When Dressed I Become A Woman

From the moment I put the bra on I feel like a woman. When dressed I become a woman 100% I walk differently, I talk differently, I think and have urges like a woman. As Jessica I am attracted to men. If I am as a man, I have NO interest in men
The first time a man took me home to his place. We had drinks and wound up in bed. After a few hours of play. He had been satisfied by and hour of awesome sex in all positions! He started to pleasure me orally. I lay there in a lace bra, garters and stockings. I was in heaven feeling all sexy and girly. He licked my **** and talked dirty to me. Needless to say as I squeezed my own breasts he brought me to climax. I came with about 5 bursts. Pure ecstasy.
Then BOOM I'm a MAN again. It was an unexpected feeling of disgust for what I had just done. I enjoyed the hell out of it, but I was ashamed, and now a man in womans clothes.
Now I had to go around and pick up my heels, skirt, blouse, jewelry, purse and go fix my makeup, hair and dress back as a woman to go home. I was totally freaked out!
I was as nice to the guy as I could be. I said goodby and walked out to my car for the drive home. When I had to re-dress as a woman. It was like forced feminization. I have come to enjoy that part as well.
ka851 ka851
51-55, T
10 Responses Dec 2, 2012

I used to go through the same thing but i got over it by driving a long way frm home mastering to completion then having to drive back by the time i was home i was over the guilt and ready to continue the night

Judging from the other comments and my own experience , it must be more common than not to feel ashamed after sex with another man . But the compulsion to do it is so strong the after-shame recedes as the desire returns over a few days . My problem is ,I think ,another one common to 'sissy' psychology - namely there just doesn't seem to as many men available of the type I want - dominant , controlling , masculine types who could take me and **** me . We yearning-to-be-attractive-as-females sissies are abundant , and the right sort of man too few . The best we can manage is to give oral sex - there seems to be a somewhat larger pool of men accepting that - and it does get an erection to know you are bringing the man on , but you are left to finish yourself by wanking - it would be much more satisfactory to be roughly taken and penetrated .

There never really seems to be a dearth of controlling men ,,, controlling men who are interested in more then just control seem fewer .... and believe me there are a lot of men interested in more then a blow job ... even the peeps have those that want to slip it somewhere other then between your lips.

****** always seems to leave Amanda swooning in satisfaction for awhile and I am a male again. The simple act of dressing completely again gives her time to regain control of my actions and then my male side is simply along for the ride again.


It's kind of funny. The first time I was with a man while I was dressed it was only the second time that I had even touched another man's ****. I actually got dressed, drove to a motel and met a man in his room. (It was after dark, but I still was fully dressed and had to walk across a well lighted parking lot in HIGH heels that I wasn't all that used to walking in). Luckily I didn't knock on the wrong door. Anyway, after he lifted my skirt and checked me out, he undressed and laid on the bed and I (still totally dressed) climbed between his legs and took his **** in my mouth. It was easier than the first time I touched and licked a ****. In fact it felt good to my hands and my mouth. So good that I got excited myself. And before I even knew what was happening, he started to come in my mouth. And I didn't stop him. In fact I sucked even more and swallowed it all--and as I did, I came too! Afterwords, I felt satisfied and drained. I didn't have the second thoughts or shame that I would have expected. Even as I drove home. As I thought about it the next day, I wondered what had happened to me. But I knew I wanted to do it again.

I understand how you feel completely. When I was first starting out I would occasionally feel that guilty feeling and felt like a boy in a dress, then I realized that I wasn't ashamed because I was trans, I was ashamed to be a boy in a dress, I enjoyed being a girl, but due to having the makeup skills of a 9 year old when I first started my transition, and due to a lack of female clothing, I looked more like a boy in a dress and makeup at first and the image looked weird and almost comical to me. Once I learned how to properly apply makeup, and got a few female outfits and started taking hormones, I actually looked like a girl and could pass much easier, which made the shameful feelings disappear since I didn't look like a "boy in a dress" anymore.

I feel like everyone starts off with that uncomfortable feeling at first since it's a new look to them and we live in a world where we're taught to find people who look questionable (gender-wise) to be weird or freaks, so the beginning stage where you don't quite look like your biological gender, but also not quite like the opposite gender either, can be a bit of an uncomfortable stage.

That's just my opinion though :P


Fabulous sweetie

yeah that part where you say( then boom im a man again) i get that but that feeling comes with heaps of guilt and denial and then i think what the hell am i doing dressed up,but then i remind myself its because im a transexual (not had the operation yet and not likely to either) so when i have calmed down i go back to being margarita again.thank you for sharing this experience with us xxx.

Wonderful story, I have never been with a man yet, but I have a boyfriend in Toronto and plan to visit him in the spring and he promises he will make a real woman of my, I am sooo looking forward to getting to know him intimately