LA was a way different town back in '70. You could walk the streets at night in most neighborhoods and the gangs hadn't taken over yet. There was still a trace of that heady excitement, that bubbling sense of unlimited possibilities that was the short-lived legacy of the Sixties.
Jamie was fresh off the bus. Not quite as clueless as fresh off the boat, but close. He had walked out of the Greyhound terminal with suitcase in hand, seventy dollars and change in his pocket, and no place to stay. Not much in the way of plans, either... except to survive, and maybe manage to lose his virginity in this city of infinite opportunity.
He pointed himself toward downtown and began walking. And kept walking. It was late in the afternoon and starting to get dark, and he was getting mighty tired of walking.
A car pulled up alongside.
"Need a ride, kid?"
The woman in the driver's seat was smiling at him. She was blonde, filled out her sweater quite nicely, and looked to be somewhere in her thirties. Well, maybe late thirties. She spoke louder. "You! I'm talking to you, fellow. I asked if you needed a ride."
"Sorry, ma'am. It's been a long day, and I'm tired. Sure, I'd certainly appreciate a lift. Thanks."
The trunk popped open. "Toss in that case of yours and hop in."
Jamie got in the back seat. It was plush leather. Very plush. Now he noticed that the car was a Bentley. Money. Mucho money here.
"Uh, nowhere in particular. Just drop me off wherever you're going and I'll take it from there."
"New in town?"
"How did you know?"
"Suitcase, bedraggled look, and no particular destination in mind. You don't have a place to stay, do you?"
"Maybe I can help you out, kid. I've got a spare bedroom, and if you don't mind earning your keep... The name's Theodora, by the way. You can call me Dora."
She lived in a mansion. It was a fairy-tale castle with something like fifty rooms. Jamie slept on a cot in a room that was part of a medieval turret. The walls were curved and the ceiling came to a conical point. Not much light came through the single small arrow-slit window.
On the maid's days off, Jamie washed the dishes, made the beds, and swept up around the house. He also did light maintenance and fixed dripping faucets. It typically took about two hours of the day and the rest of the time was his own. Not bad for room and board. On the other hand, he wasn't putting any money in the bank, either.
He had been living there for a week, and it was starting to get boring. Aside from watching TV on the large-screen color set in the living room and reading pulp novels, there just wasn't a hell of a lot to do. Public transportation didn't run in that neighborhood, so he couldn't make it into town. Jamie was seriously considering leaving and taking his chances again.
He hardly ever saw Dora. She swept in and out like a cyclone. She was an actress of some sort, and apparently successful enough at it that she was always working. That had been fine with him in the first few days, when he had still been getting settled in, but now he was lonely. Lack of human contact was driving him nuts.
Jamie had always known he was different. Growing up in a working
class family with two brothers and five sisters meant being ignored
most of the time. He had felt out of place and unwelcome. And he kept
having these weird dreams... dreams of being a different person,
of being in a different body. His family laughed at him and slapped
him down when he tried to talk about it. His schoolmates tormented
him. His friends... well, he had no friends. He had left home at
the first opportunity.
Late one night there was a soft knock on the door. Jamie was instantly awake. "Who's there?"
"May I come in?" It was Dora's voice.
Before Jamie could answer, the door slowly opened. The foot of the cot sagged under Dora's weight.
"Time to earn your keep," she said.
In the scant light seeping into the room from the hall, he could just barely make out her silhouette. He reached for her. She wasn't naked... quite. She had on some kind of form-fitting bodysuit. Nice boobs, nicely rounded ass. There seemed to be a funny kind of bulge down in front at the crotch, but... he had no time to think on it as Dora abruptly stood, then turn her back to him. "Unzip me," she said.
A zipper ran straight down the length of her catsuit, from the neckline to past the buttocks. Jamie pulled it down, all the way down. He hesitantly touched a bare cheek -- a warm, smooth ass cheek.
She grasped his hand and pulled it into a warm place. "Yes, that's it," she said. "That's right where I want it. Fuck me. Fuck me here. Fuck me in the ass. Put it in there, stud."
In a flowing, feline motion, she twisted around and bent facedown over the bed. He traced the curve of her bare bottom with trembling fingertips. And there! In the valley between the buttocks was that puckered little opening. It was wet, slick. She must have already lubed herself.
He had never done anyone in the ass. Well, there was that once with his friend Tommy... but that didn't really count. It was just a couple of guys fooling around.
Oh, that was good! His cock had slid right in with barely any resistance. He was in the burning embrace of a tight velveteen pouch. He could feel the liquid rippling texture of her gut as he slowly moved in and out. It felt -- it felt just plain good. Not all that much different from being inside a pussy. Yeah, maybe a little hotter and tighter.
It was the best fuck he'd had in a long while. Thoroughly satisfying. Utterly draining. Jamie wanted nothing more than to just lay down and sleep for a month.
"My turn now," Dora said.
Dora was standing there smiling at him, and in the faint light Jamie saw the silhouette of an enormous hard cock pointing straight at him.
"Wait a fucking minute!" Jamie screamed.
"You have a simple choice," Dora said. "Take it in the ass, or toss your things in a suitcase and start walking."
It wasn't all that tough a decision. Jamie had no money and no place to go. And he had let Tommie put his dick into him that one time. Sure, just a couple of inches deep. Just to see how it felt. It hadn't been all that bad, but they had been afraid to go any further.
Jamie was lying on his side with his knees pulled up toward his chest. Dora, or whoever she or it was, curled up close behind him. This was supposed to be a "beginner's" position. It would make being penetrated easier for someone not used to it, or so Dora said. Cool hands were massaging Jamie's neck and he was starting to loosen up.
"I'm right at the entrance. Feel it?" Dora said. "Now exhale and press gently out. That will open you up."
Jamie gasped as he felt himself stretch open down there. There was a slight burning sensation as she entered him.
"And away we go," Dora said.
The cock began sliding deeper inside and Jamie started to tense up. Dora pressed a spot on his lower spine and he felt his entire pelvic girdle go slack.
"Accupressure," Dora said. "Works better than a muscle relaxant."
Now he felt her crotch grinding against his buttocks. She was all the way up inside him. She was fucking him.
She pumped in and out for what must have been a good half hour. Strangely enough, he didn't feel any discomfort -- just a slight soreness that passed after the first few minutes. Then it started to feel good. After a while his own dick was hard and throbbing, and the pressure was building up in his balls. A little later he found out how intense a penetration orgasm was.
"Who are you?" he whispered.
"Hush," she said, sealing his lips with a kiss.
Dora joined him for breakfast in the morning.
.... There is more of this story ...