Hello there, little sissy of mine.  You look wonderful today.  Your outfit is very nice.  I’ve done an awfully good job of teaching you to dress yourself, haven’t I?  Now you know what styles and colors look good on you, and you make it a point to show off all your good points.  Your makeup looks very nice as well.  I especially like the pink lipstick on you, darling.  Your hair is growing out nicely, too.  You’ve really started to grow into the woman you hope to become some day and I’m quite proud of your progress.  But sometimes, I catch you … staring at me.

Specifically, I see you looking at my big, shapely tits.  They look really good, don’t they?  I’m used to men looking at them, of course.

Men love breasts

Especially a pair as perfect as mine.  But you’re not exactly ogling, are you?  At least, not in the traditional sense.  It’s more like my little sissy is looking at them with something like envy in your eyes.

I know I promised you that when you learned to dress yourself appropriately and apply your makeup well that I would get you your very own set of tits.  You’ve been wearing falsies in your bra for quite some time to correctly fill out your clothes, but it’s just not the same, is it?  Well, I tell you what.  Why don’t you come over here and show me how good you are at breast worship, and then we’ll talk about options for you.

Unbutton my shirt for me, phone sex sissy of mine.  Pull it off slowly and then unhook my bra.  See how they hang so freely and bounce a little when you expose them?  Wouldn’t you love a set that did the same?  Then your sissification would be complete.  Run your hands over them and see how good they feel.

If you had breasts like these, you’d touch them and play with them all the time.

Now lean over and kiss them.  Don’t go straight for the nipple.  Start out at the top and work your way down and around.  Shower the entire breast with kisses before you start to run your tongue over my nipple.  Then, show me how you can suck on them.  It’s important that you learn how to please a woman as much as you do a man … after all, every sissy has an inner lesbian just dying to get out and play!

If you do a good job, we’ll see about getting you your very own set of perfect tits, just like mine.

For an erotic phone session with Mistress Ryan, 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

When you get dressed in the morning, what do you wear to work? Maybe you work in an office and you wear a suit and tie. Perhaps your business is more casual than that and you get to wear jeans and a t-shirt. Maybe you have a specific uniform that you have to wear.

Whatever you wear, you need to be a bit different from the rest, don’t you? You see most men wear regular underwear like boxers under their clothes.

You like to wear panties, don’t you?

How does it feel, crossdressing for your day at work?  You must get a special thrill every time you put on those panties. I know I have a thing for men in panties. It’s very sexy to see a tough guy like you wearing some pink ruffle panties.  Some women, like myself, can just tell whenever we see a guy who has panties under his slacks.  It’s in the way you carry yourself … you stick your ass out more, or have a little extra sashay in your sway.  I always wonder, whenever I see a man hiding his little satin secret …

Do you pick them out yourself?

No doubt you’ve walked by the lingerie store and glanced at the variety of panties available. Thongs, boyshorts, bikini cut… the possibilities are endless. There are so many different materials and patterns to choose from.  Or are you a little thief … and you get them from your wife’s drawer?  You have to be very stealthy so you aren’t caught crossdressing. I bet wearing your wife’s panties is thrilling isn’t it?

Wherever you get them from, you should wear them every day at work. You would be the only one attending the big meeting wearing a purple thong. Or you are making a presentation in your suit with a pair of polka dot boyshorts underneath that show off your ass.  And I bet that makes you feel naughty doesn’t it?

There’s something so subversive about keeping a secret like that. I’m sure it gets that dick of yours nice and hard. In fact, I’m sure you’ve jacked off in those nice panties; your cum soiling them.  I’m sure you pose in the mirror and examine your pretty ass before you put your suit on and pretend to be like everyone else.

Yes I know all about your crossdressing habits you naughty boy.

But don’t worry, your secret is safe with me.

For an erotic phone session with Mistress Ryan, 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

You look cute today in your sissy outfit. I can see your hair and makeup is exactly perfect, just the way you like it. And the way I like it too. But you know what? I want to mess up that outfit. After all, sissies aren’t just supposed to look pretty all the time.

So today I’m going to fuck you up.

Or actually, I’m just going to fuck you.  I’ve got my strap on dildo all ready to go and a slew of strapon fantasies that I can’t wait to share with you.  So many possibilities, so many different strap-ons to use … I almost don’t even know where to begin.  A prissy little gurl like you loves it when I’m gentle and sensual … teasing your body with my light touches and delicate caresses.  You love to imagine yourself as my sissy lesbian lover, don’t you?  I admit, sometimes I like to take things nice and slow but today … no baby …today I’m in the mood for something entirely different.

Just get on your hands and knees.

I want you to wiggle that ass for me. How does it feel, knowing I’m about to screw you so hard that you will be begging me to stop and to keep going in the same breath?  Your cock is hard and you are already trembling. I know I should be nice to sissies like you but today there will be no mercy.  I told you I was in the mood for something a little dark … Sometimes, I just need to remind you that, in the end, a humiliated sissy like you can be fun for a dominating Mistress like me.  I pull down your panties and start playing with your ass, my fingers tracing the outline of your cute little hole. I lube them up and push them in, ignoring your moaning as I go in nice and deep. Wait until you see my cock, little sissy.

There’s no WAY that’s going to fit … is it?

I put the dildo in the harness and sit down next to you. You turn around to see and your eyes widen. The cock isn’t enormously long but it is very, very thick. I know you don’t think that you can fit it inside you. I push your head towards it and you begin to suck it for me. I love seeing that lipstick smear.  Those little tears in your eyes when I thrust too deep … the gagging sounds you make when your lips are stretched too wide … it’s like a symphony to me.  And the orchestra comes when it’s time for that strapon to go in your ass.

Lay down on the bed and spread your legs … Look at how cute you are in that pristine sissy dress with your panties bunched up and your lipstick smeared across your face.  You want to be so prim and proper but I can see your hips grinding already … you want this, little sissy … and I’m going to give it to you …

And that’s what I do. There’s no light strap-on pegging happening here, I shove that cock deep up in that ass of yours and start fucking you hard, grabbing your bra to use as leverage … I know it hurts but even sissies need to learn to take a little pain.

I screw you until I’m satisfied, finishing off by sitting on your face and letting you bring me to orgasm. When I get off you, your makeup is smeared, your panties are ripped and you look like a slutty mess.

Just the way I love you …

For an erotic phone session with Mistress Ryan, 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’ve been watching you for some time. My suspicions arose when you were folding our laundry. Your hands would linger over my panties, folding them so gently. I even saw you caress the lace on them once.  Of course, I thought that meant you have a thing for panties.  But it wasn’t until I discovered a few pairs in your drawer instead of mine that I began to be suspicious. So I set a trap. I laid out some of my best pairs of panties and bras on the bed and then pretended to go out. When I snuck back in the house, I tiptoed upstairs and peeked into our bedroom. You were trying on the bra and panties!

Yes, you’re a crossdresser and I didn’t even know it.

Now there were two things I could have done at this point. I could have ignored it and pretended it never happened. But you were caught crossdressing! You needed to be punished for that, didn’t you? I mean after all, you didn’t even have the decency to buy your own bra and panty set!  So I opened the door and caught you in the act!  Of course you tried to apologize but I know you didn’t mean it. Instead I could see how hard your cock was from trying on those panties. So I decided to dress you up like my little doll. I started with the bra and panties, both pink and very girly. Then I moved on to the stockings and high heels. Who knew men in lingerie looked so cute?  Finally I did your makeup and made you look in the mirror.  Cute right?

I know you wanted to jerk off right then and there

I decided that I was more important. After all, I did just catch you trying on my panties. First you would have to please me and then perhaps I would let you come later. Much, much later.  Yes, I discovered that day that submissive crossdressers can be so much fun.  And now you are my little sissy; mine to play with whenever I want. So bend over please and show me that cute ass of yours.

Now.

For an erotic phone session with Mistress Ryan, 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

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Sissy Training:  Strap On

Hello again, sissy slaves.  Have you been anxiously awaiting the next blog in my feminization and sissy training series?  I’m sure you’ve just been counting down the days until Mistress Ryan’s next blog post, haven’t you?  Well, I won’t keep you waiting any longer.  Without further ado, I give you Mistress Ryan’s Sissy Training School.

Sissy Training 101

If you’re one of those naughty sissies who likes to dress up and be dominated, well, this is the thing for you.  If you’ve been reading my blog or if you’ve spoken to me on the phone, you already know I have a soft spot for boys who enjoy strap on play.  Training a sissy to service me and my rubber cock is just icing on the cake.

I want you to already be dressed in your sissy finery when you call me for strap on training.  That way, we can focus almost entirely on how you will suck and fuck my cock.  Well, except for the part where you tell me what you’re wearing and how sexy you look for me, and I smile and tell you what a slut you are.

Strap On Training 101

Then, you get to get down on your knees and show Mistress how much you know about sucking cock.  The dildo I usually use in my strap on harness looks very realistic.  It has a perfectly formed head and curves slightly upward.  The veins protrude from the shaft, and it’s beautifully shaped.  So show me how you take that cock and suck it.  If you need a little how-to instruction, I will be glad to help.

After you’ve shown me that you can give a good blowjob, then I’m going to put this big dick of mine in a slightly less accessible place.  But I know you–you won’t mind at all.

Penetrating the male psyche

You’ll finally get to do what you’ve wanted to do your whole life:  feel what it’s like to be penetrated.  It won’t just be a physical penetration, either.  It’s a mental penetration because I’ll have worked my way inside your mind in a way that you can’t shake loose of.  It’s also a spiritual penetration because you’ll be laying yourself completely bare in front of me, so that I may use you in whatever way pleases me.

And then, once you’re completely penetrated by me, you’ll be ready for the next episode….

For an erotic phone session with Mistress Ryan, 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