Cougar relationship

Day 3...

It’s impossible to type everything that is happening. After some small talk and my complaining about my blue balls ached yesterday, of which Dom seemed to fully enjoy hearing about, she asked me to explain more about how I feel performing cunnilingus on Ann.

Nikki’s file had a huge impact on me. I tried my best to explain. I can give her an orgasm, see her nails 10 min later and still want to lick her pussy. It’s relentless.

Okay, that’s really adorable by the way. So let’s expand on that.

I have 3 things for today. She read from a list.

1. We are going to strive to Perfect the art, skill, gift ( whatever you wish to call it) of Cunnilingus. There is so much more you can explore with this and It’s going to take practice! Lots of practice for you to find what sends Ann helplessly falling of the edge of her orgasms further and further each time. I know you are not married (yet, you really should get a ring on her finger she is clearly a great catch, as she grinned) but there is a saying, happy wife, happy life. Let’s keep her happy!

2. You being highly suggestible to hypnosis gives us some fun options. You are a very lucky man. We can have a lot of fun with this. I want to test a snap induction. I will explain in a moment. It lets me put you under much faster to give you suggestions.

3. This morning Ann is going to give you 500 strokes. I want to remind you DO NOT COME! Listen to me closely, you will NOT enjoy your punishment so make sure you DO NOT COME!

Ann is very smart, she is a very fast learner. I have instructed her what to watch for and how to use it to edge you. Yesterday was a warm up. She will master her skills in due time just as you will yours.

After a short lesson on the g spot and how different areas cause different sensations she gave me some things to practice.

Next she put me under I can remember everything she said this time. She woke me up. When she snapped her finger and said sleep, I did. My body went limp my muscles relaxed, loose and limp I slouched down. This is weird I thought. I did not want to move. I remember everything. She snapped her finger wide awake. I woke up. She repeated this a few times until she was satisfied. Very good.

Now SNAP sleep. My body went loose and limp slouching down in the chair. SNAP SLEEP she repeated like 4 times each time taking me deeper. Very good.

readers digest version...
Today Ann’s pussy is going taste like a delicious desert. You simply cannot get enough of it. You will savor every lick, every suck. You will slowly, very very slowly bring her to the point that she is begging you to take her over the edge to come using what we discussed today. Messaging her g spot and teasing her clit in different ways. The more she begs the better your dick feels in your cage as it twitches In pure pleasure. The sight, smell and taste of her pussy will be erotically intoxicating. If you understand say yes dom. Yes dom. SNAP wide awake.

She smiled and said you two are going to have fun with that one.

Ann is waiting for you. She is going to do the 500 stroke challenge this morning. That leaves you the rest of the day to torment her with that sexy mouth of yours. Good luck and remember if you fail you start over at 300 so be careful.

 

Thanks for the advice. I am young dealing with someone far more experienced then I. But so far she has made it better then I could ever have even imagined.

 

Sure enough she was waiting for me.

I don’t need to give you the details of this experience, you already know the process. The extra 200 Strokes seemed like way more when It is taking fewer strokes to get me to the edge the longer this goes. Some how she knows to pull off just in time.

We finished and sure as hell she locked me back up. It’s nothing new that her damn nails were doing their thing. I swear the longer this goes the better they work. This time she let me out of the restraints when we were finished. Kissing and fondling her I picked her up and sat her in another chair with a base shaped like a V. It has QUEEN in the leather padding above her head. She calls it a queening chair whatever that means.

I couldn’t wait to tease her. I spent a lot of time just caressing her kissing all around her pussy without touching it. The teasing was working. I finally gave her a wide slow wet lick with my tongue and she was soaking wet. OMG That tasted so good. WTF? I licked her again and again. She taste good anyway but this was unreal. I had to force myself to slow down as It dawned on me how much she loves this. Is Dom right? Maybe I actually could learn to control her with my tongue in ways. I was starting to see what that might mean.

I completely lost track of time. Messaging her g-spot while teasing her clit took more focus. All I know is her hips were starting to shake and just kept shaking and shaking. I watched as her eyes rolled deep in back of her head. She was clearly enjoying one hell of an orgasm.

She finally pushed my head back. She started slowly laughing... whatever you are doing was amazing. She was still gaining her composure pulling me up to kiss me.

You brat! You are really getting good at this.

Brat? She called me a brat? Why am I a brat?

She was joking.

Well I am coming for you again after lunch so you better recoup quickly I told her trying to tease her. I can play her games too.

I guess I better where a short mini skirt with those heels you like? If you beg I might let you enjoy yourself again? She always has to get in the last tease.

 

Day 4/5

Catching up from yesterday... I do enjoy these talks with dom. I never know what’s in store. I explained to her what she taught me yesterday worked. Ann had a crazy crazy crazy wild orgasm. I don’t think I could ever top this one.

You are thinking like a boy she explained. One orgasm and it’s over. When done properly, she is capable of having multiple orgasms. Women, unlike men, don’t need to experience a ‘reloading phase’ when they come the first time. I sent you a book that will arrive today. She Comes First: the thinking man’s guide to pleasure a women.

Much of it is a mental game that you use to set the stage.

Little things like After her first orgasm give her a moment to rest, her clitoris will become a very sensitive spot and a short break is necessary. That’s your cue for paying attention to the other areas of her body – like her breasts, her neck, her ass, feet and other non-genital pleasure areas. Whisper sweet nothings into her ear before you make your next big move. Keep the heat turned up.

After you finish the book, we will talk again.

Hmmm? I am learning so much. It’s like the ultimate sex education class. Women are so much more complicated and complex then men.

Moving on...

Today, I was going to get 750 strokes. I am so horny, it feels like I could come so easily right now. She explained this time the strokes would be less predictable. For example 3 fast, three slow. 2 slow 10 fast. The fast ones are where the hidden danger lies. The orgasm can sneak up on you. You are going to have to be really careful and focus much harder not to come. You know you can always come if you like. You are just going to put on high heels and get you as spanked if you do.

I sort of missed the next things she said, I was trying to figure all this out. I was thinking the offer didn’t sound so bad after all.

Dom continued, Ann has an appetite for cunnilingus unlike anyone I have ever known. You would think she has a penis not a vagina as much as she wants played with.

She is learning how to know she got you as close to orgasm as she can without you going over the edge. When your penis jerks once or twice but nothing comes out that is the closest she can get you and she was successful a couple times. She is getting the hang of it.

She has been bringing you close to the edge of coming and letting you fall back. Today she will practice getting you to the edge and along with her hands she will use her warm wet soft sexy mouth to keep you there. I have explained to her an example using a thermostat. If at ip degrees you are just normal, 90 you feel aroused and 100 you shot your load, she is going to attempt to keep you at 96 to 99. Back and forth teasing you with just another lick from her tongue.

WTF?

Tomorrow she is going to suck every single last ounce of come she can get out of that penis. But you have to get through all 1000 strokes first.

Now I would like to give you something. Hypnosis can do some crazy things. Would you trust me to do something I know you will enjoy?

Like what?

You have to just trust me. I promise you will like it. You have to get through all 750 strokes for the reward.

Okay fine. Show me what you have.

SNAP
SLEEP
SNAP
SLEEP
SNAP
SLEEP
I was out. She kept taking me deeper. Last I remember was her saying something about remember to forget and forget to remember.

3 coming back, 2 feeling good, 1 deep breath stretching wide awake feel piling great.

Okay, you did great. I have to run good luck today and I will see you tomorrow.

Looking at the clock some 20 minutes passed. I didn’t feel anything. My mind was blank. The more I tried to recall what happened the more empty or blank it was.

I have no idea how I made it through this but I did. One more day.

this time she put me in the chair locking my hands to the side and my neck in place. 2nd time now I have been in this. She crawled up. Her thigh high boots rubbing against my arms. All she had to do was slide herself forward and my mouth as in perfect position. My nose could tease her clit. Her sexy hands were warming her up. Circling her clit. She slide forward as I slowly started teasing her.

She moaned and my eyes shut as my groin tightened and it felt like I just had a single ejaculation that lasted for like 5 seconds. WTF was that. She put her head back in pleasure. OMG that feels good. Ooohhhh... she moaned again and my eyes closed and felt a long powerful ejaculation followed bu 2 more.

I cannot pull my head back to get my mouth out of her pussy. Her nails are messaging my head. That’s it, she says, a little faster oohhhhh my God she moans.

I feel it again even stronger. This time I am pulling against the restraints in pleasure. I now realize this has to be what dom did. No orgasm feels like THIS! I know it’s not real but damn it feels good. The more I get her to moan the more I feel this.

I am closing my eyes, visualizing this long stream of come shooting out of my penis as my abs and groin tighten and feel incredible.

She is pulling on my head as she pulls herself closer into my face. I suck on her clit as she moans again. I stop in pleasure, She keeps saying don’t stop, don’t stop but I can’t help it. My pausing is prolonging her orgasm and giving me more.

who thinks of this shyt?

finally she came.

Day 5

And it’s Saturday. Let’s see how it goes.

 

Day 5/6

People are asking me to show photos of the things she is using. So I will try to do my best.

Big plans tonight (Saturday). We are watching the UFC fight tonight with our friends. McGregor is on the ticket so I am thinking it could be an interesting fight. Hasn't fought in a year.

Changing topics. She called me to the "playroom".

Entering she met me with a long sexy kiss. It certainly set the mood.

She had stuff set out on the bench. She asked me to get naked then handed me a pair of thigh-high boots. I know you have been waiting to wear these again. It was kind of humiliating, to be honest, but it was true. These things are so damn sexy. I couldn't even resist. My throat got dry and I was feeling the excitement in my penis as I slipped them on. They looked and felt sexy.
Very similar to these:
https://www.wish.com/product/5e3538...begoJW56EStt1J3MNUsoyAaAli9EALw_wcB&share=web


She proceeded to put steel cuffs around my ankles locking them shut. Very close to these.
https://www.etsy.com/listing/738500...y=metal+bondage+cuff&ref=sr_gallery-1-7&frs=1

It was normal that she would put cuffs on me but these were much different.

She asked me to try to take a boot off. I unzipped the boot but obviously not far enough to be able to take them off. I could not get the zipper under the cuff. She smiled. Very Good. Now Stand up.

OMG, these are so sexy I thought to myself. I am standing on the balls of my feet and it feels good right now. I see how heels would make women feel more powerful and confident but it's rather humiliating in front of such a beautiful woman.

She walked me over to the bench where the stuff was and pulled this out. See here.
https://www.boyzshop.com/collections/handcuffs-irons/products/metal-bondage-fiddle

She proceeded to fasten it to a chain hanging from the ceiling and pushed the lock shut. There she said. Let me look at you. She backed up looking at me. OMG how cute, she said. You look sexy in heels. That l little ass of yours. Okay so now I can remove the cage. My dick sprung into action with a full-on hard-on.

She pulled out this little remote button and tapped it to my hand so It would not fall off. What is this I asked? She said if you need me you can press this button. But I only want you to use it for an emergency. I am going to let you enjoy this for a little while. She went behind me and slapped my ass like 20 times. I started to hurt. I have the whole day to play with you, I'll be back in a little bit to check on you.

I had no idea how long a little bit was. Okay, what the hell did she just do to me? There was NO WAY out of this thing that was for damn sure. I am guessing 20 or 30 minutes passed and the balls of my feet were starting to hurt. I pushed the button. I heard her heels clicking as she approached. Peeking her head in she asked are you okay?

Yes, I just wondered where you were? She said I told you not to use this unless it was an emergency. I know but my feet are starting to hurt. She shook her head.

She went to the table and grabbed a gag. like this.

https://www.etsy.com/listing/890059...&ga_search_query=panel+gag&ref=sr_gallery-1-4

She grabbed my nipple and twisted hard it hurt. OPEN UP! She shoved this huge ball in my mouth and strapped this thing around my head. She would adjust one set of straps then another then tighten the first etc. It hands a strap that wrapped under my neck pulling it tight against my skin. I was unable to utter a word. MMMPPFFFHFF. That was all I could say. She pulled out some nipple clamps. This pair was different. She pulled on my nipple and began to squeeze this clamp on me. I started to struggle. She grabbed the other one and did the same thing. Then she went back to the first one and pushed a little further. She teetered tottered back and forth until they were fully shut.

There now Maybe you will think twice about pushing that button for anything but an emergency.

I was so turned on I couldn't take it. She spanked my ass again and said I have more so I suggest you only push that button if you REALLY need me. She smiled and walk off. She was almost out the door when she turned around and came back. She said oh I almost forgot. She took a padlock and put it on the nipple clamp chain and shut it lowering it. I felt the tug on my nipples. MMMMFFFFPPHH.....

She walked out. WFT...? I struggled but doing so moved that damn lock around causing my penis to want to be stroked from those damn clamps. I am freaking helpless right now. What the hell will she accept as an emergency? I was afraid to push the button, who knew what else she would do?

I have no idea how much more time passed when I finally heard her coming into the room. Hello babe. Oh my God, you look so cute.

It's time to start your 1000 strokes. I shook my head back and forth no, no, no! She smiled and said stop, I am confident I can keep you on the edge without your help.

She pulled out the PJUR and poured it all over my dick. She said i think you are warmed up now. She started rubbing, I will spare you the play by play action but she finally reached 1000 strokes. OMG you did it. She said now you get your reward...

She took a warm wet cloth and cleaned me off. She poured good head all over my dick and started sucking it. She would stop and look up at me saying I am going to suck every last drop of come out of you. My nipples and feet were numb. I was so turned on. My dick felt hot then cold then hot then cold. I tied thrusting it further in her mouth as she uncovered it.

It didn't take long and I lost it with the hardest longest most amazing orgasm I have ever had. It was unreal. She literally drank every drop licking me off. She smiled, did you like that my love as she stroked my cheeks with her nails? I shock my had up and down. You do realize everything I am doing is to give YOU a better orgasm than the last one. Quality over quantity.

All of the sudden the adrenaline or something left my body and my feet were killing me, my nipples hurt. Ann said it's time to remove these. She unlatched the left one and I let out a scream in my gag but you couldn't hear anything. DAMN, that hurts. Then the second on as I cringed down on the gag trying to take the pain like a man. UMMMPPPFFfffffff... She smiled. I know it hurts babe. She locked me back into chastity.

She unlocked the thing around my neck. OMG, it felt so good to be out of that. My arms had been in the same position for a long time now. I stretched them. I sat down on the bench taking the pressure off my feet they hurt so bad.

What time is it I asked? around 1. I have been here for over 2 hours?
Yes, good boy, she smiled. I am impressed. I was waiting for her to give me the keys to the ankle cuffs. Lay down. rollover. She gave me a back rub for like 20 minutes and it felt so good. She even rubbed my feet through the heels. Now maybe you will be more compassionate when I ask you for a foot rub. Oh man, I get it I said.

She stopped and said, ok you can get dressed. She changed into some sweats and said I have to run some errand before tonight. I will be back soon.
Great where are the keys to these cuffs. She kissed me and said be good while I am gone.
I will, Ann where are the keys to these cuffs? You don't need those. I am not getting dressed wearing these boots Ann!!!!!! Suit yourself she shrugged her shoulders. She kissed me and started walking out. Ann.... ANN... Hey.... wait what are you doing. FU&K! Thinking she was joking I waited a few minutes to see if she was coming back. She didn't.

I sat there trying to figure out what to do. I finally stood up and the severe pain was gone. I pulled my jeans up over the boots. They looked really sexy. I put my shirt on and as I walked out in the hallway I was like paranoid someone was going to see me. No one was there but I still felt like I had to watch for someone. I went up the steps not putting the heel on the step. It sort of stretched my foot out and felt good. I got to the top and once again had to walk on these damn heels.

I went to my computer sat down and just relaxed for a minute reflecting on everything. The cage already felt good again. I would see these heels on my feet and my dick would get aroused again. My calves were constantly feeling tight from having to keep my heel 5 inches off the ground. I would turn my ankle at a 45-degree angle to release the pressure but eventually, you put your foot back and feel that tight calf again. I had not eaten. I walked down the kitchen and made a sandwich. These heels were turning me on like crazy again.

I thought maybe I could find the keys. I walked to the playroom and looked everywhere. No keys. WTF???? I walked back to the computer my feet starting to hurt again.

I text her ANN where are the keys to these cuffs?

In my purse. Is there a problem?

No.

Tell me you love them.

Ann ???

Tell me.

Fine, I love them.

Good, I bet you look so cute walking around in them. Maybe I should leave you in them for the party tonight.

ANN... you are out of your mind if you think I am wearing these damn things tonight.

I am just teasing you. You know this control thing turns me on? I am going to be so ready to use that soft sexy tongue of yours tonight after the fight my little pussy slave. I might even suck every drop of come out of you again tonight if you are a good boy.

She scared the hell out of me. She did let me out and It felt so good to put my feet flat.

After the game we were in bed she whispered the triggers in my ears but her nails were already driving me crazy. I spent the last part of the night licking her to an orgasm. I remembered what Dom said and I focused on other parts of her body for a few minutes after she came. Then I started slowly again on her pussy. She came again. This time he clit was so sensitive I had to stop.

Day 7... Now what?

 

intentionally blank.

 

Day 7

First, let me say I am totally blown away at how fast she is getting at putting this cage back on. It is not a simple task. You have to put the ring around the head of the penis lube it up. Get the anti-pull out to align up with putting the screw through it. Attach the cage lock it on. She has had practice but man she does it faster and more smoothly than I can. It's impressive.

Dom couldn't believe I had made it through all 1000 strokes. She was excited because this would let us move on to the next level as she called it. Anns orgasms.
The next few weeks you are going to be laser-focused on her visual queues far far far more than you ever have.

She sent me a few videos to reference of women getting totally lost in their orgasm.

She wanted permission to utilize her hypnosis to help me with this. The goal is to bring her to a level of orgasm that would leave her speechless, breathless, and momentarily submitting fully to the pleasure.

How could I say no to that?

After our session, I finished reading the book she sent. I went to my computer and studied the videos she shared a few times.

The clit has thousands of nerves. Women reach orgasm differently and mood can be important to reaching a good orgasm. Experimenting with different methods of teasing, pressure, speed, external stimulation and having lots of patience—can help figure out what works best for her. Women have it easy, stroke our dicks and we come.

Although, I will admit, she just gave me the best orgasm I have ever had yesterday. She had me so wound up that when I finally got to cum it was explosive. So maybe there is something to all this?

Dom asked to send me a text. She said she wants to center her hypnosis around this outcome. Sure I said. Send it.

Dom's TEXT MESSAGE:

ADDICTION TO THE TASTE OF… HER PUSSY!
Try to imagine the sweetest taste you can – now imagine it getting 10x sweeter, 100x sweeter, 1000 times sweeter... Wouldn't it be amazing?

The suggestions I give you are going to leave you with a deep and lasting effect on your mind, creating an addiction to the scent and the taste of Ann's pussy. Causing you to lose yourself completely in giving her oral pleasure. Imagine the pride you will feel knowing she cannot stop thinking about what you do to her with that sexy mouth of yours. I will help teach you to please her to her "complete" satisfaction. Beyond what you even realized was possible.

These suggestions will create powerful new neural connections in your brain. The scent of her pussy will become your favorite scent, the taste of her pussy is going to become your favorite taste. You are going to completely lose yourself in the act of going down on Ann. You will lose all sense of time because all that matters will be giving her this selfless act of pleasure. You will be unable to stop until she is completely satisfied.

Think it over and as you do imagine intensifying your pleasure as well. The more you please her the better your dick feels. The more you take her breath away the more she takes yours away when she decides to take you in her mouth and give you pleasure.

Just type YES PLEASE.



I read the text and my dick was pushing against the end of the tube. That last part sounded pretty good.

Screw it. this has all been fun so far.

YES PLEASE...

I typed back!

She smiled at me and snapped her fingers. SLEEP!

I woke not feeling any different. Wondering what this was going to feel like. I won't see Ann until later this afternoon.

 

——————————-

I wondered if this starts to wear off over time but you are saying it does not. I have had a few people tell me Nikki’s file worked well on them too. It’s such a crazy experience that cannot really be explained, it has to be felt.

I’ll send you a video dom shared with me If you like? When you see how intense these girls orgasms are, you are going to be like, I need to learn to do that! It’s fire.

Some people warn me to stop others say they wish they were me. I obviously can’t type every conversation she and I have etc. This may sound strange but If anything she is earning more of my trust. I am discovering things I like I didn’t even know existed. I have also had her do a few things I don’t like.

I am just curious, when was the last time you listened to Nikki’s file? How often do you listen? She is very pleasant to listen too. I notice the more I listened the less I can recall. Especially the second file. The triggers work but I go blank trying to remember any specifics.

 

++++++++++++++++++++++++++++++++++++++
Thank you... All advice is greatly appreciated and taken into consideration and no apology needed. That is in part why I am here. This journal is therapeutic in a way for me. I have gotten a lot of feedback from you folks that have been helpful. Even from others who have experienced Nikki's hypnosis file. I couldn't' agree more this is so far out there but in some regards, I am not alone that is for sure.

I am typing stuff out in this journal for future reference. She has actually gotten me to realize I have fantasies I didn't even know I had until recently. I am 100% on board with keeping one eye open, being smart and prudent. We mesh well together. We like the same things, we get along really well, we laugh a lot, were best friends and we have fallen in love.

She has a chastity control fantasy. She wants a vanilla relationship on the outside. Me being this alpha male with her hidden secret that she controls my orgasms. She has this control thing with Male Chastity. It really turns her on. She loves her pussy being teased. I have never seen anything like it. She is like a guy with getting head. She would take it all day long. We simply agreed to explore each other's fantasies together to see what transpires. So far it has been mind-blowing. She is showing me things I had no idea I would like.

I have had long talks with dom and Ann about hypnosis. We have a clear understanding of what is acceptable and what is not. It's simply being used to enhance both our experiences. There is an element of control that is working for her and we wanted that. I will fully admit the triggers work. Her nails make me want to suck and lick on her pussy. When I do, it tastes and smells so good it's addictive. When she says a couple of triggers I feel submissive and weak and I want to please her.. She really gets off on this control.

If we were to say break up, these triggers would no longer be of use to her. I may want another woman to play with but I am going to want that now anyway if God forbid something happened. The great news is I am perfectly happy with her and she with me so there is no need to look for greener pastures as they say. We are both learning to fulfill each other's fantasies so we don't have to look elsewhere if that makes sense?

Chastity is getting easier. Everyone said it would. It's not EASY. But it is getting easier. At times it really gets to me and I want to jerk off but at other times It feels really good and I like it on. We have a lot of fun together. Her friends tell me she is very loyal as am I. We both like that in each other. We have become best friends. I just moved into her place in Jan and that is when all this crazy stuff started happening. She wanted to further explore my fantasies and hers. She just doesn't hold back as much as I do so she has to pull it out of me.

Again thank you for the message. Wishing you all the best.

 

I don’t know what I was thinking this morning. I woke up early as usual thanks to my cage. I had to get up to pee and walk around to calm him down. I went down and made some coffee.

Curiosity was pulling me to the playroom. New items arrived that I have not checked out. I opened the box and I have no idea what it is. It Has 2 steel rings attached to a couple of steel posts too small for the wrist? No clue what this is. Another has a piece of leather that buttons together with 3 chains hanging from it? There were 4 shoeboxes of high heels. I looked like they were my size. For some reason, heels are turning me on and she has figured it out. I opened a box Whoa...Crazy. What the?
https://www.ebay.com/itm/Wonder-Sty...emsV2WithMLRv3&_trksid=p2047675.c100008.m2219

I opened another box. Geeesh..
https://www.refusetobeusual.com/pro...ain-knee-boots-ykk-lockable-zip-padlock-strap

These were crazy and totally caught my attention for some stupid reason. Of course, I am like a cat full of curiosity I decided to try them on. I took them out of the box examining them. These are very nicely made. I removed the chain holding the key to the zipper. Unlocking the zipper and pulling it down to expose the laces. These did not zip up. I unlaced the boot and pulled my foot inside lacing it back up. Pulling the lacing tight making the boots very snug around my legs I zipped them back up covering the lacing and used the key to lock the zipper. finally, I wrapped the upper strap around my calf locking it in place with the padlock. I repeated the process. I felt excited and my mouth was dry. My dick was pushing against the cage - hard. I examined the boots, rubbing my hands up the leather realizing these were actually now locked on. I set the keys on the bench and stood up and had to balance myself holding onto the bench. Whoa... my calves and tips if my toes felt all the pressure. It was a crazy sensation. Concentrating I took a few clumsy steps. These were not made to walk in I thought to myself. I was so turned on.

I was about 6 feet from the bench when I heard the door open and my heart literally sank as time stood still for a moment. I wanted to hide but that was not going to happen. I heard Ann say ohhh... there you are. She paused... Oh my, my, my my, my... wasn't expecting this pleasant surprise, don’t you look cute she smiled? I turned beet freaking red. My heartbeat changed my breathing stopped for a few moments... Fu@k repeated in my mind like a dozen times. I probably looked like I just saw a ghost. How do I explain this was rushing through my head.

I was so into this I didn’t even hear her coming.

Will, you look at you?

I took a couple of clumsy steps back jumping up on the bench to get off the heels. I tried to make something up to justify this embarrassing moment. I saw you bought some new stuff and thought I would see... by now she was moving in between my legs with her hips pushing them apart... if they fit I finished saying. Looks like they fit just fine to me she grinned. You are so adorable. starting kissing me. Her hands went from around my shoulders to moving down my neck and arms to where my cage was then down to my thigh. I was getting into the kiss eyes closed and all. I felt her right-hand move off my leg then back on.

Mmmmm... More of that later she said.

I think you look really sexy in these boots babe,

Yes about that... these heels are definitely way way way too tall.

Well, maybe you just need some practice time in them. I don’t think so I am still getting used to... she interrupted me put her index finger over my mouth to shush me... ssshhhhhh. She stepped back out of reach and showed me all the keys in her right hand as she giggles saying look what I found? She snuck them off the bench while kissing me???

Funny ANN come on, give me those keys... NOPE! She started to walk out. Wait Ann. I jumped down immediately realizing my predicament. Oh sh#t. I could hardly balance in these damn things let alone run after her. ANN wait.

She stopped at the door looking back at me. She looked so hot. With a little practice, you will be walking like a pro. Just as a reminder, I put those things on your desk you were going to finish for me today by the computer. You really should hurry, you only have 10 minutes and you are on with dom you need to go get ready. I will bring you lunch. I stood there in disbelief as she actually walked out. She will come back, right? Jumping back up on the bench, I waited every second felt like an eternity. Damn. Now what? Sitting on the bench I lifted a leg to cross my foot over my other leg. OMG, these heels are so freaking LONG! Pulling on one I realized these were not cheaply made. I shook my chastity cage trying to get some relief but it was not helping.

I realized I had been in here almost an hour. Where did that time go. My dick was leaking like crazy.

I can't be late for DOM. I jumped back down. My stride length was like 1/4 of normal my arms flopping around at first trying to balance using all my concentration not to fall. I got to the doorway and grabbed on then leaned against it taking pressure off one foot then the other. Leaning helped but it was temporary.

Looking down the open long hall was daunting. I made it to the steps and using that accomplishment to sit down on the third step. I pulled on the lock thinking maybe I can pull it apart. Harder... Harder... SH&T... Nope. Of course not! Climbing the steps was a real challenge. I used the rail the entire way to balance. Finally getting to my desk.

Oh crap, I need a shirt. Screw it. I am not walking into the bedroom to get it. I logged on ( just in time by the way) and dom was there. Oh my, she said. Look at you. I was shirtless, frazzled and my head was spinning. After a few minutes she said, are you okay,? Yes, I just lost track of time this morning sorry about that as I tried to find a comfortable position to put my feet in.

As we talked Dom got me focused on the conversation. After this morning, I wanted that calm, relaxed, great feeling I get when she puts me under and wakes me from hypnosis.

I woke up taking a deep breath, stretching, and feeling great.

We signed off. even though I had tried this a number of times now I found myself again pulling on the locks . F@ck! My text went off. Ann: I am so turned on thinking about you right now.

Me: Speechless waiting to see what comes next. I could see she was typing again.

Ann: I expect you to be this good by th time I get home!


You will be modeling them for me like this.


I got pretty turned on watching these.

Ann got home around 12:30.

She came up to the office. I am angry at you she said. WHY? I laughingly said. She gave me a sexy kiss. Because you have had me all hot and bothered thinking about this moment all morning. Oh how to cut you still have them on, she said.

Yes, I left them on just for you I sarcastically said.

Good boy. the locks are there just in case you get the silly idea to try to take them off. I know you would never do that but, Ya know just in case?

She loves control...

She kissed me... You have turned me into a hot wet mess all morning thinking about you. She sat down in a cushioned chair in my office, I was so turned on.

She used 2 triggers. I felt them right away. The more I tried to resist the more submissive and obedient I felt. I got on my hands and knees and crawled to the chair. She used the triggers again. Obediently I started teasing her licking her upper legs and around her pussy. I teased and teased her before finally licking her wet pussy. It tasted so good. I wanted more. I was touching her body as I slowly teased her with my tongue. When she starts moving her hips is when I know I am getting to her. I started messaging her g spot. She was now rocking her hips. Faster she said. I applied different levels of pressure and speed adjusting for her. As time went on she grabbed my head as her breathing stopped and her eyes rolled to the back of her head perching her head back as her body shook. About 5 seconds later letting out a loud moan of pleasure OMG... curse words flying out of her mouth, Don’t stop dont f’ing Stop she begged,

Again another breathless moment as I increased the pressure and speed on her g spot while sucking on her clit. Her body shaking. Oh f.. she let out like 5 curse words again as her body tensed shaking. She was laughing as she was lost in the pleasure like a little girl. She pushed my head away okay... okay you got me. That's good.

Pushing me away she pulls me up to kiss me. My dick was killing me.

OMG I needed that so bad. She hugged and kissed me for a while. Getting up she adjusted herself. You still are not dressed she said. Leaving the room she came back with some jeans and a shirt.

Here darling she handed me the cloths. Have I told you how sexy you look in those boots? Kissing me. You are such a bad boy... Do you have any idea what you just did to my body and mind? She kissed me again. OMG... Get dressed.

Ann are you going to take these off.

Ahh... cringing she said... I totally left those keys at the office on accident. I will bring them tonight.

You have to be freaking kidding me I thought to my self. FUCK.

For real? Yes... so sorry but it looks like you need more practice anyway. now get dressed let’s go eat.

Does she have any idea what it’s like to try to walk in these?

I wobbled into the kitchen. After we ate I asked her...

I have some questions about some stuff you bought in the playroom. Good I will be home tonight to demonstrate anything you like. What is that metal thing with rings? Oh you are going to love that. It’s a ball stretcher? WTH is that I asked with concern? I will show you tonight if you like. I gotta go.

This f’ing chastity device started really getting to me this afternoon because of these boots that were locked on.

I googled ball stretcher and sure enough https://www.extremerestraints.com/extreme-double-ring-cbt-ball-stretcher.html. Here it is.

She is out of her mind if she thinks i will like that damn thing!!!

 

Thursday morning.

My ankles and calves are sore today. I used muscles I don’t use trying to balance.

My meeting with Dom today went very well as usual. When we started she explained her MO. She likes to find an idea that the subject is hiding or wants to expand on and allow them to feel comfortable about it. She then in a future session increase their curiosity about that idea. And then she increases their arousal about it. Eventually becoming an obsession they are totally comfortable with. And then she focuses that obsession on her and in my case Ann. Each time she makes it more pleasurable for the subject in their response. Erotic hypnosis at its best.

Dom has taken what Nikki started and put it on steroids. In about a week's time working with her, the difference is night and day.

I will digress for a second.
I woke up this morning and she was sound asleep. I saw her nails. This trigger is strong as ever. Trying to ignore it becomes impossible at times.

Screw it, I put my hand softly on her breast under the warm covers. She slowly moved smiling asking me playfully, what do you think you are doing?

Mmmm, I am going to make you feel really good this morning. One of her eyes opens looking at me with a smile, oh really. All I could think about was licking her pussy and making her squirm in pleasure.

I moved the covers and got between her warm legs.

Slowly teasing her eventually licking her wet pussy.

Okay... you can wake me up like this every morning she says smiling. Putting one leg on my back and moving the other to the side as she enjoys the sensation.

I could do this all morning as I lose myself in making her come. Trying to squeeze every last drop of pleasure into her experience.

 

Or not!

 

There are lots of beautiful older women looking for a toyboy/younger man. You can share this for example
https://milffinder.com/landing/mf2000?isRedirectedToDefault=true

A simple search brings up several others.

Ann made the decision to go for a younger man a couple years ago but says she scared a couple of them off before we met. She initially became intrigued with the idea from a series called Cougars Club LA. She just had a different outcome in mind and knew exactly what she wanted.

My experience with Ann is totally different than someone my age. It’s an entirely different thing.

 

https://www.chastitymansion.com/forums/index.php?forums/small-penis-humiliation.118/

 

So for some reason NsToy has started trolling my journal page, apparently incapable of understanding any action contrary to his capacity of understanding one should take? My sincere apologies to you all for not getting this dolts approval before posting.

I have never had any grief from anyone in CM. You all have been great support and I have many dm’s from members here with great advice. Until this myopic clown comes along.

NsToy, I could frankly care less what you insinuate. I could care less what you think. I could care even less what you believe to be true or not true. I just don’t care! I have nothing to prove to you and I will continue to enjoy this journey regardless of whatever vacuous response you feel compelled to spew hiding behind your faceless keyboard.

I could however return in kind the favor of Trolling some of your posts if that’s were you want to take this?

I’d really rather not, the ball is in your court???