Teenage Boy Blackmailed By Neighbors Part 1 free porn video

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Across the street from Chris lived his friend Jason, two years younger than he. Jason had an older sister named Danielle, and lived with their divorced mother Christine. Danielle, two years older than Chris, was a popular cheerleader at the local high school and had great tits, a 36c, and an ass that would make any boy hard. With her long, dirty blonde hair, she constantly paraded around in nothing more than short shorts and a sports bra. But it was clear she got her looks from her mother. Christine, no older than 40, was a matured goddess. Beautiful brunette hair, a wonderful set of 36d breasts, and killer abs. Her and Danielle were known to go on long jogs through the neighborhood, much to the joy of its male inhabitants. Jason was often teased about his hot mother and sister.

Chris, who attended the local catholic school, devised a plan. He had gotten done early for a Christmas break, and was going to break into his neighbors house to see what Christine and Danielle had in their lingerie drawers. He knew Christine always forgot to lock their back door, so around noon he entered the house. First, he went to Christine’s room. It was exactly what he had imagined. His heart racing, he opened the drawers to find delicately laced bras, panties and stockings. He also found a few corsets and garters, and to his delite, he found Christine’s 10 inch, thick, veiny purple dildo. After carefully selecting an outfit, he put on a laced black bra with pink bows, a black laced thong, complete with a matching garter, stockings, and black high heels. He then went into the bathroom with a brunette wig he had found at home, and applied some of Christine’s makeup. Black eyeliner, foundation, all complete with bright pink lipstick. He then put some tissue paper in the bra to fill out his figure. “Damn. I look hot.” He returned to the bedroom and pulled out Christine’s purple dildo. It was time for him to become a full woman, a full fledged sissy boy. He laid on the bed, and spit on his fingers, as he prepared his tight hole for what was about to happen. Precum oozing from his semi-hard cock, he slowly entered one finger into his little hole. It felt so good, so right. Two fingers, three. He was ready for the dildo. He slowly let the purple, veiny toy penetrate him. He could feel his hole stretching, finally welcoming in the object.

He started to thrust harder, his hole welcoming in more of the dildo. He started to stroke his cock, and the pleasure was amazing. The deeper the dildo went, the harder he stroked. It was sheer ectasy. He was about to cum, and felt warm loads of his own juice shooting all over his stomach.
As he laid there catching his breathe, all Chris could think about was how he wanted more. “Im going to go to Danielle’s room. Its time for me to be a cheerleading slut.” He put the lingerie back in the drawer, and took the dildo to Danielle’s room. Her panty drawer was full of Victoria’s secret PINK thongs and g-strings. He found a nice matching neon yellow g-string with a bra top. The way his ass looked in the g-string turned him on so much. He found a pink bow to match his lipstick, placed it in his hair. He found some cheerleading sneakers and some pom-poms lying around and looked in the mirror. “Tranny sluts, we want it in the butt. Tranny sluts, come and lick our nuts. GOOO TRANNYS!” Chris cheered in the most feminine voice he could muster. He took the dildo and put it on Danielle’s bed, facing the mirror. His hole was ready this time. He moved the g-string over, and sat on the dildo. He was finally riding cock like a real woman, a real sissy boy slut. It felt so good in his ass. Now he was throbbing harder and harder on the dildo. He bent forward on all fours, and took all 10 inches of the dildo, holding it deep in him.

All of a sudden the door to the room opened, and he came face to face with Danielle. “Oh my god….Mom come here now.” She yelled. Chris could hear his friends mother running up the stairs. Christine and Danielle stood in the doorway staring at him for a moment. Then they both burst out in laughter. “Chris what the hell are you doing?,” asked Christine. As they walked towards him, Chris could only muster a simple response. “I wanted to feel like a woman. I don’t know it turns me on. “ They sat down on the bed next to him “Well,” Danielle replied, “you don’t look bad as a girl. Pretty cute actually.” “Yea and I’m impressed you could take this entire thing.,” added Christine, now noticing Chris had her dildo stuffed fully in his ass. “Your lucky Jason is at basketball now. Tell you what, Danielle and I are having a little get together with some friends this weekend, a Christmas Party. If you come over this Saturday and be our little sissy boy waitress, we wont tell Jason, plus he’ll be away all weekend at a tournament. Now Danielle, what do we name Chris?” As Christine finished talking, she grabbed the dildo still stuffed in Chris’s ass and started fucking him. “I don’t know mom, how about Chloe. Yea Chloe the sissy boy.” Danielle now started stroking Chris’s cock. “C’mon now Chloe, get that sissy clit nice and hard.” Chris couldn’t take it, he was so aroused. He shot his load all over Danielle’s hand. They both burst out laughing. “Oh wow, look at that little bit of cum. The girls will have a fun time with this mom.” Said Danielle. “Well now, the party starts at 8 o clock, be here at 4 on Saturday, don’t be late. You don’t want us to tell Jason now do you? And take my panties off, you sissy slut. See you Saturday.” Chris stripped naked, causing laughter from both Danielle and Christine, found his clothes and left. He was so confused, so embarrassed. But he loved it, and couldn’t wait for Saturday to see what they had planned for him.

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Blackmailed by Grandfather By billy69boyDuring the summer, when we were young, our grandmother used to invite her many grandci1dren to stay over for a few nights. She would host two of us at a time. Her five grown chi1dren were all married and had several chi1dren of their own, so there were plenty of us to go around.One summer, I was paired up with my cousin Cindy, who was a couple years younger than me. Cindy was a pretty little thing, blonde hair and blue eyes that always seemed to be...

3 years ago
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Blackmailed And Forced Sex

Hi everyone,me (ram) a naughty and good boy.An average body with a long and thicker dick (7 inch and 1.8inch).Coming to the story I got several mails from the readers of my before story which I was published.Some mail were fake and some were real .I got a mail from a name called divya. I was impressed about her comment about the previous story and started to chat very decently about her details and mine .After few days we become close started to sex chat …During one of the chat session I asked...

3 years ago
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Tony is Blackmailed and Forced to Become Tonya

Tony is Blackmailed and Forced to Become Tonya Let me tell you a little about myself. I am a nice looking 34-year-old male who has always had a very varied interest when it came to the sex department. In my younger days I had played around with many different aspects including BDSM, cross-dressing, bi curious times and the like. So needless to say, by the time I was 30 I had little interest in plain vanilla sex. With the ease of access to all these and other kinky themes via the...

3 years ago
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Diane Blackmailed

Diane Blackmailed ch 01by JustALittleRougherDiane looked at the cup of coffee and sandwich in front of her. She knew she had to eat something but couldn't muster the energy. Her arms were limp and she could barely keep her eyes open. Three more hours to go. Three more hours until the workday ended and she might be able to go home. If they didn't call."Bates!" She jumped at the voice. It was her boss, Mr. Vader. She turned around in her seat, looked up at him. "The Mitchell account. Did you...

1 year ago
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Blackmailed a young waitress in trouble

It was the come in mouth fantasy that gave me the most pleasure.   Celine’s silky golden hair made by belly tingle at the same time as her pink tongue played sexy games with the tip of my cock, circling one way then the other, flicking on the ridge and just under. One delicate little hand holding my shaft firmly, and my balls ready to burst, gently cupped and fondled in the other.   My wife Mildred was tossing. But I was too deeply into Celine to be disturbed. I squeezed...

Love Stories
3 years ago
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Cousins blackmailed by gardener

Cousin's blackmailed by gardenerThis incident happened long back when we had been to our grandparents place for our summer vacation. I was u******ed so I can’t tell my age. My mom’s younger sister too had come with her husband and her daughter Nisha who was 3 years younger than me, they had arrived a week before us. I was happy that I got company to play with the toys.One day, after breakfast, Nisha and myself were playing in the courtyard and suddenly Nisha with a mischievous smile on her face...

1 year ago
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Blackmailed Boy

Note : This story is completely fictional! My mother in law blackmail me into having sex with her..She seen my sister in law and i kissing and took pictures, later on i found out it was a set up.. i was trap, (My sister in law has a sex addition also she likes younger men, that god or she be screwing me too) My mother in law left my father in law because she was into wild and kinky sex and he could not perform. so this opportunity with me made her even hotter.. My wife works the grave yard and...

Incest
2 years ago
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Teenage Boy Has Sex With His Adult Neighbors Part Two

-We learned in Part One of this story that I was a sixteen year-old virgin boy named James, who everyone called Jimmy, with a very thick, nine-inch-long cock. My neighbor Norm was forty-two at the time. His wife Lindsey was forty-one and their son Todd was eighteen and away at college.I went with Norm to open his lake cabin for the summer. We were skinny dipping on an unusually warm day for spring in Wisconsin and he convinced me that we should masturbate one another on the boat. That evening...

MILF
2 years ago
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Teenage Boy Has Sex With His Adult Neighbors Part One

I’ve always considered myself lucky to have been able to grow up in the same house with an imperfect, but stable, family. My parents have the types of careers that allow them to stay in one place. Dad owns an insurance agency in a suburb of Madison, Wisconsin, and Mom owns a beauty salon. I always felt bad for the kids in school who were uprooted every few years while their parents chased their nebulous corporate dreams.After I graduated from college I married a beautiful girl that I met there....

Taboo
2 years ago
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Blackmailed Ch 02

A Literotica reader who sent me feed back on my story ‘Camping with Anna’ presented me with this challenge. ‘I want to see you write a story which is completely fictional. It’s more difficult than writing something based on events that actually happened, but you have complete free rein, and can explore your hidden depths and fantasies.’ Well I’m always up for a challenge so here goes. This is a fantasy from my hidden depths. I hope you enjoy it. The story takes up where ‘Blackmailed’ left...

3 years ago
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Blackmailed By My Teenaged Daughter0

Blackmailed By My Teenaged Daughter Teen, Group, Mff, Incest by po469 I am a happily married man of 38. My wife, 18-year-old daughter and I live in Phoenix. I fool around a little bit but what my wife Sue doesn't know won't hurt her. Sue was really into bridge so she is away playing cards several afternoons and evenings each week. This gives me time, when no one is going to be home, to go out and have some fun or bring someone home for a little romp. Maybe I fooled...

4 years ago
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Blackmailed

I show up where and when he told me to. He’s standing right in front of me. He knows everything, I know I’m about to be blackmailed but don’t know yet what he wants. First thing he does is tell me to hold both hands out in front of me. I figure he wants to see I don’t have anything in them but as soon as I do he slaps a pair of handcuffs on them. Before I can register what’s happening he’s gotten my cuffed hands over my head attached to a hook on the ceiling. Oh fuck! What just happened! This...

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