Good Night, My Pretty

by sourdough

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Rape, Magic, TransGender, Fiction, .

Desc: Sex Story: Frank rapes a woman and then listens to her story.

Frank McGuire and the woman saw each other at the same time. "Oh, no," she cried. "Please, not you." She turned to run.

"Not so fast, honey," said Frank. He was on the wrong side of 40 but he was still strong and quick. He grabbed the woman around the waist before she'd run two steps. Damn! Frank thought. The bitch knew I was going to rape her even before I knew it. His prick was already stiffening in his pants.

"P-please don't," the frightened woman begged. "I'll give you money. I'll give you anything."

"One thing at a time, sweetie; first things first. I haven't been with a beauty like you in a long time." He reached up and gave her breast a squeeze. Nice. The woman opened her mouth and took a deep breath to scream but Frank was ready for her and stuffed a dirty rag in her mouth before she could get out another sound.

Frank dragged his struggling burden into a darkened alcove hidden by a large trash dumpster. There were no security cameras as far as Frank could see. Good. She was dressed in a smartly tailored jacket, blouse and slacks but the man wasn't interested in her fashion statement. With quick efficiency he pulled down her slacks. Her panties followed. The woman renewed her struggle but Frank wasn't worried. Hers was a lost cause. He bent her over a concrete abutment, freed his prick from his clothes and penetrated her easily.

Ha! Despite her protests she was really wet. She must have wanted it after all. Well, they all did, didn't they? The fight went out of the young, pretty thing immediately. Frank was grateful for that. He wouldn't have to hurt her. He settled down to have a nice, leisurely fuck. The bitch wasn't being responsive at all but Frank didn't care. He just wanted to get his rocks off. Well, not this quickly. He was already beginning to cum. The bitch was really tight.

After emptying himself inside her Frank popped his head up and took a look around. It was late at night and the parking lot behind the office building was mostly empty but one couldn't be too careful. With a little luck he could rest a bit and then have another go at her. "If you promise to behave I'll take the rag out. Understand?"

The young beauty nodded her head and took a deep breath when Frank pried the rag out. "Thanks," she said. "Listen, I uh, have a story to tell you before it's too late. You won't believe me but it's all true."

"Well, I don't have any other pressing engagements tonight," said Frank, "so I'm all ears." This was interesting. Most of them were pleading with him not to hurt them or not to touch them and to let them go. This one wanted to tell him a story.

The woman nodded her head again. "My name is Wendy Thomas."

"Dick Cheney's the name," said Frank. "Pleasure to meet you, Wendy."

"Three years ago my name was Walter Thomas." Huh? She wants to tell a fairy tale unless she's undergone one of those sex change operations.

"Damn, Wendy. Those surgeons can work miracles these days. I would've sworn you were born a girl." The thought that he just fucked a former man didn't bother Frank at all. Jail time could do that to a guy.

"I didn't have surgery. I was transformed into a woman by a witch." This is great thought Frank. Not only does she provide good nookie but she tells jokes too. Frank didn't mind playing along.

"Gee, I'm sorry to hear that, Wendy. How did you run afoul of a witch?"

"I tried to rape her daughter," said Wendy. "I was handsome, fairly well to do and 21 years old. I knew I was God's gift to women and I was very successful with the ladies. I think that's what spoiled me. If a girl I took a fancy to didn't realize how privileged she was to be in my presence I took it upon myself to educate her. That usually meant raping her if I had to. I was always lucky and no one ever filed a complaint against me.

"I liked to take drives out to the country and hike to keep in shape. I was walking on one of my favorite trails when I happened upon a young girl. She was meditating beside a stream and didn't see or hear me. She was the most beautiful girl I'd ever seen and not more than 16 years old. Even with my ego I knew she was way above my class and was unlikely to get the time of day from her. But I wanted her and I was going to have her.

"Basically using the same technique you used on me I was on her before she could cry out tearing at her clothes and mine intent on popping her cherry. Just then I heard a voice behind me yelling at me to stop. Turning around I beheld an older version of the girl I was holding down. It turned out to be her mother. 'I'm afraid you're going to have to wait your turn, ' I said. 'I'll get to you in a bit.'

"'I don't think so, ' the woman responded. She said a few words I didn't understand. I blacked out and when I woke up I was changed."

"Gee, that's rough, Wendy. What did you do next?" Frank was going to enjoy retelling this story to a couple of his buddies.

"Naturally I begged for forgiveness and to be changed back to normal. As you might surmise she refused. If I had succeeded in raping her daughter she said my death would have been slow and excruciatingly painful but since I was stopped in time she felt I should enjoy some of the joys and tribulations of womanhood for a while.

"The phrase 'for a while' gave me a little hope and I asked her what that meant. She said if I found someone more worthy I might change places with him. I didn't know what that meant but before I could ask her she disappeared and I was alone. I walked back to my car, drove it to the airport and abandoned it. I cut off all my ties and started a new life as a woman. My parents filed a missing person report but, of course, I was never found. I had a little cash hidden away so I purchased a fake identification and diploma on the black market and got a job as an accountant."

"I take it you're still looking for the man who's more worthy," said Frank.

"No," she said. "I found him. He's you."

"Ha! That's a good one, Wendy. At least I could start charging for what I like to do best. However, I don't intend to start growing tits any time soon. Sorry. How do figure I'm the guy you're looking for?"

"I just knew, that's all. Call it woman's intuition." Frank noticed she smiled for the first since they met. It was a nice smile. "I finally figured out the witch wanted me to experience the horror of rape. With that in mind I started hanging out in clubs and became the biggest prick teaser in town. I succeeded in being raped, numerous times in fact but nothing happened. I'd begun to think I was wrong but tonight we met and the moment I laid eyes on you I knew you were the one if you succeeded in raping me. You must have led a very dissolute life, Mr. Cheney."

"Well, let's just say I'm no angel," said Frank. "Why were you so upset if you knew I was the one to take your place?"

"Just look at yourself, Mr. Cheney. You're old and ugly."

"Hey, wait a minute, sweetheart. I'm 38. That ain't old. As far as looks are concerned beauty is in the eyes of the beholder, you know." Well, he'd been called ugly his whole life. He thought he'd be used to it by now but he wasn't.

"I was hoping for someone who was young, healthy and wealthy. I have the rottenest feeling the witch sent you to me on purpose."

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Story tagged with:
Ma/Fa / Rape / Magic / TransGender / Fiction /