Category: Sissy Training Phone Sex

Trapped Sissy Fantasies

Do you fantasize about dressing up in women’s clothing?  Good! I can turn you into a sissy faggot unlike no other.  I love beautifying and turning strong manly men into a fucking sissy. I cant wait until I make you  into a slutty bitch.  After I’ve incest sex2dressed you for the part I take you to a hotel room and let the fun begin.  I have just the right situation for you.  Those two men down the hall they are just itching to fuck a sissy faggot  like you. They paid me well  just to let them stick a cock in you. They are going to want some nasty sex and won’t take no for an answer.  I sit back and wait for the fun to begin.  I get off  watching  you suck your own ass juices off their dicks. They plunge in and they stretch out your tiny little hole.  Don’t you worry your pretty little heart.   I’ll take good pictures for a reminder or for future blackmail when you don’t follow my directions.  I love taking control of every situation and this is no exception.  When these men are done I will find a few more to make you a complete making sissy for the night.  I suggest you hurry along and get dressed for your big event as time is short there are horny men outside.  Comb your hair, freshen up your make up, put on some bright red lip stick check your hose for runs and please don’t forget to grab the lube.

Finally the door opens and the fantasies begin. incest sex1

 

Naughty Secretary Phone Sex: Sissy Training Holiday Party

I have a part time office job. I don’t have to work. I don’t even enjoy working, but this office job is unique. I am paid really good money to simply give “dicktation.” I have no real skills. But, when you can deepthroat massive cocks, you find yourself in high demand. So many women just can’t swallow a huge shaft. Since I am a total size queen and won’t get out of bed for less than 8 thick inches, many well hung corporate executives need my special skill set to get through a grueling work week. I have been the big cock blowjob secretary at an all male law office for a few years now. The smallest cock in the firm is 10 inches; so I would work for free, but I am not going to complain about a 6 figure income a year to suck real men off.

Every year they throw a wicked wild holiday party. They hire male strippers, bring in a celebrity chef and bartender for catering, even hire a few pretty whores to help entertain the guests. Besides the whores and myself, it is an all male, all well hung party. No sissies or tiny dick losers allowed. Well this year’s party was the kinkiest ever. Somehow, two tiny dick losers snuck in. I guess they had huge wallets and thought that would make up for having clit sticks. My bosses recognized that I am too hot as were the hired whores to service anyone with less than 8 inches. No amount of money will make me lower my standards.

Being the mean size queen I am, I suggested we sissify the girls who failed to measure up. I love humiliating tiny dick losers, especially ones who do not know their place. The rented whores joined me. We got them all prettied up and made them suck off the male strippers. Dressed them like pretty sissy Santa sluts.  Even had them bend over and take it in the ass by the real men. I  put on my big red strap on and fucked them like the  sissies they were. The strippers enjoyed humiliating  the sissy fairy fags too because they thought they were better than the rest of us simply because they had money. At this office holiday party, big cock was the only thing that mattered. Last year’s party I was sucking big dick and getting fucked. I did enjoy some of the hot hung strippers, but I spent most of the party training the new sissies to suck cock and take it in their back door pussies like good sluts. Even made them  drink cumnog! Got to get sissies hooked on cum early on in their training.

Even though the office Christmas party was different this year, it was still wicked kinky fun. Only thing I enjoy as much as a big hard cock in my holes, is putting tiny dick losers in their place!

Caught Red Handed

Do you like being a sissy boy?  where do you keep that little secret bag of feminine clothes you’ve gathered out of site from everyone?  Well there it is under the bed. Let’s just take a look of what’s inside shall we. Oh what do we have here your grandmothers panties, your wife’s bra, let’s not forget your sisters silky nitey . Quite the sissy faggot are you.  Why don’t sissy phone sexyou take a few moments turn on that cam and model those items for me let me be the judge.  Nice I like that, spin around and let me see a full view.  Now let’s continue going through the sissy faggot bag of yours.  Hmm I see a dildo, butt plug and some lube, I can see where this is going to go.

Lock the doors turn on the cam more I want to see you suck that dildo.  Suck it like you mean it swirl your tongue around it. That’s right just like a good faggot does.  Now while you are sucking that dildo I want you to get on the floor and lube up that butt plug, suction it to the floor and lower that sweet ass on to it. How does that feel, I can see your cock is responding nicely in those granny panties.  It’s ok if you continuing suck to touch your cock, but only through those panties.  Oh yes look at that pre cum ooze. Go head baby beg for it. Beg me to let you come.  sissy phone sex

It’s National Ding a Ling Day. How Do You Measure Up?

It is National Ding a Ling Day. How do you measure up? Ding a Lings come in all colors, shapes and sizes. Now I don’t care what color a ding a ling is, but I do care about its size. Size matters. I only want to play with your ding a ling if it is big! Since today is about celebrating ding a lings, only the biggest and best ones get honored. Those of you with itty bitty ding a lings get humiliated. I am all about naked line ups to separate the men from the sissies.

I will line those ding a lings up from the biggest to the smallest, laughing at the small ones, and praising the big ones. Those big thick manly ding a lings get to fuck me. Put their huge cocks in my perfect pink pussy and ass. Nothing says thank you better to a big ding a ling than a hot, wet, tight cunt. Now if your ding a ling is not worthy, well , nothing says your worthless better than a pair of little girl panties and a good hard laugh. That’s right boys, if you have a string and two silver bells where a cock belongs, then hide that pathetic thing behind a pair of cotton panties. Nobody wants to see it. Oh me bad. No one can see it anyway!

If you want me to play with your ding a ling, then you better be confident that it is worthy of a Goddess. I am not happy to see you unless you  are packing at the very least 8 solid inches of hard, throbbing ding a ling. So don’t give me any bullshit about it being National Ding a Ling Day and I should celebrate all ding a lings. It doesn’t work that way because obviously not all ding a lings are created equal. You can celebrate your tiny ding a ling with YOUR hands, all alone in your bedroom like the tiny dick loser you are. But my hands won’t even give you a wave for less than 8 inches.

So show me your ding a lings. The size of your ding a ling determines how we celebrate the day! You could be celebrating in my sweet perfect pussy, or you could be celebrating in pink panties or even a diaper. Let the celebration process begin. Send me your pics and let me determine if you have a cock, or just a cute little toy.

Hey Lover Boy

Are you in the mood for submissive phone sex training? I’m here let the play begin.   Come into my office and closed the door. First realize you are my slut. I will degrade and humiliate you.  Now I want you to kneel before me. I have a surprise for you. Underneath this skirt is a large strap on. Take it out and wrap your lips round it. Yes, that’s right my little cunt slave.  You are such a timid bitch, suck that dildo harder! I need you to get it all lubed up.  Lick it up and down, swirl that head, suck it long and hard..

Submissive Phone Sex

 I grab your head and force you to deep throat my strap on.  Come on baby make your princess happy!  I can feel you whimper and tremble. Your body squirms as you feel powerless in my grasp,  but I know on some level it turns you on.  I hold nothing back, I use all my strength to skull fuck you.  I hear you snivel at the thrust of my dildo in your face, I take please in your agony.  It turns me on more to know you are my cock sucking servant and you are finally powerless against me. I can tell by the way you hungrily suck my strap-on.  I make you feel sensual and free to express your want for dick under my command. You better believe this is just the beginning, and I’m going to make you a full fledged cock sucking whore tonight.  

Delicious Golden Showers

Lay back let me bring you into my realm of golden shower phone sex. Being a golden shower phone sex 1princess isn’t always innocent. I have to do nasty things and enjoy them. Today will you experience and savor my desires.   I want you to lay back with your eyes closed.  I position myself over your face your tongue comes out to greet my pussy but I smack your balls and you retreat. I spread my pussy lips wide it starts to flow. This hot piss streams out, and runs down your face.  I order you to open your mouth to taste that warm hot juice. Watch how when it stops it streams all over my pussy lips, into tiny drips now.   Come and lick me clean now I like you to tell me how it smells, describe the odor and the taste. Was it that good? I want you lick me till I’m ready again this time I will piss into a cup and make you drink it like a good bitch. 

golden shower phone sex

Sissy Phone Sex

Go ahead and get ready for our sissy phone sex session.  Dig deep into those secret coves and bring out your sexiest feminine ensemble that you hide from your wife.  I got your attention now don’t I?  You can’t help it that little dick is all you have, the feeling of those soft silky panties and nylons are just what you crave. You work in an office by day wearing all these suits trying to do manly things. Though at night when the wife asleep and you are all alone you  are a sissy fagot.

With every call you live in fear that I will expose your dirty little fantasy. You can’t stop, you need me!  I make your dreams reality. Your cock gets all tingly as we talk about how you love being a sissy fagot and how you’re not good enough to be a man. Put that dicky away and let me finish.  I know what truly turns you on is when I tell you about how I’m going put you in a bathroom stall and set up a glory hole where you can suck thick pulsing strange cocks that are just calling your name. I will spank your ass while you swallow that hot jizz. Lick those lips tasting all you can, it’s not every day you suck so many cocks.  Then I’ll plaster your ass up there where you can just get fucked by every tom, dick and harry.  I bet your panties are just so sopping wet by now, go ahead pull out that puny excuse you have for a dick and start rubbing it.  Do you think I’m going to let you cum? Ha ha ha. You know you can’t confess these secrets to your wife that’s why you always have me to turn to, slutty cock sucking faggot. Don’t worry I your secrets are safe with me…maybe.

Sissy Training Phone Sex with Brooklyn: Fitting Room Rendezvous

I have a new sissy in training. I’ve got her looking like the pretty girl she was born to be. I mean she was born with a clit stick, not a cock. From the moment I met her, I knew she was just born in the wrong body. Just because she could not fuck me, did not mean she did not have a role in my world. So, I have been grooming her to be my newest sissy. Today, she dressed herself for my approval. When she picked me up for our shopping trip, she looked gorgeous. She had been paying attention to me in regards to how a whore applies makeup, dresses, styles her hair and does her nails. The true test would be if she could convince others she was a true pretty girl.

We went into Victoria Secret and immediately all eyes were on us. Well, most eyes were on me. But my sissy caught the eye of a pretty handsome man. Now, I have been teaching her how to suck cock too, but technically she is a virgin still. She has only sucked dildos and the like. I gave her a sissy assignment. I instructed her to go find something sexy to try on, and get that guy into the dressing room with her. I wanted her to give her first official blowjob. She did exactly as she was told. As a sissy trainer, I was so proud. I followed them into the dressing room, got myself in the room next door and stood on the seat to look over. I had to watch her give her first blowjob!

I was shocked that she did not seem nervous at all. She was on her knees with his cock out. It was a much bigger dick than I thought by looking at him. I was a little jealous.  Her pretty polished hands grabbed his cock and guided it into her  mouth. She sucked his rod like she had been swallowing dicks for decades. My sissy was making me wet, not just proud. I guess I made some noise as I was rubbing one out watching her pop her mouth cherry. The dude looked up and caught me spying. He wasn’t  upset, but turned on. Told me to get my hot ass on over. I joined them, put the occupied sign on the door and told sissy to guide that nice cock into my cunt.

I twat blocked her lol. If he had a shrinky dink like she did, he would have been all hers, but I am a greedy whore when it comes to a big dick. But she is an obedient sissy, and acted like the perfect fluffer. She got him good and hard for me right there in that fitting room, and he fucked me hard and fast. Dumped a huge load of cum in my greedy cunt. Since my sissy did so well snagging a well hung stud and giving her first BJ, I let her clean my pussy up. I don’t think that stud knew what hit him lol. He was clueless about Sissy’s true nature.

We all walked out of that dressing room together. Both me and Sissy had smeared lipstick on our faces and our well hung stranger had a shit eating happy grin. Sissy gave her first BJ, I got a hot quickie with a real man, a stranger had his cock rocked, and Victoria Secret got almost a grand of Sissy’s money as she bought us both some sexy treats. Not a bad afternoon.

Sissy training phone sex

Today is your day I’m going to turn you into a cock hungry panty wearing, sissy slut. Go ahead and make some time so we can began your training. You won’t be reading, talking to anyone, and we’re not going to sit here and watch movies. You and I will focus solely on my words, I will have your complete and undivided attention. If you’re looking for something quick this isn’t for you. I have a long list of tasks for you to complete. First you need to gather all the items I have listed; panties, vibrator, dildo, cock ring and last but not least a nice red lipstick.  Now the real fun begins you little sissy bitch. For our first task I want you to pretty up those lips…can’t be a sissy without pretty lips. Go ahead and put on those silky panties, you know how soft they feel on your skin. Now slide them over and take that cock ring slide it over your dick and balls, yes put those balls in it. Are they in there tight good that’s what I like?   Don’t think about touching that cock without permission your balls and cock are mine tonight. How do those sissy balls feel in those girly panties? Are they nice and tucked away. Don’t try to hide  I am watching with my devilish eyes every move you make, waiting for the right point where you fuck up and I can humiliate you to the extreme.  So take that little vibrator and start rubbing it on your balls. Making little circles feel it as it starts to tingle. I don’t want you getting too hard yet. Now slap those pretty things, make them sting. Every time you start getting too aroused I want you to slap those girls.  Now take that dildo and warm it up by rubbing it in your hands, with it nice and warm slide it into your mouth. You like sucking cock don’t you sissy whore? Suck that cock like you mean it. I know you want to touch yourself don’t you? That fucking puny little dick wants to come out and play, well slap them get them under control it’s not time yet. Continue sucking that perfect dildo, that’s what a real cock should be. Now take it deeper you cock sucking whore. Show me you know how to suck dick I want you to suck that dildo like it’s going to cum. I’d love to see the look in your eyes as you suck it good. I bet you’re so desperate to be my little cock sucking whore you would do anything I want?  Slap those sissy balls, kill that desire to touch them, they better be sore. Come on you nasty slut!  I want you to continue sucking that dildo getting it nicely lubed up and fuck that little slut hole some more. Look I bet you can’t keep that hard on in those pretty panties pull it back a little let me see it, awe now slap it hard. Good slut don’t worry we’re almost done. Now take that lubed up dildo and fuck that tight little ass come on fuck it well!  I want to see you cum from fucking that tight hole. Mmm good.  Such a good little whore.  Training is complete for today. You be sure to bring yourself back for more sissy training.

Sissy Phone Sex with Mistress Janelle

I got a new strap on, and I had already had enough pussy for the week, so I decided to order one of my sissy boys over for a good ass pounding. I specifically told this boy whore to wear his blonde hair – and he shows up as a redhead. I swear, they NEVER listen. Luckily, I had just the right thing for this sissy phone sex boytoy. I brought out my newest toy, and made him give it head for over a hour.

I yanked on his tiny balls and laughed at his horribly small dick. He doesn’t listen well, but is one of my favorite little sissy fags. I flicked his tiny cock inside his panties until he was crying to get fucked by his Mistress. I made him keep sucking and drooling until his jaw was sore. That will teach him to show up in red when I specifically ask for blonde.

I told him to put his pansy ass up in the air and his face on the floor. He thanked me, and did as he was told. His tight little white shaved ass glared up at me and my blood began to pump as I anticipated pumping that little tight asshole of his. I love making him scream like the little bitch he is, and I knew this black and metal strapon would do the trick. I strapped it on myself and the power I felt made me cum down my legs before I even got inside him.

He got no lube and no mercy from me. I rammed it so hard in his ass he started screaming like a fucking baby. That just gets me going even more, and I pounded his little sissy ass while he begged and begged for me to slow down. He began to shit himself, like a typical baby, and it ran down his legs as I continued to fuck him. I was determined to make this little sissy pay for all the shit I had to put up with this week, and all the crying in the world wasn’t going to stop me.

I told the baby pansy to go get in the shower and clean himself up. I followed him into the shower and bent him over against the wall while I fucked him again. His little sissy ass was so torn up, and I fucking loved it. I sent him home naked and sore and told him to throw away the red hair – I never wanted to see it again.