Cougar relationship

Discussion in 'Journals and blogs' started by Cougars Plaything, Nov 21, 2020.

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  1. Headtrip
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  2. Cougars Plaything
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    Moved accidentally posted this in the wrong thread.

    So I have a lot of people asking for an update. Well I am settling into my new experience I moved in and she is really turning things up on me quickly. I have had a lot to process but I am finding I feel about this bondage stuff like I do chastity. It's a love hate sort of relationship. She is so experienced in this it's becoming clear that it's not fair and her fetishes are something else. I would never believe what I am about to type if someone else wrote this but you just can't make this stuff up. So here we go.

    For starters she had me established a "safe word" and made me PROMISE that I would never use the safe word unless I was truly at my limit with something. We also made a Safe Gesture. Four taps incase I couldn't say the word. She put tremendous emphasis on what she calls safe play since we are moving into the bondage stuff more now that I live here.. She wants all our decision on this to be mutual and we decided before I knew what the hell I was doing that I would get one freebee with the safe word and after that their will be consequences to using it. Okay I can see why she would want to know I need to, if I use it.

    I can wrap my head around that. But what is she planning on doing that I need it? She said it's only a precaution and it's going to be or she won't move forward. It needed to be something I don't like, and is severe enough that I won't want the punishment. So she brought her devious mind into this little game with some ideas. I will share below.

    First, I had to get to the bottom of this and find out how she knows to do all this chastity and bondage stuff. All I will share is she was married to a very wealthy/powerful man who wanted her to dominate him and did her wrong. She got very large settlement from the divorce including a mansion and more money then she will ever spend. I won't go any further into it then that here but I can share she fully enjoyed her control with male chastity and bondage. She cannot believe I have been so open minded to all this for her and it's really making her feel loved. She is a remarkable women and knows exactly what she wants.

    I will however share that there is a room in this massive house that has some really crazy bondage stuff in it. I had no idea stuff like this existed. She has ordered many new things for this playroom over the past couple weeks that she wants to try. One of the items in a box that made no sense when I was first unpacking it was a chair? But when I took it out I understood this was not your ordinary chair. WTF???
    [​IMG] [​IMG]

    I will tell you about some of that later.

    So what did we come up with as my punishment if I abuse the safe word? Well with her probing me in this direction I somehow agreed that the punishment must be severe but certainly not lasting to detour my use of it. So she suggested something like this. Best way to show you is this video. Although this is NOT our room, this is a video from the company that makes a machine like she has set up in her 'playroom'.




    She decided that if I use the safe word, I would agree to take 50 strokes from this machine but I would need to put on high heels for her before hand. . First of all I am NOT wearing high heels and secondly I am NOT getting spanked by some damn machine!

    Well, if that is the case I can just leave you in your device on until you acquiesce to my wishes? Or you could put them on right now and do as I say and I just might let you out for a really good orgasm afterwords.

    I really wanted to cum. Promise me you will let me out and you got a deal. FINE! What do you want me to do. She said then you must experience what will happen to you once so that you have a reference WHY you don't want to abuse your safe word. But let's only do 25 strokes for this shall we? Keep in mind I had not seen this video and had no idea if this would hurt? I was however getting turned on by all this for some crazy reason....?

    She had ordered these high heel boots I thought they were for her but turns out they are my size. She pulled them out of the box and asked me get naked except for these ash she handed them too me. I have never worn high heels before. It was sort of humiliating in a way, I was like are you serious? YES I am now do it or we will do all 50 strokes. As I was putting them on I was thinking damn these things are pretty sexy to be honest. I zipped up the last one tightly around my calf. Then she had me stand in them and WOW. This was harder then she ever made it look. She looks and moves in them much more gracefully then I ever will. I tried to walk in them and it was an experience to say the least but I started to get the hang of it. I can see why they might like this so far. These definitely make you feel different.

    She took my chastity device off and it felt so good to get a full hard on. In the middle of the floor I was about to discover what this metal thing was used for. I can now best describe it as a stocks to your balls and cock. she pulled a pin out and it was adjustable. We moved it a couple times and finally got the right height. She grabbed my throbbing cock and pulled my balls into the half circle as she lowered the top down and something clicked. I was now stuck standing unable to move from this contraption without pulling my balls off. It was super tight fitting, there was no way to pull out of it just like the chastity ring is. She fastened some padded leather cuffs around my wrist. They were really soft and comfortable pulling them tight. She locked them to some loops on the side of this thing. She now had an erect penis she could do anything she wanted to. She slowly stroked and played with me giving me some really good kisses for a few moments and It felt so good. Don't stop I said. She smiled and stopped.

    I was no longer able to turn around. She bent down to locked some ankle cuffs over the boots attaching them to a lower loop like the wrist cuffs limiting the movement of my legs and feet.

    Looking down at the heels they really looked sexy. She interrupted my thought by cheerfully pointed out how I was now forced to stand directly behind this cute little machine called a spanking machine. She pulled out some nipple clamps and a gag.

    Wait what are you doing I said?

    You will see...

    She grabbed one of my nipples and started to pull and tug on it telling me to open my mouth and when I didn't she twisted tighter and harder until I opened up for her to push this huge gag in me pulling the strap tight behind my head. My eyes opened wide and my jaw stretched to fit this thing into my mouth. I tried to push it out of my mouth with my tongue but I couldn't. How does that fell? Emppff You can hardly mumble with this in your mouth. I thought I must really look silly right now.

    Then she put the nipple clamps on one at a time. It hurt like hell she pulled and slowly release it onto my nipple as I closed my eyes feeling the pain UMMMM... for some reason it made me want to feel my cock getting stroked. Oh that is so sexy she said. I like it when you moan. Shaking my head back NO. She just smiled and did the other one. Nothing you can do about it now darling.

    Now you just enjoy those 5 inch heels for a little while and I will be back to check on you in a few hours. MMMFFF.... A few hours I thought? I am not standing like this for a few hours. My head was screaming “no don’t you dare” but nothing came out of my mouth. She saw me struggle against the restraints.

    You are really turning me on right now you know that? She smiled and gave me a kiss on the cheek rubbing my ass. Lightly tugging on the nipple clamp as the cold chain fell back to my chest. I will be back to play with your cock soon and you better be hard when I come in. I heard the clicking of her heels as she walked out of the room. WFT...? I tried to turn my head to watch that sexy women in her thigh high boots and leather corset walk out of the room.

    I was like WTF did I just get myself into. I now had a little time to explore my situation. Taking a big deep breath, I thought I must look like a total clown right now. Then I felt the pain of the nipple clamps as it ebb and flowed. I tugged on my restraints. Damn. These are good. I couldn't bend down because my balls were locked in place keeping me right where I was. If I could have bent down even just 6 inches I could remove these damn clamps but I just couldn't reach them and trying had the chain swinging back and forth. I was having no problem staying hard at this point.

    I did NOT realize these high heels were going to start to hurt my feet after a while. I would lift one foot to get the pressure off the balls of my feet and the other one would have to take all the pressure. I kept going back and forth trying to relieve the pressure but I had limited movement ability. How do women do this I kept thinking to myself? She makes it look so easy. Minutes were like hours as I tried to manage the pain in my feet, my nipples and my mouth was drooling like crazy.

    I started getting frustrated. I am pretty strong and I thought these restraints can't be that bad can they? This contraption I was locked in couldn't be that strong? So I pulled and twisted on it like hell but in this position I couldn't get any traction with my balls like this. Who the hell thinks of this stuff I wondered? I was really freaking stuck like this and it was turning me on.

    I heard her heels clicking on the floor after what seemed like 2 hours, oh thank God I thought to myself. She re-entered the room. It's been 30 minutes I thought I should check on you dear. She got in front of me and asked, are you enjoying yourself darling? Oh look at you you, you stayed nice and hard for me, good boy. You must REALLY enjoy this? I shock my head back and forth saying NO. Sorry darling but your cock says otherwise. I am going to learn from “it” what you like and what you don't like. That's how easy this is for me.

    You look so helpless and adorable and from the looks of your hard on you love what I am doing to you. Grabbing my balls and squeezing them until I moaned slowly stroking me and moving her long nails up and down my shaft had my full attention.. Yes I think you love what I am doing to you. My nipples and feet were in pain and my cock just needed stroked. I tried to thrust but my balls were to tightly locked in place. She was enjoying my helplessness.

    I think we are ready to start the fun, what do you think? Do you want to wait another hour and 1/2 or should we get started. I shock my head up and down yes yes... YES you want to wait? I started shaking my head no no no. OH no you want to start now? shaking my head yes yes yes. It did not good to try to talk.

    Oh how cute you want to get started. Okay. She reached over and turned on the machine before moving in front of me to watch my reaction. Almost like slow motion, I heard the wisp of the wind from the cain then felt the sting on my ass. as I jerked. Ummph... my body moved tugging on my balls from the blow. My eyes squinted saying all she needed to see that it f'ing stung!!! I didn't know it was going to hurt like this!

    Ok fine, being a man I had to be strong and I can handle a swat on my ass. Pretend like it didn't hurt screw her I can handle this! Then another one came UMMMPH... oh sh1t...Okay wait that hurts, my breathing started to increase just a little. By the 5th one It starting to really F'ing hurt. My mind started playing with me I can't just sit here I have to move there are 20 more of these coming. I thought to myself do I continue to act tuff, I can’t tell her to stop, I can’t say a damn thing, I can't keep letting it hit me in the same place, if I could just position myself up or down just a little out of the way but my balls were held to tightly to pull out of the way. Holding me right where that damn cain needed me to stay. There were short pauses in-between swings. She was fully enjoying this. I was starting to fell warm. I could feel my heartbeat and breathing increasing.

    Another one hit.... Screw this... UMMPFFFF... I was shaking my head back and forth trying to tell her to stop. She smiled and kissed my cheek saying don't worry the pain is only temporary, it goes away. Now walking behind me. Then another one and I know I was tugging and pulling on the restraints. I didn't even realize my feet nor my nipples didn’t even hurt anymore but my ass was burning.

    I tired to stand higher to get to a different position of my ass but it's hard to stand taller when you are already on your tippy toes and the balls of your feet hurt. I shook my head trying to tell her no more. I think I started sweating about now.

    She pushed a button and said were are half way there darling you are doing great. I am so proud of you. I think you are enjoying this far too much. She rubbed her soft cool hands over my ass to cool it down. It felt so good. I thought what a relief maybe we are done. She said now you understand that if this was fun for you it wouldn't work to detour you from using the safe word would it. I shook my head up and down. Good boy... So just remember if you use that word you must really need to use it or we do this again.

    Thinking we were finished she hit the on switch again. umppm... now we we have 13 more left unless you want more.. NO NO NO I shook my head back and forth. My ass was burning, my feet were hurting again and I felt the chain of the nipple clamps swing with each stroke. I wanted to cum so bad.

    Finally the 25th stroke hit me and I don't even remember what I was doing anymore. Each stroke seemed to be more powerful,then the last. I thought for sure my bass was bleeding but it wasn’t. She stopped the machine and the burn was horrible. She reminded me that this was only 25 strokes. Imagine what 50 strokes would be like? She began rubbing some kind of cool cream on my ass and I jerked from the cold but it felt soothing.. She was not hiding how turned on this made her.

    She took the nipple clamps off and OMG I was not expecting that it was going to HURT LIKE HELL when she did. It was far more painful then when she had put them on. I let out a scream into the gag. She just giggled and said yes it hurts when the blood flow goes back into your nipples. Then the other one. it was worse I knew what was coming.

    She unlocked me from what I will call the ball stocks. She asked me to walk over to the chair but I could hardly walk. After a couple awkward and painful steps I decided to get on the floor and crawl a few feet. She instructed me to sit on this big soft pillow just under her new chair. I sat with my legs under me and my ass off the floor. She pulled my hands up to fasten the cuffs to the sides of this chair. It was like I was hugging the chair now. I couldn't remove the boots because of the cuffs locked on. My ass was still on fire and the way I was sitting when she locked the wooden neck brace that left very little wiggle room. I was now fastened to the chair unable to move my head back.

    She crawled into the chair as she explained this was all my fault for making her so horny. Now I needed to do something about it. If I did a good job and gave her a really good orgasm she just might let me keep the device off tonight and have all the fun with her I want. OMG... But it would have to be really really good. She was soaking wet.

    I must have done good because she was squirming in that chair pushing herself into me as she instructed my pace and movements. telling me to keep going as she pulled on my hair and messaged my scalp which felt really good with her long nails. She finally pushed herself back in the chair and my tongue was now out of reach and just took a deep breath laughing. OMG that was so good she said. She just relaxed there for a few minutes messaging my scalp talking to me.

    She let me out and I will spare you the details but she made it ALL worth it.

    We talked and laughed for a couple hours after before falling asleep. I woke up for the first time in a while with a really nice uncaged strong hard on waiting just for her.


    I told you, you can't make this stuff up. I have no idea where this is going to go. But I am wiling to find out.
     
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  3. Cougars Plaything
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    Moving this post from another thread I accidental posted to.
    She wanted me to listen to a hypnosis file that makes her sexy nails a trigger to want to lick her Pussy...


    As luck would have it, I am apparently highly suggestible... SMDH!

    Nikki has this harmless, soft, sexy voice that’s way to easy to listen too. Next thing I know she has me agreeing to the things she says she’s going to do and I am thinking, if she actually does this, it would be pretty freakin hot. So I decided I am going to relax and go along with this.

    I still have no idea what trance is or is supposed to feel like but I’ll be damned if I am not totally feeling these suggestions. I read in an above post where he said there is a release word. I don’t recall anything about a release word. Maybe @Ashley777 can share on that because my GF says she knows nothing about one?

    I am not going into any details tonight because I don’t have a lot of time. She is taking a bath and I am soooo putting her in the mood to going down on her when she crawls into bed.

    My chastity device feels heavy for some reason tonight and my balls are killing me. I need to cum. This thing has been teasing the hell out of me all day.

    She has big plans in the playroom for tomorrow night. I don’t know if to be excited or scared? New packages have been showing up all week and I have no idea what some of this stuff is.

    More when I have time.
     
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  4. Cougars Plaything
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    #54 Cougars Plaything, Jan 10, 2021
    Last edited: Jan 10, 2021
    Short post for now.

    How have I never heard of a product called “good head”? This stuff is fire. Its like crack for blowjobs. This one she used is cherry flavored and she put some on my tongue, it tasted great.

    She generously rubbed it all over my dick and as soon as she put her mouth over my penis it got super warm/hot. Then when she takes it out the air makes it literally ice cold and all I want is to feel her mouth go back down to warm up my cock again. She likes the flavor so she wants to go back down for another taste and this dynamic is insane. She can really play with you if she pauses going back down a few extra seconds and man this drove me freakin wild. I have never felt anything like this.

    She said she can’t wait to try the other flavors! O.M.G. Me either.

    What other great things like this have I been missing out on?

    More later it’s late.
     
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  5. boo
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    boo Long term member

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    what have you been missing out on? True freedom through submission to a beautiful woman!
     
  6. Cougars Plaything
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    I have now listened to both of these hypnosis files a few times. I am really noticing IT. What is IT you ask? Great question and IT is impossible to put in words properly. But I will try the best I can.

    Simply put, IT makes the sight of her nails make me want my face in her pussy doing whatever I can to make her squirm in erotic pleasure and orgasm. SMDH... I mean it really makes me want too! IT causes my chest, arms and stomach to grow week when I see her sexy nails. IT gives me a feeling to take action on these suggestion Nikki used. I am not going to ruin IT for any of you thinking of trying this. IT seems to be growing stronger and she is clearly loving IT.

    This is so freaking sexy. It’s not like I can be around her and avoid seeing the trigger. Nikki really thought this one through from so many angles. No wonder, she says she used this file on her personal boys so you can imagine she didn’t hold back.

    My first couple weeks in the mansion include:
    Beautiful deep conversations and lots of laughs.
    Drawing closer to one another and finding some of our similarities and differences.
    Waking up next to this sexy body locked in chastity is far more difficult then I ever imagined.
    Learning about a product called “Good Head”. Wow.. yes it’s hard to stop thinking about it.
    A taste of what it’s like to not have money be an issue.
    Discovering Hypnosis is somehow working on me.
    Being introduced to and experiencing her playroom.
    Lots to unpack in that one!

    It’s a lot coming at me fast! Not complaining, just sorting it all out.

    more soon.
     
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  7. Cougars Plaything
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    #57 Cougars Plaything, Jan 13, 2021
    Last edited: Jan 13, 2021
    Well my parents are now aware of my live in situation. Not that I need their approval but it’s been a little challenging explaining. Obviously they are wondering WTH I am doing with someone older like this. I get it. It’s a sticky situation but we are falling in love.

    Outwardly we have this totally vanilla looking relationship. No one would know any different. But behind closed doors she loves control. The hypnosis file is like another layer I suppose. It’s giving her another level of control. I make her feel loved by giving her control of the keys to let her decide when I get to cum yet she gets every sexual desire met whenever, however and where-ever she wants.

    She shared 3 special ways I make her feel loved and connected with me. It felt really good to know. I have not reciprocated and opened up fully with her just yet. In some really crazy way her chastity fetish and wanting to control my cock makes me feel loved by her. She acts like it’s hers and it’s cute what she does. Yet this damn thing pisses me off at times for obvious reasons. Some how making me stand in those high heels hurting my feet with a gag and nipple clamps getting my ass spanked turned me on. It’s humiliating to admit this vulnerability. But I know she would love to hear it. Her being able to effortlessly trigger me to want to watch her squirm in erotic pleasure from my tongue Is fire. I have shared some things with her just not these.

    Do I tell her? I feel like I become far more vulnerable if I do.

    We are flying to FL for the weekend. We are going to dinner with a couple of her friends Friday night in Daytona Beach and I have a college friend living in St. Augusta. So he is bringing a couple friends and we are all meeting up. One of her friends apparently became an dominatrix/escort after a bad divorce. She said I would never have known unless she told me. That ought to be an interesting night to say the least. I asked her if they know you have me in a chastity device? Not yet she grinned. Don’t you dare tell them. I am serious, promise me you won’t tell them, that would be super embarrassing for me. Okay, okay, okay I won’t tell them.

    At least I will get out of this thing for the flight.
    I am so ready to get away for a few days.
     
  8. NsToy
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    NsToy Long term member

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    St Augustine?
     
  9. Cougars Plaything
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    Great flight. Landed and went to our hotel. I am used to a room with a bed. Staying in one of theses suits is a whole other experience when traveling.

    we got to the room and put our stuff away. She came up to me and undid my pants. You need to get locked back up. O.M.G? That was not what I was just expecting. After tightening both locks she put the key in the safe and locked it. We went down to look around took a short walk on the beach before getting ready to go out.

    My friends were driving down and we met early for a couple drinks before dinner. She was right there were 4 girls and I had no idea which one was lthe one. We introduced ourselves and the last girl did one of the kiss both sides of you face as she lifted her leg and squeezed my dick the cage. I was started as she said oh, I see I thought her well. She smiled at me.
    ——————————-

    Yes, thank you. Every time I try to post from my I pad I get loads of typos.
     
  10. Open2njoy
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    I guess her friend now knows you’re caged. It’ll be interesting to see what the friend does with that information.
     
  11. Guest 2684
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    You need to tell her how you feel
     
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  12. NsToy
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    NsToy Long term member

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    St Augustine is very close to where I live. The Cellar Restaurant is some nice dining in Daytona if you like Italian. The rack of lamb is really good.
     
  13. Rectrix
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    Rectrix Long term member

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    Yes, you absolutely tell her. Exposing your vulnerabilities and trusting her to take care of you is central to a loving relationship. You didnt share the three things she told you, but you are correct that her lo king your penis and taking control of your release is an act of love, and you need to, must, thank her for that. And of course she should know how much you love to worship her and listen to her cum from your tongue. You are young but very very lucky. Give yourself to her, keep no secrets from her.
     
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  14. Cougars Plaything
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    thanks for the info.
     
  15. Isopropylforyou
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    Tell her your feelings. Everything you have mentioned in your posts let her know.

    Just tell her you want to talk to her alone and then tell her everything. Everything you are feeling, how she makes you feel.. everything.

    Good luck.

    Iso.
     
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  16. Cougars Plaything
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    Sorry for the typos, trying to do this on an iPad sucks. I got interrupted typing out my last message didn’t realize it sent all screwed up.

    So yes, I guess I need to tell her but that feels weird sharing stuff that makes me so vulnerable.

    Let me fix this now.

    Great flight. Landed and went to our hotel. I am used to a 300sq. Ft room with a bed. Staying in one of these suites is a whole different experience when traveling.

    We got to the room and put our stuff away. She came up to me and unzipped my pants. You need to get locked back up. O.M.G? That was not what I was expecting. After tightening both locks she put the key in the safe and locked it. We went down to look around and took a short walk on the beach before getting ready to go out.

    We Uber to the restaurant and my friends were driving down. We are going to meet early for a couple drinks before dinner. Her 4 friends arrived and we introduced ourselves. The last girl did one of those kiss both sides of you cheeks as she lifted her leg. My eyes drifted down as I saw her sexy heel before feeling her grabbing my crotch and squeezing the cage. I was shocked as she said. Oh my... I see I trained her well. She smiled at me and acted like nothing happened.

    I must have turned 6 shades of red. My face felt hot. I was speechless and humiliated. She moved on. We got to the bar and I whispered to Ann I thought you promised not to tell any of them about my chastity? I didn’t she said. Then why did dom just grab my dick and say oh I see I taught her well? I thought I was about to start a cat fight. She started laughing. She did that? YES! OMG that is so her! Please don’t worry I’ll talk with her.

    She came back and said it’s all okay she is just messing with you. It is in her nature it is what she does. She gets leverage on a man and uses it. She thinks you are really cute.

    WTF? Leverage what are you talking about leverage?

    Relax and have fun. No one else is going to know. I told her I have the key so don’t get any ideas as she winked at me. Dom told me if your friends are as cute as you they may have some fun tonight.

    The whole time my mind is messing with me. Is she going to say something when my friends get here? I mean she is hot so it makes it even more intimidating.

    My friends arrived and to make a long dinner short we had a great time. Everyone was talking and laughing they all got along. Usually these situations can feel awkward but not tonight.

    We came back to our hotel lounge for some after dinner drinks. We were all staying at the same hotel. Ann’s nails were seriously triggering me. I couldn’t wait to get her to the room. I cannot even hide it and she is too attentive to miss it. I couldn’t keep my hands off her. I am finding I really enjoy licking her pussy. Watching her squirm in pleasure is so freaking erotic and I’ll be damned if I am not craving to do this to her more and more. This trigger is changing me.

    We all parted ways going to our room as they partied on. I was going to prolong my fun and drive her crazy. If we had neighbors they heard her enjoying herself. It was so satisfying.

    She rolled over and fell asleep.

    Will I get the courage tomorrow to tell her my secret desires?
     
  17. Rectrix
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    Rectrix Long term member

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    You are learning that you are naturally submissive and that you need to worship Ann's sacred pussy. You need to tell her how much you need her leadership, how much you appreciate her keeping you locked, and that deep inside you know are a submissive man.
     
  18. boo
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    boo Long term member

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    yepper ( that's hillbonics)!
     
  19. Cougars Plaything
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    Cougars Plaything Active member

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    Well, this was a fun, crazy, wild weekend. I am typing this on the flight back. Ann is sound asleep. She even looks pretty sleeping.

    She informed me she and Dom had some really good talks. Dom asked her if she could coach us for about a month or so when we get home.

    Does It involve more sex, I asked?

    NO, silly, is that all you think about? Your orgasms won’t be the important part.

    Wait, what? That sound really important I was thinking as she interrupted my thoughts...

    What IS important is what we will learn in the process. Dom can teach us how to reach new levels of connectedness and love for one another. She has quickly identified some of my weaknesses that need to be worked on.

    You do love me don’t you? That’s a loaded question I thought to myself.
    Yes of course.

    Good, Dom is going to work with us separately on video conference once a day for the next month. She will coach you to tantalize, tease and turn me on in ways you didn’t even know we’re possible.

    That sounded fun. I felt pressure growing in my cage.

    She will teach you how to use that warm, soft, sexy mouth and tongue of yours to actually control me in ways you never knew were even possible. You have so much more power over me than you realize and she is going to help you learn to use it properly. This allows you to hold on to your dominant alpha male side while submitting to my dominant side at the same time. I was getting turned on even more as she explained.

    But there is more, she continued, there are parts of YOUR body and mind that are completely unexplored as well and need to be. I have my own work cut out for me. I want to take you to the edge of your fantasies.

    Okay so this was really getting hot.

    She will cover some basic details with you before we leave.

    Saturday night Dom pulled me aside and we went to a separate table for a little talk while Ann and her friends enjoyed their conversations.

    We all have a couple of drinks in us and I was feeling pretty good. Dom is incredibly easy to talk to. She makes you feel really comfortable talking about sex. After some small talk, she asked if Ann discussed her offer with me. Yes, she did, that was really kind of you but I don't really understand what this all means.

    Of course, you don't. That is why we are having this talk now. I wanted to give you some details. The only thing I need to know is if you are willing to really give it your all during this time to learn how to get more control over Ann’s sexual pleasure? You could do anything for 30 days if it were teaching you how to make your relationship stronger and more fulfilling right?

    Without hesitation I agree, Yes, of course. Dom gave me her cute smile. I bet she is really good at what she does I thought to myself. It’s hard not to wonder what she is thinking when you talk with her.

    Good. So we are going to video conference at 7:00 am every morning your time for now. Ann tells me you are punctual so I will expect you to be on time. Yes, no problem but I don't understand what we are going to be doing?

    Of course you don't because it's going to take me at least a month to show you. This is not my first rodeo little boy! We laughed. On the flight home, I want you to think of some of your wildest fantasies. Jot them down. Things That REALLY turn you on. It doesn't matter what they are It just matters that they seriously juice you up.

    I feel really vulnerable sharing that sort of stuff. Of course you do. I want to teach you to embrace it with Ann? You do understand men come to me because their wives refuse to do what Ann wants to do with you? Now man up and do what you need to do.

    I never really thought about that. I could see where that would be true.

    I want your best list and have it ready to share tomorrow morning.

    So here I am about to put my list on paper. I am actually going to try to do this. Wish me luck.
     
  20. Cougars Plaything
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    Cougars Plaything Active member

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    Day 1.

    Dom and I connect via video conference. She makes me feel really comfortable talking to her. After some small talk she asks if I made my list. I did. Good. You are not going to share it with me, you are going to share it directly with A. I do want you to add a couple important things to your list for me.

    1. What Are 5 things you like most about male chastity?
    That I Like? What if there aren’t any? Nice try. 5 things you like and be honest.
    1. It feels really good and arousing to have on at times.
    2. Taking control like this makes me feel like she cares and loves me in some strange way.
    3. When I do get to cum it feels amazing,
    4. I can’t stop thinking about her. Even if I see an attractive women it focuses me on her.
    5. It’s a little private.

    okay done.

    2. What are 5 things you love about Ann?
    I’ll spare you the mushy details.

    Okay I’m done.

    3. Ann loves what Nikki’s file has done to you. Dom proceeded to tell me she is a certified hypnotist, practicing for over 8 years now. It’s one of her biggest passions.

    What the... Wow...

    So you can tame down the effects of this for me? It’s impossible not to see her damn nails and... she interrupted me. NO NO NO! Not so fast. NO she would kill me if I interfered with that. But I would like to possibly help you in some other areas. We will explore over the next few days and see but I have some great ideas i think you may like.

    Would you be willing to spend some time to see if I can put you under now? I promise I won’t do anything but put you under and wake you feeling good and refreshed!

    You can try.

    Totally different experience when the hypnotist can see you, focus and adapt to your reactions. 3,2,1 waking feeling good and refreshed.

    Thank you for that I do believe we will work together very well she said.
    I still don’t know what going under is supposed to feel like. We’re you able to do it?

    It’s okay you did great. We will practice more.

    For now, Ann is eagerly waiting to hear from you. Go share and I will see you again tomorrow.

    Ann was up and ready for her day. When she is all done up she is so pretty it’s intimidating. She had on a really cute short dress and ankle strap heels. She always looks so sexy. I was in my shorts and a tank top. How did it go with dom she enthusiastically asked? Well let me tell you about that. I picked her up and set her on the counter. Ok so I have some things to tell you. Finally she said through a smile.

    I didn’t hold back. I made the decision to just let go and make myself vulnerable... She listened and encouraged me. I answered her questions. I was struggling in my cage as I did. At times it was embarrassing revealing these things. During all this her nails were triggering the hell out of me.

    She gave me a long French kiss caressing my scalp. My dick was trying to swell in the cage. I felt a sense of relief having finally shared these intimate feelings and this kiss made me think she liked what she heard.

    How would she react? What was she thinking? She stopped kissing me and looked me in the eyes saying that was really sexy now you have me all hot and bothered.

    She used a trigger word. I felt it instantly. She said if you are going to get me all hot and horny you are going to need to do something about it, repeating the trigger words a few times as I reached down to find her soaking wet through her panties. I went to my knees and moved her dress up her thighs pulling her toward me. Determined more then ever to make her squirm in pleasure. My face now between her sexy legs. This orgasm came rather fast compared to the others. She must have really been turned on.

    I stood up and we just started talking when her phone rang and she said go shower I need to get this pulling her dress back down. It’s dom.

    Ut oh...

    Walking back to the bedroom I was like, I can’t believe I just told her all this...
     
  21. Cougars Plaything
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    Cougars Plaything Active member

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    Day 2.

    It’s not difficult being on zoom at 7 am with dom when I get woke up every morning around 5 am from this thing. I start thinking I am getting used to this but I don’t know if I ever will.

    Dom small talks a bit to get us started. She probes my feelings toward sharing my fantasies and I speak openly about our discussion. Fast forward and she explains our first experiment.

    This is going to be an excercise for Ann to study your penis and it’s reaction to stimulus. Her goal is very simple. She is to get you as close to coming as possible without letting you come. She is going to learn some very valuable skills in this exercise.

    Starting tonight Ann is going to experiment with stroking your cock. She is going to make you feel really good.

    This sounds fun to me so far. Dom sees the delight in my eyes with a tiny bit of fear. You admittedly like to be teased and Ann is going to tease you while she explores and learns from your reactions to the stimulation.

    Don't get to excited, she is very motivated to NOT let you come, because only one of you gets to come. So you must tell her when you're close. IF you come, she is going to punish you and not some sexy fun punishment like you are hoping, either. Something you'll hate! You remember getting your ass spanked don’t you? As long as you make it to the end of her stroking without coming you win, no punishment. You will be rewarded with making her squirm in pleasure with the best possible orgasm you can give her with your tongue. I am going to,help you with that.

    This is my 1000 stroke challenge. She explained exactly how this is going to work. It will unfold in the post coming.

    Lastly before we finish this morning, I want to give Ann a special gift with your permission. Sure what’s that I asked?

    Would you allow me to put you under and give you a few simple suggestions that help you intently focus on learning to give Ann the most pleasure you possibly can when she uses that sex mouth for her pleasure? I am going to teach you to use your hands and mouth to completely control her. You do like to make her helplessly squirm in pleasure don’t you?

    Sounded fun?

    I agreed to let her do her thing.

    Damn dom is good at this. She started telling me a story and I fell asleep. Then I heard her counting me up. There how do you feel she asked. I feel great! I feel bad I think I fell asleep I confessed. You did good dear. Enjoy your evening.
     
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  22. Cougars Plaything
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    Cougars Plaything Active member

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    Night 2.

    Ann arranged to meet in the playroom. Entering I see her in leather and she looks so damn hot it makes me want her so bad. She is full of energy enthusiastically greeting me.

    Come in my love I am ready to have some fun with you? Let me get you prepared so I can get that cage off of you. Over here come lay down. She had me get naked as I laid down on the padded table and she proceeded to lock the leather cuffs around my wrist and ankles. My dick was swelling in the cage in anticipation of getting out of this thing. She pulled chains attaching the cuffs to the table stretching my arms and legs out to the corners. She then fastened a strap around my upper thighs and just below my abs pulling me tight and secure to the table. I could hardly move. What is up with the straps I asked.

    Oh, you will see.

    She proceeded to remove the cage, There. Now I get to have some fun with you.

    She opened up a white bottle that I could see said Pjur on it. I had no idea what this was. I said wait... what is that as she noticed my arms pulling against the restraints. She laughed. Calm down as she looked me in the eyes and put her soft hand on my abs. You are going to love this.

    She poured what I would learn is a lube all over my hard cock and balls. It was cold at first and very slippery as she rubbed it on me. OMG the smoothness of her stroking me felt unreal. No friction whatsoever created a completely different sensation. That feels so f’ing good. I was rock hard. She smiled and gave me a kiss as she very slowly massaged my clock and balls with this stuff. Have you never used lube before? No, I have never even heard of this stuff before.

    Hmmm. Let’s see how you like it.

    But first, let me refresh you on how this is going to work. You MUST NOT come. I am going to stroke your dick. Tell me when you are getting close to coming. If you come I AM going to punish you and honestly, you are NOT going to enjoy it.

    I am going to stroke your penis as I count to 300 strokes and I want feedback from you on what you are feeling. If you make it to 300 strokes without coming, then tomorrow we increase the number and you get to play again.

    I can tell by how hard your dick is this is totally turning you on. My goal is to work you up to 1000 stocked over the course of the week. Well, I think only a week. Depends on if you can refrain from coming. If you fail, you get punished AND we start back over from 300. This little experiment doesn’t stop until you complete 1000 strokes without coming. So cute isn’t it? She put her soft sexy lips to min kissing me and running her hands down my chest and abs as her nails slowly reached my sensitive spots on my penis and balls.

    Think you are man enough to handle me she grinned

    She triggered the alpha male in me... Yeah right, Show me what you got!
    Seriously she said? You are in no position to get cocky! But I do admire the courage.

    She started counting each slow steady stroke 1, 2, 3... her hand circling my penis smoothly gliding up and down. I have never been jerked off like this before. It felt so freaking good. Her steady rhythm continued getting slightly faster. 25, 26, 27... I closed my eyes OMG that feels so good I could hardly move in my restraints.... 30, 31, 32... That study smooth stroking was starting to really get to me. I tried to block it out by it was no use it felt so good. 50, 51, 52.. OMG. tried to squirm but I had no control whatsoever. It was all in her hands.. I am feeling this amazing feeling in my groin. She keeps her steady pace as I start to experience the most erotic pleasure. 80, 81, 82... I felt it swelling up inside me Ann sh$t seriously... stop! You can get a little closer, I know you can. Trying to move my hips again her slow steady pace was relentless. I’m now tugging on my restraints. I feel it coming close... 106, 107 Stop stop STOP please I’m going to come She notices my head swelling and she pulls her hands off. OMG...OMG...OMG... a sensation flooded my penis and began to subside. My breathing was heavy now.

    Oh, how cute, you were close. Very good, let’s do that again. She waited for about 30 seconds while she kissed me feeling my chest and abs. This was not helping. She added more lube and started stroking slowly steadily again fully enjoying her power and control. 162, 163... okay I feel it. Ann stop! Stop! she picked up the pace a little. OMG STOP! She saw my head swell and pulled her hand back. My dick jerked a couple of times getting so close to ejaculating. WFT are you doing to me? OMG that feels so good. That's so much fun she exclaimed. I could do this for hours, couldn't you...?

    Pre-cum was leaking out of me like crazy now.

    I was reaching my limit faster and faster now. Finally, She went really fast 398, 399, 400... I felt the sperm racing up as it once again stopped. OMG, I made it! I let out a sigh of relief closing my eyes. Good job babe! I am so proud of you. This is a great learning experience. She asked me all kinds of questions. I can’t wait to do this tomorrow. I am going to really get good at this you watch.

    OMG... I will never make it to 1000 strokes I thought to myself. I am screwed.

    She put a cold towel on my groin as my dick started to shrink, You have no idea how horny I am right now, she said. YOU? I replied. She laughed.

    She proceeded to lock me back up.

    These cuffs are very secure but surprisingly very comfortable. The padding is so soft nice. No discomfort at all. She proceeded to crawl on top of me putting her legs on each side of my chest. I could feel and smell the leather of her thigh-high boots and corset. Her nails were driving me crazy right now. I watched as she circled her clit with her sexy fingers. I couldn't take my eyes off them. She smiled down at me and saying the trigger words from Nikki’s file as she positioned herself over my mouth. You are my little pussy slave, aren't you That trigger was much stronger this time for some reason? I grew more and more submissive.

    Those damn triggers how do they do this? All I wanted to do was make her come but I had no hands this time. She moved back and forth up and down using my tongue and her fingers. Her pussy was all over my face. Her movements are so smooth and sexy. The more she moaned the more I wanted to give her an orgasm. It wasn't long and she stopped as her body shook in pleasure. OMG...

    Day 3?
     
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  23. Tieme
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    Tieme Active member

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    Unbelievable this is really a true story! Really nice man!
     
  24. intrigued83
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    Your story from start to now is incredible man. Please continue to share so some of us can at least dream of a situation like yours.
     
  25. caged certo
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    caged certo Long term member

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    Hard to believe of this is real.
    Nice to read.
     
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