Remembering Your "Firsts"

I've been at this crossdressing thing for a long time. I remember when I was young, in my early 20's, and I found a support group in my area. I attended a gathering, hate to call it a 'meeting', more of a social event really... and talking with some of the older, experienced crossdressers. I wondered at the time if I would still be doing this in 20 years, 30 years, or even into my later years. One of the 'sisters' told me that it never goes away. You know, she was right. I know I will be doing this for the rest of my life. I have even told Linda that when I die, I want to be buried in something feminine and she has promised to do so.
So that got me thinking about some of my 'firsts'...

Do you remember the first time you put on something girly?

... the first time you got caught?

... the first time your dressing was 'exposed' to others?

... your first feminine clothing gift?

...How about your first sexual experience as a 'girl'? Was it with another girl, or was it with a guy??

... How about the first time someone watched you have sex as a girl with someone else?

 I have some fond memories, made many mistakes, done some things I wish I hadn't. But I have also had some great times and done things few others have been able to try. All in all, looking back, the only regret I have is that I didn't start earlier!
I would love to hear about your 'firsts'.

Love is Blind(folded)

The last couple of times Todd and I have been together he has blindfolded me. He then teases me with his cock just barely touching my lips, making me beg to suck it. He has also jacked off and cum on my face when I wasn’t expecting it. To suddenly have hot spunk splashing on you face is quite a sensation.

Linda and I played around with bondage early in our relationship. I tied her up and blindfolded her several times. A few times we reversed roles with her tying me up. Though she loves the dominate role in our relationship, she really didn’t like tying me up. Maybe it was because I was topping from the bottom too much. 

I told her about Todd blindfolding me. She knew I loved it and would relish the role as I am a natural submissive. She even said that she might talk to Todd and offer him some suggestions. I’m not sure what that might entail but I can image it could be quite hot.

I asked her if she had done anything like that with any of the guys she’s been with. She told me that Darryl and she had played around with bondage a few times. Of course he was into spanking so she received several while he had her restrained. But she said that she hadn’t done that with her current boyfriend but might suggest it to him. She even said that it would be interesting if our two guys had us bound at the same time in the same room.

 Oh my!

Gotta love gifts!

Finally getting back to this. As I mentioned in my June 21^st post, I have been seeing Todd regularly for some time now. I don’t date anyone else and neither does he. We see each other almost every week and go out on dates. Of course Linda is very supportive of this and understands my need to see Todd. She is so busy with work demands, traveling so much, that I am often home alone for long stretches of time. Todd fills in those lonely times very nicely.

That being said, there are times that I’m still uneasy at Linda seeing how close Todd and I have become. He and I often kiss each other in front of her and she just smiles as she watches. It’s not every weekend that Todd spends the night with me, but often enough. I feel a bit embarrassed when I come out of my bedroom after being with Todd and have to face her. But she always greets me with “how was your night?”

Todd is so nice to me and showers me with presents constantly. This past weekend he couldn’t see me but sent me flowers and a wrapped present. Linda watched as I opened the box and removed a mint green teddy. It was so pretty (and I bet very expensive!).

“Oh, my sissy husband is getting lingerie from her boyfriend. How nice,” she teased.

What an interesting life I have!

A few of my favorite photos.

I can’t count the number of times I’ve found myself in this position. It’s very humbling to stare into his eyes as you silently beg with yours.













I wish I had these in my wardrobe.

I’ve been on the receiving end of these a few times. Linda is always so nice to share. How about those times when they let you know that you will be the one wearing the condoms from now on… if you ever have the opportunity to use one!