Prologue
My name is Chanel Michelle Kruger, I am a life long transvestite in my late thirties, the following story is a TRUE account of my first real experience as Chanel with a man. At the time I was a young 21 year old living in Johannesburg ? South Africa
I had spent the last fortnight or so conversing on the phone to a potential cross-dressing partner who I had met through a pretty backward dating service in one of the local papers,( South Africa at the time although had a gay scene was pretty limited in terms of cross dressing. ) We had eventually arranged to meet at my flat in Hillbrow and although I had already appeared in public before at several ?meetings? this was to be one of the first ?one on one? meetings with a person with similar tendencies.
I was fortunate at the time to be single and living in a reasonably secure flat on my own , as it had two bedrooms , I had fitted the second bedroom as ?channel?s ? and spent most of my time in the flat in the room trying out different looks and clothes. I had built up an enormous collection of girls ?necessities? and reveled in the fact that I did not have to hide any of it or put it safely away after I had been out or whatever.
Dave ( not his real name ) was in his forties and was married to what sounded like a very non supportive wife and was very eager to meet. This was way before the internet was available and we had not exchanged photos which was an ordeal in itself before the digital cameras became popular.
I was at the time in my twenties and had been dressing most of my adult life , I had perfected the professional look and was very happy with my passing.
I think it was on a Friday that we first arranged to meet , Daves wife was apparently going to be away for the evening and so he was effectively free for the night . Whilst Dave unfortunately had to travel ( to an unknown destination ) and was thus hesitant to dress for our first meeting, I on the other had had no such restrictions and was determined to look better that ever before. I had started my transformation as soon as I had got home from work , firstly by running a bath with my favourite lancome tresor bath scent , I had freshly shaved my legs and face to make sure that I had the perfect canvas to start my make up.
Ive always believed that foundation is the most important part of the make up process and was lucky at that stage not to have a heavy beard growth, once my foundation was perfect I had spent a long time with subtle contouring with a darker shades of base and blush, I still to this day love the smell of the revlons foundation face powder and liberally brushed on the powder before the ?colouring in? process began. Time for a quick courtleigh 120 cigarette and some close up critical inspection ? perfect !!
After about an hour I had completed the look I was aiming for and baring the lipstick ( always put that on after you are fully dressed ) had created a very sophisticated and precise look with included using liquid eyeliner , long extended lashes and smoky eyes.
Next and before my wig a had to get my foundation garments and clothing on , I remember that at that stage I had built up quite a collection of foundation underwear and preferred the under wired Playtex secrets range bras and matching panties that I had first bought on a shopping trip with a girl friend that new of my hobby. I had recently bought a very expensive pair of sheer black hold-up stockings and combined with a full contouring suspender belt / panty girdle( Straps removed ) provided me with the support I required and the option of removing my panties while remaining still clothed but accessible should the option arise ( pun intended ) I unfortunately did not at that stage have the budget ( or access to ) a fully boned corset but was in luckily in shape and did not have a real need for one.
My outerwear consisted of a fitted satin blouse ( still one of my favorites ) with a cowl neck and offset button arrangement , a green calf length slim-line skirt and matching jacket , I love winter clothing and most of my clothes reflect that.
With only my wig & lipstick to complete I started with my nails , Long nails were very much in fashion still and long false nails were readily available at most chemists , I preference at that stage was the ?Tess?, or ?Dynasty? range by Jonel , I had the application down to a fine art by then and had often been asked by interested parties if they were in fact my own , I am fortunate enough to have ( although large by women?s? standards ) very long and elegant fingers witch complemented my choice of nail length perfectly , I had spent many long hours with a former girlfriend , who had helped and accepted my cross dressing , doing each others nails on weekends. With a coat of Revlon ?vixen? which although not a perfect match to my favorite intended ?Brun Fresque ? lancome was close a enough match.
I only had one blond wig at the time, a mid length straight blond style , and had spent the previous evening washing , conditioning and getting the style right that I was looking for. It is important to freshly was the wig if you are going public as a fresh shampoo scent will do a lot to boost your confidence.
At about 6.45 I was, baring a last minute touch up to my lipstick, finished . and settled in the couch with another cigarette waiting for Dave to arrive.
At about 6 55 the was a buzz from the downstairs intercom and although I was expecting Dave I could not be sure that it was not someone else that I did not want to see , I answered hello in a semi female voice and hoped like hell it was not one of my college friends. Dave luckily promptly answered ?is Chanel there??, what a relief . I buzzed him up and quickly finished my cigarette, reapplied my lipstick and nervously waited at the door to the flat. Again I was fortunate to stay on the penthouse level which was again access controlled from the lifts which allowed me some freedom in the passage / corridor that led to my flat , It was easy enough to dash back into the flat should I hear anyone coming that might ( or might not ) recognize me.
I was so nervous I could hardly stand and had on several occasions considered somehow bailing (though I was now not sure how). The gate on my level buzzed, I opened it and gathering courage walked up the passage way to meet my ?date ?. Dave met me about half way down the passage, I could noticeably see his eyes widen at the site of me as he hesitantly asked ?Chanel? ?. Hi Dave , he lent forward and kissed my cheek ( a first for me at that stage ) I nervously invited him in, offered him a seat and a drink which he kindly accepted, I started into the kitchen and with shaking hands poured him a beer and myself a whiskey which was certainly needed.
When I returned he was sitting in the lounge and judging by the stare, was clearly either infatuated or just plain dumbfounded.
We spent the next 15-20 min discussing our various situations, His with a wife and how he very seldom dressed unless she was not around, his likes and dislikes, styles and fashions etc. but more importantly how difficult it was to find likeminded people.
I had managed to contain myself and maintain a certain amount of decorum but was still really nervous and decided to have a cigarette to calm my nerves, with a controlled shake I carefully lit a cigarette and in my most practiced pose exhaled high into the air, this seemed to break the ice and he asked me where I kept my things which I then offered to show him. I led him to ?Chanel?s? room and briefly showed him my dressing table, full cupboards and drawers. He seemed clearly drawn to my make up which was on display and I could almost see the longing to use some.
He then mentioned in an almost shaky voice how lucky I was and how he was getting hard just by looking at me and my extensive wardrobe. I am still not sure if it was the whiskey in me or how I managed to get out my next words ? I asked him if I could feel how hard he was, which by looking at his trousers he clearly was.
His penis had somehow managed to work its way into a sideways vertical position which left a distinct outline in his trousers, he answered ?yes please? and I slowly moved my long nailed right hand down to hispenis and slowly & gently started to massage his angled bulge. We were now in the doorway from my room into the lounge and time appeared to be standing still. Dave was slightly taller than me ( even in my heels ) and collapsed against the door frame, I?m not sure how long we stood without any words being spoken but it must have been a good minute and a half before he blurted out that he would cum if I didn?t stop. These words seemed to bring me out from the spell cast on me, my long cigarette was almost finished and I managed to take a controlled inhale and exhale before he managed to recover to the point where he could stand up and push himself off the wall that he had collapsed onto.
I might have been brought out from the spell but had at that point without any conscious thought already decided what I was about to do. ?come into the lounge, I want to taste you? I said as I left the room, I walked to my coffee table by the couch and put out my cigarette.
?where? he asked as he followed, already starting to remove his trousers , I motioned him to one of the two seater couches I had in the lounge, but before he removed his boxers he suddenly seemed nervous about the fact that my curtains were still open and questioned that the neighbors might see something . My flat was on the eighteenth floor and although knew there was not much chance of anyone seeing anything, I think that I may have unconsciously left them open on purpose, after all, all someone would see was a hopefully good looking woman giving her man a great blowjob, His nervousness prevailed and I submitted by closing the curtains for him. Before I got back he had removed his boxers and was sitting with his back on the armrests and both feet up on the couch (obviously his preferred position). I gently eased myself down onto my knees and took a few seconds to admire my prize. Whilst Dave might not have been the most attractive man around , his penis was magnificent, until that point I had never seen an erect penis other than my own and Dave?s was certainly a lot bigger than mine! I imagine it was at least 9-10 inches and really quite thick.
Suddenly everything then seemed to flow into a surreal, automated slow motion. His hands were at his sides, careful not to get into the way. I first reached out my left hand onto his member (a position where he could visually appreciate my long painted nails against the white of his penis) and gently scraped my index finger from his opening down the top side down to his belly and back. At this point I wasn?t paying much attention to Dave as it was only his penis that had me mesmerized, I them moved my right had up and while leaving a nail on the opening started the same process with my left hand down the under side of his penis to his balls, carefully only letting the tips of my nails do the work. His penis was now at full erection, all the veins were exposed and the head was as shiny as a bowling ball ( and almost as large or so I thought ) and was starting to twitch slightly against way from my fingernails.
Time to get this show on the road!!
In a relative sudden burst of speed I reseated myself on my knees, swept my hair back behind my ears on my left side ( I had always dreamt that this was the way I would do it , the way I had seen it done in the movies that I had watched ) and simultaneously lowered my head, and with my left hand lifted his now pulsing penis off his stomach to meet my mouth, I could not wait any longer and just did not have the willpower to tease him any longer with my tongue , this one was for me !
In one swoop I engulfed his entire throbbing head and proceeded on downwards albeit slowly. I did not try to deep throat him but stayed deep enough for my comfort, on my slow withdrawal I once again tucked my hair back and twisted my head towards his face purposefully making my first eye contact with him since we had begun, It was only then that I noticed his face , he wore an expression of utter amazement mixed with, what under any other circumstances could be interpreted as, excruciating pain, I then using my eyes smiled at him and only then did he let out a long , loud and guttural growl, I think this may have been his first real breath he?d taken for a while.
At very least he seemed to be enjoying my first ever Blowjob and this spurred me on to up the pace. Using the finger tips and thumb to help, I now was hell bent on getting this magnificent serpent like being to release itself within my mouth.
Dave hesitantly attempted to put his hand on the back of my head but I wasn?t ready for that and waved him away without releasing his penis, he obviously under stood and let me carry on with out his help. Within a minute he was reaching the point of no return and I already had started to taste what I now recognize as pre-cum, his hips started to thrust slightly and he in a shouted breathlessly ?I?m going to cum Baby?.
I think he was looking for confirmation from me that this was okay, (although I had often fantasized about finishing off a blowjob with my mouth slightly away from its head to catch the inevitable from a distance) there was no way I was about to let this one out of my mouth, I again turned my eyes and blinked my consent to him. I swapped hands to let my right hand down to rub and pump his now tight balls. He immediately started thrusting his hips with out abandon. Within seconds of his warning I received my very first gulp of warm cum which was instantly followed by a HUGE second load!, I would imagine about six or seven spurts erupted from him before his uncontrolled thrusting subsided leaving him twitching & jerking still within my mouth which I maintained tightly sealed around the head of his penis. Although my mouth was almost overflowing I had luckily had started to swallow as he first erupted and managed to keep the majority from leaking out down his shaft. He was still twitching as I slowly lowered my mouth down his shaft in a final effort to retrieve the small amounts of less consistent cum which I had wasted. On my upstroke I kept my lips tightly around him and slowly lifted my mouth from him then gave his penis one last gentle kiss and tickle with my tongue. I then sat back on my haunches and looked up at Dave and smiled. He was till sitting in the same position with his mouth slightly open and appeared utterly exhausted. My right hand was still on his now lipstick coated penis and I was slowly playing with him. He brought his head up from the armrest and said ?God, you?ve done that before!
?No that was my first, How did I do ? ? I asked
?That was the best head I?ve ever had , God , your lipstick looks so good on my cock?
I was acutely aware that my make up might have become smudged and wanted to check it,
?I just need to check my lipstick Baby, wait here?
I got up fetched my purse off the coffee table and went into the bathroom, I still could not believe what I had just done and literally said to myself in the mirror ?yep , you are now a cocksucker!?
I had not yet cum and my cock was still extremely hard and uncomfortable tucked back in my panties, with one palm roughly rubbing between my legs I removed my lipstick from my purse and attempted to repair the damage to my previously immaculate lips. I was almost bending over from the pressure within my panties and I realized that I had to get some control back and fight the urge to pull my clitty out and get myself off right there in the bathroom.
I did a quick fix to my lips, took a deep breath and returned to the lounge. Dave was now sitting properly in the chair with his penis still out, remarkably it still appeared to be rock hard, he was gently playing with himself and as I walked in and he asked how I was doing, I said I was okay.
?Did you cum?? he asked
?No, not yet? I replied
He then got up, and walked to me with his penis jutting straight out , he then took my shoulder and led me back to sit on the couch ?here, let me help you then ?
Before I sat down I had to slip out of my skirt which I folded and hung over the back of the dining room chair and returned to sit on the couch and although it would have been more lady like to sit with my legs crossed, in the current situation it perfectly acceptable to sit with my legs slightly apart.
Dave half sat down on the couch next to me and leaned over to kiss me whilst simultaneously reaching for my swollen panties and started to rub. His penis was again now rock hard and was within reach so I reciprocated. With the rubbing on my panties my clitty was slowly being eased out from between my legs to a point where the head was peaking out the side of my panties. Dave noticed, licked his finger and started to massage my clitty head in slow circles with his finger tip. I was now at the point where I was leaning back on the couch with my head back and eyes closed, lost in the sensations that I was feeling. I think I had even stopped rubbing him and just held his penis firmly with my hand as he started to pull my foreskin back between his fingers.
?Lets get you out of these? Dave said, referring to my panties.
Luckily I was, as previously mentioned, wearing hold up stockings and could easily remove them without having to adjust my suspender belts etc, I merely lifted my bottom and Dave removed them, careful to stretch them over my rock hard little clitty.
My 6« inch clitty was nowhere near the size or girth of Dave?s monster and has a distinct curve to it. I had, had several girlfriends before and although I could always satisfy them it was always embarrassing to show them my penis for the first time. This time it was different, I was almost proud of my little clitty.
Dave also seemed to understand that he did not need to compliment the size of my clitty but seemed intrigued by it?s unusual curve and later on in our relation ship would referrer to it as his baby?s little banana clitty.
I was by now completely at ease and although desperately horny was no longer nervous about was I was doing or who was doing it to me.
I reached out again for his cock and started to pump it while Dave did the same for me. My left hand was free to rub my breasts and it was literally seconds before I started to cum. I shot my first droplet almost across the room, Dave lunged down to try and catch the follow ups but started to cum himself before I had finished which seriously hampered his flexibility. Although Dave had cum earlier he still managed to cover my wrist and blouse sleeve with his seed, I even had some further up on my shirt but that may have been from me. Dave collapsed on my lap for a few seconds before sitting up and forcing me to let go of his penis. His hand was also glistening with cum and he brought it up to my mouth to taste before licking some of it up himself, I now lifted my cum covered hand to my lips and noticed the distinct differences in the tastes. I suppose because I had tasted my own cum before I may have just been more used to it , Dave?s cum was definitely more pungent, I decided I liked it a lot.
Dave had to clean up and left me in the lounge to have a cigarette and recover, by the time he returned I was playing with myself again.
?I have to go Chanel girl, I don?t want to but I have to? he said as he stood there
?Maybe next time we can spend some more time? Thanks so much for coming Dave? I said as I got up off the couch and walked him to the door.
?Do you have everything, your keys & phone?? As I turned he leaned in to me for a kiss but it was obvious his goal was under my girdle which he was again rubbing with his left hand. I leaned into him with my head on his shoulder and put my hands around his shoulders . It was the first real sensual hug I had ever been in with a man, I felt incredibly safe and warm and although I was still horny the feeling of togetherness was later to become more confusing to me than the sex that we experienced. I reluctantly let Dave out and gave him a final peck on the cheek in the corridor with the promise to see each other again ( this still without a skirt and with my clitty clearly visible to all)
I had just had my first successful sexual encounter as Chanel with a man and whilst I was still in Chanel mode, I felt wonderful, but this experience would prove to be the start of a long confused journey of self discovery.
I hope you enjoyed my TRUE story, I would greatly appreciate any feedback or comments that you may have. I would like to write about my other experiences should anyone be interested
PS Dave if you remember this, I would love to hear from you again
XXX
Chanel Michelle Kruger
E-Mail ? chanelkruger106@hotmail.com