Chapter 2 – Penetration
As the reality of his predicament hit him, Norman became extremely nervous and was about to refuse. He remembered, however, his sister’s threat to show the pictures and thought better of it. And, she had taken additional pictures of him dressing in the feminine garments that would only add to his humiliation.
“Where are we going?” Nancy asked as they pulled out of the driveway.
“Well, we thought you might like a new dress to wear to the party tomorrow,” Andrea replied, “and since you have been saving your money, you can afford to buy one”
Nancy became angry as he saw that Andrea had the wallet in which he was saving his money.
“I was saving up for a new stereo. I am not gonna use it to buy a dress”.
“Don’t be silly, a girl would much rather have a new dress, and, in any case, I don’t remember asking you.” “I’m not a girl!”
“Lois, stop the car and we’ll ask a perfect stranger if Nancy is a boy or girl?”
“No! Don’t do that. I’ll buy the dress” he said meekly.
Nancy found herself holding back tears as she wondered why his step sister hated him so much and how far she would go to humiliate him. He knew better than to argue at this point.
Lois parked the car and the three girls got out. Walking very self consciously between Andrea and Lois, Nancy kept her eyes to the ground and dared not look at anyone they passed. She was mortified she would be recognized as a boy.
She was taken into a dress shop, whose name she recognized since Andrea had talked about it. It was where she usually bought her dresses. The owner greeted the two girls by name.
“This is my step brother Norman. He likes and insist he has to dress up like a girl at all times, or at least most of the time. Lois and I agreed to take him shopping here for a new dress and other things he can wear to a party tomorrow night. He insists we call him Nancy.”
“Well, I am used to boys coming in here to try on dresses. You would be amazed at how many like to dress up like girls, though many are not here voluntarily. I will let my best salesgirl handle Nancy. She has had much experience with this sort of thing.”
“Maureen, this is Norman, who prefers Nancy. Will you help her to pick out a dress for a party she will be attending tomorrow night?”
She led Nancy to a rack full of party dresses. After taking some measurements, she picked out a couple of dresses and led Nancy to the dressing room.
It was furnished with a comfortable couch and a rack with hangars for the clothes.
“Alright Nancy, take off your dress so that you can try some of these on.”
She started to explain that wearing the feminine attire was not her idea, but Maureen didn’t seem interested. She removed her dress and stood there in the minislip she was wearing, feeling very vulnerable. She tried on several dresses, finally settling on a purple and white see-through. Maureen left the room and came back with a white slip.
“Put this on, it will look better under the dress.”
Nancy was embarrassed to strip that far, but her protests fell on deaf ears. As she removed her slip, Maureen could see the excitement Nancy was feeling.
Maureen locked the dressing room door and moved towards Nancy, who was wearing only her bra and panties. She removed her dress and slip as she advanced on the feminized boy. She reached into Nancy’s panties and grabbed her throbbing cock.
