Best Friend Surprise free porn video

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My freshman year in high school I met a girl I have known since and has made my life incredible.

Jane was a real free spirited, very pretty Jewish girl with fine shoulder length brown hair, a nice firm butt and a fabulous pair of tits. As the high school went on we became fast friends and along the way met Sally and Erica. Sally was an even more attractive Russian girl with wavy soft brown hair, a slim upper body small waist and the most awesome ass I have encountered to this day. Erica was a very outgoing, taller, attractive, uninhibited California girl with short brown hair, glasses and soft curvy figure.

Being a red blooded American boy I needed a girlfriend, Jane would have been my first choice but we were such good friends we talked and agreed it would have been a risk to try going out, Erica was feeling out high school at that point, into all the after school clubs and wasn’t into dating at that time but she suggested I ask Sally who, truth be told, seemed to need to have a boyfriend to be happy. Well as sophomores Sally and I dated for a while until she started seeing a senior, from the start she was the upwardly social climber. But through time we dated off and on, never going all the way but still making out with Sally was a good time. Jane was always there, she was my best friend, and with Erica helped me through my romantic ups and downs as we palled around.

During our junior year one afternoon while studying in my basement, Jane and I were both in the available mode when she took my virginity. We were taking a break from the books on the couch when she asked, ‘So have you done it?’

I knew what she meant and said ‘No’.

She gave me a wry smile, leaned forward to kiss me then said, ‘I figured, Sally talked a good game but she doesn’t put out. Well Kurt I think you need to get the experience and I want to give it to you.’

And that was my first time. Just having sex with Jane would have been a fabulous experience, a beautiful girl with an incredible body but we were such good friends and really cared about each other it was also a bonding experience which made it all the more special. And that was how our friendship continued and it was the best.

Jane and I were best friends but never exactly dated each other. We hung out with our friends, did homework and talked and had sex, which was a secret kept between the two of us. I guess it was Jane’s idea that we could have sex with each other so long as one or the other of us wasn’t dating someone else. Friends wouldn’t be part of cheating was the argument and while it wasn’t all that easy for a teenage boy to understand I accepted it.

Our senior year we both dated others off and on and I enjoyed the other girls I went out with but I do have to say an ever blossoming 38DD Jane was a dream.

At the start of the year my chemistry lab partner was Pam, a perky little cheerleader with the hottest body all of 5-2 tall and 100 pounds with long straight black hair. I never would have thought she was my type or that she would have the slightest interest in me since the previous year she was dating the studly baseball player who was class president.

But it seems that during the summer she got braces and that was a deal breaker for mister school perfect and they broke up. So when we started studying together I was just being a nice guy, having a girl as your best friend gets the message across that that works out better. Pam seemed to really enjoy that and we were quickly dating. Luckily for me that progressed to making out and then having sex so I must say high school was ending on a very high note.

Near the end of the year Pam decided she was going to go to a university in Utah of all places and with my choices limited to that city branch of the state school we ended our relationship but on very good terms.

The girl I really fell for was Erica who I had known since freshmen year but only started dating right before graduation. Erica at 5-9 was a little taller than Jane she had a great body 36D chest a narrow waist and wide hip. I always thought it was very sexy how her jeans were tight on her nice full butt while the waist band was too big and loose around her waist, we both enjoyed it when I would tuck my hand in the waistband of her jeans when we hugged, it was almost grabbing her ass.

How we got together was a little odd. Erica eased back on the school activities and we were hanging out a lot when I just asked her, ‘What would you think about dating me?’

She laughed which I didn’t take as a good sign but then she said, ‘I thought that was what we were doing.’ Then she hugged me, rubbed my back as we were nose to nose and said, ‘If we get the first kiss out of the way we can move to having sex if you’re game for that.’

I put my arms around her waist and kissed her, Erica took my head in her hands kissing me back with her tongue twirling in my mouth. And we got it on.

Erica was still unique. Everything and I mean everything, would be great for 6 or 7 weeks and then she’d get moody, say she needed her space and give me the old ‘it’s not you it’s me’ bit and we’d break up. If I didn’t know Erica I would have been upset but she searched for different things when we started high school and it seemed as though she didn’t want to get pinned down without having the chance to explore. So we did the break up bit, I let her do her thing and in a month she would want to make up, with the great make up sex and things went back to great.

By the Christmas break that first year of college there were some changes in Jane that I sensed and some I really didn’t even notice. In those periods where Erica and I broke up and we were both unattached and in the mood, Jane and I still had great sex. What I did notice was that Jane still had the most incredible body, her legs remained firm, her ass high and tight and her breasts grew progressively and incredibly. By the time our senior year began she was a mouthwatering 38EEE. Which is about the time I discovered what I had been oblivious to was that Jane seemed to keep getting her hair cut shorter until it was actually shorter than mine and mine wasn’t all that long, her jeans were as tight as ever and she had the ass for tight jeans and her wardrobe was dominated by flannel shirts.

It was the most shocking day of my life. We were in Jane’s bed taking a break for air. Her parents were gone for the day. Jane climbed up sat on my stomach and said, ‘Kurt I’ve got to tell you something very important.’ So I listened, ‘I have come to the realization that I am a lesbian.’

To say the least I was shocked and it took a while for me to comprehend what Jane had said, what it meant and how it affected me but did so before I spoke. ‘Jane, you’ve been my best friend.’ I said stroking her thighs, ‘And no matter what I want you to know I will never want that to change, I’m there for you, I’ll support you and always be there for you. I guess this means we won’t be doing this anymore but you are the best lover I have ever had and I’ll never forget the times we shared.’

Jane looked at me smiling then leaned down putting my face in her ample cleavage and tit hugged me, ‘That’s why I love you so much, but we’ll still have sex silly.’

I must have had a look on my face that was as puzzled as I was, lesbian, would mean sex with women not men like me. ‘Oh Kurt our making love is the ultimate way of expressing the closeness of our friendship. Having sex is our way of showing the love and support we have for each other as the most important person in each other’s life. I’d never want to end that.’

I may be a dumb guy and I knew what I heard and it didn’t make any sense but it quickly registered, Jane now a lesbian, we still have sex, all is good so who am I to try to make sense of it. And we spent the remainder of the afternoon fucking our brains out.

And my life went on from there.

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It's the start of your senior year, and things are going great. School is a breeze, and you're lucky enough to have been with your girlfriend Jane for almost a year now. You two are in love, and you've never been happier. Jane is what most guys would call "cute" -- not particularly curvy or anything, but on the smaller side with a pretty face framed by her brownish-blondish hair. She has smallish B cups and a nice ass -- plenty to keep you happy, but it does leave you wanting more... She's...

2 years ago
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Being watched by my boyfriends best friend Pt 2

Well that night made a bit of an impression on me; I'd always been quite reserved. For example, if we ever went on holiday, even with the girls, I always stayed covered up. But after that night with our friend, I developed a bit of an exhibitionist side. We spoke the following morning, as I'd said, and agreed that we would never mention it in case someone picked up on our conversation. Although he did remind me of the promise. And true to his word, whenever we were out, if there was anyone...

Exhibitionism
2 years ago
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My Girfriends Friend Shayla

I walk up to the door of my girlfriend’s apartment. As I start to slide the key into the lock, I can hear slight muffled noises from inside. As the door slowly opens, I am met by the sight of my girlfriend laying with her legs spread wide open on the couch and her super sexy friend Shayla, who I’ve always wanted to see naked, on her knees eating my girlfriend out. Shayla’s tight ass looks so incredibly sexy with that hot pink thong on.I shut the door behind me and walk up to the couch as I get...

4 years ago
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Best Friends New Pleasure

Rachel jumped into the pool, feeling the cold water wrap around her body. Mark followed her in, diving deep into the water. He rose up to the top of the water, just as the volley ball flew into his head. Rachel sat there laughing, until Mark swam over to the ball, grabbing it, and flung it back at Rachel. She ducked out of the way and quickly swam for the ball to send it back at Mark. She grabbed the ball, turned to Mark, and began arch back to throw it. Mark paused. His eyes were fixated on...

First Time
1 year ago
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Best Friend Milli Becomes NUDE Model For Painting Course

It was another boring day at college. Drawing the objects kept on the table seemed FINE ART to the faculties here. Why don’t they understand I have taken FINE ARTS to make FINE PAINTINGS not to waste my time on basics which I have learned in the past. Let me introduce myself to you. I am Ravi, a fine arts student in a reputed art college in my region. I always had a passion for art and paintings. I lived far away from my home in the college hostel. I went against my family’s wishes and chose...

1 year ago
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Best Friend Milli Becomes NUDE Model For Painting Course

It was another boring day at college. Drawing the objects kept on the table seemed FINE ART to the faculties here. Why don’t they understand I have taken FINE ARTS to make FINE PAINTINGS not to waste my time on basics which I have learned in the past. Let me introduce myself to you. I am Ravi, a fine arts student in a reputed art college in my region. I always had a passion for art and paintings. I lived far away from my home in the college hostel. I went against my family’s wishes and chose...

3 years ago
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Best Friend with Benefits

This story is true. Its been many years and so the conversations are what I recall and not verbatim. I had never thought of myself as gay or anything other than straight. In my youth the word gay only meant happy. There were only two ways of describing a man’s sexuality that I was aware of, straight and fagot or queer. I am sure bisexual was used then but that was a word I was not aware of when in high school. I had done things sexually I knew where frowned upon but never considered them...

3 years ago
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Best Friend with Benefits

This story is true. Its been many years and so the conversations are what I recall and not verbatim.I had never thought of myself as gay or anything other than straight. In my youth the word gay only meant happy. There were only two ways of describing a man's sexuality that I was aware of, straight and fagot or queer. I am sure bisexual was used then but that was a word I was not aware of when in high school. I had done things sexually I knew where frowned upon but never considered them...

4 years ago
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Best friend had a dark sexy fantasy Chapter 1 The Beginning

Growing up wasn't too hard. You see, I was raised in a pretty decent sized town. I was an only child so I didn't have any siblings. I found out when I was 14 that I was adopted from a family that lived in the Polynesian islands. My biological parents were both native to the area they lived in, but they were hooked on Ice which seemed to be the drug if choice in that area. According to my adoptive parents I was adopted when I was born. My biological mother had given birth to me while she was...

2 years ago
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Visiting my boyfriends friend

For those that have been following the story, you now know about my exhibitionist side. For newcomers I could re-cap but it would be easier and hopefully better for you if you read my previous stories. However, I shall bring you all up to speed with what happened in between the last story and this one. After the holiday things went back to normal for a while. Then out of the blue, my boyfriend and his friend both moved away with their jobs. They weren't connected, it was just bad timing (for me...

Masturbation
2 years ago
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Best Friend Cuckold Me And Fucks My Bitch Wife

Hi reader, this is my fantasy story of getting cuckold by my huge dick friend and my wife willingly taking it! My name is Morgan. I am 27 years old. I am an average-built guy with a slim and tall body. I got married recently. About my wife, her name is Katy. She is a little dominant type but she is not used to doing it with me as I am the leader of the family. My wife is short and slim with a perfect body. Her tits and ass are round and perfect for her short height. No guys will leave a chance...

4 years ago
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Girlfriends Shemale Surprise

As Carter finished unpacking after dinner, he couldn't help but smile. His last summer before having responsibilities would be spent in the beautiful home belonging to his girlfriend's parents. Carter and Chloe had only been dating for a few months but were both entirely consumed in the early parts of their relationship. From hand holding to mini-golf the young couple was infatuated with one another. The one area where things had not quite progressed as Carter had hoped was the physical aspect...

Transsexual
2 years ago
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Bestiality Dreams Night 1 The Cat

It had been mere hours since the appearance of the first symptoms and already the family doctor had given orders restricting me to my bed. Under normal circumstances, I would have been thrilled at the thought of missing a few days of school, but, given my extreme fatigue, enjoying my time off was impossible. No matter what I did, be it watch TV or read a book, I kept nodding off. And it was still quite early. In a final attempt at resisting sleep’s inviting embrace, I did something I knew...

2 years ago
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Bestiality Dreams Night 1 The Cat

Introduction: A young woman dreams of having sex with a cat! Modern medicine cannot explain what happened. Many doctors tried, but none could identify the ailment that afflicted me. Their only recourse was to identify my symptomsextreme fatigue and deliriumand suggest extensive bed rest and a high fluid intake. They were equally dumbfounded by my miraculous recovery. I remain similarly uncertain as to the nature of my peculiar illness, yet I will forever cherish the memories of those ten days I...

2 years ago
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Best Friend Forever 4

-*- I had gone to bed by myself and woke with Lisa in my arms - her eyes were open and she looked so innocent, so delicious. I kissed her. "Good morning brother-dear." "Good morning Lisa." At that moment I recalled the day before - the long torturous and very sexy lesbian shows choreographed by Gerald. I had ordered Amy to see to mother, as she was in great pain from the spanking as well as the general abuse, dildo's and butt plugs the night before. Lisa had been...

2 years ago
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Best Girlfriends Forever

Best Girlfriends Forever Chris falls in love with his new roommate Shannon, who is transgender. Shannon falls in love with Chris too, but she already has a boyfriend and instead wants to be 'best girlfriends forever'... * * * Chapter 1: "Just two more questions." "Sure," I responded cheerfully. It seemed like Shannon and I were connecting which was great because I desperately needed a cheap place to stay. And besides, who wouldn't want someone as cute and beautiful...

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