Sissy Phone Sex with Annaliese

In my opinion when it comes to sissy phone sex, a submissive male should embrace his curiosity. I spoke with someone who questioned his identity. He was unsure if his desires made him feminine or not. He confessed that when he was in high school it was a derogatory thing if someone said “Oh look at that little sissy over there!” I told him “People can be so judgmental. They cast stones and are quick to put someone down. I don’t think it’s wrong to be a sissy at all. In fact I have a lot of friends who are like that.” He found comfort in my words and just being there to listen to him. So much that he started telling me things that he had done. I’ve never seen myself to be the type of mistress that assumes things. I would rather take the time to get to know how a person feels and be there when others won’t.

Sissy Phone Sex

He told me he grew up being a bit of a momma’s boy. I told him “There is nothing wrong with loving and being close to your mom. Sometimes that’s all a guy has is his mom who nurtures and cares for him when others are casting stones. But I could still tell that he desperatly wanted to know if I thought he was into being a female and sissy phone sex. He said “Sometimes I pass by department store windows and get drawn into what it would be like to wear sexy skirts and attractive tops. I’ve also wondered what it would be like to wear a pair of panties and lingerie.” I told him “It sounds like you’re ready to dip your toes into being feminized. Just think about how good it would feel to have satin material laying against your smooth skin. Talk about becoming hooked!” That really excited him. He went on to say “How do you feel about transsexuals?” I said “Oh my, are you kidding me? You can’t get any better than a tranny. Especially if you’re bisexual. You have the best of both worlds! What more could you ask for than having a sexy female with breasts and a hard cock to go with her!”

I could feel my satin panties start to moisten. My juices became more intense when I thought about us both sharing a tranny together. I’ve had the pleasure of getting on my knees to suck a hot transsexuals cock before and the experience is something I’ll never forget. I’ve also had the pleasure of feeling a trans femm worship and lick my bare pussy as well. He told me “Annaliese, if I tell you a secret, you won’t think badly of me, will you?” I said “I certainly will not! Please share your secret with me!” I was on the edge of my seat anticipating what was about to come out of his mouth next. With sissy phone sex it could be any exciting jaw dropping event that make you finding yourself wanting to know more!

He said “I went to an adult book store and went into one of those rooms where you put money in the slot and watch an explicit flick.” I had a feeling but didn’t want to burst the bubble that he was going to tell me that there was a glory hole with a hard cock that was ready to be sucked. I knew he didn’t want to suck a mans cock but he said “Annaliese I fantasized that on the other side was a hot shemale.” He sucked that cock until it was ready to explode. He finished by wrapping his hand around the shaft and jerked it until it came all over the fucking place. I smiled with excitement and said “Yes! You are defintlly a sissy!” Hearing those words made him cum so fucking hard. He said “Yes! I’m a sissy fag! Please tell me I’m a sissy fag Mistress Annaliese.” I repeated it over and over again.
There are so many other exciting secrets he shared. Can you even begin to imagine what they were? Ask for Annaliese by dialing 1-888-662-6482 I can’t wait to hear all about the sissy phone sex secrets you want to share with me.

Coerced Feminization Phone Sex with Quinn

Now that I am in my forties, I’ve learned exactly what I like and am not shy about it. And I love coerced feminization phone sex. There’s something so fucking hot about slipping a supposed alpha male into something soft and feminine, watching the way his body reacts to the feel of silk against his skin. There’s power in dressing a man in delicate lingerie, especially when it’s my choice. I’ll start slow, teasing him with a playful smile as I show him the pieces I’ve picked out—a lacy bra, satin panties, maybe even stockings if I’m feeling especially daring. I can see the mix of curiosity and hesitation in his eyes, but that just makes it all the more thrilling.

Coerced Feminization Phone Sex

I’ll trace my fingers along his chest as I guide the silky fabric over his body, loving how vulnerable it makes him feel. There’s something so sensual in reversing the roles, seeing a man submit to something he never expected to enjoy. And as the silk hugs him in all the right places, I see him soften, surrendering to the moment, letting me take control. I love how the smooth fabric clings to his skin, making him feel sexy in a way he never has before. It’s not just about the lingerie—it’s the trust, the intimacy, the way I can blur the lines of what’s traditionally masculine and feminine. And the best part? Watching him slowly realize how much he enjoys it. The way he blushes, the way his body responds to my touch. It’s a power trip for me, but also a way to explore something intensely erotic together. The look on his face when he sees himself in the mirror, feeling both exposed and desired—it’s absolutely delicious. And at that moment, he’s entirely mine, wrapped in silk, fully under my coerced feminization phone sex spell.

1 888 662 6482 and ask for Quinn

Sissy Training Phone Sex with Quinn

Sissy training phone sex is one of my favorite things to do. There’s something so satisfying about transforming someone from their everyday alpha male self into the obedient, delicate sissy they were meant to be. I take pleasure in every step of the process, guiding them with a firm hand and a teasing smile. It’s not all fun and games, though—there are rules, and I’m very particular about how they are followed. From the moment they offer themselves to me, I’m in control. I know exactly how to bring out the soft, submissive side they’ve been hiding. I start slow, of course, making sure they understand what to expect –that while I can be sweet, I don’t tolerate disobedience. When I tell them to slip into something pretty and feminine, I expect nothing less than perfection. The tiniest bit of hesitation, and they’ll feel my stern side and my whip. But when they do things right? Oh, I’m not above praising, rewarding them with a gentle touch or a whisper in their ear.

Sissy Training Phone Sex

What’s especially delightful is watching the change happen over time. That initial nervousness fades, replaced by a deep desire to please. My sissy knows their place, following every command with anticipation. They learn to embrace their new role, loving how it feels to be under my guidance, to be molded into something soft and submissive. And as much as I enjoy being strict, I’m never without a bit of playfulness. I tease, test, and push boundaries to see how far they’ll go to earn my approval. Then it is time to take the next step, being the sissy girlie cock slut that they always suspected they might be.  By the end of our sissy training phone sex sessions, they aren’t just transformed on the outside—they’ve fully surrendered. And that’s precisely how I like it. Stern, but with just enough charm to keep them wanting more.

1 888 662 6482 and ask for Quinn

Cuckold Phone Sex with Jennifer

It’s Friday night and you’re home jerking your dick thinking about cuckold phone sex. Although what you are really thinking about is being a cuck yourself. Your wife is out with her friends, or so she says, we both know who she is really with. Don’t we? Your little weenie is all twitchy in her panties that you stole earlier in the evening. Are they wet yet? No worries, soon they’ll be soaking wet and stuffed in your mouth. Just hoping that when your wife gets home, she lets you go down on her and clean her pussy full of her lover’s cream.

What would even be hotter is while she’s gone, you get all dressed in up pretty pink panties, stockings, and heels like a pretty sissy bitch. Perfect outfit to wear while you get the bedroom ready for her and her BBC lover. You’re going to look so pretty on your knees ready to kiss her ass and suck his real man cock. Beg for it as you crawl upstairs behind us wishing you could be us. I bet you’re drooling thinking about sucking his big black beautiful cock. My hand pushing the back of your head making you take that cock down your throat. But it’s not for you slut boy. My pussy reigns supreme around here. And you’re nothing but the clean up boy tonight.

This is just one night in the life of my cuckold lifestyle. The reason I’m fucking other cocks is because you don’t measure up in any way. A dick that small should be pussy free and I’m not afraid to keep you locked up and in denial for a very, very long time. The only fucking we’ll be doing together is my big black strappy up your pussy ass. And maybe another for your mouth.

I don’t have many limits and I have so many interests I couldn’t possibly list them all here, so try me!

For Cuckold Phone Sex, call Jennifer 1-888-662-6482

 

 

Panty Boy Phone Sex with Tamra

Lately, I’ve been getting a lot of panty boy phone sex calls, and I have to say I do love them so much! You know, take a big strong guy and dress him in pretty, satiny, frilly things and help him discover his inner bitch. At first, I was kinda surprised at how many stereo typically “alpha” males had this very desire. But it just goes to show you, everyone has a hidden kink. Well, luckily, they have found me. There is no need to hide anything from me. I won’t judge you, I will take that fantasy and run with it. Wearing lingerie feels so good against the skin, no wonder you want to indulge. And I know it makes you feel pretty/sexy/slutty on the inside too. It really gives me a chance to be so creative, and dressing bitch bois up is so much fun.

Panty Boy Phone Sex

Firstly, I give them their new bitch name. That is my favorite part. Then, we talk about the sexy little outfits I want to put them in. I describe sliding the stockings on his legs, letting him put on my silkiest panties and sexiest bra – and slip into my slinkiest dress. When we have sissy phone sex, I tell him how I will make up his face and hair – and I really focus on his lips. I want them pink and glossy because my new little girl is going to be sucking a lot of big black dick. All sissy boys want a juicy cock to suck, and I love training my sissy sweetheart to take a big dick. He moans in expectation when I tell him how I am going to let that black cock pound his sweet ass, I tell him how he is going to cum in my panties, and I think he starts to drip just thinking about it. If you need panty-boy phone sex – I’m for you!

1 888 662 6482 and ask for Tamra

Cross Dressing Phone Sex with Gretchen

I love turning a weak little man into a beautiful sissy. Cross dressing phone sex is something near and dear to my heart. I love the idea of taking advantage of a weak and pathetic man. Making him submit to me in ways he never thought possible. Making him whimper and beg on the phone to me like a needy little bitch. Just imagine if you were there trying to fuck me, and before you knew it… the tables were turned. I’d love to take some seemingly strong man and just shove the dildo to my fucking machine so far into him he’s begging me to stop. Turning him into a pathetic drooling mess of man meat, right before my eyes.

Cross Dressing Phone Sex

Just the thought of how good it would feel to fully cripple you mentally because your cock just exploded harder than it ever did before. You and I both know you need to give up some control.
Just imagine coming home from a hard day at your manly job and giving control over to me. You see, I’ve always had this massive fantasy of entering a sissy pageant, making you compete. Telling you to show me you deserve the role you want in my life. Making you the neediest little bitch you can be in the prettiest pink ruffly dress you’ve ever seen.

Do you have what it takes to be the best of the best? Let’s find out! call me now so we can roleplay our cross dressing phone sex fantasy and turn you into my little sissy whore. I can’t wait to cum together my little sissy faggot. Just get on the phone and give me a call for cross dressing phone sex at 1 888 662 6482 – ask for Gretchen.

Email me at Taboogretchen@gmail.com
Follow me on Twitter @taboogretchen
Follow me on Bluesky @taboogretchen.bsky.social

Domination Phone Sex with Gretchen

I love domination phone sex. I love using my sissies and showing them their real place. Only real men get to fuck my tight bald pussy. I fuck my sissies, but only with a 12″ strap on. My latest sissy had never had a cock in his ass before, which I found hard to believe because everyone knows sissies are secretly little fags at heart. So I introduced him to my silicone sissy trainer. He tried to resist and was met with a sharp slap to his ass, I told him if he didn’t obey, I would bring in one of my BBC lovers to fuck his ass and make him regret ever crossing me.

Phone Sex

I bent him over and lubed up my strap-on and pulled his tight red panties to the side and started working my way into his boy pussy. Like the little fag he is, his asshole easily took my huge strap-on. I plunged it in and out of him and made him beg for me to plow his ass and make him my bitch. In no time his pathetic little cock was filling his panties with a big load of cum. He was moaning and groaning, saying how much he loved that big cock in his tight little pussy. He was crying saying he wanted fucked EVERYDAY from now on. I called my BBC friend and told him to set up a BBC gangbang with my newest sissy for this weekend! I can not wait to see my little sissy whore get used like the slut she is.

Call me now at 1 888 662 6482 so we can roleplay this domination phone sex together. Ask for Gretchen.

Email me: Taboogretchen@gmail.com
Follow me on Twitter: @taboogretchen
Follow me on Bluesky: @taboogretchen.bsky.social

Sissy Phone Sex with Gretchen

I love sissy phone sex. I can see by looking at your panties that you love it too. Look at the sissy panties you got on, they are so messy already thanks to me!  I can see you already getting wet and excited, just at the thought of being under my control. Oh, and let me tell you, this is just the beginning. Once I get my hands on you, you will be begging for more. Begging me to use and abuse you, to make you my dirty sissy slave. Once you’re under my control, you will just do what I tell you to do and when I tell you to do it. That’s what a good sissy sub would do for her Mistress. And you don’t want to be known as a bad sissy, do you? I didn’t think so. Are you ready to submit to me yet?

Sissy Phone Sex

First things first, I see you’re wearing those pretty little sissy panties. But oh, they are not so pretty anymore, are they? I made sure to have you mess them up real good, just for my pleasure. I love seeing you all humiliated, degraded, and turned into my obedient little slut. And don’t even think about trying to resist me. I know all your deepest desires and fantasies and trust me, I will make them all come true. I will make you my little cock-sucking sissy, choking on every hard and throbbing cock I throw your way. You will learn to love it, to crave it – worshiping every inch of it with your slutty mouth. I’ll be waiting to turn you into the sissy slut that pleases anyone and everyone she encounters. There will be SO much cock.

1 888 662 6482 and ask for Gretchen and ask for sissy phone sex right now, slut!

Cock Sucking Phone Sex with Gretchen

There is nothing I love more than sissy boys and cock sucking phone sex. There is nothing I love more than a sissy boy. Are you a sissy boy?  Why do I love sissy boys? I love them because I know the things, I can do to them and you. And the things I can make them do! I love to see my sissy boys sucking cock and sucking many cocks. Let’s have some cock sucking phone sex.  Do you first need cock sucking training. We can start with you sucking on my big black strap on. You can get on your knees and practice in front of me. I want to see your desire to suck cock. Then of course I will use my big black strap-on on your tight ass. With no mercy.
Cock Sucking Phone Sex
I will invite a friend to join us. My friend with a big black cock. You will take that big black cock into your mouth and start sucking on that big black cock. You will start to open your mouth and deep throat that big black cock. You need to get him to shout a big load of cum into your mouth. And if you do a good job, I may allow you to be fucked by that big black cock. And fucked over and over.
As an extra bonus we may even take a trip to the bookstore to find a few cocks for you to suck on. The more cocks to suck on the better. I want to take loads of cum into your throat or have your face be covered in cum after we leave the bookstore. I may even have you dress up as a sexy girl for that trip. I really love trips to the bookstore where I can pick out all the cocks for you to suck and I can watch. Let’s chat about cock sucking phone sex.
1-888-662-6482 ask for Gretchen
KinkyGretchen13@gmail.com

Cock Sucking Phone Sex with Shayla

The phone rings and I hear your breathy whispering voice tell me how bad you want to be a good cock sucking sissy, starting out our hot cock sucking phone sex session. Such a good sissy you are, dressing in your sexiest nighty with those pink panties coming in and kneeling your sexy body at the edge of the bed. There in the dark in your most quiet, soft voice, “Can I please crawl in bed with you and suck the big black cock you just had cum inside you?

Cock Sucking Phone Sex

I pat the bed between me and my gorgeous black bull of a hubby for to you curl up and start gulping that already hard cock, while I reach down and caress your pantie clad ass, just grazing your silky covered taint with my fingers. I gasp when I hear you gulping the head of the cock down your throat gulping and gagging and swallowing all at the same time. Hearing you gulp and gag is one of my favorite things about our cock sucking phone sex calls. Other than hearing you call me ask to show me what good sissy bitch you are and the need in your voice when you ask to suck the cock I own, it turns me on how long you can go during our sessions.

I wonder how much more of this big black cock you want? If you want more you’ll have to ask for it. I know you want it all the time, more and more. All you need to do is call and ask me. So what are you waiting for? You know you want it now, you want to kneel before me and ask. Feeling me caressing you and telling you what a good cock sucking sissy bitch you are is something you crave every minute of the day. So call me now for sissy cock sucking phone sex.

Dial 1 888 662 6482 and ask to talk to Shayla

Phone Sex : Live Fetish Phone Sex