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Read other member blogs or start your own. Chastity, D/s, Femdom, Cuckolding, Relationships, Advice and more...

Tag >> Crossdressing

Yesterday my girlfriend decided that she would like to go out for evening and that it would be nice, if I will go with her in high heels. First she wanted me to wear also a skirt, but later she was so kind to me, and let me just wear the high heels and pantyhose under the trousers. And of course, she locked me to CB-6000 in the morning before she left to work, to be sure, that I will be looking forward for the evening and will not touch myself during the day.

After she came from work, she started to pick up the right outfit for me and finally decided, that I will be wearing CB-6000 hidden in black satin & lace panties, sheer pantyhose, diesel destroyed jeans, so the pantyhose will be visible if I sit down, black shirt and black 4" high heels with the rounded toe and silver metal flower in the front.

When I have put everything on me I have realized that in the simplicity is the power. I felt very comfortable, and at the same time I felt very feminine and masculine. The feeling of the jeans on top of the pantyhose is very teasing and reminding me, that I am wearing the women clothes. The high heels were causing my legs were looking longer and the whole posture was improved. At the same time my locked cock reminded me, who is in control. She also made me light make up and mascara, and my hairs. I was promised that if I will find courage and go with her out, than at the end of the evening I will be rewarded... Sounds promising, what do you think? ;)



Geeze i think i picked a rather apropreate haddle for my self beacuse im really confused about this one maybe some one can help claify?
 
Ok this is what i don't understand, I've been on this site roughly 6 months now give or take , I've had 127 people kindly take a look at my profile and not one, not one person has left me a message or even a comment or rated my page OR has even had the courtesy or responding to any of my emails :( geeze depressing much? not Im not looking for all kinds of attention here or anything of the sort, but it would be nice for at least one person to acknowledge i exist? what do i have to do? get a cute pink chastity and slip into a pair of panties before some one notices me? or even a frilly pink latex dress and high heels?? i just don't understand how or why a lot of these middle aged, over wight, and out of shape men, bois ,sissies are finding key holders to there chastity, look Im 23, thin, fit, VERY neat and clean AND yes even a virgin ( including my behind ) Im not a hideous shud or anything some have said even a tad Feminine, well maybe more then just a little, so what is it exactly about me that people find so offensive? now that thats all out of the way, let the great experiment begin! ( you'll see what I mean later)

Its Friday June 25th, 20 days denied cumming and only had 3 minutes of "her" puss this month. My Wife is still threatening to "break" me and push me into September before releasing me and allowing me to come.

I received my new solid, unhinged ring for my CB-3000 and she instealled it yesterday. It is a LOT more comfortable and it came in 2 days. I went biking and swimming yesterday with it on and had no problems.

As the blog showed my ass had been tapped almost 3 times this week and I was content with gettign a night to relax. Mistress and I had talked about fooling around( which means me getting fucked) before she left for work, but after being in the hot Summer heat doen South, I was whooped.


I ended up not having to go out of town for business, and since the kids were at the beach we had an empty house until Wednesday..whoo hoo!

My KH had come home from work and was pleased that all the laundry was done, as well as the kitchen cleaned up. I was covered in sweat at 500pm since It was 92 degrees and I had finished mowing the lawn.  "My Lady" directed me to fix her a cocktail, then go take a shower, scrub my cage real good and shave my legs and ass/pussy. She had already texted me earlier in the day to "eat light" and that she had plans for me since she was excited my business trip was cancelled last minute. I knew that meant to do an enema as well. I retired back to the bedroom and handed her her coktail....

She sat down at the PC to check our blog comments and PM's and it put a big smile on her face hearing the feedback and compliments on her attractiveness :)


Gonna keep it short and sweet this morning cause I have chores to do. Its gonna be in the 90's outside today and the kids are at the beach with family until tomorrow. My KH is at work, but she left instructions to clean the kitchen while wearing the red fishnets seen in previous post, heels, lace undies and a pink silk top. I must send her cell phone pics each hour to prove I am still dressed as her sissy, and I better hope no delivery people or neighbors come to my kitchen door!

Yesterday my Mistress slipped up while she was sucking my plump nipples while teasing me and said that 50 days seemed like a good number to make me go without cuming.  June 5th was the last time I came so 50 days is a long way off. While at work I stopped in a WALMART and had a new tag made that says "Going for new record or BUST." They are only $4 and seem to put a smile on her face when I suprise her with creative sayings.


Last night after a long day at work my Wife and Keyholder went to a neighbor's pool party. When I arrived home at 530 she already had on a sexy outfit which included high heeled sandals and short, sexy shorts. Her legs are incredible, IMHO,  because of the exercising and running she does. I love the curve and belly of her hamstrings and her thighs are rock solid, as my ass cheeks always feel slamming into them.

She wasted no time picking out a pair of red lace panties for me to wear, the kind with the horizontal rows of lace frillies front and back. She was tingling inside because she knew a dozen of our closest friends were going to be there and I would be caged in front of them.  I was already excited just seeing her dressed in heels and its been 13 days since I've cum...or 14th....its been a WHILE.


Last night my Wife/KH decided to have some fun with me. I guess I can't complain because she let me out of my cage, although I was tied down spread eagle first. Prior to this she made me model my garterbelt and stand in spikey heels so she could take pics to post here and embarass me.

She's loving the email compliments :)


As a follow on to moving to larger breastforms, my wife agreed to ask this forum for advice. If you read my previous post, you know that she now wants me to wear larger forms. I have been resisting this. She ordered a larger set, so now we have three sizes. Below are some pictures of what the three sizes look like wearing the same shirt and using the same bra. We would like your thoughts as to which "figure" you all think is the best looking. 

Thanks for your help...

Here is a picture of the bra used. A very nice underwired unlined Vanity Fair full coverage bra.


Well, they finally arrived. My wife decided that it was time for a "boob job" and move from size 4 to size 10 forms.She has had me wearing a bra and the smaller forms for about 2 years almost every day. Since I have a big frame, they are not very noticeable under a loose shirt unless you looked hard.  The Wife feels that I should always be reminded of my subordinate role and her control of not just my cock, but all aspects of how I dress and what I do or don't do.

I guess I was getting just a little too comfortable and a little sloppy so she decided to make a more visible statement so to speak. We went shopping last week, and I was directed into Macy's to purchase three new bras. For my forms I prefer a underwired demi-cup bra, and a "B" cup push-up bra for regular wear. I picked out three nice ones, size 40B, and started to walk to the check out stand. As I approached it, my wife suddenly grabbed the bras and started into me about buying the wrong size. 

Rather loudly it was made clear that I was supposed to get a 40D cup, unlined with full underwire and plenty of support. She asked how did I expect a "D" sized breat to fit in a "B" cup, and so on.... With that she asked one of the clerks where the plus sized full support bras were. The clerk, probably no more than 20 years old, led us to the back wall, and suggested that Bali made by far the best full support bra. 


I am a happy little sissy this morning!
Last night Princess started my training properly, YAY!

I dressed up in some sexy lingerie (stockings and basque) while she worked on cam, and I was her maid getting her drinks and cigarettes when she needed them.
After she had finished work she made me get my underbust corset out and to put it on over my lingerie, she tied it nice and tight, making my waist shrink down and be hour-glass shaped. :-)
She then proceeded to take some pics of me (online soon!) and carry on drinking and teasing me for over 4 hours! :-P
I was so desperate to put the strap on on and give her a fucking of a lifetime, but she wudn't let me, so got her riding crop out and gave my tight ass a good whipping! YAY! Some of the strokes wud sting and it wud make lil drops of precum dribble out of Her cock (as I've said before, it's not my cock anymore).
I loved it, feeling the riding crop crack onto my flesh and stinging, hurting deep into my ass cheeks and making me feel sooo horny! Knowing Princess is in charge, that she will administer training and punishments as she sees fit onto Her little sissy subboy. YAY!

Finding a Name for Her Sissy

While she was teasing me and playing with Her sissy, Princess started to think of names for Her pet. I told Her the name I had sometimes used myself but She didn't like it so I wont even put it on here. She liked Ruby, and called me Ruby throughout the night.I love having a sissy name! It allows me to totally get into my role. I can drop all pretext of me being in charge. I want a womans name chosen for me by my Princess. I am the one who needs a name that is fitting for a little sissy like me, not a man's name, a girly name, a sissy name! :-)This morning Princess isn't so sure on Ruby anymore, so I am still waiting to find out my new sissy name that I shall have.Hopefully She will choose a name for me soon!Once She has decided on my new sissy name I will change my profile name to it :-)

Scary Punishments!

Princess read my blog yesterday about how I have been snapping at the drop of a hat and she has decided that she has worked out a list of punishments for various misdemeaners ranging from a light spanking, through to a heavy whipping, right up to a full blown public humiliation that will involve, I'm told, going to seedy Gay Bars and then onto a Gay Club where Princess will make me get completely out of it and offer me up to the men there to use as they want! Where I wake up is anyones guess She says! I plan on being a good boy! But I now know She means business, the look in Her eyes when She told me this was deadly serious, I love it! I love how She wants to use and abuse me! I love to be humiliated! I live to please Her! And I know that this punishment in particular would please Her very much, even though it would be extremely embarassing, awkard, scary, and more for me, if She says we are going I will not put up a fight as I know I will deserve it. She is the Boss, I am the sissy sub that lives to service Her.

I Love You Princess xxx

When we did go to the bedroom, I put the strap-on on and attached the big black dildo She loves so much. Thrusting in and out with such a big dong into Her beautiful pussy made the cock swell in it's cage while she would push down onto the dong and make Herself come over and over.
When She was satisfied Princess pushed me off Her, said I had been a good boy and rolled over to go to sleep. I was left to undress myself and clean up, with no relief of course!
I love it! This is how a relationship should be! I can pleasure my Princess and follow Her instructions and She can be assured of my devotion and happiness in serving Her. :-)

Thanks for reading!

a happy sissy


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