Category Archives: Slut Boys

All Ready For Girly Bedtime

 

This is one of my sissy friends that I have played with for YEARS!!! He is really good about putting his panties on every day and is currently looking for a cock to suck and worship. I know not everyone is into that and its okay if you are not. However I like it when my sissy’s actually live up to being who they desire to be. He is far more advanced then a beginner just because he has years of practice. Don’t worry if you are starting out you can catch up if you try hard.

rydoll

Pretty Black Toenails And Purple Flip Flops

 

Another awesome fun shopping trip with one of my sissies. These are just so girly and my sissy still wears them all the time when they are home alone. I think it is really important for a “girl” to connect with herself at all levels. Some of the most important things are panties, lip gloss, girly shoes, and panjamas. Just think about going to bed every night in all those things. You know those dreams will be awesome.

ryflipflops

Is it Tiny?

 

 

Yes It IS!!!! Not the tinest one I have seen but it comes in that category. Now why would a man ever think that his thingy this size could or would ever please a woman in any way.  We like a man that has a manly shaft to him. Yes no matter what your wives lie and tell you size does matter. No women do not like sex once a month. Yes they are telling you know because you have a tiny little pecker that no one wants to play with. Don’t you worry she has some real toys hidden somewhere.

rypastel

First Bottle of Nail Polish

 

 

Sent one of my sluts out to buy their very first bottle of nail polish. Granted it was not what I would have chosen for myself a little to neutral of a red for me. However, he was very proud he went to the drug store stood in aisle and chose it with all those other women standing there. Taking it up to the counter and knowing that the girl standing there knew he was buying it for him, left him feeling so girly and vulnerable. He then got to go come and paint his toe nails for the very first time. Such a great experience for all sissy boys.

rypolish

Electric Play

 

 

This was one of my first guys that liked to play with electricity. I had never even heard of a tens machine until we started playing.  I quickly learned all the fun things that electricity has to offer though and really enjoyed hearing him beg for mercy.  I spent many an hour lightening up his cock and balls. I even got to play with a butt plug insert so that he really started to plead good. I would laugh so hard my cheeks would hurt. Unfortunately or maybe fortunately his life changed and he got remarried so we no get to play like we used to.

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One of My Favorite Sissies

 

 

It is hard to tell from this picture but this whole room is done up in girl fashion. From a pretty white and pink sex swing to gorgeous pink everything else.  She is always done up in a whig and makeup and just flat out fun. Nothing makes a session better than someone with a great sense of humor that really enjoys what is going on.

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Pretty Zebra G-String

 

 

So G-strings are harder to find these days they have went out of style in a lot of ways. Not sure where my friend found these, but they do look adorable. We had not gotten to the lesson on proper shaving techniques yet as you can see. Everything is a lesson and a journey and this was one of the first steps for my sissy.

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Painted Toes

 

 

For me training a sissy boy is kind of a ritual and I enjoy all the different parts. One of the first things I do is make my sissy boys paint their toe nails. I really do not care about the color most the time they choose a pink or red. My enjoyment is forcing them to wear that under their everyday clothes and socks. This is generally a very big deal to them at the end of the day. They spend the whole time thinking about that one little part of them that no one can see that is so girly. Even the act of painting them starts to take on a lot of meaning for most guys.  This is one of my sluts pretty toes after I made him paint them and wear them all day to the office.

rytoes

Starting To Dress Up

 

 

Some of my guys I have talked to for years. This is one of my sissy guys that ordered some stuff off line.  It depends on the guy but some of them I enjoy making them go out to shop. Not every sissy can handle this because of the level of embarrasment so I have to adjust to personality. It is a lot of fun to shop online together as I generally do not live anywhere near the guys that I play with. I have had a few transgender and crossdressing girlfriends that were close to me. We would always enjoy taking some time and hitting the mall together. Most of the “girl” that I knew where more conservative in dress and most dressed 24/7 so it was all slacks, skirts, bras and panties. The guys on line that just dress for fun time tend to want the more slutty fuck me know look. There is nothing wrong with that and lots of fun to play with but getting fitted for it at the mall by a teenage girl is generally way over whelming.  If you would enjoy showing off some of your outfits send me a picture or two and tell me a little about it in an email. dianecallaway@gmail.com

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