Friday and my date with Cindy came quickly. I was busy with my work, and my savings stash was doing well. I pulled some money out of it, in case I was paying. Cindy had said she was managing it, but that wasn’t how things worked — the guy pays, right? I also grabbed a few condoms and put them in my pocket, just in case. I doubted anything would come of it, but if it did and I didn’t have condoms? That’d really suck.
I was waiting on the porch when Cindy pulled up, and so was the rest of my family. She bounced out of her mom’s Ford Fairlane station wagon. It was blue with a faux wood paneling strip that was peeling off. “I know,” she said as she walked up. “The car is older than either of us, but it runs and Dad says it’s safe, so I can drive it.”
“It’s more car than I have,” I said. “For now, at least.” Cindy had put her hair up in a ponytail, which was better than the big hair girls were wearing down in North Carolina. She wore a t-shirt that hugged her breasts, a peach skirt that came down to mid thigh, and some cute tennis shoes. “Cindy, this is my mom and dad, and my brat sister, Amy”.
“I am not a brat!” Amy said, and went inside in a huff, slamming the door as she went.
Dad just shook his head at me and Mom glared. “Be nice, Brian.”
“I just didn’t want her doing what she did last time.”
“You’re both older now,” she said.”
Cindy broke in, “Hello Mr. and Mrs. Erhard. I’m Cindy King.” She shook Mom’s hand.
“I met your mother,” Mom said. “Pleased to meet you as well.”
“I believe,” Dad said, “that this is the part where I threaten you with bodily harm if you hurt my child in any way—”
“Dad!” I said.
“But I think you’ll be okay. What are you plans for tonight?”
“Dinner and a movie,” Cindy said. “We’ll be home by 10:30, I’ve got to be back home by 11 myself.”
“Very well,” Dad said. He patted me on the back, “Brian, don’t do anything I wouldn’t do,”
“Yes, sir,” I said, and escaped into the car with Cindy. The Ford Fairlane was an old style car— and therefore had bench seats instead of bucket seats like my parent’s cars.
“Seat belt, condom boy,” she said. “Mandatory here now, and my Mom will kill me if we die in a crash. Her words exactly.”
“Okay,” I said, pulling it on. ” You don’t have to call me that, you know.”
“I’m going to keep calling you that until you tell me why you need so many condoms.”
“The usual reason,” I said. “Stand-up comedy.”
“I’m serious, I want to know.” She said.
“It’s not for me to say.”
“I plan on using my feminine wiles on you to find out.”
“If you want, you can be the reason I need so many condoms,” I said waggling my eyebrows outrageously. “Ever think of that?”
“Yes, and it ain’t happening until you tell me your secret, Condom Boy. See. Feminine wiles.”
“I guess ‘Condom Boy’ it is. What’s for dinner, and what movie?”
“Have you seen Star Trek V?”
“Yes,” I said. “Please tell me that’s not what we’re seeing.”
“As far as my Mom is concerned it is. I saw it a couple of weeks ago with friends. So if she asks, tell her all about it.”
“That’s fine…” I said. “So what’s for dinner/”
“Have you been to Lacey’s Olde Time Burgers yet?”
“You’ll like this. Plus the outfits are skimpy.”
“You like that sort of thing?”
“Not particularly, but boys do. You are a boy, right? I mean, I figured what with the condoms and all. Personally, I go for the burgers.”
Olde Time Burgers turned out to be a drive in. The waitresses wore short skirts and pillbox hats as they skated back and forth with our meal. I watched them, and it was nice, but once you’ve seen and held the real thing, it’s easy not to drool over a tease. Cindy was right about one thing, though: the burgers were good.
As we sipped the remains of our malted shakes, I asked her. “If we’re not going to see Star Trek V — what are we going to see?”
“I figured we’d go somewhere and talk or something,” she said.
“Or something,” I said. She nodded and blushed. I looked at her really well for the first time. She was attractive, and while her breasts were no match for Janet’s, she was still curvy and nice looking. Part of me wanted her, and wondered if I could have her. I certainly didn’t know her well enough to be friends or even be in love, yet we were obviously going off somewhere private. “What do your parents think about you going off somewhere to do something with a guy who you sell condoms to enough to nickname him ‘Condom Boy’?”
“That is most emphatically not on the list of things they know or need to know,” she said. “They think I’m going out with the nice boy who mows the lawn.”
“Only you know better,” I said.
“I hope so,” she said, and put the car in gear. “Ready to blow this popsicle stand?”
“I’m just here for the ride,” I said. She laughed and began driving.
We didn’t actually live in Cleveland, but in a suburb to the east of it. To our north was Lake Erie, and to the south middle of nowhere Ohio. Cindy pulled onto a state highway and began driving south until we were in rural America. It didn’t take long — that was one thing North Carolina and Ohio seemed to have in common. Soon she pulled off into a dirt road that went back into a clearing with a bit of woods. “My cousin owns this place,” she said. “But he’s in the military, serving in Japan right now.”
She pulled into a shady spot, turned off the car, and put it in park. “You can take off the seat belt now,” she said, undoing her own. She turned on the radio to a local station, and Guns N’ Roses started playing. She scooched a little closer on her bench seat, and so did I.
I reached out for her and caressed her cheek. “Did you learn anything using all those condoms?” she asked.
“When to keep my mouth shut,” I said. But that had been obvious, I could never tell anyone about Janet. She would get in trouble, and the sex would go away.
“Other than that,” she said.
“I learned when was a good time to open my mouth, too,” I said. I leaned in and kissed her on the lips, feeling the softness of them. I kissed her again, sliding my hand into her hair, and pulling her close to me. I wanted to take control of that moment, and so I kissed her again as I held her head in my hand. She moaned, parting her lips, and I slid my tongue between them.
She pushed against me then, and our tongues found each other, she moaned into the kiss, and we did just that for a few minutes. Kissing and probing, and feeling each other out. She wasn’t Janet, that was certain. Janet knew what she was doing, and how to kiss. That and we never spent that long on it — we were ready for breasts and cock and fucking a lot faster. I had no idea how far Cindy would go.
Even as I thought of Janet, I thought about what she’d taught me, that the first rule was to be where you were, with whom you were with. I put her out of my mind and focused more on Cindy who was getting hotter and kissing more passionately than Janet ever did. I slid my other hand down her side, to her hips, then back up again. I reached for her breast, cupping it in my hand, and she broke the kiss.
“I don’t know if you brought condoms,” she said.
“It won’t matter,” she said. “We won’t need them today, understand?”
“There’s a lot of other stuff we can do,” I said. A lot of things I’d never done with Janet, but I had more experience than Cindy, that was certain.
“I was hoping you’d say that,” she said. My hand was still on her breast, and she put her hand over it, and squeezed. I slid my other hand down over her other breast and squeezed it too. It was a bit awkward, sitting on a bench seat in her car, but I managed. I kissed her again, and she leaned into me. I felt her breasts through her clothes, then slid one hand down to her waist, pulling at her blouse.
“Wait,” she said, pulling away. She slid over to the driver’s seat.
“I’m sorry,” I said to her. “If that was too far—”
“I said wait,” she said. She opened the door and went outside. Next thing i knew, she had opened up the rear hatch. “This is a station wagon,” She said. “I have blankets.”
I got out of the car and met her in the back. The Fairlane didn’t have the biggest cargo area, although it had places to sit there, too. Those were folded up, and Cindy pulled a latch that folded down the rear seat, giving us more room. I spread out blankets, and lay down. Cindy lay with me, pulling the hatch closed in the process. “Where were we?” she asked.
“I was pulling off your shirt so I can see your boobs,” I said.
“Oh, right,” She said. She grabbed the hem of her blouse, and pulled it up over her head, and off. She was wearing a red lacy bra that hinted at her breasts beneath. Her nipples were hard, and poked through the sheer fabric. “Better?” she asked.
“Much,” I said.
I put my head between her breasts, and kissed them. I slid my hands up her sides, grabbing the underwire of her bra, and pushing it up over her breasts. As I did, I moved over to her left nipple and wrapped my lips around it, and began to tease it and suck on it. I paid attention to how she responded, adjusting what I did based on her gasps and moans and more specific encouragement. I moved to switch to the other breast and she used the opportunity to pull off the bra.
“Not much experience taking off bras?” she asked.
“No,” I said. “Maybe you could teach me that.”
“Another night,” she said. “I’m not putting it back on for you to practice.” She pulled my head into her right breasts, and I started licking and sucking on that one. Time to push a little harder, see how far she’d let me go. Maybe that was aggressive of me, but I’d never been the aggressor with Janet. That had been her job. I wanted to conquer Cindy, even if she was particularly willing. It still felt good; manly. My cock was hard, pressing against my jeans. Yet I knew if I took it out, that’d be as far as we got tonight. She’d been clear about that line and how we weren’t crossing it.
I slid my hand to her bare thigh, and started pushing her skirt up. Her panties were short; not thongs, but still small, lacy things. I suspected they matched the bra. It didn’t matter. Her nipple was hard between my lips, and her ass was in my hand. Cindy moaned and writhed in my arms, and wrapped her hands around my head pulling me into her breasts.
While I was enjoying myself, I wasn’t happy with what she was doing. I wanted to be more in charge, I guess. I didn’t know about dominance and submission then, or even my own leanings. But they were there, I can see that now, in that first time — in all the times — with Cindy. I pushed a bit on her, and rolled her on her back. I slid my hand so that her skirt was up, exposing her panties, and I slid my knee so it was between her legs.
She was practically naked, but I was fully clothed. That was fine for now. I pulled myself off her breasts, and kissed her again. She opened her mouth and our tongues touched each other. I took her arms in my left hand and lifted them over her head. “I bet you want to come,” I said.
“Yes,” she said, her hips ground against my leg.
“I’m going to make you come,” I said. “Any boys do that for you before?” She shook her head. I smiled. “So I get to be first.”
“This is something learned, on those days I used up a box of condoms,” I said. She tensed beneath me. “Before we got to using them, though.”
I kissed her again, and slid my right hand up the inside of her thigh. I moved her panties out of the way (they did match, after all) and slid my hand against her pussy. She was incredibly wet. I told her so, and she blushed. I moved my fingers against her, watching her face for every sign as I did so. I didn’t press inside her, I just parted her lips with my index and ring finger, and slid my middle finger between them, feeling for her clit.
She gasped when I touched it, a sound of surprise and lust. She was flushed with excitement, and I still held her down. “I could let you go,” I said, teasing her clit with my middle finger. “We could put our clothes back on. Well, you could put yours on. I’m still fully dressed. We could go home.
“N-no. No,” she said.”Please, please make me come.”
“Since you asked so nicely,” I said. I played with her then. I teased her clit off and on, slowly at first and then building speed. I kissed her cheek, and licked it. I teased her nipples with my tongue. All the while I kept rubbing her clit. She squirmed beneath me as her arousal grew. I just kept on. “Give it to me,” I said. “Come for me.”
Her back arched, and she let out a squeal that was deafening inside the car. I kept rubbing until she rocked side to side, trying to dislodge me. “Enough, enough,” she gasped. I slid my hand away, and rolled over to lie next to her. “Wow,” she said. “That was the first orgasm anyone else ever gave me. Thank you.”
“You’re welcome,” I said. “My pleasure.” I undid my pants and pulled my cock out through my underwear. I was painfully hard. “As you can see.”
“Oh, yes,” Cindy said. “Give me a second. I have some experience with that.”
“Yeah, old boyfriend. It kept him from pawing at me. If I’d known pawing could feel that good, I might have let him. But then he didn’t have special practice, like you, Condom Boy.” While she spoke, she got up on her knees and turned around so her head was near my crotch. Her pussy was near my head, and I could smell her arousal and come on her. Her breasts swung below her, and I just watched, enjoying the fruits of my labor.
Then she slid her lips over my cock, and began to suck me off. Unlike Janet, she never swallowed me whole, but she jerked me off and sucked me at the same time. I was pretty hot and bothered, and it felt really good. It wasn’t long before I said,“I’m really close.” She pulled off of me and smiled, and slid down a bit so her tits were right over my cock.
“I’m going to jerk you off onto my tits,” she said. “Then I’m going to let it dry and go home that way. My Mom and Dad are going to see me with your cum all over me.”
“Did you do that for your boyfriend?”
“I only do this for guys who give me mind blowing orgasms,” she said. She leaned forward and I could feel her tits next to my cock and her hand quickly jerked back and forth. The idea of her father seeing it, her mother.. It was enough to throw me over the edge. I spurted onto her breasts, and then she turned to me and rubbed it all in.
My cock stayed hard, even though I knew that was probably the end of our night. “You like that CB?” she asked. “You like your come all over my tits?”
“CB?” I asked.
“Condom Boy,” she said.”It’s just too long for normal use. Plus it raises questions.”
“You could call me Brian, it’s my name.”
“Sure thing, CB.”
We talked a bit then, about Ohio and North Carolina. About being teenagers and high school. I stayed with my cock out, and she had out her tits, and it was perfectly fine, almost normal. My hard-on eventually went away, which if you’d asked me before then that I could be around a hot topless girl (much less covered in my cum) and not have a hard-on, I’d have called you a liar.
Cindy eventually patted her tits, declared them dry and got dressed. I tucked myself back in and zipped up. We folded the backseat up together, and climbed into the car and headed home. “My family is doing a big cookout on July 4th,” I said. “I’d like it if you’d come.” It wasn’t like I could ask Janet.
“I’d like that,” she said. “I look forward to seeing what other things you’ve learned from the mysterious older woman.”
“That’s hardly a guess,” I said. “You know I’ve been with an older woman. You.”
“She’s got her own place,” Cindy said. “She has to. I bet she’s even often naked by the time you get to her. Or you’d know how to take off bras.”
“Those are interesting guesses,” I said. “You owe me some practice with the bra thing. And some tips for pulling it off.”
“Well, I work for orgasms,” she said.
“Me too,” I said. It was getting dark, and I was glad she didn’t see my frown. It wouldn’t be hard for her to figure out who Janet was. How many older women did I know, really? Still, Cindy seemed cool, and she was my age.
I might have to keep my distance from her just in case she figured too much out. Well, July 4th was fixed, and all the things I didn’t know that would flow from that. I guess I’m lucky that Cindy turned out to be as remarkable as she was. Because I was no good judge of character at the age of fifteen, as I was soon to learn.