Some people approve.

Ron was apprehensive about going out to such a formal and such a public festivity. He thought the dress and his breast forms might not work as well as he planned. At least he could fool someone.

Unsure of himself.

Ron didn't know how long he could stand in front of his mistress, and his tuck still stay in place.

Does my butt look okay ?

Ron turned to his girl friend and asked," Does my butt look okay?"

"Yeah, I suppose so."

I like this poster. So I am reblogging it. Wish I could remember where I got it then I could give them credit.

What a remote.

Ron didn't know his girlfriend was so good in electronics. She had actually programmed their neighbors TV remote ( how she got a hold of it she would never tell) to set off his remote vibrating butt plug. They were always channels surfing. Can't wait for late night.

 

Haw far can I go?

She told me to dress up in the dress and lingerie that she laid out for me. She said I had to walk to the café and wait for her. She said it would be one of my gurl tests.  But to wait here, and just see how many guys think that I'm a girl and not a boy. I have to be polite to all the guys hitting on me.  She thinks I can fool all of them. But I'm starting to think that I can fool them, but i'm also wondering how far can I fool them.
I'm thinking it would be fun to see how far I could go.

 

I think I could go pretty far.

Caught by his room mate.

Steve didn't know his room mate had gotten home and

was watching him after he had put on all of his girly stuff on.

 

Steve knew a way to keep him quiet.

You're welcome to stay.

Yes, I know it is inconvenient, but I can't leave the house. 

If I do,  I end up turning back to into a boy.

I was so unhappy then that I don't want to change back. 

Even if I have to stay here in this house naked all the time forever.

I can't leave, I won't leave.  I'm happy now.

 

 

But you're welcome to stay.

If you don't mind changing into a girl too.

Just checking

Even though he had been taking hormones for a long time,

his wife still liked to check and see if his breasts were still getting bigger.

 

 

I'm Game

It is so nice to go out, isn't it ?  And you have to admit you do like going out to.  You seemed at first to be hesitant. But now that we are out you seem so much more relaxed.  I have to laugh to myself about how you gave this impression of such righteous dude when I asked you to wear those panties.  It was no big deal. And it really isn't hiding a big deal. I mean that little thing that you have hanging. No that's not the word. It sure doesn't hang. Maybe pokes out a little. And that is when it's hard. Yes, hard. and I did see that you got hard when you were putting those panties on. But still even when you are hard it isn't much bigger than when a man would get out of an ice bath.
Oh My I seem to be doing all the talking don't.  You just sitting there with your hands in your lap,  looking down and studying the plates and silverware.
Oh yes.  I am the Dom now.  Right ?. I have all the power, and you do as I say.  Now I get it. I never really thought about this before. Well recently I did. Some things at first didn't add up. do you remember some time ago when we were making love and I kissed your nipples and you sighed so. I thought then that your skin was so smooth, just like a woman's.  Not that I have ever kissed another women's nipples before.  But I can imagine. But you seemed to have reacted the way I do when you kiss and suck mine. I do love that.  ANd you seemed to love it so too.  We should try you in a bra sometime.  Do you think you would like that. I think if you were naked I could tell if you did, by your reaction. Just like the panties maybe ? Getting hard thinking about it ? 
I'm glad that you are a musician and go for that thin man look. And your long hair. We do have to get it styled don't we?  Then I think that we can come back here and have dinner again. Just the two of us. You can wear this dress then. I'll find a leather mini to wear. But I think we have some work out first. Then we can move on to do some of those things that they do on places that you visit on the web.  Yes I know. You do forget to delete you browser history once in a while. You got me upset once when you changed it to delete itself at the end of each session, but I didn't like that.  I wanted to go back and check out some sites that I visit regularly. When I did that I discovered some of your sites.  Oh my.  That's when I learned about your cross dressing fantasy.  And then so much more.  The Sissy sites. At first I thought, No not my hubby. But I guess so. And pegging ?  Well sure I'm game.  In fact I think after we leave here we should go to that adult toy store that is in town and get a strap on. What to you think? I'm game.

They have to be just right.

Ron was always a perfectionist. It would take him hours to get ready to go out just for a couple of minutes. Now you can see he is making sure his breast forms are exactly in the right place.

But tonight is different. Tonight he plans on staying out all night.

 

He really did want to go out clubbing.

 

Ron's sister was going to school for make up and photography.

She had a project that she was due in a week and her friend that was going to do it had canceled.

She asked Ron if he would sit in, as Rachel and him looked very much alike.

Sue, his sister, had him come over and he put in hair extensions. Plucked his eye lashes and, put on breast forms and make up.  Ron had to admit that he looked pretty very much like Rachel.

 

 

 

When He got to the studio, he found that they had a bar for drinks so models could feel a little bit more at ease. He had a couple of drinks, and his anxiety about the situation seemed to ease. 

At first it was just a couple of head shots and Ron thought this is no big deal.

Sue asked him how he was doing and he told her fine.

 

"Are you ready for the next set?"
"Sure, bring it on Sis."
Little did he know that there was going to be some other models here and that they would all have to pose together. Each model had a different photographer and each model would be the main subject for shots with her photographer. What got Ron nervous was that it was a bikini shoot.  Oh well.
He changed and had another drink. He was feeling pretty good now. His sister turned up the music and Ron  started to have some fun.

This went on for a bit. He had almost fallen while wearing the heels.

Ron breathed a sigh of relief, "we almost done?"

"Yeah, just a couple of other shots first. We have to wait for every one else to leave."

"For them to leave?"

"Yeah it's a nude."

" Oh Shit"

"Oh you'll do fine."

"Okay, everyone is gone, go strip."

"Uhmm, okay."

Ron came out just wearing his watch. He was very embarrassed being naked in front of his sister.

Sue looked at him and said "you should have been a girl. "

""So after this you want to go out get a bite and hit a club?"

"Do you think?"

"Oh heck yes, no one will know."

'Well, okay."

"So go sit over there and we'll take our last set of shots."

He sat down nervously. The tape that was holding his little cock was coming lose and he

was so excited that he thought he may cum now and ruin everything.

 

 

He really did want to go out clubbing.

 

 

 

Magic with string.

Ron was impressed what just a couple of pieces of string could do.

 

Home Alone at last

 

Ron finally got to have the house to himself after his room mates left for the summer.
He put on his special red panties and crop top  and white stockings and played loud music and
started to have a one gurl party. At least for a while till some of his other friends came over.

It seems like just a little kiss at first.

 It started pretty simple at first, just a pair of panties. Then you had to know what a bra feels like. Then the stockings, which were to die for.  Soon you found a dress and a skirt and top at the thrift store. You thought you looked good, but you had to have that wig and now you look great. Well now you're getting pretty passable so when the make up came you practiced for a while and then really started to think differently.  You went on line and you met a nice guy. He said he'd buy you a drink, if you wanted to meet in an out of the way bar. He was just passing through he said. You met him at the bar. He flattered you till you were blushing. He bought you a few more drinks. He put his arm around you. You put your hand on his thigh. You were laughing together.
He invited you to his room. Well just for another drink you said. He had his arm around you and you had a hard time walking. In his room he kissed you. You swooned. You both got hot and bothered. He understood that you didn't want to get undressed completely.  He did get undressed.
You took a hold of him. Your blood was boiling. You are closer than you have ever been to anther man's cock. He holds it for you and says just give it a little kiss.  You do, but you know a little kiss is just the start of something that you feel will soon consume you.

Really ? you want me to do that.

Ron Looked at his mistress astonished "What? You want me to do what?"
"You heard me."
"Yeah, I did but I can't believe you are asking me to do that.  I thought it was being pretty outgoing just coming to this lingerie show. I mean how many guys dress up in a skirt, wig and make up and go to a lingerie show?"
"Rhonda. I told you to do something. I am your mistress and I am not going to be happy if you don't do as I say. I will humiliate you here if you don't do as I ask."
"Okay, but I don't know what or how to do what you're asking."
"Rhonda, Just go back stage and ask for Kaaren.  Tell her that I sent you and ask her if she would help you with picking out some lingerie for the show.  She should know what will fit you. When you are done, remember to tell her thank you and show her how much you appreciate her help. Now go before the show starts."

The conditioning should start to work.

Ron was plagued with anxiety. He thought that when he went to college that things would get better.
But to no avail.  As college went on, he tried to help himself relax by using alcohol, which led to more problems.  When his grades started to drop, one of his professors told him hat he should get help at the student counseling center. He went and met a very helpful woman, that started to teach him how to relax.  During his time there he discovered that he really didn't know who he was and what direction he wanted to turn to in life. She told him that with time he might be able to find those answers. 
She started him on some meditation exercises. Here he would just sit and learn to relax. She taught him to go to his happy place. There he found he could truly start to relax. He could  close his eyes and hear the waves rolling up to on the shore. He could feel the gentle breeze.  She told him that while he as in his happy place, that he should start to try to look for himself. That he should imagine that he could see him self on the beach. He at first started to see just a grey blob which he felt as formless. As time went on and he stayed relaxed he was able to start to see that the form was female.
He asked his counselor how he would become to learn to be the person that he saw. She told him just relax and see if he could see and feel things that the person he was seeing was feeling.
Initially he thought this was bogus.  But he had felt that things had moved in the right direction so far that he should try it.  He projected him self into the image he saw and started to feel the waves hitting him. He could feel the breeze.  Soon he began to feel the of the tickle of his hair on his shoulders, then the fluttering of the fabric of his bikini top, the warm sensual feeling of the sun on his skin.
Then he knew real peace and it brought a smile to his face. He knew he had found his true self.
When he met with his counselor, he told her that he felt he was finally at peace with himself and could move on. She asked him what he was going to do to get to be his ideal self, somewhat  knowing who he was to become, and yet happy for him that he had made such a great discovery this early.  He told her that he would start by first growing his hair longer. She smiled at him, knowing that the conditioning was going to start working.