Monday, October 24, 2016

Simon/Joy: Frisky [nsfw...]

God help me but sometimes I just love it here. I mean, I knew there had to be some consolation for the tampons and the grooming rituals and the uncomfortable heels and the leers from old men when I come flouncing down the sidewalk in my shorts. I've found it, pretty much exactly where I expected to.

I mean, what life isn't complete without it? I loved it as a man and though it took me a while to get around to it as a woman I find the thrill tenfold more satisfying. It just goes to show that sometimes you need to work hard to get what you want.

I'm obviously talking about my big fat commission checks. My God if I knew I could make this much this quickly I would have moved here years ago.

Haha but seriously, between all that, I've found time for another real delight. A serious pleasure. And it's uh, obviously not something I'm getting paid for.

So let's talk about me, and my new best friend Mariah. That's what I named the device I got from Treena a few weeks ago. Why shouldn't she have a woman's name? I've always loved her music...

For a little while I just let it sit in the box, ignored. I wanted to pretend I didn't need it. I know the basics of pleasing a woman and it should be doubly easy if that woman is me. But my efforts so far have just taken too much time to feel worthwhile. I just didn't happen to want to put in the effort yet, since there's been lots on my mind. But if I thought I would NEVER try it out, I must have been kidding myself. Curiosity is a powerful thing.

I went to see Treena's burlesque show at the beginning of the month. I thought I knew what to expect, since I've been to plenty of titty bars and seen lots of stuff - hell I give myself a bit of a show every night and morning I the mirror... But I wasn't prepared for this. Women who looked like Treena - or not like her but definitely not like any woman you see at the Club - performing skits and dance routines, and one even doing a topless karaoke to Wilson Phillips "Hold On" while fit athletic men backed them up. I wondered if they were all gay, or just standing by getting hard. But as the night wore on I found myself tittilated... Not by the sights exactly, but the atmosphere. Hot guys, fearless women... It was hot, steamy stuff both men and women could enjoy, if one is open minded enough.

I stuck around to congratulate Treens on a good performance and tell her how impressed I was with her acting and singing, and she offered to introduce me to the guys... But for one of the first times I was just too bashful. I don't get it! I was always great with women, why shouldn't I be even better with men? They're the ones who should be tripping over themselves to talk to me. But I just felt this embarrassed flush in my face. And all I could think of was Mariah back home in my drawer...

When I got home I said a quick goodnight to Treens and headed to my room. I threw my clothes on the floor and laid my naked body down on the bed, legs spread, with Mariah in my right hand. With my left hand I caressed up and down my soft, sensitive skin, feeling every curve that I have gotten to know these past 4 months until I arrived at my soft, petite breast with its pointy raised nipple. I licked my finger and stroked around the outside of it as I flicked Mariah on and heard her low soft him, like an electric razor.

With one final pause I slipped her in between my legs. She isn't shaped like a penis so I figured it's not really meant to be "inserted," which I wasn't really ready to do either way, but holding her against the outside where she could work my clitoris produced a sensational feeling on its own!

The thing caused my body to take off like a rocket. I could hear myself start to moan and my body twist almost uncontrollably. I needed to keep going. As my hips gyrated wildly in response to the pleasure I increased the intensity and pressed harder. My heart raced as my pleasure built and built until finally I felt myself just... explode! Powerful muscles inside of my flickered telling me I had reached bliss. It did not take long at all to complete, probably because my male brain was so overwhelmed by new sensations. And then, because I could, I kept going, because one orgasm simply was not enough.

Once I decided I was done, after an hour so of intense, almost unbearable delight, I just laid in the glow of it. I felt like a whole new person. More complete than I have in the entire time I have been here. More than when I was a man!

Things might never be the same for me. But feeling embarrassed about feeling pleasure is so stupid I can't even bear it. since then, I'm walking taller, smiling more, just generally being more pleasant to everyone around me, lol... and meanwhile every night I just can't wait to rush home and try something new. I've done it with my legs in the air, on my hands and knees, sitting on it... I'm honestly becoming the filthy ho I was clearly meant to be.

And as to what someone said about it being a "gateway"....... we'll see, honey. I honestly think I'm getting everything I need right now.

-Simon

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Monday, October 17, 2016

Tyler/Judith: Awkward conversations that needed to happen

I was getting dinner ready yesterday when Kitty came home. She had mentioned she was going to pick up some groceries and "essentials" on the way which is cool with me... I mean, I try to do all the groceries in one shot when I have a day off, but sometimes stuff escapes my notice.

She trundles into the kitchen with some BulkMart bags with huge quantities of paper towels, toilet paper, et cetera, and I think "Okay, maybe we don't need to stock up for the zombie apocalypse but this is good." She gets to work at putting it all away - where she deems it appropriate to go (I stopped putting up a fight but her system doesn't seem intuitive to me, the person who spends the most time in the kitchen) and then at last, when she's almost done, she hands me the final item and just says "By the way, I picked these up for you."

I turn around and see, sitting on the table, about ten or twelve packs of tampons, panty-liners, and overnight pads.

I was pretty mortified. Sure, I've made peace with the fact that this is part of my day-to-day (or month-to-month) life, once again. But I guess I'm still pretty modest, I like to keep my feminine paper stocked under the bathroom sink, discreetly away from prying eyes. I didn't even know where to keep a box this size.

"Are you shitting me?" I gasped.

"Shh, don't let the kid hear you yelling like a madwoman or she'll think it's okay to copy," Kitty hissed back.

"You think I need a crate of these?"

"It was a great deal, Jude! They had a multi-buy discount, and double the bonus points... It was win-win."

I bristled the way I always do when Kitty calls me "Judith," "Judy" or "Jude" - which is almost exclusively these days.

"This isn't even my brand," I muttered bitterly.

She went on, "I noticed you were out of them. I just didn't want there to be another incident where you forgot it was coming."

"I have the tracker app on my phone."

"Tell that to the khaki capris you ruined..."

I clenched my teeth. You make one mistake and suddenly you get a reputation. Yes, I stained some pants of Judith's - a very bland, boring pair of capris that Judith probably wouldn't have cared about, but after they had to get tossed it was "Oh, these were so lovely, they looked good on you!" Bleh.

So at that most convenient moment, Dylan walked in and noticed the package on the table.

"Woah, that's a lot of tampons," he snickered. "Are you bleeding right now, Tyler? Is it a total red river down there?"

"Don't talk to her like that!" Kitty snapped. I said nothing, but I was also pretty perturbed about that remark and glad to have Kitty reprimand the kid. She added "Besides, they may be for you, too."

All the color drained out of Dylan's face. "But I'm... Olivia's only ten..."

"Some girls get it that young," Kitty said, "And we don't know how long you're going to be like this..."

Almost immediately I saw a stream of tears from his eyes. "But... that's not fair..."

He darted off to his room and I let out a sigh. "Nice going, was that necessary?"

"She's got to learn," Kitty asserted. "This is because you insist on treating her like she's still a boy. We don't even know what she knows about this stuff."

"Enough, obviously..."

"Well, we might as well get it over with," she said, heading for the stairs.

"Hey," I said, hustling after, "Mind if I take the lead on this?"

She pursed her lips. "That's fine, but I'll jump in if you leave anything out."

So we went to check in on our daughter. I remember when I was a kid, how this kind of information gets around to the boys only in fragments, so we asked what he knew, or thought he knew, corrected some of his misconceptions and filled in the gaps. It was... honestly, a pretty refreshing, satisfying talk.

My gist was that it wasn't a big deal, and that it doesn't change who you are or what you can do with your life. And deep down he is going to continue to be the person he feels he is.

"Uh huh..." he said, eyes carefully avoiding mine. "But then I'll get boobs, right?" I couldn't tell if he asked out of fear or anticipation or just matter-of-fact curiosity.

"Well, the two aren't really related, so it could be one, then the other, and there's not really a, um, set timeline. If everything goes according to plan, you probably won't still be here when this stuff happens to Olivia's body. But we need to be prepared in case it happens early."

"Or if we're here longer than expected," Kitty chimed in. I shot her a look for that - it's not a possibility I'm giving much credence to.

Eventually, Dylan seemed satisfied by the information, or was just tired of talking about it, and asked if he could do something else until dinner was ready. In the hallway, Kitty took me aside and said "Hey, I think we did a good job in there."

I smiled a bit despite myself. I guessed that I was so used to being second-guessed by Kitty that getting a nod of approval - even if she felt she had to take a share in it - felt strangely good.

She went in for a hug and I let her, holding onto Adrian's husky frame a while. We haven't had a ton of physical contact since we became this way... there's this unspoken understanding that we have to figure some stuff out, and there's simply been no time or energy for any of it. But it was nice to feel like I had a partner in this, not an opponent.

And now that I've crunched the numbers, I can admit that buying tampons in bulk was a savvy move. It's the idea of going through that entire supply that has me squeamish.

-"Judith"

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Tuesday, October 11, 2016

Tyler/Judith: Everyone needs a hobby

The Trailblazer Girls thing was a surprise hit with Dylan, I have to say. The uniform - a vest and khaki shorts - doesn't scream "Girly girl." The activities are not overly rugged - nature hikes, leaf-collecting, and that sort of thing. It feels like a good balance because I don't get the sense that Dylan was exactly the most outdoorsy kid, but it's clear there's still an impulse there to explore and get a little dirty. Which I'm in favor of.

Surprisingly, Kitty has taken to it, too. Trailblazers involves a little bit of parental participation, carpooling and organizing, and I'm surprised she didn't press me to handle it since she's working so much and I'm... not. She stands out as the lone "Trailblazer Dad" and gets kudos from the other Gals just for doing the exact same stuff as they do. Weird double standard there. But it seems to be scratching some of her itches, too, a need to be around "regular" women, get involved and plan things. I mean, almost every day one of us mentions how much it sucks that I ended up in the Party Planning business, and she's the one reporting for a 9-5 job Monday to Friday. I've never done one of those either but she seems to think it would help me cope. Sure, except for the part where none of it makes sense to me. (She'll never admit it, but I think HR is Kitty's secret talent - getting policies and procedures just right and getting up in peoples' business.)

I haven't spoken much about the job because, well... there just isn't much to tell. It's mostly taking calls and booking venues for fundraisers, with the other women doing all the heavy lifting. The office is all women, mostly the same age range as Judith - thirties and forties, all with kids, and that's pretty much all they talk about, and there is a lot of time to talk because business is slow.

I thought about getting a second job and even mentioned to Kitty that I could start driving with Thrio again. She was adamantly against that - "You're a woman now, you don't know what kind of sickos are out there." I like to think I could handle myself pretty well but it's likely not worth the trouble. And while back in the spring I would have taken the job just to spite her, nowadays I'm a bit more inclined to co-operate... if only for Dylan's sake. It's different when you have someone depending on you.

The ladies at work have a book club, which I kind of dropped out of on Judith's behalf when I became her. But maybe it's time to reconsider. It would get me out of the house every so often for an evening, keep my brain from getting stale from routine. I don't love hanging out with these women so much, but I'm not exactly in a position to be picky about my social circle right now.

-"Judith"

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Sunday, October 09, 2016

Innbox: Mrs. Brooks

Hey all! Tori here again... hope you haven't forgotten about me... Looks like none of pur regulars have had much to say lately (unsurprising since the life of an Inn person can get very... complicated!) I thought Noe would be a good time to share a letter from a fellow visitor that landed in my inbox a while back. Hope I can find the time to update you on my life soon too!

Lots of love,
Tori



Dear Trading Post Inn,


It has been 20 years since I visited the Inn and all these years later, I can hardly believe my luck. Of course at the time I didn't necessarily see it that way, but even at the time I viewed it as a boon of sorts. Like many who have been through this ringer, I lost lots but somehow managed to gain much more. Going to the Inn basically saved my life.


At the time, in the year 1995, I was in my early 40's, still a strapping man if I do say so, but with no prospects. I had spent several years in prison for something that I wished every day I could take back, but would have to live with the knowledge for the rest of my life. In a moment of desperation I held up a gas station... and in my haste to get away, I had forgotten to gas up my car. Funny when you read about it in a "dumb crooks" article, not so much when you live through it.


As much as I tried not to let my time behind bars change me, it was beyond my control. When I got out, I was divorced, jobless, scrounging, unsure what I was going to do from one moment to the next. It was hard to find work, let alone purpose in life. I considered re-offending just to get thrown back behind bars where I was more comfortable. Then my wanderings brought me to Maine, to the Trading Post Inn. And Mrs. Brooks came into my life - or should I say, I came into hers.


It was a shock to wake up one morning and find that I had been transformed into this kindly-looking 55-year-old Kindergarten teacher, but as I learned about my "new life" I felt invigorated. At the time, we didn't know - certainly nobody told me and there was no internet to provide information - that there was a way back. The original Kathleen Brooks had written with resignation that she intended to go back to teaching and hoped that the "new her" would do right by her. I did.


It was not an easy adjustment - I had no formal training as a teacher, no experience with kids. And I can guarantee that the PTA would have had something to say about it if they knew this sweet lady was secretly a male ex-con. But I grew into the role and did my best.


Kathleen's husband was a fine man, gentlemanly... given they had been together for over 30 years when I stepped into the role, I was surprised when he didn't notice me acting suspiciously. Although being a wife, and mother of three grown children, was not the life I envisioned for myself, it also helped provide that purpose I had desperately needed. Mr. Brooks became a warm presence in my life and the love I felt for him by the time he passed in 2007 was very real.


I retired not long afterward. I was determined not to become one of those old widows who can't take care of themselves and since then I have been travelling as much as I can. I've been to 13 countries, tried my hand at learning French and Mandarin, and met amazing people. I have managed to avoid becoming the cliché Bridge-playing old lady, although I do a bit of knitting for the grandkids too!


All this just to say... as I know my time is growing short... the Inn took my old life, my body, and many years from me... but that can never compare to the opportunities and experiences it replaced them all with. And I'm far from done.

My hope is that the rest of you find the good in your situation. I know it's there.

Regards,
Kathleen Brooks II

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Saturday, October 01, 2016

Simon/Joy: Obviously Treena reads the blog.

This morning when I woke up I found a nondescript white box sitting on the floor outside my door. Inside was a strange-shaped item called a "Leaf." It has a little button on it that creates a pulsing, vibrating sensation, and has another setting that causes it to squirm like a tongue.

With a note: "This will help you stay out of trouble, I hope." Signed, "The Inanimate Object Fairy."

I felt like she was making fun of me at first. But I looked it up... it was not cheap. It was a real gift. I guess she actually wants me to be happy, and thinks that if I incorporate this into my life I will be.

But for now I'm just looking at this thing and thinking, how ridiculous. Chicks need this kinda stuff to get off? Things used to be so simple...

I don't know, with a device this advanced, I get the feeling you're not supposed to just be "quick and dirty" with it. You need to give yourself time and really make an evening of it. (That's probably why my personal results have been... mixed so far.)

What do you think, guys? Should I take the leaf for a spin sometime? Light some candles, pour myself some wine and see what happens...?

Sure beats the awkwardness of trying to date a guy...

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