I have an active sex life, however I admit that I can only get together with my sissy cucks and bulls, together at the same time, a few times a month. We’re all busy and to coordinate all of our schedules is difficult.  Most of the men, even the frilly little cocksucking fag sissies are  are successful and intelligent men in their day to day life.  In fact this is what makes the dynamic so special because the moment they walk through my door I call the shots and its all about me. Even my Bulls understand that I prefer to be on top and in charge. Although they don’t call me Mistress or kneel, they do understand that when I beckon, they respond and that they are there to please me.  I also love the dynamic of a strong, intelligent man alpha male that can strip off that everyday facade and relinquish control to me as my cocksucking sissy slut.  The moment they walk through the door and are ordered to strip before me, prepared for inspection, I start to see the shift in their energy. It’s like foreplay as we exchange power and prepare to step into our special world. It’s special and perhaps its better that it happens on special occasions.

I have this black bull named J. He is a successful MARRIED lawyer with a huge 10 inch black cock.  I actually met him at a spiritual conference and found him to be polite and sweet. After a few glasses of wine it was evident that there was a strong sexual attraction between us. I had been with a few black men in the past and really loved the whole interracial sex – white woman, black man, huge cock scene.  His cock is divine. My pussy twitches just thinking about it.  We hooked up and agreed to get together now and then.  He lives in Maryland, works in DC and I’m outside Richmond, VA.  Every now and then our schedules gel and we spend hours fucking.

Through email and phone I explained to J that I was into cuckolding and that it would turn me on to watch a little sissy faggot suck his big beautiful black monster cock.  Surprisingly he agreed without much convincing. Later I learned he had done it many times before and also enjoyed the humiliation of a forced bi cock sucking sissy scene.  I told him about another lawyer from North Carolina, a white macho, “thinks he all that” kind of man. He owns a huge law firm, use to being in control and calling the shots. Little does his peers and friends know that  he looks better in a pink party dress, mary janes, a diaper and wig. (laughing)    I call this little frilly sissy “Mary the Cum Bucket Whore”.

Mary has been dressing since his teen years. Successfully he kept it hidden from his family and even his wife for many years.  Dressing like a sissy and being humiliated helped him relieve the stress in his life and find balance in his world. Still if you asked Mary which he would choose, if the world were a different place, he’d choose Mary.  When I meet him for lunch in his suit and public facade he is tense and unable to focus on me or anyone else. The moment the sissy dress goes on he instantly starts to change.  He is also a diaper wearing sissy which sinks him even deeper into sissy subjugation.  I prefer him this way. In fact I told him I wasn’t meeting him for lunch any more and that in the future he would fetch lunch, wine and serve me at home, as it should be.

I have been fucking with a strapon dildo for a year now. We’ve gone from a small butt plug to an 8 inch realistic cock.  Mary is required to wear a plug and panties 24 hours prior to our meeting, under his suit at work.  Mary also keeps various sex toys, including several sizes of dildos in a special locked briefcase.  Whenever possible Mary is instructed to keep his sissy pussy and cocksucking sissy mouth in good practice. I teased Mary about sucking a real man and it always turned him on, however Mary had never been with a man…until now.

J is a handsome man, very gentle and I can talk to him for hours. I can spend an entire weekend with J without getting bored.  He was able to get away a few days and had some business in Richmond. Of course I wanted to see him. I had also spoke with Mary and asked him if he could serve dinner to myself and a friend. Mary had served lunch to me and my girlfriends. In Mary’s mind this was going to be a girl lunch.  I allowed Mary to think this for a few hours and decided that even though I would have love to seen the look on Mary’s face when she saw J that it would be best to prepare him and give him the consensual option. I love Mary and would never do anything to hurt him, however the thought of it made me wet. So I called Mary and explained that he would be serving myself and a bull. Mary hesitated for a moment and I could even hear him start to breath heavy, struggling with a reply.

“Mary this would turn me on so much.” I told him.

Those simple words pull a lot of weight in Mary’s world because Mary wants nothing more then to please me. He agreed to arrive before J came to dinner and Mary agreed to even cook and serve dinner.

I allowed Sissy Mary to take a bubble bath with me. Together we dressed like two girlfriends on a double date.

Mary impressed me like never before. He showed up at 5pm with bags of food, flowers and wine. Mary happens to be an excellent cook and prepared a sea bass with risotto and homemade mango chutney. Mary set the table, candles, flowers and created a playlist of my favorites- Vangelis , Art of Noise, some R & B. Mary was putting  a lot into this but you could also tell he was nervous. His sissy maid outfit was drenched in sweat.  An hour before J was arrive Mary asked if he could freshen up and change into another outfit.  I wanted Mary to relax and I was proud of how he was handling things. The dinner, the wine, everything simply perfect. I allowed Sissy Mary to take a bubble bath with me. Together we dressed like two girlfriends on a double date. I wore a long black satin negligee with a slit all the way up my leg and a pair of black patent leather mules. Mary wore his sissy bambino diapers and a black and white ruffled sissy party dress. The dress was ultra short so I suggested a pair of rumba panties over the sissy diaper. He also had white lace stockings and a pair of high heel mary jane shoes.

The doorbell rang and I sent Mary to answer. Mary turned, looked at me and his lips trembled.

“Its ok honey, I’m right here. Go answer the door.” I told him.

Mary brought J into the den and I could tell Mary was surprised not only that he was black but what a stunning specimen of a man he is. Mary fetched us wine. When it was time for dinner Mary served us in an elegant fashion. While we ate dinner we flirted and talked. It was so romantic. I had Mary kneel by my chair as I fed her my left overs.  Several times through the meal I made it a point to lift Mary’s dress and reveal his panties and diaper. J chuckled and Mary blushed.  We decided to have dessert by the fireplace in the den. Mary brought fresh berries and REAL whipped cream because he knows this is my favorite. I also love putting berries and whipped cream on my pussy for Mary to eat so maybe Mary had a hidden agenda? (laugh)

We ate the little cakes, berries and cream. Mary knelt by the table awaiting his next command. I decided it was time for Mary’s dessert. I pulled J’s cock out of his pants, all 10 inches, covered it in whipped cream and instructed Mary to lick it off. You should have seen how delicious that that beautiful black cock looked covered and whipped cream and then watching Mary’s pink tongue lick it off.  In-between stroking and sucking I popped raspberries into Mary’s mouth.  Together Mary and I licked the berry juice from his cock.

I couldn’t stand it any more.  My pussy wanted to eat that big black cock.  I took off my panties and mounted him cowgirl style. I had Mary get between out legs and lick my clit while I fucked J.  His cock pressed against me thrusting in and out of my wet swollen pussy. I ejaculated all over sweet Mary’s face and she moan deliciously. With my hands planted firmly on J’s thighs I moved back and forth milking that black cock until he shot his creamy load into my pussy. I then threw Mary down onto the bed, smashed my pussy on his face and made him slurp out every single drop of my cream pie.

After we all sat around talking and having a great time. Mary massaged our feet and gave us back rubs. At one point J bent over and kissed Mary on the lips. I never seen Mary glow so much! We went to bed with Mary sleeping between us. She was a happy little slut. Next time I’ll make sure Mary gets fucked with that big black cock but I think he needs some more training to handle that monster black cock.

I’ll keep you posted. make sure you’re subscribed to my blog for updates.

Love,

Josephine

For an erotic phone session with Empress Josephine, call 800-601-6975

Must be 18+
Calls are $2.50 per minute, with a 10 minute minimum
Discreetly billed to  your credit card
http://ratemycall.com

I’m sure many of you get a deep sexual welling inside where you find yourself submissive but as soon as you orgasm the urge dissipates. While your cock is hard you feel sooooo submissive to the point that your cock twitches but when you cum it’s all over or at least until the next time.

There’s another problem. While rock hard you make promises and then when the session is over you feel guilty about calling again, right? In your attempt to make it real you agree to a follow up assignment or anything else I suggest as long as you can satisfy your sexual longing. You never seem to follow through because the truth is the urge has left and back to life as usual.

It doesn’t have to be so complicated. I can totally understand how you feel because on the opposite end of the spectrum I go through the same thing, although I am naturally dominant in my sexuality and personal life, I am more “ON” when my dominance is seduced. Why can’t we agree to take make that fantasy as real as possible and just pick up from where we left off the next session? It’s really pretty easy. Just pop me an email be honest and we’ll engage each other in a hot ass femdom phone sex call. When you do your next session send me another email and outline what we did in our previous session and that this next call is a follow-up. Simple.

Now if you ARE truly interested in an actual slave  or sissy training program or cock control then you should convince me you’re sincere. Simply following up with an email to request an assignment and then complete the assignment. Although its not expected tributes/tips are always very much appreciated. After a call stay on the line and you’ll bounce back to dispatch or call back. Just tell her that you’d like to leave a tip for Josephine and the amount. She’ll email me and let me know. As we progress through calls and assignments you’ll learn more about the dynamic of dominance and submission. When you’re ready you’ll go on to introduce a girlfriend, wife or seek out a lifestyle relationship with a dominant woman.

Regardless of the reason why you call or what makes you explode, I’m here to help you have the best experience you can have during a phone sex call. In fact it excites me to weave this beautiful plan to rock your world to the point that you are addicted to the sound of my voice and the sexy things I can teach you. (wink) So lighten up and let’s have some hot talk and earth shattering orgasms.

Please subscribe to my blog for updates.

For an erotic phone session with Empress Josephine, call 800-601-6975

Must be 18+
Calls are $2.50 per minute, with a 10 minute minimum
Discreetly billed to  your credit card
http://ratemycall.com

There was an interesting topic started at the Sissy School forum click here about sissies and cuckolding. The first part of it is a bit slow and then it gets deeper after a thought provoking reply from a user. I thought it would be great to have my intelligent subscribers join in on a new conversation. You are free to post comments below and or post in the forum. Posting in the forum requires registration.

So I am starting a new topic for this NEW discussion called:  Gender Journey ~ Complexities and Manifestations

The exchange I am looking for is gender exploration and the differences between a sissy, crossdresser, transvestite, shemale, etc. I don’t believe that anyone clearly defines this and that there are subtle differences in each person.  This is why I’m curious and want to know how it makes YOU feel and the activities you engage while in “mode” such as how you dress, what you masturbate to, humiliation, forced bi and cuckolding.

Personally I have always felt that there were “other” gender’s and that genitalia has very little to do with how we manifest sexually. I think a lot of people fight it, stay in the closet and those that are brave enough to take the first steps might struggle and fight it.  This is why role-play, humiliation, forced bi, cuckolding and other fetishes become part of it.  I agree it’s hot, kinky and no one loves this more than me, however I can’t help but wonder if it’s a type of “permission” to release this inner person inside of you.

There’s more I want to say but I’d really like to do this in the forum and an intelligent inactive exchange. What say you?

Gender Journey ~ Complexities and Manifestations

click the link above to join in on the discussion.

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I needed a partner in crime…lol- I mean help training all these sissies so I’ve asked my friend Mistress Ann from Sissy Style Magazine online to come give me a hand. We are going to plan some special events together such as tea parties, outings and more. Auntie Ann and Nanny Josephine will soon offer mild to wild sissy training. Are you up for the challenge?  You can even do a two mistress call with us to get a jump start on your sissy training. I would LOVE to show some of you off to Auntie Ann and let her see what a pretty little sissy you are. We can do this on the phone or in text session. Maybe you’ll turn on your cam and let Nanny (or Mommy) Josephine make you act pretty in front of Auntie Ann?

Some come on darlings and let’s have some fun.

• Is he seducing my masculine side? The aggressive and dominant woman that wants to make him my bitch slut and own that man pussy?

• Is he looking to explore his feminine side? I can help him dress like a woman; feel like a woman and how to fuck like a woman.

• Is he longing for subjugation? Nothing emasculates a man quicker then to be penetrated by a woman with a MUCH larger cock then his.

Whatever reason you love strap-on dildos let me dissect you and explore the very essence of your desire and then take you on a journey you’ll never forget.

Here are a few great phone sex ideas for strap-on dildo play:

1. Forced  Emasculation – This can involve crossdressing or sissification.  I am your wife, girlfriend or new neighbor. I catch you doing something naughty, maybe stealing or smelling my panties. I humiliate you by forcing you to act like a sissy and or bend over and take it like a bitch.
2. Be My Lesbian Lover – Ever wonder what it would be like to make love to a woman while BEING a woman? This fantasy involves dressing you in sexy lingerie, making love to you like a woman and penetrating you or maybe YOU’re wearing the strap-on and penetrating me.
3. Slave Slut Training – Because you are SLUT property you must be treated like a dirty little whore.  This means dildo sucking and ass fucking with a collection of strap-on dildos. You’re sole purpose in life is having your whore holes penetrated.
4. Sissy Wife, Sissy Slut, Sissy – If you’re a sissy wife then obviously you must take it in the ass-pussy-nasty girl hole- money maker or whatever I decide to call your holes. I’ll fuck them all!