Sisterhood of Sin 18 The Entrapped Man
- 3 years ago
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Hello ISS reader,
Today I am going to tell you my best friend jimmy’s story. jimmy and I studied in same school in pune…
I guess the best place to start is at the beginning. Kate was one of those girls in school that got the attention of most of the boys since the sixth grade when her breast suddenly popped right out of her chest. She was a little embarrassed by them the first day at school when all the boys stared and pointed like she was something from outer space or something. She wasn’t sure what all the commotion was about but she did enjoy being looked at by jimmy the love of her life since the second grade who didn’t even know she was alive until now. How strange all of a sudden he would start talking to her and asking people if she liked him. He knew she liked him, she had stared across the classroom with her best smile at him for years and now he has finally noticed her.
It didn’t take jimmy long to talk her into letting him see and even touch her breast and if the nun hadn’t caught them behind the school that day things might have turned out different for Kate and oh god what a day that was! It turned out that was the only time she had ever been touched my a man and she held onto that memory for years to come because Kate got the calling of the church shortly after that day and became a nun after graduating. She taught at a catholic school a short distance from her home town and enjoyed teaching history and helping with the girl’s basketball team. The team had the second best record in the state and tonight they played her home town school St. Francis for the championship.
The whole town was up for the big game, even sister Kate was excited which was rare being a very low keyed person who didn’t show a lot of emotion. She made sure all her daily duties were taken care of well in advance of the game so she had plenty of time to relax before game time and when she relaxed her mind wondered to things she wished she had done and didn’t. Like getting to feel jimmy like he had felt her and knowing the pleasure for making love. Her only experience with sex was with her own hand in the tub alone. She could remember even to this day the burning inside her when jimmy’s fingers touched her swollen nipples, her breath quickened as he squeezed her fleshy mounds and the tingle between her legs would haunt her to this day.
She laid back into the warm water as her fingers traced a circle around her nipples making them very sensitive to the touch. She softly pinched her left nipple sending a spark of desire through her body. Her soft moans unheard by anyone filled the room as her finger rubbed her clit. She knew the exact spot to apply pressure to so her climax would be quick and satisfying. She always felt strange afterwards but she needed the release of sexual tension so she could keep her emotions in check.
Kate ran down the stairs to the locker room and helped the girls get ready. She led them in a prayer and blessed the game ball just to be sure they had an edge. The couch led them into the gym with the crowd solidly behind them with cheers and pom-pom’s waving in the air. The excitement was over whelming as the other team made their way in. Kate looked the seats over for people she knew with little luck until she saw the one person she hoped she would never see again. God he was still the best looking thing she had ever seen and he was heading straight towards her. Kate didn’t know what to do, could she face him without busting into tears or maybe even doing something worse like fainting.
“sister Kate, how nice to see your again after what has it been ten years?” he said as he held his hand out to her.
“jimmy! Yes I believe that’s right, how are you? You are still looking good too!” she cooed trying her best to be happy he was there as she shook his hand.
“thank you sister, I don’t know if I’ll even fell right calling you sister Kate. I mean we grew up together and all, you know what I mean?” he babbled trying to keep from looking like an idiot.
“I know jimmy, you can just call me Kate like always its fine with me.” she said feeling her face grow warm from blushing. She held his hand firmly as she looked into his eyes, the eyes that once viewed her naked body was again looking into her soul.
“Kate your still the prettiest nun I have ever seen! Those blue eyes just get brighter and brighter!” he said searching her face for a reaction to his compliments.
“now jimmy your still the smoothest talker in the state I see, but you can’t talk the habit off me.” she said with a big smile almost daring him to try.
The buzzer sounded for the start of the game and Kate excused herself to help with the team. The game went well for the first half and Kate managed to keep her mind on the game and not jimmy seated directly across from her. The half came and the teams were tied 36 each. The second half wasn’t going as well with them being down by six points. Kate prayed for a victory as the seconds ticked off the clock, she looked across at jimmy that hadn’t watch a second of the game only her.
“sister Kate would you please go to the locker room and make sure the girls have clean towel for after the game.” the coach said watching every move on the floor.
Kate nodded and headed out of the gym towards the locker room. She staked the towels near the showers and made sure all the girls had wash rags and soap before heading back to the game. She hurried thru the hallway and pushed the door open. Bam!
“ouch! Shit! You broke my nose!” she heard from the other side of the door.
Kate quickly pulled the door open and saw jimmy standing there with blood running down his face, his hands covering his nose and tears running down his face.
“oh my god! Your hurt! I am so sorry! I was in a hurry I didn’t know anyone was there! Please forgive me jimmy!” she said taking his head between her hands.
“let me see how bad it is!” she said pulling his hands down and looking at his bleeding nose.
“come with me! I’ll get you cleaned up it doesn’t look broken, you’ll live I think.” she said pulling him into the boys locker room. She led him to a sink and began cleaning his face and nose.
“now that’s better, looks like its stopped bleeding and you’ll be fine.” she said relieved it wasn’t broken.
Jimmy stood up and staggered slightly, Kate held him firmly against her to keep him from falling which was the wrong thing to do. His hand landed firmly against her breast by accident and his touch sent waves of passion thru her like a volcano exploding. Kate tried to ignore it but she couldn’t, even though he had regained his balance his hand remained firmly on her breast.
“are you ok?” she asked with a tremble in her voice.
“I think so, I was just a little light headed there for a minute.”
Kate moved her hand to his and slowly moved it off her breast, she looked up at him with a smirk on her face as if to say you got your feel now what? Jimmy just smiled before he leaned down and kissed Kate’s hand.
“thank you for helping me Kate, I didn’t mean to grab your tit, really I didn’t.” he pleaded
“yeah I know it just always ends up on my breast doesn’t it.” she said with a smile
“well hell Kate you still have the best tit’s I’ve ever felt and you know I never got the chance to show you mine like we agreed on all those years ago.”
Kate broke out laughing at his remark which was true, she was amazed he remembered.
“you know if that nun hadn’t caught us who knows what would have happened?” he said with a giggle
“yeah your right, I might have liked what I saw if I got the chance to see it.” Kate said with sarcasm in her voice.
“that you might! Well I think its time for me to pay up Kate.” he said undoing his belt.
“oh no you don’t! I won’t look! Stop right now jimmy!” she said covering her eyes.
“Kate when I owe I pay up! With that he dropped his pants to the floor and pulled up his shirt exposing himself to her fully. His cock semi hard from just the thought of a nun seeing him much less Kate.
Kate couldn’t help herself and peaked through her fingers to see seven inches of hard cock standing straight up. Her eyes almost popped out of her head at the sight of it, this wasn’t her first but sure as hell was the biggest she had ever seen.
“you can touch it you know? That was part of the deal.” he said taking her hand and placing her soft fingers around the shaft of his throbbing cock.
Kate didn’t say a word while she let him place her hand on his cock. Stunned wouldn’t be the right word, excited couldn’t compare to the emotions running through her at that moment. She tried to pull her hand free without really trying. He moved her hand up and down his cock while looking her in the eyes knowing she wanted him as bad as he wanted her maybe worse.
“I can’t do this jimmy! She said meekly.
“you can and you will!” he said pulling her to him. His lips touched hers and she returned his kiss with more passion than he thought was possible. Kate’s hand started moving on its own as his tongue entered her mouth darting against hers in mock battle. His hand went to her and she moaned into his mouth as the desire swept through her. Kate was lost in lust for the first time in twenty eight years and she couldn’t stop now even if she wanted to and she didn’t. His hands melted into her flesh it seemed as he massaged her firm full breast. He could feel her nipple through the material as it strained against his hand. Kate felt her knees weaken as her passion grew; she dropped to her knees and took his cock into her mouth just like she had dreamed for years. She licked his cock shaft as her lips tasted every inch, she could feel the moisture running down her thigh as her pent up sexual desire swept through her body. Her fingers caressed his aching balls as she opened her mouth allowing him to fuck her mouth as he pleased. Even though this was her first time it seemed so natural almost like she had done it many times.
Kate felt him pull her up with one hand and the other bringing her habit up. She felt the cool air against her hot skin as the material left her body exposed. She raised her arms allowing it to be removed fully exposing her body to him. Jimmy lowered his mouth to her nipple, nibbling on it as he sucked it firmly into his mouth. Kate loved the feeling of his hot breath against her breast as he suckled and nibbled on her nipple. His hand wondered down between her legs, she jumped as his finger slipped inside her panties and touched her. She moaned softly as his finger entered her, she felt her passion boiling over as he moved his finger slowly inside her until he felt her vagina contract around his finger. He knew she was beginning her first orgasm and he pushed his finger in deeper stroking her clit as he fingered her. Kate’s moans began to get louder as she felt her body exploding; she quivered as she released herself to his control.
Just as Kate’s orgasm subsided jimmy maneuvered her to a bench laying her down so he had perfect access to her. His tongue traced a line from her knee cap upwards to her now flowing wet vagina. His tongue licked her fully across her swollen pussy lips; he nibbled on her clit as it stood up proud and erect. He sucked it into his mouth and flicked it with his tongue making her whole body jerk with pleasure. Kate was overcome with desire and pulled his face against her convulsing pussy. Kate exploded into orgasm after orgasm as his tongue worked its magic. Kate couldn’t wait another second, she wanted his cock inside her and she wanted it now! She pulled him on top of her and told him in a low husky voice she didn’t even know existed.
“fuck me now! I want you deep inside me jimmy!” she begged for what she had never had but dreamed of her whole life.
“I’ll fuck you baby! Nice and slow I’ll fuck you!” he said between clinched teeth.
Jimmy positioned his cock and slowly pushed forward, he could feel her pussy stretching as his cock head pushed through and enter her virgin pussy. He stopped when she cried out in pain.
“don’t stop baby! Please don’t stop I want you so bad!” she said with tears of pain and lust running down her cheeks.
“I’ll go slow baby, just relax ok.” he said trying to comfort.
He pushed more of his cock inside her and bean to slowly fuck her, giving her time to get accustomed to his cock. Little by little he pushed more of his cock inside her until he had almost the entire length in; he slowly picked up his pace until she grabbed his ass cheeks and began pulling to her. Kate’s eyes were glazed over as she felt her first cock induced orgasm rock her world.
“fuck! Oh fuck! I’m cumin!” she squealed as she let herself go to the desire that crashed through her.
Jimmy slammed his cock fully into her hard; she fucked him back by raising her hips to meet his trusts. Jimmy panted as he fucked her harder and harder feeling his own orgasm building inside him. He could feel the tightness of her pussy holding his cock like a hand firmly in place. He pumped harder feeling his cock pushing against cervix as he plowed deeper and deeper, harder and faster until he shot his hot load of cum deep inside her. Kate yelled out loudly as she felt his cum fill her vagina.
“oh yes baby! Oh god yes!” she screamed!
The door to the locker room opened and there stood father Matthew.
“what the hell is going on here? Sister Kate! Is that you!
Thanks for reading my friend’s story.
Lucky & jimmy
Write me girls at
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sister Love – Strap-on FantasyBy billy69boyEmma found herself smiling as she drove to the airport to pick up her little sister Amy. The two girls were very close, despite the disparity in their ages. They really missed each other, and now they were going to spend the entire summer together.Emma was proud of herself. At 20, she landed a good job, and she could afford her own place in the city. She was finally on her own; free to call her own shots. Funny thing, though, she was only away from her...
sister Love – Strap-on FantasyBy billy69boyEmma found herself smiling as she drove to the airport to pick up her little sister Amy. The two girls were very close, despite the disparity in their ages. They really missed each other, and now they were going to spend the entire summer together.Emma was proud of herself. At 20, she landed a good job, and she could afford her own place in the city. She was finally on her own; free to call her own shots. Funny thing, though, she was only away...
The SecretKurt hadn't heard from Nicole for several weeks after their torrid night together. That was a good news, bad news situation. Although he hadn't gotten a message from her, apparently Nicole wasn't pregnant. He had been anxious about that possibility during the whole time he hadn't heard from her.Like most people in that town, Kurt was at the high school stadium to watch the Fourth of July fireworks. Everyone was there including Nicole. She spotted him and waved. He walked toward her...
Seduction"Did we do anything wrong, Beth?" I'm standing naked in the basement of the new local Sapphire Club as Bethany and Marta, one of the members of her black team that helped with the rescue of Chelsea, are searching through my trunk, trenchcoat, mask, and even my hair to make sure no tracking devices were planted on me during the session. They find nothing and I dress in clothing that stayed in Bethany's care while I exposed myself to the students and burqa babes. "I don't think so. I think we...
LesbianIt was quiet in the chapel. Serene. For some, the stillness, the lack of breathing, the rustle of clothing, would add to the serenity. In reality, it was just another indication that they were dying, and not just them, the entire church. Sister Magdalene looked up, the figure of Jesus Christ predominant behind the small altar. She knew every nook and cranny of the chapel, having cleaned it more times than she could recall. Twenty four years of her Twenty seven years, she had spent here in...
Hello, my name is Ajith. I have one younger sister. By looking at her bra, hanging in the bathroom, I came to know that her bra size is 38. Yes, my sister’s boobs were huge and firm and not sluggy. We both lived a normal brother-sister life. Even though I had incestual feelings towards her, I never tried anything with her. I just use to masturbate thinking about my little sister’s cleavage which she accidentally showed while sweeping the floor. Things went like that. One day my parents went for...
IncestIn the late 60’s when I was 16 years old I lived in upstate New York. My dad got transferred by his company to Miami. It was a big promotion for him so he didn’t want to turn it down. We were three k**s in the family. There was little sister my big sister who was three years younger than me and me. I was in my first year of high school and did not want to leave my friends behind to start in a new school in Miami. It took a lot of convincing but with the help of my grandparents I was able to...
My name is sameer and I live somewhere around the Hyderabad. I’m tall and I play basketball at my school. Both my parents are also tall as well as my sister and so whenever we go out to places people look at us somewhat awkwardly. Anyway, I was just heading back to school. Since I’m on the basketball team we are usually pretty busy but since it was the first couple of weeks I didn’t really have much to do. One day my sister, hanisha, called and asked if she could come down to see me. Now I had...
IncestFiction with made up charactersHi, my name is Ryan and I'm a 22 year old student. I live with my parents as my university is pretty close to where we live, and I have a pretty big room of my own and get all my cooking and laundry done by mom, so I'm in no hurry to leave.I have a younger sister named Magdalena, or Mags for short. She's 19 years old and is about to start at the same university. I've always had a strained relationship with Mags, as we were the only two k**s in our family and we...
Hi friends. This story is a true one and being shared to you all that how things changed between me and my sister and we indulge in a nice and pleasant sex life. I hope that you have read story Innocent sister love turned into sex posted on ISS on 8th March 2012 under incest category. This story is little bit long but I am not only sure but confident that you will enjoy it (provided you visualize yourself in my situation) good luck. Again let me mention that and I’m Rahul age thirty and living...
IncestThis went on and on, each taking their turns and with me getting them ready. I have to tell you, I don't know which I enjoyed the most the anal intercourse or the vagina intercourse. I can tell you, I just loved sucking them and getting them ready each time. I lost track of time and I am thankful Harry didn't. He made an announcement While I had Jim's cock in my mouth working it nice and hard "OK Jim, your the last one, Sister has to get going before she is missed" I was lost in my lust,...
I'm a 30 year old male, married to my 25 year old wife, who has an older 35 year old sister. My wife and her sister are very similar with their looks and physique. My wife is around 5'6" of slim athletic build, her sister is slightly shorter, say 5'4" and quite petite. We have holidayed with my wife's sister on several occasions over the years so I've gotten to know her body quite well, seeing her regularly in a bikini and summerwear. Given that she looks so similar to my wife, I...
This is my first story so please leave comments/reviews and tell me what your favorite part is. Also feel free to send me links to similar content.Everytime my wife and I go to visit her parents her sister will randomly decide to come visit as well. We had been at the house for about a day when my wife and her mother decided to do some shopping in town. Not being my thing I elected to stay behind and use my off days to lounge around.Upstairs at my wifes parents house there are three bedrooms,...
Sister, Girlfriend, And Fuck Buddies Veronica was sixteen years old, she could drive a car, and she had a job as a cashier at the local drug store. In other words she was a responsible adult…so Mom and Dad left her in charge of me for the weekend while they went off somewhere. The first thing Veronica did was call all of her girlfriends and tell them to come over Friday night around dark. Then she told me to take some food, drinks, and movies to my bedroom and stay there. At...
Even though he's been married for almost a year, Tim is horny most of the time and jacks off in front of his computer quite frequently. He loves his wife. They grew up together, have always been best friends and are compatible in every way, except sex. Tim has the libido of a healthy 26-year-old male, but unfortunately his wife, Sharon, was raised to believe that sex is dirty and disgusting, something only done as a monthly obligation. It was drilled into her, from the time she was old enough...
--- Stepsister Sleepsexing Surprise (MF, inc, nc, oral, impreg?, reluc, safe, viol) by Krosis of the Collective --- I opened my apartment door and let my sister in. As she shuffled past I noticed a bruise under one eye. I didn't ask. She had called me out of the blue a few hours before to ask if she could stay with me for a while, and now I was pretty sure I knew why. Regina (I call her Reg) was a big woman -- not fat, but tall and proportionate -- an Amazon with an hourglass...
This is a true story as told to me by my swinger friend RonJohn. Enjoy! My sister is four years older than me. We have always been close growing up. I must say that I have always loved women-and I mean from my earlist memory I can recall always trying to see my mom, sister and any other woman naked. I would walk in on mom right as she was getting out of the shower, suprise my sister when I knew she was changing clothes. I would pop in on granny when she was in the bath. I even peaked at some...
I had just come back from college as I had a bad headache. My sister Arti usually comes back after 7 pm from her work. So I expected to find the house empty as my mother had gone on her school trip to Guhati but to my surprise, Arti’s was already in her room as I heard her moans. I thought she was in pain but as I went closer, I heard my sister’s sexy groans and a man’s voice mmmmmm Arti you are so sexy your pussy is soo tight! I saw inside her room only to see my sister bent forward and a man...
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