Extended Halloween

What happens when Halloween doesn't end?

It was the Halloween party.  My girlfriend Jeri had been trying to get me to dress up like a girl for months, promising me that her former boyfriends loved it.  I can’t deny that I was intrigued.  I mean, I met Jeri at Libeda the best fetish shop in town and she knew not only about all the toys and clothes and equipment they sold, she new how to use them.  She was their best sales girl and actually got me a job as an administrative assistant starting on November 2^nd.  So, Halloween seemed like a safe time to let her play and for me to experiment being her girl.  I certainly didn’t expect her to go all out.  She used four different products to remove my body hair and make my skin all smooth and glowing.  She got a wig that had to be worked into my own hair, then dyed it and my hair to match in the perfect shiny black. 

 The body enhancing tools must have cost a small fortune.  I mean, I knew I’d be wearing breast forms but I didn’t know they’d weight and wiggle like they did.  Nor did I think she could blend them into my own skin using that makeup and glue combination stuff.  Then there was ‘down there’.  The shorts… I really don’t have another word to call them… were designed to be worn for a long time as they gently had room to slide my cock into it and slid right up to my anus giving me full bathroom access.  And like the breast forms, they were glued and colored to match my own skin so that unless you looked close, I had a woman’s natural hips and ass as well as a pussy.    

 The clothes were another area where Jeri splurged.  A form fitting black leather hobble skirt, a white PVC top that made my breasts stand up proud and look huge.  Boots with four inch metal heels that clinked anytime I even adjusted my weight from foot to foot.  The corset with built in bustier underneath it all gave me that near hourglass figure.  Add on the fake bright red nails and the full makeup including bright red ‘fluffer’ lipstick and there’s just no way you’d recognize me.   

 I think everything would have gone fine.  The party was fine and everyone there just assumed I was a woman dressed up as a fetish doll.  After an hour of nerves and three or four cocktails I finally relaxed and enjoyed being looked at as a woman.  I danced with both men and woman and loved how no matter what, I was held and felt protected.  Maybe that’s why when the guy dressed up as a minotaur, bull mask and horns and everything else, asked me for a lap dance, I obliged.  With my fake ass grinding over his crotch, he whispered sweet nothings in my ear about me being tied up, kneeling before him, as he used me and my sexy mouth anyway he pleased.  Jeri was standing near, staring daggers at me and trying to get me to calm down, but I was having fun and this was her idea after all. 

 It probably sent the wrong message when I reached down and rubbed his fully aroused manhood and got hm to cum in his loincloth.  Leaving him with a flirty giggle and a wink was definitely a bad idea, but hey… its not like I’d ever see that guy again.  At least that’s what I thought. 

 It turns out that bull god was my future boss Derek.  While he was very open minded about the fetish community and accepted sexuality in every stripe, he was as hypermasculine and straight as they came.  If he found out that I, a slight androgynous male employee of his had not only attracted him but given him a lap dance with a happy ending, well I’d be more than fired.  I’d get Jeri canned as well since it would be clear I needed her help to look this good.  We left soon thereafter.

 When we got home, I tried to talk to Jeri about how I couldn’t possibly take the job now, but she pulled me into the bedroom, pushed me down onto the bed, and barely got her skirt and panties off before she sat down on my face.  It was the hottest, most raw, most feral, wild sex I’d ever had.  And my penis wasn’t a part of it at all.  At least not directly… she showed me that with a strap on she could ‘fuck’ my fake pussy and it would rub right over my cock.  I couldn’t get hard in the get-up, but with enough stimulation…. If she fucked me enough… I came and came and came.  It was clear in my head that this is why Jeri wanted to have me dress like a girl.  I knew she was bisexual, but I thought she liked men more.  Nope. 

 Sunday was calm and ccol and collected.  Jeri was still showing her dominant streak and had me make her breakfast, but I was happy to flit around the kitchen in one of her silk robes and nothing else.  I tried to bring up the job situation, about how I couldn’t show my face around Libeda ever again, but Jeri would just hush me with kisses or more overtly sexual play.  She showed me the joy of just about every sexual position I’d seen a woman in as she took me doggy style over our table, had me ride her reverse cowgirl on our bed, ride her lap in the chair, took me standing both from behind and face to face, and of course missionary with my heeled feet up on her shoulders.

 By the time Monday morning rolled around I was just following her groove.  I learned that I could shower with the body enhancers on and it only took a little touch up to make it blend into my skin again perfectly.  To anybody on the street I was still dressed as a fetish model, but I could tell Jeri was keeping it fairly conservative and safe.  I wore seamed dark stockings, tall stiletto patent leather heels, a black high waisted pencil skirt and a white silk blouse.  My makeup would look good for the evening but fit the bill for the ‘hot secretary’ look Jeri was obviously going for. 

 This is where you have to understand… I had complete trust in Jeri.  She’d shown me show much and I was happy to continue being her femmy dressed girly boy lover… just not all the time.  I thought she knew that.  So, I didn’t suspect a thing when we drove downtown.  I didn’t question it when we started walking toward Libeda.  It wasn’t until she turned and we stepped inside did I panic.  They’d just opened up so only employees were there so I kept my eyes low, fearing they’d recognize me from the party.  I shouldn’t have worried… Jeri made sure they remembered me, introducing me as the ‘doll’ from the party and Derek’s new secretary. 

 As I lean forward now and apply my lipstick, I think back on that first day at work two and a half months ago.  I wanted the floor to open me up and drop me down inside as Jeri introduced me to Derek.  As her girlfriend.  Derek was happy to show me around and just accepted that I had a cold and couldn’t talk.  So I couldn’t object as he put his arm around my waist and pulled me close.  I couldn’t say anything as his hand moved down to my hip and then my padded ass.  I couldn’t let anything out but a meek ‘eep’ when he turned me around in the storeroom and pulled me in for a kiss.  I panicked when his hands moved to my shoulders and he pushed me down to my knees, hearing his chuckling voice asking if I wanted to be tied up for our first time.  I was probably blushing pure red when Jeri came in and saved me from my first blowjob. 

 Saved isn’t exactly the right word.  Saved would have meant getting me out of there instead of the little desk in Derek’s outer office.  Saved would have meant me getting out of these clothes instead of filling out all of the tax paperwork as Libeda’s newest employee.  When we finally did get home Jeri just wouldn’t stop laughing and said she didn’t see any other way out of this.  She’d gotten me the job so if I didn’t show up it would be bad for her. She promised she’d help me however she could, but again our definitions were vastly different. 

 First, I didn’t see her tying me up, having me  kneel before her, and feeding me her thick strap-on as helping me.  I didn’t think of her coaching me on using a softer, quieter, more feminine version of my voice all the time as helping.  I certainly didn’t see her taking me shopping and buying me dozens of feminine outfits for work and home as helping.  But even now, after all that’s happened, after everything I’ve experienced, I see her desire to help me as the key thing.  She wanted to help me, so it doesn’t matter if everything she did trapped me further and further into this life.

 And Derek?  Well yeah, he’s given me a lot of experiences I never would have asked for.  I was able to avoid giving him a blowjob.  For a couple weeks at least.  I probably should have been suspicious when he wanted to try out a new manufacturer’s toys and had me try on the ring gag.  Writing the review about how it held my mouth open wide while allowing my lips to still lock around my guy’s cock was now on our site, right next to Derek’s review of how it fit tightly and kept a reluctant girl’s teeth out of the way.  I’m now as accustomed to Derek’s cock as I am to Jeri’s pussy. 

 Jeri did help me keep at least some of Derek’s attention away.  We’d take him out to the clubs until we found a girl that he liked and convinced her to go out with him.  I felt bad getting my boss girls, but when he was with another girl he had less interest in me at the store.  He still worked with me and insisted I help him try out new products or write reviews for our current stock so in the last ten weeks I’ve been laid out on his lap as he spanked me wearing latex panties with his bare hand or with my ‘bare’ enhanced ass with paddles and other implements.  He’s had me wear butt plugs so often that I’ll often forget that he doesn’t need it that particular day and still come to work with the little devil up my ass.  He’s given me dildos to use and didn’t know that Jeri wrote those reviews, but did like watching me demonstrate them. 

 But today is a new chapter.  I’ve had to listen to the lurid details of the last vapid valley girl I’d set Derek up with for the last three weekends and specifically how she loved anal and was making Derek love it just as much.  Well, they broke up last night.  This normally signals that he’s going to show more interest in sexually relieving himself in my mouth again, but I’m afraid between the bigger and bigger plugs he’s had me wearing and his new love of anal sex that he’s going to want to well and truly fuck me.  So while I haven’t stopped him from taking pleasure between my lips before, I’m now going full into it.  I’m making sure I’m wearing his favorite shiny red lipstick with its two stage extra shiny lip gloss topcoat as hopefully an overt sign that I want to suck him off. 

 Better to suck than get fucked. 

source:  fuskator