The best offer from a GG you declined

[heathr1]

What was it?

In my teens, mom found my skirts in my room and sympathetically asked me about them, offering support and promising not to tell a soul.

I was too embarrassed to talk to her and to this day she has kept her promise.

[Beverley Sims]

I was Nineteen at the time and dressing regularly.

I was offered a holiday staying at the family beach house for a week dressed, with with just this girl and I.

Instead I accepted a similar holiday at another beach house dressed with my three housemates and two other friends.

The next day the "other" girl fronted up and there were seven of us.

Ask me? do I remember it? :)

[Nikki A.]

I dated this one lady who knew about me dressing for Halloween from her friends. She asked if I was a CD & I said no. Shes pretty open minded and I wonder how things would have gone if I said yes.

[sandra-leigh]

One evening while i was at a club (dressed), chatting with a woman I've met a few times before, a co-worker of hers came by and joined the conversation... and was thrilled with my dressing. She wanted me to visit her the next day, get me prepared, go to some kind of new-age revivalist church with her (it wasn't Unitarian Universalist, which I at least know a bit about.) She wasn't just offering for that one next day, it was more implied to be over an indefinite period and "We'll have so much fun". Unstated but under-toned was a sexual relationship (the woman I was talking to first also picked up on that). The co-worker wasn't stopping and asking me what I would like to do, just streaming out the plans. Oh wait, I just remembered that the co-worker was also the room-mate of the woman I knew.

After a bit, the co-worker left to go to the washroom, telling me to wait. I excused myself to the woman I was talking to, mentioned that I am already in a relationship, asked her to make my apologies for me, and took my leave. The woman understood completely. As I left, I felt like I had escaped...

[KimberlyJean]

I have an ex-girlfriend that offered a couple of opportunities that I didn't know how to react to so I declined. Right before we broke up she was wearing a black bra and panty set with a choker necklace. I won't get into how but I ended up wearing them before we were done and that memory stands out in my mind.

[Jenni Yumiko]

Threesome with my ex and my other ex. The ex that I still talk to and hang out with regularly won't let me forget it. Of course the offer is no longer on the table. :-(

[leonal123]

I had this classmate who once came to my apt to do an assignment together in grad school. She saw a pairs of heels under my bed which I wore night before. She wanted to talk abuot it but I said its from the girl Im dating. She knew that I was single though..

[CDChloe1972]

I went to a party one of the very few times I was dressed in public and there was this gorl there who leant me her satin elbow length gloves. I love these types of gloves by the way and I own several.

It came time for her to leave so she sat down and joked with me that she had to take the gloves back. She was very sweet and she new that I had rfeally enjoyed wearing them. There was a lingering tension between us, I guess the proposition about whether we were going to ask each other home or if we were going to exchange phone numbers lingered for a long time. I was too nervous and didn't say anything. Oh well....... C'est La Vie

[Paula_56]

When I was in the USAF I was friends with a gay woman, to the point that everyone thought we were dating. We had this weird crush going for each other. I had so many opportunities to open up about being trans but didn't. She use to go to drag shows with her GF and always wanted me to go too. Once she said, "I have a feelng down down you would like doing drag" Oh sweet heart you were so right.

[Cheryl T]

I was probably 11 or so and my aunt caught me in her things and she offered to dress me anytime I wanted. Of course I was too scared and never did accept her offer...something I will always regret.

[Julogden]

I must have been about 11 or so. At that time, I was the same size as my mom, and she wanted to really dress me up properly as a girl for Halloween, telling me that when she was done with me, no one would suspect that I was a boy. I was secretly ecstatic, and was eagerly going along with her plan until she started talking about shaping my eyebrows into very slender girl-brows. For some reason, that scared me off and it never happened. I'll always regret that.

Carol

[lingerieLiz]

I was just starting to bye nice lingerie years ago and the girl my age in the lingerie shop said "everyone should enjoy wearing nice lingerie" in a way that she let me know she knew it was for me. Guess because I told her my aunt was about my size. She then hinted it was about closing time and it was a nice night out.

Had a girl friend who would have been accepting, but I could never tell her. Did tell my wife before we married though.

[sometimes_miss]

When I was 27, one of the hottest girls I ever knew was throwing herself at me, yet I was dating someone else and loyally stayed with her instead of going off with the hottie. Said girlfriend later dumped me anyway, and I had neither, since I had set up the hottie with her future husband. In retrospect, sure, it seemed the right thing to do, but basically I had just screwed myself out of perhaps the best opportunity of my life.

[Cheryl Ann Owens]

I just remembered a situation from my junior year in high school. I was dating a very hot gal who said she loved my blue eyes. She was very good with her own makeup I might add. Now remember, this was also a trying time for me because I wanted to be one of the girls but back in 1970, well, many of you know the culture back then. I dated her for the affection I received and while it felt right, I still felt different wanting to be a girl.

One day we were at a mall and before going in she and I were sitting and talking. She may have detected something? Because she said to me something like, "You have pretty blue eyes. I'd love to make them up." "Stooopid" here gushed and said he couldn't do it. Talk about regret! I would have loved it!

Cheryl Ann

[gender_blender]

I took every offer from GGs related to crossdressing growing up. From honest answers and Trying stuff on to full makeovers and other experiences. No regrets!

[Sharon B.]

In my late thirties after my divorce I was dating a woman and she kept asking me if I wanted to talk about why I enjoy dressing as a woman. I never did talk with her about it, wish I would have I have regretted to this day. I did tell her early into the dating scene but we were only good friends back then and I have lost track of her since. Just wonder what would have happen if I had open up to her.

[Kate Simmons]

I've never declined a good offer from any woman, or anyone else either. ;):battingeyelashes::)

[I Am Paula]

Well, there was this stripper in ....

[BlairP]

When I was 10, I had long blonde thick hair and my cousin told me I looked like a girl. She wanted to dress me up and send me to the corner burger stand to me a boy.

[dominique]

well it was the time when my wife found out that i was dressing. during the talk she asked me if i still waned to dress and I said no. i wonder what if i had said yes. regrets yes.

[NV Susan]

When I was 19 I was dating a girl who knew of my CD'ing. She would let me dress when we spent the day at her place {we could even wear the same size skirts, dresses & tops}. Well one day she offers to do my make up and go to dinner as girlfriends!! Oh I said YES...it went great....and we would after that have boy-girl dates, or girl-girl dates....

Sorry just noticed this was to be about offers declined......silly me!! :doh: