Cisco’s Session

I had a blog reader who goes by the name of “cisco” write to me. He wrote to thank me for my blog. He is a young Canadian man in his mid-twenties. He described a bit of his previous kinky experiences (limited) and said he was considering booking a Pro Domme. He mentioned Mistress Violet as I so highly recommended her. Well happy to say that cisco got up the nerve to book a session with Violet, and I have permission from both parties to publish. Yay!

Mistress Violet Mays

I would like to bring you along a bit on cisco’s journey towards booking Mistress Violet, the anticipation, the preparation, and finally the scene itself.

Here is some of the correspondence that led up to it. cisco in blue. me in red, Violet in (what else?) violet. When I asked cisco to tell me more about his kinks, this is how he replied.

As for about my kink, i am fairly new to the whole world, although it’s something i’ve always known about myself. Even back to a young age i can vividly remember never being able to say no to a cute girl.

i suppose i’ve always pictured my “type” as the princess who uses her beauty to get me/men in general to spoil her. Although realistically 9/10 women with a dominant persona can probably have me on my hands and knees. I’m very into the idea of worship, being told to bow and lick a pair of heels or boots clean. i suppose i have a little fetish for them but more so the idea of being forced to degradingly worship a women is a major turn on. The idea of being at the other end of a whip is also fascinating but like i mentioned i’ve never experienced it.

i’ve considered seeing a professional dom the last year or so to experience a little more but haven’t been able to figure out the timing yet. Perhaps in the summer when my schedule lightens up i’ll schedule a visit with Mistress Violet Mays since she comes so highly recommended!

I really thought that if cisco has a genuine “first time” experience, it absolutely must be with Mistress Violet! I tried to do a little “sales job”…

I am picturing Mistress Violet “eating you up!” She is absolutely that dominant personality who GENUINELY enjoys what she does. She’s told me she loves first-timers… she’d have you licking her stiletto heels spotlessly, only question is before or after she sticks those heels into your balls and bottom hole ;-) She especially enjoys “deflowering” boys with her strap-on. 

cisco wrote back,

Hopefully she has mercy and it’s before!
(although i doubt mercy is either of your styles ;) )

i have no doubt she would eat me alive, she seems like an intelligent and powerful woman. But that would be what i’m looking for, the best way to try this out for real would be to be completely broken down and built back up as her’s. i imagine myself living on my hands and knees wearing a collar with a leash attached that she keeps tight and short, totally owned.

i can honestly say i’ve never dealt with anything remotely close to a “deflowering”, and it does frighten me a little. When i read your stories involving Adam i cringe just as much as i… get excited. But i have a feeling Mistress Violet has a power of convincing you that you want it from her, and if not that, then an ability to make you fear her whip enough to beg for it anyways. A power i imagine you with as well Mistress Julie.

Isn’t he just a nice polite boy? Is it not exciting that this is the correspondence that leads to his eventual compete surrender and deflowering at Violet’s hands? I responded to him.

With strap-on play it’s not the size of the phallus that’s important, or any pain. It can and should be pain free, until you want the pain, of course. What’s important is you being thoroughly penetrated and “owned” like a woman, by a woman, by means of repeated thrusts over an extended period of time. Once you are trained to the dildo you may want to show your devotion by requesting a larger dildo and struggling to take it, take it’s full girth and length, up your bottom hole.

Before taking it in your bottom, she would make you suck it, on your knees in front of her. Nice and deep in your mouth.

Then which would you prefer for your deflowering? On your back on the bed missionary style, knees spread and legs up, Mistress Violet fucking you from the front? Would she take her top off and bare her breasts as a treat for you? Maybe. Maybe not. Tilting her hips forward and back as she penetrates you. Or do you want it doggy style, head down and bottom up, Mistress Violet sliding it in from behind, holding you by your hips and thrusting into you over and over again?

Ha ha!

Oh, I know, I’m enjoying this way too much!

Yes Mistress Julie

While being owned is the objective, i feel like there is an inevitable bit of pain with a virgin asshole. And that may seem daunting but i’m sure that when i’m in the moment i will willingly accept it.

To be on my knees sucking on a domina’s dildo sounds both humiliating and exhilarating. Speaking from the other side, you feel powerful having someone in that position, to grab a fistful of hair and put your cock down their throat, being on the receiving end of that is one of the more certified ways of showing to who you belong i can think of.

That is also a tough choice, while i’m sure i’d prefer the view of on my back with Mistress Violet over me, the submissiveness from doggy style is also intriguing, being told to present my ass for her, maybe a smack or a crop if i try to shy away, i think i would go with that. Of course it is not up to me in the end, i’ll get in whatever position i am put in.

You have me convinced Mistress! (as if i needed much convincing, aha) i will reach out to Mistress Violet in a couple of weeks, i’m on my way to a resort so i’ll email her when i am back, but no doubt think about it the entire time. Should i mention you sent me along? Also i’d assume it’s more custom to use my real name with her? Since it is more of a professional transaction.

What must that be like? A young inexperienced super excited man-boy, getting up the nerve to book a session with a Professional Mistress where all his dreams might come true? I have no doubt he was thinking of it at that resort. What do you think, maybe even masturbating to the though of it?

I’m sure Mistress Violet will take good care of you and your virgin bum. Ha ha! No, seriously, nobody better for a first-timer. You may be nervous but there is no need to be. She will respect your limits while giving you what you deeply crave, and you will walk out with a gigantic smile on your face (and, possibly, a sore bum!), and eager to return.

Yes, please feel free to mention my name, and even to forward the email thread to her. Might be helpful for context. You should check her website for information on how to contact her and what her qualification procedures may be. I can assure you that she is utterly professional and very circumspect with any personal information she may require of you to keep herself safe.

That was basically the initial exchange. I was not sure if cisco would follow through or not. Sometimes nerves get the best of us! But right on cue, eleven days later, I received the following note from him:

So i booked my appointment with Mistress Violet!

i am very excited to say the least. We’ve discussed my interests and i forwarded her our email exchange and i’ve left the scene up to her. She knows i’m just there to learn and experience and i’ve told her i trust her and what she decides is best. (Already in the sub frame of mind lol)

As for the “deflowering” as you put it, Mistress Violet has informed me there will most certainly be one, but that it will be nothing i can’t handle.

I was so excited! I wrote to Violet right away that I heard, and she wrote me back thanking me for the introduction and saying that it was a very fun email exchange between him and I, and that she was tickled to read the exchange. I loved the “certainty” with which the deflowering will be taking place!

I wrote back to cisco next,

Oh goody!

Now tell me is there anything you crave that you left out of your discussions? Anything you were too embarrassed to ask for, or concerned that she might think you too weird, or you thought “too much” for a first time, or might offend her with the ask? Tell me ALL the things. ALL your most disgusting perversions! I will filter and “backdoor” (excuse the pun) what is appropriate, and you might get an extra surprise for your session… I know it’s expensive, so we want to make the most of it…

(this is fun)

Am I not being helpful?!? But it really was tremendous fun for me. I wanted to help as much as I could to make sure our shy first-timer got everything he desired. He wrote me back:

i’m glad i could be of some amusement to you Mistress,

i’m afraid that i do not exactly have any more perversions that i left out for Mistress Violet. I was very honest and general in my description of my interests to the point she suggested we cut doggy play to focus on broader topics so i could experience as much as possible for my first time.

As i mentioned to Mistress Violet i’m sure my interests (and limits for that matter) will mature and change as i experience more, but for now i do not have much practice to draw from. i find myself a little overwhelmed trying to come up with what i think is best, which is part of the reason i chose not to offer too much scene idea and to let Mistress do as she wishes with me so to speak.

That being said, what I do have are some more specifics as to what i would enjoy as i find myself thinking more and more about it. i had never thought much about being on the opposite end of a strap-on before, and i find i now think about it quite a bit knowing one is waiting for me. i think i’m much more in to being degraded than i had considered. The idea of simply being on the receiving end, ass high in the air for Mistress, while exhilarating, is improved upon immensely by imagining being in a tight collar, with a leash that she keeps short and pulls on to get me back on to her strap-on. To be verbally berated as her bitch or slave. Even before that to be on my knees looking up at Mistress with her strap on on and my leash in her hand maybe a crop in the other (i have a thing for a collar and leash as you can see).

And that degradation can be extended beyond my ass fucking. To be licking her high heels or boots clean under constant scrutiny at the threat of a serious whipping or cropping is another example of something that has been running through my mind.

i want to be completely broken down and owned. Whatever way Mistress finds works best to get what she wants out of me. Whether it be physical with a whip or crop, or mental with teasing and… words of encouragement (being called her bitch is something i keep hearing in my head). i would like to think of this as a training session in the same way Mistress calls it an introductory one, with her taking control of me by any means necessary.

i’m sorry i do not have more to offer that probably sounds rather to vanilla to you and Mistress Violet, call it inexperience, i’m sure i could think of more if i had more to base ideas off of.

What a clever and communicative young man. And hardly “vanilla” sounding at all! I was worried he would not be as communicative as he ought to be with Violet, keeping in hiding some deep dark secret, but it appears as this is one very well put together and clever young man, who knows that to make the most of the session he must be as honest and open as can be. His mind did seem to be focusing around a degrading deflowering as a central event.

I forwarded the above note “behind the scenes” to Violet, indicating I had “pried a bit more information out of our boy” and she should do with it as she saw fit.

Violet wrote me back,

oooh thank you Julie!!!
Degradation is a sexy one. Do you have any ideas for me?

Wow! Mistress Violet asking me for input! Despite all my carrying on and blogging about it, Violet is much more experienced than I, and every bit as kinky and creative if not more so. She is the pro to my eager amateur. I was very flattered that she asked for my input, and impressed that such a consummate professional was so open to and totally un-threatened by input.

As well, cisco wrote me back,

If you think of anything Mistress please feel free to relay it to Mistress Violet. i’m sure she would be happy to have your input and I know I would. You certainly have a better imagination for coming up with scenes than i do.

Anything you think i might enjoy based on our conversations, or anything you would just enjoy hearing about afterwards. Like I said, i’m game for quite a bit, i’m attempting to go in to this as open as possible to learn and experience

So I was definitely going to try my best to contribute! I wrote Violet back a cheeky “well, since you asked!” email with a bunch of random thoughts and ideas in it. Violet wrote me back and thanked me for it, joking that she should employ me to script my sessions for her and adding “very coherent and totally hot”. I felt like dancing the little Snoopy Dance garnering such praise!

The final production was all Violet of course, but I felt like maybe some of the things that were done were perhaps inspired from my note to her.

I gave cisco some feedback,

You’ll be happy to know that Mistress Violet and I have been in communication regarding you. She is very amused by you already, so you must have made a good impression.

He wrote back,

Hi Mistress Julie,

i’m very excited (and a little scared aha) for what the two of you are cooking up for me! i can only imagine the pain and humiliation probably involved when the two of you work together. My session can not come fast enough!

i’m glad she is interested! i would feel bad if i felt she was not having as much fun as i was during the session

One thing I know about Violet, if it’s kinky, and you are being well behaved, she is having fun!

Finally the day arrived! Immediately after the session, Violet wrote to me,

Dear Julie,

Cisco was a doll today. I gave him my full permission to write to you with all / any details as well as be completely honest in his experience with me. He told me that you’re the only person that he can talk to about his interests in BDSM, and that you have been very good to him. I applaud you!

Thank you for your assistance in the session today – on both ends!

I was so happy that my boy did me proud! He showed up and was a “doll”! Yay. My worst fear was that he would flake out and be a no-show. Apparently that happens with the young-uns from time to time. But he did show up and he made me proud.

I prodded cisco for his accounting, but it took him a couple of days as he wanted to write it all up properly for me, which I can understand. After he wrote, I checked with him if it was ok to publish. He responded,

You are more than welcome to publish my story Mistress! I had a feeling you might want to.

I then forwarded cisco’s account to Violet as well seeking her permission and asking if she wanted me to edit anything and if she had any comment to add. She responded,

Hi Julie,

This looks great! Absolutely post this on your blog.

My comment:

It is a very accurate portrayal of the session, and reading it transported me back to the moment. Playing with someone who is exploring and very new to BDSM is always delightful because everything is happening for the first time. Brain circuitry is firing and I can see how suddenly everything is starting to make sense. Cisco really got into licking and worshiping my boots which was such a turn on for me.

So without further ado, here is young cisco’s account of his very first time with a Professional Mistress!

Hi Mistress Julie,

Sorry it took me so long to get back to you, I wanted to do the story justice and kept getting pulled away from my laptop when I got going.

It was amazing! Mistress Violet is wonderful, so sweet you would never guess what she does for a living. Until she starts that is, then it is obvious she is very good at controlling men. I’m glad I was able to please her, I certainly thoroughly enjoyed the session and was shocked with how quickly it passed.
[“good at controlling men” – like an animal person might be good at controlling dogs, or horses – made me smile]

At first we sat and spoke for 5-10 mins just double checking on things, I was admittedly rather nervous. She checked my dos and don’ts and reminded me of the safe word and explained her scale of 1-10. 5 being something sort of hurts, 8 being it really hurts but I’ll do it for my Mistress, and explained that that’s the area in which we want to do most of our play. 9-10 is when something is too much. After this explanation she instructed me to go to the bathroom have a quick shower and crawl out naked on my hands and knees, to which I responded “Yes Mistress”
[Safewords and scales! So important for first-timers who don’t know what they can or can’t take – part of the journey is learning this – I love how Violet described the 8 – “really hurts but I’ll take it for my Mistress” and indicated this is where they would be playing. Yes!]

As I crawled out of the bathroom Mistress Violet was standing in the centre of the room, and I was instantly transfixed on her boots. I knew I had a thing for them but now I realize how much so. I stared at them as I crawled towards her. I must have been eager because Mistress instructed me to slow down, told me to wiggle my hips as I slowly crawl towards her. She had me follow her in a circle around the room, then told me to bow to her. She had me put my forehead on the floor and raise my ass. then arch my back and push my chest closer and closer to the floor. She explained this is the position that she likes, and I can understand why, it put me in such a submissive mindset I can imagine as a dominant it does the exact opposite. She circled behind me and spoke of how exposed I was and how she would be taking my anal virginity, then Mistress pulled my cock between my legs and instructed me to close my thighs together. She explained that that was her cock, and her toy, with which she could do anything she pleased. I simply stammered “Yes Mistress”, I was still nervous and was experiencing a deeper sub mindset than I have before. (My inexperience comes out a lot in this session).
[I love the submissive position – genitals and bottom hole on full display, the reminder about the central event to build the anticipation.]
She then walked back in front of me and I stared at her boots again. She grabbed a fistful of my hair and said “You’re gonna be my bitch today, aren’t you?” and I replied “Yes Mistress” “Say it” She said, and I said “I’m going to be your bitch today Mistress” She then told me to ask permission to kiss her boots, and I very heartfully asked “Can I please kiss your boots Mistress” and when she allowed me I lowered my head and kissed what I had been waiting for since I first crawled out of the bathroom.
[There’s the “bitch” word trotted out. Violet makes note of requests like that! I like how he was made to repeat it. And I like how long he had to admire Violet’s long legs and kinky boots before being allowed to kiss them.]
Eventually Mistress grabbed my hair again and pulled me back up, she asked me, “do you feel owned?” and I said “Yes Mistress” and she said “But how can you be owned yet” and she turned to grab something from the counter, and turned back with a collar in hand. I bowed my head as she put the collar around my neck and then she attached a leash to it and explained that “now she owns me”. She instructed me to get in to a puppy position, with my paws up. I did so and then was told to raise them higher. Then she told me to give her a yelp, and I did my best puppy bark.
[Ha ha! Got a little puppy play in after all, including the collar and leash. I don’t know if Violet was intending to anyways, but in my note I indicated that he seemed to have a strong fixation on collar and leash.]

Next she told me to get down and lick her boots clean. I instantly dove to her boots and passionately licked them all over, from the toe to the top of her thigh. I never thought about how how dry your tongue would get licking leather boots, but I was not going to let that deter me.
[Finally allowed to lick them thoroughly! And yes, he actually paid for this :-)]

After a bit of this she led me by my leash up the stairs to the bedroom. Mistress told me to get back in my bowing position and explained that she calls this position A. She walked back around me and told me to stick my cock back between my thighs. After I tucked it back in she started to smack my ass, balls and cock with her riding crop, because that was “her toy that she can do what she wants with”.
[Oh no – delicate cock and balls being whipped with an instrument designed for a horse! Thought it a good time to add one of Mistress Violet’s photos…]

Next Mistress got up on the bed and sat at the head of it, she called me up and had me lick the bottom of her boots and clean them again. I can’t even tell you how long this went on for I was too focused aha. During this Mistress proceeded to kick my cock with her heel, which is how I learned how truly sensitive the head of my cock is. Eventually Mistress called me off, she removed my leash and told me to lie on the bed. She restrained my wrists and ankles, spread eagle on the bed. At this point I asked Mistress if we could pause because I thought of something I wanted on my definite no’s list, anything in my cock head (I had never even thought about even the idea but with my sudden realization of how sensitive it is I was definitely against it, and Mistress assured me that’s more of an advanced thing that never would have happened without being previously discussed.) Mistress then kindly folded my foreskin back up realizing I was uncomfortable with too much pain there and probably knowing I wouldn’t be bale to take what was coming next if it made contact.
[Ha ha – a cute “first-timer” moment – silly boy!]

She proceeded to put nipple clamps on both of my nipples while checking in on me that I was not above an 8. Next she blindfolded me and started to attach clothes pins to my balls and cock. She placed the first one and then asked “Where do you think the next one will go” and I responded “Anywhere you choose Mistress”, because I think I genuinely would have let her do just about anything to me (that I could physically handle) at that point. She connected all the pins with a string and told me how what is called the zipper works, if one comes off they all do. She proceeded to place her stocking covered foot over my mouth and I kissed feverishly as she pushed her foot in my mouth and then stepped on my balls. Next Mistress climbed off of me and grabbed the whip you warned me about and I had feared for the past week. She gave me a few lighter whips and gauged where I was on the 1-10 scale, going up until she found an 8. She proceeded to remove my blindfold and the image of her standing over my tied up body holding that whip is something I’ll probably remember for years to come.
[I think Mistress Violet deliberately sets up “visual tableaus” – it is her art, after all. Also nice to learn how a pro gets the intensity just where she wants it.]

Mistress then began to whip my stomach and seemingly relished in the pain she was causing me, which in turn aroused me even more, although the whip made sure my cock did not show it. The pain of the whip on my bare stomach I could handle but when it made contact with my cock or the clothespins is when I reached the levels of 7 and 8, I’m sure this was Mistress’ intent though. After enjoying whipping her new bitch Mistress then ripped the clothespins off of me and they all came up with one pull, this is when I let out my first shriek of the session.
[“First shriek” – oh be-still my fluttering heart!]

After this Mistress untied me from the bed and told me I was going to put her strap-on on for her. I got off the bed and on my knees and helped her step in to the strap-on. At first I was so nervous that I missed one belt loop which resulted in a firm smack in the face.
[Oh! I was excited reading that – that was one of my suggestions! I was imagining how nervous he would be fumbling with a (quite complex) strap-on, and trying so hard not to “get fresh” with Mistress Violet when in such close proximity… nervous fumbling resulting in immediate chastisement!]

Mistress then presented me with two dildos and allowed me to choose which one she would use. I chose the smaller one and in hindsight am very happy I did. Mistress then told me to get back up on the bed on all fours facing the end where she stood. I was instructed to suck on her strap on to prepare it for entering me. This is where I found out how bad of a gag reflex I had. At first I attempted to direct it in to my cheek but Mistress would not allow that. I always knew I had somewhat of a gag reflex but this being the first time I’ve ever actually tried to stick anything down my throat like that it was a big awakening as to how bad at this I was. We tried 3 positions of dildo sucking and I definitely did my fair share of gagging but ultimately could not suck on Mistress’ strap-on very well.
[It’s not about about how well you do it. It’s like the talking dog – the point is not how well it speaks, more that it can speak at all. I love how he was “not allowed” to hide it in his cheek! We know your little tricks, boys.]

So from here Mistress instructed me back up on to the bed in position A, and then she pulled me down so I was standing on the edge and bent over (this must have just been a better angle for her) She lubed up my cock and began loosening my virgin asshole. She then set the goal of 10 good strokes, all the way down to the hilt, and that would be after the warm up. The sensation of fingers alone in me was something I hadn’t even experienced before and both that and Mistress’ strap-on were strange. Mistress checked on me several times and that’s the only way I could describe it. It comes in waves almost, any time she goes deeper than before there’s a weird feeling, a little pain but not much (remember I was using the smallest dildo possible) then you get used to that level and she would go a little deeper, and you’d go through the same thing again. Then Mistress began really fucking me, and I now understand what you meant. It’s not about the pain like other acts, it’s about submitting to her. Mistress got her 10 good strokes in and asked if I could continue and I said “If she wanted to” because I genuinely wanted what she wanted, the act of a dildo in me did not feel good, not terribly bad, but not good, and yet I would continue for her. I enjoyed the thought of her behind me with her one heeled boot on the bed, owning me. Mistress instructed me to look at myself once in the mirror and the image of her behind me was powerful.
[Another of her tableaus! I love “the goal” of 10 good strokes all the way to the hilt. Almost more humiliating to be “checked-in” with so often – like a virginal bride on her wedding night fucked by her sensitive and much more experienced newlywed husband.]

Eventually when it was done Mistress cleaned me off, climbed on the bed and called me back on as well. She said “now I’m going to train you to cum on my boots and clean them off”. I again went to town worshiping Mistress’ boots, licking and kissing them all over. At first it was difficult to bring myself to cum, I had just been fucked in the ass after all, I was humiliated and a little sore. So I decided to lean in to it, I requested Mistress degrade me a little more, to which she happily upped the domme persona. She grabbed me by the hair and forced my tongue along her boot. She verbally abused me calling me her bitch who couldn’t even suck her cock properly. Claimed that if I couldn’t cum she’d just lock me in her shoe closet and have me clean all of them with out paying any attention to me, she spit on me and humiliated me, and all of this brought me to the edge (I will definitely hope for more of this style next time). Mistress presented her boot to me and I came all over the left foot. She then instructed me to lick it, and while I wanted to obey Mistress I simply couldn’t get it all down. I did take 3 licks though, the last two only on Mistress’ insistence, much more than I would have done otherwise. I gained much respect for every woman that’s ever swallowed my, or any own else’s, load. I then cleaned Mistress’ boot with a tissue and apologized as I did so. When I was done I was instructed to crawl back to the bathroom, shower and get redressed.
[Ok, well that was a poor showing. Some one would argue he should have been made to lick it all up. But yet another example of Mistress Violet being in the moment and reading the situation. When is it too much? Need to keep it at the 8 level. He’ll be licking it all up soon enough. I love the “upped domme persona”, especially the spitting on him. Reading that turned me on. It’s not something I’ve ever done to my husband – am now considering it!]

And that was it, we chatted a little after about the experience, had a glass of water, I asked about future correspondence and I was sent back in to the world.

I’m sure I have a few details wrong here and there, it was all mesmerizing in a way, the hour and a half felt more like 30 minutes looking back, but I think I did a pretty good job of recalling it, Mistress Violet might have a more accurate recounting of the session.

Like I said it was a great experience, I’m so happy I tried it out, and will definitely have to again at some point.

Yours,
cisco

It certainly shines through what an incredible professional Mistress Violet is. She hit the notes for cisco so perfectly and clearly enjoyed herself doing it. All the communication beforehand, the checking in during, the adjusting of the intensity, and the stretch goal setting to take cisco right up to where he felt comfortable, and then just a little bit past. Violet’s ability to “up” the domme quotient at will (and I can imagine her smile as she is asked to!).

What I’m really impressed with is that she is equally as adept at domestic, medical, complex roleplays, and no doubt whatever else strikes your fancy. She is my inspiration! So fit and beautiful, so intelligent, so experienced, so in-tune emotionally, so professional in the best possible meaning of the term, and so darned kinky (I’ve said it before – if you think you are pretty kinky, Violet is kinkier!). Blog boys (and girls), if you have the opportunity, you should definitely book a session! This girl certainly has a crush on her!

And cisco, thank you for being such a brave young man in realizing your fantasies and allowing us to share them and live vicariously through you (now I have a fantasy of being a boy-man put through my paces by Violet!)
Source: Strict Julie

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