Cougar relationship

Her imagination has been working overtime this past week. We just returned from a trip Saturday afternoon. I woke up Sunday super horny and started trying to turn her on hoping to get out of chastity but it didn't work. All it did is turn her on more to want to get me into the playroom... By mid-afternoon, it was becoming hard for her to ignore her hormones.

On the flight home, she got all excited explaining how she plans to begin taking her role in the playroom to a different level. Something about me showing her respect by calling her ma'am and responding yes ma'am turns her on? On the flip side, I am to never call her ma'am outside the playroom. I just shook my head with a grin in amusement. You do what you have to do darling.
She smiled.

I figured whatever, let her have her fun. What is she going to do edge me? She is this vanilla hot woman who acts totally normal in public but put her in the playroom and she turns into this sexy dominant wild woman that will tie you up and tease the hell out of you for her own enjoyment.

It's actually cute so I went along with it. Seemed simple enough. Sort of turned me on just a little too. She is so cute and bubbly when she gets excited about this stuff, it's really hard to say no.

Sunday afternoon, I got greeted at the door of the playroom and she always looks so freaking hot in her leather and thigh-high boots. She wrapped her arms around my shoulders and gave me a big wet kiss pressing her breast into me. My dick tried to get hard in its cage. Kissing me passionately she stopped, looked at me, and smiled saying welcome to MY playroom. Oh it's yours now I said.

Yes, it is she smiled. Come on in let's play.

Okay.

It sound like she said: one?

Would you like some more of those kisses? YES, I didn't even hesitate.

two she said.

I grabbed her pulling her close to kiss her. Uttt... not so fast. As usual, I could see, she had picked out a number of items and had them sitting on the bench when I came in. Take all your clothes off right here.

Good boy now... Come with me. Close your eyes. Close them tight. Don’t cheat keep them closed. She grabbed my hand and led me into the room. She said no matter what do NOT open your eyes.

Okay.

She said three!

Three what I asked?

She said four!

l laughed four what? What are you doing?

Five and Don't open your eyes and don't move she said...

I felt her soft lips kiss on mine as she said Now DO NOT open your eyes until I tell you she said sternly.

Okay, I said.

Six, she said.

I immediately felt something on the top of my head as it quickly lowered over my face to my neck.

Don't move and keep your eyes closed she said

I uttered something don't even remember what and she said seven.

What the hell is she counting it was throwing me off.

This is close without the padded eyes...
https://sadolair.com/products/copy-of-leather-hood-breathing-grommets-only?variant=18360636549

Ann: what the hell are you doing to me I laughed...

Eight, just relax I am almost finished. By the time I went to open my eyes my head was fully encased in leather. There was nothing over my mouth. I got distracted by the smell of the leather for a few moments. I love the smell and feel of leather as I took a deep breath through my nose that had a couple of holes in it to allow breathing. I am realizing now that the eyes have some kind of padding over them pushing my eyes shut. Probably because by now she had tightly laced it. By the time I figured out what was going on I feel her pulling something around my neck.

There she says. Good boy.. How does that feel.

Ann, what are you doing? I raised my hands to feel around.

She kept adding to the counting.

I feel her soft wet lips press against mine giving me a kiss and disappearing. I can't see a freaking thing.

Ten, she says immediately saying GOOD! You shouldn't be able to see anything... That is the whole idea darling. Now I can keep you inside your own head letting your senses toy with you while I toy with your sexy body.

I try to find something a seem or anything over the eyes to try to pull back and there is nothing to grab onto. I try to move my head around trying to find some light but I cannot even open my eyes with the soft padding pushing on them. My dick pushing hard inside the cage. I grab my crotch and try to shake it a little to get some relief.

Having a little trouble sweaty she giggled?

I Reach up again to feel the hood. The leather is soft and smooth. I hear her heels clicking around. I reach around the back, tracing the laces down to a collar straight to a padlock. You have to be kidding me. I tug on it. I rub my hand around feeling my mouth and down the front of my neck over the collar.

did you lock this on I asked?

11 yes it is. I know you wouldn't try to do this but it's there just in case someone would try to take it off without permission. She giggles.

Here now let me help you put these on I hear her say. She grabs my hands and I eventually figure out she is helping me put on high heel boots. They are not the ballet boots thank God! She puts my hand on a zipper to zip them up while she pulls them together tightly around my calves. I don't even know which ones these are I can't see anything but they feel good. I hear her heels clicking around again. I cross my leg over the top of my other one and reach down to feel the heel. It feels like 5 or 6 inches. I feel the leather around my leg.

How high are these I ask?

She had continued counting up during our conversation. I am slightly distracted trying to figure out what's going on as she says you do realize you have disrespected me since you walked into this room.

What are you talking about I laughed? I did everything you asked me to do.

I told you on the plane that I wanted you to respond Yes Maam when you come in here....

Oh, yes you did say something like that.

38.

Yes, Ma’am I jokingly reply with a laugh.

Is that sarcasm I hear?

She kisses me again.

Now jump down she demands.

How do your boots feel she asked? Good, I guess.

She is now at 39,

This is bizarre.
I have no idea what you are doing Ann

I went to sit back down on the bench.

40, OH... no, no no... she says stopping me.

What, I asked?

41 you Just stand right there for me.

I leaned against the bench feeling how good the heels felt right now. They had some kind of padding at the balls of my feet. I started to realize how helpless I was without my sight. Everything is so much more impactful with this hood on.

She grabbed my hand saying come with me. She turned me in a circle and I had no idea which way we were walking in the room. She said step up helping me as she guided my leg where she wanted it, good boy. Now your other one.

I felt something now confining my ankles. I could not move them in any direction. They had been locked into position, They were now spread out about 3 feet or so. She grabbed my hand pushing on my back telling me to slowly bend forward grabbing the lock on my hood to move me into position pushing my neck down while adjusting my wist.

She sternly said DON"T MOVE! I don't want to hurt you. I stood still as I felt something come down over the top of my neck and wrist with a click. I realized she had placed me in the stocks. I felt soft surrounding my wrist.
This is not it but gives you an idea.
https://www.xnxx.com/video-xlk0x48/...d_made_to_squirt_in_bucket_by_master_the_pope

Oh, sh&t... I said. Ann did you just put me in the stocks?

She is in the hi ’40s now.

What the hell was she counting?

I hear her heels as she walks back to the bench. It got to quit. Ann are you in here. I don't have any idea if she is just staring at me. This darkness is screwing with me.

I try to push up! Pushing harder and even harder... FUCK! I try pulling my hands back, pulling back against the padded leather but it's way too tight to pull my hands out... Oh Sh&t keeps running through my head...

I push forward with my shoulders and wrist it doesn’t even budge. I try pushing and pulling trying to rock it but it is solid. I try to move my legs pulling up but they are stuck. My ass sticking up in the air I feel this sense of humiliation for a moment...

Ann comes on are you in here? What are you doing I say as I adjust my wrist and head trying to get comfortable now?

She counts up a couple more... Enjoying watching you struggle darling. It turns me on, shame on you, I am all wet now.

What do you say in this situation? I am speechless.

Let me out of this and I will take care of that problem for you.

I bet you would she says. I have to go get my laptop I will be right back. I hear her leaving the room.


Why would she need her laptop?

OMG, I think to myself. What the hell is she counting? I am starting to feel the pressure on the balls of my feet and can really only lift the weight off my foot one at a time. I can pull up about an inch or two off the ground to release the pressure but then all the pressure is on the other foot.

There is an element of truly being in bondage unable to escape that really turns me on. This was doing the trick big time as I testing to see If I could somehow get out of this. I quickly got reminded I was wasting my time trying.

I hear her heels walking back into the room and now coming toward me. How are you doing over here babe you getting comfortable yet?

No I kind of giggle, come on Annlwhat are you doing?

You will see... counting again.

I hear her doing something then she walks in front of me.

Ann comes on let me out of this I light-heartedly laugh.

You are so cute when you beg but I have some work to do. Just then I unexpectedly feel a painful pinch on my nipple as I open my mouth Saying Ouch... she immediately shoves a gag that goes deep into my mouth. Pulling the leather strap tight around my head. I now have 2 small holes to breathe through and have to fight my gag reflexes. I have to concentrate not to gag with this thing in my mouth.

She says, 57 my sweet little stud.

57 I feel both her hands holding my cheeks through the leather. That is how many times you disrespected me since you walked through the door and did not call me ma’am.

Oh, sh&t I thought. I couldn't talk with this damn gag about choking me.

I told you I was going to punish you and now I am going to make your fantasy come true. I heard her heels clicking as she walked behind me.

I needed to concentrate not to gag on this f’ing thing that was trying to go down the back of my throat.

I felt her soft hands circling on my ass. Now as part of your punishment you are going to feel something cold in a second.

here so I don't have to explain it.


I felt something cold as she started pushing what I would discover Is a steel locking butt plug up my ass. I tried to protest moving and pulling but it impossible to stop what she was doing! She slapped my ass really hard and sternly said stop moving. My breathing was very heavy through those two little holes.

She had poured lube on it and was now slowly sliding it in as my ass tightened my butt muscles trying to stop it. To no avail. OMG... I felt it going in. The F word kept repeating in my head. I have never had anything in my ass before. It felt huge.

There we go... good boy. Now in a moment, you are going to feel this expand.

Expand, I thought? Where the hell is it going to expand it feels too deep already.

3, 2, I take a deep breath cringing my fist waiting for whatever was going to happen. 1.... I felt an expansion in my ass UMMfppp... She giggles. You like that don't you? Oops I almost forgot to push the lock shut to hold it in place. THERE! Very nice. Now you will never get this out of your ass without my key. Sexy isn't it?

LOCK? WTF?

Good boy. You like that don’t you?

Shaking my head NO in protest...

Well, you better learn to like it because it's not coming out most likely until tomorrow morning.

NO... was going through my mind...

Now, Let me remove your cage.

OMG... I HAVE NEVER felt anything like this. The pressure in my ass was intense, my feet were starting to hurt, I was bent over unable to do anything about it, I couldn't see a thing and this gag was starting to really be a challenge. I tried to swallow it was almost impossible and I was drooling.

She removes the cage and he sprang into a throbbing hard-on. ohhhhh.... Look at this he loves what I am doing to you. Look how hard he! How cute she says. I feel her stroke my dick as her nails tease me.

Still focusing to find some way to get this gag to not cause my gag reflexes to work.


Rubbing my penis tickling me with her nails. OMG that feels soo good I think to myself. Don't stop please don't stop.

Maybe I should leave you here all night? Naughty boys should be punished don't you agree? She smacked my ass really hard. Ummpfff... She said naughty boys should be punished don't you agree. I tried to say yes ma'am through the gag without choking.

I hear her heels clicking on the floor as if she is pacing around me. So you disrespected me 57 times tonight. I politely asked you to respond with a simple Yes ma’am and you disrespected me didn't you? Not once, not twice but 57 times. I even counted them for you so you couldn't dispute my number. Now You need to be punished for your disobedience and taught a lesson so you don't do that again. I totally forgot I agreed to let her punish me for not saying yes ma'am. I thought she was going to edge me or something. I never expected a real punishment. What was she going to do?

Let me be clear. From now on when you walk in here you will say YES MAAM when I talk to you. So that you remember to do that... would you like to spend the entire night like this or would you like me to put my lovely spanking machine behind your ass to disrespect you 57 times?

WTF??? Please tell me she is kidding.

I am going to give you some time to think about your punishment. I will be back soon. If you don’t pick one I will pick one for you, my love!

Holy sh8t she is serious about this. My heartbeat changes my breathing is changing.

I am going to get a nice glass of wine so you enjoy yourself ill be back in a little bit Be careful with that gag in your mouth. Let me give you a tip... Sucking it helps you not feel like gagging. Suck hard, my love.

I tried. She was right. When I stopped trying to suck on it I felt like gagging.

Knowing she was out of the room I struggle like hell for a moment trying anything to break out of this damn thing! F...F...F... my ass was full and I could not get out.
I am somehow helplessly turned on like crazy right now.

I don't want my ass spanked that is for sure. That is going to hurt for a few days. Can I make it like this all night? Pushing back and forth on the stocks realizing I am in trouble. I am fucking stuck here. Sucking on this stupid gag is starting to annoy me. Where the hell is she?

My head is spinning. I needed a plan b. In some strange way, in my sightless world, I am visualizing licking her pussy and her squirming in pleasure. I wanted to lick her pussy really bad right now. Ha, maybe I could beg my way out of this. So many things were rushing through my head. I did not want my ass spanked by that damn thing. I kept telling myself she told you she was going t punish you. WTF were you thinking?

Finally in what seemed like forever, I hear her heels as she comes up behind me. She notices I am still hard. Oh my. Marathon hard on? Good boy, you love this don't' you? She starts stroking me. Please don’t stop is all that is running through my head. Once I start thrusting she stops. No No.. Bad boy. You let me control the pace.

Well my love, I know you enjoy sucking on that gag but it's time to remove it. She unbuckles it pulling it out of my mouth.

O M G thank you for taking that out. My jaw hurt. My breathing was heavy through my mouth.

Yes it’s big, isn’t it?

Ann, I am so sorry I forgot. Let me make it up to you. Let me out of this and I will lick your pussy and give you an orgasm better than anything you have ever felt. PLEASE? please I will do anything you want I hate that spanking machine.

Giggling... How cute are you begging? Yes, Maam.. I begged harder than I have ever begged. I felt her hands on my face through the leather as she kissed me. Being in the dark is messing with my head.

You are so adorable when you beg. You know that turns me on. But I am going to keep my promise and punish you first. I expect you to call me Maam in here.

You are going to lick my pussy better than ever have anyway when we are done so that is a given. You are MY pussy slave. I got triggered hard. Calling me pussy slave is really making me want to lick her pussy and make her come. I feel it deep deeper than deep for some reason. I am lusting to make her cum right now.

Please come over here I want to lick you so bad let me taste you please.

73 she says...

FUCK.. Please MAAM.

Good boy.

I know this is turning you on, isn't it? Don't lie.

Great! I have to answer to prevent 74.

YES MAAM. If I say no she will say my dick says otherwise.

You love it when I spank your ass don't you?

Oh no...

ye... a I breath out YES MAAM.

I am screwed.

Good boy. Then that is your punishment.

She already had it set up behind me but needed a few minutes to program what she wanted it to do.

This is not the same but gives you a good idea so I don't have to type it all out. She can program the speed, the time between strokes, random, etc. on a simple computer program.
https://tubesafari.com/video?id=adZv

I am going to do a few test swings... I hear the whisp of the leather string. Perfect.

OMG... I pull on my arms.

She moves it in place.

Tell me you want 73 strokes so you will remember in here you call me maam. Out there you NEVER call me ma'am. It's a game and I want to play it. I think after this you will remember to say YES MAAM what do you think?

YES MAAM I won't forget ma'am.

WHY THE HELL is this turning me on?

You are going to say Thank you ma'am after each stroke. If you forget one I will add 5. Do you understand?

Yes Ma'am I reluctantly said.

I am going to add 2 strokes I want to hear a little more enthusiasm.

YES MA'AM.

Good boy.

I felt her hands and nails softly touching my shoulders down to my waist and upper legs. Her soft touch felt so good.

She must have walked back to the computer to add the 2 strokes returning saying You are all set.

Fuck I am so nervous. This is going to hurt.

I wanted to beg for her not to do it but I was afraid she would add more strokes.

I have set the machine to 75 strokes and on Random. You will never know when or how many were coming at a time. She settled in on her knees underneath me as she started sucking my cock. The first stroke came, I heard the whisp and felt the sting. Oh sh@t! I jerked. Thank you Ma'am.. She giggled.

Good boy.

She slowly continued sucking on my dick. 15 strokes in the stings were starting to get real. She had now poured good head all over my dick and when she took my dick out of her mouth it was ice cold, when she went down on the shaft it was really warm. It felt so good until another strike. Thank you MA'AM!

My breathing increasing.

I felt 3 stokes come quickly. I repeated thank you ma'am three times quickly. Sometimes it waited like over a minute to swing and other times It went right away.

I felt her pulling on my right nipple than a pinch. now the other. She put the nipple clamps on. This was about the last thing I needed right now. OMG, it really made my dick want to be stroked.
What do you say? THANK YOU, MA'AM. Good boy.

At 35 strokes my ass was burning and I was on edge to cum. Talk about pain and pleasure.

She kept me on edge the entire time not letting me come but getting so damn close. Finally, 75 and a bell went off. My ass was in so much pain. She rubbed something on my ass cheeks and that damn butt plus was still causing me problems. She put a freezing cold cloth on my dick as it shrunk putting the cage back on.

She let me up from the stocks and I was stiff as I tried to stand. My feet killing me. She removed the stocks on my feet and I felt something on my ankle She put on the steel cuffs locking them on. There just in case, you try to take this off.

She walked me to her cunnilingus chair where she had me get on my knees. I knelt on a soft pillow. My ass burning but whatever she rubbed on it was nice and cool. The plug in my ass was driving me crazy. I reached under to pull on it. FUCK. It's stuck alright and there was a lock in it she wasn't kidding.

You speak only when I speak to you do you understand.

Yes Ma'am.

Good boy.

She pulled on my hood bringing my neck to be latched to the chair. just before latching it she unlocked the hood and removed it. It was a dark room but still seemed bright after being in pitch black for the past few hours. It felt good to have it off now.

You all know what happened next. I made her squirm in orgasmic pleasure. She was so horny from all this she was coming as I have never seen her do before. Long breathless pauses and moans with her eyes rolling in the back of her head gasping for more.

I know this is long. I will continue on with more later.

 

This chastity device is really getting to me when it is left on for longer periods. I know some of you would laugh at 7 - 10 days being a long time but it's no laughing matter for me. I get freaking horny.

I am so controlled by her with this in ways I never knew was even possible. There is something really cool about her getting all wet and bothered by locking up my dick. This steel device is shameless at keeping me ready to please her. She normally doesn’t keep me locked for longer durations like this but I just realized she was on her period the past several days and it ended a few days ago. Just in time for Valentine's day. It now makes more sense why she locks me up for these longer stints and denies me. I just priced that together. I am going to get out of this damn thing tonight If I have anything to do with it. I need to come.

Her nails are affecting me far more right now because I am so horny and have not been able to release any of my sexual frustration it's all built up inside now.

Someone asked if I think the hypnosis was worth it. Hell yes! I don't mind giving her cunnilingus. It's one of the sexiest things I do to her. Watching her squirm in pleasure is more enjoyable than I could have ever imagined. it's a real turn-on. I crave it. It's almost as good as sex itself right now. Even if this were a result of what the hypnosis did, I don't care. It's a major turn-on for me so what would it matter?

We spent the morning discussing some new ideas for Dom to do with hypnosis. Ann comes up with some wild stuff.

I know I am in for some fun tonight. Can't wait to get out of this thing.

 

https://dark-freya.com/the-taste/

Someone sent me this one thought I would share it for those of you that enjoy this... No, I have not tried it. I don't think it has the same trigger as Nikki's file does but could be fun for the right couple.

 

You got me there. She has totally managed to lull me into a new level of submission and it's been pretty sexy to be honest. I would never have done some of this stuff. I never even knew I liked some of this stuff she does and I do believe Dom's hypnosis is working too or something?

It all started with Nikki's file. Her nails started to trigger me to want to lick her pussy. It worked and I couldn't ignore them so the more it worked the better it worked. Now she can easily trigger me with a couple of trigger words as well and I feel totally submissive when she does. She can put me on my knees to lick her pussy anytime she wants right now. I want her too! That is the crazy part. Her pleasure comes first, second and third and when she is horny I just want to drive her madly wild teasing and pleasing her sexy body.

I am not so sure she wants me feminized? Right now I wouldn't likely do that but then again I don't really understand it if it's more than the obvious of dressing like a female. She has me in a love hate relationship with heels. Sexy but they start to hurt your feet.

 

I am of the belief there are a hell of a lot more cougars out there looking to have fun than people may realize.

https://www.metrotimes.com/detroit/...find-mature-dates-online/Content?oid=26106928

https://www.huffpost.com/entry/coug...kb0GlmsSMobm566j7Vnq7qjEulpUvN_t_ra9uoe6IsMpz

 

Okay, I am having a tough day today. I am trying to deal with the length of time I am being locked up. This chastity is really starting to f'ing mess with my head. It's freaking relentless. It seems like the longer she keeps me locked the more submissive I am feeling, is that normal? I would freaking do anything she asks right now to get out.

I just need a key. It would solve everything. She would never know and I could play along nice and simple with her. I feel like I am on survivor looking for an idol trying to find that damn key in this place. It's impossible to even know where to begin to look.

She seems hell-bent on keeping me locked longer and longer and says I am about to have some new experiences along with it. If the experience is to do anything she ask she is damn right. I have been locked up the longest ever now. I know, I know it's not that long for those of you going months, but I have no idea how you do that!

I just had to rant to feel better for a minute. If the head of my penis didn't feel so good in this tube it would be a lot easier.

 

You guys are incredible. I’m not there yet.

It got real alright a few days ago, no question about that. The emotions ebb and flow. I get so horny at times it’s unreal. I think what you are saying is I will learn to embrace this feeling but I’m not there yet. She keeps telling me the longer I go the better it will get, to trust her. I am not sure how it gets any better I already want to respectfully screw her brains out as they say. I want her so bad. She is over the moon with all the affection and my drooling all over her.

If women only understood how perfect this damn chastity is for them I would bet large many more men would be locked up! this doesn’t get any better for them.

In the mean time I can’t get enough of licking her sweet sexy pussy and when she starts rocking her hips in erotic pleasure... it’s so gratifying. I am enjoy giving it as much as she is getting it. The triggers are as strong as ever. She knows she is capable of using my mouth anytime, anywhere and anyplace she wants and she does. I have no idea how many hours I have spent now perfecting this selfless act.

If you have never tuned into her reactions and focused on making her feel better then she ever has when licking her pussy... you may be missing out on a special connection.

Someone messaged me that they wished they could listen to Nikki’s file but they didn’t think their wife would like it. I am no expert at relationships but maybe Practice on her and once you get her to love how you make her feel introduce the file. What’s the worst that can happen?

In the mean time I am being forced to embrace the denial.

 

She was wearing really sexy skin tight black shinny leggings today (look like leather) with high heel boots and a sweater. I kissed her and put my hand up under the sweater on her warm breast. I can’t stop seeing her perfectly shaped ass and sexy legs in my minds eye. Along with other outfits she teases me with.

It doesnt make being locked in chastity any easier that is for damn sure.

Anyone else agree women have so much power over men with sexy cloths etc. It’s kind of unfair in a way.

Heels, corsets, lingerie, nails, pretty lashes/eyes, makeup, hair, cleavage on and on...???

It seems like about the best a guy can do is work out and eat right so you look tight without a shirt and maintain a 5 o’clock shadow if she likes it???

 

I am getting close to double the longest time I have ever been locked up. The helplessness and struggle is real but I am finding it is starting to get a little easier somehow. I feel incredibly submissive more so than ever. She seems to be able to control my mind and actions more easily in this state.

She found a particular Clitoris Cream that seems to enhance her orgasms with just a couple of drops of this stuff. She carries it in her purse now. Dabs a drop or two down there and 15 minutes or so later she is more sensitive than ever. Good thing because I needed something so I could find a way to spend more time licking her beautiful sexy hot wet pussy. Sheesh... I am down there a couple of times a day but don't get me wrong. I cannot get enough.

As many orgasms as I have now given her, I have a couple the really stand out in my mind. I can so easily tell the good ones now. It's such a turn-on.

I am finding what it's like to serve this beautiful woman more and more her way as I just surrender to her right now. . I cannot get enough. It feels so good She was right that a longer lock-up would change me again and I feel it.

So much to catch up on over the past couple of weeks I don't even know where to start.

more soon.

 

A hypnotic chastity belt...

BELT ON.... BELT OFF! Once keyholder says belt on you cannot touch no matter how hard you try.

Would you give your keyholder this option?

 

In Vegas for a fun weekend getaway. Staying at the Waldorf Astoria beautiful view of the strip. This place is nice, you check in on the 23rd floor which is different. Rooms are very nice.

Meeting up with friends. Going to watch the Vegas Golden Knights tonight and party it up with some gambling at the Cosmo later tonight. I really have fun here.

Pretty sure I will get out of this damn thing tomorrow for some much needed sex.

She is soaking in the tube right now and I’m going to be licking her pussy making her squirm in pleasure before we go out. Her nails have been driving me crazy today, I’m so horny. She’ll be all soft and warm. This woman is so freakin spoiled it’s sick. A womens body is so beautiful. She can put my tongue between her legs at will and leave me wanting to do it again an hour later.

I’m going to see her in thigh high boots and a sexy leather outfit all night. It’s going to be really difficult being in chastity. Touching that leather ass when I kiss her is remarkably sexy. Makes me want her so bad.

Women have so many advantages when they figure this stuff out, is that even fair?