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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 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 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 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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Posted on April 28, 2024 by Sheery — 3 Comments

 

Sheery dressed for a date

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

OMG I’m thinking. The irony that cocks don’t really turn me on (or men for that matter). However, when I’m all dolled up and feeling oh-so-feminine, there is nothing I crave more, especially if it is from another beautiful pantyhose-wearing crossdresser like myself. I could go all Freudian and analyze my gender-bending tendencies, which I did happen to be thinking about for a split second, or I could just enjoy the moment right in front of me here and now. I chose the latter (duh).

Kristi heard my demand to get that lovely stiff girly cock of hers right inside me at that moment and stood up from the sofa. I stood up as well then planted my tongue down her throat (again) as I gently stroked her cock with my hand, making sure it remained nice and hard. Meanwhile, she grabbed a condom packet and a tiny bottle of lube from a rather ornate box nearby on a nearby table. I snatched the condom from her and ripped it open. I had always wanted to do that condom-in-mouth-and-blowjob-it-on thing so why not since the opportunity presented itself. It did involve a light pushing with my teeth but Kristi seemed to love letting out a soft “oooh” and, not to mention, her girly cock seemed just a little bit harder than before.

As she went around behind me, I bent over with my hands resting on the armrest of her sofa and stuck my ass out, maybe a bit too excited to get into position. Then I pulled up my dress and gently rubbed my own pantyhosed ass on her gorgeous pantyhosed cock, enjoying the hell out of this silky, sexy sensation. She caressed her hands on my ass then gave one cheek a light slap while letting out a giggle. I let out an “ooooh” in my now much-improved girly voice.

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Posted on March 24, 2024 by Sheery — No Comments

Sheery caught in Wolford bodysuit and tights

Well, for starters, I’ll let it be known that I’m still in the closet with my crossdressing. I’ll still have a quick public outing here or there but I’m still not quite known as THE local crossdresser just yet.

To be honest, I don’t see that changing any time in the future and I’ve been fine with that for a while now. My en femme crossdressing world colliding with my “real” world with my friends and family is not a reality I wish to happen. Believe me, I’ve mulled it over and even sought advice about it and came to the conclusion that maybe they are best apart. And that is OK.

So that said, last night I happened to be doing my little dress-up thing and, while I don’t always go full makeup, I almost always put lipstick on. I usually like some kind of bright pink or burgundy shade and I happened to swipe on a fuscia color that I love. Well, of course at some point I had to get back into to boy-mode, then run down to the “mini mart” store nearby my apartment building and get a few items for dinner.

Off went the femmy clothes, on went the pants and sweatshirt and off out the door I went.

As I am about to arrive at the store, I walked past a guy staring at me like he recognized me. Odd, I thought since I didn’t recognize him but as I opened the door to the store, it triggered a sudden sheer terror in me that I forgot to remove my lipstick. The clerk (who know me) saw me enter then quickly look down and leave as I did an awkward run-walk back home where I then removed that bright beautiful fuscia shade right off.

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Posted on February 25, 2024 by Sheery — No Comments

Sheery, undressing

There is no doubt that we as crossdressers, transvestites, t-girls… whatever you want to call us, retreat into our feminine skin, slip into something we love and momentarily basque ourselves into that girly little world of ours. The reasons may vary but it is pretty safe to say that it makes us feel good. I mean don’t we spend our lives chasing feelings and finding pleasure where we can? Then what happens when we find pleasure?

We repeat it of course.

But what really is that pleasure we seek in our femme skin? It most often is sexual (duh) yet it doesn’t just stop there really, am I right? Well, that may very well be where things can get a little complex. So back to that feeling we’re chasing, things can get arousing (duh) or maybe it calms us down after a long day of digging ditches in the prison yard. Maybe we just like that tactile tight silky feeling of that underwear that gives us that momentary chill up down down our spine.

Well, last week, I planned to try on a new piece of lingerie I had just purchased and did my usual routine of shaving all around, showering, then body lotion, then on to the makeup, etcetera. As I slipped into that new lavender teddy, I felt this incredible rush that I really only experienced a handful of times as a crossdresser. It wasn’t the usual “Oooh this is nice” while in my silkies but a more intense full-on high all over my body.

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Posted on January 28, 2024 by Sheery — No Comments

In bed in a Wolford dress and Neon 40 tights

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

A couple of hours into the four hour trip on the train to Madrid, my excitement settled down a bit and I fell asleep for maybe a half hour or so. When I woke up, a thought crossed my mind. Shouldn’t I be “dressed” for the occasion as in be fully dolled up by the time I rang the buzzer to Kristi’s apartment? I mean I did pack very well prepared to transform into miss me with the only male clothes being what I happened to be wearing there on the train.

Unfortunately, I didn’t just go anywhere en femme in public even though I could have gotten away with it in Madrid (maybe). So I devised a plan to change into my dress and tights at the Atocha train station when I arrived, wear my leisure sweat pants and coat over them and then when I arrived at Kristi’s, do a quick transform out of them and into my heels. Hopefully somewhere along the way I could make my face up really quick. A couple hours later I arrived in Madrid and set the plan into action…

So far, so good as I made my way out of the train station and onto the metro (e.g. subway), dress and tights safely hidden underneath my clothes and I even put on my medium length red haired wig tucked under a baseball cap. I got off the metro after three stops and checked Google Maps for her street, just a few blocks away. As I arrived to her building, luck would have it that there was kind of an alley just before it with no people walking around in it, something kind of rare for Madrid. I ran up into it, pulled out my makeup bag from my suitcase and did a rush makeup job on my face using the mirror in my finishing powder to help me apply it on. Ok, this looks passable, I thought.

Then I switched my running shoes for some tall heels just as an older lady walking her dog happened to stroll past with a curious stare. I just smiled as I repacked my suitcase and made my way out of that alley and on to Kristi’s building where I arrived a minute later. I rang her buzzer and that familiar sweet voice answered which almost made me faint. “OMG we’re finally going to meet!” I said to myself kind of giggling.

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