Jenny Plays with the Big Girls Ch. 10

Below is part 10 of my story "Jenny Plays with the Big Girls". Sorry it took so long for this to come out, but the ideas are starting to take longer to come to me and the stories are taking longer to finish. Again, thanks for all the support and feedback offered during the writing process for this and my other stories.

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Nearly thirty minutes later, Cindy and Jenny finally arrived at the movie theater where they planned to somehow leave the money they had collected to pay for the damages incurred after last night's bacchanalian fiesta.

They had left an anonymously written note apologizing for their role in the debacle, and hoped that, along with the $2000, it would be enough to appease the manager's ire.

"Alright, Jenny," Cindi said. "You take the envelope on inside and put it on top of the Manager's desk, pretty much in plain sight so it won't be too hard for him to find, okay?"

"Me? I've got to do this?" Jenny asked, with a squeal. "Why me? Why can't you do it?"

"Because I'm driving," Cindi replied. "Look, if we need to make a quick get-away, I'm a lot better driver than you are, and you know it. So I'll wait for you here. Besides, you know Lori would rather you handle such a delicate matter than me."

Realizing the truth in that statement, Jenny could only agree to complete the assignment at hand.

Reaching into the glove-box, Cindi pulled out a ten dollar bill.

"Here," she said. "Go up to the girl and buy a ticket for one of the films. Once inside, sneak off toward the management's office and, after making sure it's empty, put the money on his desk and leave. Easy as pie. Okay?"

"Okay, okay," Jenny said, though not happily.

With that, she exited the car and purchased a ticket for 'Avatar'. At the window, the girl looked at her funny and said, "Don't I know you? Are you from around here?"

Looking back at her, Jenny replied, "I've only been here once before, and when I was, you weren't on duty. And no, I'm not from around here. You must have me confused with someone else."

"No, no, I'm sure it was you," she said insistently. "Are you in films or something like that? Maybe I saw you there?"

"No, it couldn't be that," Jenny answered. "I'm just a student at State, going into my Sophomore year next semester."

"Hmmm," She said, shaking her head in amazement. "So fucking familiar. Hard to believe. Well, enjoy the film."

"Thanks," Jenny replied. "Have a nice evening."

After buying a ticket for "Avatar", Jenny went into the theater, puzzling over the conversation she'd just had with the girl in the ticket booth.

Once inside, after handing her ticket off to the ticket taker, who also seemed to eye her curiously, she veered off to the left, turning toward the restrooms, so as not to appear too suspicious.

Seeing a hallway to the left of the restroom doors, Jenny began walking down it until she came to an open door marked *Manager*.

Noticing it was empty, she went inside and saw a desk and chair, and a calendar on the wall. The desk was cluttered with papers, which gave it a completely professional appearance.

She cleared a spot on the desk so that the envelope could be seen amidst all the clutter, put it down, then turned to leave.

As she turned, she heard the door to the office close and her forward momentum caused her to bump into a rather large though quite handsome gentleman standing there before her.

"Ah ha," he said. "My little strumpet has returned at long last. I thought perhaps I'd never see you again."

"Uh...umm..." Jenny stammered, not knowing at all what to say. "Really, I must be going now."

"Oh, please stay," the manager insisted. "You've only just arrived. It would be a pity if you left so soon. And we've so much to talk about -- really we do."

"Well, if you insist," Jenny answered, totally intimidated by this large, gorgeous man. "But really, I have no idea how you could know me. I've never met you before today, but you talk as if we've been acquainted for some time."

"I'm truly sorry about that, my dear," he replied. "Even though I've only known you for nearly all of a 24 hour period, I feel as if I've known you all my life, my love.

"Let me introduce myself. My name is Hawthorne, Daniel Hawthorne. I am the Manager of this establishment. You are Jenny Watson, sexy transvestite brother of Lori Watson and friend to a girl named Cindi. How am I doing so far?"

"Oh my god," Jenny gasped, ready to faint. "How do you...did you...I don't understand."

"Oh, well you see, missy," Daniel started. "That little donnybrook you and your friends played out last night in the balcony here? You may have thought what happened up there was all done pretty much on the QT, but you see, I happen to have some quirks of my own, and one of them is voyeurism.

"I really like peeking on certain people who try to hide what they don't want others to see. Usually, its just a bunch of kids necking and making out, and occasionally a bit more than that, but you guys last night, well, you really took it way past the next level, I must say.

"Oh, and I should add here, the surveillance equipment I had installed there includes sound as well, so not only did I see everything but I heard it too.

"So, as you can guess, I have watched that sucker all night, all day and the rest of this early evening. I can't tell you how many times I have cum just watching the things those boys did to you."

As Daniel continued talking, Jenny began shivering, both in lustful pleasure remembering the previous night's fun and games, and the fact that this handsome man had been sitting here watching them and was now aware of what they'd done last night as well. Slowly, he advanced on her while continuing his talk, noticing she remained where she was, almost trance-like.

Daniel's eyes began traveling up her body, stopping at each exciting point on its way to her face.

"It's been a long time since I saw such a beautiful woman and in such a tiny bikini," he said. "That you aren't a real woman makes you doubly so."

As he talked he was moving closer to her until he was just touching her with his body.

He leaned down and lifted her face up to his. His lips came down to cover hers. Jenny turned her face away. "Stop, Mr. Hawthorne" she protested. "What are you dong?"

"Kissing the sexist woman I have ever seen," he said. "And call me Daniel, please."

"Don't, Daniel, please," Jenny said. "Someone might come in."

Daniel noticed that she didn't put up much resistance. She was mostly worried that someone might catch them. He leaned over and locked the door and turned back to Jenny.

He let his hands trail up her arms. He could feel the chills that passed over her body as his fingers touched her. He leaned forward again and kissed her.

His fingers held her face straight when she tried to turn away. With a hand on each side of her face he turned her face upward until his lips covered hers again.

Jenny tried to move away but he held her in a firm grip. What was happening to her? She had never expected anything like this to happen when the girls asked her to deliver the money here. If Cindi had just come in with her, then none of this would have happened.

Suddenly Daniel's lips found Jenny's and his mouth opened as his tongue began playing across her closed mouth.

Once again she tried to twist away but couldn't move. His body had now pushed her back against the locked door and Jenny could feel his hard cock pushing against her fake pussy, and he wasn't backing away.

Daniel kept the kiss going. His tongue pushed arduously against Jenny's mouth, asking her to open to him. He wasn't having much luck but it was fun and her fake nipples pushing against his sturdy chest were turning him on more and more.

He dropped his hands from her face and noticed she didn't make any effort to turn away. Jenny was beginning to really like the way he kissed her. It was a struggle not to give in and to just open her mouth and let him have his way.

She hadn't even realized his hands had left her face until she felt them on her arms. Even then she didn't try to pull her mouth away, a fact Daniel recognized at once.

When his hands reached her shoulders, Daniel gently slid the straps that held her top from her shoulders. He backed away just enough to let the top slip down, almost baring her breasts to him.

Jenny felt the top slip and quickly broke the kiss and pushed him back. "Daniel! No! Don't do that."

Her hands held the top over her tits. He could see some of the nipple through her fingers. "Let me see you."

"NO!"

"Please?"

He sounded like a young boy begging for a toy. She laughed, despite the situation. "No. Someone might come in."

"Don't be daft!" he said. "You saw me lock the door. Nobody's going to be coming in. Come on, I've never seen fake tits on a boy before. Let me see them and I'll go back out and leave you alone."

He reached for her hands that held the top up. Gently he pulled at them. At first Jenny resisted, then let him separate her hands until the top dropped to her waist.

He pulled her hands farther apart until she was naked to her waist before him. "I knew they were going to be beautiful, just like the rest of you." He leaned forward and kissed the nipple of each one.

Jenny pulled his head away. "You promised."

Then it was too late. Daniel pulled her body to him and brought his mouth down to hers. She turned her head away from his lips and he kissed the side of her neck. Another bad move on her part. Jenny's neck was one of her hot points and as soon as his lips found it he knew.

"See that wasn't so bad was it?" Jenny couldn't find her voice to talk.

Daniel kissed her neck and ears until she was shaking. The next time he moved to kiss her lips she didn't back away. His lips found hers and when his tongue went searching her lips she simply opened her mouth to him.

Jenny knew he could do anything he wanted to her now. His tongue was working her mouth over when he pulled the tiny blond girly-boy tighter to him. She could feel her fake tits touching his barrel chest and it was making her so very hot and ready for this man.

Her arms seemed to move by themselves as they moved around his neck to pull his mouth even closer. The thought of sex with this man popped into her mind and she knew now that it had an overwhelming appeal all its own.

She gave her body over to Daniel then. He could do what he wanted with her. "Daniel, Daniel. Please, please, take me, take me here, take me now."

He broke the kiss but didn't release her. He could feel her shaking and knew that he had succeeded in seducing her. All he needed now was time and some room to work.

Looking around his office, Daniel realized he'd picked the worst place to begin his seduction of this little morsel, but the more he thought on it, the more it became painfully clear that there was no other place here that was any more secure or available where they could get the job done, as it were.

Finally, not wanting to lose the moment, Daniel simply shrugged and pushed aside all the papers on his desk to the floor with an uncaring shove and lifted our hapless Jenny up onto it and lay her back onto it gently. As he did so, he easily slipped her bikini bottoms off her, without any protest from the girl.

Jenny was, in fact, so far out of it, breathing harshly and staring up at the ceiling, that she was completely unaware of having been stripped of her last vestige of clothing.

Daniel would have laughed at the sight, so amused was he at how this girly-boy had so easily and so quickly been turned into such a slut. Yes, it would have been funny if he weren't so turned on by the transvestite, and from watching the video of what they'd had him do the night before.

Jenny didn't know it, but Daniel had made a number of copies of the tape and sold them to movie houses all over the city where they were playing as a special presentation to sold-out audiences already, even after only 24 hours.

He had blurred out the faces and bleeped out any mention of names, but the ass fucking, cum shots and golden showers were all visible in glorious Technicolor. And hearing the girly-boy begging for more was the creme-de-le-creme.

And now, here little Jenny had walked right back into his establishment, into his waiting arms, like Little Red Riding Hood to the Big Bad Wolf and there was no hunter around to protect her. Who would ever have guessed?

Slowly, methodically, Daniel began divesting himself of his clothes. First removing his jacket and tie, he then took off his shirt, shoes and pants. Finally, he slipped off his underwear, leaving only his socks on his feet.

When Jenny saw the size of Daniel's cock as it protruded out from his loins as though it was some sort of lethal weapon taking aim at her, her breathing grew even more erratic and labored as she felt herself lusting even moreso for this man before her.

"Oh, God," Jenny gasped involuntarily, as her eyes took in the sight of such a massive delightful tool coming her way. "You're so big! What is it - nine inches?"

"Closer to ten, really," Daniel said, then added with a chuckle, "Though not quite, although if I keep looking at you long enough, I may get there."

"Oh God, then please," she begged. "You've already got me so hot. Please, fuck me now, please, give me the fucking I need."

Looking down at her, Daniel was really not comfortable with this situation he was presented with.

"Jenny," he said. "Let's get you off the desk for a moment."

When she was off and standing by it, he turned her so that her back was to him. Looking over her shoulder at him with a sexy smile, she then, after a gentle nudge from Daniel, settled herself down on the edge of the desk on her elbows so that her ass was pushed up into the air towards him.

She wiggled her legs apart. She knew she was opened up for him. How wicked this was, how sinfully delightful!

He took in the sight before him. Just like that, her ass cheeks were wide open, exposing the pretty, dark pink anus.

Daniel grasped Jenny's ass cheeks and pulled them further apart, opening her up as much as possible. His thumbs gripped deep in the cleft of her ass, stretching the tender skin there.

He leaned his torso forward and settled his still achingly hard cock into that valley, fitting it neatly between the plump cheeks so that the underside of his erection dragged across her anus.

Jenny had never felt so alive since these past two days when she'd started taking it up the ass, and it had become so much more enjoyable simply because she accepted that she was now Jenny.

Daniel was in heaven, as well. Every inch of his cock felt electric. He dragged the length of it up and down her ass. Jenny was leaning deeply onto the desk, her head turned away from him so he could only see her golden blonde hair.

He pulled down now, the head of his cock slipping deep into her ass cleft. He looked down and saw it poised right over her anus, his sensitive skin rubbing against the dark wrinkles of her hole.

"Mmmm, nice," Jenny murmured.

Her rosebud winked at him, like an offering to the gods. It was a feast, and he was determined to partake. He backed up and knelt behind her and began to lick the cheeks of her ass.

"Oh! What are you doing?" Jenny's squeal turned into a moan as he worked his tongue over her ass, moving ever inward.

"No, Daniel," she said again with urgency. "No, honey, you can't dooooo that! Oh, fuck, it's too fucking dirty, sweetie! Nobody's ever done that to me before!"

But she made no movement to stop him, her cries only encouraging him to continue. In fact, Jenny felt her hips move back towards him as Daniel traveled the last inch to come into contact with that dirtiest of places.

He felt the wrinkled skin under his tongue and rejoiced in the feel of it. It tasted a little bitter, but then sweet as well, the feel of Jenny's asshole. He worked around it with his tongue, the rim of muscles bunching against him. Then it pushed against her, and wondrously slipped inside, stimulating her anus on all sides at once.

"Ohhhhhh... Fuuuuuuuck, you sweet, sweet man!!" Jenny moaned.

Her anus captured his tongue and held it there, as he lovingly rimmed her out. Daniel had never done this before, but it felt so natural, so perfect with this woman, this...this...girly boy. He could think of nowhere else he would ever want to be but settled between Jenny's ass cheeks.

As for Jenny, her dick was pulsing under her fake pussy, and she was continuously groaning into her folded arms, pushing her ass out, fucking against his mouth as Daniel started pushing in and out with his tongue.

It was like a miniature cock inside her, so insistent, moving back and forth within her. Soon, Jenny found herself, almost against her will, pulled over the edge of an incredibly intense orgasm.

"Oh fuck, Daniel! Oh, oh, oh, OHHHHHHHHH!"

She writhed and shivered under his tongue and fingers, the orgasm ripping through her like a hurricane. She pushed hard against him, deep-seating his tongue even further inside her ass, then collapsed down onto the desk, feeling his tongue slowly slip from out of her ass.

"Oh. Oh. Oh, shit, Daniel," Jenny cried. "Where the fuck did you learn to do that?"

Her breath came in ragged gasps. He leaned his face sideways against her ass, the hot skin like the best cushion in the world.

"It just came naturally, Jenny," Daniel replied with a grin. "You inspired me, that's all."

"Well, if that's natural to you, I'd hate to see what kinky is," she giggled, and they both found themselves laughing.

Standing once again, Daniel lodged his massive cock in Jenny's ass cheeks, then lay himself over her prone body. Looking back, she locked eyes with him.

"Kiss me, you wonderful man," she smiled.

Daniel leaned into her, that tongue that had just been up her ass now probing forcefully between Jenny's lips. She tasted herself on him, a thought that up until now would have disgusted her. But how could she deny him, this man who had given her so wonderful an experience?

"Now," Jenny said, in a voice of exasperation. "Can we finally get around to fucking?"

Suddenly, there was a knock at the door.

"Mr Hawthorne," someone called out. "Mr. Hawthorne, the manager of the Pussy-Cat theater is here about the film you mentioned you had for him. Mr. Hawthorne."

"Film?" Jenny asked.

"Oh yes," Daniel answered. "Did I forget to mention that you and your friends have become the cause celebre in the porn circuit ever since last night's movie was made. Your film has made you guys the hottest ticket item since Deep Throat!"

"Oh shit," Jenny said woefully. "And Mother's still in town!"