Crossdressing Stories

Girlfriend wants Boyfriend to Crossdress

girlfriend wants boyfriend to crossdress

It were a walk home on a Saturday night, after we had been to the Club, to play Bingo and afterward, listen to a live show there. Gloria’s home, were through the woods, which had a tarmac path.

I began the conversation, by telling her, “After we marry, you can give up working, if I make sufficient money to keep us both.”

Gloria: Why should I give up my job,she snapped, I like my job.

Graham: Well to stay at home to cook and clean, I explaining.

Gloria: Oh I can’t cook and hate housework, her again her tone were not quiet.

Graham: Well I can cook and I have done housework, for my mom.

Silence as we walked that late autumnal evening, among the trees. Then feeling her contemplating, she came out with the answer.

Gloria: I know, if you can cook and like housework, I go out to work and you stay at home, to do these jobs.

Graham: Oh you would like that, you wearing the trousers, I now putting, it that it be me the man, not her.

Gloria now on fire, “YES, and you would look good in a pinafore.”, she laughed and run ahead of me.

Graham:  I suppose you would have me wearing knickers as well.

Gloria, stopped suddenly, thought and saying, yes, that be a good idea. We then carried on walking, and dropped the subject.

A few weeks past and we again now walking a lane, but not the path, and we stopped, to kiss. It were now a chilly night, with a full moon.

Graham: Are you not cold ?

Gloria: Cold, no, why do you ask?

Graham: Well you wearing a skirt.

Gloria: Graham, a skirt can be as warm as trousers, if not warmer with some skirts.

Graham: Well I wouldn’t know, as I have never worn a skirt.

Gloria: Well you can wear this one, when we arrive at my home.

Graham: Well that be no trial, just the skirt and indoors, me telling her.

Gloria: Well go up around the garden, no one will see you, as it being dark.

Graham: Yes, but I will have only your skirt on and it still not be the right test.


Gloria: Well I tell you what, you can wear all the clothes that I am wearing now.

Graham: All?

Gloria: Yes, everything.

Graham: Even your knickers?

Gloria: Yes, even my knickers.

Graham: Oh Gloria, I am afraid.

Gloria: Afraid of what, her asking?

Graham: What if I like wearing your clothes?

Gloria:Well, you can wear them all the time, you come up to see me. But your mom, be there. What will your mom say about it?

Graham: You best tell her Gloria.

Gloria: No Graham, you will tell my mom.

Graham: Oh gosh, what do I say to her?

Gloria: Tell her, you like wearing women’s clothes.

Graham: What will your mom say?

Gloria: Mom will probably advocate it, and take you to buy some of your own, so you not wear mine anymore.

Graham: Can’t your mom and you go for me?

Gloria: No Graham, it be with my mom, or the three of us go, as you will be needed to be measured.

Graham: measured for what?

Gloria: Well your dress size, your women’s shoe size, your bra size.

Graham: Bra? I’m not wearing a bra Gloria.

Gloria: You will have to, or your bust be flat, and people will notice it.

Graham: People? I will not be going out in public, dressed as a woman.

We’ll see, her now seeming to be enjoying this, and the knowing my feminization will soon begin, in readiness for our marriage and me the stay at home housewife. Little were I aware of it all, but Gloria, and her mom Hilda, were very serious about it all, that it be me wearing the skirt and in the petticoats, after the marriage.

Next time, Graham takes new vows, in Gloria’s wedding bridal gown even wearing the lingerie she wore on our wedding day. ~~

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