My transgender experience diary

[T.H. Oughts]

I hope you all don’t mind but I don’t really have a lot of friends I can talk about this too so I’m coming here to tell you all….

I met a man a while ago and we have hit it off well. It turns out that we both have a fetish that if different from each other but they both go hand in glove…. He wants to get in better contact with his fem side by dressing in woman’s clothing and having a woman take him and I want to take a man dressed as a woman with a strapon..
…

So far we had only met in public places… Today we met at my place to talk boundaries…. Wonderful, either of us doesn’t want someone hanging off our coat tails 24/7 and we are both happy with our lives with no baggage… I told him the fem name I have given him. I will use that name when we are in play mode..

So one evening this week are going shopping for stockings and lingerie for her and then back to my place where I shall bath and dress her and then I get to have my wicked way with her…

I have some lovely sensual male to female words and actions I have thought I can use while we are in public, when he is dressed as a male but being female inside.

This is so damn exciting…. I have always dreamt of something so sensual happening and now it is… I don’t think I’ve ever been this wet or horny ever!!

I'll keep you all updated...

 

[madmanmike]

do keep us informed. by the way if you do him doggy style make sure to slap his ass and hold his hips and pull them torward you and do a hard grind.

 

[Lance Hardrock]

I'm interested

You know I'm all ears about this.

I want details, lots and lots of juicy hot sexy de-TALES.

 

[rcuhljr]

I'm going to be coming back to this thread

 

[T.H. Oughts]

You know I'm all ears about this.

I want details, lots and lots of juicy hot sexy de-TALES.

Mmmmm she has such a fine tale too.

 

[robbie_boy1]

Mmmmm she has such a fine tale too.

lol....Ms and i can't wait to hear of you exploits. we just love kink that makes people happy. You rock!!

r

 

[T.H. Oughts]

lol....Ms and i can't wait to hear of you exploits. we just love kink that makes people happy. You rock!!

r

I can't wait for them also....

I've just been searching for a feeldoe that a lot at Lit say is a good. But it looks like you can not buy them in New Zealand.

http://www.thesassykitten.com/Merchant2/graphics/00000001/feeldoevibe.jpg

 

[Metrodance]

He wants to get in better contact with his fem side by dressing in woman’s clothing and having a woman take him and I want to take a man dressed as a woman with a strapon..

Is it just a fetish or a life change?

 

[Lance Hardrock]

I can't wait for them also....

I've just been searching for a feeldoe that a lot at Lit say is a good. But it looks like you can not buy them in New Zealand.

http://www.thesassykitten.com/Merchant2/graphics/00000001/feeldoevibe.jpg

That looks awesome. Can you order it online?

When I get to NZ, you are most welcum to use that monster on me.

 

[T.H. Oughts]

Is it just a fetish or a life change?

Just a fetish.... We are both happy being who we are in public, we just want to be someone else for a while a couple of times a week.

 

[T.H. Oughts]

When I get to NZ, you are most welcum to use that monster on me.

Only if you do as you are told.

 

[Lance Hardrock]

Only if you do as you are told.

Of course, mistress.


*bows deeply from the waist*

 

[T.H. Oughts]

Of course, mistress.
*bows deeply from the waist*

Quckly now, straighten that apron of yours and clean my boots, stopping every few seconds to suck on my cock!

 

[rcuhljr]

Quckly now, straighten that apron of yours and clean my boots, stopping every few seconds to suck on my cock!

Well there goes this pair of boxers.

 

[Lance Hardrock]

but of course

Quckly now, straighten that apron of yours and clean my boots, stopping every few seconds to suck on my cock!

*hastily straightening apron and licking boots clean*


Every few seconds I suck on your cock and slide my mouth up and down and all around your big hard cock.

 

[T.H. Oughts]

*hastily straightening apron and licking boots clean*


Every few seconds I suck on your cock and slide my mouth up and down and all around your big hard cock.

Very good, but next time take longer strokes on my cock.

 

[T.H. Oughts]

I made a type of baby doll outfit today. I had to put it on a mannequin too photograph it as my daughter is home today. And yes the mannequin is smaller chested than I, but the fabric will stretch to accommodate myself.... I think I might give it too my lover for her to wear???

 

[Teman01]

looks good

I made a type of baby doll outfit today. I had to put it on a mannequin too photograph it as my daughter is home today. And yes the mannequin is smaller chested than I, but the fabric will stretch to accommodate myself.... I think I might give it too my lover for her to wear???

God I love your avatar. I get hard just looking. Your baby doll would look smashing on you especially with the top stretched and all that cleavage. However I think your lover would be turned on wearing it and some of the guys on here might get a hoot out of seeing her in it.


Jake

 

[T.H. Oughts]

God I love your avatar. I get hard just looking. Your baby doll would look smashing on you especially with the top stretched and all that cleavage. However I think your lover would be turned on wearing it and some of the guys on here might get a hoot out of seeing her in it.


Jake

Thanks Jake. I don't know if she would be into posting photos... we shall see as time goes on.

 

[Teman01]

Thanks Jake. I don't know if she would be into posting photos... we shall see as time goes on.

I'll will be nice to hear out it turns out

 

[gingermango]

Please let us all know how it turns out; being taken by a powerful, dominant woman while "dressed" is one of the hottest experiences I know. I love to hear how it goes for other people, especially from the woman's perspective.

A couple of months ago one of our play couples came over and the girl (a beautiful 22 year old with long silky blond hair) fucked me over the bed while my wife was making out with her 27 year old boyfriend. It's the only time (so far!) that I've been taken by another woman since I got remarried and it was fabulous!I t was so incredible to feel her pumping into my ass while her hair drifted across my back and looking up to see my wife being pleasured by another man. We're so sad because they just moved for work reasons! So in between sessions we like to hear how much others enjoy it, too.

 

[Stefani]

So one evening this week are going shopping for stockings and lingerie for her and then back to my place where I shall bath and dress her and then I get to have my wicked way with her…

T.H.,

Sounds like you're about to start on a fun adventure. All the best to you and your "lady" friend.

Your comments reminded me of when I was young and just starting to explore gender roles (I am a pre-op TS).

When I was in my early 20's and just out of college I met a woman twice my age who loved feminine boys. When I nervously described to her my interest in crossdressing, I will never forget her reply. She said, "Let's go shopping!"

The first place we went was a woman's store at the mall to buy a dress. As this was all new to me, I was quite nervous. It didn't help that she kept holding up dresses against me, and saying loud enough for anyone to hear, "I wonder if this will fit" or "This would look cute on you." Remember, I was a young man at the time, so was totally mortified.

Eventually she picked out a couple of things for me to try on and we went into a changing booth, where she ordered me to strip down to a pair of red women's panties that she'd given me that morning to wear. Again, I was highly nervous, because I could hear mother's and their daughters around us chatting away in the other booths. Lynne absolutely loved my discomfort, she got off on things like that, it totally brought the Domme side out in her... and the submissive side out in me.

Anyway, I tried on the dresses she'd picked out, but none fit, so she left me to go find more. I stood there in my women's bikini underwear, my heart pounding so hard I thought everyone in the store could hear it.

Eventually Lynne returned... but she wasn't alone! She brought a sales woman with her! The woman was about 30something, attractive, and carrying a measuring tape. Lynne told me she wanted her to get my measurements so we could figure out my dress size. I nearly died!! The woman simply smiled when she saw me blushing bright red and said, "Don't worry, a lot of transvestites shop here." She put the measuring tape around my hips, waist and under my arms, with me shaking like a leaf. Lynne was having a merry time with all of this, she knew she'd blown my mind, and was loving it.

They decided I was a size 10, and Lynne went out and gathered up some more dresses, and we finally decided on a short black dress - the first of many that I would buy over the years, and one that is still special to me simply because it was my first.

That night Lynne did my makeup and hair, and I tried on my new dress with a pair of her nylons and heels. I'll never forget that night, because it was the first time I ever saw myself entire enfemme. It was like seeing the true person in my soul. I was utterly entranced by my own reflection.

I would have been quite happy just to sit in front of the mirror all night, but Lynne insisted that we go out. The thought of going outside the house dressed as a woman scared me half to death, but Lynne insisted, and Lynne always got her way. All we did was drive around the neighborhood... but it had me shaking like a leaf. She even pulled through a McDonald's drive-through window, just to see me squirm. I kept expecting people in the cars on the road around us or the woman at the drive-through to point at me and laugh - but nothing of the sort happened. I was young, slender, and feminine in appearance, so people didn't seem to notice. Lynne kept saying, "Relax! You're fine! Just enjoy it."

I will always thank Lynne for what she did for me. She gave me the courage to explore something I'd dreamt about all through my teens. I doubt very much that your "lady" friend wants to go as far as I have, but I have to say, she's quite lucky to have found a woman like you. Trust me, I know, there really aren't all that many straight women interested in this sort of thing.

Lynne was quite a woman. I ended up living with her for a year. She was inventive, supportive, and sexy as hell. She could weild a strap-on better than most men can wield their own penis. You sound quite a bit like her. Have fun!

Stay sweet,
Steffie

 

[rcuhljr]

Wow nice post Stefani it sounds like she was the perfect woman for you at that point, a lucky find on your part.

 

[Teman01]

Stefi

Thanks for sharing you are just so hot

 

[T.H. Oughts]

Sounds like you're about to start on a fun adventure. All the best to you and your "lady" friend.

Thanks for your memories. I don't think we will be going out in public with her in dresses. He is quite happy to be dressed as the man in public. Though when we go shopping tonight I will be in control of shopping for her.

We both enjoy the male and female parts of our souls. So we will swap about when the need is there.