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Feminization phone sex for cock sucking sissy’s

By Sissyplaytime September 15, 2023 Feminization phone sex, Humiliation phone sex, sissy phone sex

No wonder you call me for sissy phone sex,the way you talk about wanting to be a fluffer for me it is clear you are a sissy faggot cock sucking slut! It came as no surprise "sissy playtime" "sissy phone sex" "feminization"though. I knew what you were the moment I talked to you! I live in a small college town and happen to go to a very elite college. You would not believe the amount of sissy boys I run into.

It’s so funny the way these sissy cock sucking faggots try and make me believe they are real men but they hint again and again that they will do anything for me. Of course when they say anything they mean suck cock and get fucked for me.You love cock sucking phone sex! My theory is that deep down all guys want to suck cock and get fucked by it. You are obsessed with it! What do you guys call eachother when you are shit talking?  Cock sucker or faggot, that’s what! You spend so much time avoiding looking at each other’s cock when in reality you just want to get on your knees and suck it.

When I am using  my strap on in your tight ass you are begging me to put you in your place even though you are often puzzled by how I got you to admit you are a dirty cock sucker! You love to be humiliated, called a sissy cock sucker or faggot. Since nothing gets me wetter than to play dirty games I am more than happy call you all kinds of fun games while we fuck. Next time I may let you bring one of your macho frat friends for you to suck!

Dirty Sissy Phone Sex is what I want to do Call: Princess Mia 1-877-368-7505

Ms vickie gets sissy orgasm denial during a humiliation phone session!

By Sissyplaytime August 29, 2023 Humiliation phone sex, lingerie, pink panties, sissy feminization, sissy phone sex

"sissy panty boy phone sex" "femdom" "humiliation phone sex"Ms. Kate has done many sissy phone sex calls with naughty sissy’s wanting panty dress up humiliation.   Ms. Vickie is a naughty sissy gurl, and I have feminized, trained her, given her hormones.  She is very pretty and feminine and  has very pretty boobies, and is a sexy young woman.  Vickie also has some fantasies that she likes to share with me.  She sent me one, via email, and W/we did a two girl sissy phone sex session with Jennifer and myself. Let me post ms. vickie’s very sexy fantasy here it is interesting as it has some orgasm denial, and sissy humiliation as well:

My sister, Becky, caught me trying on her 4″ heels, again. She wanted to punish, embarrass and humiliate me. She had me take off the heels and put on a pair of 5″ heels with a 1″ platform. She explained they were effectively a 4″ heel but a lot harder to walk in. She then had me change my top to a pink tee with SISSY in red stenciled on it over my boobies. It is a size too small and really them. Becky said she wanted to do a cliti inspection and told me to unzip and lower my black skinny jeans. I then had to expose my cliti and balls by pulling down the front of my pantyhose and pink panties and putting them under my balls. I then had to raise my jeans, button and belt it.

I was not allowed to raise the zipper. Becky reached in and pulled out my cliti and then reached in and grabbed my balls and pulled them out also. She squeezed my balls telling me not to wear her shoes without permission. I was in tears and said I was sorry. She laughed at me and said she was leaving. I could not change clothes, raise my zipper and, since she was leaving, did not have permission to ejaculate. She said I could wait until Mommy came home and explain why I looked this way with my cliti exposed or call our Auntie and have her come over to the house and let me ejaculate and change clothes. I call and explain what has happened.

Our scene opens when you come to the house. You are accompanied by another woman. I am embarrassed and humiliated to see another woman with you. You explain when I called, you were talking with your friend about sissies and how you thought they were wonderful. You thought it would be good for her to meet me. You tell your friend all the things I am good for. As you go on, my cliti starts to jump. If I am good for your friend, you give me permission to ejaculate.

Ms. Kate for sissy feminization phone sex calls at:  1-877-368-7505

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email me your fantasy at:  Kate@verbalhandjob.com

Cross dressing phone sex with some feminization for complete transformation

By Sissyplaytime January 26, 2022 Cross dressing phone sex, Feminization phone sex
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Ronnie

If you call me for a cross dressing phone sex session,  in a high-pitched girly voice and admit to me that you have a fetish for crossdressing I will be sure to have fun during our phone sex session.  I want you to  be prepared to be treated exactly as you truly are, which is an inexperienced girl.  I will have you get dressed up in all types of pretty little outfits.  I will take you shopping, buy you panties, and bras, and girlie things.  Oh, you caught me stepping out of the shower, little one?  You are admiring my boobs and wishing they were yours.  If you want rub your little clitty, maybe even stick some fingers up inside of your pussy I will teach you to do so like a real girl.

Most girls learn it growing up, but I will teach you during sissy training sessions, and I know you will enjoy that.  You will be transformed into the girl you long to be.  Dresses, and makeup, and maybe going to clubs with other girls like yourself.  Cross dressing is a lifestyle that I enjoy talking about.  You will learn all the sissy things you need to know to please me.

Mistress Ronnie for feminization phone sex at 1-877-368-7505

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All about Debbie Lynn – Call MS. Jennifer talk about transformation

By Sissyplaytime March 1, 2021 cross dress, Cross dressing phone sex, transformaton

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I have been talking to my friend Debbie Lynn about her transformation if you have been following the blog I have several interesting posts about her. She has a very exciting life and I enjoy hearing about all her experiences.  She has been exploring being feminine and has a big wardrobe already.  She had a nice summer wardrobe, lots of lingerie, she loves sexy silky lingerie. I reminded her that she needs a fall wardrobe.

At first she was only testing the waters.  But now she tells me that she really wants to do the entire transformation and she is looking forward to it.  She has been taking birth control pills/hormones, and loves everything female.  She says they have affected her and she can feel the difference already. She had many hurdles to overcome. Meeting both her boyfriend’s family and then eventually telling her family about her new interest in being a woman.  Her mother loves that she wants to be a girl, and has been super supportive of everything. Her mom buys her lots of things. Makeup, she has given her clothes, lately she has sent her things from JC Penny’s. Recently her boyfriend bought her some petticoats.  He is very hot for her. They have an enviable sex life.  She is a lucky girl. She has her boyfriend’s sister as a confidant and his sister has been helping her become womanly, with makeup instructions, and helping her shop, and tips and such.

Debbie Lynn has gone to a wedding in full female attire, this was during the summer, I felt bad for her, she was dressed in very hot material and suffered, she has had to learn about the difficulty in high heels, and being prepared for all sorts of things, that men do not know that women do. It is fun to hear her tell me about things, that I take for granted. However she learns quickly and loves it and embraces it.

This is something Debbie Lynn wrote about her hormones ” I have noticed the birth control pills are starting to effect me more.  My nipples are getting very sensitive.  My clit seems to be shrinking and getting very tougher to get an erection.  I am not complaining, it is happening and for the better.” and her is what she said about some clothes her Mom was getting her.”I did get the clothes from JC Penney on Thursday.  It was waiting for me.  My mom did say she found some clothes for me at the thrift stores.”

Debbie Lynn is also looking forward to Halloween, Here is what she told me, “I have 2 choices for a Halloween costume.  The first is a ballerina costume in pink with tights, leotard, tutu and slippers.  The second (and I know  I would not choose it) was a dominatrix costume in black.  So I am going as a pretty ballerina. Also thinking about ordering some specialty high heel shoe which I would be standing ton my toes.”

I keep telling her, she has nicer things then I do!  About her petticoats, (I am trying to update you all on all the interesting things Debbie Lynn has told me. Her boyfriend bought her two petticoats one pink and one white.  She wore the pink and her bf went crazy for her in it, and he had to do me in it.  One thing she told me that he does which is nice, is that he he lubes himself up and her too. She wonders why he likes putting a tampon in her after, and he she did find out why he likes doing the tampon insertion.  He told her the other night.  He enjoys the thought of keeping the cum inside Debbie Lynn as long as possible.  Debbie Lynn told me that she enjoys playing dress up when no one is around. She likes to try on the dresses, and skirts because she finds, that she enjoys the feeling of the pulling up and down of the zipper on the dresses as she tries them on. She says, “since men have nothing comparable, it is truly a nice sensation.”

She has really turned into a girl!
I am excited to hear about her next adventure.  She has gone away with her boyfriend for weekends, she has spent time with both her and his family as a girl, I am telling you, you all should take lessons from Debbie Lynn!

Ms. Jennifer for feminization phone sex 1-877-368-7505

Sissy panty boy likes to role play during a femdom phone sex call

By Sissyplaytime February 18, 2021 Feminization phone sex, panty boy phone sex, sissy feminization, Sissy panty boy phone sex
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Ronnie

I took care of a new naughty stroker during a sissy panty boy phone sex call.  Sometimes sissies like  feminization role play phone sex, this time it was a sissy sneaking into my lingerie drawer.   In this role play fantasy I walked in on him and caught him wearing my panties. Not only was he wearing my panties, but he also had porn on, gay faggot porn, at that. I told him that I knew someone had been going through my panty drawer, and I had the feeling it was him.  I laughed and looked at how ridiculous he looked and commented that those panties were a bit large on him, and that I should  have to buy him some panties of his own.  At all this, he began masturbating, stroking his tiny cock, or  clitty, and he was also grinding on the bed. I asked him what was going on with his ass, and he told me he had found a buttplug and had inserted it in him. I rolled him over so I could see it. He was using one of  my buttplugs from my toy drawer.  This really annoyed me, and I decided that he had to be punished.  At which, I grabbed an even larger buttplug, spreading his ass cheeks,  I inserted the much larger butt plug into his pussy.  He struggled and begged me not to do this, he said that he  didn’t think he could handle it, but I continued, ignoring his pleas. Eventually I allowed him to stroke his clitty for me.  However, I am not going to tell you what happened next, for that you need to set up a call with me. Ms. Ronnie for sissy panty boy phone sex at:  1-866-438-2345

Sissy panty boy phone sex for Sissy Maid Trina

By Sissyplaytime January 26, 2021 chastity device, domination, orgams denial, sissy maid, sissy maid training, Sissy panty boy phone sex
Cross dressing phone sex

Cross dressing phone sex

Trina is looking for a some sissy panty boy phone sex and a key holder, and wanting to be a sissy maid. Has a bra and panty set, purple set, and her chastity device. Wants me to hold the key. Came a few weeks ago. Went online and watched a porn movie, about becoming a sissy maid, and that made Trina come. Had taken her device off, and could not resist cuming. Now has it on again, and has not cum in a few weeks.

I would make Trina wear heels, and she has on her bra and panty set. Want to put an add on Craig’s List, to be a sissy list. Maybe some cock sucking. … Dress in a pink skirt, apron, crotch-less sissy panties. Pink, with ruffles, and crotch-less. For easy access, wear chastity device, and I would hold the key.

Dress Trina up in sissy maid outfit, and clean her room. Or if here, I would dress up Trina, do all my errands, give you hormones, and I would make all her decisions, I would take pay paycheck, she would get a second job, and give me that money. Keep her dressed and you would clean my house, I would own and control her..

Trina would love that, be my sissy maid, no more decisions for you, I would make them all. She would shop, and cook, do my laundry, my undies in Woolite, and hang up to dry, my delicates.

Makeup – need to learn about makeup, lipstick, foundation, blush… panties every day, for serious training. She already pees sitting down… has a butt plug, and a dildo. cock sucking lessons..

Wants to serve me and my boyfriend. As a sissy maid, clitty in a chasitity device, and Trina, and could get my boyfriend’s cock hard. I would LOVE that! Is she a good cock sucker? Thinks she would a good cock sucker, and would get it hard, and watch a real man fuck me!

That would be so hot! Trina going to lick his ass… while he fucks me with his 10″ cock.
He is a gorgeous black man! Superior black cock fucks hard and well! Wants to suck the juice off my boyfriend’s dick. And clean me out after he cums in me.

1-877-368-7505

Debbie is my cross dressing girl friend

By Sissyplaytime September 4, 2020 Cross dressing phone sex, sissy feminization
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Jennifer

So Ms. Debbie is really coming along with her dressing up and having a social life.  She has acquired a new wardrobe, head to toe. I am jealous of all her pretty things, she has everything imaginable.   Lingerie, stockings, heels, shorts, slacks, ball gowns, cocktail dresses.  She has a friend who is her bf’s sister, who goes shopping with her on Saturdays.  Sometimes she double dates with her and her husband and her bf.  They have a hot tub.

Debbie’s bf is very amorous, maybe giving her a little too much lovin. Wow, how some of us would not think so.  She has a pussy panty, and also is taking hormones, and getting boobies.  She has learned so much about being a girl, keeps telling me it has happened quickly.  A real transformation, she sent me a picture and she is very feminine and beautiful.  Her bf is quite taken with her.  He has given her flowers, they go away on weekends.

They all went to a wedding last week, and she said it was so hot, she had a hard time managing a heavy dress, and drinking a lot of water. Also sometimes she needs flats, the heels get to be too much, that will all come in time.  I think she is so lucky to have her bf and his sister and husband.

Everyone in their families is accepting of Debbie and her bf. So that is all out of the way, and she is free to enjoy her new lifestyle. I love talking to her about girlie things, makeup and her latest adventures.

More to come…Ms. Jennifer for your cross dressing phone sex.  1-877-368-7505

Sissy faggot panty boys love to cross dress up during feminization phone sex

By Sissyplaytime July 10, 2020 Cross dressing phone sex, Feminization phone sex, Humiliation phone sex, sissy feminization, Sissy panty boy phone sex
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Ronnie

While it is true that I have many sissy faggot panty boys and husbands calling me cross dressing during a feminization phone sex call and they certainly enjoy playing with me.  I am very glamours of course, and many sissy’s would like to be me, or look like me.   I am always on the lookout for my next favorite sissy fairy boy.   What I enjoy the most is that I love to dress you up,  just for me, to show your classy, glamorous side.  I like to see you as my creation,  or maybe I might bring out your  slutty, dirty tramp side.  W/we can go shopping online, and you can even email me pictures of you in your outfits.  If you have a little dick and would like some small penis humiliation, I can watch you on webcam.   I can laugh at your little weenie as you are  stroking your little clitty, and if you have toys,  fucking yourself up the ass.  Not all sissy’s are into ass play, you need to let me know in advance.

Of course  many sissy’s have tiny cocks, in order to be a true sissy it is almost a requirement.  Although some sissies have big cocks and fantasize that they are small, how pathetic that is.  Obviously, real men don’t become sissies,  and you know that.   Because, number one you are a wimp, and real men don’t like to dress up, watch their woman with another better qualified to satisfy her,  guzzle up cum, or go through their wife’s drawers, trying on her silky panties.   No, sissies tend to be sissy faggot panty boys with a need for humiliation, and being compared to a real man.

for small penis humiliation phone sex : 1-877-368-7505
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email me your fantasy at:  MistressVeronica@pinkpanties.org

Sissy cross dressing phone sex | Debbie | with Ms. Jennifer 1-877-368-7505

By Sissyplaytime November 12, 2019 Cross dressing phone sex, sissy phone sex
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I enjoy sissy cross dressing phone sex, especially with Debbie.  I have been helping transform her into the perfect girl. I have been posting about her recent changes. However, I have a lot to tell you about how she started to transform to become the beautiful girl she is now.  She has started taking birth control pills, but before this advance, there were many steps leading up to this. I will go back a bit, and tell all you lucky readers, some of the issues she has faced and maybe some solutions. Be sure to check back, she has so many updates and questions about being a girl, I would not know where to begin to share all this.  I never realized how much you need to know, if you want to be a girl!

A while back she said:
Ms. Jennifer, Thank you for the advice on dressing up for the first time.  Before my bf arrived, I called him and informed him to get some lubricant and I also mentioned some lipstick.  He did.  Afterwards, I told him, if he wanted me to do so again, I would need more lingerie and clothes.  He agreed and said he would get some more.   I will call to inform you how it all went. ( I had suggested these items, and then she asked her bf)
**
Debbie then had a date  and here is an update:
Dear Jennifer: The date went awesome and awkward at the same time.  My bf’s sister brought over a new type of lipstick for me to use…it was the one where I basically paint my lips.  She brought over a couple different colors but she knew the dress I picked out and the shade I wore last night was a pink color.  The dress was a pink floral cocktail dress.  She informed me it was a cocktail dress.  It was all pink but with a floral lace like design from the waist up.  I had to wear pantyhose with the  dress…no garters.  The dress came to above the knee.  I felt very feminine in it.  (Double date with bf and his sister and husband) It was awkward with her husband at the start but as the night ended it was okay.  If my voice was more feminine sounding it would be easier.  We spent the night talking, listening to music, tv and playing some board games.  Some quick thinking on sister’s part saved me from meeting the parents, they were going to stop over and Kendra had to inform them to postpone it.  whew…. my bf sure loved it.  When we got back to my place, I had to quickly change from pantyhose to garters and nylons.  We also tried a new position at the start..me on top sliding it inside me.  That position takes a lot of work from me, I still prefer being on my back with pillows propping my male pussy up.  I so enjoy watching it go inside me. I find that 3 times a night is the norm for him.  The 4th time, he experiences extreme sensitivity in his penis and we are done for a few hours. (Debbie ordered a pussy panty) she said: No the vagina/pussy panty hasn’t arrived yet. Love Debbie Good morning Jennifer, I found I have a couple gripes about dressing up which are small gripes but annoying.  One, I hate getting “runs” in nylons or pantyhose  so quick.  Second, I found wearing lingerie in bed “very warm sleeping in”.  Nylons, garter, gown, bra under the  covers gets very warm in addition to having him all over me. (I told her you paint the runs with nail polish to stop them from running)

That’s about it for now, I will update you gurls soon.
Debbie keep up the great transformation.
xoxo’s Ms. Jennifer

Cross dressing sissy phone sex | Debbie | with Jennifer 1-877-368-7505

By Sissyplaytime November 9, 2019 Cross dressing phone sex, Feminization phone sex, sissy, sissy phone sex
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Cross dressing sissy phone sex training, if you are in need of sissy training, I am the girl for you.  I have been turning Debbie into the girl she has longed to be.  She is going out on her first date tonight as a couple, with her bf.  They have sex together.  They suck each other off and kiss.  They go on long walks and Debbie has been dressing up to please him.   Debbie has been calling me regularly to learn how to become feminine and today she confessed that she wished she could dress as a girl all the time.  She has sent me some photos and I must say, she has come up to the plate quickly, I can hardly see any masculine traits.  She has a blonde wig, and was wearing such a beautiful skirt, sparkly pink top and pink boots. Full makeup. I am getting ahead of all that has happened.

I am going to backtrack and show you the progress Debbie has made.  She emails me with questions and I answer them, she either does whatever I suggest or  has her bf’s sister go and buy her things..

Her boyfriend started out by buying Debbie a dress, and she told me that he liked to have a guy wear women’s clothes.  She was to be wearing the dress, when he came over that night.  Next she told me, “He wants to take a walk down the road after it turns real dark. I don’t know about that.  Scary.  I am afraid of being seen.  I did like the idea of maybe around 2 am.  I did find out I like the sound high heels make on the floor or  cement.  I walked into my garage with them on.  Very distinctive sound.”   I think it is great, that her bf wants to have  real relationship with Debbie, don’t you?

A few days later they had another day planned, Debbie said, “I am all dressed up.  I have my floral print dress, slip, bra, panties, garter belt, nylons and 4 inches heels on.  He should be here any minute.  I put the wig on and the makeup.  Oh, yes  I have perfume on for the first time.  I started getting ready at 6 pm.  He asked me to shave my body (chest) hair and I shaved the legs again.  I feel so feminine.  I think I will walk down the street with him a lot later.  I can’t wait until he gets here.  I am going to greet him at the door and then give him a bj immediately. I can’t believe I enjoy this.  A week ago it sort of repulsed me, getting dressed up and going to be fucked like a woman.”

After her date Debbie wrote me: ”
Dear Jennifer, It was wonderful.  So much happened last night.  I greeted him and gave him a bj and deep throated him (with his help) and he came in my throat.  (We agreed he would hold my head and he did and I took it all). Afterwards, after he undressed me, I even fucked him in the face and put my cock all the way in and came down his throat.  Then, we went to bed and he came inside me while I was on my back and then he did me doggy style ( I prefer on my back).  He helped me put the dress and slip back on and we went for a short walk and I sucked him a little by some trees but not all the way to climax (too much nearby traffic).  He also brought over 2 purses for me.  A small one to keep the basics like lipstick, mascara, liner etc..  The 2nd one he called a sleepover bag for me to put lingerie and everything to spend the night at his place.  I am glad he did not spend a lot, he picked the items up at a Goodwill store and a Salvation Army store.  He wants to pick me up at my house and go to his house tonight while I am dressed up and I told him it would have to be dark outside.  I mentioned we need to get some fake breasts instead of socks. I tried plucking my eyebrows a little, but OUCH.  That hurts.

He wants me to meet his sister to have her show me and help me with a few things.  I may.We laughed, he fed me and seeded me.  So to speak. All this made me wish I was a woman with a vagina. Debbie

This is a little background. As I said tonight Debbie is double dating with her bf and his sister and her husband. I will update you on some of her past transformations in my next post, and let you know how she makes out tonight, I can’t wait to hear what she has to say, what she is wearing, and how the night goes.

Ms. Jennifer 1-877-368-7505