My Naive Fiancé Goes to Prom

I realized I was being ridiculous. I didn't want to see my sister naked after all, except for mere curiosity. I should just be happy that the confident girl I knew was finally coming back.

"And then you guys sped your way to the ferry," I said.

"Yeah, though, Annie and I were having some issues," he said.

"What do you mean?" I asked.

"Well, once we got on the road, everyone pretty much fell asleep immediately," he said. "Except for us. Annie laid down with her head in my lap to rest, but I was still so hard from everything that had happened that morning, so she couldn't get comfortable. At first she tried to just lay with her head against it, but I guess it's tough to sleep when a boner keeps poking you in the cheek. So then she sat up and asked me if I wanted her to take care of it. I thought she was joking, but then she just slipped her little hand down the front of my shorts and grabbed my naked dick!"

"Right in front of everyone?!" I gasped. I was glad she was getting her confidence back, but she was getting a little too bold if you asked me.

"Yeah," he said. "Well, kinda. We were in the backseat, and everyone else was asleep except for Julia, who was driving. We were whispering so she couldn't hear, but yeah, basically right in front of everyone. She started jacking me off inside my shorts. I was aching so bad and it felt so good. I started leaking so much precum that my dick got completely soaked as her soft little hand stroked it up and down.

"I told her that I was happy to be her pretend boyfriend for the weekend and that we'd had to push some boundaries, but her making me cum was too far. Apart from being a decade older than her, I was engaged to her sister! She insisted that since we'd seen each other naked and I'd already made her cum on the dancefloor last night, that we weren't going any farther than we'd already gone. Plus, I was her future brother-in-law and she could tell she'd caused me a bunch of pain by teasing me so much without relief. She worried that my balls would explode if she didn't empty them soon, and she'd be a terrible sister if you let her borrow me and she broke me. I said I still didn't want to cum and she couldn't make me. And she sorta took that as a challenge."

"What do you mean?" I asked. I was glad my sister wanted to relieve his pain, but I was on his side for this one.

"Well, we were in the van with everyone else, so she couldn't do much," he said. "She tried to jack me off harder, but with our clothes and seatbelts on, she couldn't get much leverage. She rubbed her boobs against my arm, but that didn't really do much either. So then she just started whispering really dirty things into my ear."

"Like what?"

"I was pretty far gone and this went on for a while, so I don't really remember all of it."

"You must remember something."

"Yeah, well, uh, it was a lot of different stuff," he said. "Nothing serious, just different things she could think of that she thought might make me bust. At first it was just things like how she couldn't wait to show me her tits again and make me play with them. Then stuff like that she thought my dick felt amazing in her hand and wondered how it'd feel in other parts of her body. She was really getting my heart racing, but I was still holding on, so then she took things up a notch."

"What do you mean?" I asked.

"Promise not to get mad," he said. I stayed silent and he just continued. "She probably wasn't being serious. But she was saying stuff like 'your dick is my toy now and I get to play with it whenever I want' and 'it's going to feel so naughty when we keep doing this after you become my brother'."

"Oh my god," I said. "Where was she coming up with this stuff?"

"I have no idea," he said. "But after a while, I just couldn't take it anymore. I'd been rock hard basically since the beginning of the dance the night before and I started actually worrying my balls would fall off if I didn't give in soon. So I took a deep breath and just let it happen."

"You came?" I asked.

"Yeah," he said. "And it was a massive load because of all the buildup. I pumped rope after rope after rope of jizz all over her hand and wrist inside my shorts."

*****

CHAPTER 3

I couldn't believe it. My sister had jerked off my fiance in a car full of people. Even more unbelievable, I didn't feel like I could get upset considering all the context. Ugh, why did this always happen to me?

"Did anyone see?" I asked.

"I didn't think so at first," he said. "But then Nina kept winking at us and asking if I felt better. I feel like she must know."

I groaned. Then the ferry horn blasted to let us know we were arriving at the island. We unloaded and drove to our house on the waterfront. The house has 4 bedrooms, so I took one, and the three couples (Annie and David, Victoria and Rick, and Julia and Tommy) each took the others. That left Nina. Nina was fun, but definitely a handful. She's short, tan, curvy and spunky. She'd had a boyfriend most of the time I'd known her, but they broke up right before prom.

I told her that the living room couch pulled out into a bed, but for some reason, she insisted that she sleep on the couch in Annie and David's room instead. I pulled Annie aside later and she explained. Apparently, Annie spent so much time with Nina and her then-boyfriend after Annie's own relationship ended, everyone started calling Annie and Nina his two girlfriends. And now since Annie had a (pretend) boyfriend and Nina didn't, she wanted to return the favor. Nina had been dancing with each of the boyfriends last night and felt like a seventh wheel by the end of the dance, and Annie felt bad for her. I was glad my sister was so kind, but now, not only would my fiance be spending the night down the hall from me, he'd be trapped with two teen girls. I wasn't exactly thrilled.

Everyone wanted to go swimming ASAP, so we went to our respective rooms to change into our swimsuits. I was the first one done, of course, and was down in the lake before anyone else even came outside. Victoria and Rick came out next. Victoria's a tall, willowy redhead and the star of the volleyball team. I'm pretty sure she has a college scholarship from it. She naturally looked amazing in her floral bikini. I don't know her that well, but I do know that she's one of the most popular girls in their school. She's kind, but a bit more aloof than Annie's other friends even though she liked bossing them around from time to time. Her boyfriend Rick was clearly the star of some other athletic team based on his build, demeanor and the fact that he's with Victoria. He was always nice and friendly though.

Next came Julia and Tommy. I didn't know them as well, but Julia was also on the volleyball team, and I think she and Tommy also did theater at their school. I was definitely jealous of Julia's long brown hair, big brown eyes and megawatt smile. Her one-piece bathing suit highlighted her rocking bod. Why did my sister and all her friends have to be such knockouts? Moreover, why did I notice and care? I knew my fiance would be ogling them all day, that's why.

Annie, David and Nina were the last to come out. Annie and Nina were both in bikinis. Annie looked much less uncomfortable being around other people while wearing so little. I guess all the positive reinforcement from David last night and this morning paid off. When they got outside, I asked David to put sun lotion on my back. I conveniently "forgot" the lotion inside, so I'd have a moment to talk to him. The other girls teased Annie that I was trying to steal her boyfriend from her. If only they knew.

"What took you guys so long?" I asked.

"I guess Nina was really starved for attention because her top was off before our door was even closed," he said.

"Of course," I said, rolling my eyes.

"So Annie was immediately like, 'Excuse me, my boyfriend can see your boobs,'" he said.

"Wait, she didn't even turn around?" I asked.

"No!" he said. "She was right in front of me and facing me. Like she wanted me to see or something. Anyway, Annie complained and Nina was just like, 'Oh he doesn't care, my tits are so small, it doesn't matter.' Which is ridiculous. If I cared about big boobs, I wouldn't be engaged to you."

I knew David liked my little boobs, but that just meant he liked Nina's little ones too.

"So she was acting like it was no big deal for her to be half-naked in front of me, but it was clear it was no accident. Like, Nina pulled off her top and her pants right away so she was just left in her thong panties. And once she was practically naked, that's when she started digging through her bag, looking for her swimsuit, her big ass waving back and forth at us."

"Sheesh, Nina," I said.

"It gets worse," he said. "She brought two swimsuits with and wanted our opinion on them. And naturally, she didn't just put them on the bed and ask for our opinion. No, she took off her panties and then held one then the other in front of her naked crotch to 'show' us how they'd look on her. Annie was like, 'Nina, we can see your cooch!' and Nina was like, 'No, you can see my hair. My cooch is hidden between my thighs.' And she held her arms wide so we could see what she meant. And yeah, we couldn't literally see her labia, but she was still just standing in front of us, completely naked, asking us to inspect her crotch. It was weird."

"Right, so anyway, you got dressed," I said, eager to move this along. I knew Nina's antics were unlikely to lead anywhere with David's fake girlfriend around to put a stop to things, but I still didn't like hearing about this barely legal teen prancing around naked in front of my fiance.

"Yeah, eventually," he said. "I mean, I did right after that. Nina spanked my bare ass while I was turned around, pulling my trunks on. I thought Annie would protect me from her. Annie changed too and then we put sun lotion on each other. Thankfully, Nina put her bottoms on for that part, but of course left her top off and insisted I lotion her back and she lotion mine."

"And Annie really was fine with all this?" I asked. I couldn't imagine my shy little sister being ok with her friend clearly putting the moves on her boyfriend, fake or not. Was she too dumb to realize that's what Nina was up to?

"Yeah," he said. "She just laughed at her. I guess she was really close with Nina and her boyfriend when they were still a thing. If there comes a day where I claim to understand the minds of teenage girls, kill me because I've clearly been brainwashed by aliens or something."

I laughed. He had a point. I was a teen girl once and even I don't pretend to understand them. He finished lotioning my back and we headed outside. We spent most of the afternoon just lazing about in and out of the lake. I could feel the teens didn't love hanging around with their friend's much-older sister, so I tried to keep my distance, spending a lot of time reading on the patio. The two other couples spent plenty of time canoodling. Annie and David did a bit too. I was glad they weren't trying to keep pace with the others. They were totally the type to think they had to do everything these real couples did or risk 'outing' themselves. But it was still weird for me to watch them cuddle and kiss from time to time.

In the late afternoon, they started playing Truth or Dare, like any group of bored, horny teens. I noticed because there was a distinct increase in yelling and laughing and doing weird things, like belly flopping off the pier or yodeling out into the lake. I decided to wander down to join them.

"Truth or Dare?" Julia asked Annie as I approached.

"Hmmm, truth," she answered.

"Come on, you haven't done a dare yet," Nina whined.

"You're just going to dare me to take my top off!" Annie retorted. I wasn't surprised Nina was daring the girls to go topless. She probably just wanted an excuse to show off her boobs to everyone. No way Annie would get naked in front of them though.

"Someone has to!" Nina said. "You guys are so boring."

"Truth," Annie said.

"Ugh, fine," Nina said.

"When was the first time you and David had sex?" Julia asked.

I froze. For one thing, it was weird to hear another woman asked about having sex with my fiance. For another, I knew there was no answer. I saw her and David exchange a nervous glance.

"Come on, spit it out," Julia said.

"And make it hot," Nina added.

"Ok, um, well, it was a Saturday night," Annie said, blushing more than I'd ever seen before. "And this was when I'd been feeling really down and couldn't get out of bed. So Davey came and-"

"Boned your sadness away?" Nina interrupted.

"No, come on," Annie said.

"Wait, why was David there?" Julia asked. Annie, flustered, struggled to respond.

"We'd had a date planned," David broke in. "Just to watch a movie. And she couldn't get out of bed."

"Yeah, that was it," Annie said. "And he just came into bed and spooned me. Not to get into my pants or anything, but just to make me feel safe and loved. And that was the moment I felt so thankful to have him. I mean, it's cheesy, but it reminded me that real love was possible. And as soon as I felt that sense of true love radiating from him, my mind started thinking about how I could make him feel just as good. And then I remembered that his dick was just right behind my ass."

Her friends hooted and hollered and Annie somehow blushed an even deeper shade. I knew this was embarrassing for her, so I was glad she was getting through it. Even if "it" was a sex story about my fiance.

"I was just there to try and comfort her," David continued for her. "So I'm just holding her, trying to think of anything else I could do to cheer her up, when suddenly she starts grinding her cute little butt back into me."

"And then one thing led to another," Annie said.

"Tell us!" Nina said. "Give us the details."

"I think you can fill in the rest," Annie said.

"Ugh, I can, but I don't wanna," Nina whined.

I thought they hit a lull, so I asked if everyone was cool with pizza for dinner. They said sure and I went inside to order. I thought back and could remember a Saturday evening a few months back when Annie couldn't get out of bed. David went in to talk to her, and a little while later she emerged with him for the first time all day. Did they actually...? No, impossible. They probably just embellished a true story. Smart. When I came back out, Nina had lost her top. She must have finally gotten dared to. Her perky little tits and hard brown nipples were thrust out for everyone to see. She was in the middle of grilling David about why he wouldn't accept a dare while he struggled to keep his eyes of her naked chest. He finally relented.

"Your dare is," she said before pausing dramatically. "Make out with me for five minutes."

Her dare caused an immediate uproar. It did seem a little excessive. I was glad I wouldn't have to watch my fiance make out with some half-naked girl for five full minutes. At first, Annie insisted on just one kiss between the two of them, but then Nina started lowering the makeout length she demanded. Eventually, they agreed one just one full minute of making out. I would have stuck to my guns if he was my boyfriend. I mean, he was. My fiance, I mean. This was getting confusing. I wanted David to protest more, but his willpower was often lacking and Nina was hot, mostly naked and very eager to jump him, so I guess I should cut him some slack.

Nina went more full throttle than I expected. She straddled his lap and ground into him as they kissed. She was still only wearing bikini bottoms, and he was in his trunks, so their bare chests were pressing against each other too. Then, when we hit the 30 second mark, she grabbed his wrists and pushed them down until his hands were on her generous ass. Her bottoms were small to begin with and had really bunched up in her crack in her current position, so his hands were almost entirely on her bare cheeks. Everyone cheered when she pushed his hands down, and then again when he gave her thick ass a tentative squeeze, so he squeezed and massaged it until Julia called time.

That didn't stop Nina, though, and she kept kissing David until Annie told her to stop. She did, but didn't get up. Just settled into his lap side-saddle, still topless. He smiled cheekily as she threw her arms around his neck. Her naked tits were only a foot from his face and his hands rested on her thigh and her bare hip. I expected Annie to say something about this, but didn't. David probably did too. Why was she letting her best friend canoodle with her boyfriend like this? What was I missing?

David was next to dare someone, so he dared Rick and Victoria to make out. They're dating, so that wasn't a big deal. In the middle of it, though, Julia tried to rip Victoria's top off. Cool, calm and collected Victoria practically blew her top when she did. Nina booed her, calling her a prude, and the others booed too. Some more dares followed. Julia was dared to make out with Tommy, her boyfriend. This time Nina snuck over and tried to pull her top down, but Julia was able to escape. Then Julia dared Tommy to moon everyone, and he did.

Then it was Annie's turn to do a dare, and I braced myself. I thought she'd be dared to make out with David, and I wasn't thrilled to watch my sister make out with my fiance. But Tommy surprised me when he dared her to make out with Nina instead. My surprise continued as Nina refused to get off David's lap and further when Annie accepted that and just knelt down next to them.

They made out. Their comfort with it made it clear this wasn't the first time. Maybe my sister had more than meets the eye. Julia, Tommy, Victoria and Rick all cheered. I couldn't see David's reaction because Nina and Annie blocked my view. Nina was still topless, of course. Annie wasn't, but her bikini top wasn't doing a great job keeping her big breasts under control. I can only imagine what kind of pornographic view his front row seat afforded him.

When they started kissing, Nina had put her hand on David's chest, ostensibly for balance, but probably just to touch him more. As they approached the time limit, I noticed her hand had slipped down to his lap. Time was called and Annie stood back up. Nina sat back and we all got a clear view of her hand wrapped around David's shorts-covered boner.

"Hey, that's my boyfriend's dick you're grabbing," Annie shouted, pointing at it.

"I know," Nina said. "I didn't want to, but he made me."

"Hey, that's not true!" David protested. Nina rolled her eyes.

"Your boner's been poking my butt for a half hour now," she said. "I had to hold it in place to make sure you didn't try anything dirty while two hot chicks made out on top of you."

"You can make out on top of me," Tommy said, smiling. "I promise to behave myself unlike David." Julia play-punched him.

"It's David's turn," Victoria said. Annie turned to him and pursed her lips. I realized Nina still hadn't let go of his cock.

"I can't believe you'd get so dirty in front of my friends," Annie said to David, a huge smile on her face. "So you need to be punished. I dare you to get cleaned by Nina."

Everyone froze a moment, not sure what she meant.

"There's a shower over there," she said, pointing to our outdoor shower stall along the house. "Nina, can you please teach him a lesson?"

Nina, huge smile on her face, jumped up and helped my fiance to his feet. She then led him into the shower stall. From where we sat, down the lawn a little ways, we could only see their lower legs below the privacy barrier. Above the barrier, we could only see David's head and shoulders and the very top of Nina's head.

"Wait a second," Nina said, poking her head back out. "I can't trust a dirty boy like David here to behave and keep his hands to himself."