Category: Sissy Phone Sex

hardcore ass fucking

hardcore ass fucking

One of my sissy boys come over to play with me. He loves getting fucked in his tight ass hole. I love fucking him in it. He gets here and I command him to take off all his clothes. He obeys me. He gets on all fours. I pull out a nice big ten inch dildo. I take out the lubricant and douce the hard rubber cock in it. I slowly slide it into his begging ass. He moans as I slide it all the way in. He begs for more. I take my eight inch pink dildo and i shove it deep into his little cum guzzling throat. He chokes on it. I keep it deep inside of his mouth as I continue to fukc his whore hole. He loves every minute of it. “Take that cock you cum slut!” I say. His cock is jumping as I fuck both of his holes. I start to thrust the big hard ten inch shaft deep into his now loose ass. His muffled moans turn me on so much. I fuck him hard and he squirts his white cream all over the floor for me. “ clean it up! You know I don’t like messes.” with the cock still in is tight ass he begins to to lick all his cum up. He is such a good little fuck toy.

Sissy in training

Sissy phone sex MayI have interviews all next week for a new assistant and I am not sure that any of the potential applicants are going to measure up to my old assistant. I am going to have to interview them one at a time. I need to make sure they are articulate and that they can sock a mean cock. I simply can not think some times and my assistant needs to know how to clear my mind and my pipes. I need a good pair of dick sucking lips to climb under the conference table, spread my legs apart and start sucking my juicy tip. I need to be able to release all of my pent up energy and frustration from work into the back of a willing throat that will swallow every last drop. I want a good little assistant that will follow my every direction without hesitation and do exactly what I say. It is going to be very hard to find a replacement for my last assistant indeed.

I’m In Your Head

Adult phone chat

Relax and listen to the sound of my silky voice. The smooth, hypnotic tone will persuade you to do all kinds of things you only dreamed of. I am in your head coaxing you to lure that sweet young girl to your car. You will bring her to me and together we will make her scream! Tell me about your bi fantasies. I know you imagine yourself on your knees sucking cock. The feeling of it deep down your throat gets you hard. You will drain the balls for me. My voice may sound soothing in a maternal way. It may take you back to being in diapers.The feeling of soft hands rubbing powder between your legs, fingertips brushing over your tiny pee-pee makes you squirm and coo.I will explore deep inside your mind. Cum with me!

Deep Throat Princess’ Strap On

Sissy Training Phone Sex

As you know, a sissy’s training is never done. One of the first things a sissy needs to learn is how to deep throat my princess strap-on. A princess can never get enough of a sweet sissy mouth on her cock. I want you to strip completely naked. Don’t worry, I have seen plenty of tiny clitties before. Yours is no different. Get on those soft knees of yours and suck it down slowly. Gagging up a little spit is par for the course, just use it as lube honey! I know that makes your clittie throb and your sissy clitty pucker and ooze. Pretty soon you will be begging me to fill you up, but I won’t! You have to sit up and beg like a little poodle. Aww..come on, whimper for me!

Adult Baby Phone Sex – Shannon

Adult baby phone sexOk, so I’ve had some sissies hitting me recently, and I’ve been enjoying myself with them. Most of them love to be humiliated and forced to play around with the big, beautiful dicks that I plan to fuck. They also love when I finger or strap-on fuck their ass holes. Well, just the other day, I had a man come to me asking for some TLC. I didn’t think anything of it until he took his lovely dress off and handed it to me, displaying a very dainty-looking adult diaper cover. I hid my surprise, as this was my first time seeing such a thing, but surprised I was. When he crawled over to me and wailed a quiet “mommy” while holding his arms up to me, I figured it was time to sit down. I sat on the sofa and let him crawl up into my lap. He proceeded to cry, so I checked his diaper to find a very healthy dump. I groaned inwardly while outwardly telling him that mommy thought baby had boo boo-ed very nicely, and mommy would need to change baby. I asked if baby knew where the changing stuff was, and he gestured to the over-sized man-purse he’d brought in with him. I left him lying on the couch with a gentle warning about how he would hurt himself if he fell, and rummaged through his man-purse. I found a pack of wipes and a fresh diaper in the bag, which I brought over and used to change him. He seemed to really enjoy having his tush wiped, so I spent an extra minute or 2 doing that, making sure to clean his tee-tee and the creases and folds of it. He then spent a good deal of time suckling at my breast before he said he had somewhere to be and that he really wanted to do it again soon.Hot ass sex

forcing him to watch

sissy phone sex

I have one of my sissy boys tied to the chair next to my bed. He is butt ass naked. His tiny little cock lays limp. I am on my bed with my see-through nighty on. It is red and super sexy. I have my toys laid out. I get up and move him closer to the bed so he can get a good view. He can’t fuck me his cock is way too small and I’m not about to waste my time on someone like that. ===giggles=== I lay back on the bed and start to rub my clit. I moan loudly for effectiveness. I hear him sigh in pain. I look over. His little shaft stands at attention. So sad! I take my pink rabbit vibrator and I begin to fuck my cunt with it. It feels so good. I shove it in and out of my tight wet pussy until I orgasm. I feel my pussy clench around the vibrator. I look right at my sissy boy. “you wanna fuck me so bad don’t you.” He nods his head. I fuck my soaking wet cunt again with my toy. Ramming it in and out faster and faster. I moan loudly and orgasm again. I love torturing these little prick sissies.

What a little bitch

sissy phone sexOMG what a little bitch you are! Look at you pathetically sobbing because I won’t let you ruin my dress, you have your own slutty clothes go wear those! Since you want to act like a little bitch sissy, I think I will treat you like one today, go get dressed we’re going out. I’m going to take you over to my friend’s house where there are lots of horny men waiting to pay me to abuse you. I’m going to make sure that they all take a turn on you! Your little man pussy is going to be stretch wide open and dripping with cum… you will have a belly full of it too. They are all going to take a turn on you, they’re all going to make you the whore you’ve always been meant to be!

fucking and sucking his tight ass

anal phone sex

I invited a fuck buddy over. We ate dinner I fixed him baked chicken and potatoes. He had seconds. My mamma always said the best way to a man’s heart is through his stomach.my mother forgot to mention that the other way to his heart is to fuck him right. ===giggles=== we go to the bedroom and strip down naked. He bends over and exposes his glory hole. I know exactly what he wants. I tingle with excitement. I get the lube out of my nightstand. My Dildo out from under my mattress. I open the lube. I generously apply it to the toy shaft.  I apply the lube to two fingers. I approach his fart box and suck on it nicely. He moans with pleasure. I then insert my two fingers into his tight fudge packer. I love fingering a man’s ass. I pull my fingers in and out over and over. It is so fucking sexy it makes my pussy so wet. I add a third finger and lick his balls while I fuck him with my fingers. I want to fist fuck his ass but I don’t think he’s quite ready for that yet. I take out my fingers and I insert my big hard dildo in his now loosened glory hole. I shove it in and out. He yells out with pleasure. I reach under and jack him off at the same time. I use the extra lube. His dick is rock hard. I jack him off just as fast as I fuck his ass. His seed explodes everywhere. His ass clenches at the same time. He screams in ecstasy. I take out the dildo and he lays on the bed belly full and satisfied. He falls asleep which,  lets me know that I found both ways to his heart.

He wishes I’d give him this pussy

Sissy Phone SexOne of my pathetic sissy boys called tonight. He wanted to do an over the phone sex fantasy. I was totally down of course. I can get off to making fun of him on the phone just as well as in person. I lay down in my bed and get relaxed. I make sure and clarify that he is not fucking me on the phone either. He sighs but I know he loves everything I do to him. Otherwise, he wouldn’t keep coming back! He loves to be called a dirty little bitch. He is a nasty slut kitten who loves to take big cock in his mouth and ass. I give him a story. We are at his house. He wanted to have a house party. ( I know how cute and desperate) He leaves it up to me to put it all together. I invited over two of my girlfriends. I will call them slut and whore. Really the names fit them perfect! They are some sluts for sure. ==giggles== I command my phone bitch to strip down naked. He tries to ask where everyone is at but I cut him off. I tell him not to speak if he is going to argue or that will be two lashings added for the next time he is in my presence.  He obeys. It is silent on his end. He likes the whippings of course. He definitely doesn’t want to acquire more than his weekly total. I tell him we brought some toys. The slut pulls out a big black novelty dildo. The kind you are supposed to give as a gag gift. This dirty fucking skank loves those big cocks up his ass. the slut lubes the huge cock up nicely. we don’t want to hurt our little bitch boy toy too much. Just enough to make him cry and cum.  she slips it into his loose slut hole. He instantly begins to moan. Take that cock you little slut kitten. He moans louder. The whore then takes her pussy and spreads her legs right in front of his face. I command him to eat that pussy like it’s Chinese food. ( His favorite I might add.) He buries his face deep into her cunt. She squirts almost instantly. There you go, my little slave, eat that nasty cunt. She cums again and again. He makes her pussy get everything soaking wet. All the while he has that big elephant cock inside his ass. He asks me if he can cum. He is so eager to please. He listens to all my rules and follows them. I reward him with permission to cum. I hear him moan and sigh on the phone. I’m glad he called me. I needed someone to boss around. These pathetic cock suckers brighten my day.

Happy Thanksgiving pay piggies!

financial domination phone sexHappy Thanksgiving to all you sissy fairy faggot pay piggies! Today is the day where you give thanks for all that you are happy for and I know that I am up at the top of your list. Why wouldn’t I be? Who else gives you the humiliation that you crave so much? Who else allows you to dress up the way you want to dress up? Not your wives that’s for sure! I allow you to explore your feminine side, I allow you to be the little dick sucking faggot that you were always meant to be so now is the time for you to show all of your gratitude! It is time for you to get your big girl panties on and get to shopping for your Goddess! I want tributes, I want gifts, I want to see just how thankful you really are! Are you ready to show me how grateful you are to have me? I sure hope so because if you aren’t then your next punishment will be very harsh!