Any Fun Experiences with a Gal helping you into a Dress or Bra

Some of my favotite memories in my 20s was looking bedroom bets to fun Gals and having them put their lingerie and dresses on me !

Of Course they didn't know how much I was enjoying it ! LOL

The smile on their faces as they slid one of their Lacy Bras over my Arms and shoulders and then attached it was always priceless ! And how they would stuff the bra and play with it till it was perfect !

Dress modeling came next ! LOL

I was always attracted to women with lots of meat on their bones so could fit into lots of fun things !

When I was a preteen, the local girl gang used to play a game called catch the boy and put a dress on him. I lost more than any other boy on the block! Lol

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Originally Posted by Karren H

When I was a preteen, the local girl gang used to play a game called catch the boy and put a dress on him. I lost more than any other boy on the block! Lol

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Was it the same Dress everytime ? LOL I do hope it had a big Bow on the Back ! LOL

It was. A very old satin dress that smelled like a grandmother owned it! Lol. It was amazing.

Not until I met my wife and told her about my desires did I ever have any help dressing or doing makeup, since telling her she has done my makeup many of times, when she knows I'm having a rough time and having a hard time letting the guy side relax, she will hand me 2 items, a pair of pantyhose and a gown, I never ask why because I know she knows it relaxes me so I head off to the bathroom, shower and shave(hairy legs and tights gross me out), afterwards we will lay in bed and snuggle. She rubs her legs on mine and rubs my booty to. It's an instant way for her to make me melt and be submissive to what ever she wants,

I bought my first bras at a lingerie specialty shop. The owner showed me several bra styles and made some recommendations. I selected a couple and she put them on me and adjusted the straps and also added some forms to see how they looked. She was very kind and said she had some transgender clients but mostly dealt with Mastectomy clients and special size bras. I learned a lot about bras from her as she took the time to explain the different fits and benefits. A wonderful fun experience.

In my late teens at high school some of the girls dressed me up and paraded me around. I loved it, although would not admit it. Later back in the early 2000s my fiance at the time would dress me up, do my makeup and treat me as a woman. She even initiated these ventures and we both loved it.

Oh and I had another GG friend who would let me send mail order items to her home while I was in the army. Interestingly she came out as gay several years later! I was quite surprised as I thought she was totally straight. She is one amazing woman.

Just helpful SA’s who would zip up that last inch.

Yes, but nothing fetishy to report, Robbie.:sad:

I have a gorgeous GG friend who helps me with Sherry shoots once in awhile. She helps me pick out outfits and sometimes helps me get out of my more difficult silicone prosthesis if I need help.:thumbsup:

I have no interest in her helping me put things on. That would only make a very complicated procedure even more complicated!:doh:
And, sadly I get no thrills from that like u and others here seem to?:o

I had a gf who, in the middle of the action, took off her teddy and put it on me. As much as I liked it, I was too busy to really care. Before we finished she freaked out that I was quite happy in spite of being in it and she took it back off me. This was way before I started dressing in any consistent fashion.

Later she tried to embarrass me by telling a few people about it.

During my late teens to early 20s I dated a girl who used to love to dress me up.

Not to do with CDing but ended up being fun. I complained to my wife that my man boobs hurt after I got done mowing our grass (3 acres of it). She said "You need a bra." Sooo, my niece and I went shopping. Lane Bryant didn't have anything with a small enough cup. They told us to try the ladies wear shop outside the mall. It took us a few minutes to convince the sales lady we were not kidding, that my wife said I should buy a bra for me. Into the fitting room she takes me and measures me up. She goes out and returns with three bras. Two of them felt wonderful and I said I'd take them, without ask how much. $100 later (bought both)we walked out and I was wearing one of them. Had to mow once more (November in upstate NY) just because... The bra worked as planned, love it when a plan comes together.

We went a our support group Christmas party the first year we joined. It was also the end of the first year of my fully coming out to my wife.
We reserved a room in the hotel where the party was being held and dressed there for the event. I had bought a lovely spaghetti strap red floor length gown. After doing my makeup I stepped into the gown and my wife zipped me up. She then did my hair, putting it up for me and inserting rhinestone clips in various places to match my earrings and necklace. She then had me stand and took a few photos before telling me how lovely I looked. I would have cried if I wasn't so afraid of ruining my makeup. I never felt so wonderful, so feminine and so loved.

Like Christie Ann, my only help from a GG has been a helpful SA zipping me up in the dressing room.

I am clearly one of the luckiest guys whose wife helps me get dressed when I need help. Sometimes she helps me even when I don't need help to let me know that she loves me and accepts my need to CD.

One of the things she does anytime I want to spend a day or longer as Teresa, is to help me with my make up. My eye sight is bad enough that I am unable to do my eye lashes and eye liner. Once she does my eyes, I can finish the rest with my glasses on with no problem.

Once I get my wig on, she always takes a final look and usually takes a few strokes with her brush to make it perfect. That is usually the point when I fully realize how wonderful it is to see myself as a women in the mirror, as my wife gives my hair the finishing touches.

Another thing that I totally enjoy is that we most always share our large bathroom mirror and long counter to do our make up at the same time. The fact that we are shoulder to shoulder, both in our panties and bar, adds to my fantasy that we are just two girlfriends getting ready to spend a day together... as two girls.

OMG!!!! Pinch me. This is almost too good to be true... but it is true for this very happy married couple.

In my early teens, before I reached full puberty, I was passable. I had a slightly older female cousin who had found out about my hobby. My cousin had amazing makeup skills and could make me into a believable young teen girl. As far as dressing me, other than suggesting outfit combinations that completed the illusion, my cousin left that part up to me.

The closest that applies to me is going for a bra fitting and the SA helping me into the bras I'm trying on. That's enjoyable.

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Originally Posted by anna kate

Not to do with CDing but ended up being fun. I complained to my wife that my man boobs hurt after I got done mowing our grass (3 acres of it). She said "You need a bra." Sooo, my niece and I went shopping. Lane Bryant didn't have anything with a small enough cup. They told us to try the ladies wear shop outside the mall. It took us a few minutes to convince the sales lady we were not kidding, that my wife said I should buy a bra for me. Into the fitting room she takes me and measures me up. She goes out and returns with three bras. Two of them felt wonderful and I said I'd take them, without ask how much. $100 later (bought both)we walked out and I was wearing one of them. Had to mow once more (November in upstate NY) just because... The bra worked as planned, love it when a plan comes together.

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That's a great idea, combine yard work with crossdressing! My grass would look like a golf coarse.

I've had 2 experiences. First, I went to a boutique to find a long line bra. Owner helped me put on several bras and commented on how they fit. Next was at a second hand store where i tried on a bridal gown. Unfortunatly (?) the back zipper stuck and after a lengthy attempt to get it down, I had to call for the SA for help. After a nice comment on how the gown looked on me, she lowered the zip.

One Time I was shopping for a formal outfit for a special occasion and tried on this back zip off shoulder dress. Well when I tried to take it off I couldn't get it unzipped. I finally went into the little hallway where the dressing rooms were and had to ask another shopper if she could unzip my dress... she was so nice ...

My wife has helped my clothes when I am going out, but never a case where she instigated my dressing.