My Naive Fiancé Goes to Prom

"Of course," I said.

"I knew joining them in the water would be trouble," he said. "But next thing I knew, Rick and Tommy were naked and in the water. Annie would look bad if her boyfriend was the only one to refuse, so I figured I had no choice. So I got naked and ran in too. As soon as I did, Annie and Nina surrounded me and, uh, took hold."

"What do you mean?" I asked.

"I mean of like, my dick," he said, forcing a weak smile. "I figured they'd try something once I was in there, but not that both of them would immediately grab me. Though it was pretty funny to have them basically fight over it. The water was cold and I was nervous, so it was soft at first, but the feeling of their two naked bodies pressing into me soon won over. That was good because then it was big enough for both of them to have a hand on it at the same time."

"Uh huh," I said. The logistics of his dick length weren't really the important part of this story.

"Anyway, the other two coulples were making out, so we did too," he said. "I tried to switch back and forth between the two of them so neither felt left out. They did a good job busying themselves while the other was making out with me. Like, I'd be kissing Annie, and Nina would knock her hand off my dick and really go to town on it with both of hers. Then I'd be kissing Nina, and Annie would take my hands and make me play with her big, naked boobs."

"I can't believe Annie was cool with all this," I said. "She was so withdrawn and shy for so long, and now she's letting you make out with her friend right in front of her? It doesn't make sense."

"Yeah, I didn't get it either," he said. "Well, at that point at least. It made more sense later on."

"What do you mean?" I asked.

"I mean...well, it'll probably make more sense in context later," he said. "Anyway, after a while, the water was too cold for us to handle anymore, so we got out. I figured that'd be the end of our adventure with Nina, but then she jumped on my back and then followed us once we got inside. I thought that Annie's 'college bro boyfriend' would be psyched that her hot little friend wanted to keep hanging out naked with us, so I played along. We wanted to rinse off the lake water, but Victoria and Rick were already in the bathroom and Julia and Tommy were already waiting, so that's why we came into your room. I'm sorry, I know that must have been awkward for you."

"It was, but I get it," I said.

"Thanks, hun," he said. "It did put things in perspective for me, though. I'd spent so much time in the headspace of being Annie's boyfriend, it was a sudden jolt of a reminder that actually I'm engaged to you, so I reminded myself to keep things as tame as possible."

"I appreciate that," I said. That's why I loved him. He let girls talk his clothes off, but he always remembered who he was actually with.

"That was tough, though, since I was about to head into a shower with two very horny girls," he said. "The three of us barely fit in that shower stall together, so I didn't have a chance to not touch them. We were all kind of rubbing against each other constantly. We did really want to get the smelly lake water off us though, so we focused on getting clean. At least at first. Nina finished first and immediately went back to playing with my cock, which had stayed hard due to how much they kept rubbing their soft, wet, nude bodies against me. Annie and I finished and we were all tired of being smashed in that stall together, so we got out and dried off. Nina finished quickly again, then knelt down and dried my legs off. And then...well, ugh, this is kind of silly."

"What was?" I asked.

"Well, Nina was kneeling in front of me, drying my legs," he said. "And then naturally got to my package and dried that off, then dropped the towel and just kept playing with it. Annie told her that my dick was fully dry. But Nina was like, 'I keep finding wet spots,' and then licked the full length of my dick!"

I just shook my head.

"She dried off the spot she licked, then took the whole thing in her mouth before letting it pop out," he said. "I couldn't help but moan. I thought Annie would be pissed, but she just glared at Nina. So then Nina told her to come take a look, and Annie rolled her eyes and knelt next to her. The two of them were kneeling naked in front of me, faces right in front of my bobbing erection. Annie said she couldn't see any wetness except for Nina's spit, and Nina told her to look closer. She did and discovered precum leaking from the tip. Nina told her to deal with it. I thought she'd just dry it with the towel, but Annie leaned forward, opened her mouth, and took the entire head of my dick inside it!"

"Annie!" I protested.

"Yeah, I couldn't believe it," he said. "She wrapped her lips around the top of my shaft and sucked, bathing the whole head with her tongue at the same time. I gasped and my knees almost gave out on me. That's when she pulled off and they moved me to the edge of the tub. I sat down, kind of dazed, and they got on all fours and slowly licked up either side of my dick. I was seeing stars at that point, and started falling back. I tried to grab on, and that's when I knocked all the shampoos and stuff into the tub and shouted."

"And that's when I came in," I said. "I'm glad I interrupted that. Sounds like you guys were about to totally lose it."

"Yeah, same," he said. "You shook us out of our reverie. We finished drying off and headed back to our room. I thought we'd just go to bed then, but before I knew it, we were right back where we'd been. I was laying naked on the bed and the two of them were laying between my legs, mouths on my dick."

"Wait, what happened?" I asked.

"I don't know," he said. "I came into the room, they ripped off my towel and pushed me on the bed."

"No, I mean like...I still don't understand this," I said. "I thought Annie was shy and reserved and everything. I can't believe she'd actually be down to...well, it sounds like you almost had a threesome."

"Ah, yeah, I thought the same," he said. "Annie filled me in later. Remember after she and Jeremy broke up and she spent a lot of time hanging out with Nina and her boyfriend?"

I nodded.

"Apparently, they weren't just hanging out," he said.

"Oh my god," I said. "They were all having sex?!"

"Yeah," he said. "Well, kinda. They were hooking up at least. Annie was still a virgin, so Nina's ex didn't fuck her or anything. But I guess they all fooled around a lot."

"It makes more sense why Annie was willing to let Nina throw herself at you," I said.

"Yeah, exactly," he said. "Annie said that soon after we got to the dance, Nina pulled her aside and more or less demanded payback. She said that you were supposed to hookup at your prom, and since she was single, Annie had to share her boyfriend."

"Wow," I said, shaking my head. "Wait, hold on...you said Annie was a virgin? She and Jeremy never had sex?"

"I guess not," he said. "Anyway, they spent a long time blowing me. I thought I liked blowjobs before, but having two girls go to town on you at the same time was really next level. While one was sucking on the tip or licking the shaft, the other would be bathing my balls with her hot tongue. And sometimes they would team up, like each running their lips and tongues up and down either side of my shaft. At one point, they even each took one of my balls in their mouth and tongued it until I was writhing and begging for release."

"Uh huh," I said. I didn't need all this detail.

"I was really trying to cum, because I figured then this would all be over," he said. "But they pulled off me right before I could bust. Nina asked Annie if she could sit on it."

"Wait, Nina wanted to fuck you?" I asked. I guess I shouldn't be surprised.

"Yeah," he said. "But Annie just looked worried and upset and Nina remembered that she was a virgin, which meant that she and I had never had sex. So Nina apologized and said that Annie should have sex with me first. We were both unsure, but then Nina said that prom was the perfect time for us to lose our virginity to each other. She was right, but the bigger issue was that we weren't actually in a relationship. I was her sister's fiance, not her boyfriend. We'd been playing around all weekend, but that was just for show. Actually having sex was on a different level."

"Ugh, yeah," I said. "And you couldn't exactly tell her that. So how'd you get out of it?"

"Well, after Nina cajoled us some, Annie looked to me and was like, 'Maybe I could just put it in to try it?'" he said. "My first impression was that that'd be fine, but then I remembered that we were all naked and had been teasing each other most of the day, so that was probably clouding our judgement. Then I thought about how it would play out if I said no. Nina would be disappointed because that meant that her sexy times wouldn't happen. And Annie might have been crushed had I refused her after all that. And I can't bear to think of Annie being upset, so I thought that if she was fine losing her virginity to me, I wouldn't say no."

"Oh my god," I said, putting my head in my hands.

"Are you mad?" he said. "I was just trying to keep everyone happy."

"You stuck your dick in my sister," I said.

"I know, but it wasn't like 'real'," he said. "It was all pretend. And not to split hairs, but I didn't stick it in her, she climbed on top of me and stuck it in her herself."

"That doesn't make a difference," I said. "I don't know why you didn't just say you were saving yourself for marriage or something."

"I know," he said. "I was just worried that if I started trying to justify saying no, everything would spiral out of control and Nina would figure out that I wasn't actually Annie's boyfriend. And if her friends found out that her boyfriend wasn't real and she'd taken her sister's fiance to prom, she'd never hear the end of it! I knew you wouldn't like it, but family is really important to me, and she's about to become my sister too. I couldn't let her down."

"Just tell me what else happened," I sighed. I didn't agree, but I could see what he meant. I guess I should be glad he values family so highly.

"Ok, so, Annie climbed over me and positioned my dick at her hot, wet entrance," he said. "We made eye contact and she mouthed, 'I love you,' and slowly sank down on it. We both moaned as I entered her for the first time. She fit me like a glove. She was steadying herself with a hand on my chest as she did, but once she got my full dick inside her, she got overwhelmed and had to lay down on me, mashing her boobs between us. We laid still a moment. I was glad she'd jerked me off in the car that morning, otherwise I definitely would have painted her back walls as soon as I got in. She was so hot and wet and tight and they'd been teasing me for hours at that point."

"What was Nina doing?" I asked. I didn't need more descriptions of how my sister's vagina felt on my fiance's cock.

"Masturbating on the bed next to us," he said with a chortle. "She kept saying how fucking hot we were and how happy she was to get to see our first time. Soon, Annie started moving her hips around on top of me, so I started thrusting in and out of her slowly. She regained her composure and sat up, grinding on me. Nina said she couldn't wait any longer and shuffled over to her and they started making out. I think that's when Annie came for the first time."

"First time?" I asked, raising an eyebrow.

"Yeah, well, I don't really know. You'd have to ask her," he said. Fat chance of that happening. "I barely managed to keep it together while she moaned and her vagina spasmed around my dick. I figured that if we had to have sex to save face in front of Nina, I should at least avoid blowing my load inside her. Anyway, after Annie came I heard her and Nina whispering. Next thing I knew, Nina swung a leg over me and sat her vagina back onto my mouth."

"Oh my god," I said, covering my mouth. "What a nightmare."

"More of a surprise than anything," he said. "I don't mind a hot, young pussy in my face. Some warning would have just been nice. So then the two of them made out while Annie rode my dick and Nina rode my face. Looking back, I'm surprised I didn't cum, but I guess I was just too overwhelmed for my dick to know what to do. Sensory overload."

"That's good, I guess," I said. The silver lining on this "my sister and her friend double-teamed my fiance" cloud.

"Nina came soon thereafter," he said. "The poor thing had probably been horny for two days, so she came really hard. We were surprised she didn't wake up the whole house with her screaming. Once she came down, she got off me and stumbled over to the couch, flopping down naked on it. Annie kept riding me, but just a few minutes later, we heard Nina snoring."

"Oh my god," I said.

"Yeah, she straight passed out," he said, laughing. "Which meant that we didn't have to keep up appearances anymore, but we both felt so good that we couldn't pull out at first. We both started feeling pretty guilty, though, since our reason for fucking just fell asleep. Then Annie said that we should probably take care of Nina, and got off me. We found the spare blanket and threw it over her and got a pillow under her head. That left the two of us standing naked in the middle of the room, safe but unsatisfied."

*****

CHAPTER 5

"What happened then?" I asked. He thought for a moment.

"Well, it was weird," he said. "We'd spent all day, all weekend, putting up appearances. And we were finally basically alone for the first time and could relax. But we'd gotten so worked up over the afternoon and evening. Hell, we had just been having pretend sex and my cock was still rock hard and dripping with her juices. I knew I at least had to finish myself off, but without the need to prove to anyone else that we were actually in love, it felt wrong to ask her to help me."

"Yeah, that makes sense," I said. I obviously didn't love that he and my sister had spent the day canoodling, clothed and not, and had even basically had sex. But at least he realized that we still had limits.

"I told her I was going to finish myself off," he said. "I sat on the edge of the bed and grabbed my hard, wet dick and started jacking off. She sat next to me and started masturbating herself. But after a minute, I heard her sniff. I looked over to see big tears rolling down her face."

"Oh no," I said. They were finally in the clear and all the emotions must have come crashing down on her all at once.

"I asked her what was wrong and she played it off like it was nothing," he said. "That was obviously a lie because she kept crying. I took her in my arms and we laid down on the bed. I just held her and stroked her hair while she sobbed. After a couple minutes she finally regained her composure and could talk."

"What'd she say?" I asked.

"She started off saying she knew she was being silly," he said. "And then started talking about her relationship with Jeremy and how, even though she thought she was head-over-heels in love, the whole time she knew something wasn't right. He was an asshole and because of that, she never wanted to have actual sex with him. Once it finally ended, she was so glad that they'd never done it, so she could save her virginity for her perfect guy who deserved it. And now, even though we never finished, the first time she let a guy into her was with her sister's fiance and it was all pretend. And then she started crying again."

"Oh my goodness, no," I said. My heart sank. I'd spent all weekend feeling like some kind of martyr or saint for letting her pretend my fiance was her boyfriend. But now I wondered whether that had been a mistake from the beginning. "What'd you do?"

"I stroked her hair and told her that it didn't matter," he said. "Sex isn't a yes/no question, there's lots of shades of gray, virginity is a made-up thing that is much less important than society acts like it does. She said she knew all that, but it just hurt to know that this past weekend had been the most fun, romantic and sexy weekend of her life and it was hard to know it wasn't real. Her perfect boyfriend didn't exist, I was just putting on an act and she didn't deserve to be happy."

"Yikes," I said. I felt myself tearing up just thinking about my sister going to that dark place. She could be dumb and annoying sometimes, but I really did love her.

"I felt there was only one thing for me to do," he said. "Which was tell her that I think she's amazing, smart, funny, beautiful, kind and sexy and that any guy would be lucky to love her. She smiled and said she appreciated the effort, but said she knew that I was just saying that. That I had to say that because I was her future brother-in-law and that's what any brother is supposed to say. So then I said, 'Is any brother supposed to do this?' and I leaned in and kissed her.

"At first she didn't respond, just looked at me questioningly. Of course, we'd kissed plenty of times over the weekend, but always because we 'had to'. So I said, 'This isn't your pretend boyfriend David kissing you. This is your real Davey kissing you. This is how I really feel.' I kissed her again, this time with more passion, and she responded, kissing me back. She came alive and got really into it. It felt so good to finally be kissing her as myself, showing her how I really felt and not playing a role. I noticed she was still crying, and she said, 'Don't worry, these aren't sad tears. I'm so happy!'"

"Phew, that's good," I said. Too bad it required my fiance kissing her again, but I was glad he made my sister feel better.

"Yeah, I was so relieved," he said. "After sharing some chaste kisses, we started full-on making out. We were so happy to have shared this experience together, it was hard to stop. Plus, we were still fully naked, mashed up against each other and barely 15 minutes earlier, we'd been having sex in a threesome. I was fully erect again in no time, which she quickly noticed and she took me in her hand. Soon, our hands were all over each other as we rolled around on the bed making out. We'd touched, felt and seen each other a fair amount over the weekend, but this really felt like the first time again since we were finally doing it without pretense and with our true, unbridled feelings.

"Before I knew it, I was laying on top of her, her hand around my hard member and her legs wrapped around my waist. I leaned down to kiss and lick and suck her beautiful huge tits and our bodies shifted so that my dick was lined up with her vagina. I felt her rub the head of my dick up and down across her wet lips and back and forth against her clit. Then she lined me up with her hole and pushed me toward it with her legs.

"I stopped her right as the head of my dick parted her folds and asked if she was sure. She asked if I loved her and I said I did and she responded that then yes, she was sure. So then I plunged fully into her steamy wet depths."

"You fucked my sister?!" I asked. "I know you guys had messed around plenty, but that was all for a reason. This is just because you wanted to fuck."

"Yeah, but that was the whole point," he said. "I knew that I could have rolled off of her and said it was too far. But then we'd be back to square one. I had just been pretending to like her so she'd feel better about herself. I didn't actually like her. No guy did and she'd be alone forever."

"You know that's not true," I said. "She's barely 18, she'll find someone. She's barely started."

"I know that, but she didn't," he said. "I figured that since I'd already been inside her when we were playing pretend in front of Nina, it wouldn't be that different now that we were alone. It's easy to look back now and second guess, but it's impossibly hard to say no when your every hormone is screaming at you to just fuck this sex goddess that's begging you to. Especially if you know that if you stop, you'll once again have a crying teen girl on your hands."