Sissy Station - early days

Early Days as a Sissy

Your feminisation was a lifelong goal, but it was too hard to do much more than sneak an occasional pair of pantyhose when you lived at home. You really discovered yourself at university, when you moved away from home and had freedom for the first time.
There were endless opportunities to dress up for parties and the girls were always very keen to get a man into drag. Do you remember your first time?

Katie wasn't even a girlfriend at the time, just a friend on your course, but she insisted you borrow her sluttiest clothes and a quality wig. She 'persuaded you' to shave your legs and she shaped your eyebrows to go with the heavy make up. It was your first experience of full drag and you loved it, didn't you?
Obviously, you dated Katie after that. Who would want to let her get away? She was quite into crossdressing, often teasing you to wear her lingerie...

You pretended to object, but you both knew you enjoyed it. She would dress you up in a sissyish outfit to go shopping but get so turned on she usually fucked you before you went out the door.

There were more fancy dress parties and she always made you go as a woman...

The most elaborate, and your all-time favourite, was a full, 1950s evening gown...

You loved that outfit so much! You kept lifting your petticoats, just to experience the exquisitely feminine sensations...

...but this was when things turned sour and Katie realised you were more interested in her clothes than her.

Now you'd been introduced to femininity, you couldn't get enough.

You wore lingerie under your male things and began pushing yourself further towards public exposure. Finally, you were caught out, but the humiliation kept you in wet dreams for months...

You enjoyed it so much, you did it again with a new girlfriend who laughed then dumped you...

You continued to experiment, getting bolder. You tried driving in a skirt...

dropping your trousers in a quiet park to show off your pantyhose...

going out at night in casual clothes and heavy make up...

even jogging in shorts and pantyhose...

They were good days. Then the world of work arrived with the constant delights of smartly dressed female colleagues to fuel your fantasies. You wear pantyhose almost every day by now...

When a charity fundraisng day comes round, you notice some of the office girls seem to be whispering about you and giggling. You begin to wonder whether you've been found out...

...then they approach you and ask if you have any ideas to raise funds for such a good cause. They suggest sponsoring you to come to work dressed as a woman and ask if you would be willing. You nearly pee your panties with excitement! Trying to be cool, you ask what they had in mind, trying to memorise every word for your fantasies later. You find yourself agreeing to a smart suit with a miniskirt, heels, pantyhose and lingerie. One of the girls suggests you shave your legs and you end up being 'persuaded' into a session at a salon including nails and leg waxing. You have to excuse yourself from the conversation to avoid cumming in your panties.
So, a few, agonisingly long weeks later you make your sissy debut at work...