Losing My Virginity To Charlotte free porn video

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This all starts towards the end of my sophomore year of high school. I was sixteen, had my license, and a hand me down 73 Pinto. In high school, I never quite fit into any of the cliques in school. I had friends from most of them, but then there was Charlotte.

Charlotte was a month younger than me and hung out with the rougher crowd around. You know the ones, the smokers, the punks, and troublemakers. Really not my group, even with my broad selection of friends.

I met her through being a library volunteer. She got sent there for in-class detention. The librarian didn't particularly like the extra duty of watching over kids sent down for in-class detention, so she basically left them alone as long as they didn't cause her trouble.

So back to me a bit. I wound up working in the library as a volunteer to help with projects. I was into design drafting and could draw just about anything. So instead of sitting in the study hall, I worked in the library each day for one period.

Charlotte's first day there, I noticed her right away. She was close to my five-eight height, had dirty blonde hair, and looked pretty damn good in her tight cutoff jean shorts and t-shirt. Well, at least for a horny teenager, she looked hot as hell.

I also learned she had in-class detention for two weeks. Her first day there had actually been a Thursday, so she sat out in the library at a table by herself. The following Monday, the librarian had to move her into the little room where I worked on projects.

You see, the science teachers had this big class project going on and had reserved the library for their classes most of the day all week. This included the period Charlotte and I were there together. So, she wound up in my little room for her detention. I wasn’t exactly disappointed with this development. We got to chat all week and started a friendship.

Week two, she was banished back out to a table in the library itself, so I didn’t get to chat with her much more than to say hi. Yet a connection had been made. We had the same lunch period and started hanging out together. Granted, this was to the loud disappointment of some of her friends.

The First Date

About three weeks into us hanging out together, I finally asked her out. We went to a movie, and afterward, we had some time to kill before I had to have her home. Well, we found an out of the way place to park and started making out.

Well, one thing led to another, and soon I had my hand full of her breast. I remember she had very large nipples that got extremely hard when played with. Granted, this wasn’t the first time I had my hand full of a girl’s breast, but it was the first time I had a girl respond the way Charlotte did. She was moaning and wiggling as I switched back and forth between her breasts.

That was pretty much it for that night. I got to lay a little and then take her home. I have to say; I went home with a hardon that wanked pretty good that night. Later, I learned that I wasn’t the only one who went home and had to have a self-pleasuring session.

Our next few times getting together were pretty much a lot of the same. We both were getting excited, but neither of us was progressing to the point of providing each other with some relief. That was soon going to change, though.

The Relationship Heats Up Further

It was getting close to the end of school, and summer was coming on. The temperatures were higher each day. Well, I picked her up on a Saturday morning, and we drove out to one of the smaller parks in the area. Our plan was to make out and see how much further we could go with each other.

When we got there, there were several cars already parked in the lot. After a quick discussion, we decided to grab the blanket I had wisely put in my car. We went walking down along one of the trails. We eventually wandered off the trail to a spot all to ourselves.

I spread the blanket out, and we laid down. It wasn’t long before we were heavily making out. We were kissing and running our hands over each other when I ran mine up under her tank top. After that, it wasn’t long before her tank top was completely off, and I had her nipples between my lips.

As things progressed, I had my hand on my first naked pussy. As we made out, I played with her breasts and nipples; I worked my way to her crotch. I started out by massaging her through her shorts. Before long, I had her shorts open, and my hand on her pussy. First, it was with her panties between my hand and her pussy. Eventually, I had pushed her shorts down enough along with her panties to have my hand on her bare pussy.

She had a fuzzy bush of dark hair that matched the dark colors in her dirty blond hair on her head. I ran my fingers through it feeling her lips beneath. I played with her and had my first attempt at fingering a girl that day. I don’t know to this day how I managed to make it happen, but she orgasmed there on that blanket. None of the wild shit you read in stories, but she moaned lightly and clamped her legs on my hand until she calmed down.

Unfortunately, that was the climax of our day in the woods. I got to leave there with a stiff cock and no attention. My only satisfaction that day was leaving there with my fingers smelling of her pussy juices. After that, we had several encounters like the one described above, always leaving me sort of on the short end of the stick until one fateful afternoon on the flood wall.

After school, I took her home one day, and the apartments she lived in backed up against the flood wall. We had spent quite a bit of time on the far side of the wall. It was tall enough once you got down it about two-thirds of the way you couldn’t be seen from the apartments. It also had the benefit of backing up to a stand of woods along that stretch so that you couldn’t be seen by anybody from that side either.

We had taken an old blanket with us, and things kind of developed as they always did. It wasn’t long before her shorts were off, and I was playing with her pussy. I remember her being really wet that day as I fingered her. I was getting pretty good at bringing her to a quick orgasm.

I had gotten her off, and we laid there as she rested, kissing a little as we went, with her T-shirt still on but no bra; she never wore one. She had nice breasts but by sixteen-year-old standards, not large. She got on her knees and pushed me down on the blanket.

She started working my shorts off, pulling my underwear off at the same time until my dick was free. Of course, I was hard from getting excited playing with her. She grabbed hold of it and stroked it a few times. Damn, if I didn’t almost explode right then and there.

I thought finally I was going to get my turn. Well, I was going to get my turn but not the way I thought I would. As I laid on my back, she moved up until her pussy was right over my dick. I didn’t move a muscle. Honestly, I had looked at and read porn magazines while jacking off, but they sure as hell didn’t come with instruction manuals.

As I watched, she settled down on my dick. Oh my god, did it ever feel wonderful to be in her. She just sat there and looked at me for a few minutes. I was doing my level best not to do anything to make her get off of me. After what felt like an eternity, she started moving on me, not really riding me as you see in porn videos but just rocking on my dick.

We were like that for quite a while until she took my hands and placed them on her breasts. Well, I was slow but not that slow. I started massaging her breasts and playing with her nipples. She’d moan, and I’d moan a little.

Finally, she wanted more and rolled us over on our sides. I was on top of her with a little readjusting, resting between her legs with my dick back in her pussy. It was then she started encouraging me to pump into her. As you might guess, I didn’t last very long after that. Just as my orgasm hit, I pulled out and shot my load on the blanket below us.

We kissed and cuddled, but it was soon after that, the blanket got rolled up with its wet spot. Then we meandered back over the flood wall. By this time, her mom was home from work and wanting her to come inside to help with something. We shared a quick kiss, and I motored away in my Pinto, no longer a virgin.

She and I had sex numerous times, after that, in a lot of different places. To name a few, the Pinto's back seat on a few occasions, the flood wall, in the woods, and probably the most daring was on the picnic table at a small park one evening.

Things never really got crazy between us. It was always pretty much me playing with her, then sex, and we were done. It finally all came to an end about as quickly as it started. I developed other female interests, and then the stories I kept hearing about her. Let’s just say it was high school, and we’ll leave it at that. I moved on and gained new experiences along the way.

 

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Losing my virginity to Mary

I masterbated a lot during my youth and I still do, there’s nothing better than a good private wank.I stayed at my mates house whilst his parents were away and he told me to stay in his parents room. I used to love looking at women’s underwear as I’ve previously mentioned in another story so whilst I was in their room I decided I’d have a wank and snoop around to see what underwear my friends Mum ‘Mary’ had. I discovered some huge knickers and bras, Mary was a big woman, her breast size was...

3 years ago
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Losing My Virginity

I was chatting to someone the other day sharing experiences of losing our virginities. It was obvious, after a little while though, that we were talking about two different things. He was describing the first time he fucked someone whereas I, as a gay bottom, was describing the first time I had anal sex!In describing my experiences, I skipped the very first time it happened to me. Yes, I was curious and allowed it to happen, but it was not with someone I wanted it to happen with. It was more an...

Gay Male
1 year ago
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Losing My Virginity With Neighbor Natasha

Hi guys, let me introduce myself. I am Abilash 5″11 height , normal body. I am telling you about how i lost my virginity to girl named Natasha who is our neighbor. Before going to story you guys can give me feedback by emailing me to Now lets go Okay where to start….. This was about four years back when i was 20.I was a normal guy who likes girls… I always wanted a girlfriend.But couldn’t get. Not because i look bad(i look average actually) Even girls seems to like me. But i was afraid to...

2 years ago
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Losing Virginity Turns To Group Actions

Hi to ISS readers this is Shakshi. This is real story about how losing my virginity turned to a group sex act. Let me describe about myself. My height is 5’6. And my figure is 36-28-32. I was in 2nd year of engineering when this incident happened. My boyfriend was regularly forcing to have sex with me but I was a virgin and feared to have sex with him. So every time I was rejecting to have sex. Once he convinced me to have sex with him. It was the time of vacation after exams. His parents were...

3 years ago
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Losing My Virginity To My Colleague

This story is about losing my virginity and I’m Raghu 24 living in Chennai and my girl of my dreams Ankita ( name changed).It all happened one day when she joined my office. I was a manager and she joined under me. She had the assets of a bombshell.The women of crazy for sex (she wanted to keep her virginity till she got married). She was like 2 years younger to me and I started to talk to her and we became good friends. Mostly we work late till midnight ,so I used to drop her at her pg and...

4 years ago
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Losing My Virginity To My BrotherInLaw

Hi all readers, I am Artika and I am 27 years old, slim,fair and have a nice structure of 34c-28-36. I want to share you some of the events that made me fall for my brother in law (my elder sister’s husband [jiju]) and loose my virginity to him. My sister was married when I was in my final year of my college. The next year my nephew was born and I also completed my degree. Since I took a break after college days, I went and stayed with my elder sister to help her with the baby who was 6 months...

3 years ago
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Losing My Virginity And Becoming A Whore

Hey I am Ria, I am reading ISS from past few years and this has gave me courage to narrate my sex experience. Let me first tell me something about me. I am Ria from Ludhiana, Punjab. My stats are 34-28-32, height 5”7’ and I am of fair complexion. It is my first story so please excuse me for any mistakes. It happened 5 years ago when I was 18 year old and was living with my family in New Delhi. I always wanted to have a glamorous life and to become a model. I started to take participation in...

2 years ago
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Losing My Virginity

Losing your virginity is a moment in life that no one forgets. At sixteen, I had been going through puberty later than most, certainly later than a lot of my peers.I attended an all-boys school in south-east London, and in the first three or four years, I’d been self-conscious about getting changed for PE lessons because of my lack of pubic hair and small genitals, but by the age of sixteen, I had developed into a proper teenager who was growing a great body; however, I had no confidence where...

First Time
1 year ago
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Losing My Virginity to My Mothers Best Friend Part 4

I walked into the pancake house and looked to see if there was anyone I knew before asking for a table. I didn’t see anyone right off, so I motioned to the hostess indicating an open table by the front windows. This particular hostess just happened to be a senior at the high school I attended and one whom I only spoke to briefly between classes. She worked at the pancake house part-time to put away spending money for college.She was very cute, even in the hostess attire. She wore light makeup,...

Teen
4 years ago
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Losing Virginity To Chachi In The Car

This story is of a college boy Rohan who got to lose his virginity to his chachi. This story is based on true events and all the names are changed for obvious reasons. It was Rohan’s summer semester break. He was either working on his minor project or running an errand for his mom. He was the only child to his parents so he had all the privacy he needed. During summer, his cousin Riya would come to his place as it was well-furnished and they enjoyed their vacations together. This summer Riya...

Incest
1 year ago
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Losing my virginity

Let me tell all ISS readers that this story is told by my girl friend Rosie. I thought I should write how I lost my virginity. Loosing virginity is a big thing, no doubt. At the same time, I think, in our society too much stress is put on a girl being virgin till she gets married and the same is not expected of men. Okay, my story starts like this: After my sex lessons at my uncle and aunt, I started playing with my pussy during nights and put fingers inside and smell it. I was dying to have a...

2 years ago
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Losing My Virginity With My Maid

My personal maiden sexual encounter with a married lady I met online! Out to all those who had fantasies of fucking married beauties in their teenage! Hi friends and this is Gunjan here and yes my name sounds girlish but I was not asked my opinion when they gave me this and neither do. I have a problem with it fair and have athletic build and I’m 19 years old and currently in an engineering college in the NCR pursuing my B.tech. I had been fantasizing about women since class 6,specifically...

2 years ago
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Losing My Virginity To Sexy Neighbor

Hi, my name is Sakshi and like most young girls in India, I work in an IT company. This is my real sex story. Thankfully, I work in an international MNC and have a very good pay which allowed me to relocate from my hometown, the wonderful city of Bangalore. I am 23 years old and this was my first taste of freedom! I enjoyed Bangalore because no one bothered anyone here and no one knew me. I was hoping to get into some adventures here on my own. I was a virgin and I was hoping that I would have...

1 year ago
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Losing Virginity During Lockdown 8211 Part 1

Hi, this is Raj. 27. Software engineer. Well built body. I am a regular reader of Indian sex stories. But this is my first time writing one and it’s about losing virginity. It was the boring lockdown days. I was working from home, watching a lot of porn, and masturbating all day. I was still a virgin back then. But then miracles happen. After a few days, I got bored with porn and wanted something more. I even tried video sex with the Delhi sex chat (provided by this site). After a few more...

3 years ago
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Dear Charlotte

Dear Charlotte: I don't know if you remember me. It was so long ago, but also seems like yesterday. I had just bicycled from Kansas City to Toronto, Canada. I can still remember the smell of the fresh baked bread as I went through the Portuguese section; the stacks of fresh produce in the Chinese section and reading the newspaper headlines the next morning that Elvis Presley had just died. I remember trying to impress everyone at the cocktail reception at the convention we attended. I...

1 year ago
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Losing Virginity To Virgin Girl

Hi, Girls.. lets have my name as x_love, age of 22 from Chennai. 5feet 5″ height with a dick of 7″. This is my first story and my first experience. Please do mail me for your reviews. My ID is I am an fan ISS from past 4 years. I used to travel to my office in local bus in Chennai. Always its used to rush in morning and evening. During the travel accidentally used to hit on the bums of the girls and aunties on the bus and the story is about one of the girls. I boarded the bus and i saw a...

4 years ago
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losing my virginity

true story about losing my virginity - for the second time.I was pleasantly surprised when I met Brian. It was rare to blindly meet and find that they didn't lie about themselves over the phone. He was a tall, dirty blond with a lean frame and nice toned arms coming from his fitted white t-shirt. He had been totally upfront about who he was - and total party boy. I'm always attracted to confident guys and he had this in abundance. He was very sure of himself – a total turn on for me. There's...

2 years ago
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Losing Virginity With My Mature Girlfriend

The story is about me (Viraj), I was 23 and I had a fling with a girl name mary she was in her early 30’s. I was still a virgin at the age of 23 (not a joke) I worked at an MNC and been kinda ‘playing’ with mary, she’s in her early 30’s, very light skin for an Indian girl, about 5’6 tall, 160 lbs, she has a boyfriend that also work at pizza shop, mary and I never had sex, however she let me played with her tits from under her dress and touch her pussy from time to time while we’re alone in some...

3 years ago
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Losing Virginity To Aunty in Upstairs

We bought a flat in Bangalore recently and my father was getting some interiors works done. As we had college holidays, he wanted me to stay in this new flat for a week to supervise the finishing works. There was a temporary folding cot and bed there and good restaurants/mess etc nearby, so my parents considered to be a good experience for me to live independently. They never knew it also helped me in losing my virginity.I am 6 feet tall, but quite thin and also extremely shy by nature. Coming...

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