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I Own Loser Jeffie!

By Sissyplaytime November 5, 2019 blue balls, little dick, no cumming
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Blueballs for you!

The Princess owns your loser ass Jeffie!! You are not to cum, I will make your blue balls bluer! There is no cumming for you. I own your useless balls, no cumming, I have all your power, if you want to cum, then pay the cum tax, otherwise, I OWN YOUR BALLS! **Giggles** Loser!…

“loser jeffie wrote:Oh Princess It is so not fair! I will never win! You have all the Power! All the Sexy Hottness, all The Beauty! And All the Brains!I am just a loser with aching blue balls! You have got me addicted to your sexy Humiliation!When I stroke my MY LITTLE DICK but don’t allow myself to cum since you ordered me not to, I get all twisted up inside! And Hornier for you, and I want to stroke it, but I cannot let myself cum, cause you don’t want me to,and I want to please you, cause you are so super HOT, and I am turned on by your sexy cruelty, and so I want to stroke it,…and I want to please you, so I do not cum,….Do you see what a vicious circle you have me in!”

Cross Dressing sissy Debbie loves phone sex with Ms. Jennifer 1-877-368-7505

By Sissyplaytime November 4, 2019 Cross dressing phone sex, lingerie, sissy, sissy phone sex
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Sissy cross dressing phone sex with Debbie!  Gurls, you have no idea what a great social life my sissy Debbie has. Makes me wish I was her. Can you imagine me saying that.  She spends all her time dressing up, buying clothes, doing girl things.  She is a pampered girl for sure.  Her boyfriend gives her a lot of sex and attention.  She is very sexy, her bf’s sister, takes Debbie shopping for new things all the time.  She has a lot of dresses, panties, she adores garters and stockings and all sorts of pretty lingerie.  She does her makeup, and I give her a lot of make up tips.  I suggested, bra forms, tanning secrets, shaving tips.  We talk about all sorts of girl issues.

She is now taking hormones and I think she may becoming moody.  She says she is tired, and was talking about how her bf wants sex all the time, and she is tired. Sounds like a real girl to me. You know that hormones do change everything. Soon she will have real boobies, I can’t wait to hear about that.

She has been spending time with her boyfriend and his sister and her husband, Debbie wore her swimsuit, and they used a hot tub, and dinner at his sister’s house, sounds like quite the social life.  She likes to suck and fuck cock, and her bf likes to suck her too.  Debbie likes to be fucked more then fucking. She is a real girl.

I can’t wait to hear what she does next.

Ms. Jennifer 1-877-368-7505

Feminization phone sex wear panties for me on webcam you cross dresser!

By Sissyplaytime November 3, 2019 Cross dressing phone sex, Humiliation phone sex, panty boy phone sex, Sissy cuckold phone sex, Sissy panty boy phone sex
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A favorite among cross dressers is to discuss humiliation during sissy phone sex or feminization sessions. That’s right, you may have some cocky attitude, thinking you are some gift to women, but come on, seriously, both you and I know that is far from the truth. You would never have the nerve to hit on me, although you would probably be the type to lie to your friends and boast about wild nights that we’ve had together (that, of course, never have truly occured, nor will they ever!). You need to be put right into your place. I can see in your eyes that you are wanting my punishment desparately, you are absolutely craving my superior dominance.

There are a few types of feminization phone sex it could be a sissy panty boy call, humiliation, dress up, cuckold, total transformation up to feminization.  I love it when a man has a bit of a fabric and clothing fetish, especially.  Likeing the feel of silk, nylon or something slinky against his clit or cock or skin.   Seeing a man on webcam is very arousing to me, especially if you wear a pair of women’s panties, nylon stockings, and heck, even a pair of high heels close by really gets me turned on. Watching You stroke for me – up close, doing it exactly as I say, and how I like it, sliding those silky panties and stockings over your  cock, mmmm, there just can’t be anything better in life!   Especially seeing nylons covering a nice hard cock, it makes me wish so desparately that I could have that covered cock in my hand, giving you a hand job, gazing up at you as  you see your  nylons slide all over your cock due to my control.

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By Sissyplaytime October 29, 2019 Cross dressing phone sex, Humiliation phone sex, sissy feminization, sissy phone sex
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Cross dressing phone sex with my sissy Debbie.  She keeps me updated on her progress in becoming feminine.  She sent me a picture of herself dressed up.  Oh my!  I can’t believe that she is not really a girl in real life.  She is mastering the art of transformation.   She is learning how to use makeup. She says:  “I only put the mascara and lip liner on.  Those I knew how to do from TV.  The eye liner I probably would need a lot more time and the eye shadow…wow.  You women go through a lot to get made up.  There was also something for eyelashes which look very hard to do.. curler?”  Yes, an eyelash curler, she is moving right along, isn’t she girls?    I told Debbie to buy some things and shave her legs, this is what she replied about her bf:  “He called a little while ago.  He is going to get some of the items you suggested and he said had a surprise outfit for me.  Which led  me to ask him about this fetish and me.  He basically said I am the only guy to agree to do this more than once and to have actually shaved my legs for it. We are going to have our next dress up date on Friday.  That will allow for it to go on longer.  We won’t have to go to work.  I will have to practice and put on the eyeliner and eye shadow.  Any suggestions for a type of perfume to get?  I will get that on my own to surprise him.”  Then I received an email He brought over a dress this morning after work, which was his surprise along with a brown wig and shoes with a 4 inch heel. I thought it was going to be a French maid’s uniform.  The other pair was a lot lower.  Oh my god, how do you walk in them in such high heels?”  It’s not easy to walk in high heels, so you better practice!  That goes for all you cross dressing girls out there!

Ms. Jennifer for your sissy dress up and cross dressing phone sex 1-877-368-7505

Sissy phone sex with Ms. Jennifer talking to DEBBIE!

By Sissyplaytime November 18, 2018 Cross dressing phone sex, panty boy phone sex, sissy phone sex
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I love sissy phone sex and as all you panty boys, sissy’s and cross dressers know who follow my blog posts, I wanted to give you some up dates on Debbie, who has been in the transformation process now for a while. I admire her spirit, sense of adventure, and excitement about pursuing feminization and transformation with abandon.  I have witnessed her, start from the beginning. From simply being with a guy who wanted to dress her up. To now, wanting to become a real woman. There have been so many twists and turns. It is amazing.

Recently,  for example she told me the Dr. gave her premarin, that is a female hormone. She has been going thru all the paces, including a therapist, to prepare her to become a real woman. She really wants some boobs, and is planning on getting them. I will update you on some of the latest exploits of my friend Debbie.

Debbie wrote to me: “We had a dress up party last night.  The girls got some special dresses and they selected a gown for me to wear to the glamour shoot this afternoon.  I am all set to go, waiting for Kendra to pick me up.  The ladies picked out a gown which is very feminine, beautiful but has a touch of sissy in it for me.  I thought you would like these couple pictures. FYI, I don’t know where they got the gown and who brought it.  I tried on about 10 gowns.  I am going dresses in it.  Can’t wait to show it to you if pictures came out ok.  A hint I feel like a bride, it is so big and cumbersome.  I can hardly breathe in it too!  Beggars can’t be choosy.”

She recently had glamour shots done, and her friends had her dress up in bridal gowns for the occasion. She even sent me pictures of the glamour shots, they were awesome, Debbie did not really like the puffy shoulders on the dress but she does look beautiful. She was unsure whether or not to show her parents the photos, but now she has decided to do so.  Both her parents and her bf’s knows about her cross dressing.

Her BF wants to marry her, but she is not rushing into anything.  She has some personal things she has done, I have to ask her if she wants me to blog about it.
Until next time.

Ms. Jennifer 1-877-368-7505

Debbie has new breasts – sissy phone sex with Jennifer

By Sissyplaytime July 8, 2017 Cross dressing phone sex, crossdresser, sissy feminization
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My friend Debbie is so gorgeous, she called me for sissy phone sex.  She is not a sissy, she is a girl, that I have watched transform, into a beautiful woman, she has many blog posts on here, so you should check them all out.  She has been on a journey, never knew that she had this in her. Now she has gotten breasts.  I have enjoyed Our/our journey together, I have taught her many things about being a woman, she often remarks that she never thought of it that way.  I have so much fun with her, she has a better sex life then I do. For a while she was going with one guy, that kind of got her interested in dressing up as a girl.  I talk to many who love to dress, I enjoy talking to cross dressers, although Debbie, I consider a girl, not a cross dresser.

She started out on a date with her first boyfriend, he introduced her to panties, I believe that was the start, then he would buy her things and take her to places, it has all been very exciting.  She never knew she was inclined this way. Now she has another bf, the first one never expected her to transform.  Her new bf really likes how she is, and has taken her to meet his family.  Her family is good with it all, and even paid for her new breasts.

Debbie sent me a photo of her nude, and let me tell you, she is gorgeous. Her breasts are perfect, she still has a cock, and is gorgeous.  She is so beautiful. Gorgeous, face, hair, makeup, body, just yummie.

Will keep you posted about what she is up to!
Ms. Jennifer for your feminization, cross dressing, femdom, panty play, and other phone sex desires..

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Halloween for Debbie – Jennifer’s Girl Friend!

By Sissyplaytime April 23, 2017 Feminization phone sex, transformaton

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Have to tell you how I adore Debbie.  She is the ultimate girlfriend, I wish I had her mindset.  She decided to embrace what she loves and is going for it.  She has transformed into the most beautiful woman.  Sent me nudes of herself, she is amazing, new breasts, and goes to her regular job now, and the people there know that she is transforming. Some are good with it, and some are so so.  Debbie is dating her second boyfriend already, she is really a wonderful woman, and a great example of going with the moment!  I really love and admire her.  Love, Ms. Jennifer 1- 877-368-7505

She went out on Halloween and this is what she wrote.

Well, I took the big step on Halloween.  I went to the work dressed as a Sexy Nurse, well not too sexy.  I think I pulled it off nicely.  I wore a nurses’ dress and the other women in the office complimented me on how pretty I looked.  I could not believe it even the couple of women who do not like my choice to change sexes.  My boss did not complain.  Kendra came over early in morning to help me get my  makeup just right.   I wore my earrings and I have now continued to wear small ones each day, nothing fancy.  Everything is on the conservative side, but feminine of course.  I think, fingernail polish is next to start wearing, but nothing fancy or flashy.

Love, Debbie Lynn

News from Debbie – Call Ms. Jennifer for your transformation phone sex 1-877-368-7505

By Sissyplaytime July 7, 2016 sissy phone sex, Sissy Phone Sex for Panty boys, transformaton
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Sissy phone sex I do love it! Cross Dressing and Transformation and all the femdom fantasies that go along with the real thing as well. Debbie my girlfriend has had quite an active social life. Discovering she likes being a girl, she has gone to great length to transform. She has a new bf, and her family and has friends who know about her decisions, she is not telling me she is about to have her breasts done. Below are some of her updates to me.. xo’s Jennifer

Dear Jennifer, Mike came over last evening.  He brought me flowers and a gift.  The gift was a pair of garter belts and nylons, red and black, how original.  the thought was there though.  He apologized again.  To get on.  I ended up trying on the black garter and nylons and putting on a black dress with a slip.  While I was getting dressed, he ordered and went and picked up dinner.  We discussed his comment about another guy and I restated my “no” and he understood.  We also discussed his aggressiveness in sex when we first start.  He agreed to go slower.  Well, he won me over and we ended up having sex but it was slower but the surprise was when he unzipped my dress and helped me out of it and I had the slip on, he absolutely loved it.  None of his women dates had worn a slip.  He had me wear it during and I started on top controlling everything (even though I hate being on top).  Later, he tried to get me to orgasm and I mean he really, really tried.  I did end up with an erection for a short time but it was gone soon.  This morning before he left, I showed him my petticoats, and he said he would love me to wear one the next time.He is coming over again tonight, so I may put on the petticoat, we shall see. Love Debbie Lynn

Dear Jennifer, My co worker (the woman who saw me dressed up at the gas station) talked to me this morning very confidentially.  She mentioned it looks like I am getting breasts and it is noticeable under my shirts and suggested I try and cover up more or come out.  I was stunned, I did not think they were noticeable at all, the growth has been so slow to me, I did not think about what others were seeing.  Any suggestions.  I was thinking of wrapping with something but I don’t know what I will do.  It came as a shock this morning.Love Debbie
Dear Jennifer,I am not sure of Mike.  He came over and we were in the middle of a quickie and he asked if I would like another guy to join us sometime.  For both ends as he said/    Well, that was the end of that session.  I asked him to leave.  I couldn’t believe he would ask me such a thing in the middle of sex.  Still mad.  Am I just finding out how stupid and insensitive guys are?  Or am I just picking the wrong guys? Love Debbie

Dear Jennifer,Mike is delayed so I thought i would send this to you.  It sticks out, I have mine inserted before Mike arrives.  I am also wearing one of my petticoats, he asked and I have on a black garter and black nylons.  Since it is sticking out, it looks like an invitation for him to put his cock in immediately.Love Debbie

 

Princess Elizabeth will dig into your loser pocket’s

By Sissyplaytime February 28, 2015 loser phone sex

"tiny cock phone sex", "sissy phone sex"My Sexy Princess Fingers Digging Through your loser Pockets.
You wanna know a game I love to play?
Well read the first line above, stupid!
Pay attention jerk-off!
So for this game while I prepare for the game by putting on something
tasteful yet very sexy,
you prepare by going to an ATM machine and getting loads of twenties,
then you stuff them in your pockets. Can you do that loser?
O.k. good.
Now the big thrill for you in this game, loser,
is that I,
a perfect and Super Hot Princess
am going to get real close to you.
So close that you may even smell my sweet Princess breath as I berate you
and humiliate you
and yes,
you guessed it
I am going to meanwhile
be groping through your loser pockets
for those twenties that I know are in there.
The intoxicating combination of not only the close proximity of just about the sexiest Princess on earth, but with the sensation of her Perfect Princess fingers reaching into your pockets and robbing you right in front of your stupid loser face
All while teasing, taunting, and mind-fucking you.
It’s a real life Princess wallet rape and you will be left feeling used
and abused
and also quite confused.
Because
you are going to find yourself begging me to Use you again!
Call Me losers!
Princess Elizabeth for loser phone sex!
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My Number One Loser! JEFFIE Call Princess Elizabeth for your humiliation phone sex

By Sissyplaytime June 27, 2013 humiliating, humiliation phonesex, little dick, little dick humiliation, phone sex
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Loser

Princess Elizabeth loves to humiliate and torment Jeffie her little dick loser! I like to make him do very humiliating things. He loves Humiliation phone sex with his perfect Princess, ME,

This is what my Number # 1 loser has to say….Thank You for owning me Princess! you were right, you are making me a bigger loser! you are making me weaker and weaker! And more and More Addicted! I love my perfect Princess! I want so badly to please you!!!

HERE IS MY LOSER! WITH HIS BLUE BALLS! **giggles** Princess Elizabeth