Jackie Boy

1,668 profile views
5 followers
100 uploads

Heterosexual Cross Dresser


I do like this black chiffon skirt and the way my old wig looks for once
I do like this black chiffon skirt and the way my old wig looks for oncejackieboy
18 3
I think this top is so cute and it hides my Pinot Belly
I think this top is so cute and it hides my Pinot BellyjackieboyModeling
0 0
Pencil Skirt I gave away to Goodwill
Pencil Skirt I gave away to GoodwilljackieboyModeling
8 1
Yeah, I am obviously a Big Beatles Fan, NOT
Yeah, I am obviously a Big Beatles Fan, NOTjackieboyModeling
8 0
Sitting in my favorite Dressing Room at Stein Mart
Sitting in my favorite Dressing Room at Stein MartjackieboyModeling
7 3
The Stein Mart Dressing Room area with its 3 panel mirror is never cowded when I go at lunch time
The Stein Mart Dressing Room area with its 3 panel mirror is never cowded when I go at lunch timejackieboyModeling
4 1
I tried this dress on at Penney’s and it felt so good to wear
I tried this dress on at Penney’s and it felt so good to wearjackieboyModeling
8 1
Another Pants Suit I tried on at Stein Mart. I love this type of collar
Another Pants Suit I tried on at Stein Mart. I love this type of collarjackieboyGlamming Up
2 0
Cute Polka Dot number I hardly ever wear
Cute Polka Dot number I hardly ever wearjackieboyModeling
8 0
Pink
1 5
My favorite dress with my new dangling diamond earrings
My favorite dress with my new dangling diamond earringsjackieboyModeling
6 2
It took me almost a full hour to remove my 7 layers of nail Polish from Sunday’s Manicure
It took me almost a full hour to remove my 7 layers of nail Polish from Sunday’s ManicurejackieboyModeling
2 0
My only long wig
My only long wigjackieboyCasual
2 2
I like this photo beccause my finger nails and toe nails match
I like this photo beccause my finger nails and toe nails matchjackieboyModeling
2 0
Going to Ulta on Wednesday to get my Eyebrows done
Going to Ulta on Wednesday to get my Eyebrows donejackieboyModeling
4 1
The last dress I tried on.
The last dress I tried on.jackieboyModeling
4 0
Posing Examples inspired by my mentor
Posing Examples inspired by my mentorjackieboyOutfit
0 3
Yesterday was Vanna White’s Birthday. She is 63 just like me
Yesterday was Vanna White’s Birthday. She is 63 just like mejackieboyModeling
12 1
Me wearing Anne Klein heels at Stein Mart like my good friend Scarlett
Me wearing Anne Klein heels at Stein Mart like my good friend ScarlettjackieboyModeling
4 0
Brief time today enjoying my other side
Brief time today enjoying my other sidejackieboyModeling
16 2
Thinking about tomorrow’s Gurl Time
Thinking about tomorrow’s Gurl TimejackieboyCasual
2 2
I tried this dress on at Penney’s yesterday and didn’t buy it
I tried this dress on at Penney’s yesterday and didn’t buy itjackieboyGlamming Up
0 0
Skirts I wish I Kept
Skirts I wish I KeptjackieboyCasual
2 0
I tried this skirt and top on at Stein Mart yesterday and loved the look, but didn’t buy it
I tried this skirt and top on at Stein Mart yesterday and loved the look, but didn’t buy itjackieboyCasual
0 0
So I downloaded FaceApp and it is amazing, but completely unrealistic
So I downloaded FaceApp and it is amazing, but completely unrealisticjackieboy
15 3
LBD at Stein Mart with Thong and Thigh Highs
LBD at Stein Mart with Thong and Thigh Highsjackieboy
4 0
I love these new White Short Shorts and this White Top with my Anne Clein Kitten Heels
I love these new White Short Shorts and this White Top with my Anne Clein Kitten HeelsjackieboyModeling
2 0
I love this style of dress, but can’t carry it off
I love this style of dress, but can’t carry it offjackieboyModeling
10 3
I have 2 long gowns, but no place to wear them except around the house
I have 2 long gowns, but no place to wear them except around the housejackieboyModeling
2 0
LBD Thigh Highs and a Thong and Pinot Grigio on the Rocks
LBD Thigh Highs and a Thong and Pinot Grigio on the RocksjackieboyModeling
2 0
The first Maxi Skirt
The first Maxi SkirtjackieboyOut and About
0 0
Lace
LacejackieboyCasual
16 7
Trying a different pose in my new Sweater Dresss
Trying a different pose in my new Sweater DresssjackieboyModeling
4 2
Feeling Pretty in Pink
Feeling Pretty in PinkjackieboyModeling
8 3
Maxi dresses with no panty hose feel so free in the Summer time
Maxi dresses with no panty hose feel so free in the Summer timejackieboyModeling
8 2
My maxi skirts are also great to wear in the Summer
My maxi skirts are also great to wear in the SummerjackieboyModeling
2 3
Can’t wear this to the grocery store
Can’t wear this to the grocery storejackieboyGlamming Up
2 0
Sheer white blouse with dark blue and black Sexy Lace Bra
Sheer white blouse with dark blue and black Sexy Lace BrajackieboyModeling
2 2
One of my new dresses from my Sunday Shopping Spree
One of my new dresses from my Sunday Shopping SpreejackieboyModeling
4 0
Thank God stores are open again
Thank God stores are open againjackieboyModeling
4 1
I didn’t used to like this skirt, but with this blouse I think it works
I didn’t used to like this skirt, but with this blouse I think it worksjackieboyModeling
8 3
I don’t always wear Black
I don’t always wear BlackjackieboyModeling
4 1
I love this lacey top
I love this lacey topjackieboyModeling
2 2
I got a make over at Ulta today it was wondeful
I got a make over at Ulta today it was wondefuljackieboyModeling
8 2
This dress with the bellbottom sleeves makes me happy
This dress with the bellbottom sleeves makes me happyjackieboy
2 0
My new Sweater Dress I got at the Rack today
My new Sweater Dress I got at the Rack todayjackieboyModeling
6 2
I miss shopping at Stein Mart SO MUCH
I miss shopping at Stein Mart SO MUCHjackieboyModeling
2 1
So whle the wife was out partying I had some Gurl time and tried on a bunch of dresses that I haven’t really worn in awhile
So whle the wife was out partying I had some Gurl time and tried on a bunch of dresses that I haven’t really worn in awhilejackieboyModeling
4 0
I love my maxi dress on a hot summer day
I love my maxi dress on a hot summer dayjackieboyModeling
6 2
I love wearing sheer hoisery on freshly shaven legs
I love wearing sheer hoisery on freshly shaven legsjackieboyModeling
20 1
One of the few dresses I can wear of my wife. The slit sleeves make me feel very sexy
One of the few dresses I can wear of my wife. The slit sleeves make me feel very sexyjackieboyGlamming Up
4 3
Still my favorite dress of all time
Still my favorite dress of all timejackieboyModeling
4 0
A look of Consternation as another woman steps out of the dressing room to look in the three panel mirror
A look of Consternation as another woman steps out of the dressing room to look in the three panel mirrorjackieboyMakeup
6 1
My New Jean Jacket with my new maxi skirt
My New Jean Jacket with my new maxi skirtjackieboyCasual
2 0
Brrr. It is cold today.
Brrr. It is cold today.jackieboyModeling
6 3
Feeling Pretty in Pink
Feeling Pretty in PinkjackieboyModeling
2 0
Another Spring Style Dress. I love the Pink stripe at the bottom
Another Spring Style Dress. I love the Pink stripe at the bottomjackieboyModeling
6 2
I liked this dress at Stein Mart, but didn’t buy it
I liked this dress at Stein Mart, but didn’t buy itjackieboyModeling
6 1
This is what I wish I wore out shopping today.
This is what I wish I wore out shopping today.jackieboyMakeup
0 0
Skater Skirts and Tights and with a Black Turtleneck are so cozy to wear while shopping.
Skater Skirts and Tights and with a Black Turtleneck are so cozy to wear while shopping.jackieboyModeling
2 0
This is the dress I bought today at Burlington Coat Factory
This is the dress I bought today at Burlington Coat FactoryjackieboyModeling
4 0
This is what I wore shopping yesterday
This is what I wore shopping yesterdayjackieboyModeling
2 0
LBD, going through old photos
LBD, going through old photosjackieboyModeling
10 0
I do love the fuzzy warmth of this Cowl Necked Sweater
I do love the fuzzy warmth of this Cowl Necked SweaterjackieboyModeling
8 0
This dress was fun to try on, but too boxy. I should have gone and tried on a Large instead of this XL
This dress was fun to try on, but too boxy. I should have gone and tried on a Large instead of this XLjackieboyModeling
2 0
Oh No, this one again!!!!
Oh No, this one again!!!!jackieboyModeling
14 1
I Finally found a bottom to wear with this Top
I Finally found a bottom to wear with this TopjackieboyCasual
4 2
All Business
All BusinessjackieboyOut and About
2 1
Since my wife was out of town I got to walk the dog in her Mink and Mink Ear Wrap
Since my wife was out of town I got to walk the dog in her Mink and Mink Ear WrapjackieboyModeling
10 2
I just finished reading “A Woman’s Passion” written by a CDH member Cheryl Ann (Cassie) Sanders
I just finished reading “A Woman’s Passion” written by a CDH member Cheryl Ann (Cassie) SandersjackieboyOut and About
8 1
I tried on this Glittery Gown at Penney’s today
I tried on this Glittery Gown at Penney’s todayjackieboy
8 0
I also miss shopping at Nordstrom’s Rack
I also miss shopping at Nordstrom’s RackjackieboyModeling
10 1
This was fun to try on, but where would I wear it?
This was fun to try on, but where would I wear it?jackieboyModeling
0 0
Last week I asked CDH members to suggest a blouse I could wear with my black chiffon skirt
Last week I asked CDH members to suggest a blouse I could wear with my black chiffon skirtjackieboyModeling
2 1
The wife is going to Mexico for a week
The wife is going to Mexico for a weekjackieboyModeling
14 0
I never buy casual clothes and I don’t know why.
I never buy casual clothes and I don’t know why.jackieboy
2 0
My favorite every day dress with no hosiery and tan legs
My favorite every day dress with no hosiery and tan legsjackieboyModeling
2 2
I got a make over at Ulta today
I got a make over at Ulta todayjackieboyMakeup
8 0
Stein Mart had a Rack full of LBDs on Saturday
Stein Mart had a Rack full of LBDs on SaturdayjackieboyGlamming Up
0 0
She’s got Legs
She’s got LegsjackieboyModeling
8 0
This is the dress I bought at Stein Mart today
This is the dress I bought at Stein Mart todayjackieboyCasual
10 1
This one was a good contender, but didn’t make the final cut
This one was a good contender, but didn’t make the final cutjackieboyGlamming Up
4 0
I went shopping yesterday and all of the dressing rooms were locked down due to Covid 19
I went shopping yesterday and all of the dressing rooms were locked down due to Covid 19jackieboyModeling
4 0
I spilt fingernail glue on this dress and had to toss it. What a waste
I spilt fingernail glue on this dress and had to toss it. What a wastejackieboyModeling
8 3
I tried on this LBD but I think I already have 6
I tried on this LBD but I think I already have 6jackieboyModeling
4 0
Lace makes me feel so feminine
Lace makes me feel so femininejackieboyModeling
4 0
So it was a shopping day and before I went out I stopped by the Chat Room
So it was a shopping day and before I went out I stopped by the Chat RoomjackieboyGlamming Up
5 3
My Favorite Summer Dress with no Pantyhose
My Favorite Summer Dress with no PantyhosejackieboyModeling
4 0
Another LBD that I liked, but not enough to buy
Another LBD that I liked, but not enough to buyjackieboy
1 0
My Favorite Booties
My Favorite BootiesjackieboyModeling
2 0
Burlington Coat Factory Dress
Burlington Coat Factory DressjackieboyCasual
0 2
My first Dress I ever bought with a Zipper. They may be difficult but they are worth the trouble
My first Dress I ever bought with a Zipper. They may be difficult but they are worth the troublejackieboyModeling
0 1
This Spring I will lose 20 lbs and wear this dress in public
This Spring I will lose 20 lbs and wear this dress in publicjackieboyModeling
5 3
Someone drank too much wine last night
Someone drank too much wine last nightjackieboyGlamming Up
0 3
Shopping at Stein Mart with my new Strapless Bra and trying on clothes that would show off my Cleavage
Shopping at Stein Mart with my new Strapless Bra and trying on clothes that would show off my CleavagejackieboyModeling
0 0
My first dress I ever bought with a zipper
My first dress I ever bought with a zipperjackieboyModeling
2 0
I don’t understand why something so innocuous as a Purse makes me happy
I don’t understand why something so innocuous as a Purse makes me happyjackieboyModeling
8 1
Another rather Bold Look for me
Another rather Bold Look for mejackieboyModeling
8 2
I would never wear a dress like this in public, but it was fun to try on
I would never wear a dress like this in public, but it was fun to try onjackieboyModeling
4 1
Sheer pantyhose on freshly shaven legs
Sheer pantyhose on freshly shaven legsjackieboyGlamming Up
0 0
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

or    

Forgot your details?

Create Account