My Boss is a Crossdressing Sissy!

cross dresser phone sexI went over to my boss’s house to take him some paper work to sign.  It’s a standard thing, as he has a home office.  What wasn’t standard, was that he didn’t answer the door when I knocked.  I have a key, so I let myself in and put the paper on the desk in his office. My boss was still nowhere to be seen, and I was sort of worried.

That’s when I heard a noise from the room at the end of the hall.  I peeked in the cracked door, and to my amazement, I saw my boss with his earbuds in his ears, eyes closed, dancing around his bedroom.  He was completely dressed in white silk and lace – from his stockings to the teddy to the tiny little robe.  His face was perfectly made up and he had on a long blonde curly wig.

You should have seen his face when he saw me standing in the doorway. I guess he’s no longer the boss, huh?  I run the show now! After snapping some pictures for safe keeping, I discovered a huge strap on in the nightstand by his bed.  I slipped it on and really showed him who owns his little sissy ass.  Having little bitches who once thought they were powerful is the best part of being a Mistress.

So, all you little cross dressing sissy bitches give me a call! We have so much to discuss.

Kisses,
Tammy

Tease and Denial Phone Sex with Mistress Tammy

Tease and Denial Phone SexJust because you call me, doesn’t mean that I’m going to allow you to cum.  There is a misconception among my sissy followers where they think they are entitled to an orgasm because they have spent their money to call me.  This, my sweetlings, is incorrect.  There are many, MANY calls that are strictly tease and denial phone sex calls and until you’ve earned your orgasm that is all they will be.

I honestly get off knowing that I control your cock. I know that all of you sissy boys crave that kind of control.  Occasionally, though you slip and forget who is boss.  For example – one of my sissy callers  tries to argue with me about his sissy assignments.  He is under the impression that our relationship is give and take.  I know, I know – most of my sissy boys would NEVER disobey or argue, but not all of you are trained.  He is in need of sissy training, badly. He whines, and eventually complies with my requests/demands, but his insubordination does not allow him to have an orgasm.

You Need Training

If he continues in this manner, he will be put in chastity. As of now he is just teased to the brink and then not allowed to finish.  We talk about all the things that get his panties wet – sucking cock, being a cuck, being used by my real men – and the entire time he’s stroking.  Then, as I hear his breath quickening and his voice shaking, I make him stop.  No more stroking, no more teasing, no more sexy talk.

I’m fairly sure he cried the last time we spoke.  I explained to him why he was being punished, and why he wasn’t allowed to cum.  Hopefully, he will learn for the next call – but if not – there will be more tease and denial phone sex in store for him. 

Forced Bi Phone Sex

Forced Bi Phone SexHi cuties! I know I have a soft spot for sissies, but sometimes you boi’s come to me with such a small amount of training, that my brain wants to explode!  You are running amok, thinking you can make your own rules and just do whatever you want. Well, I guarantee that is not how this works.  Being a sissy is more than just prancing around in panties. It’s about pleasing me, and nothing pleases me more than seeing you suck cock.  What? You don’t like that? Well, that means we are going to have forced bi phone sex then, doesn’t it?

There is so much more to life than licking my pussy and getting me ready to fuck real men.  You aren’t just my fluffer.  That mouth belongs to any cock I see fit.  My trainer has the perfect dick for you to start out on! That’s right, you’ll have big, 9 inch big black cock to pop your blow job cherry.  You’ve eaten his cum so many times out of my pussy, and now its time to get it straight from the source!

Now, get on your knees you little panty boy slut! Open your mouth wide and take that big cock down your throat. Don’t you just love how that dick tastes. Now lay on the bed with your head hanging off so he can get it all the way down your throat. It’ll make it easier on you and you won’t gag as much.  Don’t disappoint me, slut.  Make me proud and show everyone what a good cocksucker you are!

 I love forcing you to try something new! Before you know it, you will be craving cock like a sissy is supposed to.  So let’s get your sissy training started.  I don’t mind making you have forced bi phone sex over and over again until you get it right.

Sissy Loves Massage

Tease and Denial Phone SexI have a new favorite sissy and he loves for me to be his massage therapist! We will call him “B”, and he’s my new favorite play thing.  It’s so much fun to play with him, especially when he keeps those panties on!

Today, he showed up in the massage parlor and requested me! He was dressed in a business suit, just arriving from work. I could tell he was super tense, so a massage would wonders for him.  B was instructed to change behind the screen, and he came out with a towel wrapped around his waist.  I was shocked with how built he was…and how smooth.

B had shaved and waxed every inch of his tan, muscular body.  Being a massage therapist, I see all shapes and sizes, but I get great pleasure in rubbing my hands over all those muscles and smooth skin. Rubbing my hands together and coating them with oil,  I started at B’s shoulders and worked my way down his back, massaging all the knots out.  As I got to his waist, I slid the towel down just a bit so I could massage those glutes.

That’s when I noticed them!

Those lacy pink panties were peeking beneath the towel.  This totally changes the game for me.  I knew he was a little sissy now, and needed some training.  Pulling out the 8 inch strap on that I keep under my table for such an occasion, I continued to massage him so he wouldn’t know what was coming. He was so surprised when I slid it in his mouth.  I wanted to see what a good cock sucker he was…and boy was that sissy good! He got it all nice and wet before I fucked his pretty little ass and made him squirt in his panties.

I just love my little sissy panty boys! Y’all are so much fun! Don’t let B be the only sissy I torment today.  Pick up the phone and give me a call.  I’m waiting with my strap on!

Big Tit Phone Sex with Mistress Tammy

Sometimes, you just need big tit phone sex to get that cock rock hard, don’t ya? Well, if huge knockers are what get your motor running then give me a call. I’ve got a perfect set, ready to fuck you with!

Tease and Denial Phone Sex

 

I would love nothing more than to bury your face right between them and press them together.  Motorboat me a little, won’t ya? It would be a shame if I press them against your face so tight that you almost pass out…but that cock sure does stay hard! My nipples are super sensitive, which is unusual with us bigger girls. They get super hard and my pussy just drips when you play with them.

My favorite thing to do is to lay on my back with you on top of me.  I’ll press my titties together and you can slip your big, hard dick right in between them! Don’t forget to spit on them first and get them all wet and slippery.  Now fuck those tits like you’d fuck my little pussy.  I’ll suck the tip of your cock when it pokes through. Does that feel good?

I want you to cum all over my nipples and face. I’ll press them together and you can jerk that rod off until you are showering me with your jizz.  Isn’t that just the hottest thing ever? Don’t my tits look amazing covered in your white, sticky cum?

I’m so horny, and ready to have big tit phone sex with you.  Give me a call and let’s play!  855-535-0207