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Rosie – 16 years old, junior in high school – 6'-2" tall, 138 pounds – member of school volleyball team.

Michael – 17 years old, senior in high school – 6'-2" tall, 185 pounds, football team captain and tight end.

Taylor – 15 years old, junior in high school – 5'-5", 130 pounds, avid Scout and camper. Has been going steady with Rosie for the past four months.

Skinny Rosie unexpectedly falls for hunky, football team captain, Michael. Things escalate. Will Rosie, who is going steady with Taylor, cheat with Michael and allow him to go all the way one weekend when the parents are away. How do they handle the inevitable trouble that results from this hook-up?

'How had this happened?' I wondered. Michael's heavy body pressed against mine as we Frenched. His tongue diddled against mine. Both us were topless. The wisps of hair on his chest tickled me as our bodies rubbed together. His body rubbed against my stiff nipples.

"You make me so fucking hot, Rosie," Michael gasped between kisses.

My parents were away for the weekend. I was alone in my room with the hottest guy in our high school. We had all afternoon alone, with no possibility of being disturbed. Could I go through with this? Could I go all the way with this ... this boy?

Michael and I continued making out. It felt ... amazing. I'm no stranger to first base – or second and beyond either. It was more intense than I'd ever experienced while dating others. The way his body rubbed against my chest and the things his tongue and lips were doing to me ... God, he made me so horny!

I knew I was having the same effect on Michael. His "package" was hard and pressing into my stomach. Would he want to go all the way with me, a tall, skinny volleyball player? He's a senior, a captain and a tight end on our football team. Me? I was, by everyone's agreement, a beanpole and a year behind him in school.

None of my insecurities affected Michael. He continued kissing and dueling his tongue with my tongue. I wrapped my arms around his muscular sides and back as we made out. Michael slipped a hand between our bodies, grasping my chest so my stiff nipple was under his thumb. He rubbed it. Oh ... My ... God!

I thrust my tongue into Michael's mouth. He sucked it in and twirled his tongue against mine. We continued, heedless of anything except lips on lips and tongue on tongue. We made out frantically for ... minutes? Who knows? Finally we had to break our lip-lock momentarily to breathe.

"God, Rosie," Michael gasped between pants. "Why'd we ever stop being friends?"

Michael and I had been had been playmates when we were small, before his family moved to another neighborhood.

"Different elementary schools?" I offered. "Different circles? I don't know."

Five years at different elementary schools had killed whatever connection we once had. By the time I was in the same middle school as Michael, I had my friends. He had his. Anyway, he was a grade ahead of me. We said, "Hi," when saw each other in the hallways. Nothing changed when we moved on to high school – until the school year started a month ago.

Michael and I were signed up for the same Photography class. By chance, our teacher assigned us to sit at the same table. The decade apart just seemed to slip away as we talked, laughed and worked together. Soon Michael was teasing me and calling me Rosie again, like he had years ago. I responded by calling him Mikey, but that didn't last. It didn't fit the football tight end image he cultivated. I settled on calling him Michael.

Our friendship rekindled and then burst into flame two weeks ago. I'm supposed to be in a steady relationship ... well ... I AM in a steady relationship right now. Things escalated beyond friendship two weeks ago when Taylor, my steady, had a Scout camping weekend. Recently broken up with his bitchy, high maintenance girlfriend, Brittany Miller, Michael and I decided to go to the movies on a Friday night – just as friends.

We saw one of Pixar's animated flicks. It was funny. We laughed and had a great time. Things developed further at the end of the movie when Michael drove me home. He pulled over and stopped a block from my house.

"This was a great night, Rosie," Michael. "You have no idea how much I enjoyed this."

"I had a great time too," I agreed.

"I need to admit something, Rosie," Michael said as he stared into my eyes. "You will keep a secret for me, won't you?" I nodded yes. "Maybe I should show you rather than tell you."

I was shocked when he put his hand around my neck and pulled my head closer to his. He leaned in and kissed me. On the lips! I was flustered and startled but my body responded when he slipped his tongue into my mouth. My eyes glazed over and I saw stars as this ... this boy kissed me like I'd never been kissed in my life.

We necked for probably five minutes. It was nothing like when I necked with Taylor. Taylor and I had gone much further sexually in the four months we'd gone steady but the feelings then were nothing like these now. I finally realized the time as Michael and I made out.

"I've got, like, three minutes to get home," I protested as I broke away from his kiss.

"Are you all right with this?" Michael asked. "I didn't freak you out with the kiss?"

"I don't know," I admitted. "I never expected ... I ... I'm just confused."

"This is our secret?" Michael asked.

"Yes, totally," I agreed. "How could I tell?"

"I want to be more than friends, Rosie," Michael responded. "Can you feel that way ... about me?"

"I don't know," I answered. "I just don't know. This is all so unexpected. I never suspected you ... I have Taylor."

"Do you love, Taylor?" Michael asked.

"Love?" I remarked. Taylor and I had fun together. We explored each other's bodies as we learned about what teenaged hormones could do. It was fun but ... was it love? "I'm confused. I need time."

"Fair enough," Michael said. He planted one more, less intense kiss on my lips. "Let's get you home before you turn into a pumpkin."

Michael and I surreptitiously hooked up half a dozen times after that movie. Mostly they were make-out sessions except for last Wednesday after school. Michael had given me an oral quickie. It blew my mind. Taylor had tried before, without nearly as much success. The feelings were so much more intense with Michael. Wednesday's quickie, and Taylor's announcement that the family was heading to the west end of the state this weekend to visit the grandparents, led directly to Michael being alone with me this afternoon in my bedroom. We would explore whether I was ready for a serious relationship with Michael.

"Rosie, I am falling in love with you," Michael declared, as he sprawled on top of me, chest to chest in my bed.

"Is that a good thing?" I responded. "What are people going to say?" Michael laughed.

"It's a black-white thing, isn't it?" he asked.

"No, it's not," I declared. Michael always joked about being a black man. I guess to some he would be considered black, no matter what he looked like. His dad is a red-haired Irishman with skin paler than mine. Granted, his mom is considered African-American, albeit, a very light skinned African-American. Michael had straight red hair that looked nothing like what you would expect for a black person. His skin color was slightly darker than my Caucasian skin, but only to a slight degree. He certainly wasn't black. Not even brown or beige. Michael's skin color could best be described as matching my coffee, on the few occasions I drank coffee – lots of milk and sugar with a touch of coffee for flavor.

"What then?" Michael asked rhetorically. "I don't give a rat's ass what people say. I am falling for you and I don't care who knows."

"It isn't that simple and you know it," I insisted. "People WILL talk."

"Fuck 'em!" Michael answered.

"That wasn't the idea for this afternoon," I said. "I wanted you to do that to me, not everyone else."

"Are you sure, Rosie?" Michael asked. His face went serious as he stared into my eyes. "We don't have to if you don't want to."

"I need ... no, we need to explore what this is between us," I responded. "I need you to take my cherry this afternoon. I need to understand this."

"It may hurt," Michael said. I could feel that big, steely bar in his pants, pressed into my abdomen. I knew he wasn't going to be small. This would be a hell of a first time for me.

"I'm sure," I answered, laughing and pointing to the bottle on my dresser. "I bought lots of lube. I hear that is important for the first time."

"Lube is always important," Michael agreed. "If it isn't sloppy it isn't good."

"Let's do this," I declared. "Kiss me again." We swapped tongues for a minute or two. Michael sat up, straddling my torso.

"We've got too many clothes on," Michael remarked. That was only partly true. Michael and I took full advantage of this late September, Indian summer weekend to dress in T-shirts and sport shorts today. This weather was simply not normal for late September in Connecticut. I pulled his shorts down to reveal a pair of gray Under Armour boxer-briefs. Michael hopped out of bed and shucked the shorts but kept the briefs on.

I eyed the bulge in Michael's briefs. I don't know if the stereotype of all black men having big cocks was true or not. I did know Michael was well endowed. I gulped as I thought about that big thing going inside my body. Would it fit?

Michael reached for the waist band of my shorts. I popped my hips up and let him lower the shorts. I don't know if he expected it or not, but my shorts were lined. I had nothing on beneath my shorts. I plopped my bare butt on the bed and lifted my feet up so Michael could remove the shorts. There I was in all my skinny, pale, white glory.

"Too skinny," I remarked as Michael stared at me. "I know. Everyone says it."

"You look hot," Michael answered. "I want to make love to you so much."

"That is what we are here for," I said. "If you still want me."

"I most definitely want you, Rosie," Michael declared as he clambered onto my body again. His hard, 185 pound body pressed against my body as we returned to kissing. He rubbed his hard, cloth encased package against my naked crotch as we continued making out. Hot? God, this boy was making me hot.

Michael switched to kissing my cheeks, nibbling on my ear lobes and then kissing down my neck. He continued down across my chest until he hit one of my sensitive spots, my hard nipples. Michael knew it. He lavished attention to kissing, suckling, nipping and biting my sensitive brown swirls of flesh.

This was mind blowing already. Taylor and I enjoyed our sexual exploration together but it had never, ever been this intense for me. Michael continued sawing his hard, cloth-covered erection against my naked groin. I was afraid I would come just from Michael's dry humping.

I managed to squeak out, "You still have clothes on," between moans as Michael blew my brain's circuitry. He stopped his assault on my nipples momentarily and hopped out of my bed. He smiled before slowly pulling his boxer-briefs down.

The sight confirmed all my hunches about Michael's endowment. This boy was big! I stared at his cock. It was a brown, quite a few shades darker than the rest of his body. It had a light band of skin just below the big, purplish-brown head. I shuddered as I stared at the mesmerizing organ. It had to be eight inches long and a couple inches across. That was going in my body!?!?

"Are you ready for this, Rosie?" Michael asked as he gestured towards his cock.

"Soon, but not yet," I answered. "Come up on the bed. You went down on me last Wednesday. I want to return the favor."

"You know you don't need to," Michael responded. "We can hump some more or get down to the main event – whichever you want."

I patted the bed. "You went down on me," I explained. "I want to return the favor."

"I won't turn down a blow job if one is offered," Michael answered. "Just remember, it isn't necessary, if it grosses you out or anything."

"I've never done it before, but I am willing to try."

Michael climbed into my bed and lay down beside me. I scooted around cross-ways on the bed and lowered my head towards Michael's groin. This cock was impossibly big.

I had no experience giving blow jobs but had read up on the techniques on-line since Wednesday. I knew I needed to share everything if I was to develop a relationship with Michael. If it turned out that I was willing to have a relationship with this boy.

I swallowed hard and engulfed his big cockhead with my mouth. "Teeth!" Michael hissed.

"Ssoorrwwy," I mumbled with a mouth full of cockhead. I tightened the seal with my lips and made sure my teeth didn't touch Michael's sensitive cockhead. I swirled my tongue around the big invader. I could hear Michael moan as I sucked him. I wrapped one hand around his cock shaft. Damn! This boy was big. My thumb and forefinger couldn't touch as I encircled the engorged phallus. I stroked the big boy as I suckled and teased the head.

I must have been doing OK. Michael was moaning and squirming as I blew him. I pulled off his engorged head. Michael moaned an "ahhhh..." I licked around his head for a moment and then licked down the big vein on the underside of his cock, until I reached his balls. I licked around his hair-covered balls. I tried to suck one of the balls into my mouth. It barely fit. Michael's balls were proportional to his big cock. I licked my way back up his cock again before engulfing his head with my mouth.

I sucked and stroked, stroked and sucked. It didn't take very many minutes before I noticed Michael tense up. I knew the meaning of this. I sucked extra hard and swirled my tongue around his cockhead while I stroked his shaft. Michael moaned and squirmed from my efforts. He tensed and growled, "Oooohhhh ... Shit! I'm ... gonna ... FUCKING ... come..."

I could feel his cockhead swell in preparation for firing. I was OK with giving head but I wasn't ready to swallow, at least not yet. I gave Michael one more suckle before pulling my mouth away. I felt his cock pulse as I pulled off. The first spurt of semen spurted against my cheek. I pulled further away. The rest splattered across his chest and stomach, pooling in his belly button.

Michael gasped and panted. I sat on my haunches and looked down at the boy. He just glowed from his orgasm.

"That was fucking awesome, Rosie," Michael finally panted, as he recovered his wits. I wallowed in the boy's praise as he recovered. I grabbed some tissues from my nightstand. I wiped the come off my cheek before cleaning up Michael's belly.

"You ready for the main event?" I asked. Michael was fisting his tumescent cock.

"I'm almost ready but you're not," Michael answered. He motioned for me to lay down on my bed again. "You need to try some fingers before you get this." He waved his rapidly hardening rod towards me. "This might be a bit much for the first thing in your hole."

"You know better than me," I admitted.

"Where's the lube?" Michael asked. I pointed towards my dresser. Michael hopped out of bed and retrieved the squeeze bottle. Michael pushed my legs apart and climbed into bed between them. He pushed them up so my knees were practically up to my shoulders. He squirted the cool lube onto his fingers and then probed down below for my hole. He let his thumb strum across the sensitive area above my opening.

I tensed as I felt his fingers spread the cool lubrication around my opening. I tensed when Michael tried to worm one finger into me. "Relax," my soon-to-be lover commanded. I tried my best. The finger slipped into me. I felt Michael probe my insides for a moment before withdrawing it. The finger returned again, pressing more easily into my hole this time, cool from the additional lube Michael had applied.

I wasn't sure if I would be able to stand something thrust inside my body. I found one finger felt OK. Actually, more than OK. I was getting into his finger fucking. Michael stopped for more lube two more times. I felt stretched a little each time he returned the finger to my insides.

"Does three fingers hurt?" Michael asked soothingly.

"Three?" I gasped. "That's three?"

"It is," Michael confirmed. "Three with lots of lube and plenty of preparation."

"Am I ready for the real thing?" I asked. The moment my cherry disappeared was rapidly approaching. That big, brown, monster was looking huge again. Could I do this?

"Let's try four fingers first," Michael suggested.

"You have the experience," I agreed. Michael pulled his fingers out again for more lube. I knew he had applied a lot. I could feel it running down my bottom and between my butt cheeks. There was a little pressure and a pinch as my soon-to-be lover forced four digits into my poor, stretched hole. Michael finger fucked me for a minute or so. I didn't feel any pain.

"I think you're ready," Michael announced. "Are you sure you want to go all the way, Rosie?"

"Absolutely," I confirmed. "Take my cherry."

"OK"

"You are going to use protection, right?" I asked.

"I'm not an idiot. It's 2014," Michael responded. "This never goes anywhere without being wrapped." I watched as Michael pulled a condom out of his pants pocket and tore the wrapper open. He carefully unrolled the sheath down over his huge cock. Michael spread lube over his humongous organ as I watched.

'Was I really ready for this?' I wondered. Michael's cock looked much too big to ever, EVER fit inside me. Michael clambered into bed again, between my legs. He pushed my legs back so my knees were pinned against my shoulders again, neatly exposing my hole for his use. Michael gave my hole one more shot of lube before scooting up against me. I stared down at that big, angry looking brown rod. Was I ready for this?

Michael nestled the head again my hole. I involuntarily clenched my muscles. "Don't tense. This will hurt if you do." I willed myself to relax as he stared down at me. I could see the love and concern in his eyes as he prepared to deflower me.

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DISCLAIMER: All individuals in this story are adults. If you are not an adult, you should go play with Legos or something until you can read stories like this. --"Pop My Cherry"--- by alphaspiritNY "I want you to pop my cherry!" It's loud in the club, and the girl has to shout in your face. Her speech is slurred, her thin, white shirt drenched with sweat and alcohol. She's got glitter and face paint all over her, tie-dyed bangles and bracelets jangling silently in the raucous cacophony. "What?"...

1 year ago
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Giving up my anal cherry

Before meeting my husband Victor, I lived during some months with another guy, Daniel; with whom I shared a flat in Buenos Aires.Daniel and I had very good sex; we fucked every night with a mix of love, passion, lust, anger and v******e.The only matter for me, was that Daniel did not dare to fuck me in the ass. He said I could be hurt by his dick; so he did not want to sodomize me at all.I begged him and insisted, because I was curious…One evening, we invited Daniel’s sister, Julia and her...

4 years ago
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Popping Stephanies Cherry

Popping Stephanie's Cherry It happened when I got a text from Stephanie that Vanessa her mom my ex girlfriend had to go pick up her brother as he got in trouble in school and she was running late. I replied "to late I am almost at their house". "She is going to be there awhile it will be just you and me then" Stephanie replies. "Okay I don't mind waiting plus we have never talked before it would be fun to get to know you since your mom and I are bf and gf "I replied. "Yeah I guess it would be...

1 year ago
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My Oral Cherry

It early Saturday afternoon and I was going to the school pool for a training session with the school swim team. We were in training for a competition against another school from another city. We had never beaten them before and were really trying hard this time.I got there early as I wanted to laze around in the pool before we got in to it.When I got there the door was open but nobody seemed to be around. I got changed and lay in the sun.I had been there for maybe 10 minutes when the swimming...

3 years ago
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Her new toy takes my anal cherry

Ready for some more wild shit? Hey guys, I'm sure you have seen those make your own dildo kits. You know the kind, where you make a mold of your own dick, and use it to make a vibrator so your significant other can fuck themselves with it when you're not around. Well, I'm here to tell you be careful, if you get one of those, the decision might come back to bite you in the ass. Or worse. Here is my second chapter…As we get out of the shower she guides me on the edge of the bed and has me sit...

3 years ago
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Nancy awards her cherry

Hello all ISS readers! I am back again with a hot sizzling story. As you knows me I’m Abhishek Singh 18 male living in Delhi near mother dairy of Pandav Nagar. I will hope that u will enjoy the story. Mail me any comments, queries or anything on or She never understood herself in that regard. She knew she would eventually loose her virginity and twice she thought she had found the right guy to do it. Each time Nancy backed out realizing at the last minute that it was the wrong guy. Both times...

Lesbian
2 years ago
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Dads MindControlled Daughters Chapter 3 Popping the Daughters Cherry

Chapter Three: Popping the Daughter's Cherry A Belt Buckle Mind-Control Story By mypenname3000 Copyright 2021 Notes: Thanks to WRC264 for beta reading this! After an hour of searching the internet, I could not find any match on the belt buckle my daughters had bought me. There were plenty that said “Best Dad,” but none were in quite the same style. Had quite the same shape to the panel. “We bought it at Target, Daddy,” Janelle had texted me along with a picture of her breasts in the...

2 years ago
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Kaylies Lost InnocenceChapter 2 Losing Her Cherry

Now that she was a legal 18 year old and had managed to suck her brother's friend Alex's cock several times, Kaylie felt she was starting to move into a more mature outlook on life and was no longer clueless. The only thing that really continued to bother her was the technical aspect of still being a "cherry" girl with her hymen intact. She talked to her girlfriend Angie about using her mouth on Alex and the fact that she found out that she actually liked it. Angie was shocked because...

3 years ago
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Shaynas LifeChapter 6 I Finally Lose My Cherry

My intention in writing this tale is not to detail every sexual experience I have had, but to concentrate on those events that were either first-times for me or significant in forming who I am today. So in that light, I will just summarize my last two years of high school: Junior year - boys dated - 3 serious relationships - 0 hand jobs given - approximately 10-12 blow jobs given - 5 (some of the hand jobs ended up as bj.s, so there is some overlap. I wasn't as much of a slut as it seems....

4 years ago
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Lesbian Mind Control IncestChapter 2 Nubile Daughterrsquos Cherry

Note: Thanks to Ron for beta reading this! My youngest daughter, only fourteen, stared at me, her drunk thoughts struggling to comprehend what I had just told her as I sat naked on the couch in our living room. My eldest daughter, seventeen, hid her head in shame between my thighs. Her face was covered in my pussy juices while her best friend, Lily, still licked at her cunt. Janet, my youngest, blinked her brown eyes, adjusting her glasses on her cute nose. “What?” she blinked. “Take...

3 years ago
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Lisa Missed The Bus and Her Cherry

Kenneth Wagner was flabbergasted!He couldn't decide if he was insane or not. An hour ago, he was a king. Now, he'd been reduced to shit! At the age of 43, an executive for a multinational group of companies, he had always maintained his status, in and out of the office, among his community and his near and dear ones.But what happened a bit ago changed all that!Visuals of the last hour unfolded in his mind. He could not erase the images from his memory, nor reverse the activities that took...

3 years ago
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GIVING HIM MY HOTWIFE CHERRY

So this is a bit of sexy fiction where in I wrote a fictional story of fucking one of my fans here on the site. Hope you guys like it. I'm looking for inspiration to write about a girl-girl thing too so DM me. THE AIRPORTFive hours on a flight to find out they canceled the conference at the last moment because the state shut down, again, due to the pandemic. Fuck. I could have saved myself the trip. The airport I was at would normally be full of throngs of people. Guy people I could flirt with....

3 years ago
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Watching sweet Lena giving up her anal cherry

I used to cross Lena’s path during the morning, since she was a dog walker for an elderly couple down our street. She was a beauty Croatian young babe in her early twenties, with a nice slender body and swaying hips that were quite a hit amongst many guys in the neighborhood.I loved specially her broken accent and the soft tone of her sexy voice. I had ever fantasized several times with having this nice babe in my bed; but every time we crossed our paths on the street while she was walking the...

3 years ago
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The Skate ParkBustin Bros Cherry

The Skate Park Bustin B R O S CherryI woke up after a couple hours nap. Still kinda groggy—it was just a lazy fuckin day. Went up to the kitchen to start the chile I promised my lil b r o. All my homies loved my chile, but I didn't call anyone tonight. Decided to keep it quite, just me and b r o.We woofed down the chile and dogs like we hadn't eaten in a week. Headed back down to the basement to find a movie, and just chill. I paused at the bottom stair, and waited. Finally lil b r o got...

1 year ago
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Restaurant Cherry

It started out as just another day in the week. Get up, catch the train in to town, go to work for 8 hours then catch the train home. I work in a bank and have been in this branch for 8 years. I had started out as a teller and progressed through to the lending department.There are a lot of really nice looking girls working there and some really good looking female customers as well. I’ve had a couple of girlfriends, but can take or leave them.Ever since I was 17 I’ve wondered what it would be...

3 years ago
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POP GOES THE CHERRY

POP GOES THE CHERRY I recently read a delightful account of a young gurl loosing her virginity to a family friend. Got me thinking about loosing my own virginity.First, you should know, my mother made me a sissy. She took great delight in dressing me as a little girl, thinking back I can not remember when she did not. We lived in the country and most of the time growing up I played outside with my dolls in dresses. The only time I wore little boy’s clothing was when family visited or I...

3 years ago
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Popping my cherry

I like my aunt Sarita and cousin Rahul. She lost her hubby after Rahul was born. She was rich and both had a luxurious life. I used to visit them since c***dhood and spend my vacation with them. Rahul was a college student and I had finished my school and awaiting results. My Aunt looked very beautiful and I could imagine during her younger days, she must have attracted so many youngsters around her. Rahul too was well built and they were all open and free and fun loving. I was having very good...

3 years ago
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Banging My Best Friend 8211 Popping Her Cherry

Hi I’m Raj. I’m 21 years old. I’m 5’11. Well built with a 6” tool. I’m from Hyderabad. So any women & girls who would like to have secret fun or chat. Email me at I respect your feelings. Privacy will be maintained . Do drop your comments in email too. Names Changed. Best Friend I’m in final year of my graduation & this story happened in my third year. I have two best friends Shreya & Priya. They both are best friends indeed. So it all started with Shreya. She is slim and dusky color with a...

2 years ago
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Paula and Ian Cherry

Tina was abso-fuckin-lutely just chipper after her deflowering. Her and Mark were like sickening examples of love and joy. I had been moved to the side car of Tina’s life. It sucked.“Why so glum, chum?” Ian said coming up to my table.“You are such a fucking dork.” I said.“Dork? Man, you must be out of it if that’s the best come back you have.” Ian said. He sat down and slipped a CD across the table at me. “What’s this?” I asked.“It’s a CD full of old-school Goth music. Try it, you’ll like...

First Time
3 years ago
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Sandy loses her cherry

Larry and sandy wilson were relaxing in front of the television on this spring evening. Their three children were paying attention to the program that was airing; but larry and sandy were less engrossed. Sandy was paying more attention to the book that she was reading and larry was dozing off periodically. Larry began thinking about how they had gotten to this place in their lives since he met sandy while they were both in college in ohio. Larry had been in the first semester of his senior year...

4 years ago
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Dinner and a Cherry

The next day was like any other and on arriving home, Nancy met me at the door. I didn't tell her, but I was a little disappointed in not playing the what person game at the door of the garage, but she had her agenda and we had someplace to be. So into the house, down to the basement, a quick douche, and shower, then back up to our room to get dressed.“Harriet, you look very nice,” Nancy said as I stood before her.“Thank you,” I replied.“And just as important, you look very convincing,” she...

Crossdressing
3 years ago
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The Dead Frog and Sues Cherry

You are probably wondering what a dead frog has to do with Susan Bloomington losing her cherry at the ripe young age of 16. In all honesty, Sue never expected to lose her cherry so sudden like and she certainly never expected it to be with her step-brother Ryan to whom she had always carried a particular dislike because of his sarcastic mouth and slovenly ways. When they first learned about the family camping trip to Lake Tahoe, neither Sue nor Ryan really wanted to go but they soon discovered...

3 years ago
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The FavorChapter 8 The Second Cherry

I lay on the bed panting, Rachel lying draped across my side, and I was amazed. Life is full of the plans you make, and you plan for contingencies, but you know things won't always work out. Given the short amount of time that I had to plan for this particular event, probably one of the seminal events of Rachel's life, I was sure that I would screw it up. But I didn't. Oh, I hadn't lasted long; after the buildup I'd had, I was surprised that I lasted the two or three minutes that I did....

3 years ago
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The FavorChapter 9 The Third Cherry

I couldn't believe how dirty I felt. I was walking into my mother's room with no clothes on, cum dripping down my legs. As I was picking up the new tape, I saw a drop of cum drip off me and onto my mother's shoe. I thought about what Jeff had said: "you may scoop it up." I shivered as I walked out, leaving the spending of my first sex on my mother's shoe. I went back into my bedroom and I changed the tape. Jeff was already asleep. He looked so sexy, lying nude in my bed, surrounded by...

3 years ago
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Daughters Slut TrainingChapter 11 Watching Daughter Pop Her Cherry

Note: Thanks to wrc264 for beta reading this! Mrs. Umayyah “Leyla!” Kimmy shrieked when she opened her door. The blonde girl bounced on the balls of her feet, her braces flashing on her teeth. “Kimmy!” my daughter answered. The girls hugged each other like they hadn’t seen the other in weeks instead of at school just a few hours ago. They were so energetic, both of them making those excited noises only a teenage girl could make. I couldn’t help smiling while Todd Myers, Kimmy’s father...

1 year ago
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CherryPimps

I’ve heard Cherry Pimps come up during a lot of conversations lately. Sometimes it’s among the kind of porn enthusiasts I associate with or the horny fans who DM me asking for a review of their favorite paysite. I’ve even had a few girls mention the site to me when they came by for an intimate visit on the PornDudeCasting couch. I’m not usually this late to the party, and I knew it was about goddamn time to rectify that. The joint’s getting nearly a million visits per month, so I’d know it...

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3 years ago
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How IMORNERY81 Lost His Cherry

A young female friend on here asked me how I lost my virginity. I tried to describe it for her. I'm sure it isn't a unique story, but ... I decided to share it, not just with her but with all of my readers.----------------I can remember every detail of that first time! It was prom. I was Junior, she was a Senior. God I was a stupid, naive idiot!! It had been a wonderful night, lots of laughs, dancing, and the after prom was in a town not too far away. We had rented out a movie theater for the...

2 years ago
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Popping Janes Cherry

Well never mind my thoughts,. Now it was time to get ready for work. I needed to look sexy for my boss. So, I slid my navy laced panties on, after I pushed my butt plug into my ass and slid my vibrator into my wet pussy. I tossed the remote for my vibrator into my workbag. I always hoped that maybe one time, even if it was a random time, I might orgasm. So I tried with everything I had. Next was my awesome, lovely, custom-made bra. What's so special about it is that there are holes for the...

1 year ago
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Master pops his mommywhores anal cherry

It's been a few days since my sweet sub turned me from his mommy-dom into his personal fucktoy. He has really enjoyed his new role as my Master, as he has used my mouth and pussy several times already, he has made me crawl on the floor and beg for him to fuck my face. He has shot his cum on or in me several times per day.I'm in deep sleep in our bed, exhausted from the days activities, sleeping naked as my new Master has told me to do. Suddenly I feel something. I don't wake up fully, not...

Anal
3 years ago
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Nicki Picks Up Another Old Man And Loses Her Anal Cherry

After her pickup of Rick at the mall, Nicki realized that her ability to pick up older men was not exactly what she had originally thought. She had focused on dressing in a super sexy little outfit, and showing off her teen tits with a tight crop top, and a form-fitting mini-skirt.While her outfit probably helped, she realized that the fact that she was approached by Rick, and actually picked up, was more about her appearing to be distressed and vulnerable, and needing help. It was sitting in...

Hardcore
3 years ago
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My StepMum Convinces My Dad to Pop My Cherry

My father and mother had divorced as my mother recently decided to live with a man who organised work for women as call-girls or escorts.I live with my father as I didn’t feel safe with my mother's new partner. He had made a few suggestions to me about having sex with him, even though he was living with my mother. I am seventeen and a virgin. I have a job in an office in town.My father soon found a new partner, from the sounds that they were making in the bedroom, they had sex a lot. Julie was...

Incest
2 years ago
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Who took my Cherry

was really starting to develop strong feeling for him. I asked my Dad when would be the right time to go farther with him. Dad just said that I would know when the time was right. My 15 year old brother was also jealous that I was dating. I'd known for awhile he liked peeking at me whenever he could get a chance. Sometimes I didn't even mind, it may me feel attractive. It was a Friday night, I'd came home after another wonderful date with John. We kissed at the door when he dropped...

2 years ago
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A brother enjoys taking his lovely sister8217s cherry

“Billy, come here!” my sister loudly demanded. “I need a favor.” So I stopped what I was doing and crossed the hall, not wishing to anger her since she was a tyrant when she was mad. She was laying on her bed, naked, one knee raised and smiling at me. I blinked at her and waited, feeling my cock tremble. My sister is super hot, a high school senior with a killer body, a fine athlete and a real brain. She smiled at me and licked her lips. Her pussy lips were bulging out...

3 years ago
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Anal Cherry

Anal Cherry By: hardtimes69 Edited by: Monica Marshal,{obsessivelesbian} I would have never thought it would be possible to be on a euphoric high days after an exquisite cybersex session with a creative, gorgeous, sexy woman. I am still replaying our cyber lovemaking in my head. Some consider this crazy or bizarre behavior. I call it admiration, to be able to influence another sensual being think about their decisions and the direction to take when deciding a path to travel is a gift. I...

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