3 minutes of Free Phone Sex with Princess Jill: Sissy Humiliation Phone Sex

Archive for June, 2008

Saturday, June 28th, 2008

Forced Feminization Phone Sex

This morning I was thinking about how nice it would be to snag an older husband and inflict forced feminization upon him lol. What a sadistic little witchie poo I am lol. Training my old loser of a husband into full feminization would amuse me so! I would make him wear girdles and panties, and teach him how to tuck his little clit to make his mangina so pretty.

perfect mangina

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Monday, June 23rd, 2008

Sissy husband phone sex

I really love it when I catch a sissy husband rummaging around in his wife’s panty drawer or through the hamper. They will call me up for sissy phone sex and tell me, I was just going through my wife’s panties and she doesn’t know I do this. I found a really pretty pair of panties and I feel like such a dirty sissy slut, Princess. They really get so very excited, they start dribbling and make a icky little wet spot in their sissy panties.

oh caught me with my little clitty hard

Is this what little sissy husbands like you do when your wife is away?

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Friday, June 20th, 2008

Sissy phone sex: definition of a sissy

Good morning sissy boys. I was just doing my usual morning reading that I like to do mostly because this morning I was thinking to myself what really defines a sissy? Well this is how Wiki defines a Sissy

Because of its origins in a feminine nickname, sissy is also a pejorative for a boy or man to indicate or imply that he is like a sister, that is, effeminate and fails to behave according to the traditional male gender role. Generally, it implies a lack of the courage and stoicism which are thought important to the male role. It might also imply interests seen as strikingly un-masculine. This pejorative may be given to anyone as an insult. Several variations, such as “sissy boy” or “sissy baby”, exist and any term can become pejorative or insulting if preceded by “sissy” and applied to a boy or a man. Sissy is the male converse of tomboy, but has none of the latter’s positive connotations. Even amongst gay men, behavior thought of as sissy or camp produces mixed reactions. Some men reclaim the term for themselves. (See also genderqueer). Other similar terms include “wimp”, “wuss” and “femboy”.

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Monday, June 16th, 2008

Free Phone Sex: Sissy phone sex

Most people are still skeptical about the free phone sex offer from niteflirt. I come across many sissy boys during my day and they really don’t believe it’s free to have sissy phone sex with me. What’s to lie about? All new callers get 3 minutes of FREE phone sex when they join. I thought I would give you some more small penis humiliation since it’s such a hit. A few of my sissy sluts sent pictures for me to laugh at and well I thought I should be generous and share their pictures with the world.

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Sunday, June 15th, 2008

Small penis humiliation: small cocks suck

Small cock pics are funny. Have you ever just surfed around on the net to see what you can find to amuse yourself? Well tonight I am seriously bored and I started looking around to find something to make me laugh. Guess what I found? Tons of small penis pics from sissy boys showing off their small cocks. Fun times for me with the small penis humiliation.
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Thursday, June 12th, 2008

Sissy phone sex with Jill

There really isn’t anything more entertaining to me than doing sissy phone sex. The sissy boys who call me are so completely effeminate and so into their sissy roles that there is really no getting them to break character. It’s incredibly fun to think of new ways to get a sissy boy excited by coming up with new sissy training or sissy stories in order to get into that sissy’s headspace.


Silly little sissy boy ruffling his frills


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Sunday, June 8th, 2008

Wannabe sissy boys need serious training

Well, lol I should have known that once I started to put it out there that I was looking for sissy maids to train that the little pathetic wankers would start crawling out from under their rocks and send me wanker mail. Ick, this one guy Doofus or something lol I don’t know what his name is but if he sends me another wanker email he is going to be blocked. Honestly, I don’t know why I didn’t block him already. Sometimes I just don’t pay any attention at all to these pathetic little sissy boys because that is what they crave so much, attention. What a sissy like this really needs is degrading humiliation. I mean some raw, unadulterated humiliation up his sissy ass lol. Hmm, I don’t know or maybe he needs a good ass fucking to shut his little whiny ass up once and for all. Whatever the case, he needs to realize his place and a good humiliation session is just the thing to cure him of his uppitiness. Stupid little sissy.

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