Planning on doing some crossdress self-bondage sessions (18+)

[illest]

So there were intolerable circumstances involved where I left my job. This has left me job searching but also with a lot of free time and needing to de-stress. However I've been getting cold feet due to not dressing up in a while. However being given instructions on how to dress really gets the mind racing.

So I'm thinking leaving it up to y'all guys how I dress(and possibly how I'm bound) might be fun. I'm going to list my current inventory and let you guys throw out requests and combinations if possible.

Attires:

Black Maid outfit
Pink Cheerleader "Sissy" dress
Black and pink lingerie
Pantyhose
Fishnet stockings
Blue secretary blouse
White crop top
White tube top
Black Skater Skirt
Pink Skater Skirt
Plaid Schoolgirl Mini Skirt
Plaid Schoolgirl suspender skirt
1950s Red Polka Dot Dress
Big Red Bow headband
Pink Headband
Black Latex Minidress
Black Latex Microskirt
Pink Leotard
Blue and white Schoolgirl Onesie outfit
Red super tight dress(I accidentally ordered a amall but I can squeeze in it)
White bodycon dress
Pink bunny ear headband
Pink and black collar with "SLUT" in small gold letters
White collar with "BRAT" written in gold letters
Black denim short dress
White pumps
Black and red 6' stiletto heels
Black High Heel boots
Bright pink strap-on heels

Various types of undergarments and other stuff I can't think of. Also open to suggestions not listed. If I don't own outright I may order eventually once I get a steady income back in or in the last ditch event I have to touch my 401K.

[illest]

Wigs:

Short Blonde Wig
Short Black Wig
Black Honeycomb wig
Blonde Schoolgirl Pigtails
Long Black Wig
Other wigs I can't describe well

Bonds:

Black rope
White rope
Red rope
Gray Duct tape
Ace Bandages
Vet wrap(low on supply)

Gags:

Black 2' Ballgag
Pump gag
Red "training" harness with red lips
Ace Bandage
Vet Wrap
Pink thigh high socks
Black thigh high socks
Various types of panties and thongs(also add to aforementioned to attire)
Standard socks
Harness Ring Gag

Other items:

Wand
Leash
Corsets

I tend to enjoy hogties, but I also enjoy wedgies as well. As far as gags go I'm really flexible as gags are possibly my favorite part of bondage. I can take pretty big gags but don't go too crazy . If I see an idea that piques my interest and I decide to replicate it, I will probably film it like my other recent sessions and put it on DA. Because of this and other personal reasons, no nude suggestions. I can go risque but when I dress up, I like to look as close to geniune as possible, both for my personal preferences and in the 1/10000000 chance that someone who knows me stumbles upon my DA profile they won't easily recognize me(hopefully).

[Estherthedresser]

Lingerie of your choice.
Red polka dot dress
Pantyhose
White pumps

Black short wig

White rope hogtie.

For the head I'm going s little off menue:
A white cloth cleave gag with optional stuffing of panties, and a white cloth blindfold.
If off menue is out of the question then bandages over mouth and eyes with a stuffing of panties.

[illest]

Lingerie of your choice.
Red polka dot dress
Pantyhose
White pumps

Black short wig

White rope hogtie.

For the head I'm going s little off menue:
A white cloth cleave gag with optional stuffing of panties, and a white cloth blindfold.
If off menue is out of the question then bandages over mouth and eyes with a stuffing of panties.

I like those options, I mean REALLY like those options!! I think that's actually going to be my session for today. Only two things I may have to alter is that they may have to be bandages as far as the gag and blindfold goes. I have some hankerchiefs that I bought but I can't remember whether they were long enough to use as a cleave gag(though if I have enough I can wing it). I'm going to check and see if my short black wig is in good condition to wear today. I noticed some of my wigs were rather scraggly so I bought some wig shampoo(don't know what I'm doing with it ) but can't remember if that one was among the ones I need to tend to. I've dabbled in crossdressing here and there but only recently have I went "all out" with it. I know the collection says otherwise but once my wife was okay with it I went kinda crazy in buying stuff last year

[Estherthedresser]

Great to hear that you like my picks! It's a bit of an old fashioned combination but I love old fashioned, at least when it comes to crossdressing and bondage.
I hope you have fun and please let us know how it went.

[illest]

Great to hear that you like my picks! It's a bit of an old fashioned combination but I love old fashioned, at least when it comes to crossdressing and bondage.
I hope you have fun and please let us know how it went.

It was so fun!! I will say that most of my wigs were in dire need of washing and I had to throw out a couple(including the short wig). Went with this short blonde wig that I had actually bought to go with that dress. Also had to use ace wraps for the gag and blindfold. As far as the gag goes I actually used TWO pairs of panties! My checks were bulging, and much to my surprise once I gagged myself I wore it through the whole session. But gracious my jaw felt it when I took the gag off!

I did a bunch of screenshots, including some selfies beforehand, gagged selfie w/o blindfold, sitting on floor with arms behind back gagged(kinda faked that ), the hogtie with and without blindfold(not faked), and finally a chair tie with wand(faked due to making the cinch noose too short to stretch to my wrists ) The ones where I was tied I did a video and am basically taking screenshots from said video.

Probably about to PM you with a link to DA showing my pics, which I plan om doing in story, so first part is just me glammed up wearing the outfit

[Estherthedresser]

Glad you enjoyed yourself! How long did you stay tied up? I'm curious about the pics.

[illest]

Glad you enjoyed yourself! How long did you stay tied up? I'm curious about the pics.

Roughly about 10 minutes max. Had some stuff to do and wanted to clean up before the Mrs. returned. However she's planning a girls' getaway soon. Provided I'm still a house husband around that time I'll have some considerate free time to do some really fun scenarios(including a couple with the closet bar ). Also I just posted the beginning gag pics on DA. Probably will post Part 3(hogtie) either later today or tomorrow.