Pleasuring Carolyn.. for her a primary role.

Guys as girlie’s, well that’s about it for me, my sexuality in a nutshell I expect, human sexuality is an amazing thing as we all have our own little likes and dislikes. Am I gay? As I have explored the possibility of that over many years. Or are there degrees of gayness from being fully gay or just a bit gay. Or maybe I am bisexual in my outlook, and too be honest I guess I would feel more comfortable with a label like that. Certainly if I had to choose one from another. Then what about being normal? Well are any of us normal and what do being normal really mean!! for me I will rest at being bisexual with more than a leaning towards cross dressing and feeling more than a little feminine.

Let me demonstrate a little for you, a day or so ago I realised that a considerable time had elapsed since I indulged myself in a little personal pleasure. I guess I am no different from anyone else who gets a little hot down there as little activity brings on a yearning to please your inner self in a very delightful way. So Carolyn joined me in the quietness of my bedroom. She knows what I like to see and laughed a little as she went through our little special bag that we keep on hand. She selected some black tights to cover her wonderful legs which took on an amazing shape as she rolled them up over her thighs and allowing the elastic to fasten them in place.

Again she gave me one of her looks and ran her fingers gently across a pair of turquoise French style short knickers. Full of lace and very feminine. She motioned to me and watched as my mouth went dry with desire. “of course sweetheart” my words almost stuck in my throat with the dryness. I watched transfixed as she slid them up and over her recently applied tights. Again I watched transfixed to the action that was being played out in front of me. Her fingers sort out her bra and catching it backwards and reversed, she proceeded to clip it in to position from the front and spin it into position.

I knew in an instant what dress she was going to entice me with as her eyes transfixed them selves on mine. Oh, Carolyn!! I head my little almost audible voice croak out. As she once again lifted for me too see a little creation from the Roman Original stable, For she knew my weakness for this dress. I feasted with the drama as she wiggled and eased this very curvaceous attire reshaping her body as it finally found its form. She then spent a little time combing and reshaping her gorgeous short blonde hair.

She never allowed herself to look shaggy in her hair which she loved to brush time and time again, and I alone appreciated the effort she put in. although her sexuality was very much entwined with mine as in essence we are both one person and share the same experience sexually.

Although she had not as yet finished, I took a moment to glance down at my own cock and it was by now clearly reacting to the visual stimulation that Carolyn was creating as her influence overwhelmed my senses. The dryness of my throat now was very apparent as I tried to say how lovely you were looking. I couldn't help but to just allow my fingers tips to brush across my now swollen glans and gasp as a little string of pre- copious lubrication adhered to my finger tips. It felt like a jolt of electricity pulsing from my cock to all extremities of my body. And I shudded a little with the pleasure.

She shot me a look and told me to be careful as she was not yet in a position to explore our unified sexuality and certainly took a very dim view about little accidents that may ruin the final thrill for both of us. I agreed and withdrew my pleasing fingers from my hardness, this only increased the feeling of desire for what was to come. That agonising time of applying makeup came around and I knew I had to endure this torturesome wait for her to finish. My engorged cock wasn't at all helping matters by ejecting a constant stream of silver lubricant upon the bed clothes. She applied some creamy foundation fluid and smoothed it out across her face, the transformation was amazing and her natural colours seemed to blend and remove the agedness from her features.,
A little eye shadow to draw me in was quickly applied followed by some contour pencilling to create a pleasing face feature. I marvelled at her dexterity as Carolyn next transformed her eye brows from something very ordinary to what only could be described as soul catching in its entirety. Carolyn knows for well that I am transfixed by women’s stunning eyebrows and took extra time to see they were right. My hardness was so much in control at this point and her look dared me to touch myself to reduce the desire that was raging throughout my loins.

All I could do was to watch as the little pool of pre cum steadily oozed down upon the bedding, OMG, I wanted her tender touch so much that I whimpered and moaned quietly in a very wanting way, she rightly ignored my musings as she continued with her preparations for pleasure. In a way Carolyn was my creation but she so controls me with these self pleasuring situations that I desperately desire. Once more she tantalised my very emotions by reaching into her handbag to retrieve a lipstick. Pink or my favourite deep red perhaps, just a gloss across their natural colour would have sufficed in the heightened sexual state that I was entering into rapidly.

I heard the lid top click and fall away to the floor and to my delight I saw it was my favourite deep almost aubergine coloured lipstick. I watched her every move as her fingers twisted the little mechanism at its base and saw almost memorised as the pointed contents drew its self up to full length. She half turned towards me with a little rye smile and allowed the tip to mark her lips and darken the flesh. Again I felt an electric jolt as I took in the erotic scene that was now being played out before my eyes. My hips naturally thrust forward and upwards trying desperately to get some friction on my cock to alleviate the crashing feeling that was currently raging through my head and loins.

She caught my eye again and a look that told me that it wouldn't be beneficial to allow myself to secoumbe to her charms in this uncontrolled way. Once she saw me relax a little, Carolyn continued to paint her lips, and I watched this transformation with increasing awe to how she could possibly turn me on in this extreme manor. My gaze took me momentarily away from her actions and down towards my own erection. Straight and fully inflated with the protecting hood drawn fully back. The tip a red rich purple colour showing almost translucent view of the blood supply that was powering this spectacular event. It was just one of those times when every thing seems to work just how nature had intended.

I felt a small pulse of muscular spasm buried deep inside this throbbing member, a moment later I saw the tip open up and a silvery bead of clear liquid ejaculated from its delivery slit. Astonished I watched it gather pace and start a downward journey coating the fleshy rod as it headed south and joined up with many others that had taken the same route. She then applied a final stroke from the lipstick dispenser and replaced the cap to prevent it drying out to soon. With a roll of her lips and a little application of a wet wipe, perfection was achieved with her face and she smiled back at me to accept my admiration. Reaching forward she took a little bottle of Nina Ricci perfume and gently sprayed it into the air, allowing the droplets to fall back on both of us and infuse the air. The effect on my nostrils and physical state was immediate.

My mind seemed to go into overdrive as the perfume hit and sent strong message's all the way through my nervous system to my lower regions which responded by trying to enlarge even more than nature had designed for. I felt as if I was in un-charted territory and all that was destined to happen was in a way coming my way. I stared, unable it seems to intervene as my hardened rod took on a life and seemingly controlled me. Carolyn was also watching no doubt pleased with herself that she was the object of this self induced state that I was currently suffering with her very much in control.

The first touch was almost un bearable as she slid her index finger from the base of my erection in an upward direction towards the glans. My eyes almost seemingly popped out of there sockets as her painted nailed finger cut a swathe through the silvery lubrication that was still trickling down my pride and joy. I watched as she smiled a little, almost a wicked and intended look that implied that I needed to accept the rules that benefited her more than me. I half nodded and accepted in my head, although no vocal agreement had ever been voiced. She turned away for a moment and leaned towards the floor. In her hand I saw her take hold of her lovely little black gloss leather court shoes with a not to high heel. Only about four inches in height I would say. With one foot she easily eased herself into it and I expected her to do the same with the other shoe. But she raised it up and held it out in front of me. My eyes and mind tried to understand why she was doing this?

It all became clear a few moments later when she made the heel to contact with my already painful rod that was displaying signs of her cruelty. She pressed the heel along the base of the flesh and pushed into the lubricant that had accumulated there. And now raised the shoe spike upwards along my well extended length, the sharpness of the concrete damaged heel scratched and marked my rod and sent shivers and electric shocks throughout my very being. I gasped and managed to control my emotions enough to prevent an onslaught of an embarrassing mistimed Orgasm,. Although controlled on this occasion I remained teetering on the edge of a full blown emotional avalanche of pleasure.

Seeing how near I had come to losing control she afforded me a few moments of wanted relaxation, and I used those fleeting moments of reflection to survey were I currently was. Even without Orgasm I still enjoyed the descend from a high plateau to a more controlled level and honestly believed that I was beginning to regain some sort of composure. But she afforded me no more time to consolidate my new position and started once more to heighten the sexual environment that existed between us. As we are in essence the same person she’ll know my little kink about court shoes and heels, she then pressed the uppers against my now desperately leaking muscle and smeared a line of silvery string all along the leather material tops.

With half closed eyes I saw my seeping eye beginning to ooze a little seed now mixed in with the discharge she was coating across the shoe uppers. My testicles appeared tight and felt as if they were pulsing inside there little protective sac, and I was acutely aware that I was only seconds away from an Orgasm that would have broken all my personal records. I now resigned myself to ejaculating across the front of those darling little black court shoes.

Suddenly the shoe dropped away to the side of the bed, I looked towards her and I guess she must have seen the look of shock on my face, was she not going to release my pent up inner fire? Or just leave me to smoulder until I went cold. She answered almost immediately as Carolyn lowered those aubergine coloured lips and grasped my now swaying member tightly between them. In all this time we had spent building up to this moment, hardly had she touched me in that kind of way. My state of arousal was purely due to anticipation of this coming event. But now a physical contact was all that was required to push me beyond what I could consider a safe return. I felt the pressure and the warmth of her mouth clamp around me and closed my eyes as I savoured this incredible feeling of power over you.

I dragged them open again to see her lips now ascending upwards towards the weeping slit. But I guess what finished me off was seeing her aubergine lipstick smearing its self with a streak of colour along my fully inflated cock! Resistance was no longer my concern as I was completely broken at this point, and was shocked to feel tears running down my eyes as the moment over whelmed me. Endorphins flooded my head as I gasped for breath and forced myself to look through the tear stained eyes at the action that was taking place below. My whole hips seem to buckle and my bottom forced its way skywards, forcing my now gushing cock to eject its first spasm of white hot seed straight between those aubergine lips. Carolyn released her mouth suddenly, but continued to hold me between her teeth, this allowed my first spent fruit to return a second later or so later, and then dribble down the shaft blurring, the lipstick deposits that she left earlier. I thrusted up for a second time trying to engage as much of my ejecting penis that I could insert into her but she controlled my penetration by drawing way from me, quite possibly for her own safety I expect. I guess I must have thrashed about a bit as the effect of this super Orgasm took control of my very being. Nothing in the world to me mattered anymore! than to experience this, as I rode out this sexual release that was being performed on my elderly body. Never since my youth have I ever seemingly produced such a volume seminal fluid that was now passing between myself and my alta ego.

Almost a white out as the avalanche of pleasure that was being allowed to fall from her mouth as she manipulated my emotions, never once did Carolyn attempt to swallow any of my hot milk but teased my very vision by giving me the pleasure of fully seeing what was being performed for my immediate benefit. My body tensed and then relaxed in a rhythmic fashion as my backside raised and lowered its self in tune with my ejaculations. All of my body seemed to become one as the effects of cumin seemed to spread to every extremity. My toes curled up as did my finger caress her face and try and control her movements. Funny enough an old joke about a vicar holding his liquor suddenly flashed through my mind. My breath was ragged and seemed uncontrolled as the effects of being in Orgasm robs you of you co-ordination.

A few moments later and now on the downside as my ability to continue began to fade, my breath kind of normalised and my thrusts became less. Then another second or two I allowed my arse to fall back on the bed for the last time. Looking up I saw Carolyn with her mouth still open and mused that my cock had been there only moments before. I started to enter that after glow phase of sex and enjoyed the relaxed feeling that it brings. This allowed me a little time to survey the situation. Those aubergine lips that were so perfect at the start of our little tryst was now showing signs of the aggressive encounter they had with my fully charged phallus, hardly any stood the onslaught but a few traces at the corners.
Not that it worried Carolyn of course and she smiled a little pushing a little pool of my cum that had accumulated at the bottom of her mouth...



I couldn't describe myself as being rampant anymore as the deflation had well and truly set in but I continued to observe my state. The heat of those fruits were now beginning to cool enough to be a little uncomfortable, but afterglow effects allowed me to live with that at for the moment. But I was aware that a big clean up was due very soon and wondered why I hadn't previously sorted out some tissue or wetwipes. My cock was displaying that tell tail sign of aching a little from the stretching that it undoubtedly underwent over the last period leading up to this moment. Although my breath wasn't so tortuous as it had been a little while ago, I was still trying to regain the oxygen that was so depleted during that sexual encounter with my mind. Sexually I was for the moment satisfied and didn't have any immediate desire to cum again for a little while.

Was it a little guilt now that no doubt haunts many crossdressers at this point, here I am a man to all intents and purposes. But my current image betrays what I currently am. The palms of my hands caress down the beautiful A line dress and folds back to temporally cover my soiled knickers that resides beneath them. I notice the little silver bracelet that dangles from my wrist and feel the cold material of the necklace as the cooling air circulates my open neckline. Nina Ricci perfume still hangs in the air and continues to tease my senses to distraction. My tights are stained and wet with a chalky looking substance that seems to have deposited its self in more places than I could possibly see at this moment in time. These clothes I am thinking are on there way to the laundry basket before I can wear them again. One little court shoe on my foot and the other half swinging from my toes as it became dislodged the moment I first experienced the climatical throes of Orgasm that invaded my body not so long ago. I spent the next fifteen minutes or so cleaning up the bedroom and packing Carolyn away so her existence is not betrayed to others who need not know about the closeness of our intimate relationship..