Sunday, September 27, 2015

Fantasy is not Reality

and Reality is not Fantasy!

This is a little different for an obscura.  Instead of a single image, a bit of story, and no words from me this obscura has 13 pictures, a bit of story for each, and an explanation from me at the bottom.  I've tried to space the images/narrative apart so that you can enjoy each piece without seeing what the next bit is going to be.  Lemme know if this works for you.

 Dressing up at my girlfriends when her roommates were away for the weekend was always the best.  I’m so lucky I found Kelli as we shared the same kinks.  Over time with her help I had struck the perfect balance.  My long hair and thin features would look perfectly normal in my every day life, but at her place I could become Tiffany.  My hair looked best in pigtails.  My legs were smooth so a short skirt could be used to show them off.  It didn’t take much makeup at all to make me look like a girl.  The breast forms were admittedly expensive and took forever to get right, but they added that last bit of realism. 

While she sent to her afternoon chem lab, I lounged on her bed and flipped through her diary.  Her Tiffany diary.   She wrote down her fantasies here involving me and they always got me so hot.  I couldn’t help the erection as I read about Kelli’s last entry.  Me lying in her bed when her….

OH SHIT!  I know that voice!  What’s he doing here!  Sharon’s boyfriend is such an asshat and a pig to boot.  Maybe if I just lay here quietly he won’t know I’m in here.  Fuck, he’s coming right toward the room.  He’ll just see me as one of Kelli’s friends… shit!  I knew I should have had my chastity cage on!  Think! Think! Think!  I know… lie on my belly.  That way he won’t spot my hardening clitty!

Ugh.  What A PIG!  At least he doesn’t recognize me, but now I can’t call him out on his lies.  I can’t believe he thinks this will work.  Telling me that Kelli told him all about her cute friend that would be using the place and acting like she’s setting us up.  But he did bring my favorite tea…. No Kelli won’t do that.  She knows that while I like to play the ‘getting caught’ game, that it’s just a fantasy. 

NO NO NO!  Don’t sit down!

Why does he act so brazenly?  Does he think I can’t see his eyes wandering over my ass?  I guess It’s a compliment in a way… he obviously sees me as a girl. Of course I can’t let him find out that I’m NOT a girl.  At best Sharon would never let me live it down.  At worst… well Sharon says he’s gotten into fights for the stupidest things and I know he could kick my ass. 

I’ll just act uninterested.  He’s thick but not that thick.  He’ll see that he’s not getting through and go down to the bar where he can get some interested prey. 

I knew I should have practiced my speaking voice more and now it’s biting me in the ass.  Er… having his hands on my ass.   I guess saying “No, I’m not that kind of girl” sound sexy when it’s said in this soft sultry whisper.  But if I say it in any other way he’s sure to recognize my voice.  Damn it, where’s Kelli?  Her lab ended a half hour ago!

Allright, lesson learned.  Saying “Kiss My Ass” in this voice does not get the desired response.   Whenever I’ve read scenes like this in stories it’s been a complete turn off… I may like dressing as a girl but that doesn’t mean I want to be with a guy.  So if it’s so gross…. Why is my hardon getting harder?

NO!!! He’s pulling my panties down!  I can’t let him see me like that!  I have to do something… ANYTHING!!   Showing him my breastforms is a risk, but they have a better chance of fooling him that seeing me back there!

Whew… that got his attention.  Wait… no don’t take your shirt off too!  EEP!

I guess the forms pass inspection, but being pulled into this position isn’t any better than him kissing my tush.  As realistic as these lil ta-tas look he’ll know their fake if he gets more than a cursory feel.   OH shit… why are his rough lips on my neck turning me on so much!  Come on Tifany think!

I’ll just scoot away.  He’ll see that as me not being interested and this will all stop.

Umm… that is NOT a sign of disinterest.

I’ve read the stories and they always seemed so improbable.  I mean no straight guy would ever do this… would ever allow himself to be put in this situation but now it’s staring me in the face.

I’m lying on a bed in my stockings and skirt and nothing else.  I can’t get up and leave without him seeing my now aching hardon.  And by getting as far away as possible I’ve just positioned my head over his crotch.  I guess I can’t blame him for pulling down his jeans.

Now I’m in that improbable story position.  I’m staring at a guy’s cock as his hand holds my shoulder, urging me closer.  Accept my defeat, earn my disgrace, have him beat the shit out of me and tell the whole world that I’m a sissy?  Or….

Is it written all over my face?  Probably not, but even if no one else sees it I’ll always picture that bright flashing sign hovering above me blinking COCKSUCKER.

Maybe I’ll have to thank Kelli.  She thought it was so hot having me suck on her dildo.  While we only did it that one time, at least I know how to make this look sexy.  Will she ever look at me the same now?  She’s said how she likes the idea of dating a girly boy, but the thought of me ever having sex with a guy turns her off as much as it does me.  No… I can’t ever let her find out about this.  I have to get this done quick as she’s sure to be home soon.

There’s something I never thought would go through my head…. How can I get this guy to cum faster? No, don’t put your hand on my head… wait, is he… he’s pulling me off!  Maybe he’s realized I’m not into this.  Maybe he’s not such a bad guy.   Umm…

I guess him taking his pants off isn’t a good sign.  But then again he isn’t returning to my newly christened cocksucker lips.  Why is he walking behind…


After all this, it Isn’t really a choice.  I can’t have gone through all of that only to have him find out now.  And if he looks, he’s GOING to find out.  Just take the situation in hand and get it done.  There…. Cock in hand, line it up, push back, give him a sexy moan, and just say it….

“Fuck me in the ass!”


OOF… He’s splitting me in two… UGH… I’ll never ask Kelli for anal ever aga…. OHHH…. He’s lifting me up into his thrusts…. GAAHHH… and it’s driving my own clitty into the bedspread….

Girly Boy.  Sissy.  Cocksucker.  And now on top of it all… I’m being fucked.  Well and thoroughly fucked.

Why does this turn me on so much?  Well I guess it is a fantasy.  Thank God it's not a reality!  I can’t wait for Kelli to come home though.  I’m going to have to give her a big thank you for writing out this particular version.  She obviously worked hard on it and it’s almost entirely believable.  

Maybe I’ll let her wear that strap on she showed me.  I could act it all out for her!

I don't normally write up for obscura's, but I wanted to share this.  This is kind of the process I used to do when I would look at image sets.  This was before the time of readily available video streaming and the broadband access that allows for video.  I would look at the images and pick out ones that fit my fantasy.  Sure, t here are a lot of images in those links that destroy this as a cross dresser trying to hide his 'male-ness' from a pushy guy.   Namely anything with her pussy in it.  But once I focused in on those images I would imagine a narrative...  something that would fit what the images gave me.  

The narratives almost always had a big gaping hole in it.  One that would require suspended belief.  Breasts, a guy not noticing a scrotum under the ass he's fucking, too feminine of a face... and this one is no different.  For this one though, with her fully clothed it works.... she has an ambiguity about her that allows almost complete belief that it's a cross dressed sissy laying on that bed.  So the rest... fantasy!


1 comment:

  1. Great story! Clever ending as well. The title should have given it away, but you made the original transition seamless to blur the line. Well done! :)