Crossdressing Stories


Crossdressing Story

I always looked forward to a Friday night, as it was Bingo and afterward a chat, around the table. I used to collect three women, from nearby, Kathy, Heidi and Alison. We all sat together, but we did not pool our winnings, if any of us won.

Well this week, I won the Snowball, which were £200.00. So my platonic three girlfriends, I thought of them as, looked at me, as I counted the cash out, on the table, then handed each £50.00.

“What’s that for? ” all three of them simultaneously chorused.

Graham: For you, to enjoy.

“Graham, our understanding was not to pool our winnings”, spoke Heidi and the other two also agreed.

Graham: Yes, I am aware of it, but I am sharing it between us four, so take it and enjoy, buy yourself something nice, then add a pair of pretty French knickers.

The three laughed.

“Thank you, Graham, you’re very kind.”, said Heidi, the other two agreeing.

“I am going for a slash, anyone coming”, says Kathy.

“For shame”, came Heidi,”and in front of Graham”.

Kathy, commenting, “oh don’t be silly Heidi, we consider Graham, as one of us.”.

Heidi rose from her chair, and said, ” I’ll come with you, referring to the ladies bathroom. Once both left, Alison thanked me for my beneficence, and asked why Kathy had said, we consider Graham, as one of us.

Graham: Oh Kathy, means, that we four are always together.

Alison : Or does she mean that you are a woman? and why say, for us to buy french knickers? Can I ask you something Graham, before they return.

Graham: Of course Alison.

Alison : There is a church wedding tomorrow morning, at our church. I would like to go and see them all exit, for the photos and to see what the women are wearing, would you please accompany me. It’s 11:30; and I would very much appreciate it, if you were there.

Graham: Yes, Alison, I shall pick you up, and we go together.

Alison : Thank you Graham.

Kathy and Heidi returned, we ended our chat and left the club. I dropped Heidi off first, then Kathy, then took Alison to her home. Alison, turned to me and kissed me on the cheek, thanking me and seeing you tomorrow.

Saturday morning was a hot and sunny day, as I stopped to wait for Alison. Here she comes, out, dressed in a red sundress.

Graham: My gosh, you look wonderful Alison, in your dress, but myself, I would not wear a red dress, but I would wear blue or a white today. Yet, red suits you.

It was not far and only took us less than ten minutes. We parked up and entered the church, then afterward, stood back by the yew trees, to watch all the photographs, being taken. Alison, commenting on the brides, bridal gown, the bridesmaids, and the women of groom and brides outfit.

Alison :  which color dress, for the bridesmaids, would you have chosen? I am sure, this is not the first wedding you have witnessed Graham.

Graham: I do like the cerise dresses, but the last wedding, the bridesmaids, were in lilac.  I do like lilac as a pastel shade and continue to describe the dresses I have seen with bridesmaids, at weddings.

Alison : You are into this Graham. I am so glad I asked you now, to accompany me.

Graham: Thank you Alison.

Alison : Will you be honest with me Graham, if I ask you some questions.

Graham: Of course Alison, I never lie to a woman, that is lethal. Look, let’s go and have a drink and you can ask all you wish, I shall drink soda water, as I am driving, and if you like, we can take lunch there, I know a country pub.

Well, off we went, then sat outside near a fountain and shade. We ate a hearty meal and then I asked Alison, what questions she liked to ask me.

Alison : Well Graham, thank you for everything today, I have not only enjoyed it, but also your company. You really are good to women.

Graham: Well Alison, go ahead and thank you.

Alison : Mm, how can I put this to you..

Graham: Alison, please.

Alison : Well, do you dress up, came her first question.

Graham: Dress-up?

Alison : Yes, dress up in women’s clothes?

Graham: Why ask that, Alison.

Alison : Well sweetie, you are very well versed in ladies wear. Whatever you say, Graham, is safe with me.

Graham: Yes, Alison, I do dress up and wear around the house.

Alison : You mean, when you are on your own there, as you live with your mom and two sisters?

Graham: Alison, I have been dressing up, well since my primary school days, into my teenage years and to now. I have worn my sisters hand-me-downs, to save my boys clothes, as mom, could not afford much for us all, but we had a roof over our head and food in our belly. We were and still are happy.

Alison (intrigued) :Are you wearing knickers now?

Graham: Yes and with a nod.

Alison : May I ask, what colour?

Graham: A rose pink, and they are full sided knickers, not these teeny kinds.

Alison : Can I see them?

Graham: Not here, but we can go to a secluded place and I, show you.

I paid the bill, and I drove to a forest.

Alison : No, not in the car, let’s get out.

We walked to a spot, where I dropped my beige trousers. Alison looked, then told me to strip off, bar my knickers. I  now seemed under her spell or a domineering command. Alison had me turn around and then turn back to face her. I did so, and she stood in her white knickers and shoes.

Alison : We seem to be the same dress size, so I would like you to put my dress on, to see if red does become you.

I did as asked, and gave a twirl, which excited her.Now Alison donned my shirt and trousers and we walked a while, deeper into the woodland.

Alison : How do you feel Graham?

Graham: Oh gosh Alison, it’s wonderful.

I thanked her, and added I needed to pee.

Graham: Well Jane, don’t be shy, we’re both girls, squat here, lift your dress, pull your knickers down and pee sweetie.

I did so, just like a girl would.

Alison : Feeling better now babes, her asking?

Graham: Oh yes. Do you need to pee Alison?

Alison : Not now sweetie, but you will see me pee, when you come to my home, for Sunday lunch. My mom and dad have gone to the coast, to their caravan, so we are together, as girls.

Graham: You mean, you are having me dress up, in your clothes.

Alison : Oh yes my little maiden friend. You shall try on many of my dresses and other items from my wardrobe and drawers. Let’s return to the car, her commanding.

Graham: Shall we change back here, asking her?

Alison : Oh no baby, in the car.

Little were I to know, we would become more than good friends at the BINGO.


Submitted by Graham Jones

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