A Week with Cathy Ch. 07

This story takes place more-or-less simultaneously with Chapter 6.

GAIL

"Okay," I said, "so the Cathy-and-Howie-in-your-pool story you were teasing us with the other night?" Vicki and I were in her car, driving to a museum about 45 minutes upstate. My aunt and my parents were meeting us there, but five people in my aunt's small car would have been a bit tight.

"Okay, well, this was a few years ago, Howie was your cousin's first boyfriend, and the three of us were hanging out in the pool. They were getting a bit touchy-feely, nothing that bad. Then I had to go pee and while I was up there I looked down at them from the window and they were really going at it. Kissing, groping... I probably stood there and watched for longer than I should have. Then I figured I'd better get down there before things got really out of control and by the time I did her bikini top was pushed up to her neck, he had his hands on both of her breasts, and maybe I shouldn't tell you this part..."

"Tell me."

"She was all flushed, she was catching her breath. I couldn't tell whether she was really turned on or, you know," she lowered her voice a bit, "he made her cum. Her nipples were all hard, I'd never seem them like that before. Anyway... she fixed herself as soon as she saw me, tried to act all innocent, and all she told me the next day was this had been the first time she'd let a boy see or touch her breasts."

Of course I had seen Cathy cum."Oh, the stories your swimming pool could tell," I said.

"Speaking of which, tell me the truth, Gail... when the four of us were swimming the other night, and Cathy and I were topless, if Scotty hadn't been there, would you have taken off your bra?"

I thought about it for just a moment before saying "Sure, I'm sure I would have."

"And at the party last night, same thing, if Scotty hadn't been there?"

"Definitely. Do you want the truth?"

"Of course," she said.

"I was tempted to anyway," I said in a near-whisper, even though we were alone in the car.

"Oooh, naughty."

"Same question," I said. "Last night, if your brother hadn't been there."

She hesitated for a moment, and I didn't find out why until a lot later. "The same. I would have, and I was tempted to do it even with him there."

We were both silent for a minute or so, lost in thought. Then she said "Okay, your turn again."

"Okay."

"Have you ever let Scotty see you topless, or worse? On purpose?"

Now I was the one hesitating: what Scotty and I had done last night was certainly a game-changer. "You know, I think I'd better take the Fifth on that one."

"Oh, now I'm intrigued."

Bad move on my part: I should have just lied, but I'm really no good at it.

"Well," she went on, "you have to take of your t-shirt then."

"I what now?"

"You don't answer the question, you have to do a dare."

"Who said we were playing Truth of Dare?" I asked.

"Who said we weren't?"

"Okay, you know what, screw it," I said, pulling the shirt over my head and placing it in my lap. After all, I was wearing a dark blue bra, larger than many of my swim tops (let alone last night's).

"Whoo-hoo," Vicki said, though obviously this wasn't any big deal. "At least this one's opaque," she added.

"It's what now?"

"The bra you were wearing in the pool the other night was almost see-through, and when it was wet it wasn't hiding a thing."

"Um..."

"Shit, you didn't realize?"

"Ohmygod..."

She laughed. "I thought you knew."

So... Scotty was able to see my boobs all along. So... at that point I might as well have taken off my bra. I still wouldn't have rubbed myself against Scotty the way Vicki and Cathy did, obviously, but I would have been a lot more comfortable. Though I wonder whether the girls would have still jerked him off if I'd been in the pool with them.

Last night... God, I'd wanted to take off my top when some of the other girls had, and if I'd been topless the first night, there would have been no reason not to. I might have had half a dozen boys touching my naked breasts before the night was through. I shivered at the thought.

"Are you okay there, Gail?"

"Yeah, I was just... yeah, I'm okay."

She nodded, then switched on the radio. A few miles passed, then I realized she'd ended the "game" a bit abruptly. Suspiciously abruptly.

I reached over and turned off the radio. "Same question," I said. "Did you ever let your brother Barry see you topless, not by accident?"

She sighed, and without a word pulled off her own t-shirt, veering a bit but fortunately not driving us off the road. She was wearing a bra, but it was far less substantial than mine, barely coming up above her nipples, almost completely exposing the rose tattoo on her breast.

"You and Barry were going at it pretty good last night," she said, before I could comment on what she was wearing.

"Was that a question?" I asked.

"No," she said. "Just an observation. I had a feeling if his prissy little girlfriend hadn't shown up, he would have gotten you up to his bedroom. Okay, let's call that my question. Taking the Fifth again?"

"No, you're right," I admitted. "I totally would have fucked him if he'd asked. Especially if I'd already been topless in the pool."

"You slut," Vicki said with a grin.

"And I still might," I said. I wasn't sure whether that was true, but I was enjoying talking like a bad girl. "Were you really about to fuck Scotty in the pool that first night if your parents hadn't come back?" I asked.

"Oh, yeah. He already had my panties partway off, and from there he could have done anything he wanted. "

And with that, we drove most of the rest of the way in silence. I'm pretty sure Vicki was thinking impure thoughts about my brother, and I was certainly thinking impure thoughts about hers. I was definitely in the car with the wrong Conway sibling: if I'd been driving with Barry, my bra would have been on my lap along with my shirt; and if that didn't put a thought in his head to pull over to the side of the road, I'd have suggested it myself.

BARRY

Anna had her arms crossed tightly across her chest as I drove. I was driving my mother's car (because she decided to pay hooky from work today), headed for Anna's parents' lake house downstate. They'd gone ahead the previous day, but we didn't want to miss my sister Vicki's pool party last night.

Ah, that pool party... several girls had taken off their tops, which had never happened at any our pool parties before, there was a lot of groping going on, and I'm pretty sure one couple huddled in the far end of the pool was actually fucking.

Anna had barely spoken a word to me since I'd picked her up this morning. Clearly she was angry about last night.

She'd hinted that we might do some serious fooling around while we were at the lake house: she wasn't sure about actually having sex, but she knew a secluded spot where she'd always wanted to sunbathe topless, and she definitely wanted me to be with her. So at the very least, I'd finally see her breasts.

I'd been hoping to start the fun even earlier: when I picked her up, nobody else would be home, the first time we'd ever been completely alone in her house. We could go up to her room, make out on her bed, maybe I could get her out of her shirt, and from there...

Well, clearly that was not to be: she climbed right into the car, and her breasts were now covered by a bra, a shirt, and her crossed arms.

Once I saw she was angry, I was afraid to say anything: what if her BFF Penny had told her I'd had my hands on Cathy's cousin Gail's ass?

(For that matter, would it be awkward hanging out with Penny, after seeing her wearing nothing but tiny bikini panties?)

"Last night..." she finally said.

"Yes?"

"Did you want me to take off my top like those other girls?"

Did not see that question coming... "Um... if you wanted to, I guess?"

"No," she shouted. "You wanted all our friends to see your girlfriend's breasts?"

"Then no," I said, desperately. "Anna, just tell me which answer won't get you angry."

Well, that wasn't it. Silence for few more miles.

Then: "Did you like Penny's tits? You had a pretty close-up look."

Yeah, I did, but only because Anna had accidentally pulled off Penny's top -- but I wasn't going to mention that.

"Ellen, Zoey," she continued. "And oh, Tony's step-sisters: they just whipped off their tops before even saying hello." And by the end of the night, Cathy and JoAnne and Gail's tops were barely covering anything. But I thought better of mentioning that too.

Out of the corner of my eye, I could see Anna fingering the bottom of her t-shirt as she thought. "You know," she finally said, "maybe it wouldn't have been such a big deal if I'd taken off my top too."

"It would have been a big deal to me," I told her.

I could see I'd finally said something she liked.

"Well," she said, "I'd still be embarrassed to do it in front of all our friends, but... pull into the next little road we pass."

I did. It was a road that probably led somewhere, but I couldn't imagine where.

We were barely out of sight of the main road when I noticed her t-shirt was off and lying in her lap.

I stopped the car. I'd seen her in a bra before, but never one this sheer. "It's new," she said shyly.

"I love it. May I?"

"Yes," she said.

I reached over and lightly stroked both nipples, which were clearly visible and poking through the thin cups of the bra.

"I like this," she said softly. And then a couple of minutes later "Hang on for a second," and when I took my hands away, she unclasped her bra and dropped it onto her lap along with her t-shirt.

I spent the next ten minutes doing many of the things I'd always dreamed of doing to Anna's breasts and when she put her shirt back on and we drove back to the main road, she reminded me that there were a lot of places both in and around her family's vacation place where we could have complete privacy.

TONY

"So we were thinking," Sara said.

"Always dangerous," I told her.

We were just pulling out of the airport parking lot, having dropped off my father and their mother.

"While our parents are gone," she continued, "when we tan on the back deck, we're going to do it topless. You may have noticed last night how shockingly white our boobs were, and this will be our last chance to even things out before school starts."

"I wasn't looking at your.. boobs," I told her.

My step-sisters and I grew up on different planets: though we're all athletes of various sorts, they're a lot more open and social, and I'm kind of shy. So of course ever since our parents married a year earlier, they made it their mission to tease and try to shock me.

Nothing really outrageous, mostly making off-color comments in my presence or occasionally walking around upstairs in lingerie our parents wouldn't have approved of. It must have been fun having a brother who had trouble saying "boobs" out loud.

"We figured as long as you've already seen them," Kara added.

Last night was the first time I'd seen the girls actually topless, though some of their lingerie didn't really hide much. I wouldn't give them the satisfaction of saying anything, but of course it was sometimes frustrating seeing them dressed like that: both of them my sisters, and Kara being gay. "Though maybe you didn't have a chance to really see: I saw Cathy's cousin come up to you right away. Did she really do what I think she did?"

"Um... I guess so."

"What did she do?" Sara asked her, though I'm sure they'd discussed this already.

"It looked like she introduced herself and then started stroking Tony's dick. Is that what happened, Tony? Did she stroke your dick? Huh?"

"Yes, she stroked... yes she did. But a lot of girls were doing that last night."

"He's right," Sara said. "I touched a few dicks myself. And I had a few guys touch my boobs. Pretty hot stuff. I had half a mind to take off my bikini bottoms as well."

"You did not," Kara told her.

"Well, maybe if somebody else did first. So tell me, what happened after Cathy's cousin started stroking Tony's dick? I was too far away to see."

"Do we really need to do this?" I asked, though I should have known better than to react at all.

"I'm not really sure," Kara said, "but it looked like she put her hand down the front of his suit and grabbed his actual dick. Is that what actually happened, Tony? Did she grab your bare dick?"

I nodded.

"And did she really start to jerk you off?"

"Kara..." I said.

"I didn't mean to watch, really I didn't, but she was cute as fuck. I would have loved to have her hand down the front of my suit. I totally would have taken off my bottoms to make it easier for her to finger-fuck me."

"I can just imagine that," Sara said.

"And you did a nice job playing with her tits," Kara said to me. "You managed to get her top hanging so loose on her, it wasn't covering a thing. So thanks for that."

"Um... you're welcome?"

"And did she really make you cum right there in the pool? She did, didn't you?"

"So you finally got to see a guy cum," Sara teased.

"First time a girl's touched your dick?" Kara asked me.

"Do I have no semblance of privacy left?" I asked her.

She shared a glance at her twin. "Of course not, don't be silly," they both said. And Sara added "You have sisters now, don't you know how that works?"

"And we're so glad you're okay with us sunbathing topless," Kara said.

"I'm not really," I said.

"That's so nice of you," Sara said, deliberately ignoring me. "Hey, maybe we'll invite some friends over to join us. You'd like that, wouldn't you?"

"Bullshit you will," I said.

"You're right," Kara said, "but... introduce me to Cathy's cousin, and maybe we can work something out."