Posted on December 30, 2024 by Sheery — No Comments

Sheery, dressed to go out

Every year about this time, coincidentally just before the new year, I get into a mode of deep thought and begin to wonder what the hell next year will bring. I’m way beyond the New Year’s resolutions at this point in my life. Aren’t they the same things every year written down and then forgotten about right around that hangover after the Super Bowl?

My assumption is that this is a pretty typical process for many people in life, a little reflection and maybe look for some kind of spark to change something. Yet for me (or maybe you), the crossdresser, it is a bit complicated. This side of my life has been an evolution even up to this point in my life. Keep in mind I’m not not a kid anymore you know. Part of that evolution is checking out what other non-church-approved things are going on that other side since they seem kind of interesting. Let’s not kid ourselves, they definitely are.

I’ve realized more or less, too, that I need to keep evolving in order to be content with who I am as a crossdresser. If you were to tell me ten years ago that I would be shaving all my body hair every couple of weeks and having sexy dress-up romps here or there with other crossdressers, I probably would have quit crossdressing completely right then and there. Oh my god, how could I do such things?!

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Posted on December 22, 2024 by Sheery — No Comments

It’s that time of year again. Jot out all your New Year’s resolutions down just before the new year begins, go out all night and then wish you were dead with that hangover in the morning. For the crossdresser, it’s no different except maybe a little fuss picking out a dress for the night out. For now we’ll get just started with the top ten resolutions for us crossdressers and I’ll fuss with that dress sooner or later.

10. Lose all that weight (… of being a crossdresser).

9. Wear that stocking rather than hanging it by the Christmas tree.

8. Take up a new hobby, like dressing like a man.

7. Maybe buy some some new male clothes to keep the act up.

6. Finally quit crossdressing. Oh wait, really? Nevermind then.

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Posted on November 30, 2024 by Sheery — 2 Comments

Sheery touching herself

OK, not every night I have a date with a lovely crossdresser. Nonetheless, there are many a time when I do my dainty dress up that I easily turn myself on. Alright, why lie? This happened all the time for me as the miss crossdresser. Honestly, even the simple act of putting on my wig and then a little makeup, then looking in a mirror sometimes sends me into such an erotic rush that it kind of has to be dealt with right that at that moment if you know what I mean.

Years back this would mean a quick wank, washing my hands and then mopping up the surrounding area and I’m on my way. Yeah, real amateur like the teenage panty-boy I was in the old days. Not surprisingly, looking back I really can’t say I had enjoyed any moment I’ve masturbated in those days. It really was just something I had to do and got out of the way, like brushing my teeth. I probably could say sometimes brushing my teeth was more fun.

Hence, it was always masturbation = brushing my teeth – fun.

Well, at some point I decided I should at least enjoy masturbation for what it was, more specifically a guilty pleasure. Aren’t guilty pleasures fun or at least enjoyable? Right, enough of my justifications, the truth is masturbation for me actually evolved out trying a little of this and that until at some point I realized one important thing: the more senses that are touched on (no pun intended), the more enjoyable it is and the less “wank” it becomes.

So what is in my new “wank” routine you ask? Good question. Here are the ingredients to start:

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Posted on October 29, 2024 by Sheery — No Comments

Let’s be honest, we as crossdressers are not just understudies of our anatomically superior female counterparts. We try our damndest  to outdo them anyway we can, just like the competition it really is. Is there really any debate then that there are actually things we can do better than women… or are we just weirdos?

Well, yeah, there probably is but here are a few things that maybe we do a little better just as a reminder…

10. Smoothing out our unsightly “bulges.”

9. Worship our pantyhose, like they always deserved to be.

8. Shave our legs with our Manscaped Lawn Mower.

7. Rock the facial hair when we’re feeling a bit daring.

6. Make that leg hair too!

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Posted on October 20, 2024 by Sheery — No Comments

Sheery in Guess teddy and pantyhose

A few days ago, I was doing a “spring cleaning” of my home… you know, getting rid of the shit that you didn’t want to get rid of before but finally had enough with sitting around taking up space. Honestly it is quite a liberating thing to do, maybe even up there with flashing a peek of my bra when out and about. Of course, you have to do the usual looking through all aforementioned shit before deciding to throw it out or not, but guess what I found, in a random box for that matter?…

This black (now grey or dusty brown) lace underwire bra, with the underwire poking through exposed, was probably bought maybe twenty years ago and was, at the time, my favorite bra for a while. There were even matching panty briefs at one time which appeared to be no longer accompanying its sister undergarment anymore. Regardless of this bra’s rather dilapidated state, I still had good memories of my many times donning it over my chest and pretending I had real breasts. Not unlike memories of other silky garments found from my earlier days of miss me.

Now, last year I gave away most of my no-longer-used heels, lingerie, pantyhose, girly wear, etc. as a purge of sorts in order to free up A LOT of space. Keep in mind, this wasn’t the “purge” of trying to get away from my identity as a crossdresser. I had just thought it was time to free myself from all that girly wear that was no longer being worn. I couldn’t say I regretted it either although I did accidentally toss some lovely Guess heels that I really loved. I fortunately didn’t cry for too long though.

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Posted on September 28, 2024 by Sheery — No Comments

Sheery's legs in pantyhose, not in public

If you’ve read here a while, it is not news that I still have not gone fully public with my crossdressing. I know, I know, I’ve been doing it for so long that everybody and their mom and sister should be able to tell there is a feminine side to me with just a millisecond glance at me as a “man.” I’ve actually gone out dressed in public once (at night) and, more recently, accidentally outed myself in public. Needless to say, I’m kind of getting “out there” at a pace where I’ll be fully out in public as miss me when I’m dead. Maybe I’m being optimistic here.

It is kind of funny how it went from a sexual thing, which it still is, to kind of a hobby… how far can I take it to looking like a woman then judging it by how people around me react (or not). Then again, I’m pretty sick of being “macho” man and maybe an effeminate approach might be in store. Either way, I’ve been questioning why not just dress and go? It’s not like I’ll be running around in the streets in my trademark lingerie and pantyhose.

It should also be said, I think I’m over donning those girly garments underneath my normal clothes knowing others don’t know my little secret going on there. Keep in mind that I have been dressed around other guy ladies like myself several times but in more controlled situations where there are only us crossers and others who don’t mind our company. I do want out in the wide open though and do want that side of me to be expressed someway, somehow.

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Posted on September 9, 2024 by Sheery — No Comments

Sheery in heels and in bed

Part 1: Getting to know Kristi
Part 2: The HOT date
Part 3: Kristi leaves a souvenir
Part 4: All good things come to an end

I have to admit, I felt quite overwhelmed in that moment as we were standing there making out like teenagers. I was basking in the proverbial afterglow of the most wonderful sex I’ve had in ages and, at the same time, I’m still in my Wolford Neon 40 tights with that nicely welcomed wet spot of Kristi’s love honey right over the crotch area. Being rammed in my pantyhose has been a longtime fantasy of mine and that feeling I had right then and there was exactly why.

Fortunately we weren’t done just yet…

Kristi gave me another passionate kiss, but this time with her hand caressing my hardening girly rod over my wet pantyhose making me let out a light “oooh” in pleasure. She suddenly quit stroking me, pulled away from our kiss and got down on her knees. Then using both hands she started slowly pulling down my pantyhose and gaff all at once (yet again) exposing my little girly rod, now pointing straight her. She smiled as she began to tease it lightly with the tip of her tongue.

Then into her mouth it went, all the way in and with a suction I had never felt before, not even from a biological woman. I could feel her beautiful  lips slowly sucking and slurping back and forth. I moaned louder as I reached a point where I was about to explode in her mouth. However, as I was just about to warn her of the impending flood of my own love juice, Kristi stopped her magnificent sucking and slurping and reached for a condom and the bottle of lube within arm reach on the table nearby. She politely did the honors slipping on the condom and swiping a generous bit of lube over it.

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Posted on July 28, 2024 by Sheery — No Comments

Sheery in pink Wolford Neon and OW Collection Dress

It is probably no surprise or really even a secret that I’ve always been drawn to the color fuscia. It’s bright, sexy, feminine and something I never dare to wear as me in male-mode. It’s also no secret that I’ve pushed for Wolford to bring back that gorgeous shade for their Neon 40 tights. That was nearly TEN YEARS AGO and guess what? They did bring it back for sale but I never caught on to it until way too late. Damn you Wolford!

However, there are those savvy sellers on eBay that know rare shades of Neon 40 can become collectors items. Then they stock up and sell these at collector item prices for crossdressers, errr, people like me. So of course I shelled out more than I should have for a pair (actually TWO pairs, you know, just in case the other pair rips). Anyway I tell the story about that purchase in a previous post.

Slipping into those brand new fuscia Wolford Neon 40 tights was like a dream come true and, WOW, they really are bright! The only thing, though, was that I didn’t have anything to go with bright fuscia tights. No lingerie, bodysuits, dresses, ok well a matching lipstick shade I do have but nothing else. So then I thought why not just celebrate my Wolford Neon win by getting a lovely dress and heels matching in the same color if at all possible.

That it was!

Over the course of the next month or so, I kept my eye out for anything that caught it. First I randomly stumbled on a pair of heels I immediately fell in love with… and even in that perfect shade of fuscia I was after. These 14cm (5.5 in) stilettos are from Le Silla and were even more stunning when I took them out of their box and slipped (and stumbled) into them. They are TOO TALL as well. Definitely the tallest pair in my arsenal of stilettos.

And, not to mention, they perfectly matched the shade of fuscia on the Neon 40 tights. Now we’re getting somewhere!

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Posted on June 25, 2024 by Sheery — No Comments

The author in her bodysuit, miniskirt, tights and heels

I try to be as positive, optimistic and/or fun (sexy too) as I can when writing here. After all, I am usually that way in my day-to-day life. Plus, who needs  a downer of a person in our little corner of the universe where we get to look pretty, smell nice and, not to mention, have cool, sexy womens’ shit to prance around in?

Of course, life is not always the sunshine glistening off of my pantyhose and I (plus maybe a good part of my other crossdressing cohorts) find myself in periods where I just feel… weird. I don’t mean in a strange mood or that I ate something I probably shouldn’t have or even that I’m just not feeling myself today. I mean that I feel like a genuine weirdo and have a sense that everybody in my own personal world thinks that I am too.

About 98.5% of the time, I don’t give a shit about it but, unfortunately, that other 1.5% of the time it kind of gets to me. Keep in mind that my close friends and family have no idea of my alter feminine-esque ego that has been slowly exposing itself bit by bit publicly. I get this impression that they know I am weird but they “just can’t point their finger on it.” Maybe it is better said that I feel like I am thought of as weird but not in a good or flattering way, or at least that is how I perceive it.

So call it my insecurities catching up to me while having a laugh, or maybe the ebb and flow of my emotional being hit its dark side at the moment. Either way, I cross paths with this every now and then, not with a high frequency, but it does happen. I can’t say that it always takes me to a darker place either. Usually I’ll have a wine and catch some action drama on Netflix or just order a pizza for delivery. Then I can get back to my unconscious weirdo mode and get on with my life again, or just go to bed.

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Posted on May 28, 2024 by Sheery — No Comments

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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