Have you secretly desired to have, strap on phone sex, but you think no one knows? Every time you see a woman getting fucked in the ass your cock gets hard and you wish it was you getting fucked. Baby, I have a surprise for you tomorrow; I’m shopping all day. I want you to put what’s in the box on the table. I saw him open the box. It was a pair of black lace French cut panties, he was shocked. He didn’t want to admit it, but they made his cock hard immediately. He saw the note: You know you want to wear them; stop denying yourself.

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My boyfriend saw me naked with nothing on except my strap-on. Come on, little sissy, drop to your knees and suck on my big black strap-on. Take that big cock down your throat and gag as I fuck your face. Listen to him struggle and gag as I shove that cock deep down his throat. Should I let him come up for air, I guess, and then see saliva dripping from my strap-on phone sex?

I pushed him down on the bed and slid my tongue into his asshole. His asshole was getting ready for me to fuck him. Listen to him moan as I shove my tongue and finger in his shit hole. Seeing how fucking hard his cock was and seeing the pre-cum drip from the head. I pushed him down and slid that huge black throbbing strap-on deep into his shit hole. I raped him over and over. Listening to him scream for me to stop as I continue to rape phone sex him until he shot his massive load of cum everywhere. I knew he was just my strap-on phone sex sissy boy now, and I would be fucking him all the time because. I knew he now craved that cock in his ass all the time.

If the thought of this has got your cock rock hard, and you want to feel my strap-on balls deep in your ass, call me now!
I look forward to raping you soon.

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Panty Boy Phone Sex Fantasy

September 15, 2023September 20, 2023 cheyenne

Are you my panty boy? I know you love panty-boy phone sex. Do you love to wear satin panties? I know you love feeling them caress your cock? Baby, you love rubbing them against your little dick, don’t you? You are just a little cross-dresser who loves to dress up and be sexy and wear your satin panties. I am going to make you go out and pick out your panties, and hold them up in the store and show them off. You need to try them on and make the sales girls watch you. You will be humiliated, but that’s part of the thrill for me, and you. Let’s get you all sexy and dressed up.

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Let’s have a panty party and let all my friends watch you strut around in your sexy little panties. Get in the middle of the room and stroke your little dick in your panties and cum for us all. Come on show us all what a naughty cross-dressing panty boy you are. I know you have been stealing women’s panties and licking and smelling the crotch. You rub the satin against your cock and feel your little cock get hard.

Come on I want you to take your hard little dick out and show us the pre-cum dripping from your little dick. I’m going to have a big surprise for you. Maybe I should bring out my friends and make you suck their big cocks and show them what a good little cocksucker you are. I want to watch as they slide their cocks in your tight little asshole. Let them fuck your tight little shit hole and fill it full of cum. We all want to see that cum dripping out of your ass hole and down your legs. We will catch it in a bowl and make you lick it up like a good little whore.

Do you love being my panty boy? Want us to explore, your naughty dirty panty-boy phone sex fantasies together? Give me a call and let’s cum together.

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Consensual blackmail phone sex

September 4, 2023 Ella

Hmm, how would you like to have some consensual blackmail phone sex? I mean, get dirty with me using everything against you. The idea of taking pictures and then threatening to call your wife with you all dressed up in her clothes. I bet that gets your little clitty completely hard. During our casual conversation, you tell me all that strictly personal information, not knowing soon that it would all be used against you. Then I wouldn’t stop there. We will explore all your taboo thoughts, the ones that make your cock so hard and on the edge of exploding. I’m so easy to talk to. All that info comes right out. When your cock starts to throb, and you are so horny, I’ll strike. I’ll have all the info I need to ruin your pathetic life.

First, I’ll start with your wife’s girlfriends I found on FB. Tell me how they would feel after I sent them pictures of you dressed up? I mean pictures of outfits that are known to be your wife’s. I’ll get you to tell me your wife or girlfriend’s phone number or email address. Then, all the important people at your work, I know really how to work this consensual blackmail phone sex. I’ll bring to life all those taboo experiences that you swore you wouldn’t tell anyone. Remember, I’m a professional; I know what to do and say to get that blackmail info out of you. It is one main piece of information that I need. Once I have it. I’ll dominate you. I will then have the power to force you to do anything I want.

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You will be dazzled by how I leverage it all and explore all your wants or desires. My consensual blackmail phone sex is something to be feared. I will be compelled to push your fantasies that you already relish. With each minute, I continue to destroy your life; when you think it can’t get any worse, I will financially dominate you. Draining all your bank accounts and credit card accounts. I will not stop until you are broke. I will constantly remind you of what could happen if you misbehave. $100, $200, or maybe I’ll make it $500!! You and I both know I could do this if I wanted. How much is your pathetic life worth?

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Cross Dressing Sissy Phone Sex

September 3, 2023September 4, 2023 Simone

Would you love to be my naughty, dirty cross-dressing sissy phone sex? I would love you to go and pick out your sexy outfit for me. I would love to have you go to a lingerie store. Pick out your sexy lingerie model for the sales girl. Record it for all to see and hear the excitement in your face and voice.

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Just the thought of it makes your cock hard. I want you to videotape it so I can see what the sales girls and customers say about my cross-dressing sissy getting all dolled up. After you get your sexy lingerie on. I was hoping you could go to the store and have them do a makeover on you. Have them put makeup on you. I want you to be my naughty, sexy girl.

Again, record it for me. So I can see you and the sales girls’ faces and hear and see your excitement. I thought of you dressing up sexy and pleasing me, and the men make my pussy dripping wet, and I know it makes your Lil Dicky hard too. I want to get you dolled up and take you to the club. So, I can watch as the men see you looking so sexy, strutting around. I want to watch them caress you and tell you what a naughty, pretty girl you are. Oh, I want to watch as you drop to your knees and suck their cocks in the hallway. Show those men how much you love pleasing and caressing them.

I know you want to feel their warm hot cum shooting in your sweet ass. Letting their cum drip down your leg as you leave the club. If the thought of this has your little, clitty, dripping wet, call me, and let’s explore our naughty, sissy cross-dressing phone sex, taboo fantasies together. I promise to make it worthwhile, and you will want to cum back for more.

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Feminization phone sex the stages of femdom

July 5, 2023 Sam Jones

Beginners Guide to Feminization Phone Sex. How many times have you searched the hamper for panties? Did you discover that wearing panties felt right for you? I often get asked a lot, how do I become a Sissy? Let’s take a look at something that we can do to help on your journey. First, we begin with your feminization journey there are a few questions you should ask yourself, why do you want to be a Sissy? There are many kinds of Sissies.

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Sexual preference: Do you want to suck cock and fucked in your pussy?
Feminization: Where you only dress up and still be attracted to women.
Sissy Slave: Where you serve a Mistress, she decides what’s right for you.
Humiliation: You aren’t a Real Man but a Sissy who takes criticism.
Blackmail: Where you shower your Mistress with gifts for her, not expose you.

Feminization phone sex takes on many different roles. One they all take on together is dressing up. The best way to determine the things you enjoy doing as a Sissy is to them all a try even if only in fantasy. Then we can begin the process that fits you the best- picking out a girl’s name, what panties to wear, and what shade of lipstick to wear. Remember being a Sissy is fun no matter what is going on in your life. It can take the daily stress out of your life.

Just knowing that you love cock is such a turn-on. If you enjoy feminization phone sex but aren’t into being a Sissy, maybe you want to be close to a real girl as you can be, with the hope of becoming a cross-dresser. There are many combinations as there are cross-dressers and fetishes. Now, there are Sissy cuckolds, Sissy cock suckers, and Sissies who enjoy body worship. I encourage you to explore different things as you go through this journey. Don’t be shy, I have done this a time or two, and I’m here to help. So, it’s time that you put your fears to rest and give me a call today!!

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A Little Sissy Boi phone sex

June 7, 2023 scarlett

Oh my word, what do we have here?? A Little Sissy Boi phone sex. That’s right, a little slut dressed in an outfit looking totally ridiculous, but it’s nice to see that you know how to make me Laugh. I bet you are getting ready for that office party. I would love to send you there dressed as a Sissy Boi. Cross-dressing would make for some real Laughter at the party. Of course, men will be flirting with you and begging for your for their Cock. They will smell like Booze and Champaign, they won’t remember a thing as you sit in the corner Stroking your Clitty.

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I can see it now, you Flirting and Giggling your such a Faggot!! Taking all that Drunk Dick and knowing that you are so Pathetic!! Think about what will happen in the coat closet as one comes and slams his Cock right into your Little Ass. You know they think of you as Pathetic and so on. So, it’s no Surprise as you come Dressed as a Sissy Boi phone sex Slut. Feel a hand brush up against your cross-dressing Ass and a finger slide right in. You’re now the Office Whore, and what can you do??

Your Clitty is so small, and you know it deserves to be exposed. Call me now and let me Dress you right for that Next Party. Don’t be left out because you are different, and believe me, they Love your Spunk!! Dressing up is only the Start. Let’s get the basics down First, the Lipstick then the stockings, and of course, the Hair you can’t go out without a ribbon in your hair. So, the time is Waiting. Don’t wait too Long. It’s time that you got what you wanted. Call now, and reveal your Destiny!!

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Sissy training phone sex with Mistress Jaylin

March 24, 2023 Jaylin

Do you have a sexy girl hidden deep inside of you aching to be set free? Have you ever imagined what it would be like to be turned into a girl? Then here is where you need to be with my sissy training phone sex. After I transform you into a sissy, I will have you used like one. Those holes will be abused and treated like a slut. I’ll have you strip off all those manly clothes and slowly change into girly clothes-satin panties with matching bras and stockings.

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Next, I will have a look at your body! It’s my job to determine what I need to do to make you an acceptable sissy. Know there is more to being a sissy than wearing sissy clothes. It’s taking that extra step in shaving off that scratchy body hair, making you nice and smooth, I will show you how to tuck that cock.

Perhaps I’ll even have you put on some red lipstick just to finish your look. I will give you a new sissy name. I have experience with the aspect of sissy training phone sex, from teaching you how to walk in high heels to how to suck a cock properly. When you call I’ll help to remind you of your sissy status. I’ll ask about your behavior, and if I find out you have been touching that sissy cock of yours. There will be a punishment you will have to pay.

Next, I’ll show you the best cocks there are around. How to properly satisfy those luscious black cocks. I understand that every sissy is an individual, and I will customize your training to your needs. Sissy fantasy includes:

Forced Femininization
Sissiy Humiliation
Strap-on Training
Crossdressing
Sissy Assignments
Sissy Spankings
Gloryholes

Now, the ball is in your court and it is time for you to call me. Don’t forget to mention you’re a Sissy. Otherwise, I will have to punish you, and I’ll take control of you and provide precisely the kind of sissy training phone sex you need.

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Crossdressing phone sex with Lady A

March 10, 2023August 1, 2024 anastasia

Cross-dressing phone sex is just one step away from a full-blown sissy, right? How dare you try to fool me by dressing like a man and coming at me with that tiny dick between your legs. I need a big cock to get satisfied. Not some worthless sissy and that pathetic dick of yours will do. Did you really think you could fool me? How many sessions have we had please, I knew your voice from the get-go. You really should be ashamed of yourself, you know. I think by the looks of it that you need a hard dose of a reality check. That I get to tell you what I think of your pathetic little ass. Your pathetic ass doesn’t mean a thing to me.

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It just means that you were born to have your as out there for rent, little bitch boy! Before, you have your first cock you will see that size does matter.

Now, people are going to lie to you, and yes even your lovely wife. She will dote over that little dick, begging you to fuck her. Only to mislead you as to when she left to go to get fucked by a real man. We all know that she is getting a real dick on the side. I’ve seen her down at the local bar, all dressed up in the clothes she found. While I laugh at your misfortune and now you are so pathetic, that you put on her used clothes. And parade around like some cross-dressing phone sex whore through town.

I love the fact that I get to tell you that having such a small dick makes you less of a man. I don’t need you for the dick size just that wallet. Because that is the only thing you have going for you that will satisfy me right now. You need to hear how worthless you truly are! The best way to show how it pleases me is by renting your ass out. It’s so much fun to degrade and humiliate you entirely!!

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Sex therapy phone sex is this what you need?

December 30, 2022 Sam Jones

One common question I often get asked is, do I need sex therapy phone sex? I will help you analyze what parts of your life are the most affected by how you feel. Then address them in our sessions. There are different stages. Which we will go over during your sessions. During your initial appointment, I will talk with you or with you and your life partner, together unity on a united front. This isn’t only educational but supportive as well.

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I will work out your coping mechanisms to help improve your responses in the future. So, that you can have a healthier sex life, I will work to help you push toward acceptance of your true self. Sex therapy phone sex is comforting and encouraging change in who you truly are. No matter what ales you are or what you desire most. Whether it’s cross-dressing, self-gratification, or gender identity, if there is a lack of intimacy or difficulty communicating with your partner that leads to your most serious personal concern, a sex therapist is a good place to start.

I can assist with the help of telling your family. We will get to the heart of the issue of why you are the way you are or lacking. I know this isn’t going to be easy but admitting and asking for help is the first step. Sex therapy phone sex can be very rewarding.

Some challenges to remember:

I’m not here to take sides or to persuade anyone.
I can not change your gender.
Remember, this is a safe place and your sessions are private.
This isn’t a sex session unless you specifically ask for that kind of session, then I’m limited to orgasmic training and self-indulgence.
I am here to guide you through life changes if you have an orgasm there are plenty of other girls to choose from for that.

You will most likely leave with assignments and work to do before your next session. Due to the content of our sessions, you must be 21 years of age and over. I look forward to scheduling my next session for sex therapy phone sex with you. To be continued…

Don’t forget that you can pay online to book your therapy session. There is a $30 deposit for after hours therapy sessions which is non-refundable

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Panty boy phone sex cum be my bitch

December 26, 2022 kendra

Well, looky there wouldn’t you know it?? There is a panty-boy phone sex slut right there. I have been looking all day for one, and now that I have found you. There is some fun to be had. I just back from the lingerie store and have some sublimed selections to choose from. Now, I just knew that these would make you a sissy. Let’s try them on first the pink pair, then the red, oh what a pretty sissy you are. I get so excited watching you parade around in those panties. Go on, try the next pair on, oh step in and tuck. See, I knew you would look so pretty and hot in those bright red panties.

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I turned you into a cross-dressing sissy whore. You have never been to any lingerie store before, but I changed that for you. Once you walk through those pillars, bam it was instant sissy land. it was like you died and went to heaven as soon as we walked in. Panties as far as the eye could see, those secret panties didn’t leave much of a secret. that itty bitty clitty just got so hard as your hands floated over the panties. And the sweet smell of secrets made you feel just like a woman.

I think it is time to play a big boy game!! Come on over with those panties on, showing me how much of a sissy you truly are. Ass up faces down, ready to take that next BBC phone sex on. Watch how he takes that pussy and makes you a sissy. Just like I taught you, oh, you can’t get enough of that cock. Your lips are ready, and it’s time to open them up. Take that ass to mouth like a good bitch. I knew I picked good panty-boy phone sex when I got you. Others come and go, but you take the cake in taking cock.

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Tag: Crossdressing phone sex