Cherry Popping Stories
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Cherry Popping Stories
Cherry-pop Confessions
Cherry-pop confession stories and sins
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Hi, this is about what happened to me and my friend this summer. Both our families are nudists and we go to the same nudist resort a few times a year, usually during the summer the two families go together. I and my friend are both 15 and we are girls. Neither of us is particularly beautiful, I am probably termed ugly and my friend would be plain at best. She has a great body though, she is 5ft. 5in. tall, thin, small B cup tits, but she has a skin condition so that her skin on her body has many different colored patches on it. I am short and fat, I weigh 175lbs on a good day, and am 5ft. 3in tall. I have full C cup boobs, but honestly they'd probably be A cups if I wasn't so fat. My boobs are spread out across my fat chest and the nipples are turned in, almost like they are facing each other, they aren't straight forward. My mom won't allow me to shave my pubes so my friend doesn't shave hers either. In short . . . my friend Kara and I stick together like glue when we are at the resorts.
This year a boy who was 18 started talking to us and paying attention to us. We thought it was nice, and he was incredible looking with a great body, and from what all we'd seen at the resort and other nudist retreats over the years, he had a pretty big cock. After the first few days with over a week and a half to go on holiday, the talk gradually turned to sex. We told him that we'd never had sex and I admitted that I was too fat and ugly, and Kara said she wasn't great looking and when told she had a perfect body, she went on about her skin condition. That didn't seem to matter to Ronnie at all, nor did my being fat. On a hike that morning, we were discussing the same thing and he stopped, and kissed me full on the lips, then kissed Kara. He was very charming, and had convinced us that he really wanted to do it because of who we were. The next day we retreated to his bungalow, his parents got him a separate one from them, as they (like Kara and I suspected of our parents) liked to swing with other couples when they were at these resorts. In the privacy of his bungalow he was kissing us and then reached down and started massaging me between the legs. It felt heavenly and I never thought a boy would do that to me. He kissed and sucked on my boobs, then I watched as he did the same to Kara, also reaching around to feel her butt too.
He asked which of us wanted to be first as we stared at his huge, hard cock. Kara got on her knees and started sucking him, then he told me to get down too and I did it. I guess we both knew we were going to have sex for the first time. She was first, he stuck it in her and she gasped, he stroked in her for a few minutes, then I could see the blood as he pulled out. Wiping himself off, he moved to me on the bed next to a still lying down Kara, and got between my legs. Just as with her, he licked me down there first and I enjoyed it, then he pushed into me and I was no longer a virgin. He went back and forth, then picked me to receive his sperm. The next time he came inside Kara. After that we were both getting fucked several times by Ronnie. I think our parents knew we weren't virgins anymore. We both sucked him and once when we were both on the bed and he was on top of me he told me to roll over and he used some of Karas pussy juice and put it on my butthole and then had buttsex with me. It hurt but I wanted to please him so I put up with it. Later than night when the two were alone, Kara told me that he also did it to her. She wasn't going to let him do that anymore though.
I did let him have buttsex with me many times and got used to it. One day Kara wasn't around and I was at Ronnies and was letting him have regular sex with me when a friend of his came over. Ronnie wouldn't let me move, the friend came in and Ronnie got back on top of me. I was incredibly embarrassed, but the friend kept talking about how hot I looked like that. After Ronnie was done, he told his friend to take a turn and whispered to me how sexy it would be for me to "outdo" Kara. While that friend was on top of me 2 more guys came in, soon there were 5 more and they all stayed around taking turns. In the meantime Ronnie was telling me how sexy it was, so I did it. Once in the middle of it Ronnie had me roll over and let everyone watch him doing it in my butt. The next guy rolled me back over and did it regular. Ronnie left and soon came back with Kara. I heard him whisper "She's turned into a total slut now, I need a real woman, not a slut" and she stood there watching guy after guy have sex in me, with all their sperm leaking out of me as I laid there. I couldn't look at her, because I was actually enjoying the attention, having so many guys want to have sex with me. For the first time I didn't feel ugly and fat, I felt like a super sexy woman. The look in Karas eyes were daggers, and Ronnie took her to his bedroom and I could hear them fucking. She came out with her satisfied pussy as the last of the guys was finishing, the rest had all left. All she said was "Fucking slut".
I haven't had sex with anyone since, and Kara who was my best friend won't talk to me, and told other girls at school about my having a gangbang, and now it's up to 20 guys and there were only 8 including Ronnie. He took both our virginities in our mouths, butts, vaginas, and he won't give Kara the time of day. In fact the number he gave her wasn't the right number, he just wanted some kinky virgin-popping of two girls and didn't care how ugly or fat we were, he wanted to see how far we would let it go. I guess I went all the way, but she doesn't see how she isn't any better off than me.
Sad but you will just need to build your confidence. Beauty comes from the inside and confidence. Their are many who would still enjoy being your friend and will even like to treat you well. If you enjoyed it do not worry sex is beautiful and you should feel free to enjoy yourself.
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How much does losing your virginity actually hurt?
Losing your virginity can be awesome but it can also just suck. Sex scenes in movies and TV shows create unrealistic expectations for your first time, so please don't do something because your favorite character did it on Season 2, Episode 12 or whatever.
And just because the average age teens are losing their v-cards is about 17 doesn't mean YOU have to lose your virginity at that age. Lose it when you feel totally ready . Case closed. But always — a-l-w-a-y-s — use protection . Also, if you're concerned about your hymen "breaking," you should know that hymens actually just stretch. The phrase " popping your cherry " is misleading.
Here are several people's first time stories from both Seventeen readers and Reddit users that, uh, didn't go according to plan.
1. "I was 16. My boyfriend at the time and I had been together for about eight months and things were getting serious, so we decided to do it. I was expecting it to be so nice and amazing, but instead it was so painful. It only lasted a couple of seconds. " — Katelyn via Seventeen
2. "It hurt and I was not impressed with the guy and his 'skills.' I was in a foreign country partying it up in a hostel. I think he worked there and we made out on the dance floor before he took me a random room to have sex. There was no foreplay. I definitely bled and felt bad for whoever had that bed because the sheets were white so it was very noticeable , but I was beyond checked out and just wanted to leave so I booked it back to my room and never saw him again." — chocochump via Reddit
3. "It was just a whole bunch of awkward. I had no clue what I was doing. The guy claimed to know what he was doing but I'm not sure if I agree with that. My legs weren't long enough to straddle him. At one point he fell off the bed. He realized he was about to orgasm but wanted to last longer so he ran into the bathroom?? It was laughably bad." — Gogogadgetskates via Reddit
4. "I lost it when I was 14 on my boyfriend's brother's futon and I bled all over the pristine white comforter . If it had been with anyone other than my boyfriend it would have been sooo embarrassing." — Kelsey, via Seventeen
5. "My first time sucked. It was during my freshman year of college with an upperclassman frat bro. We'd been talking for months and I was convinced he liked me, though looking back on it now, his texts of 'What are you doing tonight?' weren't so much him liking me as they were him just wanting to get into my pants. Although he was relatively sweet to me during it, it still hurt like a b*tch and I got nothing out of it. At all. What stung the most was what happened after. He didn't text me at all and when I saw him at a party the next weekend he completely avoided me. If I walked into a room and we made eye contact he would immediately turn and walk out. It felt like a huge slap in the face. I liked him, but he had finally gotten what he wanted and that was it . He was over me. I wanted nothing more than to go up to him and yell and ask him why he was being so mean to me when I had done nothing wrong, but every weekend he would completely avoid me or be talking with another girl when I walked by. I have to admit that I'm still not 100% over it or him." — Cassidy via Seventeen
6. "Painful and awkward. In car somewhat drunk but also the lack of skill on both our parts to get going properly or communicate. And the blood. Everywhere. Got home and my mom knew since I bled on my jeans." — quickpeek81 via Reddit
7. "We were underneath her parents' bed while her parents (who came home from the movies early because they were all horned-up; hence, the situation) were on top of the bed, also having sex. We did not get caught. " — the_ouskull via Reddit
8. "Terrible, honestly. I was dating him, and he wasn't my first boyfriend, but we hadn't been together long and it was our first time seeing each other in awhile (different colleges). We were both pretty serious people, and we didn't know each other well enough to laugh at the situation. So when he kept coming out while thrusting, or when it hurt at first, we super weren't able to laugh it off, it was just humiliating and painful . Which is weird, because I am the least susceptible person to awkward silences ever. It was so bad." — babelincoln27 via Reddit
9. "I was 18 and in my first semester of college. The girl I lost my virginity with was a good friend of mine. One night, we were both coming back from a party. In the Uber home, we started flirting and making out. When we got back to her dorm, we went at it. Five minutes in, we heard a voice say, 'What are you guys doing?!' It was her roommate — sitting upright, staring at us from her bed. We were so busy hooking up that we forgot to check if she was asleep." — Jake via Seventeen
10. "I was dating this girl for a few months when I was 13. She was great — funny but shy, cool but aloof, and she liked all the same music I did. One night, when it was pouring rain, she came over. She couldn't get a ride, so she walked three miles. That made me think maybe she wanted to have sex, which was absolutely terrifying. We had never done that before. We're both shaking — her from the freezing New England rain, me from pure fear. I'm pretty sure I used some stupid line, like, 'We should get you out of those wet clothes' or 'Let's warm you up, babe.' She handed me a condom, and neither of us could figure out how to put it on, so I called my more experienced friend and had him talk me through it. Eventually, I got it on. I came immediately. It was so brief, I honestly still felt like a virgin. A few weeks later, we had sex again for a more respectable amount of time. I remember she said, 'OK, now I feel like I've had sex.'" — Ari via Seventeen
11. "[This was] my 'first time' with my GF at the time who had experience. I say 'first time' because we got the clothes off, started playing with her boobs, and then we change positions. I lay back and she moves to straddle me, when she moves and knees me right in the testicles ... It was over right then and there. I felt it for three days after. She was embarrassed for a while." — chigerfinger via Reddit
12. "We were having a tough time breaking my hymen. Neither of us had heard of lube so we used Aveeno lotion. I got a UTI. " — morelissapower via Reddit
13. "I had met a girl online and hung out with her once before we decided to have sex. I was so excited to finally lose my virginity. I was 18 at the time. I put on a condom and tried to stick it in, but a few seconds later, she was in pain. I pulled out, got dressed, and hurried out. I felt so embarrassed on the way home. I traveled three hours round-trip, was there for 15 minutes, and we didn't even fully do it. To this day, I still greatly regret losing it in that way. I haven't talked to her since." — Reid via Seventeen
Editor's note: Entries have been edited for clarity.
Stacey Grant is a senior editor at Seventeen who runs the brand's Snapchat Discover channel. She also covers entertainment topics specializing in nostalgia, such as classic '90s and '00s Disney Channel and Nickelodeon content.
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You thought your first time having sex was bad.
Apr 1, 2019, 05:45 AM EDT | Updated Jun 11, 2019
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Your first time having sex is almost always going to be a letdown: You’ll fumble with the condom or underestimate the need for lube. Or maybe your partner will starfish their way through the whole thing ― all 10 seconds of it.
You’re a clean slate, sexually speaking ― anything and everything can go wrong. Below, comedians, entertainers and other funny people on the web share the funniest things that happened during their first time.
“I was 16 years old, had zero knowledge of porn, zero knowledge of sex. I was in my boyfriend’s mom’s basement and we used his mom’s strawberry scented body butter as lube (please for your genital health, do not try this at home). The radio was playing Adam Sandler’s ‘Lunch Lady Land.’ Have you ever tried to have your first non-solo orgasm while listening to the lyrics ‘Sloppy Joe. Slop-Sloppy Joe’? Not good” ― Kyra Kane , the host of the Sex Work BB podcast
“I was in college and determined to lose my virginity so I just grabbed a guy at a party and started making out with him. We went to his dorm, I got my cherry popped, it was fine, mission accomplished. Leaving his dorm the next morning I realized I had no idea what his name was and had to try to find it using the campus directory for that building. He had a roommate so I guessed at which one it was.
I ended up telling my friends I’d banged the wrong guy. I was eventually corrected when I was confronted by the guy’s roommate’s girlfriend who’d heard through the small-liberal-arts-college grapevine that I had sex with her boyfriend. I explained and she and I laughed about it and are still Facebook acquaintances to this day.” ― Allison Mick , a comedian in Oakland, California
“There are classes in school that give straight people a decent idea of how it’s supposed to go but there are some key things that differ from straight sex versus gay sex, especially when preparing yourself for what’s to come. Being the brilliant person that I am, I just chose to eat one light meal at breakfast because I definitely, totally planned to have sex that night.
When we were getting down to it, I was so frustrated because it wasn’t working (mostly due to the lack of lube which NO ONE WARNS YOU ABOUT). Once again, being the brilliant person I am and a former Boy Scout, I knew to think on my feet so spit became the next best option. Despite the hiccups along the way, it was a successful but challenging experience and it has taught me that I can conquer any feat put in front of me.” ― Miss Toto , a drag queen in Miami, Florida
“My older cousin let me use his place and left a pair of Ray-Bans on the coffee table with a note that read ‘take them if you do it, leave them if you don’t.’ Being young and stupid I thought he wanted me to wear them while having sex. I wish I could remember more about that night but I couldn’t see much.” ― Daniel Tirado , a comedian in New York City
“I thought my first time would be romantic. That’s the image I had fantasied over since I found out what a ‘first time’ was. For the most part, it was fun: the basic cute kissing, gentle fingering, PG foreplay. But the grand finale really wasn’t all that grand: After several attempts trying to get it in, his elbow slipped, launching him all the way in and that’s when I heard it ‘pop’. I froze and screamed, ‘DID YOU HEAR THAT, YOU
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