Saturday, September 3, 2016

The Absolutely, Positively True Story of Chrissy, part 2

So, I haven't posted on here in forever, but a few things have happened recently that have me wanting to blog some new stuff now.

First, my life is no longer a secret to the woman I love.  I have come out of the closet to her and have shared everything with her.  No more secrets, no more hiding who I am.  She's not entirely on board, and she still has a lot of questions, but she is crazy supportive.  I honestly could not imagine a more supportive and loving partner.  We're in this together for the long haul and I can not begin to express how liberating it has been to know that everything is on the table now.

Secondly, I recently read Leeanne's Sissy Musings.  Leeanne has been brave enough to post her story - from her earliest sissy desires to her latest adventures in cuckolding with her wife The Cheerleader.  If you have a chance check her out - it's a long read, but it is well worth the read.  At times it is crazy hot & sexy and other times raw & vulnerable.  She is incredibly courageous to tell her story - warts and all - and has inspired me to do the same.

(I'll be interspersing the more boring parts of the story with random pictures of hot chicks & naughty shit, just so you don't get too bored.  Oh, look - here's one now.)

Ooh look - tits!

And with that... Here we go.

In The Absolutely, Positively (mostly) True Story of Chrissy, part 1, I shared my first experience wearing women's clothing.  (Check that out if you haven't and then come back here & you'll be all up to speed.)

I titled that one "mostly" true because I didn't want someone to stumble upon it and use it against me in the future.  I figured I could always backtrack if I had to.  But it's all true and from here on in you get nothing but the truth.

Time for the good, the bad and the ugly.

First - the ugly.  I was sexualized at an early age (6? 7? 8? I don't know) by a girl and it continued off & on until about age 17 when I put a stop to it. She had the same thing happen to her at an early age (I found out later) and I don't blame her. It was clear in our sexual relationship that it was my job to pleasure her.  I spent hours with my tongue between her legs and learned how to please a woman, and how to serve. Has it fucked up my view of sex and my desires? Meh. Maybe? Probably? But who says I wasn't born to be a sissy in the first place?  (I'm just glad that I never continued the cycle of abuse to someone else.  I had a couple of experiences with boys my own age, but I think that's a fairly normal right of passage that almost all men go through.) Anyway, what was I saying about born to be a sissy?

I'm guessing she was also born to be a sissy.

At age 21 I was living with a roommate.  He's a little older and typically went to bed earlier.  I'd get bored and lonely late at night (I couldn't buy a date at that age...) so I started frequenting yahoo chat rooms and ICQ (Remember ICQ? Anyone? Anyone?)  ICQ and yahoo chat rooms can be summed up in 2 words: Sausage. Party.  I got so bored looking through a constant stream of dudes trying to find a woman anywhere in the room that one night I got an idea.  What if I pretended to be a woman?  I was horny and wanted some hot conversation - what difference did it make if I pretended to be the girl?  I'd seen enough porn to know what got me hot and what I thought other guys would like to hear.

I logged out of whatever name I was signed in under and signed back in as something like "hornycoedslut19" - I don't remember what it was for sure but if the guys were looking for a girl, there she was.

Like her, but less subtle.
My screen instantly exploded with private message requests.  It was like Peter North had just shot a load on my monitor, but if his sperm was made up entirely of messages that start with the word "hey". Whoa.  I'd never had that many message requests ever, let alone all at once.  Maybe I was on to something.  What was this feeling I was experiencing for the first time..? Hmm.

I ignored most of them, and narrowed it down to a few who could hold a conversation.  In short order I became the pornstar I'd always lusted after for a few select men. I talked dirty. VERY dirty.  I told them what I wanted them to do to me, and anything they wanted to do to me was fine in my book.  I had men stroking their cocks for me, begging to let them fuck me, shooting their loads for me.  And then it hit me.  That brand new feeling? It was a feeling of power.  And I liked it.  

Soon I was logging in more and more, being the online slut to desperate and horny men around the world.  I loved my new position of power and I was hooked.

I wonder now how many keyboards I ruined...

I continued like this for a few years until I met a girl.  We dated, we "fell in love." We got married.  We were having sex!  But...

Here's the bad: it wasn't great sex.  It wasn't even good.  It was mediocre.  She was a pretty girl with a huge rack but her interest in sex was missionary, lights off, while going over her grocery list. (I swear that actually happened once.) Her go to line before sex was "Alright, get a towel."  Wow. Sexy.

Imagine her going over her WalMart list during sex.
Kinda loses something, right?
I tried buying her sexy lingerie to spice up our love life.  I tried "sexy coupons", couples role playing games. I did everything I could to get her engaged in our love life.  Her lingerie would get worn once and then go in a big box.  Sex was nothing more to her than the thing we did to make a baby.  And when that wasn't working out and we turned to medical intervention, sex wasn't even an option anymore.

I don't blame her.  She had her own baggage and I was not the best husband.  We drifted apart.  And when we drifted apart, I drifted back to the chat rooms.  I'd sit in the basement at the computer, getting random strangers a world away off, waiting for her headlights to come down the driveway.  

And now... here's the good.  One day she went out to go shopping and I knew she'd be gone for hours.  I went into her closet and opened up the big box of one-time-worn-and-now-discarded lingerie.  I lamented that those outfits would never see the light of day again.  I laid them out on the bed, one by one, remembering the hope I had had for each of those outfits to spark something hot & beautiful & real.  I picked through the outfits, lamenting what could have been, and then I picked up this very outfit:

Beautiful tits not included.

That Dorothy looking outfit.  I held it in my hands for a second and like something out of a movie a surge went through me.  I was instantly transported back to that time as a 12 year old that I had tried on my sister's teddy.  I hadn't thought about that in 10 or 15 years but I instantly remembered the feelings and I was overcome by desire.  I had no choice.  I HAD to try on that Dorothy dress.  

I ran to the front door to make sure it was locked.  I locked the back door.  I checked the driveway for her car 3 times. I ran back to our bedroom and stripped off my boy clothes. I stood there naked and exposed holding the dress in front of me.  I checked the front door again and the driveway 2 more times, sheilding my naked body with that dress.  Finally, I dropped the dress to the floor of our bedroom and slipped it up my legs. The feeling of the cotton and the lace and the petticoat instantly went to my head.  I zipped it up in the back and it fit perfectly. I pulled on the cute lace panties I had bought with the outfit.

I was in a state of euphoria.  I hadn't felt this sexually alive in... well since ever.  And that's when it dawned on me - the dress fit perfectly.  The dress. Fit. Perfectly.  I surveyed all of the hot lingerie strewn across our bed - all of the cute otufits, the hot outfits, the downright fucking slutty outfits - all of them were my size.  All of those outfits I had hoped would spark something actually had, just not what I thought they would.

But I had to put them all away for now - the wife would be home soon!



  1. Welcome back! Are you gonna post more captions? I really did enjoy your captions a lot.

    1. Thanks for the kind words! I don't have the time these days to spend on cations like I used to. I'm kind of a perfectionist, so caps take me forever to get them to the point that I'm willing to share them. I did just schedule some captions to post over the next week or so that I created for my tumblr so keep an eye out for those.