One of the most fun – and awkward – experiences of my life [MFF].

I told this story in a PM, and since I went through all the trouble of writing it once, thought y’all might like to hear it too:

When I was in college I was dating a girl who happened to live in the next town over from me. In her case, the sister was a couple years younger. Both girls had been homeschooled and were pretty sheltered. My girlfriend was still a virgin, and wanted to wait for marriage, but was VERY enthusiastic about fooling around. I was her first for many experiences.

She and her sister were pretty close, but also had a bit of a competitive streak. My girlfriend was older, smarter, and more popular, but was jealous of her little sister bc the little sister was slightly more petite and got more attention from random guys (but didn’t have a lot of luck keeping their interest when they found out how conservative she was – or at least appeared to be.)

Fast forward to summer break, and I was invited to go to my girlfriend’s grandmother beach house. Me, my girlfriend, and her sister went down around mid week, and her parents were coming along that weekend, so we had the house to ourselves for 2 or 3 nights. The first night was pretty uneventful, with each of the girls in their own room and me on the pull out in the living room. Hower, after I thought little sister was asleep, I crept into my girlfriend’s room and we fooled around a good bit like we had done back at college (she was a big fan of oral, but had a rule that only one of us could be naked at a time).

The next day, little sister told us that she had overheard us fooling around that night, and threatened to rat us out if we didn’t tell her exactly what was going on (I think she thought we were having sex and desperately wanted to feel morally superior). My girlfriend told her what we had done, and that it was something we had done many times before. Thought the day, little sister continued to bring it up, and her judgement began turning into curiosity, which turned into my girlfriend teasing her about it. My girlfriend began bragging about how good I was, and telling her she couldn’t handle it because she’d never even been fingered by a guy. I tried to stay out of it, but my girlfriend’s teasing intensified and I sort of kept getting brought into it. That night, after a few beers that I had bought for them (I had just turned 21 maybe a month prior) we were all hanging out in the living room watching a movie when my girlfriend started getting a little handsy with me. I was embarrassed at first, afraid that her sister would see what she was doing under the blanket that was draped on my lap, until I realized that my girlfriend was watching her sister the whole time, waiting for her to notice. I remember trying to subtly get her attention to tell her to chill out, but she was purposely ignoring me. By the time her sister looked over to see what was going on, my girlfriend’s hand was up the leg of my shorts and boxers, stocking my already hard cock. When her sister finally saw what was going on, she shrieked in feign shock and said, “what the hell are you doing? I’m right here!” My girlfriend just said, “You want to watch?” I remember her sister calling her a slut, and my girlfriend calling her jealous.

With that, she pulled the blanket off my lap and my shorts and boxers to my knees in one, quick movement. I was a little more experienced than my girlfriend, and had never really thought much about being nude in a group of people – even in sexual situations – but I was a little shocked by this. Before I could really react though, my girlfriends lips were locked around my cock, and her sister’s eyes were locked on her. I tried to avoid eye contact with her sister as my girlfriend continued to suck my dick. She was never terribly skilled at it, but always enthusiastic. Eventually she moved to the floor between my legs and I began to glance over to see her sister’s reaction. Her face was blank, but her eyes followed every second of what was going on between my legs. I’m virtually certain mine was the first cock she’d seen, at least in person. My girlfriend was enjoying putting on a show, and reenacted every porn blowjob cliche she could remember.

Before I could cum she stopped. I wasn’t disappointed, because this was her typical MO. She loved getting me worked up before it was my turn to pleasure her. I think she considered it some sort of control thing. I didn’t mind because it meant I could cum last. She pulled my cock out of her mouth, stroked it a few times while looking at her sister, then pulled my boxers and gym shorts back up. When she got up from her knees in front of me, I noticed she had already taken her shorts off. She walked over to the sectional beside her sister and sat down wearing just her t-shirt, bra and panties. She gave me the “now YOU do ME” look I had seen many times before, and I slid into the floor between her thighs.

As I slid her violet cotton panties down I looked up at my girlfriend, who was already absentmindedly playing with her nipples through her t-shirt, just like she did every time I went down on her. I loved making eye contact with her when I ate her out, but that night I just remember her watching her sister. I went to work as I usually did, Fist with long, broad licks, then progressing to faster, firmer pulses with my tongue against her clit. She pressed my head tight against her, making it occasionally difficult to catch my breath, only backing off as I moved my mouth away to slide a finger inside her and press a second against her puckering ass. When she came, it was loud. I’m not sure if it was entirely genuine, or if she was continuing to put on a show for her innocent sister. As she pushed me away from the sensitivity of her orgasm, I looked up at both of them. My girlfriend’s sister’s head was on on my girlfriend’s shoulder, and her hand was under her blanket. I could see it moving slowly and rhythmically under the cloth.

As my girlfriend recovered, I took off my shirt. I was hot and out of breath. My girlfriend left her panties on the floor, but pulled her shorts back on. My cock was throbbing and my balls aching for release, so I climbed back on the couch, hoping my girlfriend would take the hint and go back to work on me as was the usual habit. But that’s not what she had in mind.

We sat there in awkward silence for a while. The sisters somewhat snuggled together, me right beside them with my girlfriend’s leg draped over mine. My cock pitching a tent in my gym shorts. Within a minute or two I could tell the moment was passing, so I got up to go get another beer from the fridge. As soon as I turned walked out of the door I heard them giggling. When I walked back into the room with three fresh beers, the sister was blushing and my girlfriend had a devilish look in her eye I had seen a few times before. Is I handed them each a beer, I looked at my girlfriend skeptically and asked, “whaaaat is it?” My girlfriend’s smile widened as she looked up at me and said, “I want you to eat her too.”

I immediately called bullshit and glanced at her sister, who was refusing to make eye contact with me. She was more fair skinned than my girlfriend, and it seemed as if her whole body was blushing. I just knew this was a joke or at worst, a set-up. “No way in hell,” I said, and my girlfriend’s face changed. “I’m serious,” she said. “It doesn’t have to mean anything, and she knows that. Besides, she wants it too.” With that, she pulled the blanket off her sisters lap revealing her pajama pants were already off, leaving just a grey cotton pair of panties, which were already dark and soaked with moisture. Her sister recoiled slightly, but my girlfriend rested a hand on her thigh and she relaxed somewhat. It was then that she first looked up at me. I tuned back to my girlfriend and told her it was a bad idea. She told me that they’d already discussed the rules. We weren’t allowed to kiss, her sister wouldnt do anything to me, and I couldn’t put any fingers inside her. “just lick her,” she told me. She turned to her sister. “Right?” Her sister looked first at her then up to me. “Right. I want to know what it’s like.” I looked back at my girlfriend. Every fiber of me knew it was a bad idea. But every porn fantasy I’d ever had was rushing though my head. I looked at each of them. “You’re sure? Both of you?” Her sister took a breath and whispered “yes.” My girlfriend grabbed my cock through my gym shorts and promised to show her appreciation later.

I got down on my knees in front of the couch, and her sister shyly slid down in the seat presenting herself to me. My girlfriend watched intently. I vividly remember my girlfriend softly stroking her sister’s thigh and arm. Her thigh jumped when I kissed it, but she spread her legs welcomingly as I moved closer. I looked up at each of them regularly for a sign to stop. My girlfriend continued encouraging both of us, telling me it was ok, telling her to just relax and enjoy. I could feel the heat coming from between her legs as I leaned forward and kissed her flat tummy, and felt her jump sharply as I kissed further down, eventually reaching the waistband of her panties. I traced the hemline of them with a finger, and watched both of their faces as I gently kissed the warm, wet grey fabric. As I broadly licked her through the panties I felt her jump again, and in that moment, a wave a guilt washed over me. I raised up and sat back on the floor, and told them I just couldn’t do it. They both had nearly the same expressions on their faces… an odd mix of relief and disappointment. I felt guilty for wanting it, and guilty for not following through. For a couple minutes, the awkwardness was unbearable, but soon it passed. We drank more beer, finished the movie, and I ended up jacking off in the bathroom after each of the girls had gone to bed.

The next morning was awkward, but it got better soon. By the time the girls’ parents got to the beach, it was all but forgotten. My girlfriend and I dated for about a year, then off and on for another few months. I ended up being her first, and she told her sister about it the next morning. Her sister was very flirty with me after that. Even to the extent of reminding me on several occasions that she wished I had gone through with it and that “the offer still stood.” By the time her sister and I broke up, she was dating a local kid that didn’t have a lot going for him, and was afraid to make the first move. I heard she went a little wild when she went to college, and I’m sort of happy for her about that. But I still think back to that night at the beach, and what was certainly the biggest “what if” of my sexual past.

Source: reddit.com/r/gonewildstories/comments/gc1huy/one_of_the_most_fun_and_awkward_experiences_of_my