Ok, i am a few days from my session with Mistress Natalie from NYC (www.mistressnatalie.com) and it was PHENOMENAL!! The following is a fictional embellishment, any acts that violate any laws would have been simulated or fictional. It was almost as if the session was the culmination of my 20 year BDSM career...and it left me wanting more. I knew that I would be in NYC and posted a request for a recommendation on Domina.ms. One of the users there posted a recommendation (Thanks Again "The Thomas"!) for Mistress Natalie. Then Mistress Ayn, a founding member of the board also recommended Mistress Natalie. I contacted Mistress Natalie via email to arrange a session about 2 weeks into the future. My references were verified (i will forever be grateful to those who confirmed my references and allowed this session to take place). Mistress Natalie scheduled a telephone interview and directed me to send a little more info via email. She was very open and personable on the phone. When I shared about my session in Amsterdam, (also posted on this board) she said "Cool" and it sounded sincere! we talked about what I hoped to do in a session- I wanted to be feminized, and experience public humiliation for the first time, in chastity and getting lap dances at a strip club so all the dancers would know what a sissy cuck i am. The plan was then to return to Her dungeon so I could be taken like a woman with a strapon. I left the conversation pleasantly excited and was requested to share a bit more information about a wide variety of bdsm topics for next steps.
My anticipation began to build, I was lucky to be introduced to this Woman who was very cool, friendly and fun on the phone AND i get to enjoy a BDSM session with her.....Awesome! In the follow up email I shared things that I have never shared before -it as liberating. The schedule was confirmed, deposits were made, I may have visited her website incessantly pouring over every picture I could find.....and She is possesses that rare combination of being both extremely Beautiful and very Cool!!!
So as the session approaches, I am given assignments- I need to go to a nail salon and get a manicure and I need to go lingerie shopping to be outfitted before I visit Mistress Natalie. The recommended lingerie stores are Victoria's Secret and Macy's, the nail salons are just typical nail salons (I had no idea how to do the manicure, I wasn't sure what to "order", but Mistress Natalie advised me via email. I spent some time trying to pick the right lingerie from the Macy's and VS websites, hoping to be prepared for shopping day.
I arrive in New York, get settled into my hotel near Madison Square Garden and decide that I am going to visit the Famous NYC BDSM store, "Purple passion" first.
I am kind of preppy in style, so I walked in there on a Sunday in a pink button down shirt, Khaki jeans and loafers and was immediately asked how I could be helped. SO I am kind of nervous at this point and my voice is a little shaky. So I explain that I am interested in some lingerie, Lolita, the woman at the counter showed me around (and was wonderful!) then introduced me to a transgender young man early in transition, RIO to help me. We select a corset and opaque stockings with laces going up the back. I go in to try the corset on and as I am struggling to put it on- RIO pops his head in to check on me, I felt pretty feminine asking for some help with my corset and he approved after we got it all connected. Pretty sure he popped his head in to check me out too! I asked for help with panties but they didnt have the femme style that I was interested in there, more leather and latex. He tried to steer me to a gaff and I admitted that I would be in chastity- well after that admission, Rio is a person with a hundred questions, "which style? When?"
my response "I dont know, I'll find out tonight".
A Knowing look and a nod from Rio, "well come over here and see some examples of what you might get".
I checked out the devices decide that if I buy one, it would be a pink one...and who the hell wants one in Camouflage? I pay for my purchases. Rio gives me a teasing "have a good time tonight" as i leave, I am exhilarated and a bit embarrassed. It is still early, so I head back to the hotel and shave from my neck to the tops of my thighs- this uses 3 razor blades. Also it takes about an hour and the flexibility of a yoga guru, I have the time, but not the yoginess- there may be a stray hair or two.
With my corset and stockings on, I head to Victoria's Secret, a short walk away. Halfway there, my right stocking is falling down -they were supposed to be self retaining, so now I am getting panties and a garter belt too!
Victoria's Secret on broadway is a 3 story store that is packed with beautiful women and their Husbands/boyfriends. I am sure I saw at least 3 professional models there, i am the only solo male and probably the only sissy that i see in the store. i am excited by the beautiful women in the store, but more because i want to be beautiful like them... i search for the right thong, and decide that i LOVE the hot pink g string and I look for a garter belt, I pick out the matching pink one and buy it- ready to rush back to the hotel and put them on.
So now, i am in a corset, g string panties, garter belt and stockings under a pink buttondown shirt and khaki pants - I head back out to get my nails done. the shadow of the corset is visible under my shirt and I swear the concierge can see it. he is a big guy, an alpha and i am a cuckold sissy- i think he recognizes this.
i go to the nail salon, another short walk away. i have never been to a nail salon before, Mistress Natalie instructed me via email "just go in, ask for a Manicure and pick a fabulous color". I request a manicure from the asian woman in the store, there is a beautiful, dressed for business african american woman two seats away that gives me a sidelong glance. the woman who begins to do my nails is probably in her 50's and has very soft hands. she files and does all the various preparations and then tells me she is done. i ask when i get to choose a color (another glance with raised eyebrows from the woman a few seats away)...(i am not sure I can do this, but I DO NOT Want to disappoint Mistress Natalie), a clear coat is applied to my nails and then I am taken to the nail dryer. the Woman that did my nails begins to massage my shoulders and back- she definitely feels the corset and doesnt stop.....my face becomes fire engine red and I stammer "that is nice, thank you" after about 10 min- the clear coat is dry and the nail woman says "ok thank you"
I ask "what about the color?" she grabs my hand and says- "this is a very nice color you go now"....this was not said in a quiet voice...all eyes are now on me. I depart the salon in shame and head to Mistress Natalie's neighborhood. walking over is am excited and nervous...and sissified under my clothes.
I am a bit early so i have a beer in a nearby pub and watch NCAA selection Sunday for a few min. at the appointed hour, shaking with anticipation, I confirm my arrival and get to meet Mistress Natalie!
She is every bit as beautiful as she looks online, her presence in the room only enhances her beauty- she greets me warmly and i give her the gift of oolong tea that I brought for her. We chat for a minute or two, i am pretty sure that i spoke in complete sentences, but in my head this is happening: OH MY GOD THIS IS REAL!! I AM IN A ROOM WITH THIS AMAZING WOMAN AND SHE IS TALKING TO ME!!!
She asks about my "adventures" of the day and I share the story of the nail salon, she smiles at my humiliation and I realize that I would do almost anything to keep seeing that smile! I tell her that my lingerie doesn't match as well as i hoped. She points and says "let's see! take it off" motioning to my clothes. I begin to take off my clothes and fold them on the chair, I dont want to offend her by being messy or careless in her meticulous dungeon- looking around, I see her suspension equipment hanging from the ceiling, ropes and whips along one wall, an extensive medical setup on the far side of the room,
A padded St Andrews cross is on the other wall and a long padded bench is in the center of the space. It is a good sized dungeon and i hope to spend A LOT more time there. I mention that i might be stalling by folding my clothes, she laughs again (i love that sound) and I am down to the sissy frillies- she is pleased by the corset and tightens the suspenders on my garter belt - my little soldier is now standing at full attention with her touch so close. She guides me to the side of the room where the medical equipment is and has me take a seat, she puts hot pink lipstick and mascara on me. there is no hiding the hot pink lipstick - it is obvious (and matches my panties nicely!). I am taken to the long padded bench in the center of the room and directed to lie down.
As she prepares a few things, Mistress Natalie instructs me on what my safeword is, but she also says that I must do my utmost to please her so that I can earn the opportunity for future servitude- I hang on every word and want to do nothing more than please her!! I dont exactly know how the evening will progress only that we have discussed certain things and i hope we can do some of them, this unknown is also VERY EXCITING for me. Mistress Natalie takes control of my body, telling me that she is doing so- first she places an electric band around the base of my sissy clit (now her property) and a complementary electrode is places at the base of the clit- she activates a remote control and the most wonderful tingling sensation makes me moan with pleasure- she asked me to tell her when I felt it ...the sissy moan was confirmation- i whispered "that is nice" Again, I am rewarded with that smile! the next device is retrieved- it is shaped like a giant pink peanut, maybe as long as my index finger and 2-3 fingers in diameter - "ooh it is big" I say, suspecting where it will go - She activates a remote control and it buzzes in my hand - She says "I will control every part of you tonight" (i yearn to tell her that she already does) and she directs me to get on my knees, panties down like a slut - fingers penetrate and lubricate, it is heavenly, this deflowering, i LOVE IT, it takes a bit of help, but the pink peanut finally slides home- i wiggled my hips like a good sissy to help matters. Mistress plays with the remote controls, with a devious smile on her face- i am writhing on the table in undeserved sissy pleasure. Mistress attempts to put the chastity device on my sissy clit, but the excitement makes the sissy clit stand up, almost like a man's cock, but not quite so big - Mistress goes to get ice to calm the situation and directs me to "think of decaying puppies" which makes me laugh. upon her return, I am directed to close my eyes as she attaches then fastens the chastity with a silver lock. It looks beautiful as I open my eyes afterwards. Mistress then attaches nipple clamps to me under my corset- I am not super into nipple clamps, but I don't want to make her unhappy- the pain is welcome for the first time! i am directed to get dressed as we prepare to go to the strip club together. She puts a shirt over her leather bra and comes to me with the chastity key in hand. Mistress Natalie then puts her Key in a green plastic box and asks if I know what the box is, I respond no - she says that if i am good she will give me the combination tomorrow morning via email to release myself from chastity and I can mail the device back to her via a prepaid postage box the next day before I depart. I am crestfallen, there will be no release for me tonight; i am impressed -holy cow, that is a devious mind!!!
The Uber is arriving so we head downstairs- Mistress surprises me by activating the remote controls and I moan and wiggle my hips as the devices in my sissy pussy and on my clit force me to sashay with pleasure. I realize i am in public now and need to tone it down a bit.
The Uber Arrives and it is a shard uber with only two seats left- hardly suitable for a sissified person in lipstick and mascara and a Dominatrix -Mistress Natalie dismisses the Uber and we get in a Cab - She directs it to the strip club. shortly after we enter the cab - the remotes are activated, I make a sissy noise ...a high pitched "oooh" and try to recover, protecting my retreating dignity in front of the cab driver by saying "there's lord and Taylor, my favorite store". Mistress Natalie only laughs and starts to tell me how much she enjoys what she does because it allows her to do things like the crazy session that we have just begun- I am overjoyed that she is happy and i play a small role in that. Then we arrive at the strip club.
I pay the cabbie and we go into the club, the lights are low so the bouncers that allow us in dont see my lipstick, we give Mistress Natalie's Coat to the coat check woman and head inside, there are maybe 3 customers in the Club, and maybe 8 Dancers. No one is on the main stage, it is relatively quiet. Mistress Natalie selects a table in the middle of the club, I pll out her chair and we sit- Immediately the waitress comes over to take our drink order - Mistress Natalie asks "do you have a really feminine, fruity drink with umbrellas?"
The Waitress "Yes how about a Cosmo?"
Misrtess Natalie (Pointing at me) "SHE WILL HAVE ONE OF THOSE"
Wow, I am a bit embarrassed now-again. Mistress Natalie orders a white wine. Two dancers join us, Eva is very talkative, the girl with her is not Eva is a curvaceous woman, her friend is more slender. Mistress Natalie indicates my feminine drink and uses feminine pronouns to refer to me as we make small talk. She activates the remote controls and I cant help but make sissy squeals and gyrate a bit in my seat. Mistress Natalie points out my lipstick and tells Eva that i am wearing lingerie under my clothes. Eva says that they have a room with extra dancers clothes that They should take me to and dress me up. (Oh my god -Is this really happening?!?). Mistress Natalie tells them that I am in chastity and shows them the remote controls. She gives the control for the vibrating plug to Eva ....who proceeds to run it (and me) through its paces, intensity settings and Pulsation modes. I am going out of my mind. Mistress Natalie requests a lap dance for me- Eva is beautiful and dancing on me- She tells me she likes to use a strap on, and starts pressing her leg between mine so the plug vibrates more intensely. Mistress Natalie activates the electric device on my sissy clit....my eyes are rolling back in my head in pleasure. Mistress Natalie whispers in my ear what a sissy I am and how I need to be in chastity as my Clit is not good for anything else. my clit is desperately trying to grow but the chastity prevents it, I am pretty sure I lost the power of speech, i was so excited. Eva checks all my lingerie- Panties, garters, unbuttons my shirt to see the corset and plays with the Nipple clamps. She pulls the left one off and Mistress Natalie puts it in her purse. I tell Eva that I put my panties on OVER my garters like a good Slut (i can take off the panties without the garters), She Smiles. Eva's companion has gone and the dance is over. I pay her and she brings two more girls over, a Beautiful asian girl and another very curvaceous Read head with many tattoos. They both get the orientation for the remote controls and I get another out of this world Lap dance. The vibrating plug is vibrating in my body and the chair and I can't stand it- can a sissy clit shatter a plastic chastity device from becoming too excited? At this point the Dancers have unbuttoned my shirt - everyone in the club can see my corseted upper body. The Dancers convince us to go upstairs to the area where we can spread out a bit more. The Two Dancers, Mistress Natalie and I walk through the club to go up the stairs - I have my shirt completely off, and the plugs make me sashay through the club- Eva, the first dancer, catches my eye and I do the stripper move where I spank my own ass, I receive the wonderful gift of a laugh from Mistress Natalie. We get to the upstairs area, which has couches, and Mistress Natalie instructs me to dance for the girls - I do this for a few minutes, I have little rhythm but i do all the best stripper moves that I know: the aforementioned ass slap, some hip gyrations, I take off my belt and it gets wrapped around my neck in a slave collar and leash, my pants come down and the Dancers (and another dancer and her customer) get an eyeful of my thong, garters and stockings. I make my best effort to twerk and the bouncer suggests that I return my pants to the fully on position. (it wasnt a "suggestion" in the truest sense of the word) (It is only now, in retrospect, that I realize that I gave those ladies a dance and didn't get my tips....what a blown opportunity!) They then gave me a dance which was, yet again, exciting - Mistress Natalie Advised them that we needed to be going soon as we had dinner plans. Then the night took an unexpected swing - She told the Dancers and I that I was to be strapon fucked in the bathroom of the restaurant, and she covertly brandished a condom covered strapon from her purse. Uhhmmmm WOW! I think this is where I learned what "Subspace" means...I settled up with the Dancers and we took the next step in our journey.
We walked a few blocks to the restaurant- please remember I appear to be a preppy guy with the exception of my HOT PINK LIPSTICK AND MASCARA, and I am accompanying a statuesque beauty into the restaurant. It was a great place, Farm to table and GREAT, GREAT food. Mistress Natalie tells the person at the door that we are will sit in the casual seating area near the bar and I am a bit embarrassed after leaving that Strip Club Scene to head to a very vanilla and upscale restaurant. The waiter/bartender comes to bring us drinks, and Mistress Natalie again asks if there is something fruity with umbrellas and is replete with Sissiness- The waiter describes such a drink; Mistress Natalie points at me and says "she will have that, I'll have the Malbec" I hang my head, embarrassed, but I should have watched the waiter's reaction, proud of my sissiness. We had a great conversation over
dinner, mostly about diets and healthy habits- I am struck by the varied talents and discipline of this very Special, Talented, Creative and fun Woman. Her strength of character is truly to be admired, I feel lucky to get to know her a little bit. I excuse my self to visit the restroom- peeing with a chastity device on is not a good time and when I return, Mistress Natalie says, "Now you know why I choose this restaurant, they have unisex bathrooms that we can disappear in" then we continue with the conversation, but I am inwardly really excited and my head is spinning...also the sissy drink in this place was good, but I have no idea what it was. Dinner finished, I took care of the check and was led to the bathroom by Mistress Natalie, no real Mission Impossible stuff, we just kind of walked in together and she closed the door, directing me to bend over - she removed the plug, which felt A lot bigger coming out than going in, and began to use her fingers on my sissy pussy. I was a wanton slut wanting more but also trying not to be too vocal...Then the strapon came in, thrusting - I wiggled my hips to help it gain entry and I wanted it inside me badly, the chastity again restrained my surging, sissy clit and that moment when it slides in, balls deep, is heaven.... Mistress Natalie knows how to work a strapon in a sissy and it was wonderful, I was really trying to be quiet but I am pretty sure that anyone walking by would have wondered what was going on in there. This sissy only earned a quickie- all too soon she was satisfied and the strapon was withdrawn. "may I clean up Mistress Natalie?"
"No Slut, enjoy being wet". I am dismissed from the bathroom to get the next Uber to return to her Dungeon.
We have a good conversation in the Uber on the way back to the dungeon about how she built her dungeon. We return to her dungeon, she directs me remove my outer clothes, to sit on the central bench and the bell rings- there is a visitor. I look at her, she has a delightfully mischievous look on her face and says "who could that be?" My favorite smile is back! I am introduced to someone that enters carrying a bag, he is directed into he bathroom and a short time later Angela emerges, she is tall, blonde and outfitted in black lace. Mistress Natalie looks at me and tells me "you are in New York for only a short time, I wanted you to know what I am capable of" ....this woman is amazing!! She gives attention to the beautiful Angela and directs her to sit in a chair, My lipstick is upgraded to a beautiful, bright cocksucking red. I am directed to be at Angela's Knees. Her skirt is lifted and a big cock with a silver cock ring is exposed! Mistress lightly plays her fingers across it. Mistress Asks me to beg to suck Angela's cock - I beg, I want this, I want to make Mistress Happy! I am allowed to lick the balls, I gently tongue them, sucking one by one into my mouth. Angela compliments my style "he is well trained, Mistress...He is good Mistress"
Mistress Refreshes my lipstick, places a condom on the cock and directs me to continue- I lick up to the top and then swoop down until the entire shaft is in my mouth - I again receive a compliment on my blowjobbing and I show mistress at the base of the shaft, lipstick on the balls. i work hard up and down, up and down. stroking with my hands, teasing her ass and her thighs with my nails, i look into her eyes "cum you bitch"....Mistress has other plans- I am directed to get on the central bench, on my back as a sissy should be, Angela's balls go in my mouth - Mistress Natalie wants her to come on my new corset and she begins to excite my sissy pussy with her hands- I am moaning in pleasure and excitement, Mistress Natalie directs me to get my mouth back on the balls! I cant take it!!! My chastity device is full of a straining sissy clit. Mistress Natalie directs Angela to sit back in the chair and dons a big strapon cock- she strokes it erotically right in front of us, then she moves behind me and enters- again the feeing of resistance followed by that opening and the long stroke in .......I am moaning and cant contain myself- I see myself in the mirror with this goddess behind me- what a visual!!! Angela is looking on...i would be jealous if i were her...and then mistress Natalie withdrawls.....I am empty. Angela is allowed to place a set of lipstick marks on Mistress Natalie's upper chest (what an honor, I am jealous!!) and she is directed back to change back into her masculine clothes. I am still flying happy to be in her presence, but a bit frustrated....I am still locked up. I am instructed that I have been a good sissy (i couldn't be happier to hear those words) and that at 8:00am tomorrow, I will receive an email, giving me the combination of the box to get my key and unlock myself. With some time to come down and some comforting by Mistress Natalie, I depart. I don't remember the walk to the hotel. I do remember waking up many times during the night due to the restraining chastity. In the morning, I check my email,
and am instructed to release my self, my new favorite number is provided. I am instructed to cum on my panties, send a picture to Mistress Natalie and then eat is.........Ohhh that release was wonderful and arrived QUICKLY! I followed these instructions. I was told to send back the chastity device and key in the pre labeled box that she provided, but I needed to keep the lock unfastened and that I would receive instructions to buy my own chastity device to wear for Mistress Natalie which I could place the lock on, Knowing that she would be the only one that could unlock me......I cant wait!!!!!