Shayna's LifeChapter 6: I Finally Lose My Cherry free porn video

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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. Or maybe I was :)
spanking partners - 0
my virginity - intact

Senior year - boys dated - 4
serious relationships - 1 (sort of, had to have a prom date, right?)
hand jobs given - approximately 6-7 (I was becoming more oral)
blow jobs given - approximately 14-15 (told ya)
spanking partners - 1
my virginity - intact

Yes, I managed to make it all the way through high school as a contradiction: a sexually-active virgin. My virginity wasn't something I was necessarily proud of. In fact, by the time I graduated my hymen was more a burden than I had ever thought it could become. I was ready to be deflowered, but I was still clinging to the idea that my first time had to be connected to a special event, like prom night, or graduation. There was no way I was waiting for a wedding night that might never happen.

Senior Prom. Could'a, would'a, should'a, but not for Shay. My prom date took me to a party after the dance, and I was in the mood. But the best laid plans... yada, yada. The dance had set up a very romantic atmosphere, and I had heard that the party we were going to was in a house with a lot of spare bedrooms and not much supervision. But my marvelous date had more on his mind than just the state of Shay's unopened honey pot. As soon as he got there he started drinking, and my romantic evening ended with him almost throwing up in my lap (good thing I have fast reflexes). I left him there, passed out on a sofa, and caught a ride home with a guy who was in the same predicament; his date had drunk too much also.

By graduation night, I had dropped vomit-boy, and wasn't dating anyone. But I almost lost my cherry that night anyway. Unfortunately, it was a scary incident that sometimes girls who should know better still manage to get themselves into. I went to a party with some friends, just looking for some fun and a chance to say goodbye to some people I knew I might never see again. I wasn't really looking to hook up with anybody. I was happy at that point in my life to be unattached. High school was over, and I was looking forward to college.

At the party I ran into a guy that I had known casually for a couple of years. He had been dating one of my teammates from the soccer team, but she wasn't with him. I asked him where Sharon was, and he told me she had dumped him just before graduation, saying she wanted to "move on with her life". He told me that "the bitch can go rot in hell for all I care". I know, that should have been all the warning flag I needed to stay away from him that night, but when he offered to give me a ride to another party that was supposed to be better, I took him up on it.

He was a big guy, a football player, full of himself, and used to girls doing anything he wanted just because he was a jock. He vented his frustration to me as we drove to the other party. I thought I was being helpful by just listening to him. I should have known that he would focus his rage for Sharon on me, but at that age I wasn't that smart.

When we got there, he confessed that he had always been attracted to me. I was just high enough to let him talk me into getting into his backseat. It was pretty daring, we were parked right on the street in a residential neighborhood about half a block from the house where the second party was taking place. Occasionally people walked by, either going to or leaving the party, but I didn't care. I was feeling a little wild and naughty. Also, I felt a little sorry for him, so I decided that I could make him feel better with a patented Shayna hand/blow job. It would be the first time I had had sex with someone I wasn't dating, but what the hell, it was grad night. Of course I should have known that he wanted more. I was really stupid to think I could get away with that tenth grade stuff with this guy.

He sprawled out on the back seat and I got on my knees between his legs. He had one of those big, ugly SUVs, so there was plenty of room. I unzipped his pants and pulled his cock out. It was huge, the biggest I had ever seen. I tried giving him a blow job, but it was difficult because of his size. He got impatient and pushed my head down on him, wanting me to take him deeper. But he was so big that it made me gag and I almost threw up on him.

That made him mad. He called me a bitch and a tease, and pushed me onto my back. He reached under my dress and tore off my panties. Then he was kneeling between my legs, pushing my knees apart. I knew I was in trouble. For the first time in my life, I realized I was going to be raped. Fighting him off was not an option, he was twice my size, and already had me pinned down. I couldn't even get a knee up into his balls. That might have driven him into a rage, but I didn't want my first time to be a rape and I was ready to fight. I was scared and furious at the same time. I only had one weapon left; the good old female standby... tears.

I started sobbing, and told him that I had pledged in my church that I would stay a virgin until I was married. OK, that was pure b.s., but he had no way of knowing that. Surprisingly, it worked, or maybe he just came to his senses and didn't want me screaming rape. For whatever reason, he sat back and said it would be OK if I just finished the blow job I had started. To my frightened eyes in the semi-dark of his car, the thing sticking out of his pants looked like the business end of a baseball bat. It wasn't all that long, but it was very wide.

He said "Do a good job, or I'll fuck you in the ass. Got it, bitch?"

Oh yeah, I got it. It would have been bad enough having that thing destroying my hymen, but I certainly didn't want it breaking my dark cherry either. I knew it was Sharon who he wanted to get even with, but I had put myself in the position of being the target of his anger.

I put my mouth back over that huge knob and started licking and slobbering over it. I figured if I could get it wet enough I might be able to get enough of it into my mouth to please him. I had always enjoyed giving oral sex before, but I was so scared then that I could hardly concentrate on what I was doing. After I had it sloppy wet, I started using both my hands and my mouth at the same time. He was more relaxed now and didn't try to push my head down again. After a couple of minutes of hard work, I put one hand on his balls and felt them starting to contract. I wasn't sure if he wanted me to swallow, but I took a guess that he was the type of guy who liked to cum on a girl's face, so I pulled back at the last second and finished him with my hands. Luckily, that seemed to please him. The good news was that he didn't pack a very big load in that weapon... a couple of spurts on my cheek and he was done. I used his cock to rub some of his semen over my lips and licked them clean. I smiled at him, trying to put on the best cum slut show I could. I was still scared and knew he was still capable of hurting me. He did slap me once, but not very hard. "You're just like Sharon, good for nothing," he said.

He gave me an old T-shirt he found in the back of the car to clean up with, and told me to get out of the car. He told me he didn't feel like going to the party now... but he was sure I could find somebody there to take me home. "There's bound to be some other horny guy who'll give you a ride for sex. Good luck!" He was laughing as he left me there on the curb. I felt like a total slut. The enjoyment and excitement of graduating was all gone. I just wanted to go home, and forget about this night.

I thought about calling my parents to come pick me up, but I knew how much trouble I would be in when they found out the whole story. I decided I had to try getting a ride from somebody at the party. I must have been quite a sight, with my hair all over the place and my clothes messed up. But I didn't care. I was just looking for a friend. By now it was almost 3:00 a.m. and a lot of people had left, and most of the ones still there were wasted. I was about to give up and call my parents anyway when I ran into Brad. Yes, that Brad.

We hadn't seen much of each other much over the last couple of years. We were still friendly, but since our breakup we had just drifted into different circles. He took one look at me, and took me into his arms. He didn't even asked what had happened, he just held me. That's when I lost it. Tough, self-reliant, take-charge Shayna was gone. What was left was the little girl that had been hiding in me for the last several years. I started crying and couldn't stop. I felt like such a helpless female... which I hate. Brad walked me over to a vacant sofa and we sat down. He hugged me again, and stroked my hair while I finished my crying jag.

When I finally got myself under control, I gave him a quick recap of what had happened. He knew the guy, of course, and swore he would get even with him for me. That was sweet, but unrealistic. Mr. Big Dick outweighed him by probably 60 pounds, and he was an athlete. Poor little Brad would have been pulverized. I told him not to worry about it, it was my mistake that had gotten me into the situation, and I would deal with it later (which I never did, one of the big regrets of my life).

Brad told me he would take me home. When we got back to my house, I leaned over and gave him a soft kiss, and thanked him for being a good friend. I will never forget what he said in return. "Shay, I didn't do it because I'm your friend. I still love you, and I will always be here if you need me."

I couldn't think of anything to say in return. I was in shock. I stumbled out of the car, snuck into my room... and lay awake for the rest of the night. I had no idea that Brad was still carrying a torch for me, and I didn't know what to do about it. I liked Brad, but I had to admit that I had never felt "love" for him, whatever that meant. I know now that is a problem for me. I have always had a hard time feeling deep emotions for the guys I date. Friendship, yes. Lust, most definitely. But true love? Maybe I just don't know it when I feel it, or I am looking for a romantic ideal that doesn't really exist in real life.

The summer between graduation and the start of college went by quickly. I had decided sometime during my senior year that I was ready to cut loose when I went to college. Girl Gone Wild, starring Shayna Simpson. I just felt like being a bad girl for awhile, and getting away from home and parents seemed like the time to do it. But first I had to get rid of my damn cherry. After all this time, I didn't want to lose it at a frat party or something stupid like that. I wanted to be a fully-functional woman by the time Fall term started.

But there was a problem of course, finding the right guy. The obvious choice was Brad, but I had waited too long. I gave him a call, to thank him again for being my hero, and maybe drop a hint that the treasure chest he had been pursuing for so long was ready to be opened. His mom answered the phone and told me that Brad had enlisted in the Air Force, to get some money for college, and he had left for basic training that morning. OK, if it couldn't be Brad, I decided I wanted a little adventure involved with my first time. If I couldn't have romance, then give me thrills. I was ready for a summer fling.

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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...

3 years ago
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No More Cherry

Characters: 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...

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...

4 years ago
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katia loses her bum cherry

She was bent over face down on the table, her tall legs keeping her ass up in the air. Her hands were tied to each of the further away table legs while her ankles were attached to the closest ones. Her face mask prevented her to see anything; it was darkness all round and only her ears could help her guess what was happening around. All her senses were heightened by the deprivation of her sight. She felt very vulnerable and humiliated being so unable to move and cover her nakedness, worse, her...

4 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...

1 year ago
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Chelle helps her sister lose her black cherry

Chelle had just found herself a new master, even though she had a boyfriend once she met her master Chelle just knew she could not pass up an opportunity to be stretched in every way. Her reality, her lust, her imagination and her sensuality were going to be expanded way beyond what she thought or even dreamed possible. Then there was the actual physical aspect of course underlying all the mental aspects. She would be taken from being an awkward slut to a deft whore who could serve even the...

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...

2 years 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...

4 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...

4 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
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...

4 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...

4 years ago
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Losing Her Girl Cherry

It was a sweaty, smoke-filled bar and I was grateful for the occasional waft of air each time an equally sweaty and seedy-looking patron came in or out.  I had been propping up the bar, dodging eye contact for nearly forty minutes, but the particular customer I was interested in hadn’t showed up.  Maybe my intelligence of their routine was flawed and yet – my sources had been reliable in the past.  I didn’t expect this one to be any different. I was being kept mildly amused by the proceedings...

Lesbian
4 years ago
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Losing my Cherry

Although l have been secretly cross dressing for years I have never took it beyond the confines of my bedroom or hotel room. Well I have been really wanting to take this to the next level. So as I was traveling on business this past week I answered an ad on Craigslist for a massage in my hotel room from a male masseur I made the appointment and waited with anticipation for my masseur to arrive. At promptly 8:00 there was a knock on the door and when I answered there was Chris a very...

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