Karen and Penny's Play Date

by Sevispac

Copyright© 2013 by Sevispac

Coming of Age Sex Story: After Karen Wagner created the genre with her original Karen's Week Naked in School I was the first to take her up on her generous offer to expand on her universe and characters. I was fascinated by Karen's description of the young girl freshman who was so traumatized by being put in the program that she needed counseling before she was forced to repeat her week. Penny Lovelace became a central character in this and other stories. Here Karen helps her get over her shyness.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   ft/ft   Fa/ft   Reluctant   Heterosexual   MaleDom   First   Oral Sex   Petting   Exhibitionism   Voyeurism   Nudism   .

I was up in my room doing my homework when the doorbell rang. I took off all my clothes when I got home, so I was going to answer it naked. I should probably mention I was naked because I found out how much fun it is to go without clothes. I'm not an exhibitionist ... correction, I didn't used to be an exhibitionist, but my school has a new program called the Girl's Enhancement Project which requires five girls to attend classes in the nude each week. I was one of the first five picked, and by the end of the week I was really having a wonderful time. I learned how much fun it is to try new things and expand my horizons. Those new things included blow jobs, butt plugs, and gang bangs!

My name is Karen Wagner.

At the same time I was learning to enjoy the benefits of going naked, one of the other girls in the program was having a terrible time. Penny came from a very repressive family, and when the school made her take her clothes off she was so upset she had to go to the school psychiatrist. The next week our principle asked me to make friends with Penny and try to help her adjust to the program because I had done so well and had so much fun.

Penny and I got along very well, even though she is only a freshman and two years younger than me. I even got her to go to the mall with me naked, and by the time we went home she was loving it. Just like me, she was embarrassed to be naked in public at first, but when she got used to being the center of attention she really blossomed. She ended up getting her titty pierced, and we both got our hair done at the Purrfect Pussy. Then we picked out some toys, and I gave her something to help out with her mother, who was the reason for all the sexual repression in her family.

I started downstairs to answer the door, but my Mom got there first. "Karen", she called, "there's somebody here to see you!" I knew Penny was coming over to play, so I wasn't surprised. I wasn't surprised until I got a look at her.

The plain little girl I went to the mall with was gone. In her place was a glamorous, naughty little Lolita. Her legs shimmered in sheer nylons. Her makeup was a little amateurish, but flattering, especially the bright red lipstick and the deep rose blush. She had on a short skirt, but the real stunner was her tiny cut-off T-shirt. It barely covered her tits if she didn't breath too hard, but even then her nipples stuck through the flimsy material. It was perfect to show off her nipple ring, and anyway it had a tendency to pop-up and get caught on top of her titties. Across the front it said "AngelTeen".

Penny was wearing high heels, but she obviously wasn't used to them because of the way she teetered on the three inch spikes. "Wow, Penny, you look SO kewl! Where'd you get those shoes?"

"My Daddy bought them for me to say thanks for the choke collar. He wants you to have a pair too."

She handed me the package. Just like Penny, I've never worn high heels before, but when I opened up the box I caught my breath at how beautiful they were. Mr. Lovelace had bought me a pair of open-toe spikes which had a little gold ankle strap to hold them on.

I had been going barefoot most of the time I was naked, but I didn't really like it because it hurt my feet every time I stepped on a pebble, plus I don't like having dirty feet. The program at school encouraged complete nudity, but allowed shoes, and would make an exception if you wore something that made you look even sexier. I slipped them on and stood up. A little wobbly, maybe, but feeling very grown up and glamorous. I looked in my full length mirror, and was delighted with the way they made me stand. My bottom stuck out in back, my tits in front, and my legs looked much longer and more curvy. I decided I was going to wear them everywhere, even if they did hurt my feet.

"Wow, Penny, thanks! Your Daddy sounds great, but I never thought your Mom would let you dress like that. You rock, girl!"

She smiled and dimpled. "Lot's of things have changed at my house since Daddy started making Momma wear the choke collar you got her. She didn't like it much at first, but every time she got bitchy Daddy just tightened it up until she did whatever he wants. This is the first time I've ever seen Momma wear a short skirt and go without a bra.

"In fact, I hardly see Momma and Daddy all day, but I sure hear them. They shout nasty things from the bedroom, and I can hear her all over the house. Even out in the yard!" Penny seemed embarrassed, but I could see a twinkle in her eye when she talked about her noisy parents.

"Cool! I love that little T-shirt. It goes perfect with your nipple ring."

"Thanks," she said. "Karen, I can't thank you enough for helping me grow up and enjoy the program. My Girl Scout troop is starting a nudity project next week. We're going to have merit badges for going topless and for full nudity, and maybe even for sex. We'd love it if you'd come to our meeting and help us get going." I've never been in Girl Scouts, but I liked the idea of helping other girls learn to enjoy going naked, so I told her I'd think about it.

She walked over to me. "Look how hard my nipples get now when you play with them." Just as I reached up and touched her nipple, the door opened and in walked my kid brother Jimmy!

I grabbed back my fingers but I think Jimmy saw what we were doing. "Uh, Penny...", I stammered, "This is my brother Jimmy. Jimmy, you know all about Penny. Jimmy has been asking to meet you ever since he heard you were in the G.E.P." Penny's eyes lit up when she heard another boy had been talking about her.

"Hi, Jimmy. Pleased to meet you", she said.

"Hello, Penny", Jimmy said, trying not to stare at her titty ring, obviously embarrassed because I told Penny he wanted to meet her. I felt a little bad, but that's what he gets for walking in just as Penny and I were starting to play.

Jimmy pulled out a small box wrapped up in red paper and a big bow. "Karen told me you might be coming over. Here. It's just something...", he stammered, "I saw it at the mall and I thought about you". He handed the box to Penny. She smiled at him and tore off the wrapping paper.

"I heard all about your nipple ring. These were for sale at a stand in the middle of the mall. This one isn't as fancy as the one that man gave you last week, but I kind of thought you might like a little variety".

Penny was staring at the little wire with a small stud on one end and a silver pixy charm on the other. She held the box in her open palm and looked at it with fascination. Then she glanced up and shyly looked Jimmy in his eye. "This is the nicest present I've ever gotten from a boy". I thought that it was probably the first present she'd ever gotten just for being a girl, but I didn't say anything.

"Jimmy, would you like to put it in me?", Penny asked, pulling up her T-shirt. The diamond that Mr. Williamson bought her last week sparkled from the gold ring in her left tit. Jimmy blushed bright red and nodded. Penny handed the box back to Jimmy. Then she undid the latch and slid the ring out of her nipple. "Be careful, my titty is still a little sore from last week."

Jimmy took the bar and unscrewed the stud. As his fingers touched her nipple, Penny gave a little grimace of pain. Jimmy pulled his fingers away as if he'd burned them. Penny turned sorrowful. Then she looked back in his eye and said, "Maybe you should kiss it and make it better."

Jimmy looked awe-struck. "Gee, Penny, can I really?"

"Of course you can, silly. Come here." She took his head in her hands and pulled him down to her little boob. Jimmy gave it a lick, then a kiss. Then he opened his lips and sucked it into his mouth. Penny grimaced again, but this time she cuddled his head in her hands as he gently sucked her nipple. Suddenly she gave a start of surprise as his gentle sucking gave way to a sharp bite!

Jimmy gave her tit a final lick, then took it between thumb and forefinger. Penny gave out a yelp, but Jimmy pinched tighter and pulled her tit painfully toward him. "Quiet!", he said commandingly, "If you want a present, stand still while I give it to you."

Penny looked startled, but she stood still and bit her lip while my brother stuck the wire through the tiny hole in her tit, pushing the pixie tight up against it and screwing the stud in place on the other side. The tiny silver pixie was tilted so she seemed to hover over Penny's tit, just touching it with the tip of her wand. Jimmy gave it a sharp twist. A tear ran down Penny's face, but she didn't make a sound. "There," he said, and kissed her.

I've never seen this side of my little brother before. He was treating her like the boys did when they gang banged me. I'd never seen this side of Penny before either. She liked it. She opened her mouth and let Jimmy stick his tongue in.

When they finally broke the kiss, I spoke up. "Penny, have you seen a naked boy up close yet?", I asked.

She blushed again. "No, at least I've never seen a hard penis."

"Not 'penis', silly, boys like us to call it a cock, or a dick. Just like you have a pussy, not a vagina. Right, Jimmy?" He smirked and nodded.

Penny giggled. "Last week my Momma would have washed my mouth out for saying words like that, but this week she's the one who's been yelling them. I even heard her say 'fuck'!" She blushed a little with the thrill of saying the forbidden word, and her sore nipple hardened beneath the hovering pixie.

"Jimmy, I think you should show Penny what she's been missing."

Penny and I saw the bulge in Jimmy's pants the moment he walked into the room. I stepped over to him and took his hard-on in my hand. My 'little' brother was surprisingly big, and I felt it swell even more in my hand.

"Here, Penny, do you want to feel it?"

"Only if Jimmy tells me to", she said shyly.

Both of us looked at him. Jimmy gave us a smirk and nodded arrogantly. "Get on your knees and you'll get a really good look."

Penny was staring at my hand on Jimmy's hard cock. I let go as she slowly came closer and stopped in front of him. He put his hand on her shoulders and shoved her roughly to her knees. Now she was staring at the outline of it bulging out through his jeans. She looked a little frightened. Jimmy surprised me again by grabbing her hair and demanding "Unzip my pants." Penny looked up at his face, then back down at his dick. A bit reluctantly she reached for his belt buckle and unfastened it, then tugged down his zipper. She began to fumble with the button.

Jimmy looked impatient. "Hurry up, silly bitch," he said, and reached down to help her.

Things were going too fast for Penny. The button snapped apart and Jimmy's hard prick popped out and bonked her forehead. She went cross-eyed trying to focus on the dick in her face, then she fell backward, startled, catching herself on her hands. Jimmy reached down, grabbed another handful of her hair, and yanked her back to her knees, pressing his dick against her face.

"Ewww," she said, suddenly confronted by her first hard cock. Even though Jimmy was a year younger than her, it was still an intimidating sight for a girl who had recently been traumatized by her own nudity. Suddenly the tart was gone, and the frightened little girl was back. Her eyes closed tightly as Jimmy rubbed his dick over her face, leaving hairline tracks of pre-cum from her forehead to her chin until he smeared them across her face with the next pass of his dick. She was trembling now and moaning with fright, but at least she didn't try to fight him.

I knew she needed help, so I moved around behind her and dropped to my knees, taking her shoulders in my hands. "Hey", I whispered, "It's all right. Jimmy isn't going to hurt you. He's just doing what boys do to girls. You made him think you were going to suck his dick, and now he thinks you're just a cock-tease." Some of her trembling eased, and I reached around and gently cupped her small titties. Her shoulder length blonde hair caressed my bare nipples as I hugged her from behind. "You're not a cock-tease, are you Penny?"

"Noooooo," she moaned through clenched teeth.

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