pleasure of partaking in another feminine pleasure.

That is, the ever popular vibrator.

Yes, I know it may seem a somewhat odd choice given our anatomy but truth is it can actually be an incredibly pleasurable and addictive experience. I can even tell this to you first hand.

Some time ago I purchased the Bswish Bgood vibrator for no particular reason but curiosity. OK, a lie. I was intent on experimenting with anal play and this just seemed like the perfect sex toy which I ordered, brand new and ready to go. It’s 7 inches long (18 cm), 1 inch wide (2.5 cm) and, after finding a couple of AA batteries to insert, has five different vibration settings to choose from.

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SOH Charmeuse teddy (with Wolfords)

As I sit here painting my toenails today, like a good little girl, and anxiously await my outfit for my night “out,” I finally receive that long awaited ring at the buzzer. Yes, it’s a package! I’m a bit nervous since that means I’ll finally out myself as girly me for a few moments in the next day or two. I’m eager to try on my first fem outfit however.

Hold on a second. I think this package is smaller than expected and begin to wonder if the club shorts and dressy top are skimpier than I had thought they would be. Then I rip the package open to find a gorgeous charmeuse teddy (Shirley of Hollywood). Oh, right, I forgot that I ordered lingerie about a month ago after coming home after a night of drinking with the chums.

Well, I can’t throw this on and take this out on a stroll around the block. At least not yet ūüėČ

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Wearing a Teddy with Danskin TIghts

I woke up refreshed but feeling unusually horny this morning. Enough so to make slide into some shiny Danskin tights, throw on a cute black teddy then into my usual bathrobe. I can’t remember what I dreamed about last night but it really has me in a feel sexy mood today.

After my morning coffee, I skip reading the news and head directly back to my bed and pull out the vibrator from a drawer nearby. It’s nice and slim, smooth and about six inches long which is perfect for some womanish masturbation.

I unsnap the crotch on my teddy, turn my little toy on and, remembering an idea from somewhere online, begin to penetrate my ass but through the pantyhose. The stretch on the tights limited penetration to just a few inches but it was all that was needed. Oh, did it feel nice and incredibly kinky at the same time!

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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¬īs 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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