A Sissies Dilemma Pt. 01

Hi all, this is my first attempt at erotic fiction and I hope you enjoy and don't judge it to harshly. The story is about 30% fact and 70% fiction but 100% me

..............................................................................

IT had seemed like the beginning of such a perfect day but little did I realize what was to come and what I would have to do to try and keep my secret..........

As Mondays go this was looking like being one of my favorites in a long time, a whole day with the house to myself and a couple of new outfits to try on plus a couple of new toys to play with.

I still thought of myself as a normal enough guy, maybe a little kinky, but a normal enough guy who just liked to feminize occasionally. Sure I was probably a bit serious about trying to get it right even growing my hair long and making certain the rest of me was smooth as silk, but if I was going to be a girl I wanted to be a hot one. At about 5' 6" and 65 kilo's I had always been on the smaller size which had ruled me out of a lot of sports, so through no choice of mine I had ended up on the gymnastics squad which resulted in a very flexible body, and yes I can get my feet behind my head.

Now that my nails were dry, a sexy sparkly red, I couldn't wait to put on my stockings, black hold ups with a seam and totally sheer so my painted toenails glistened underneath. A lacy black bra and matching g-string came next sending shudders through me as the thong rubbed against my butt hole giving me another idea.

Opening up one of the packages on the bed I found a toy I had been waiting until today to use, my new vibrating butt plug. I slid the plug into my mouth coating it with thick saliva. At 6 inches long flaring to 3 inches round at it's base it seemed the perfect size as i slowly eased it into my boi pussy, stretching my hole until the widest part was sucked inside me, making me gasp with pleasure.

Grabbing the remote I put it on its lowest setting and felt the plug come alive inside me, the little beads massaging my sphincter whilst the vibrations caused ripples of pleasure. Already the front nylon panel of my g-string was starting to moisten from the pre cum starting to leak from my little cockette, it wasn't really big enough to be called a cock.

Choosing a pair of platform 5 inch heels, shiny black with an open toe, I sat back on the bed to do up the buckle, Immediately the butt plug pushed further inside me causing me to spasm in delight as the tip massaged my prostate. I felt so horny now I wanted to start playing but new if I started I wouldn't finish dressing, so instead I grabbed the new schoolgirl skirt and daintily stepped into it.

The skirt came to just above my stocking tops, its red tartan pattern seemed the obvious choice for a slutty schoolgirl look. The outfits top had a cute little tartan collar and cuffs whilst the rest of it was sheer black stretchy nylon which tied together leaving my midriff bare.

Doing a little twirl in front of the mirror I went to my desk and sat down, relishing how the plug once more pushed deeper inside me. Grabbing my lipstick I quickly applied a coat which matched nails whilst pondering the eye make-up. Dark and slutty or light and subtle and I new right away which one as the black eye liner went on. Thick mascara and and a little blue eye shadow and I really looked like I belonged in a porno which hopefully would look nice in any selfies I took.

Lastly I released my hair from it's pony tail and gave it a back brush to let the curls come out, loving the way the blond hair softened my face and completed my girly look.

I loved the way dressing up made me feel, like I was a different person, not a shy and awkward guy but a hot sissy girl, even if it was just me in my bedroom dancing in front of my wardrobe mirror. I could feel the butt plug pulsing inside me but looking down on the bed I realized I wanted to try my other new toy.

Laying back down on the bed I watched my reflection as I slowly eased the plug out, loving the way it left my boi pussy with a little gape which I quickly slid my finger into, loving the way I could watch myself finger bang my hole. My cockette started to swell, my other hand rubbing it, squeezing the pre cum out onto my finger which was quickly licked clean, mmmm.

The new vibrating dong was 8 inches long and so realistic I couldn't resist it when I saw it, and it had a suction cap on the end for when you wanted your hands free. It definitely wasn't a beginners toy but I had been play with toys for a while now and felt the need to stretch myself, in more ways than one.

The dvd which was playing was coming to my favorite part, a sissy schoolgirl getting spit roasted by two guys [hence my outfit] so I grabbed my lube and greased up my new friend. Slowly pushing it into my ass I felt my ring stretch to accommodate it, loving the way it made me feel so full as it slid deeper inside me, until with a final push and a gasp it was fully inside me. Switching the vibrate function on I felt like I was going to explode as I started to fuck myself, moaning and gasping as I tried to keep in time with the movie, imagining I was the sissy in the film.

Knowing I wanted to taste myself I pulled my feet back over my head until my cockette was dangling over my mouth, a strand of pre cum connecting it to my tongue. With the dong still sliding in and out I new that even though I wasn't fully hard my cum would soon coat my face and fill my mouth and leave me a slutty mess.

Suddenly the room went quiet, the only noise my moans and the squelching sound of the dong as it popped out. A fearfulness gripped me, panic as I new if my mother caught me like this I would be thrown out and everyone would know why. Even the few friends I had probably wouldn't understand.

All this flashed through my head in a second as I struggled to change position and sit up, frantically trying to think of any excuse, other than the truth.

Finally looking round I realized I had been caught, but not by mum but by Chris, her longtime friend and hairdresser who stood in the doorway, his phone in his hand and a wicked smile on his face. Chris's other hand was massaging the bulge in the front of his jeans and I felt myself turn even redder when I felt I had been caught staring at it.

"Please don't stop your performance on my account," Chris said, slowly walking across the room keeping the phone pointed in my direction.

"I was just uh.... well I ummm, please don't tell anyone" I blurted, feeling a tear start to run down my cheek.

Chris reached out, his thumb wiping away the tear from my cheek before slowly sliding it over my lips.

"The problem as I see it is that I really should tell your mother" Chris said, his thumb still pushed against my lips stopping me from speaking.

"The other thing is I have friends who would love to see this video I shot, some who know you and some who would like to, so what are you willing to do to change my mind." Chris's thumb slid between my lips touching the tip of my tongue causing shivers to run up my spine.

My mind was racing still trying to think of some half believable lie to explain my state when I realized the meaning of his words. Sure when I was dressed and in the moment I wanted to be a sissy slut but now I wasn't so sure, maybe it was a step to far. This was my fantasy self that no one else was supposed to know about, a little bit of harmless fun and now I was caught I could feel more tears welling up in my eyes.

Chris's thumb left my mouth hooking under my chin tilting my head back so I was looking up into his eyes, the camera still focused on me.

"Hears the deal, either you take my cock out and give me a blow job or I press send on this video and in a town this small half the people will know your secret before the night's out. Probably the other half by the end of the week, including your religious mother who will without a shadow of doubt throw you out. Then who knows what an unqualified little sissy like you will have to do, but I wouldn't be surprised if it doesn't include sucking dick" he said with a smile.

"Now I will give you 10 seconds to decide but if your not starting I will press send and leave you to enjoy the rest of your day, either way it's your choice, and you might enjoy it"

I could hear the humor in his voice and new he didn't care if he destroyed me, to him it was just a game, one he would win either way. As the numbers in my head counted down I new I was to weak risk it, a real sissy in more ways than one.

Placing my hand on the bulge in his trousers I looked up at him and mumbled "okay," realizing that one quick head job was better than a lifetime of total humiliation.

"One more thing you need to do first. I need you to look into the camera and convince me you want to suck me off. You can beg, plead, be a slut, I don't care as long as daddies convinced, Sammantha."

The shock must have shown on my face as this was to be my name if I had been a girl, something my mother loved to tell everyone given half a chance. Quickly I composed myself and realized if I was going to do this I should model myself on the sissy on the dvd, be someone else for the next 10 minutes and get it over with.

Running my finger up and down his bulge I looked into the camera and started to speak in my best girly voice, "Please daddy can I play with your cock, I've been a good girl and done all my homework so can I please suck your cock. I promise to not stop until I swallow every drop or you can give me a sticky facial, please daddy,"

I couldn't believe how easily the words came from my lips and judging from the smile on Chris's face I had passed the first hurdle, Keeping the camera on me he nodded for me to continue and I new that doing the deed was going to be a lot tougher than speaking some porno movie lines.

As my finger kept rubbing at his bulge my other hand undid his trouser button and then his zipper. With both hands I pulled his trousers down until they slid to the floor. Leaning forward but still looking up into the camera I started to gently kiss the swelling in his pants, nuzzling into his cock, smelling his musky scent His cock seemed even bigger now and a sticky damp patch had made his underwear almost see through, his knob seemed to be straining for release. I kissed the end of his cock through the material, my lipstick leaving red marks on the wet cotton.

I was becoming that sissy in the porno and there was no doubt as I started to tug down his pants that he was totally aroused and even if I wanted to stop he wouldn't be in the mood to let me.

Chris's cock was at least 9 inches long and thicker than my dong, which I guess seemed to suit his 6 foot height. Wrapping my hand around his cock I started to slowly rub up and down, the pre cum and saliva making it easier for my hand to slide on his meat.. If I had to suck a cock I would have preferred to start with something smaller, but other than that it was pretty perfect.

Leaning forward again I started by kissing and sucking on his smooth balls, feeling there fullness in my mouth whilst rolling my tongue around them. I kept stroking his shaft while I did this, speeding up and slowing down thinking maybe I could make him cum without putting his cock in my mouth.

Almost as though he new what I was up to he grabbed a fistful of my hair pulling my head up so my lips were level with his knob, " you wouldn't want me to cum without sucking me now would you sissy" he said, His grip on my hair tightened, "now open your mouth Sammantha and be a good girl for daddy."

I started to lick his shaft running my tongue up to the eye of his cock and got my first taste of fresh pre cum, sticky and a little salty but not so bad. Opening my lips I started to suck on his knob, my tongue swirling around it lapping at the pre cum that freely flowed. I could see myself in the mirror, a slutty sissy schoolgirl sucking her daddies cock and by the look of it really enjoying it. What was happening to me, I just needed to get it done and move on and try and forget.

Chris's hand moved to the back of my head, cupping it as he slowly started to move his hips backwards and forwards. Luckily I still had one hand around his shaft so only a little more cock entered my mouth. My other hand fondled his balls gently pulling and squeezing them, hoping it would soon be over.

Realizing he had stopped moving I looked up into his eyes, fearing I had done something wrong, not knowing what would happen next.

"Sammantha I want you to move take your hand of my cock and put your dildo back in your little boi pussy, NOW" he commanded, his tone leaving no room for argument.

I rose off the bed just enough to line up the head of the dildo with my still wet boi pussy before sitting back down on it. The vibrations started to tingle inside me making me feel horny which in turn made me feel ashamed, ashamed to be doing something against my will yet realizing I was enjoying it.

Chris's hand still cupped my head and now with no hand on his cock I was powerless to stop him from fully filling my mouth. His hips started moving quicker with more force, his hand pulling my head forward to meet his thrusts until I started to gag. When this happened he would pull out slightly allowing me a quick gasp of air before driving his cock back in deeper than before. I felt sick and dizzy, black mascara tears running running down my cheeks and still he showed no mercy. My mouth was his fuck hole and my ass felt so full from sitting with all my weight on the dildo that I thought I would never be able to stand or walk again.

Chris's moans filled the room and I new he couldn't be far of coming. I tried to pull my head back slightly but he wasn't having any of it, instead pulling me even closer so I could feel him in my throat. His cock stated to spasm and I could feel his legs shake as I tried to push him back, but instead I felt the first powerful jet of cum go straight down my throat. As I gagged I felt Chris release my head. I pulled back and felt cum fill my mouth until his cock was clear of my lips but still thick strands erupted from him coating my face and neck, marking me as his sissy slut. I felt like I was drowning in cum and as I gasped for air I could feel the thick globs sliding down my throat, swallowing my daddies load.

Looking in the mirror I saw my face covered in cum, dripping off my chin landing onto my stockings. The crying had made my makeup run, my lipstick was smeared everywhere and I could even see cum in my hair. But even worse was the puddle of cum in my panties, I had orgasmed and not even realized'

.

Chris smiled down at me, "not bad for your first time and it's certainly not going to be your last."

To be continued