Did I Make The Right Choice?

An Obscura and an update on 'Just Dance'

When Jenny and I were married we experimented with cross dressing.  My naturally delicate frame made it easy to pull a curtain of femininity over my masculinity.  A little tucking to keep my panties smooth, a padded bra, some makeup, shaving smooth, styled hair, and beautiful cosmetics all let my girly side Maddison come out to play and hide away my manly Mark.  Sadly, while I enjoyed a lot about these experiments, our marriage fell apart.  It wasn’t for lack of love, but we just weren’t the right people for each other. 

So, when Jenny called up last week and asked me to join her as Maddison to try on some dresses and have a girls day in, I happily agreed.  I arrived shaved smooth below my eyebrows, ready for a day of Maddy and Jenny.  John, Jenny’s new husband, answering the door was a surprise.  Physically he was just about my opposite.  He stood four inches taller than me, was wide enough in the shoulders that I could hide in his shadow, and had arms thicker than my thighs.  His constant five O’clock shadow and rumbling voice welcoming me in set me on edge, but Jenny’s wide smile, gentle hug, and light kiss, put me back at ease.  John knew about my flirtations as Maddison and while Jenny said he never understood it, was happy to let her have ‘one of her girlfriends’. 

I quickly fell into my role of flirty fun girlfriend to Jenny’s happy demeanor.  We shared some wine as we played around with Jenny’s new flowered undresses and accessories.  I even let her cut my long hair in a far more feminine manner than I’d ever worn as I planned on cutting it all short for work that week anyway.  When John came in with the new bottle of wine he stopped dead in his tracks while Jenny and I posed for him.  I’m fairly certain that even though he knew it was me, my perfectly made up face, my feminine shape, and my newly styled hair had him fooled.  

Finally, after we all laughed at his reaction, Jenny excused herself to the restroom, leaving John and I to talk.  I knew something was up as soon as he sat right next to me and laid his hand casually on my knee. My chest tightened as my stomach dropped while John casually explained that while he loved Jenny and accepted just about everything about her, he didn’t like her having me still in her life.  At least not as Mark.  He planned today to take care of that problem by having me show Jenny I wanted to remain Maddy for her or he’d share the photo with her.  It didn’t really matter how he got it, it was still startling to see the photo of me getting a blow job from that hooker laid out on the table in front of us.  Jenny had never known about my infidelity during our rough patch and I know that if she found out she’d never want to see me again.  Not as Maddy or as Mark. 

Just as Jenny returned the photo found its way into John’s pocket.  I normally would have refused his offer to take us to a neighborhood picnic party, but could see his intent as he patted his pocket with the photo as he offered.  Jenny asking me if I was okay going out as Maddy was met with the fakest smile I ever wore and a nod.  Jenny actually drove us over while John continued with me in the backseat.  He said it was simple… once we were at the party he was going to tell Jenny that I wanted to come back and join them in bed.  That I wanted to be Maddy in every way to both of them.  That would leave me with three choices.  1, return with them and take the next step as Maddy’s girlfriend and now his Sissy.  2, tell Jenny that I didn’t want to be with a man and end up with the photo being shared.  Or 3, find my own way home and never see Jenny again. 

I already knew that I’d be taking option three.  As difficult as it would be to not see Jenny again, it was the only option that left me my manhood and Jenny’s love.  How hard could it be to find a ride?  It turns out it was a lot easier to find a ride than I thought, but the rides would all end up with far worse consequences.  The first person we saw as we came up to the picnic and got our drinks…. wine for Jenny and I, beer for John… was my own secretary Gina.  She was two things that made me want to avoid her at all costs.  She was a lesbian with a soft spot for stepfordized blonde women and a gossip that couldn’t keep a secret for more than a few seconds.  As I was made up, she would be drawn to me like a moth to the flame and if she found out who I truly was I’d be ruined at work. 

I stayed near John and Jenny until Gina was out of sight and then ditched them to find a ride.  While looking for a nice person I felt a tap on my shoulder.  Turning around I almost fell backward in surprise, seeing Gary, my neighbor from across the hall.  He was a known ladies man always on the prowl and we had both acted as the other’s wingman at different times.  So I knew that predatory look in his eyes as he offered to freshen up my drink.  I’d just never seen his lustful gaze directed at me before.  Accepting the drink, I tried to find a way out as Gary wasn’t the most open-minded guy and while it might not ruin our friendship if he found out who I was, it certainly would make it all around our building. 

As soon as Jenny and John came back into view I quickly found my way to them, even accepting John’s arm moving around my corset slimmed waist.  Jenny seemed flushed as she leaned in and breathlessly asked if I really did want to join her and John in bed.  She didn’t even give me a chance to answer before she giggled and said she’d always had a fantasy involving the two of us kneeling down and sharing a blowjob to a big strong man.  Without a denial from me, I saw that Jenny was taking it as acceptance on my part.  I could still politely disengage and find that ride without accepting John’s “offer” and therefore saving  my relationship with Jenny, but all I saw in the crowd was Gina and Gary both looking over at me.  In a split second I had to pick between being a girl in a way I never wanted with my ex-wife and her hunky new husband, having my work life ruined, having my home life ruined, or the very slim chance of avoiding Gary and Gina and finding another ride from a stranger. 

And now as I look up at John’s muscular body, as I feel Jenny’s hand rubbing up and down my bare back, as I hear her whispered encouraging words, as I feel John’s cock slip past my painted lips, I have to wonder if I made the right choice. 

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I initially thought I'd post this on my tumblr blog, but I felt it might fit in a little better here.  Plus, I can always add a bit more to a post here to the curious where I'm a lot more straightforward on tumblr with the story/obscura/caps posts.  So, what's the update?  I'm glad you asked.  

I'm almost done with Just Dance!!!

I've finished the story and am in edit mode.  Now, I've never written a story in this way.  This has taken me over two years to write with all the episodes of writers block.  I've never allowed myself the chance to come back to a supposedly 'dead' project and keep it going.  That lead to the story changing in ways that I hadn't expected as I got deeper and deeper into it.  For one thing, I started writing the story with the main character and his/her friend as having sex.  But as I got deeper into the story I realized I actually wanted the main character to be a virgin when he was 'forced' into having sex with his/her set-up boyfriend.  

Yeah, I know, I'm spilling some beans here but with the length of this story, I don't think I'm going to ruin anything.  Plus, would anybody read a story from me and NOT expect sex?  Yeah, I didn't think so.  

Anyway, editing it is quite the process.  I've already spent about twelve hours over four sessions editing it.   And I'm only halfway through.  Once I'm done with the edits, I'll have to break it up into natural parts, and then start posting it to Fictionmania.  I have a fairly open weekend so maybe... MAYBE... I could post the first part Sunday night and have it available to read Monday morning!? 

Even if I don't get it done this weekend, I'm in the home stretch.  I can't wait to share it!