My Naive Fiancé Goes to Prom

This story is part of my Naive Boyfriend/Fiance series, but works as a standalone. You can read it without having read the others.

I could have submitted this story in a number of different categories, but I went with this one because the main character experiences it second-hand or as a voyeur. The story's themes also include cheating, exhibitionism, group play, first time and some light incest play.

All characters are at least 18 years of age.

*****

CHAPTER 1

I swear I wasn't as dumb as my little sister when I was her age. I worked hard to make sure I was never in a stupid situation like Annie is now. And who had to bail her out again? That's right, her older sister. Me.

See, Annie is about to graduate high school. Tonight is the night of her Senior Prom and, against my advice, she had dated that douchebag Jeremy most of this year. Turns out I was right, he's a scumhole, and she caught him making out with her friend Lauren a couple months ago. I was there to comfort her and dry her tears.

Ok, I'm being a bit overdramatic. Jeremy was a true abusive asshole. Mean, manipulative, the whole nine yards. My parents and I were thrilled when they finally broke up. She was a wreck afterward. Sullen, withdrawn, depressed. I remember my senior year fondly, my last big hurrah with my childhood friends. But hers was passing her by as she cried in her room. We weren't sure if she'd ever pull out of it, but then David, my fiance, came to the rescue.

The two of them had never been particularly close, and I think that lack of history made it easier for him to open her up. He and I had moved in with my parents to save money while I was in grad school, so the two of them ended up spending a lot of time together. He somehow became an expert at cheering her up. He made her smile and laugh again. It warmed my heart to come home from class and see them cuddled up together on the couch, watching a movie and making little inside jokes.

Their closeness did bug me from time to time. She clearly had a crush on him. David, bless his naive little heart, said that was impossible, but he could never see things that were right in front of his face. She was always trying to get his attention or hang out with him or cuddle him. I'd see them holding hands from time to time. I was glad she could see not all guys were cheating assholes like Jeremy and it was adorable seeing her trying to pretend to not have a crush on him. But he's my fiance! Of course my parents picked up on all this and started referring to David as Annie's boyfriend just to wind me up. All that was fine, I could deal with it. I wished she would let me cuddle with my fiance sometimes and for goodness sake wear a bra around the house more often, but none of it was that big a deal. Until her little scheme came to light.

See, at some point she came up with this brilliant lie to make Jeremy and Lauren jealous. She had a new boyfriend. One who was in college. He conveniently had to cancel last minute every time she was going to introduce him to her friends. I thought pretend boyfriends were more of a Junior High scheme.

Anyway, now it's prom, and she didn't want her pretend boyfriend to stand her up on the last big night of her high school career. So after a bunch of crying and begging on her part and plenty of lectures and disappointed sighs on mine, I'm standing here at my parents' house, getting ready to send her off to her prom with her real fake boyfriend, David.

David's older than college age, of course (28, to be specific), but he can pass well enough now that he shaved his face clean. I have to admit that they look cute together, him in his cheapest suit (have to play up his awkward teen bona fides), her in her formal gown. Not as cute as me and him, of course, but cute nonetheless.

I made Annie promise that this wasn't about making Jeremy and Lauren jealous. Life's too short for jealousy and revenge, and I want Annie to move forward. I think I had mostly gotten through to her. Not fully, judging by the dress she chose. Her figure had gone from beanpole to hourglass basically overnight and she flaunted it this evening. Her neckline plunged, showing a deep canyon of cleavage, and the dress fit tightly to her lithe form well past the flare of her hips. It showed off the bubble butt she'd gotten from spending all that time crouched on the volleyball team. Her ex had made her feel awful about her body, calling her a boy when she was thin and then fat when her chest developed. After they broke up, she only wore baggy clothes that hid her body. After David started opening her up, she began wearing normal clothes again, though was still shy about anyone looking at her. So I was glad she felt comfortable wearing something somewhat revealing.

"Keep in touch," I said as I gave David a kiss goodbye. "I wanna know how it goes and I can distract you when all the high school drama gets to be too much."

"Thanks," he said, shifting from one foot to the other. "Listen, what do I do if I, uhh...I mean, I'm supposed to be Annie's boyfriend."

"And you'll be sweet and kind to her like a good boyfriend should be," I said.

"Yes, of course," he said. "But I mean like, we're supposed to be two young lovers attending prom together. She's your sister, so I've only ever like, given her hugs and stuff. But it might seem weird if we only like, hold hands and dance like we're at Bible Camp."

I giggled. I remember how school dances were. They were faculty supervised, so you couldn't get away with much hanky panky, but most high school couples took advantage of the darkness and anonymity of a large mass of dancing teens to make out, feel each other up, etc. Caleb and Jessica supposedly even fucked on the floor of our prom, though I never believed the rumor. Regardless, David had a point. Her ex had constantly told her that no guy wanted to touch her. If she finally brought in her new boyfriend and he wouldn't touch her either? Bad news.

"You're right," I said. "I guess you'll have to be a little more, uh, intimate than that. Just remember that you're my fiance and she's my sister, which means she'll also be your sister once we get married."

"Good point," he said with a smile. "I'll try to just feel it out and make sure she seems loved and adored by her pretend boyfriend without actually, y'know...crossing any lines."

He's so considerate. I'm so lucky.

I waved goodbye as my parents drove them away. They were going to dinner with Annie's group of friends, which included her volleyball teammates Victoria, Julia and their boyfriends Rick and Tommy, along with their single friend Nina. After the dance, the seven of them were spending the rest of the night at Julia's family's house. Then tomorrow, I'd meet them at our family's lakehouse, where we would spend the day and night before returning the next morning. Somehow, Annie and her friends convinced all the parents that I was enough adult supervision for the group.

I had dinner with my parents, then we settled in to watch a movie. I pulled out my phone and texted David.

Me: [hey love, how's it going so far?]

David: [good, we're in the limo right now from dinner to the dance.]

Me: [how's life as Annie's boyfriend?]

David: [alright so far. No one has caught on yet. Julia and Victoria both gushed to Annie that I was handsome and mature, haha.]

Me: [lol]

David: [Something weird happened at dinner though.]

I could see him typing for a while, then stop, then type some more, etc. Finally, the text came through.

David: [Julia teased Annie about how much cleavage she was showing and that I must really like her boobs. Annie was just playing along and joked that yeah, I'm obsessed with them and always staring. I had been trying to avoid checking out her body since she's your sister, but I had to play along and stare at her cleavage like a horny 20 year old.]

I sighed. I obviously didn't like my fiance staring at my sister's boobs. They're bigger than mine and of course much perkier since she's so much younger. She loved bouncing around the house braless whenever David was there and my parents weren't. I reminded myself that he was probably just as uncomfortable with it as I was. I just wished he wasn't so naive that he could be talked into anything.

Me: [Ugh, that's annoying. Julia's probably just jealous of Annie's boobs, so had to make a thing of it. Sorry babe.]

He typed for a long time. A much longer time. Finally, my phone dinged.

David: [Yeah. Well that's why I had to do what I did later. During dessert, Annie dropped a bite of chocolate cake down the front of her dress and Julia said that I was probably dying to get it for her. Annie was embarrassed and said no, that we didn't do that kind of stuff. Then everyone else kinda went nuts, saying they couldn't believe that we'd been dating for months and she'd never let me touch her boobs when I was clearly so obsessed with them. Anyway, they all started chanting "GET THAT CAKE" at us. She was blushing like crazy and I didn't know what to do, but then she just turned and pushed her chest out at me. So I reached in between her boobs and scooped the cake out.]

I groaned. I'd already come to terms with the idea of them acting sweet to each other and grinding on each other all night. But they weren't even to the dance yet and her friends had already forced him to touch her boobs. I suppose they didn't really have a choice, though. As much as I wish he'd called me before diving his hand down the front of my sister's dress, any hesitation would have seemed suspicious at best and unloving at worst.

David: [Are you mad?]

Me: [I'm not thrilled, but I guess you had no choice.]

David: [Yeah. And they wanted me to lick her chest clean, but we were in the middle of a crowded restaurant. So I had to stick my hand between her boobs a few times to get it all clean.]

I guess he got to touch her big, perky breasts multiple times. I wonder how much they actually resisted. With all her complexes over her body, I doubt she wanted to have a guy feel her up in front of all her friends. But I'm no dummy. I know how amazing her breasts are and how badly any straight guy would want to touch them, even my fiance. I wonder if he just got in and out of her cleavage quickly or if he let his fingers fish around in there for as long as he could get away with. Sigh.

Me: [So where are you now?]

David: [We're about to arrive at the dance, I'll check in with you later.]

I tried to pay attention to the movie I was watching with my parents, but it was tough to focus. My fiance was across town with my sister. I had given them permission to act at least somewhat intimate on the dancefloor. He had already felt her tits (kind of). My brain kept serving me images of the two of them locked in an embrace, tongues down each others' throats, hands all over each others' bodies. Maybe they'd even find a dark corner to explore even further.

I shook my head. I was driving myself crazy. The movie finished and my parents went to bed. I texted David, asking how the dance was going. He didn't respond right away, so I prepared for bed too. When I got to my room, I noticed a missed call from him. I immediately called back.

"Hey darling, how's the dance going?" I asked.

"Hey, good!" he said. "I stepped outside for some air. Those teens are relentless!"

"What do you mean?" I asked.

"Oh, just that they're full of energy," he said. "And very persistent."

"Persistent?"

"Annie's friends are," he said. "Maybe they're just protective of her since her ex was such an ass. Like, as soon as we hit the dance floor, all the couples were grinding all up on each other. Which is fine, they're horny teens and this is a school dance. But then they noticed that me and Annie were dancing apart, so they basically bullied us into grinding on each other like they were."

Of course. Ugh.

"Which was kind of awkward at first, obviously," he went on. "Like, we talked about this before I left, but it was still weird. Like, I know her as your dorky little sister who needs rides to volleyball practice and I'm probably just her sister's dorky boyfriend to her. We snuggle sometimes at home, but nothing sensual. And then we had to rub our sweaty bodies against each other like it was the most desirable thing in the world."

"Oof, yeah, awkward," I said.

"It was too awkward to do that face-to-face," he said. "So at first we just danced against each other, her in front of me, facing away. It became less uncomfortable after the first few minutes, and we were able to melt into each other a bit more. It was actually kind of nice, because I feel like she and I have only recently become friends on our own terms and being able to dance together felt like it really solidified that."

"Great," I said. I tried not to sound too sarcastic. It's great that my sister was bonding with her future brother-in-law, but obviously the circumstances were a bit suspect.

"Yeah, it was for a while," he said. "Then the inevitable happened." He cleared his throat, stuttered, then cleared it again. Clearly he was getting nervous. "I um, well, I couldn't help but...you see, her butt was rubbing against my crotch and she's got a really, uh, sexy, I mean shapely, uh, rear. And I couldn't help but, y'know, get an erection."

"Uh huh," I said. I could hear him gulp. I wasn't too upset. I know he gets boners easily and I figured he would have given the situation. But I was still gonna let him twist in the wind on this one.

"She didn't notice at first," he went on, speaking quickly because of his nerves. "And then she did and gave me this look and I tried to explain, but the music was so loud, but I think she got it. Anyway, then she turned around so we were face-to-face. I mean, then my boner was just pressed against her tummy, but it was less intense than against her ass."

"Uh huh," I said, still making him continue.

"Also, guys kept staring at her cleavage, obviously," he continued. "I mean, I was too, because I was 'supposed to' after everything at dinner. But I was her date so I was allowed. Anyway, this let her mash her boobs into my chest to protect against all the gawkers." I didn't let him respond and let him sit in the silence. "Are you mad at me?" he asked.

"No," I said with a sigh. "I'm not like, excited about all this but I guess that's what I agreed to when I said she could take you as her date."

"I forgot how horny teens are," he said.

"I guess it's been a few years for us," I said.

"Yeah, so, I actually have a question about that," he said. "Her friends are all making out with their boyfriends and dates. Annie and I haven't yet, but it's gotten kind of awkward. They kept chanting for us to kiss on the dancefloor. We said we weren't comfortable with PDA, but they kept pushing it. Then, when I was leaving to come out here and call you, Victoria cornered me and demanded to know why I wouldn't kiss her."

"Ugh," I groaned.

"I tried to play it off," he went on. "But she lectured me about how her ex was so unloving and if I couldn't kiss her in public that meant I was also an asshole or something. It was really, uh, a lot."

"Yeah, Victoria can be like that," I said. She was always bossing their group around.

"Well, um, I kinda uh...promised her that I'd kiss Annie when I got back to the dance," he said.

"What?!" I said. Dancing was one thing, but I really didn't want my fiance kissing my sister.

"I didn't want to," he said. "But she wouldn't let it go. She was starting to get suspicious about why I had to come outside anyway. I wanted to call you ASAP, so I didn't know what else to do."

I sighed heavily. "What does Annie think?" I asked.

"I don't know, I haven't had a chance to talk to her," he said.

"Fine," I said. "If she wants you to, I guess you have my permission to kiss her. Just don't do anything more than what you have to to blend in."

"Of course," he said. "This has all only been about giving Annie the best prom experience."

I agreed and we said our goodbyes. I settled into bed and tried to fall asleep, but my mind couldn't leave the topic.

I'm no idiot, I know how hot my little sister has gotten. Any guy would love to make out with her, gawk at her boobs, grind on her, whatever else they've been doing. I tried to be less cynical about it, but it was tough. I just wished David was a little less naive. Victoria and everyone else weren't concerned with Annie's honor, or whatever. They just didn't want to feel ashamed being horny bimbos with their dates when David and Annie were right there behaving themselves. Annie's too young to tell the difference, and these sorts of emotional layers are the type that go completely over David's head. I suppose it's nice he tries to see the best in people, but I'm always worried about him getting taken advantage of.

I told myself over and over again that there wasn't much to worry about. My sister and fiance wouldn't betray me after all. Sure, she has a big crush on him and his obliviousness knew no end, but they were at a supervised school dance. They're going to kiss and touch a little, but nothing serious could really happen. After the dance ended, they were going to crash at Julia's parents' house, then drive to their lake house in the morning, where I'd be to keep an eye on them. It'll be weird walking down the aisle, knowing that my maid-of-honor had made out with my groom and even felt him grind his hard cock against her ass, but I guess that's what being a good sister means.

*****

CHAPTER 2

I was able to fall asleep eventually. I was pretty annoyed when I woke up to see zero updates from either of them about the rest of the night. I asked David how it went, but got no immediate response, which wasn't a surprise. I was all over the place trying to leave on time and I'm sure they were too. The lakehouse is on an island out in the lake and a ferry only makes the trip between it and the mainland a few times during the day. If we missed the first ferry, it'd be a few hours before it made another trip. It was an hour drive from our town to the ferry, and I didn't get a response from David saying they were on the road until it was 45 minutes before the ferry left.

The van carrying the high schoolers didn't arrive until they were about to pull the ferry ramp up. They just barely made it on, but they did. After exchanging pleasantries with the tired teenagers, I was able to pull David away from them to talk.

"How'd last night go?" I asked.

"Things got kinda wild. I tried to stick to what you said, but..." he said, trailing off.

Not the response I wanted. I don't know why I keep having faith David can navigate weird circumstances when he keeps getting talked into doing this, that and the other.

"What happened?" I asked.

"Nothing super crazy or anything. Just trying to figure out how to say it."

"Why don't you just start at the beginning."

He grunted, then sighed. Ugh, another long story, I thought. I reminded myself that everything was supervised and nothing could really happen.

"After we talked last night, I went back into the dance and started dancing with Annie again," he said. "She was acting really weird, just looking at me and blushing. I figured Victoria must have told her that I'd promised to kiss her, which she later confirmed was right. I thought she was feeling awkward about it, but I guess she was just nervous, because after a few moments, she just grabbed my face and kissed ME."

"Woah."

"Yeah," he went on. "She probably just wanted to get it over with after she knew it was going to happen. Anyway, after we kissed, all her friends cheered and made us kiss again. I thought that was going to be it, but then she opened her mouth and started french kissing me. I thought a closed-mouth kiss would be enough, but I didn't want to embarrass her in front of everyone, so I just went along with it."