Former Junior Manager to be Spanked by her EVP!

Oh, how naughty is that? As described in Yikes! outed..., a now-retired Executive Vice President at a firm where I was under him as a lowly junior manager has put 2 and 2 together and recognized me from this blog and reached out. As it turns out, he is a fan and an experienced top-preferring switch himself. He bears me no ill will, and is not in any way coercing me (my secret is safe with him). However, he did ask after the possibility of a hotel room spanking tryst, and I have agreed. What will it be like to be across my old boss's boss's boss's knee???

He's an older gentleman, mid-sixties, mostly retired. He was very successful in the corporate world, and one of the smartest and most accomplished people I have come across. He was a real inspiration to me, and he took me under his wing a bit during a few-week special project where I was directly assigned to him. He was also instrumental in securing me a promotion which eventually lead to other opportunities for advancement there and in other companies. So yes, he is totally a "Daddy figure" to me, and is about the same age as my Dad.

I have agreed to meet with him not because he discovered me, but because I have such high regard for him, consider him a true Daddy figure, and get totally hot thinking about an encounter with him. Also, because he accidentally discovered me, he sees me for the sexual person I am in the way few people in real life do. As well, he is a very experienced older male top, and I have not had an encounter with that at all (David doesn't count, we came up together that way, this will be a new perspective).

We had a very productive series of emails negotiating the scene. I have found that newbies are not good at negotiating their scenes, and this is a learned skill. I'll share our negotiation here, as I think it may be instructional.

Here was my opener when I still had not completely made up my mind.

Hello "Mr. Stevens",

Thank you for dropping the comment on my blog.

I am leaning towards allowing you to spank me. Can you tell me a bit about your experience and your approach before we decide to proceed and how to engage?

Thank you,

Julie

"I am leaning towards allowing you to spank me". Ha! Who was I fooling? And what a ridiculous concept when applied to my ex boss's boss's boss! He replied.

Hi Julie,

How delightful!

I would call myself a very experienced top and bottom. I have been seeing professional dominatrices and submissive for over 30 years. At least every couple of months or so, so something over, what 180 such sessions? I traveled extensively for business, as you know, and had experiences all around the world. As well, I had a younger female play partner (a "sugar baby") whom I very consensually spanked and dominated for a couple of years every couple of weeks.

My approach is to meticulously discuss boundaries in advance, and to always play with a safeword, which I would respect completely and immediately.

With a new play partner, I would generally keep it slow and light to learn her body's reactions, and check in frequently. After several sessions we could go harder.

Please let me know, as explicitly as you can, what your boundaries are, including what kind of sexual touching you are comfortable with, and what types of implements you would want used on you (if any - I am told I have a hard hand when I want to).

Looking forward hopefully!

Mr. Stevens

Very nice message back! I was impressed. First off, experienced indeed, and with multiple different play partners. I was like a babe-in-the-woods by comparison. He kept a Sugar Baby for a time as well. I'm jealous! I love that he raised "boundaries" and "safewords" right off the top. I appreciated the "slow at first" and "frequent checkins", but given there may not be a second time, I was going to suggest we play with a yellow safeword as I would explain. I liked that he has a "hard hand" when needed. Loved the toppy confidence. Men take note: if you can't master us with just your hand, hit the gym.

Here was my reply. I'll annotate in red my reasoning

Sounds like we are very compatible. And you have an impressive resume, I must say!
I was impressed by his experience level, and somewhat turned on. I have never played with such an experienced male top. Wondering what that energy would be like.

I have discussed it with my husband, and I have decided that I want you to require me to show up at your hotel suite for an embarrassing spanking for posting such lewd material on my blog and risking exposure for my husband and myself.

We will start off that way the moment you open the door to your hotel suite. No pleasantries or conversation beyond what would be up in character. Straight to the punishment. You shall be you and I shall be me. I am being compelled to show up or risk exposure, but I know deep down I should be punished.

After we have played out the scene, we will break character and have a chance to chat, perhaps over a nice bottle of Champagne and some caviar you will have acquired in advance?

Yes, my husband and I discussed the scene and my boundaries fully in advance. He is excited that I will get to play with a real Daddy figure and such an experienced player in Mr. Stevens. David honestly does not have a jealous bone in his body. He knows he's my real Daddy and I will always come back to him. I'll explain in a subsequent blog post what was shared with my husband and when.

I thought it would be fun and break the ice to go directly into scene. He will pick right up as my old EVP, and me one of his many junior managers. I am still working for him and he discovers my blog via a report from IT. Either I submit to discipline or I will be made into a public disgrace. The discipline is for my own good. I am being punished for my reckless, lewd, and lascivious, online posts in my spare time, and worse still, while on the company's dime!

When playing a scene, it's best to just say what you want as part of the negotiating process. If your partner is not comfortable with that, they can come back with a counter-offer.

I dropped in the "hotel SUITE", Champagne and caviar. We are not playing at some Motel 6! I know Mr. Stevens is well off and can afford whatever. I shall be judging him based on the cost and quality of his picks ;-) I may be a total whore, but I am not a cheap one.

I expect we will do this once and once only. I hope that is ok.

Key word: "expect". I wanted to set the expectation that this is a one and done. I am not seeking the entanglements of a regular play partner. I have my husband as that in my life, and he can scratch my Daddy itch as needed. So regardless of how amazing this experience may be, I "expect" not to repeat. But, I leave open the possibility of an occasional repeat. I guess we'll have to see how nice a hotel suite it is, the vintage of the Dom Perignon, and the quality of the Beluga. Ha ha!

[P.S. is it not weird that Mr. Stevens will be reading this? I'm writing it as if it was between me and you blog readers - but I know he will read of course. Surreal.]

Regarding boundaries.

• you will be well-dressed, clean, fingernails clean and cut.
  Of course I expect nothing less, but best to be explicit. Will keep him on his toes as well.
  
  
• I am presuming you are vaccinated and not subject to any quarantines? Please confirm. Regardless, if you feel any symptoms, we will call it off and reschedule. And likewise for me.
  Yes, there is still this tiresome plague out there. At his age he is way more at risk than me, so I wanted to be sure he was protected.
  
  
• up to and including full nudity for me is ok
  Mmmmm. I enjoyed writing that. No need to be tentative with me Mr. Stevens. Unwrap your gift fully. Be explicit. Say what you want. Let's make sure there are no misunderstandings. He may not be comfortable with fully stripping me, and that is fine, it's not up to me. But this does say I 'kinda want it, right?
  
  
• fondling of bare bottom, bare breasts including nipples, private parts (vagina and anus) and light digital penetration ok without gloves.
  Yes, being handsy is ok, you will not offend me. Let's not waste time like teenagers bumbling through a first date. Boundaries. THIS is ok. THIS is not ok.
  
  
• deeper digital penetration ok, but only with medical gloves (any kind, please supply).
  I guess for a bit of hygienic reasons. If I'm going to be roto-routered, I will want some protection up in there. My pussy is quite sensitive. And he may not be comfortable doing that to me without gloves, so I am saying ok to that.
  
  
• I will bring lube and two dildoes with me, the larger for my mouth and pussy, either order, back and forth ok; the smaller exclusively for my bottom hole; should you care to use them. Be gentle if you do. Lube for the backdoor, none required for my pussy (which assumes you are being sensitive).
  If sex toys are going to be used on me, I prefer bringing my own because I know where it's been and how it's been cleaned and cared for. The mouth/pussy dildo will be the same one I acquired for my tryst with Mistress Violet during that "outing" episode. Seems fitting, no?
  
  
  
  
  
• do not spit on me at all. You may make me use my own saliva on my dildo, however, as pussy lube.
  We are going to stop short of exchanging bodily fluids for pragmatic health and protection reasons. It's not essential to the scene.
  
  
• hand spanking to warm me up - I like OTK.
  I need a warm up or a real spanking is too excruciating. If you want to really punish me, long and hard, you need to warm me up. Some spankers don't go OTK by default. For my Daddy vibe I want that for at least part of the time.
  
  
• can escalate to an intense hand spanking,
  He did mention he had a hard hand. I would like to experience that, please!
  
  
• may continue with a light paddle I will bring.
  I'm going to bring the Muskoka paddle. Very stingy without the bruisy bits.I had better be in tears before my paddling is over or I shall lose all respect for my geriatric mentor.
  
  
  
  
  
• may continue with a flat leather dress belt you wear and remove - I like being bent over but comfortably supported during a belting.
  A big fantasy of mine is Daddy taking off his belt. I want it to be his belt. I hope it is a solid but supple expensive calfskin dress belt slithering out between the belt loops of his dress trousers. I don't like the "stand in the middle of the room and bend over" position. I like wriggling and kicking during my spankings, not holding still.
  
  
  
  
  
• gentle spanks to intimate areas are ok
  Yes, pussy, anus, breasts. Up to him to interpret "gentle". Don't whip the shit out of me, but don't make it a joke or a "sexy" thing either. Punish me.
  
  
• my safeword will be "red". If used we stop immediately and step out of character immediately. I'll consider it sexual assault if you do not respect this.
  Brought out the big guns here! This is the key, key, override that all players need to have at all times. I used "sexual assault" to convey how serious I am about absolutely respecting the safeword. No "one more hit". You stop!
  
  
• given this is a first meeting, I will reserve the safeword "yellow" as a slow down safeword. If I say yellow, you don't need to stop, just be aware that the activity is too intense for me, and back it off a notch or two. When I am better warmed up, that same level of intensity may be more tolerable, so don't consider it an absolute.
  I encourage all players new to each other to use a yellow safeword. So many encounters are either too hard or too light with both parties groping towards the right answer. Using a "yellow" safeword solves that problem instantaneously. Yellow should never interrupt the scene, just steer it a bit. It also makes "red" much more meaningful.
  
  
• no need to be overly gentle with me. I'll consider it a disappointment if you are. I generally crave a real punishment, to tears. If I beg you or demand you to stop, you are safe to ignore. Those are not my safewords. I'll try to keep it down for the sake of adjacent hotel guests, but no guarantees ;-)
  This was in response to his "slow and light" and is coupled to the "yellow" above. No, I want a real spanking. I will be in tears before I say yellow. Also, with players new to each other, a loud "No!" or "Stop!" can be misinterpreted even with safewords. I wanted to make clear that I will likely use words like that as part of my headtrip, and they are to be ignored.
  
  
• no sexual intercourse, vaginal or anal, and no going down on me, including no annalingus. No swapping of bodily fluids at all. No kissing. No breast suckling.
  So I decided no intercourse, with or without a condom. I feared if I left that possibility, it may become the focus of the session, which would be a missed opportunity. Again, mostly for safety, no swapping of bodily fluids.
  
  
• you may require oral sex from me, but it must be with a condom. Feel free to use the belt on my bum if my blowjob proves to be inadequately skilled, I am used to it :-)
  I think this is part of how an EVP may punish a junior manager, no? A good, long, hard, saliva inducing, mouth fucking? Teach her her place. My lips may tire, and he may get a nip. He knows what to do if that happens. The belt and then back at it until I am trained to look like a sex doll after he pulls out... Daddy!
  
  
  
  

Sorry for being so strict and explicit. I hope it is not a turnoff. Please let me know explicitly if all of the above is ok.
I am hoping it's not a turn-off. Was not for me writing it!

After our scene it will be great to sit and talk and reconnect, and maybe swap sexy stories. I'll likely be sitting on your lap, scantily attired, Daddy.
I think I have this thing about sitting on distinguished older gentleman's laps. Feel free to fondle, Sir!

If you're still frisky, I'd be happy to take you over my knee for a genuine "Strict Julie" experience. I'll pack my strap-on as well in case you wish to experience that. If you haven't blown your load into your condom when in my mouth, I'll give you a "happy ending" to our encounter, ON CONDITION you let me feed it to you after and you swallow down every last drop under my watchful eye. You know my rule. Ha ha!
I was hoping he would go for that. He did mention the possibility. I have no trouble at all switching roles. I think it's healthy and a great way to really get to know your partner. It would be fun fucking Daddy's ass. Or fucking the EVP's ass! Take it! I am offering up a handjob. There may be a ruined orgasm, and there may be an extra minute or two of cock-rubbing after orgasm... we'll have to see. But if we switch, and if he cums, that last is utterly non-negotiable. :-)

Assuming ok, let's set a date and time convenient to you. And of course, all of this will go on my blog.
I'm not asking anymore, I'm telling!

Excited to play,
I truly am.

Julie

My point is, when negotiating a scene, just be as clear and explicit as you can. Don't fumble around there. He responded. My thoughts again in red.

Hi Julie,
 

I'm bowled over. More than I ever dreamed of when I reached out. Thank you so much for granting me this amazing privilege.
I like that he keeps reassuring me I'm in the driver's seat. Every time he does it, I feel an extra layer of resistance peel away.

Just for complete clarity, while we may be roleplaying a bit of coercion and a bit of chastisement for what you have done and the risks you have taken with your blog, I wanted to emphasize that there is in fact no coercion whatsoever in my mind, implicit or explicit, and as far as I am concerned you are of course free to change your mind at any time (I know I don't need to presume to tell you that). This applies to meeting at all and/or details of any of your stated boundaries should you reconsider any. Your secret will be safe with me regardless of a cancellation or anything else.
More of the same. Appreciated.

In terms of a bit of scolding for your lewd behaviour, That will have to be an act, as I applaud your kinkyness and freeness. With regards to chastisement over the risks you have taken with your blog, well, I confess I may genuinely have some of those feelings, stemming from a fatherly feeling of protectiveness towards you, which can be "channeled" at our meeting in a manner that will result in a very red bottom for you!
Ok, that's good. Getting into the spirit of it now. I genuinely believe he feels a certain protectiveness towards me. While I consider him a Daddy figure, I have no doubt he considers me a daughter figure. I like that he will be bringing some of that real emotion to our scene. For my part as well, I feel guilt for exposing my husband and myself to discovery. I could do with a genuine guilt-mediating spanking for that.

Mind you, these feelings were completely overcome by my desire to read your blog, view your delectable photos and videos, dream about what I might do with you were you mine for an hour (apparently dreams can come true), and all this despite feeling this was all somehow "wrong" at some very deep level. Perhaps after our chat, you can use this conflict within me to give me my richly deserved punishment, as turnabout is fair play.
Oh yes, perfect pretense to switch, and a real one: pervy Mr. Stevens perving after his pretty young junior manager!

I very, very much appreciate the clarity and precision of your boundaries. In them I see again the promising junior manager I knew all those years ago, destined for much bigger things. They also speak to a highly experienced player who knows what she wants and how to get it while staying safe.
He responded positively to my explicitly stated boundaries, and likes the way my brain works. That's a turn-on for me.

I read and understood all of your boundaries clearly and will abide by them. I will be the cleanest I have ever been in my life, and will be sure to wash behind my ears, Ma'am, so to speak. I like your use of the "yellow" safeword and appreciate that it's for both our benefits in terms of fine-tuning the intensity. I can confirm that I have had the first dose of the vaccination about a month ago, and am not currently subject to any quarantine and will cancel if I develop any symptoms prior to our meeting or if I must quarantine due to contact with others before our meeting.
Repeating things back for clarity. Good. He's taking a submissive tone around the cleanliness thing. Nice. He was not offended. He's using it to signal that the woman is in charge here, regardless, as we ultimately must be in any intimate encounter. And by "behind his ears" he means his cock. balls, and anus, for you slow people. :-)

Just for clarity, I am assuming that your boundaries are also guideposts of your desires during our encounter? Please confirm.
Indeed they are! No reluctant bride here.

I would say that my boundaries mirror yours almost exactly. And when it is my turn across the knee I too will use your yellow and red safewords. My desire and ability to take a hard spanking has for some reason declined over the years, so I would prefer a medium intensity as opposed to the delightfully punitive butt whacking (though lovingly administered) you seem to be in for.
That is good to know in advance. Our purpose is not to actually punish one another. Our purpose is to play and seek mutual enjoyment and gratification. In my case, that involves a punishment. In his case, it does not. Very cool with that.

My boundaries are the same as yours with regards to sexual contact, but would extend to allowing a kiss or a breast suckling if allowed while you are on top. I will not initiate either of those, however, and have no expectations of you doing so. Just clarifying my boundaries.
He's letting me know his boundaries are a bit past mine. So if I choose to extend mine, I will not be busting his. This may have earned him a kiss and a breast suckling during his handjob. Say what you want. It's a fun negotiation.

A further boundary for me would be in the pegging department. I would welcome that for the full Strict Julie experience, but without the infamous "Adam". Is 3/4" diameter acceptable? If ok, I will bring that modest toy.
Ha ha! He was worried about Adam showing up to join the party. I am glad he will bring the size of dildo he is comfortable with.

As I alluded to, my wife does not know about my BDSM life, bless her heart. We have tried, but she is so not "into it" that I have given up any attempts in that direction and play the vanilla husband for her benefit. I judge from your responses to blog comments that you consider my case to be a "hall pass", for which I am eternally grateful.
This was the subject of some debate in the comments to the last post. I do think in this situation is ok. People need an outlet for this stuff. I respect if your opinion differs from mine in this regard. I see it like kids at play as opposed to an extra-marital affair.

But, as a consequence of the need for a certain degree of discretion, it is awkward for me to get out of the house right now, with all of us supposedly on "stay at home" order. I would need a good excuse for my wife which is hard to come by. Perhaps after stay at home is lifted, then a downtown socially distanced board committee meeting might be a good excuse? Are you able to do a 2-5pm sort of weekday timeslot with a week's notice? I suppose it will have to be June, unfortunately (we typically spend July/August up north).
I get it. Hard to slip out without an excuse. I am at his disposal.

Very much looking forward to our torrid tryst. The Champagne and caviar will be first rate, as will be the BDSM play, I am sure.
Glad he didn't miss that part ;-)

Still pinching myself making sure I am not dreaming this,
Nope! It's real!

Mr. Stevens

I wrote back briefly,

Yes indeed, those are my up to and very including boundaries, and do represent my hopes for the scene. Feel free to not go that far according to your comfort level and desire.

And I will give you the mild version of the Strict Julie experience, as requested. Ha ha! Just get that yellow safeword ready, Sir, for that tender backside.

I understand regarding the stay-at-home and the difficulty for you to step out. The anticipation will be lovely. Let me know when you can work things out.

Julie

Looking forward to it for sure now!

What do you think, is Mr. Stevens a lucky duck, or what? If you have suggestions for what Mr. Stevens should do to me within my boundaries, please suggest in the comments!