My New Life Ch. 03 - Dressing up Bliss

Chapter Three-Dressing up Bliss

After putting on the Gaff and breast forms on I went to my closet and selected my lacy black set of lingerie. Slowly rolling the stockings up I my legs and clipping them to the garter belt, making sure the seams were straight just like my wife does, followed by another pair of black burlesque ruffled boy shorts, this time with Pink bows on. Putting the bra on was a struggle at first, this was my first time with breasts, and I just could not get them right, it was then that I remembered what my wife did. She put the bra on backwards, clipped it together, then twisted it so it was the right way and lent forward to settle her tits into the cups. The bra I had chosen was a shelf bra, so it showed the nipples off and uplifted my new boobs nicely. My excitement was rising and all I wanted to do was get some relief, but I knew that I needed to apply make-up so.....

..........I then went a sat at her dressing table and with a tutorial playing on watch-it online on my phone I carefully followed the instructions, Degrease the face all over completely, apply a suitable skin toned foundation, not to heavy and the using either a sponge pad or your fingertips apply some rogue and blend into the cheek bone area of your face. One final blend all over and you should have the a good foundation for your make up. It then went onto working on the eyes, with mascara, eye lash thickener and eye shadow and finally the lips, lipstick nice and thick, pucker those lips, kiss that tissue to remove excess, wipe any stray lipstick away and finally lip gloss with glitter for that extra kiss me quick look use lip liner. You may use lip liner in a darker shade just for that extra special guy.

It also stressed the importance of matching the nail polish on hands and feet, and recommended subtle shades of pink for a sissy, crimson red for a sissy slut and white for a sissy owned by a "Black Daddy" Again this was the first time that such a term was used in a video and at the end the watch-it online algorithm made some recommendations as to what to watch next.

Amongst these videos were the "Sissy hypno" type, whereby the use of flashing pictures and words the subject watching them was supposed to fall under the spell of them. I watched a couple and saved them to my hard drive, one I particularly liked which was just one phrase repeated with different video was, " If you like dressing up as a "GURL" and sucking cock it's not gay!" it showed several pictures of sexily dressed schoolgirls and milfs along with several shemales on their knees sucking a big black cock, no not sucking more like worshipping it lovingly.

Another one was called "Lock it or lose it" showed a crossdresser with a chastity cage on and fucking herself to a Sissygasm with big dildo, the precum dripping from the end of the cage making a pool on the floor which she then licked up. Whilst the last one was a "Deep Throat Face Fuck" it is every Sissy's dream to deep throat a big cock and to be face fucked. All this took me about 90 minutes I was satisfied with the end results of my make-up, so I went to my closet and chose my thigh high black boots, short leather mini skirt and black strappy low cut silk top. As I walked around my bedroom I heard the swishing sound made by my stockings gliding across the top of my thighs as the tight leather mini skirt kept my thighs pressed together and the click-clack of my heels on the wooden floor. The mini skirt was so tight that the suspender clips created little bumps in the leather, as I ran my hands over the top of my thighs I could feel them. The little red silk tabs used to help attached the clips to the stockings was just peeking from below the hem line of my skirt.

I then practiced my steps, lead with the heels, toes pointed, step flat and look straight ahead, sway your hips and finally to pick something up bend at the waist and show your stocking tops. I did all of this in front of the mirrored doors of the closets. I set my phone up on a stand and took several minutes of video I especially liked the one where I bent over and displayed my stocking tops and panty clad firm butt showing my frilly ruffles. The fabric stretched taut over my butt and a little bit of bare flesh between stocking tops and panties.

It was then that I felt my breast forms giving them a good feel, the sensation played out on my chest via then sensors soon had me aroused and after several minutes of play I messed in my panties. My orgasm seeping through and out of the slit in my gaff. It was strange feeling coming whilst soft, a more intense sort of orgasm that tickled and tingled from my balls and up my cock as my cum gently seeped from my "clitty" for at least three minutes and not in spurts which was normally over in seconds. At the end I was gasping for my breath as the orgasm rolled along, I could feel my cock weakly pulse a few times as the last few drops slipped out and I moaned with satisfaction.

I wanted more of them and decided I must try the dildo recommended by the gaff makers. The "Big-Boy vibrating and ejaculating dildo" by "Sissy Sister Services" a quick search on the www and I placed my order with express delivery for Monday.

My cum seeped through my panties and started to slip and slide down to the exposed top of my thigh as I walked, when it touched the stocking tops it made my upper thighs glide even more sexily this combined with the tight mini skirt gave me a second orgasm. I was wasted as I laid on the bed recovering from two of the intense orgasms I ever had in my life, I had just started to nod off when the first jolt of pain hit me.

I sat up, startled, and screamed aloud and wondered what had happened, after a minute or two I felt a rolling sharp pain from left to right over both breasts. I could not describe it, but it felt like being caned, memories of the time when I was caned at school when I was a "FAG" and failing in the task given by the sixth former at boarding school came flooding back. I felt five more roll across my chest, and I writhed in agony on the bed, I tried to turn them off, but I could not get the switch, to switch off. So, through my tears I headed to the computer, a more careful read soon showed me the error of my ways, and I knew I would have to endure at least three more hours of pain. The caning sensation would be interrupted by brief feelings of pleasure but the sensation I hated the most was the feeling of my nipples being clamped, now I understood the reason or the thumbscrew, little motors tightened and loosened the clamps at irregular intervals leaving them clamped shut for what seemed like eternity as the pain intensified when the screw was released making me scream in agony.

By the end of the third hour, I was babbling like a four-year-old, tears streaming down my cheeks, it was at this time I learnt mascara can and will run, my carefully applied make-up was ruined with long black streaks running down my cheeks and dripping onto my breasts. My nose was streaming great globs of mucus adding to the mess over my lips when I started to sob uncontrollably I sucked so much mucus down that I nearly became sick.

When at last the turn off icon flashed on the computer screen I could not do it fast enough, it was a mistake I would not make again that was for certain. Removing my top and bra I carefully removed my breast forms and examined the flesh around the area where they had been attached. I saw my extended nipples all red raw and puffy, to many to count long cane marks that showed across what would have been the meat of the breast form and a lot of small bruises. I also saw some mascara streaks that had managed to seep in-between them and my chest. Looking at myself in the mirror I was a total wreck, cum soaked panties from the orgasms I had from before being subjected to the pain and more from those I had when I felt the pain, which I did not know about till the end when I had fully understood how to operate them. It stated clearly in the instructions for the "PAINSLUT " option you may experience several deep and satisfying orgasms just from being subjected to the pain.

I gently removed my boots, clothes, lingerie, and gaff and left them in a heap and went to the bathroom, where I had a long and leisurely soak in a deep bath. After a long bath I then had to clean the breast forms and gaff, warm soapy water soon removed the mascara and using the slit in the gaff I flushed the last my cum out of the tube and left them both to dry on a towel.

My used panties I took to bed and placing them over my nose and mouth did what I had done wife my wife's panties. Because I had used the same perfume as she used I could not tell the difference and sucked and licked them clean. I was on a sexual high all night and even managed to have a wank and cum just by rubbing my cock with them.

I fell asleep looking forward to the next day........................

To be continued.