With an even mix of nerves and excitement, I arrived at a nondescript grey metal door at the end of a laneway. The 37 labelled on it told me I was in the right place. I was about to meet a BDSM Mistress for the first time. A very experienced and well-reviewed mistress who I had found on the internet and had been corresponding via email for the last three weeks.
The session that I had requested involved many new things for me but revolved around my fetish for pierced ears. I have had an ear piercing fetish since I was a young boy, fascinated by all things concerning having a piece of metal as part of a person’s body. I was always so envious as one by one over the years my female classmates would come to school sporting sparkling studs in their newly pierced earlobes and this interest has never left me.
Over the years I have had my own ear or ears pierced roughly 30 times, all secretly and temporary sadly, as my family and work would not allow me to have permanently pierced ears. My ear piercing fascination has in recent years extended to trying some other traditionally feminine beauty treatments including some waxing, facials and having my nails filed and painted. I have created a female email persona who arranges such treatments with the background being that her husband had lost a bet. Some wonderful times and great laughs have been experienced during these visits to predominately beauty salons.
I had shared these details with Mistress and also that I had a desire to further explore my feminine side on a more sexual level as well during our session together. She promised that she would develop a roleplay that would well and truly cover all of my fantasies and then some.
I knocked on the door and almost immediately was greeted by the strikingly attractive Mistress. While I had extensively explored her website, none of the site’s images did her justice. She was quite imposing in her heels, her eye line being slightly above mine. Being 6’3” myself, it is very rare that I have had to physically look up to a female to maintain eye contact. Her blonde hair was tied back and she was wearing exquisitely applied makeup, especially striking eyeliner and bright red full lips. Her outfit consisted of a black tight fitting latex dress which hugged her figure closely especially around her more than ample breasts. To complete her enthralling appearance were high stiletto heels that gave her the slight height advantage over me.
“Yes, can I help you?” she queried in a casual tone, immediately engaging in role play.
“Oh, yes, I’ve got an appointment to get my ears pierced,” I responded meekly.
“There must have been some type of mistake with your booking,” she replied further confirming to me that she was roleplaying, “this salon has a very strict female-only policy. We don’t treat men here!”.
I was loving our banter and continued to play along with the direction Mistress was leading me responding with, “I wish the lady who took my appointment had told me when I rang to save me traveling right across town to get here. Sorry for wasting your time.”
“You know what we could do?”, Mistress continued with a slightly scheming tone, “If you’re willing, I could dress you as a woman first to get around the silly salon policy that we only treat females and then I’d be able to pierce your ears as you wanted.”
“I’m not sure that’s possible is it?”, I replied back quizzically, “what would being dressed as a woman involve?”.
“Don’t worry about those details, I’ll look after everything,” she added gesturing me to come inside, “it’s going to be fine.”
“Can’t have you missing out on getting those ears pierced can we?!” she added with a wicked grin which made me smile instantly.
Accepting her invitation, I stepped inside even more intrigued as to what plans Mistress had for me. Being my first experience with a BDSM Mistress, leading up to my visit I had read online quite a few articles covering what to expect. One message that I read on several occasions was to just let yourself be immersed in every new experience as if you weren’t curious in the first place, you wouldn’t be where you are right now. Once I stepped inside my mindset immediately shifted to giving myself permission to do what felt right and explore my femininity at a much deeper level than previously. I had also read another Mistress' account regarding preparing for such things the first time and how it was important to feel free to allow yourself to explore without judgment and that the Mistress will have experience in allowing you (me) to explore and embrace each new experience.
Closing and then locking the door behind me, our roleplay was temporarily postponed so I could pay Mistress for her time and she asked if I had any concerns or questions. I replied that I was fine and very keen for her to take full control of our time together. Mistress then requested that I get completely naked indicating a rack on which I could place my clothes.
“I’ll be waiting for you through here when you’re ready,” she said, indicating a long hallway leading into a dimly lit room.
With Mistress now disappeared down the hallway, I began undressing. My heart rate steadily increasing as I contemplated with the removal of each piece of clothing what was waiting for me.
Taking one or two deep breaths, I walked down the hallway and entered a very large open room that had only one source of light. A large arched lamp, which I later discovered to be like ones used by dentists, hung down illuminating a medical style treatment table about halfway along the wall to my left. Noticing really only Mistress’ blonde hair and porcelain skin I walked towards her where she was standing in the centre of the room. In most other circumstances I would have been very embarrassed to be naked in front of anyone but standing in front of Mistress I did not feel any sense of hesitancy.
“Lovely”, she said in a gentle tone, further making me feel very safe in her presence.
With the room being predominantly dark and despite my eyes attempting to gather more information, the only other visual material available was a low bed to Mistress’ left. I recognised a couple of different coloured wigs and bras, some clothing although I wasn’t able to discern what exactly, a few pairs of heeled women’s shoes and several other sundry items that would perhaps be utilised in due course.
“I thought perhaps we’d start your transformation into a woman by applying some makeup so you won’t be recognised,” she instructed, “please lie down on the table with your head here.”
Without hesitation, I followed her gesturing and was soon lying down with my head now rested on a small folded towel directly under the dentist’s style light.
“Now I’m just going to restrain you a little,” she commented, “you’ve come this far and I don’t want you to have the opportunity to change your mind. Please place your arms along your sides and close your eyes.”
I almost needed to close my eyes anyway due to the intensity of the light just above my face and did as instructed with both my arms and eyes. The first restraint, which felt like a thick belt, was placed across my chest. I could then feel Mistress reaching under the medical table and connecting the ends before pulling and securing it tightly. This process was repeated until I was firmly secured by six or seven belts crossing the full length of my body. With my eyes closed, I found great delight in hearing the little clicks and sounds as each belt was removed from its resting place before feeling Mistress further secure me in place. I made minimal attempts to move realising that I could really only move any part of my body a few millimetres.
In something of a shock, I then felt Mistress feeling at my scrotum saying “I was planning to place your male parts in a chastity cage now so they wouldn’t be spotted in the salon. But seeing your cock appears to be very interested in what is happening, I think it’s best we wait!”.
I opened my eyes which struggled to adjust to the intense light before raising my head as far as I could given the restraints. Sure enough, my penis was well and truly erect as Mistress continued with one hand to attempt to extract my testicles that had migrated upwards. In Mistress’ other hand she held a silver metal ribbed chastity cage which reflected in the light. My penis gave an instinctive twitch as soon as I saw it, somehow knowing that this device was to be used on it. While I had seen images online of chastity cages, this was the first time I’d seen one in real life and couldn’t wait to experience having it attached and feeling what it felt like when in place. Given my cock and ball’s current state though, this would have to wait.
With my eyes now focussed, I counted seven separate belts, each about two inches in width, holding me firmly to the table. Hearing some movement behind me, I looked back as best I could as Mistress pushed a wheeled tray table to just beside my face. It contained all manner of makeup signalling that the next phase of our session was about to commence.
“Ok, then my dear,” Mistress said, staying in character, “time to make your face beautiful so that no one will notice that you’re actually a male.”
I simply responded with a passive “Ok”.
Hearing the word “dear” I became aware for the first time Mistress’ use of feminine names and pronouns. Her choice of such gender opposite words than what I was used to hearing would continue throughout our entire session. This further helped shift my mindset from male to very much a female persona making a massive difference in how I would more openly explore each new experience.
“Well it’s not really up to you now I guess anyway given how you’re tied down,” Mistress continued more authoritatively, “I can do pretty well anything I’d like to you. I think makeup to match mine would be appropriate don’t you think?”.
“I guess so,” I replied, knowing that I didn’t really have any choice.
Upon looking more closely at Mistress’ face and her exquisite makeup, the truth was, I couldn’t wait to have my makeup done.
“I really enjoyed doing makeup,” she announced, “you’ll be getting a full face makeup done with a definite dark smokey eye look and bright red lipstick just like mine. You’re not going to recognise yourself.”
With me now craving for the makeup application to commence, I was asked to lie back and close my eyes. Mistress commenced by wiping my face with a what felt like a damp cloth before adding a layer of foundation. I immediately fell in love with having makeup applied. I felt so relaxed as I felt Mistress skilfully using brushes to add the foundation.
“Time for a little blush and highlighter now,” Mistress commented, “to give those cheeks of yours a little colour and to extenuate your lovely natural cheekbones. You really do have a naturally feminine shaped face.”
I responded appreciatively before asking for my own reassurance, “all of this makeup will come off once we are done, Mistress?”.
“Definitely,” she replied, “all of my makeup is natural and washes off easily.”
“Now time to make those eyes of yours just like mine!” Mistress added enthusiastically.
If I hadn’t before, I undoubtedly now knew that Mistress was enjoying herself nearly as much as I was. Given my euphoric state, this was quite an achievement.
If felt incredible as I could feel pressure on my eyeballs as Mistress started adding what I suspected was eyeshadow. It was so nice and calming having it applied and then blended with various small brushes. Mistress also used what felt like a pencil to better define and shape my naturally pale eyebrows.
“Just need to give those brows of yours that unmistakable feminine thinned arch so you look your best for your ear piercings!”, Mistress commented cheekily as she went about her work.
I had been so engrossed in everything else that I’d almost forgotten about having my ears pierced.
“Yes, can’t forget about getting my ears pierced can we”, I responded with a chuckle, “that’s what I came here for after all!”.
“Eyeliner time my dear”, Mistress announced, ”my favourite part of makeup”. Starting at the outer edge of each eyelid I could feel as little by little eyeliner was added, each stroke slightly overlapping the previous one. My excitement continued to grow as Mistress moved closer to the inner corner of each eye. Once the full length of each upper eyelid was complete Mistress spent more time redoing most areas particularly on the outer ends which were no doubt quite thick now and hopefully resembling her own eyeliner application.
“I think a little winged eye look too,” she added before I felt her continue to add eyeliner beyond each eye.
“It feels a little foreign having something drawn on your eyelids”, I responded.
“Yes, I’m sure it does,” Mistress responded, “just one of many new experiences for you today!”.
Mistress then commenced drawing on the underside of my bottom lashes before asking that I open my eyes and look upwards.
“If we’re going to have you looking glamorous with a strong smokey eye look I’ll have to fill in your lower water lines too,” she instructed.
I did as asked and with one hand Mistress pulled slightly below my right eye before filling in my waterline. I didn’t even realise that it was possible to add eye makeup there! While a little uncomfortable at first, and slightly scary having a foreign object so close to my eye, it wasn’t that bad. Within probably two minutes both water lines were filled. The smile on Mistress’ face clearly showing that she was pleased with her handiwork.
“You’re eyes look so good,” Mistress commented, “time to add some mascara to make them even sexier!”.
“Thank you Mistress,” I responded appreciatively completely zoning into every facet of what was happening to me.
“I just love this mascara,” she added, holding it out for me to see, “it will make your already long eyelashes even longer and much thicker too.”
After a few minutes of me needing to look in various directions as Mistress skilfully applied my mascara, my eye makeup was almost complete with Mistress just needing to reapply some eyeliner in a few areas to her satisfaction.
“The last thing we need to do makeup wise is to give you some beautiful red lips,” she said.
Mistress firstly used a pencil to extend and better define my lips. With a fine brush, she then added the bright red colour to match her own lips which shone under the light. Looking at her face I wondered how closely my own face would resemble hers. I knew that more than likely I would still look like a man wearing makeup but hoped that the addition of makeup would even partially reveal some part of my female self.
“That’s your makeup done my dear,” Mistress announced, “your makeup looks great.”
“I can’t wait to see it Mistress,” I responded.
“Not yet,” Mistress added, “not until you are fully transformed are you allow to look at yourself to see if you’d pass the salon’s female-only policy.”
“Ok,” I replied slightly disappointed.
“Better remove your restraints so we can get you dressed”, Mistress commented, “not that the belts were really necessary I don’t think as he were very well behaved while I did your makeup.”
“Thank you Mistress,” I replied.
“I would have thought that a man would have been very hesitant to have makeup applied,” she stated, emasculating me further, “you must really want to have pierced ears.”
“Yes Mistress, I do,” was all I could say in response.
With the seven belt restraints now removed, I was asked to stand between the medical table that I’d just been on and the bed that was covered in the items that I was about to be wearing.
“First thing we must do before getting you dressed is to hide away your maleness,” Mistress instructed taking the chastity cage from a nearby stand, “thankfully for you things appear to have settled down a little.”
I was asked to spread my legs as Mistress knelt separating the chastity device into two distinct parts. She requested that I hold the ribbed metal part and a small padlock and key while she kept the other piece in one of her hands. With her free hand she then, with a little gentle persuasion, pulled my testicles forward before placing the hinged ring behind my balls and closing it together on the upper side of my penis.
“That’s not pinching anywhere is it?” she asked as I responded in the negative.
She then took the ribbed part from my hand, placing it over the length of my shaft until it reached the hinged ring that was already in place. Taking the padlock from me, she then fed the curved part of the lock through drilled holes in both parts of the chastity device before securing the lock closed. My maleness was now encased and with Mistress removing the key and placing it to the side. Glancing down it looked so cool and I was immediately aware of its weight. Despite its awkward appearance, it felt very comfortable.
“Well that’s got that under control for the time being,” Mistress said returning to her feet, “can’t have that thing poking its head out later on, can we!”.
“No, that wouldn’t be ideal,” I replied as we exchanged grins.
“Time for some clothes now to complete your transformation my dear,” Mistress announced taking a pink lacy bra from the bed.
“Think this one will be the right size for you and I love the colour!”, she added jokingly.
The bra fitted well. Well at least as well as I’d imagine a bra to fit given this was more new territory for me. Next came a pair of large rubber breast forms which Mistress manoeuvred into place. I couldn’t help but instinctively reach up to feel them, cupping them in my hands.
“Oh, I see you like having breasts,” Mistress commented noticing the position on my hands, “I know you’re going to enjoy plenty more things we ladies get to experience.”
My self-groping now over it was time for the dress. Mistress gathered up the dress and arms first I slid into it with her assistance. When pulled down it only just covered my backside and my caged appendage. It hugged my body closely, especially over my fake breasts. I loved it.
“That’s a really good fit on you,” Mistress commented, clearly pleased with her selection.
“Please take a seat,” she continued, indicating the low bed which previously held many of the items I was now wearing.
Taking a seat, Mistress grabbed a blonde wig from beside me and holding it out in front of her started to manipulate it before having me help her place it onto my head. The sensation of feeling long hair against my face and neck was immediate and only continued as Mistress used a large brush to better style my new flowing locks. Having had short hair my entire life, having hair brushed was another new experience.
Hair now brushed, Mistress explained, “Time to show off those gorgeous long legs of yours,” as she took a stocking and had me stretch out one of my legs.
Within a minute or so both legs were now encased in dark stockings which did indeed make my legs look very different. The top of the stockings reached to very near the top of each leg with an intricate feminine lacy pattern confirming that, like everything that had gone before, I was in serious girl territory.
To complete my outfit Mistress then took a pair of high heeled shoes and tried to place one on my right foot. My foot being a size 11 men's she thought that this particular pair may be too small and this was confirmed. Taking a second option that didn’t have a back as such, she found a pair that fitted much better. The shoes were black with gold patterns and long thin straps which Mistress began to wind around my ankle and up my calf. The heel was 3-4 inches long and my first thought was how I was going to manage to stand let alone walk in them!
“They’re beauties”, I commented as Mistress comically battled the unruly shoe straps which refused initially to fasten as she would have liked.
“Yes, they’ve got a mind of their own,” she replied as we both broke our roleplay personas and laughed at the situation.
Shoes now fastened and us both now realising that the strict roleplay had run its course, I think we both just let our natural instincts to emerge. From this point onwards, I at least just spoke freely not having to consider my comments and reactions to fit a hypothetical scenario.
Mistress requested that I stand and with her hand supporting me to stood up and instantly felt like a giraffe. It is amazing how much your visual perspective changes being several inches taller. I was now quite a bit taller than Mistress wobbling like a newborn foal as Mistress, still holding one of my hands, encouraged me to take a few steps. After successfully negotiating these few steps Mistress withdrew her hand and suggested I walk up and down the room a few times to experience better wearing high heels. I did so very nervously at first but by my third or fourth pass was making much more confident progress.
“You look amazing, especially those long legs of yours” Mistress commented, admiring her creation, “there’s no way that anyone in the salon will suspect that you are anything but an attractive lady.”
“Thank you Mistress,” I replied.
“Ok darling,” Mistress announced, “I think that the time has come to have your ears pierced!”.
This statement had my heart rate increase exponentially. While having my ears pierced was central to what I wanted to experience, the remnant signs of any piercings were the thing that upon leaving the safety of Mistress’ place, I feared the most.
I will include here an excerpt from one of the emails I’d sent Mistress leading up to our meeting today which outlined by trepidation:
My main concern is that the ear piercing marks will remain once I’ve left you. I think that very small gauge needles will be fine but if you’re considering using large hoops the marks left due to the thicker earring posts would be too noticeable afterward. I would love nothing more than experiencing whatever you have planned for me with a large pair of hoops swaying and dangling from my lobes the whole time but think this would undoubtedly leave marks. What do you think?
With my mind racing with a volatile mixture of excitement and fear, Mistress took one of my hands and helped me over to the medical table.
“Please lie down like before darling,” she instructed, “I don’t think that any restraints will be necessary this time as long as you promise to be a good girl and lie very still.”
“I promise,” I replied with us both exchanging a cheeky smile.
Again the bright dental light shocked my eyes and seeing this happen Mistress told me to close my eyes until my ears were done. Upon closing my eyes my auditory senses were heightened considerably hearing Mistress preparing the piercing materials on one of her tray tables. I had tried to look at the tray I noticed at the head end of the medical table just prior to lying down but Mistress had kept everything hidden under a large piece of paper towel.
Mistress then pushed back my newfound blonde locks to fully expose my ears. I was seconds away from entering what I would call my nirvana state, my encaged penis now straining within its confines. With I presume some sterile wipes, Mistress then sanitised both of my earlobes and after a small amount of noise emanated from the tray behind my head I was ready to be pierced.
“Ok young lady,” Mistress instructed as I felt her touching my left earlobe, “I want you to take a deep breath, and then blow it out”.
At the top of my inhale I felt the needle move painlessly through my lobe.
“Well done,” Mistress commented and within a few seconds, “now, same as before, please take a deep breath in and then exhale”.
Perhaps knowing exactly what to expect the second time, this piercing seemed to take longer. It was almost as if time had slowed down. I felt Mistress gently touching my right earlobe and then the sweet sensation of the needle penetrating my flesh. The adrenaline rush was indescribable and for several seconds afterward, I was floating on clouds.
In my intoxicated state, I then felt Mistress fiddling with my left ear.
“Just lie still darling,” she said reassuringly, calming me immediately, “you know this is what you want”.
Such was my euphoria at my current situation I did as asked lying dead still as Mistress played with my left earlobe. A short while later she repeated whatever she had just done on my right ear. Deep down, and despite me in emails expressing concerns regarding having actual earrings inserted, I knew Mistress had placed earrings in my freshly pierced lobes. The realisation of this happening should have caused me to become fearful but I loved every second and had no sense of anxiety.
“All done,” Mistress announced bringing me slightly out of my trance-like state, “come with me so you can see yourself.”
Sitting upright on the table I immediately felt an extra weight pulling slightly on each earlobe but looking back, strangely didn’t have an understanding of what was now attached to my ears. I then noticed that a full-length mirror was illuminated across the room. While assisted by Mistress, I’m still not sure how I managed to walk across the room given my daze and in the high heels but I somehow found myself a metre or two back directly in front of the mirror.
What was reflected was beyond even my wildest dreams. I looked like a woman in every sense, except perhaps the bulge from my swollen caged cock and balls.
“Thank you Mistress,” I commented quite choked up emotionally, “I can’t recognise myself.”
“It’s my absolute pleasure,” she replied proudly, “move closer and have a better look at your beautiful makeup and your pierced ears.”
I did as suggested, instinctively first looking at my newly pierced lobes. Each piercing contained a large thick pair of silver hoops which were around two inches in diameter. Again looking at them swaying in my lobes gave me no fear even though I now knew that the marks left once the hoops were removed would be more noticeable. While I have had my ears pierced with studs several times in the past, having this gorgeous pair of large hoops rocking rhythmically in my ears with each movement was the ultimate piercing experience for me.
“I was going to just pierce you with thin hypodermic needles but when I went to order them online I noticed some hollow needles used by professional piercers. I knew immediately upon finding them that I could give you the beautiful hoops I knew you craved given our emails.” Mistress explained.
“I love them, thank you Mistress”, I responded appreciatively.
“I watched a few YouTube clips and basically I just needed to pierce your earlobes pushing the hollow needle almost all the way through,” Mistress continued, clearly proud of her new skills, “the hoop posts then get placed in the blunt end of the hollow needle and everything gets brought through the new hole and the needle just comes out at the back leaving the hoops’ posts in your earlobes.”
“They look amazing and something that I never thought I would see,” I replied still enthralled with the hoops.
“I loved doing it as I knew it would be such a thrill for you,” she responded.
Eventually, my focus shifted away from my ears and I inspected my makeup. My eyes especially were captivating with the dark tones and colours used. The eyeliner was perfect and matched the style Mistress herself exhibited so wonderfully. A few small tears welled up in the corners of my eyes as I looked at myself with female eyes for the first time. My visit to Mistress had well and truly exceeded all of my dreams and expectations and Mistress’ voice speaking to me let me know that she was far from finished with me.
“Take a seat here please,” she directed, placing a stool in front of the mirror, “time for some more fun!”.
I did as requested and almost immediately watched my reflection as Mistress starting to caress my body sliding her hands up and down my legs, across my crotch and hips. She played particular attention to my captive cock and balls sliding up my dress that had barely covered them and squeezing and pulling at them. Given there already swollen condition, this was incredibly arousing given their current sensitivity. Moving further upwards and reaching from behind me she firmly cupped my breasts pulling them back towards my chest so that they almost felt real.
“Play with yourself my darling,” she said seductively, “you deserve it for what you’ve done today.”
At this, she took my hands and placed them on my breasts. They now felt very much part of me and feeling myself was so pleasurable. Looking into the mirror again I watched Mistress who was still standing behind me, pull back my blonde flowing hair to behind me exposing fully the gorgeous large hoops that were also part of me. Taking a hoop in each of her hands she starting moving them gently at first and then became slightly more aggressive tugging harder and harder with each passing second. As you would imagine, my ears being highly erogenous for me, the pulling and slight stinging given that my ears had only just been pierced, took me to an even higher state of ecstasy than when they were actually pierced.
“Look at yourself my darling with these perfectly pierced ears,” Mistress almost chanted as she continued to pull on my earrings, “you love being a beautiful woman.”
All of this attention and multiple forms of stimulation were too much for me. Despite being restrained, my cock exploded like never before much to Mistress’ surprise and then excitement.
“Well, I didn’t expect that,” she said nonchalantly, “you really do have a thing for pierced ears don’t you.”
“I’m sorry Mistress, I couldn’t stop myself,” I replied apologetically and embarrassed at what had just occurred.
“It’s fine darling,” she responded, “that was so cool!. Don’t worry, I can easily get you cleaned up”.
Mistress left me alone for a minute or so while she busied herself getting something to rectify my accident. I spent this time gathering my thoughts a little and for the first time since our session started, I felt a real sense of guilt for what I chose to have happen to me. Glancing in the mirror I still absolutely loved how I looked, especially my pierced ears, but perhaps due to the sexual release, certain hormones had kicked in bringing a strange, intangible feeling of regret.
On returning to me, Mistress, being a very intuitive person, immediately sensed that my mood had shifted.
“Are you ok?” she queried with genuine concern.
“Yeah, just feel a little embarrassed and uneasy for some reason,” I replied quietly.
“That’s completely normal and I see it happen a lot,” she responded reassuringly, “you’ve been taken to such a high state of consciousness and then what happened causes your emotions to drop so quickly.”
“We can stop now if you like?”, she queried, “it’s completely up to you.”
“No, I’d like to continue and see what else you have planned for me,” I replied appreciatively due to her care, “if that’s ok with you?”.
“Of course we can,” she answered, “let's get you cleaned up a little first”.
A brief delay ensued as Mistress needed to search for the key to unlock the padlock on the chastity belt. Key found, the lock and then device were removed and my substantial accident cleaned. Now in a much more optimistic and assured frame of mind, I was ready for whatever Mistress had planned for me. A quick play with my hoops also helped me return quickly to my female persona who had briefly left the room.
“I think because your clitty got a little too excited you need to be punished,” Mistress announced, “time for a good spanking I think to make up for what happened.”
Mistress then turned the dental light over illuminating a very large, high upholstered table whose surface was about the dimensions of a single bed mattress. Prior to walking over there though we mutually decided that my high heels shoes had served their purpose and were removed which made my walk across the room much more confident. We joked that if I’d tripped and sprained my ankle it would be a difficult story to explain!
When I got to the table, there was a face-sized hole centred at the far end, a similar style as you would see when getting a massage. This table though differed considerably in that there was also a much larger second hole around half way down that I was soon to discover was to allow Mistress unrestricted access to my groin. Surrounding the table was an intricate frame of scaffolding with many chains and other unidentifiable items attached. Due to its prominent position, I did take notice of a tubular metal bar connected at its middle to the end of a chain. It hung about a metre above the table’s surface but its purpose and use at this stage was not known to me.
“Please lie face down on the table with your arms down by your sides,” Mistress instructed, using a noticeably more authoritarian tone.
I did as requested finding it quite amusing that I needed to adjust the angle of my hoops to allow me to place my face in the smaller hole.
“I’m going to restrain you again for what I’m about to do to you,” Mistress declared, again with a more domineering voice.
To restrain me Mistress firstly stretched each of my legs into their respective corners before my ankles were bound in place. Like just prior to having my makeup applied, multiple thick belts secured me again, much tighter than my previous experience. Once tied to Mistress’ satisfaction, I tried to move a little but this was futile. For many people, this would have been very disconcerting and terrifying but for some reason, I found it extremely relaxing and safe.
Mistress tracing a finger up my still stocking covered leg drew my focus from daydreaming and back to her. After some rubbing of my exposed bum, she commenced spanking me gently. Her strokes were metronomic, alternating between cheeks and gradually building the intensity of each stroke. Not being able to see what was occurring only made the slapping sound and the sting of her spanking me feel so much more acute. No doubt my spanked backside would now have a nice bright red glow I thought.
Mistress then paused and stepped away for a few seconds before returning. She then attached an additional two restraints, one across each of my upper thighs, through the large hole and then fastened tightly. I then heard what I soon confirmed to be Mistress applying surgical gloves. Soon after I felt the coolness of presumably lubricant being drizzled down my arse crack. I immediately sensed my drained, still sensitive cock come back to life.
“I see you’ve had your crack waxed for Mistress,” Mistress exclaimed rhetorically, “you really are wanting this aren’t you, my little slut.”
It was true, a few days before my appointment I had had my crack waxed in anticipation of what I’d hoped for, and was now about to experience.
“Let’s have a little look here to see how much you really want this my pierced slut,” Mistress added.
Her description of me being her pierced slut only heightened my anticipation of what was to come next. Reminded about my piercings, I wriggled my head from side to side as best I could to once again feel the weight and pull of the large hoops attached through my earlobes. The endorphin release from this act alone was phenomenal.
After running her fingers several times across my hole one of her fingers started to slowly penetrate me. Despite my bodies natural reaction to push it out I tried to relax and embrace Mistress’ advancing finger. After some delightful movement in and out I felt a second finger joining in and then perhaps even a third as Mistress began moving in a distinctive rhythm which I would have reciprocated if not for my immobility. Using her spare hand, she took my growing cock, sliding her lubricated, gloved hand firmly up and down my shaft and grabbing my dangling balls.
After a magical few minutes of dual hand attention, Mistress stopped and again I heard her take a few gentle steps away from me briefly.
“Let’s see if your pussy likes to have something other than my fingers inside it,” she announced, “this is a vibrating butt plug, I think you’ll find it more than enjoyable.”
I then felt the tip of the butt plug being slid inside me as I tried to relax to make its path easier. With each subtle use of pressure and twisting, Mistress positioned the plug further and further inside me. Once in place to Mistress’ satisfaction, it was in much deeper than I had felt her fingers reach.
“Are you sure that you’re a virgin like you said in your emails?” Mistress queried, “you took that plug far easier than I thought you would. You’re doing very well.”
“Thank you Mistress,” came my somewhat muffled reply due to the placement of my face.
“I just need to tie the butt plug in now before we have some real fun,” she declared excitedly, “their vibration sometimes makes them slide out!”.
What felt like a thin piece of string, like a shoelace, was then looped around the base of my cock, drawn up and around the butt plug before being fastened to one of the belt restraints. Less than a second later Mistress turned on the vibrating plug with immediate impact. It is still difficult to describe the sensation to give it justice. Something like being tickled and aroused simultaneously and nothing like I’d ever felt before.
The vibrating plug doing its job more than perfectly given my slight guttural groans of pleasure, Mistress recommenced spanking me. Her initial blows stinging and sounding more intense than any of her earlier strokes. The dual activity of both the butt plug pulsating deep inside me and Mistress’ now full-blooded slaps on my bare backside was taking me well and truly to an uncharted headspace.
“You love being my pierced slut don’t you,” she almost ranted at me, “tell me you love it!”.
Instinctive I responded, “Yes Mistress, I love being you pierced slut, thank you Mistress.”
After this intense dialogue was repeated a number of times Mistress ended the spanking by just gently rubbing the palm of her hands over my now tingling butt. Soon after, the butt plug was switched off, untied and effortlessly and painlessly removed. Next, the multiple restraints were one by one removed and I was asked to roll over onto my back as Mistress removed and disposed of her gloves.
“You’ve done so well my darling,” Mistress commented proudly, “you deserve to end our time together with something very special.”
“Thank you Mistress, what do you have in mind?”, I enquired enthusiastically other than a small hint of trepidation.
“I’d love to take you with my strap-on”, she requested, “I know that you’re a virgin, so what better time to pop your cherry”.
I simply replied with “I’d love that.”
After by acceptance of Mistress’ offer, she went over to another mobile tray table and pushed it close beside the upholstered table that I was lying on. It was clear to me immediately given how the multiple items were all placed neatly on the tray that Mistress had planned to finish our time together this way should I be willing.
Taking my stocking encased right leg, Mistress attached an ankle restraint before asking me to lift my leg vertically where the purpose of the tubular bar hanging down became apparent. Using a carabiner-style clip my leg was then connected to one end of the bar. The same process was then repeated on my left leg until both were suspended at a 90-degree angle to my torso. Again this bondage element of our session, like all other restraints, produced excitement rather than any sense of fear in me.
“Nearly forgot to turn this on,” Mistress commented moving over to the side of the scaffolding and switching on a light above me. The lights primary purpose, other than making our area brighter, was to illuminate a very large mirror that allowed me to see the entire bondage table.
I was immediately infatuated with my reflection. My blonde wig looked like something part of a photoshoot, spread out and contrasting beautifully across the black upholstery. The dark smokey eye makeup and bright red lipstick also reminded me of my feminine appearance as did the tight-fitting black dress and prominent breasts. Naturally, the reflected sparkles emanating from the large silver hoops pierced through my ears though gave me the greatest sense of happiness and I couldn’t resist a further chance to play with them.
“You know darling,” Mistress commented noticing my self-indulgent admiration, “you could so easily pass as a woman permanently. Your facial bone structure is so feminine and those stunning legs of yours would certainly turn so many heads”
“I don’t know about that Mistress,” I replied, “but thank you for the compliment.”
“You certainly could,” she continued, “next time you come and visit me, I think an excursion with you fully dressed would be perfect. Get you all dolled up like now and of course pierce those ears again. It would be so much fun, you’d love it!”.
“It does sound very tempting, but also very scary,” I responded for the first time coming to the realisation that this session could be more than a one-off experience. “Might have to get some heels to practice walking in though between now and then or it would be disastrous!”.
“True,” Mistress laughed back, “you did struggle in them so if that’s the only worry, you’ll be fine.”
My attention was then drawn to Mistress preparing for her to take my virginity. Something that I had hoped may happen today but wasn’t certain about. I watched her take and then step into a harness and tighten it around her black latex covered waist. She then took hold of the smaller one of two cocks placing a condom over it before attaching it to the front of her harness. Seeing this filled me with anticipation and my heart rate and own cock’s interest increased dramatically. Next, she placed a condom over the considerably thicker and longer cock before returning it to the tray table. A third condom was then placed onto a handheld device but I didn’t know its purpose.
“This is a Hitachi machine”, she said holding it out closer to me, “it will be your new best friend!”.
With Mistress just double checking everything is in place as she puts on another pair of surgical gloves, I again glanced up at the large ceiling mirror. Mistress was right, the reflected image did look every part female and the knowledge that I could repeat this experience and more with Mistress thrilled me.
With Mistress now joining me on the table, seated with her appendage very close to its proposed target I remembered the article I’d read about giving permission to yourself to enjoy the experience and prepared to do just that.
“I’m just going to place a couple of silicone cock rings around your cock and balls,” she informed me, “they heighten sensitivity as well as add a bondage element.”
Cock rings in place, Mistress generously applied lubricant to her cock and my exposed crack before returning it to the tray. After a brief fingering to check that I’m ready she shuffles herself forward until her thighs are touching my slightly raised backside.
“Enjoy your first time my darling,” she comments as I watch as she reaches for her cock that had been resting against my own cock and balls.
Intently I watch in the mirror above as her cock gradually goes deeper into my pussy until fully inside me. I’m asked if I’m ok and I respond in the affirmative. With this, Mistress starts to thrust ever so slowly at first, each movement so satisfying. I take a few seconds to take in as much of my current situation looking again at my long blonde hair beneath my head, my beautifully made-up face, my clothing, and breasts. My perfect hoops now dancing in my ears with each of Mistress’ thrusts. I am undoubtedly in my fantasy paradise, my mindset now embracing everything completely as a woman.
After several minutes of bliss, Mistress withdrawing her cock brings me slightly from my dreaming.
“I want your first time to be extra special,” Mistress instructs as she reaches overtaking the much larger cock from the tray before showing it to me, “I’m going to fuck your brains out with this!”.
I do not respond, accepting without hesitation Mistress’ statements. I watch her switch over cocks and coat her new member in lube.
“Lie back and close your eyes,” Mistress whispers and I do as asked.
Nervously now, I feel Mistress’ cock begin to penetrate me. Its much larger girth instantly stretching my pussy well beyond its predecessor. After a period of gentle pressure, I feel a distinct pop and slight freedom as it moves beyond a point that was inhibiting its progress.
“Good girl,” Mistress whispers reassuringly, conscious of what has just happened.
I open my eyes to look at Mistress who is smiling back at me in approval.
“Close your eyes,” she again whispers, “so you can better feel me fuck you”.
As instructed, I lie back down but not before sneaking a look at the ceiling mirror. I am shocked to see that the vast majority of Mistress’ larger cock is now well and truly inside me. The very image and realisation of that were mindblowing.
Mistress’ thrusts and tempo immediately increase and I start to involuntarily vocalise my delight which only further enthuses Mistress. I find my hands now grasping Mistress’ spread thighs, reciprocating her energy pulling her even deeper until we are both physically spent.
“Oh my god!” I announce, as we mutually slow our tempo to minimal movements.
“Wow that was incredible,” Mistress responded, also catching her breath.
“I think we might get you to come again to finish off if you like?” she continued.
“I’d love that,” I answered appreciatively.
Taking the Hitachi machine in one hand and with her cock still very much inside me, she turned it on placing it at the base of my engorged cock above my balls. The strong vibration of the Hitachi was overwhelming and its contact for even a few seconds was so intense. Moving her hips to continue fucking me, Mistress alternated between running the Hitachi around my cock and delivering the most wicked handjob with her spare hand. Skilfully Mistress took me to the brink of cumming numerous times, always somehow knowing exactly the right amount of attention as not to overstimulate me. My head was spinning more than at any other time during our session which was something of an achievement given what had transpired between us.
“I think it’s time to make your clitty squirt my dear,” Mistress proclaimed, “grab your hoops and enjoy!”.
Relishing holding my hoops and pulling them to feel the pressure through my earlobes, Mistress started thrusting again with long and deep movements. With a regular rhythm now in place, she then recommenced giving me a hand job before placing the Hitachi against the base of my cock and also vibrating powerfully against my balls which were being held forward by the silicone cock rings.
There are not sufficient words to describe what was occurring within my mind and body. In normal circumstances, any one of pulling on pierced ears, being fucked with a large strap-on, receiving a handjob or the vibrations of the Hitachi would have been mind-boggling. Having all four at once was like being electrocuted from the inside out and nothing like I’d ever experienced. So many times in the ensuing seconds I wanted Mistress’ attention to stop as I couldn’t take any more stimulation but simultaneously found myself never wanting it to stop!
“Good girl,” Mistress commented as I climaxed over and over again, “that’s what it’s like when a woman has multiple orgasms. They’re amazing and so pleased that we managed to get you to share with me the ultimate feminine experience.”
I am honestly not sure of the events of the next few minutes due to my delirium. I just lay back looking at the mirror above trying to give my brain time to recalibrate a little and absorb everything that had just occurred. My next lucid thought was Mistress, now down from the table and having removed her harness, disconnecting my legs from where they had been suspended and unshackling the ankle restraints.
Mistress assisted me down from the table and immediately hugged me firmly which was lovely. Even though we had really only just met, it felt like I was embracing a dear friend given the enormity of what had transpired between us.
“I can’t thank you enough for how you have allowed me to explore my feminine self Mistress,” I said with the highest degree of sincerity, “you’re amazing.”
“It’s been my absolute pleasure to watch and help you to delve into your hidden desires and feelings and open yourself to embrace your femininity and new experiences,” she responded.
To conclude our session Mistress took me over to in front of the full-length mirror for one last look at me. Well at least the external feminine image of me. We first removed my stockings, then my gorgeous little black dress followed by Mistress reclaiming the breast forms and then unclipping my sexy pink bra.
Retrieving a stool and placing it directly in front and close to the mirror, I was then asked by Mistress to take a seat so that she could remove my non-clothing items. Surprisingly quickly, Mistress efficiently removed every trace of makeup and when my wig was also taken away I was left looking like my normal self who had entered Mistress’ studio an hour and a half before.
I was now completely naked and very much my male self had returned with the exception of the most gorgeous pair of large silver hoops that I had ever seen dangling innocently from my lobes. In another example of Mistress’ professionalism and thought, they were the last feminine sign remaining. She had planned every detail of our session perfectly and I will always be indebted to her for the environment she created for me.
I have no doubt that moving forward in life my thought processes, outlook and acceptance of my inner woman will be very much influenced by her care, guidance and ability to take me to places that I never even dreamed existed. Thank you!
“It’s time,” I said to Mistress as I sat upright and watched regretfully as Mistress quickly removed both of my hoops.
A few droplets of blood were swabbed and within a minute or so only small, barely noticeable puncture marks remained. While the marks did look very obvious to me given I knew how they got there, the rest of the world mercifully would not have even noticed anything different about me.
I had a shower before getting dressed and saying our goodbyes, for now.
“Thank you Mistress,” I simply said as we parted, hugging her one last time as I walked out the door.
“See you soon hopefully, take care,” Mistress responded closing the door.
Walking away while attempting to clear my head to return to normal life, I was so pleased that I’d accepted Mistress’ plan to allow me to get my ears pierced!
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