My New Life Ch. 12 - Anal Training Bliss

Chapter Twelve-Anal training Bliss.

The next day I got up and put a pale blue silk teddy on, and I sat at my computer looking at the video I took of me sucking on my new silicon best friend's cock. My limp clitty was soon straining at the silken cocoon surrounding it, my tent was clearly noticeable and precum was already making its presence felt. A small damp patch grew around the tip of my erect clitty on the silken fabric, making the tip feel all sexy and smooth as I rubbed my cock up and down, using the wet silk and sissy juice as a lubricant to ease the rubbing motion.

The video was a perfect turn on for me, for what I saw was a sexually dressed secretary crawling to her boss's cock and sucking on it. I watched the video several times before I noticed that my hands had raised my tight pencil skirt up to the top of my thighs exposing my stocking tops and panties, whilst one hand was busy rubbing my fake slit. Something I do not remember doing at the time!

The final shot where I turned to the camera showing my sperm covered face and hair, as it started rolling, dripping down, and trickling onto my breasts, my blouse, my glasses covered in a thick white viscous fluid and smeared lipstick, was too much for me and I came myself, it was a weak orgasm though but enough to calm me down.

But enough for what lay ahead.

That day I did not get dressed but stayed in my teddy and after I blew my new best friends cock a couple of times, getting deeper and deeper. This time I only quarter charged the balls, as I wanted to try and get used to sucking it, especially the way the secretary was instructed to do. Also, I had to learn to control my gag reflex as I began to take it deeper to the back of my throat. Soon I could take it to a fair depth but not the entire length. I looked at my progress along the shaft of the dildo, subtle hints of a red lipstick ring could be seen progressing down towards the balls. I took my hand and measured a spans length down the shaft. It was then that I began to wonder what it would feel like taking it in my anus for the first time.

Later I showered and shaved all over, making sure to remove stubble from hard-to-get places. I then took out my frilly pink baby doll nightie and matching pink girly boy shorts with white heart lace inset designs. I then put on a light make-up with subtle shades of pink and went a sat in front of my computer, I quickly accessed my account with watch-it online and searched for anal training videos.

The search showed all kinds of anal videos, so I had to narrow it down from all to specific, so in the key words search box, I entered; shemale, crossdresser and sissy. From this list I then first looked at shemale, they were really convincing as women and could take the largest of cocks with ease. I liked the one with Aleberry Scaite getting gang banged, what a turn on.

Then I switched to the crossdresser section with plenty of twinks riding cocks in all shapes, colours, and sizes, some of them were caged, some wore stockings and some very sexy lingerie indeed. Basically, they had either a suction type or free-standing type of dildo, with which they fucked their arses or boi pussy. The suction type they suck on doors, floors, and walls, and eased their boi-pussy gently onto the thick dildo. With the free style type, they pushed it into their boi-pussy and reamed it in and out quickly. In both cases they came without any physical contact with their clitty.

Boi-pussy? This was the first time I had heard of it, but I suppose it aptly describes the rear entrance on a sissy crossdresser, who was being fucked.

So, I now had two unfamiliar terms, one each for my penis and anus, also in the videos I watched the crossdresser mostly called the male character "Daddy," more role playing If I so wished!

One particular video broke down the insertion of a dildo into a boi-pussy very well, so I tried to follow it as much as I could.

So, I set my camaras in position, took the remotes with me and started to record my first anal training session.

Voices from a male character called "Coach" talking to a stocking clad caged sissy.

"Listen up SISSY BOI! You always follow my instructions, or you will be sorry, GOT THAT!"

In a commanding voice "coach" instructed his new Anal fucktoy, and you will call me "DADDY" from here-on-in sissy-boi!

ONE: You place your clean pre-lubed anus against the rather large thick veined cock of your DADDY and push, trying to work it in without it being too painful an experience. Lubricant helps only so far; you need to push against it as you push it in? Offering some resistance as the dildo slides in past your tight sphincter muscle, it begins to fill and over-power you as the feelings of pain give way to subtle hints of pleasure to come.

TWO: The DADDIES large cock slowly spreads your anus apart, stretching you making it feel like you are being split in two and making you moan like the eager cock slut you are. This is probably the worst part of taking a cock for the first time, pain, and pleasure mix equally, until you become acclimatised to having a full butt!

THREE: You arch your back and let out a long whimper, as you smoothly slide backwards and forwards onto his fat long lubricated shaft. As you speed up the pain gives way to waves of pleasure and your whimpers turn into grunts of ecstasy as DADDIES cock impales you balls deep.

FOUR: Now meeting little to no resistance from your sphincter or your brain, you pant and groan as you take in every inch of your lover's cock and slide up and down balls deep on your DADDIES cock. Rocking backwards and forwards on your heels feeling the cold of the wall tiles touch your butt cheeks, pumping......pumping up and down......up and down...........................................................................................................till..................................................till........................................................................

FIVE: Pre-cum dribbles from you, as your caged clitty restrained by the metal of the cage is bouncing backwards and forwards, as your DADDY fucks you hard and your own intense orgasm builds.

SIX: You pick up the pace, sliding, sliding up and down, in and out, faster, and faster as you try to milk every last drop of cum from DADDIES balls.

SEVEN: DADDY grabs your hair and pulls you violently onto his cock as he empties his balls deep inside of you. DADDY groans in satisfied pleasure as you whimper quietly impaled on his cock, your post orgasmic spasms thrusting you deeper onto the hard cock of your DADDY, as you spill your seed through the silk of your panties onto the floor.

Following the lead from the video I placed the suction dildo at a height on the bathroom wall tiles that would easily penetrate my virgin anus. The feeling is so intense; that I shudder in pleasure as I feel every inch of the huge dildo, split me in two, filling my virgin hole with a big fat plastic cock. I felt it bottom out.......................the cold tiles made me shudder as my butt cheeks flattened out as I pushed that dildo deep into my ravished boi-pussy, I was no longer a virgin, this was followed by a tickle of pubic hair against my ass cheeks, FUCK..................WHAT did I just feel pubic hair on my butt!!!!!!.

And then my DADDY starts slowly pumping in and out of you, slowly increasing the speed, each motion pushing you forward, toward your own orgasm, pre-cum freely leaking from the end of your chastity cage, pooling on the floor, dribble, drip, drip until a sizable amount had collected. Next time I Thought I really must put a glass on the floor to catch my SISSY SEED!

Eventually my DADDY slows down and he fills my rectum with his fat hot load of cum, finishing with a harsh spank to my buttocks, which pushes you over the edge, and this time your orgasm feels keener...as his final spasms rock into your stretched boi-pussy, forcing you to fall forward onto the arm of the sofa, whilst trapped between them you feel DADDIES spasms slowly die down as he reluctantly and with measured slowness, he finally pulls his cock from your ravaged arse leaving you with an empty feeling as it plops out, followed by a gush of thick creamy daddy cum, your first anal creampie. Your breathing slowly returns to normal as my DADDY says.

"Good sissy, I see you get the procedure. Now do not forget to practice slut, also I wager you enjoyed it too, judging by your moans and screams of pleasure. Before you leave slut clean my floor up of that mess you made and make sure you clean my cock, I am going home to my wife, and I do not want the smell of your shit on my cock!

So, I did as I was told and give his penis a sweet goodbye kiss, using my tongue and lips I cleaned his cock up removing all traces of our illicit sexual activity and smells from it. Then I licked the mess from the floor finally by pulling myself up his legs, I gave him a slow kiss on his semi-erect cock and walked away on wobbly legs.

I was caught in the fantasy of being my DADDIES cock sleeve and using my plastic boyfriend on myself, his words echoing in my mind as I slowly built my own momentum up. I took it all, the whole thing, without any problem at all, as I felt a warm sense of pride as I rode the dildo balls deep for all its worth.

I came just before the dildo did, and felt my spasms ripple through me, the automatic ejaculator working perfectly pumped my ravaged boi-pussy full of fake cum. My own orgasm slowly subsided as the dildo went into the final cycle of spasms, emptying its balls into my insides. As I drove the dildo deep into me, I felt the cold of the

I eased myself off my plastic boyfriend and with a loud plop, my anal gape, twitching with pleasure was large and round for all to see soon followed by my own first anal creampie. I turned around and without thinking and did what my DADDY told me to do. I took the dildo in my mouth and licked it clean. My creampie slowly spilled from my anus and trickled down my semi erect clitty it pooled on the floor, using my tongue I lapped up the spilled jism until the floor was clean. I turned to the camera, licked my lips, and blew my dildo a kiss. I slowly got up and walked somewhat painfully to my office chair, sitting down I replayed the video, watching my every move, and soon I fell asleep.

To my horror I awoke the next day with a painful neck and back, without getting undressed I ran a warm scented bubble bath and tried to ease my sore neck and back. Whilst I was in the bath my phone message alert dinged saying my toys would arrive within two hours. This gave me enough time to return to my man status, but I failed to take into consideration the scent from the bubble bath.

I decided that under my suit today I would wear my sexy black under wear set, so easing my panties up my shaved legs I snapped the thong onto place. I put on the lacy garter belt and eased first my foot then my shin and finally my upper thigh into the sexy black seamed silk stockings. I put on my low-cut bra and a white shirt, finally pulling over a grey lamb's wool jumper, black trousers and men's shoes and socks. It was a strange felling, feeling the swish of silk against my trousers, the constriction around my chest of the bra providing a little bit of cleavage. I could just make out the straps of the garter belt and clips but thought nothing of it. This was a significant risk to take, but I knew I had to sign for the parcel and to all outward appearances I was still very much a man.

I sat around for some time until the gate bell phone rang making my heart leap into my throat, as I spoke and let him in. My first encounter partially dressed how would it go I wonder?

To be continued.......