Penny

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Submissive student gets more than he bargained for...
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I was in my sophomore year of college when I first met Penny. I remember the exact night I saw her face. It was a warm one in early October, and I was in my room on my computer. I was also wearing a CB6000 male chastity cage.

I know, it sounds crazy, right? I mean, why would any guy willingly lock up his own cock?

Well, I can't speak for anyone else, but for me, the idea of orgasm denial always sort of turned me on. I also figured that it would cause me to focus on something other than my dick, like my seriously mediocre grades. And besides, if I ever wanted to get out, I kept the key close at hand.

That night I was on an online dating site, searching through the profiles of the women listed there. I wondered what it would be like to date them, and how they might react if they knew about my little secret.

As I was flipping through, I got my first glimpse of her. Her name was Penny, and she had the most piercing blue eyes I had ever seen. She also had long brown hair with bangs that framed a beautiful face. My device grew tight as my cock grew hard. It expanded from the base, pulling against my balls. I closed my eyes and took a few deep breaths, trying to relax. I opened them again to see her that face and I decided I had to send her a message.

I said hello, and asked her a question about her favorite author. To my surprise, she responded within five minutes. H.P. Lovecraft, she said. Yours?

Usually, you have to send out lots of messages and wait days for someone to hit you up, but this girl was responding to me right away! Barely believing my good fortune, I told her mine was Orwell.

We messaged through the night, going back and forth as we talked about our aspirations and plans for the future. She was a creative writing major who loved to write horror stories. She hoped to one day get published and maybe move to New York. I told her about my dreams of becoming a historian. We hit it off easily, flirting and joking with each other. Before I knew it, it was 2 AM and I had to go to bed. Summoning my courage, I asked her if she'd like to get coffee at a place I knew, and she agreed. We chatted a bit more before signing off and I turned the computer off for the night.

I tossed and turned that night, unable to sleep because I couldn't stop thinking about her. I was over the moon. I had only had one girlfriend before, and suddenly I had a date with this goddess. I couldn't believe my luck, and when I finally fell asleep, it was filled with dreams of her.

The big decision I would have to make was whether or not to keep my cage on for the date. I thought it would be exciting to wear it secretly in public, and it wasn't like she was going to jump my bones the first time we met.

I walked into the coffee shop and bought a cup. Looking around I saw a young man on his computer and two elderly men playing chess, but no one else. I had almost given up hope of seeing her when there she was seated at a booth in the corner, a warm mug between her hands. She was wearing a pair of black boots that went up to the knee, with black stockings, a black skirt, and a white blouse. She smiled when she saw me, flashing me her bright white teeth.

"John, I presume?"

"Yeah, Penny?" I said, putting out my hand. She took it, and I swear to god, I felt almost electrified by her touch.

"I thought we could sit here, it's a bit more private.", she said, motioning towards the enclosed corner booth she occupied. She had with her some books, and her Macbook's apple logo glowed on the table.

"Someone's an A student." I said.

"Oh, I mostly just read those for fun, she said, holding up a Stephen King first edition. Care to sit?" she asked, patting the spot next to her. I took my seat, and she took my hand in hers, smiling at me slightly.

We sat in the coffee shop, and as we talked, she softly began to rub my upper leg, smiling that same little smile and scooting over so she could get closer to me. She was definitely interested, so I decided to take the plunge.

"Penny, would you mind if I kissed you?" I asked, nervously.

"Not at all.", she whispered, pulling me towards her. Our mouths met, and her tongue explored my throat. To my surprise, her hand travelled northwards, grazing against my jeans and the hard plastic of my chastity cage beneath.

"John, are you wearing a chastity device?" she asked, surprised.

"How, how did you know?" My face went red as a beet, I was so nervous she would freak out. But she just laughed and said,

"My ex-boyfriend used to wear one of those. That's a CB series, right?" She asked this like it was the most normal question in the world.

"Uh, yeah, a CB6000". I couldn't believe this was happening.

"Ah, I guess you're a bit more well-endowed than my ex. He had the CB6000S, and he never had any trouble fitting inside it. Though, maybe I should judge for myself."

Penny grabbed her books and computer and slid out of the booth.

"You coming?" she asked. Speechless, I followed her to the parking lot and a small sedan. I hopped in after her and she took off through the city.

"Where are we going?"

"My house. Roommates aren't home."

"Um, Penny, I don't have my key with me, we'll have to stop by my place first..."

"Did I say anything about unlocking you?" she asked with a sly smile.

"No, but..."

"But nothing. So just sit back and enjoy the ride." Penny stopped upon reaching a blue two-story house in the student ghetto. She rushed me into her room, shutting the door behind her and pushing me onto her queen size bed.

Penny ordered me to strip, revealing the clear plastic cage that imprisoned my member. Penny took it in her hands, looking it over.

"So, I take it you don't have a key holder?" she asked.

"No, I don't. I locked myself up."

"Good boy." she said. She pulled me close and kissed me, her hand reaching around and grabbing my ass cheeks.

"John," she said, "I want to fuck you."

"Well, I can't, I can't..."

"What? You can't fuck me? It's alright, I don't really like getting fucked anyway. I prefer to do the active part.

"What do you mean by that?"

Penny sighed. "Let me level with you John. I have a penis.

"What?!"

Rather than explain further, she pulled up her skirt and reached between her legs, pulling out a cock that was at least eight inches long.

"Holy shit.", I said, staring openmouthed at the massive organ in front of me. Even if I wasn't locked up, she was longer and wider than me. And more importantly, she could actually get hard.

"John, I understand if this is a deal breaker. I don't want to force you into anything. But I have to tell you, right now I really want you bad."

"No, it's not." I said, only half believing what I was saying. Cock or no, she was the hottest woman I had ever seen. Penny, you're a beautiful woman and I want you too." I kissed her, this time my tongue probing her mouth. I grabbed her cock and began to stroke it. She only got bigger and as her cock rested above mine, it nearly obscured it from view completely. My smaller, chastised cock ached as our bodies rubbed against each other.

She noticed me bulging in my cage and said, "Aw, does your cock hurt? Don't worry, once you've experienced mine, you won't think twice about your measly little cock." Penny removed all her clothing except for her boots and stockings, and proceeded to lay back on the bed, stroking her huge member.

I got between her legs and took her between my lips before even she took control. She grabbed my hair and began to face fuck me, her member probing my throat and making me gag. My eyes watered as she pulled all but the head out before ramming it as deep as I could take it.

"That's it baby, suck momma's cock. Make me come!" Her womanly moans contrasted with the very unwomanly things she was doing to me. After what felt like an eternity, she pulled out, only to blast her hot load all over my face.

I struggled to catch my breath as the salty effluence ran down my chin. Penny smiled at me,

"Aw, what's the matter baby? Too big for you?" she asked, smiling.

"You try taking eight inches down your throat." I said, my voice hoarse.

"Its nine inches, baby, and you better get used to it, because I am one horny girl!" she said, motioning to her cock. She wasn't lying. Only a few minutes after cumming all over my face, her cock still pointed straight out from her pelvis.

"Holy shit, you're still hard!" I said, amazed.

"Well yeah, girls are multi orgasmic, silly." she said as if this was the most obvious thing in the world. "Now, why don't you get on your back? You didn't seem to like oral much, maybe we should try something else."

"I, I don't know. I mean, I've never had anything up there."

"Don't worry John, I'll be gentle with you." Unfortunately, it turned out we had different conceptions of gentle. She pushed me onto my back, spread my legs apart, and shoved the head of her cock inside me.

I cried out as it felt like I was being split apart. I tried to scoot away from her, but Penny grabbed my legs and held me in place.

"Relax, baby." She said, looking into my eyes. " Just look at me and breathe. You'll need to adjust to me. I won't push it in any farther until you tell me to, okay?"

"Okay." I said and did as she told me. Taking deep breaths I maintained eye contact with her. Something about staring into her bright blue eyes made me calm down and accept what she was doing to me. After a few long minutes the pain subsided, replaced with an odd full feeling.

"Alright, you can stick the rest in, but go slow."

Penny smiled what winning smile of hers, and pressed deeper into me. To my surprise, I felt not pain, but pleasure." She moaned deeply as she slid inside me.

"That's your prostate." She said, grinding her hips slightly so her cock head rubbed against it. It was a pleasure unlike anything I had ever experienced, one that emanated from deep inside of me. I wrapped my legs around Penny, pulling her closer to me. Before I knew it, Penny was balls deep. I squeezed her tightly to me as she gyrated her hips, every slight motion filling me with pleasure. To my surprise, my cock was completely limp in its cage.

Penny kissed me, her tongue and cock probing me in unison as she moaned into my mouth. She broke the kiss and nibbled on my ear, before whispering.

"Are you ready for it?"

"Ready for wha..."

Before I could get the word out, she pulled out of me, nearly lifting me clear off the bed as she did so, until only the head remained inside me. I felt strangely empty for a moment or two, before she rammed all the way back into me. My ass exploded in a combination of pain and pleasure as she repeated the motion. Her cock plunged in and out of my deflowered hole, her thighs slapping against me as she did so. This was all about her now.

I reached out and grabbed her breasts, tweaking her small dark nipples. She moaned in pleasure as I did the same, desperate to have as much of her inside me as possible.

"Oh yes!" She cried, "I want to come inside you!" Penny kissed me once more as I felt her cock expand and twitch inside of me, emptying another hot load into my bowels. She collapsed on top of me, struggling for air as her orgasm raced through her body.

Her twitching cock electrified my prostate, and I felt it. My ass spasmed around her cock, and my own limp member dribbled out semen which leaked out through the hole at the end of my device. A hands-free orgasm? I wondered to myself, though in truth this was far more intense than anything I had ever felt.

"Was it good for you, baby?" Penny asked, her hair sweaty and sticking to her skin and her large cock still buried in me.

"No," I said, "it was incredible." We kissed once more, slow and passionate.

She withdrew from me, and the empty feeling returned. She rolled over, laying next to me and holding me close to her. We fell asleep there, basking together in the afterglow of truly amazing sex.

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AnonymousAnonymousover 4 years ago
Perfection

This is all I would ever want in life and I hope you carry on writing more

xploring96xploring96over 6 years ago

Such a sexy premise that a locked up bitch like that would be fucked by a Dom hung tranny. Would love to read more about these two.

AnonymousAnonymousabout 7 years ago
What next?

What happens when the roommates show up? ;-)

tensunny09tensunny09about 7 years ago
Awesome

Great story, absolutely loved the combination of chastity and a girl with a dick, and also that the overall tone was positive, that is, he wasn't "forced" into anything and greatly enjoys chastity himself.

Please write a second chapter! I'd love to see how she becomes a very strict keyholder and both adopt their rooles in the relationship, she as the top, he as the bottom. She has him suck her off in the morning, fucks him regularly, while he is teased mercilessly by her and his dick is only let out 1-2 times per month, and even then almost always only for edging etc.

spankmeagin001spankmeagin001over 7 years ago
Thoroughly enjoyed and left me tingling

An absolute dream come true, one that I have wanted to live in real time. Congrats, please share more!

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