Diana Mac Donald

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I have a feminine side that I enjoy embracing. The girl expressed herself in my adolescence for a brief period. This culminated in an episode in which I fully dressed in my mother’s clothing with makeup and a wig. After this event, she disappeared for years.
The woman came back much stronger after my fiancé broke off our engagement. I was deployed with the Army in Bosnia and never saw Amy again. I went back to my home base in Germany just long enough to change my duty assignment to Washington DC. Now the woman was back. But she only dabbled in a little makeup here and there.
However, once in DC, she started to gather clothing and other items. She also found Mistress Brianna and made plans to meet with her.
The pivotal night arrived and I drove to Mistress Brianna’s house. We sat down and Diana introduced herself and told Mistress that she wanted to be completely made up as a woman and taken as one. She has never left me since. Even though I went through several purges (damn, I lost some awesome items and pictures) Diana has been a part of me since that first time with Mistress Brianna.
Diana was suppressed for a bit of time when I got married. She came out to my ex before the wedding. Karin went through with the ceremony anyways. Diana spent an evening with her shortly after. The next day Karin demanded that Diana would never come out again. And naively Diana was told that she would have to leave.
That did not happen. In a few years I was in the same situation many of my sisters are in. That is hiding my feminine side from the one I love and Diana came out a few times.
It wasn’t until after the divorce that I fully accepted Diana as me. I made plans for Diana to spend a week in Las Vegas. However, I was frightened that I would not have the courage to go out on my own. That is where Chrissie comes into the picture. I met here a few months before the fateful quest. I got to know her and found out that she had some TG friends. I took the leap and revealed Diana to her. Chrissie accepted Diana who eventually asked her to join her on the Vegas trip. Chrissie went and I, Diana, spent the entire week as me!! Diana had her true “coming out.” Since then I have been out several times with my girlfriend and our friends.


Feeling Very Pretty
Feeling Very Prettydianacd22Casual
8 5
Lunch Date
Lunch Datedianacd22Outfit
14 7
Going Out for the Evening
Going Out for the Eveningdianacd22Party Time
14 8
A WHOLE WEEK, Day 7!
A WHOLE WEEK, Day 7!dianacd22Out and About
1 7
A WHOLE WEEK, Day 7!
A WHOLE WEEK, Day 7!dianacd22Outfit
3 7
Independence Day Weekend!
Independence Day Weekend!dianacd22Out and About
6 9
Independence Day Weekend!
Independence Day Weekend!dianacd22Makeup
6 5
Independence Day Weekend!
Independence Day Weekend!dianacd22Swimsuit
3 10
Holiday Cheer
Holiday Cheerdianacd22Party Time
1 3
Independence Day Weekend!
Independence Day Weekend!dianacd22Swimsuit
0 4
Holiday Cheer
Holiday Cheerdianacd22Party Time
3 5
Holiday Cheer
Holiday Cheerdianacd22Party Time
1 4
Belt or No Belt?
Belt or No Belt?dianacd22Accessories
4 4
Spreading Some Christmas Cheer
Spreading Some Christmas Cheerdianacd22Events
9 4
Spreading Some Christmas Cheer
Spreading Some Christmas Cheerdianacd22Events
7 5
Spreading Some Christmas Cheer
Spreading Some Christmas Cheerdianacd22Outfit
8 5
May I Help You
May I Help Youdianacd22Casual
2 6
A day at the house
A day at the housedianacd22Casual
9 13
Legs and Heels
Legs and Heelsdianacd22Shoes
13 6
Legs and Heels
Legs and Heelsdianacd22
6 4
Second Day in Vegas
Second Day in Vegasdianacd22Modeling/Posing
9 11
Feeling Pretty
Feeling Prettydianacd22Makeup
2 5
Las Vega First Day
Las Vega First Daydianacd22
9 11
Meet a New Friend
Meet a New Frienddianacd22Out and About
18 7
Evening in Las Vegas
Evening in Las Vegasdianacd22Out and About
10 7
“Fancy Like” on Day 6
“Fancy Like” on Day 6dianacd22Glamming Up
11 20
Sexy Sweater Dress
Sexy Sweater Dressdianacd22Modeling/Posing
5 5
Evening in Las Vegas
Evening in Las Vegasdianacd22Out and About
5 5
Ready to Meet a Friend
Ready to Meet a Frienddianacd22Outfit
15 8
My First Professional Manicure EVER!!
My First Professional Manicure EVER!!dianacd22Glamming Up
5 6
Party Time
Party Timedianacd22Party Time
9 5
Ready for the Night
Ready for the Nightdianacd22Out and About
3 7
Party Time
Party Timedianacd22Party Time
9 3
Ready for the Night
Ready for the Nightdianacd22Out and About
2 8
Finally I had another manicure!
Finally I had another manicure!dianacd22Outfit
5 3
Enjoying Being Me
Enjoying Being Medianacd22Casual
2 6
Lipstick and Masc
Lipstick and Mascdianacd22Casual
1 3
Ready to be the Hostess
Ready to be the Hostessdianacd22Party Time
1 5
Ready to be the Hostess
Ready to be the Hostessdianacd22Party Time
4 6
Lipstick and Mascara
Lipstick and Mascaradianacd22Casual
4 2
Ready to be the Hostess
Ready to be the Hostessdianacd22Party Time
4 7
Lipstick and Mascara
Lipstick and Mascaradianacd22Casual
2 5
Casual Afternoon
Casual Afternoondianacd22Casual
12 6
Casual Afternoon
Casual Afternoondianacd22Casual
7 2
Mystere on Day 4
Mystere on Day 4dianacd22Outfit
6 9
Casual Afternoon
Casual Afternoondianacd22Casual
4 3
The Evening on Day 4
The Evening on Day 4dianacd22Out and About
2 4
Casual on Day 5
Casual on Day 5dianacd22Casual
3 6
Looking pretty on Day 5
Looking pretty on Day 5dianacd22Makeup
4 4
Farewell to Kimmie
Farewell to Kimmiedianacd22Outfit
5 5
Farewell to Kimmie
Farewell to Kimmiedianacd22Out and About
12 4
Hot Tub Fun
Hot Tub Fundianacd22Swimsuit
6 3
Second Day in Vegas
Second Day in Vegasdianacd22Casual
1 6
Second Day in Vegas
Second Day in Vegasdianacd22Out and About
4 9
Second Night in Vegas
Second Night in Vegasdianacd22Glamming Up
6 9
Playful on the 3rd Day.
Playful on the 3rd Day.dianacd22Outfit
4 11
Second Day in Vegas
Second Day in Vegasdianacd22Casual
7 8
New Wardrobe
New Wardrobedianacd22Outfit
7 10
Second Day in Vegas
Second Day in Vegasdianacd22Casual
2 8
Playful on the 3rd Day.
Playful on the 3rd Day.dianacd22Makeup
3 6
New Years Eve
New Years Evedianacd22Party Time
0 1
Playful on the 3rd Day.
Playful on the 3rd Day.dianacd22Out and About
2 11
New Years Eve
New Years Evedianacd22Party Time
7 5
Playful on the 3rd Day.
Playful on the 3rd Day.dianacd22Out and About
2 7
Enjoying a Beautiful New Year’s Day
Enjoying a Beautiful New Year’s Daydianacd22Casual
7 8
New Year’s Eve Party
New Year’s Eve Partydianacd22Party Time
12 5
New Year’s Eve Party
New Year’s Eve Partydianacd22Party Time
11 5
New Year’s Eve Party
New Year’s Eve Partydianacd22Party Time
7 4
Another Night (the 5th) Out,
Another Night (the 5th) Out,dianacd22Modeling/Posing
9 10
“Fancy Like” on Day 6
“Fancy Like” on Day 6dianacd22Glamming Up
19 20
Lady in Red
Lady in Reddianacd22Party Time
35 24
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