Tag: Domination phone sex

A Different Type Of Cuckolding Session

Cuckold phone sex

Gerald is such a dirty little man.  Him and his wife have been having a Cuckolding relationship for a very long time.  I hadn’t know that because it isn’t something that comes up in polite conversation.  I did mention to his wife my new found love of BDSM play and how I have been exploring different aspects of it for a few weeks now.  She then told me about the Cuckolding situation, I was pretty well surprised.  Heidi told me that Gerald was a very loving provider, but since she was so much younger than him there were times that he couldn’t perform due to him having bouts of Erectile Dysfunction.  Gerald felt badly because he couldn’t perform right, so they worked out a system that she could be with younger men, with the caveat that he be in the room.

Over time this arrangement turned into a Cuckolding relationship.  They both enjoyed it.  Good for them.  Heidi then asked me if I would like to fuck her in front of her husband.  To say I was surprised would be an understatement.  However, they are both good friends so I said yes.  I bought a harness and a few different types of attachments for the harness. 

I have to say, getting behind this gorgeous younger woman as I plunged the strap-on into her beautiful pussy was amazing.  Seeing the effect it had on Gerald was also wonderful.  They really got into the whole role-play.  She was telling him how much better a lover I was than him, how he could never satisfy her the way the other men and I can, how small he was, how pathetic he was.  We played for a couple of hours.  Right before I left we sat down to drink a few glasses of wine.  Gerald told me that what Heidi and I did was one of the most arousing things he had ever seen.

I am thinking that this might become a regular play time with my two dear friends.  

Short Dick Man

Domination phone sexI had sissy short dick boy come up to me in the club begging for my abuse. I ignored him at first because I love to hear a sissy boy beg for my attention. When I did decide to notice him I told him to whip out what he had packing between his legs. He did and I needed a fucking magnifying glass to see it. I laughed my ass off he was hard and no bigger than my pinky width and length. how fucking pathetic! It was the most useless excuse for a dick I have ever seen. I grabbed a hold of it and started pulling on it. His balls were the size of grapes dried up grapes. I took some floss and wrapped it around tightly between his grapes and pinky dick. I am going to do him and the world a favor I am going to castrate his poor excuse of a dick.

Sexy cuckold

Roleplay phone sex

Roleplay phone sex lets me relive sexy, hot kinky shit that has already happened. So the past month my boss’s wife started working with us. As soon as I met her I was instantly attracted to her. Not to mention my boss has flirted with me since I started last year. We have fooled around a couple times. Well,, he had always told me that he would love to watch his wife get fucked by me. Having us two would make his dreams come true. His wife came into my office letting me know about a meeting I told her to come to sit with me. As we talk I imagine her bend over my desk fingering her pussy ad her husband walks in on me eating her sexy little pussy, he soon joins. Well, I explained to her that she was beautiful and I would love to play with her. I would get some wine and I would make her feel so relaxed and amazing. She was caught off guard and bent over my desk and kissed me and told me to meet her after work in her office. So, I did I walked in so excited I had my sexy little panties in bra on and they were both waiting. They had this sexy little three sum planned for quite some time I believe. Her pussy tasted so sweet as my boss pounded away my cunt.

Playing Dress Up

Forced feminization

I met Gregory ages ago, he was friend’s with my then Husband.  When he asked me out to dinner I said yes, he is a very handsome man, retired, a widower, and very well educated.  I really enjoy the younger men, but I also enjoy a very educated older man.  We had good conversation, a fabulous meal, then spent time laughing over after dinner drinks.  When he took me back to my house I already knew I was going to invite him in.  

We ended up in my bedroom, I excused myself to freshen up before we fucked.  When I came out of the bathroom I caught him holding one of my bustiers up to himself as he looked in my full length mirror.  I stood there a little shocked, he was twisting his body side to side, I think that if I hadn’t come into the room right then he may have tried it on.  I cleared my throat, he dropped the bustier.  I asked him what he thought he was doing, he said nothing.  

He made a move toward the bed but I stopped him.  I walked over to where he had dropped the bustier and told him to pick it up.  He made a fuss, grabbed his clothes saying that this whole situation was ridiculous.  I told him to pick it up with a sterner tone.  He just looked at me.  I sat down in my chair and said it again, never taking my eyes off of him.  He put his clothes down and picked up the bustier.  I told him to put it on.  He was shaking as he struggled to put it on.  I told him to grab a pair of my stockings and to put them on as well.  His cock was rock hard.  He asked me if he looked pretty, I started to smile.

I asked him if Greggy was a sissy.  He giggled.  Oh this was going to be fun, and it was.  I turned him into such a little sissy slut that night.  When we were done playing I told him that they only way he could leave is if he left in the lingerie.  It took some doing but that is just what he did.  He told me that he bought some things that would actually fit him correctly and wanted to know if we could set up a play date again.  I told him that I look forward to it.  

Sensual Domination

Mature phone sex

I decided to try something a bit different this past week.  I was invited to be in on a friend’s session she was having with one of her submissives.  I have always been interested in what she does, and how.  One of her subs agreed to have me sit in on a session.  I have to say, I very much enjoyed every single minute of it.  The way she used the tone in her voice, the power she wielded over him, the way he melted with each of her spoken words.

She told me that there are different forms of Domination, I told her that I know. lol However, I never seen a Pro engage in that sort of play, that is why I wanted to watch.  They went into a more sensual Domination session, her submissive was uncomfortable with that so she phoned another sub and told them to come over.  As the first sub laid at my feet, the other one and her had a rather erotic Sensual Domination play time.  I have to say, I was extremely horny from watching them.  The sub at my feet could tell and he asked if he could be of service, I said no.

After I left I made a few phone calls and found someone who I could ‘practice’ on.  They came over and I have to say, by the end of the two hours I think I had really gotten the hang of it.  Having complete control over him, his cock and all of him was intoxicating.  I was a lot more horny then I was before.  After he left I called an agency that I have used many times to have one of their lovely men come over and fuck me until I came.  Since I was so damn horny it didn’t take long, but I wanted more than just a quick fuck.

We spent the afternoon together.  I told him about the Sensual Domination thing, he told me about one of his other Janes that was into that.  He said he liked it too, but he didn’t like it with her, he said she wasn’t really that good at it.  I asked him if he would like to try it with me some time, he said he would.  Now I have a ‘date’ set up with him for next week.  I think I am going to enjoy my Sensual Domination journey.

Cuckold Phone Sex Mistress Doesn’t Play!

cuckold phone sex

I really thought you would learn to obey your cuckold phone sex Mistress this time!

My Micheal Kors purse you sent is a fucking Knock off, Designer gets my pussy wet. I should have known better than a man who has a clit for a dick. Fuck I even let you suck Dwayne’s cum out of my ass. What do I get a fucking Insolent micro dick bitch! Oh, But your shrinky DInk got off to watching Dwayne fuck me so hard I almost cried from how big he was. My ass gaped for you by that Python of a black cock of his. I even asked you if you liked watching you sweet young Mistress take Nigger Cock all night? You fucking loved it! And the disrespect as Mistress I get Is a fucking Knock off! How am I supposed to show my Face at school, when I told all my Girlfriends how smitten you were and what a fucking pay piggy you were and Your dick has never Touched me. You have 24 hours to make it right or you will never see my ass fucked or get to eat me out after I am full of cum again!  I do Not play, I swear you will be stuck watching female domination porn, I will Ruin You!

Surprise for you

Great blowjobs  I love giving great blowjobs. My Co-worker and I went on a brunch date yesterday. It was nothing out of the ordinary. But, something seemed different. As I went to pay for my bill he picked it up for me. He wanted to pay for me it was nice, but it was unexpected. He asked me out knowing he had a wife. I refuse to make any romantic connection with a married man, also one that I work with. He is very attractive, but I just couldn’t. I told him that he was wrong for doing that. We eat together yes, but its strictly business. I guess until now. Well, this morning I woke up with flowers delivered to my door. Knowing it was him, I sent them back. He must have asked my assistant what my favorite flowers were because he knew. Daisys. How sweet right? I thought.  I made it to work and he was sitting in my chair at work. He told me to lock the door. I proceeded to shut it and let him confess his love. He told me that since he met me he had always admired my work and enjoyed my smile. I couldn’t help but blush. I couldn’t hold back anymore. I got down on my knees giving him the best head that I ever gave. He came in my mouth and swallowed it all.  Next time I hope to be bent across my desk with my skirt pulled up above my waist.

CJ’s Training

Domination phone sexDomination phone sexCJ is a sweet girl and one of my best students I have ever had. About a year ago she came to me looking to learn how to be a good, commanding Mistress to all the sissy and small dick boys around. I took her under my wing and she has absorbed everything I ever showed her. I still make her submit to me. Every good Domme was once a bitch herself. But when it comes to the boys she does great. With Nathan small itty bitty thing he calls a dick. (Laughable!!!) She wields him like a sword. He has what we call “subspace” which means he is totally infatuated with her. CJ happiness is all that matter to him. That is exactly where you want your boys to be. CJ is not done in her training and I have so many more things I still need to teach her about being a Mistress of the boys.

Deny Her Nothing

Cuckold phone sex

It is amazing what money can do.  The places you can go, the things you can purchase, and the sexual situations you can find yourself in are unending. I have a friend who is much younger than her Husband.  She married money, the only problem being a young beautiful thing and marrying a man who is much older than you is his dick.  Old dick is not a good thing at the best of times.  Men seem to think that if they have the money they should be able to control the sex, in some instances this may be the case, but for the most part this just should not be.  Especially if that old dick is attached to a Bastard.

There was a dinner party recently, it was particularly boring. that is, until I found Jaquiline crying in the drawing room.  I went to her to ask her what was the matter.  She told me how much her Husband wanted sex but he was too rough with her, that he never lasted long enough to please her, plus his size was not sufficient, she simply did not know how much more she could take.  I told her if it was truly that bad she should divorce him.  Jaquiline stated that she couldn’t because she would have nothing, she signed a pre-nup.  I then told her to Cuckold him. 

She had no idea what that meant.  I explained it to her.  She blushed like mad.  She said she could never do that.  Her Husband was too bossy, he would never go for it.  She said that she would just have to make due.  I told her she was being idiotic, nobody should go through life unsatisfied and miserable.  Two days later she was at my door asking me to teach her.  

That afternoon I invited two Gentlemen over to help us out.  I had her sit in the corner of the bedroom as I set up the scenario for her.  Edward would play her husband, and William would be her “Bull”.  Apparently she was under the impression that I was going to be the one playing the wife, she was somewhat shocked when she found out that she was going to be the wife.  Edward was older, William younger and quite attractive.  Edward played the part of her Bastard of a Husband so very well.  It took a while, we had to keep stopping so that I could give her direction.  By the end she was being fucked like a whore as Edward knelt beside the bed, his eyes at the right level so he could watch William’s thick cock slam in and out of his pretend wife.  The more she relaxed, the more verbal she was with Edward.  It was a sight to behold.  I loved watching the whole thing unfold.

Once the first session was over she was more sure of herself.  Of course she would have to start slowly with her lump of a Husband.  I have known him for a very long time and he is a certified asshole.  She has her work cut out for her, however, with my guidance and with more and more practice he will not be able to deny her anything, whereas she will deny him everything.

Training The Worker

Mature phone sex

Having work done on My house is always a pain the ass.  Things cost more than anticipated, there is always noise, and the mess is just insane.  This time however I was extremely happy with the work that was done.  Not only was the craftsmanship lovely, the bespoke pieces I wanted to incorporate were exquisite.  I was thrilled.  I was even more thrilled when one of the guys who did some of the custom pieces showed up.  The basement has always been a sore spot.  I just never have gotten around to doing it since I moved into the new house.  After going to a friend’s house and seeing how hers looked, I simply had to have mine done.  You know us older Women, always trying to outdo one another.

When he arrived I fell madly in lust.  He was just mind blowingly gorgeous! I had to have him.  He didn’t know it yet, but he would be My pet by the time I was done with him.  I made My intentions well known.  He pretended to not like My advances but I could tell he was very interested.  When his buddies were around they would tease him about Me.  I didn’t mind at all.  If W/we cannot laugh at ourselves then who can W/we laugh at? Nobody.  

There was a time when I had him alone for a few hours.  I just simply took most of My clothing off then walked up to him.  His eyes went right to My tits.  I grabbed his hand and placed it on the front of My panties.  He didn’t pull away at all.  I knew then that I had him.  He went to stand up, I told him to stay right where he was.  I lifted My leg up so that I could place My foot on the ottoman then told him to worship My pussy.  He didn’t know what that meant, I had to direct him.  He followed My every command.  After he had tasted my cum on his tongue, I placed My foot back on the floor, turned, then walked away.

His cock was stone hard, I could see the outline of it through his work pants.  He didn’t move for a very long time, then after a bit I heard him get back to work.  During the time he was working here I would have him do the same thing.  Please Me over and over again, but never allowing him any release.  Now that the work is done, he still comes over.  He is learning, of course he makes mistakes, all do.  He has to be trained in the right way, however I can see him going really far.  Especially with My guidance.