My heart raced much faster than usual as I nervously approached the uninspiring front door of this nondescript house in suburbia. After having booked my appointment several weeks earlier the countdown was finally over. I casually checked my watch, I was asked to arrive at 9am - not a minute earlier and later. Being a punctual person myself, I appreciated the accuracy of the appointment scheduling.
I press the doorbell and instantaneously hear a dulled chime emanating from within the building. As long as a minute passes before I hear movement inside, and seconds after a wooden door behind a mesh security screen begins to open. I am asked my name and then welcomed inside by my host as she unlocks the security mesh door to allow me entry.
"Lovely to meet you Michael, I'm Alison", she says as we gently shake hands.
Alison is slightly shorter than myself and her body shape one of an athlete. She had shortish dark brown hair that fell to just below her shoulders. She wore a flowing black gown which beautifully contrasted with her pale, white skin. While she wore minimal makeup, her eyes in particular drew me in immediately, a faint trace of black eyeliner maximising her eyes' impact. She wore a single pair of gold ball studs in her earlobes which matched a small stud in the left side of nose. Her fingernails were quite long and painted a striking bright red colour. Black, designer style high heels exposed brightly painted red toenails to complete her look. It would be a gross understatement to say that she was attractive, she could easily grace the pages of any fashion magazine.
"I've really been looking forward to our session", she continued sensing my nervousness, "just relax darling, you're in a very safe place. There are no secrets here. You can be whoever you want to be as there will be no judgment".
I too had been counting the days since I first contacted Alison via her website. A website that I'd explored extensively in the preceding weeks prior to building up the courage to take the next step and request an appointment. In excess of 20 emails had travelled between us since my booking. Me asking questions and expressing my concerns for what would occur during our session and Alison replying to reassure me that everything was fine. I booked in for an hour long sensual massage, not yet having the courage to reveal the full extent of my fantasies.
"Now, when you're ready, please follow me through the treatment room", Alison requested.
Any initial trepidation passed as soon as I was in Alison's presence. She exuded an air of confidence and acceptance that was contagious.
I followed her into a smaller room which was quite dimly lit. The wall directly ahead was quite bare with the exception of three largish framed paintings of naked and semi-naked people of such quality that they could easily have been on display in a gallery of fine art. There was a large closed ceiling height cupboard to the left end of the room and a small, covered window at the other end. A small bench below the window held a selection of various size candles, many of which were alight. A large towel covered bench style table dominated the centre of the room.
"Now, please strip down to just your underpants if you're comfortable with that and I'll be back shortly so we can begin. Stand at the end of the table when you are ready, facing away from the door", she instructed as she slipped passed me closing the door behind her.
I did as asked, stacking neatly my excess clothing on a smallish chair in a corner of the room before taking my place as requested. Strangely I felt very calm about my surroundings, my heart rate not speeding as it had when I approached Alison's house.
My mind though was feverishly trying to take everything in. All on my senses were heightened as my brain tried to absorb the smells of the scented candles, the imagery of the three paintings and even feeling the long pile carpet between my toes.
It was probably ten minutes before a gentle knock on the door signalled that Alison had joined me.
"Please do not turn around Michael, I'm just going to place a blindfold over your eyes if that is okay?", she questioned. My lack of reply she took as acceptance of her wish.
After placing the blindfold over my eyes from behind me, she gave me some final instructions. While delivering her instruction I could feel her long, sharpened fingernails tracing down my back and slightly in underneath my underpants. I felt immediately under Alison's control.
"As planned you are about experience a full body massage with perhaps some light BDSM influences. If during our session you do not feel safe or comfortable with what I'm doing in any way, please let me know. I want you to surrender yourself to me as this will allow me to take you well beyond your comfort zone. Do you understand?".
"Do you understand!", she repeated in a far harsher tone than she had used previously upon me not answering promptly.
I tried to apologise for the tardiness of my response but a firm stroke from her hand across my right buttock showed that it wasn't accepted. While initially shocked that she had struck me, my physical response was not of pain but pleasure.
"Now pull those underpants down immediately, you won't be needing those anymore. I want to see my hand mark that I've just left on you".
I removed my underpants as requested and was then asked to stretch my arms out in front of me which I did promptly, instinctively not wishing to be spanked again. I heard her open the cupboard and a slight sound as she removed something from within. She then took my left arm and began attaching something around my wrist. Once done the same was repeated on the right hand side as well. I was instructed to put my arms by my side and then heard her getting something else from the cupboard. Shortly after, similar devices were placed around my ankles.
"Would you like to see what I've done to you?", she questioned.
I replied immediately in the affirmative and she removed my blindfold. Rather than look instantly at what I would later discover to be ankle and wrist restraints, I was immediately drawn to Alison's body directly in front of me taking no interest whatsoever in my new attachments.
Gone was the gown that had previously covered most of Alison’s body. She was now wearing a small, black lacy bra that struggled to contain her ample breasts. Matching slim, bikini style underwear sparingly covered her curvy groin. She had tied her hair back and her ears were now adorned with a pair of large silver hoop earrings, about two inches in diameter, which swung gracefully from her lobes. The gold balls that were previously her only earrings, now placed in a second hole on each side. I think I noticed more holes in her ears too but I couldn't be sure.
Alison’s eye makeup was now also much more prominent with darker tones used above and below her eyes giving them a strong smokey look. Thicker, dark eyeliner now further framed her striking eyes. Her lips were coated bright red matching her nails. Glancing down for a second look I saw that she had a diamond encrusted bar pierced through her navel which instantly aroused my interest. Her pierced belly button looked perfect, so feminine and sexy. From head to toe, she was stunning and my manliness had promptly reacted accordingly.
Alison noticed that I was particularly aroused and slapped me on the hip firmly but seductively. As before, this brought me nothing but pleasure.
"I'm glad you approve", she said egotistically, "now climb onto the table with your head at the far end facing upwards".
Once in position, the blindfold was returned and I was asked to place my hands palm down beside my torso. Alison then fastened my ankles securely to the respective corners of the table which spread my legs reasonably wide apart. Each of my fingers were then splayed by some type of frame on each side with my wrists then very firmly tied to the table. As a final step, headphones playing indiscernible music, were placed over my ears but not before Alison explained that they were to block out any external noise so that I could solely focus my thoughts on her attention. While now completely immobilised, I felt no fear whatsoever and eagerly awaited whatever was to come next.
Now effectively deaf and blind my other senses were on high alert. I then felt both of Alison's oiled hands begin to massage my lower legs moving back and forwards, creeping ever so slowly further upwards with each movement. I was already in a state of ecstasy when she reached the upper sections of my legs. Her attention to the inner parts of my thighs particularly feeling amazing. Just when I thought that she was about the handle my firm, aroused penis she stopped and I felt no touch anywhere for what felt like a good five minutes.
My previously erect penis was now flaccid and I was beginning to question what Alison was doing when I felt her magical hands begin to massage my shoulders from where she was standing at the head of the table. Seductively she moved her attention in lengthening strokes across my shoulders, chest and stomach and stretching all the way down to my hips. On the extent of her reach, her breasts rubbed deliberately and enticingly against my face. Again, just as I felt that she was about to begin massaging my penis and scrotum she stopped. She was teasing me to the very limit of my control and I couldn't wait for her to take me over the edge.
The music ceasing and Alison removing the headphones signified that the next phase of our session was about to commence.
"I see that you quite enjoy being massaged", she said confidently, again basking in recognition of her own skills.
I responded saying that it felt amazing.
"Amazing? If you think that me simply massaging you and rubbing my tits in your face occasionally was amazing, you've got no idea of what other plans I have for you", she continued.
With her last statement, my brain went into overdrive and I honestly had no idea of what she had in mind for me. She was undoubtedly now fully in control of my fate and I gladly submitted to her wishes.
She then unshackled my wrists which had been constricted for some time and felt quite stiff, needing me to move them around to regain some dexterity. My ankle restraints though were kept firmly in place. I wasn't free of the table yet, not that I wanted to be.
I was then instructed and assisted to sit upright. Alison asked me to place my hands out in front of me which I did quickly despite not knowing what to expect.
"I hope you like them!" Alison announced as she swiftly removed my blindfold.
Through slightly disoriented eyes, given that my eyes had been in complete darkness for quite a while, I looked down at my now trembling hands. Each of my ten fingernails was now painted bright red, matching Alison's own nail colour exactly.
"What . . what . . why ?" I bumbled out still trying to come to terms with the unnatural sight before me.
"Now tell me honestly?", Alison responded excitedly, "don't you just love them!".
I had to admit that deep down I was absolutely thrilled to see my own hands with painted nails but acknowledging this to Alison would be letting down my guard. A barrier to my own desires that I had vigorously maintained for most of my life.
"Tell me now that you don't love them and I'll remove the polish immediately", continued Alison, "or let yourself tell the truth about what you've been hiding and let me help you".
Without hesitation I replied "I love them", and with that my self-defence mechanism was removed.
"How did you know that I'd want my nails painted?" I queried Alison, "when did you even paint them?".
"When I paused the massage for a short while after doing your legs, I was discretely painting your nails hoping that you didn't feeling anything", she responded.
"Well you were very stealthy as I didn't feel my nails being painted at all", I replied, "but in my defence, my mind was still in a spin from your massage".
At this, we both shared a laugh while I continued to be transfixed at my beautifully painted nails that were by the minute becoming more natural to me.
"I know quite a lot about you actually. What you like, what you desire, your fantasies. It's incredible what you can uncover about a person from looking through their internet browsing history", she said nonchalantly.
"But how did you get access to what I've been browsing online?", I replied with a slight tinge of trepidation.
Alison went on to explain that prior to her current line of work she was a cyber security expert, working predominately freelance and hired by large finance companies to help them remain secure against online attacks. While she continued to do some cyber security consulting because it paid so well, it was just a job and what she was doing more of now was her real passion. I couldn't disagree with her on that point - she is definitely very passionate and skilled in her current career choice given my dealings with her so far today.
To access my browsing history, and while not exactly sure of the technical dealings, Alison had discovered my computer's IP address from my emails to her and then cross checked this to IP addresses of people accessing her website. Given that this showed that I was clearly highly interested in her services due to my frequent visits to her site, she investigated me further. With her skillset it wasn't long before she'd infiltrated my computer's minimal security and had full access to all of my deepest held secrets.
"I noticed that you searched and looked at multiple sites covering crossdressing, male-to-female transformations and videos of predominately women receiving various beauty treatments in salons. Even a few more serious sites that I'd classify as forced feminization", Alison outlined.
"Don't be embarrassed Michael", she said comfortingly, "as I said that the very start of our session, there is no judgment. I just want to help you discover some of your feminine side in a safe environment. With me you are free to explore your sexuality and experience some of what it's like to be a woman. Isn’t that what you’ve always wanted?".
At Alison's last statement I lost control of my emotions and began sobbing openly, the weight of so many years of maintaining my outward persona not necessary in Alison's company. She hugged me for several minutes whispering reassuring words to me saying that she'd love to help me further explore my inner woman.
"So Alison, what do you have planned for me now? You're such an accepting person and I trust you explicitly, you can do whatever you like to me", I asked, once I had composed myself more or less.
"How would you like me to give you some basic makeup to see what that's like," she replied, "I noticed that you've viewed quite a few videos of ladies getting their makeup done professionally. While I’m not claiming to be an expert makeup artist, I think you'd love to experience having some makeup applied".
Naturally, I instantly agreed with her suggestion eager to try wearing makeup. Alison then removed my legs from their bindings and I climbed down from the table. She excused herself before leaving the room to gather some makeup materials. The realisation that one of my lifelong fantasies was now occurring was very powerful and I almost needed to figuratively pinch myself to ensure that I wasn't dreaming. Seeing and feeling my new nails made me well aware that they were definitely real and also the fact that I was soon at have some makeup applied which is something that I'd yearned for over the years. The fact that it was to be done by a gorgeous, spontaneous woman who supported me in my desires made what I was experiencing even more precious.
"Okay Michael, if you can sit at the end of the table I think it will be the best", Alison announced returning to the room with both hands full of assorted beauty products.
I did so as excitedly as any young girl whose mother had just offered to do her makeup for the first time.
"Now, I don't want to go over the top the first time you're having this done", Alison further explained, "just enough for you to experience having it done and hopefully we see some change in your appearance too".
"Now I should do some foundation first to make your skin tones even but there's so much else that I want to do with you today that it will just have to be skipped", she continued, "I think just some eyeshadow, eyeliner, mascara and lipstick and perhaps some work on your brows will be plenty for today".
While many of the items just outlined by Alison would have been foreign terms to most men, to me with my particular alternative interests, I knew exactly what each was and what was involved. Until now my understanding of makeup had purely been theoretical but as Alison asked me to close my eyes and I felt her gently brushing on some eyeshadow, the practical element had commenced and I was thrilled. I kept my eyes closed while she went about her work and loved the sensation of feeling Alison brushing on the eyeshadow, intermittently pausing to smudge her work with a finger or simply view her progress. Eyeshadow done, next she asked me to open my eyes and I saw her pick up a small container of black gel eyeliner and a fine tipped brush.
I couldn't help but look at her own perfectly traced, thick eyeliner and hope that my eyes too would soon vaguely resemble hers. I was asked to close my eyelids again and could feel the eyeliner being applied to firstly my upper lash line, Alison slightly overlapping each stroke to ensure that nothing was missed. Upper lid complete, I needed to open my eyes as she repeated the process below each eye.
"That's coming along wonderfully Michael, you're going to love how your eyes now look," she explained, me now very curious to see my altered appearance.
"Actually it's not screaming sexy to me and surely you would like to look sexy rather than just normal!" she exhorted, picking up the eyeliner and fine tipped brush to continue my soon to be sexier eyeliner before I could even agree with her statement.
As directed by Alison, I was soon looking in various directions as she applied more eyeliner, especially to the inner rims of my eyelids and right into the very corners of my eyes. It is quite confronting the first time someone has an implement so close to your eyeball and not to shy away. After a few initial nerves, I quite enjoyed the having the eyeliner applied extensively to my lash line. I hoped that my eyes were now sexy as Alison desired and this was soon confirmed when she announced that it was indeed the look that she was attempting to achieve. Mascara came next with Alison having me again looking in all sort of places in the room. I had regularly marvelled at long, dark eyelashes on women and relished having my own lashes being slightly tugged, coated and lengthened with darkening liquid.
"Your eyes look amazing Michael", Alison announced signalling that my eye makeup was now complete, "they're even better than I expected”.
Her analysis of my eyes only made me want to see myself more but I knew that asking was not appropriate and I would be shown when Alison deemed it necessary. A dark brown eyebrow pencil was then used to fill in and accentuate the shape and thickness of my brows. Finally she used a small pencil to first outline my lips which she said needed to be better defined, before coating my lips in a striking red colour, no doubt the same shade that she was wearing herself.
My makeup for the day complete, Alison retrieved a smallish mirror, about the dimensions of a magazine, from the cupboard and brought it towards me. While most of me couldn't wait to see my new appearance, a small part of me suddenly sensed fear. What if when I see myself I look ridiculous and like a four year who had gotten into her mother's makeup? What if my years spent dreaming about how wonderful I'd look like female was shattered with a single glance? What if Alison had been lying and I was really nothing more than a freak wearing makeup?
As I first caught a glance at my made up face, my fears instantly disappeared. I had to take a second look to actually realise that the face reflected in the mirror was me. While earlier seeing my painted nails for the first time was unnatural, my beautifully applied makeup was surreal. My previously pale eyebrows now were much darker and more defined with an unmistakable feminine arch, tapering down towards the outside ends. My bright red lips looked so much fuller and prominent than before but the undoubted highlight were my eyes that I would best describe with the word smouldering. While not exactly the same as Alison's own gorgeous eyes, my eyes now were without question sexy.
"Thank you so much Alison, I'm lost for words", I mumbled.
"It's my great pleasure my dear, you look incredible. Your face is actually very feminine in structure and the makeup really highlights this for you", she said, smiling with a satisfied grin on her own beautiful face.
Alison put the makeup to the side and then announced, that she'd like to paint my toenails as well because it would be such a shame if they were to miss out on all of the fun. Alison's statement proved without a doubt that she was having as much, if not more, fun than I was and this was no small feat given my own thrilling experiences so far. Within a few minutes my toenails were now painted the lovely, vibrant red colour that we both shared. I watched intently as Alison carefully painted my toenails, each separated slightly by a tissue woven between my toes. Alison started with a long stroke commencing at the base in the centre of each nail which then flowed in one fluid motion to the tip. Each side was then completed with a similar technique. Watching having my nails painted was something that I’d long desired and now that it had happened it felt even better than I could have imagined.
"Would you considering me adding a couple more things to make you feel more feminine?", queried Alison as she placed away the nail polish bottle.
For not the first time that day my mind went into a spin at Alison's latest invitation to step further into the feminine world. A world that until today, had been purely an unobtainable dream. I considered some possibilities that Alison could have in mind for me next. I'd looked at such a broad variety of alternative websites that I couldn't be confident of choosing anything. I considered perhaps she might want to wax me, definitely an avenue for pleasure and pain there. Some feminine clothing? Get me to wear some dresses and perhaps high heeled shoes. I'd also been viewing quite a few YouTube clips involving piercings which I had become increasingly interested in during recent months. Could that what she was about to suggest? Given that she had quite a few piercings herself, this last thought was a real possibility. While the idea of being pierced was enticing, the permanency of piercings plus my fear of the pain factor brought me some internal distress.
"Would you like to try wearing a bra and also a wig to feel more girly?", Alison suggested, allaying my fears.
With a slight sense of relief I accepted her invitation. Alison pardoned herself, leaving the room to presumably source a wig and bra. I took the opportunity while alone to again glance in the mirror at my lovely makeup. The reflected image made all the more special when I noticed that the hand holding the mirror had beautifully painted nails. I also delighted in looking down to see my special toes - oh want a day I was having thanks to Alison.
I was soon brought back from fantasy land when Alison returned to the room. I replaced the mirror and stood by the table keenly awaiting Alison's next instructions. She had me turn and face away from her and next felt her reaching around in front of my chest with the bra. Looking down the bra was black like her own but much fuller in material compared to her own minimal design. Regardless, I loved it immediately.
"Now hopefully this will fit you," Alison said, "it's an older bra of mine that I used to wear before I lost some weight".
I hadn't for a second considered that Alison's body had ever been anything other than the lean physique that she now possessed. My bra, with quite a bit of stretching and me breathing in, was eventually fastened at the back. Alison had me spin around to check the front and make some finer adjustments. I loved feeling the straps holding me tightly in position.
"To fill the bra I've only got some socks that I'll roll up", she stated, beginning to stuff the basically empty cups of my bra.
"Next time I'd like to get you some silicon breast forms that will move and act much more naturally", she continued.
Alison's use of the words "next time" thrilled me as for the first time I considered that today’s visit potentially more than a one-off experience. The thought of an ongoing relationship with Alison where I could further spend time in, and explore further, the feminine world was very heartwarming.
My sock breasts now in place, Alison encouraged me to feel them. I must admit that they felt incredible. Firstly to feel weight and something firmly secured to my chest and also the sensation of my hands holding them. Alison then slipped around behind me and reaching up my sides also cupped my breasts in her hands to check that everything felt right. Her pulling me back forcefully against her until our bodies were tightly against each other made me feel very safe and so assured that what we were doing together was right.
Breasts inspected, it wasn't long until Alison had my wig in place. She had a selection of three to choose from - a short blonde bob style, a longish chocolate brown wavy one and a black shoulder length straightened hair option. We unanimously agreed that the longish chocolate brown wavy wig was the one that I should wear. Once in place, I couldn't believe how it felt to have long hair against my face and down the back of my neck, it felt amazing. Alison took quite a while adjusting my wig until it was just as she wanted.
“There you are Michael”, Alison said acknowledging that she was satisfied with my wig, “you look so different. I’ll grab the mirror so you can see for yourself”.
I was shocked when I got to see myself. Long wavy brown hair cascaded down to around half way down my back. Alison had draped some hair down the front as well and this rested over my black brasserie. My gorgeous wig coupled with the makeup made me unrecognisable to the male who had entered Alison’s place earlier that day. If someone didn’t know, they would have sworn that I was a woman. A quite attractive one at that.
“You so should have been born a woman with a your features”, Alison added.
“I can’t believe how just a little makeup and that wig have transformed how you look so dramatically. Breasts really suit you too and give you a much more sensual, curvy figure. You are so pretty and there’s so much more we can do another time as well to make you even more attractive”, she continued.
I too was blown away at how I now looked and Alison’s reference again to further girl time. I felt like I was hallucinating such was the change in my appearance and I literally had to open and close my eyes one at a time and wiggle my mouth to try to comprehend that the beautiful image I was viewing was actually me. For my whole life my eyes had seen nothing but a male figure and now it was so, so different. I was spellbound and unconsciously started to fondle my own breasts and become aroused by what I was seeing and feeling. I think Alison noticed that I was becoming a little sidetracked and her starting to speak brought me back from my daydreaming.
"It’s so pleasing to see you so totally engrossed in your new self but you were originally here for a sensual massage and I've not really even started that”.
Unbeknownst to me, my appointment was about to be taken to a whole new level.
“Time to awaken your feminine inside now Michaela”, Alison announced, “I’ve done some superficial things to your outward appearance but now I want to take your mind and body on a much more meaningful journey”.
Did I hear that right I asked myself? Michaela???
“Yes, I’ve decided that you will now be called Michaela. Such a pretty name for an attractive lady”, Alison instructed recognising that I picked up on her new name for me, “there is no way that someone who looks like you do now would be called Michael”.
Alison started by having Michaela perform a strip tease. I had to strut around erotically to pleasure her, each instruction preceded with Michaela.
“Michaela, show me those sexy legs”.
“Michaela, walk around and show off your gorgeous, sexy body”.
Quickly I changed back into much more a subservient role following Alison’s every command to the letter. I really loved submitting to her will and, while illogical in many ways, the sense of freedom that being dominated created for me.
Once my strip tease was completed to Alison’s satisfaction she took the blindfold again and placed it over my eyes. Funnily, my first reaction was that the blindfold would smudge my beautiful makeup. I was well and truly zoning into the new me.
“Please stand perfectly still”, Alison ordered, definitely now more in dominatrix mode than the girlfriend persona she took when she was applying my makeup.
I heard her slide open a cupboard draw and start rummaging through it to find whatever she was after. Searching complete, I now sensed her very close to me again.
“Hold you head very still Michaela, I need to get this just right,” she instructed.
I had no idea what to expect but then felt her attaching something to my left earlobe and a slight pinching sensation. I instantly thought that she’d pierced my ear confirming my earlier thoughts although there was no real sting as I would have expected. A short pause, and after hearing Alison walk behind me, the same pinch happened on my right earlobe. Realising that my ears hadn’t been pierced, it then dawned on me that she had maybe placed small forceps on my lobes like I’d seen occur numerous times on YouTube when people had their lobes pierced with a hollow needle. I was about to have my ears pierced!
I then sensed Alison move behind me and simultaneously felt a firm tugging on each earlobe. A wonderful sensation repeated as she continued to sporadically pull on the chain. My already aroused penis twitching with each movement.
“I’ve attached clamps to both of your earlobes and they are joined by a chain. I’d usually use these on someone’s nipples but seeing yours are covered by your bra I thought of another use for them”, she explained, deflating my psyching myself up thinking Alison was about to pierce my ears.
“Our ears are such an erogenous zone on our bodies”, she continued, “it would be a shame to waste them”.
While Alison continued to tug on the chain with one hand her other hand began to wander over my body in undefined patterns. Her long, talon-like nails regularly scratching my naked flesh more and more aggressively. Her moving hand’s attention and the simulation to my ears was blissful but I must admit that I was a little disappointed that Alison hadn’t chosen to pierce my ears; at least not yet.
Restraints were then placed around my ankles before I was asked to get onto the table. Alison ordered me to be on my hands and knees which I did hesitantly given I was not able to see.
“I’m just placing a rolled towel across the table between your hands and feet”, Alison instructed, “it will help stop your clitty getting too excited”.
I no longer had a penis it appeared, another aspect of my maleness transformed.
Alison then asked me to slowly move down and lay face down on the table. As I began to descend I felt one of her hands reach between my legs from behind which startled me a little. Effortlessly, her hand pushed both of my testicles from my scrotum and up inside my body. Her other hand then reached through and firmly pulled my semi-erect “clitoris” back and upwards. By the time my torso had reached the table’s surface, my rearranged genitalia and the placement of the rolled towel, well and truly prevented me from being overly aroused.
I also received another first time sensation when my no longer flat chest was pressed against the padded table. While a little disconcerting initially, it was really nothing when compared with what transpired a little further down my body. This was certainly turning out to be a long series of experiences that I would never wish to forget. My hands were then handcuffed and the handcuffs tied loosely to the head of the table. My leg restraints were then bound to the corner of the table again exposing the lower half of my body.
Alison’s domination and my vulnerability had reached new extremes. I felt as helpless as I’d ever been in my life but paradoxically so safe at the same time. Alison then began to massage and tease me with her hands, moving rhythmically across my body, as I sank deeper into female territory, her whispers taking me further into my subconscious than ever before. Occasionally she would tug on the chain linking the clamps on my earlobes sending a burst of stimulation to another part of my body. My feminine brain and every inch of my female body were being slowly awakened and I loved it!
Alison had definitely researched my internet browsing history extensively as she mentioned so many of the topics that I’d searched while fantasising about what was now happening to me.
“You’re a stunning, beautiful woman. You deserve to feel how you would want to feel. Let the little girl inside you be free”, sensually Alison repeated as I consciously gave myself permission to let go and let my femininity come out to play.
This relaxation was then interrupted, as out of nowhere Alison began to spank my bottom, first with her bare hand, and soon after with what I was later to discover being a small, thin whip.
“You’re a naughty little girl Michaela”, Alison barked derogatively, “tell me what you are?!”.
“I’m a naughty little girl”, I mumbled hesitantly.
“Louder Michaela!”, she ordered, a hand spanking me across my backside harder than previously.
“I’m a naughty little girl!”, I blurted out as the sting of the whip on my exposed buttocks indicated that Alison approved of my second attempt.
“That’s better, now I don’t want to hear another word from you until I’ve finished with you!”, she demanded taking full control of my destiny.
There was no fixed pattern as Alison metered out my punishment and this only heightening the sense of impending pleasure as I waited for the wicked sting associated with her whip strokes or bare hand, both being delivered with ever increasing intensity. I was after all being a very bad man for dabbling in women’s ways and therefore deserved to be punished. After a while she paused whipping and spanking my buttocks and upper legs briefly as if not wanting to push me to far. I was still well away from my pain threshold and unconsciously raised my stinging hind parts like an offering to her to which she thanked me and obligingly continued to sting my bare flesh with renewed vigour. It was magnificent and I thoroughly enjoyed how Alison dealt with my sins.
The sound of the whip crashing against a wall ended my punishment. At this point, I was quite exhausted, both mentally and physically and struggling to regain my breath. A breath somewhat restricted by the tightness of my bra. Not that I would have wanted it removed, even during my punishment I loved feeling my pretend breasts being forced against my chest by the table.
“You did very well there young lady”, Alison said slightly out of breath herself, “Mistress Alison is very impressed with your resilience. You have proven to be quite the surprise Michaela”.
After a few moments Alison removed my ankle restraints, unlocked the handcuffs. She also removed the clamps from my ears sending a surge of blood to my earlobes causing them to throb for a minute or so. We both took the opportunity to catch our respective breaths. Alison then informed me that she was placing on a pair of surgical gloves, the significance of which did not register to me at the time. Still lying on my front, Alison commenced massaging my legs and still very tender buttocks. This was again very relaxing, as she regularly rubbed me in all the right places. I was being gradually aroused, and this only increased with every passing stroke of her hands and hearing little messages she whispered to me from time to time.
With one hand, she massaged my back and with the other she began running her gloved fingers erotically along my arse crack. This hand never straying far from my anus, that was now yearning to be entered. With each hand movement, my desire to have her penetrate me only grew deeper.
“I am going to take your virginity now Michaela, time for the little girl inside you to become a woman”, she announced boldly, both of us knowing explicitly that her proposal was consensual.
Like earlier, my hips rose intuitively in anticipation. I was on a knife’s edge when I felt one of her fingers start to slowly move inside of me. It was so fulfilling to welcome her into my body and the pleasure only increased as she continued further and further inside. Soon what felt like an addition finger or even two more were also working their way in and out of me in a distinct rhythm. With each movement of Alison’s arm, my body reacted and thrust in the opposite direction. She was now massaging my prostate and I don’t have sufficient words to do justice to the wondrous experience that was occurring throughout my entire body. The intensity continued to build and there wasn’t a point where the sensation diminished. I was on the brink of cumming, when I felt her begin to extract my newly found friends from deep inside of me.
Alison was far from finished with me though. She asked me to turn onto my back. Our session was about to be taken to another level. I then felt her also climb onto the table to join me, her sitting at the end of the table and placing one of my legs to each side of her, our thighs now rubbing together.
With her right hand, she effortlessly re-entered me, while her left hand, started stroking my now unrestricted and already heavily engorged clitoris. The dual stimulation was so incredible, that it was impossible tell which hand was providing the greater pleasure. This attention went on for what seemed like forever, but was probably five minutes. Just when I felt, like to couldn’t hold myself back from exploding any longer, Alison’s intensity only increased, our bodies rocking as one to the point where it was surprising that the table legs hadn’t given way. She was simulating my entire body, which I can only describe as being electrocuted from the inside out.
Alison then stopped all movement and requested that I remove my blindfold which I did with trembling hands. My faculties vaguely returning, it was then that I noticed that Alison had removed her bra, presumably around the time when I was blindfolded. Like everything else about her, her large firm breasts were magnificent and my last essence of manliness caused my raging hard-on to spasm intensely but amazingly not cum.
“What you are are about to experience Michaela is a full body orgasm, one drawn from deep inside you and not purely instigated by your genitals”, Alison stated, now appearing far more in girlfriend mode.
“Cup your breasts with your hands and just let your body react instinctively”, she continued.
As instructed, I cupped my breasts which now felt very much part of me and looked down towards Alison. The vision of my red painted nails holding my breasts combined with the presence of a beautiful, now naked, woman between my thighs was indescribable. Just as I thought that I couldn’t be pleasured further, Alison starting moving her hands again as well as gyrating her body causing me to reciprocate. Her hand inside me began increasing in intensity and frequency and the corresponding energy was replicated on her other hand sliding up and down my shaft.
I was now at a place, where I had no physical control of my body, or even a sense where I was, or who I was for that matter. The full body orgasm that I then experienced had my body quivering and shaking uncontrollably. My best attempt to describe the feeling was the combined force of every ejaculation that I’d ever had occurring simultaneously yet I knew that I was yet to cum. This went on for several minutes, the single most powerful experience of my life.
Alison then encouraged me to “let it go” and with her command I came like never before, exploding at least a dozen times, and with such pressure that cum flew well over my delirious head. A volcano had erupted inside of me, and I was tingling from head to toe for the next few minutes. I honestly don’t know what happened for the next little while, other than hearing the soothing voice of Alison guiding me gently back to reality.
Now back on earth, Alison and I remained on the table and chatted reviewing what had just occurred. It was, undoubtedly, the most amazing experience that I have ever experienced. Nothing else in my life, has even come close to the seemingly boundless exotic pleasures on which I feasted during this most incredible session. Alison herself also commented that it was definitely the most intense and rewarding appointment that she’d ever been involved with since starting her business.
Our time together drawing to a close, Alison assisted me in removing my wig and bra, both of which I’d grown quite fond of wearing. She then gathered her black robe and put in on, not concerned with the necessity for either a bra or underpants. Next, nail polish remover made light work of my beautiful painted nails on my fingers but just before she was about to remove my toenail paint she offered an alternative.
“You live alone right?” she queried, to which I replied in the affirmative.
“Well there’s no reason that we need to remove the paint from your toenails is there?”, Alison suggested, “it can be a little keepsake from Mistress Alison to remind you of Michaela”.
I loved the idea of Alison’s unique souvenir. Painted fingernails would have been so obvious on a male, especially ones painted in the brightest of red, but being winter my toes would be safely hidden away whenever in public. I was directed to a bathroom and had one last look in the vanity mirror at the remnants of Michaela, my exquisite makeup still looking amazing despite some of it having been rubbed off due to the blindfold. I also inspected my backside that was still very red and showing distinct thin lines courtesy of the whip during my earlier punishment.
Once in the shower I spent the next five minutes or so trying my best to remove the makeup and also the sweat residue that had built up due to our quite physical interaction. All the while contentedly looking down at my gorgeous red toenails seemingly dancing in the cascading water in the base of the shower. Shower complete, I dried myself taking it particularly carefully on my buttocks. Wrapping the towel around myself I returned to our special room.
“Let me have a look at you Michael”, Alison said completely back in what I’d regard as girlfriend mode.
“All the lipstick and eyeshadow are definitely gone, but there’s still some eyeliner I can see and maybe your eyebrows are a little darker as the eyebrow pencil contains some colouring agents that can slightly dye your eyebrows”, she continued.
“I thought the eyeliner might not want to come off so while you were showering I got some of my own specialised makeup remover. Come over here and see if I can get the last of it for you” she requested.
Though deep down I didn’t want to lose the last hint of Michaela’s makeup, I also knew that the eyeliner would immediately draw attention beyond the safety of Alison’s place. Immediately my defensive walls that had kept Michaela hidden for all of these years needed to come back up. Alison managed to remove most of the eyeliner but enough remained so that when I looked in the small mirror I could still see a small amount. That was fine by me.
Michaela’s time was now over and I began to get dressed. I took it quite slowly, again taking in as much stimulus from my special surroundings as possible. As I put on my socks, I was thrilled that Alison had suggested that I leave my toes painted as I felt like this wasn’t the end of my journey.
Checking my watch as I placed it on my wrist, I realised that I had been in Alison’s company for a little over three hours. In some ways it felt like five minutes while in others it felt like I’d spent a lifetime with Alison. Indeed, it was Michaela’s lifetime.
My initial discussions with Alison regarding payment had us settling on $300 for the hour scheduled session. When I withdrew my wallet from my back pocket I was stopped at once.
“There is no way I’m accepting payment for today”, Alison said firmly, “I’ve had the most wonderful time and it wouldn’t be right to take your money. This is non-negotiable and don’t embarrass me by attempting to offer anything”.
I returned my wallet to my back pocket and simply moved towards Alison before giving her a heartfelt hug. I thanked her again profusely as I started walking from the room with Alison following close behind. As I walked out the entrance door Alison gave me a tender kiss on my cheek.
She was such a contradiction - so sweet and caring, yet able to switch to more dominant roles effortlessly.
“Take care Michael and promise me that you’ll look at your toes often!”, she announced with a cheeky grin on her face.
“I will”, I replied.
I did indeed keep my promise, my toenails remained painted for another fortnight. A previously organised medical appointment finally forced Michaela’s pretty toenails to be removed to protect my secret. I had become so comfortable with seeing them painted that they looked so plain without colour as I sat in the consultation room. Such was my sadness of having to remove my nail polish, that on the drive home from the doctor, I purchased my own small bottle of bright red happiness. Within ten minutes of returning home, Michaela was back.
The day after my most amazing experience I purchased Alison a large pair of diamond studs as a gift. Given that she appeared to like jewellery, I thought it would be something that she would treasure. A very small gesture to thank Alison for her openness, care and of course for unearthing Michaela. I was the least I could do.
As for future visits, Michaela’s very keen. I’m certain that Alison is also keeping track online of what we could do together!
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