Jack and Jill
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Brandi had been a babysitter, like, forever.
Her Dad was a Gynecologist. He had his own private practice in a Doctor's office park not far from their home. All of Brandi's friends told her she was lucky to have a Doctor for a Father and Brandi knew it was true.
Her Daddy had a library of books loaded with pictures of female and male private parts that made her feel all tingly down below between her legs. Whenever she visited his office Brandi snuck one of the books from the top shelf and used her finger to pleasure her pussy in secret. It just didn't seem fair that she was not allowed to have a boyfriend yet. Brandi had turned 17 on her last birthday and would be going to State University in the fall. The sensitive young girl was certain she would be the only virgin in the freshman class.
The 17 year old Brandi had two younger siblings were both 16. Only 18 months younger than her. The twins were always making trouble. It seemed like whenever Brandi got in trouble it was usually started by either one or both of the twins. Still, she was expected to be the responsible one and look out for Jack and Jill at all times.
Jack was a handsome young boy.
He was quite big for his age and played outside linebacker on the football team.
Brandi was very mad at him because he had tormented both her and his twin sister, Jill, incessantly bragging about his new "non-virgin" status.
He delighted in giving the details of his nailing that stupid cheerleader slut, Cindi Johnson, after the game on Friday night. She had to admit the details were sordid but did serve to make her panties wet each time he described what he did to the 17 year old head cheerleader. Brandi had seen Cindi naked many times in the locker room and she was well aware of the dirty blonde's luscious tits and ass. One time she had peeked into the gym office and saw the same little slut Cindi bending over the desk with the coach's huge cock sliding in and out of her pussy from behind. Brandi was ashamed to remember how she had frigged her own slit watching through the blinds. She remembered in great detail how the seriously overweight coach punished Cindi's heart-shaped teenage ass and even used his pudgy fingers to spank her as he drove his throbbing cock deep inside her no longer virgin pussy. Her own satisfactory orgasm was achieved just as the coach pulled his dripping shaft from the whimpering girl's bottom. She was mortified at her own depravity in imagining the coach's cock filling her pussy with the sticky fluid he had covered all over the uncomplaining Cindi's lush bottom.
Jill had cried the last time Jack had regaled them with his sexual exploits. Brandi did her best to console the young girl, but Jill told her it was not the crudity of her twin brother's words; it was the fact that the silly slut Cindi had taken Jack's cherry. Jill whispered in her ear that she had long envisioned Jack and her losing their cherries together sometime this summer.
Brandi was not shocked.
In fact, she had longed to stroke Jack's beautiful cock on more than one occasion. She wondered if poor Jack realized he had two sure things sleeping in the next room each and every night. She told Jill that Jack would quickly tire of Cindi as he would find out she was such a "sleep with any one" slut bitch.
Brandi's Mom was a massage therapist and worked at the Serenity Spa on the other side of town.
Sometimes, her Mom would give her a "deep tissue massage" that caused her female juices to spill out of her virgin pussy lips. Her Mom knew exactly where to touch her to make her tremble with sexual excitement and she would always give a "Happy Ending" to each and every massage. They never discussed it and Brandi figured her Mom enjoyed it as much as she did. Brandi wished that someday she would learn how to do a good massage and she could make her Mother feel real good.
Brandi got stuck doing babysitting duty on her younger siblings shortly after the revelation that Jack was no longer a virgin. Now that he was a "man" he treated both of his untested sisters with a degree of derision that infuriated both Brandi and Jill.
Feeling a bit bored that night, she decided to give a massage to Jill just like the ones her Mom gave to her.
For some strange reason, Mom had never given a massage to either Jack or Jill. Brandi figured it was because they were so active and sports minded, they didn't need any special care like that.
Jill lay out on the massage table face down with her head in the little hole to reduce any strain on her neck muscles.
Brandi spread the baby oil all over Jill's nicely tanned back and began to massage her young sister's back and shoulder muscles. Jill groaned in pleasure at the touch of Brandi's firm hands rubbing deep into her skin. Soon, Brandi had worked her way down Jill's back to the base of her spine.
"Jill, I got to get these panties off so they don't get all oily, OK?"
Jill was breathing somewhat rapidly and grunted her assent. She lifted her hips off the table so Brandi could remove her panties. When Brandi slid them down her legs, she noticed they were dripping wet in the front. She brought them up to her nostrils and inhaled the scent of aroused femininity and sticky pussy juices. Her little sister was not so little after all.
Jack and Jill by Vickie Tern ([email protected]) Authors foreword "Jack and Jill" is a novel in ten chapters averaging 30k each about a fictional cross-dresser like you or me in fact or fantasy or remote curiosity, or else why have you read this far, and how he or she became the person who is narrating the story. It's mostly TG and femdom, with forced or tricked or cajoled feminization, but of course also m/f and m/m and f/f in various u.c. and l.c. combinations, and also...
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"What are you doing?" she pondered, getting up."Getting ready to take a shower," I answered, grabbing my robe. "Why, do you want to join me, step sis?"She strolled to me and slowly brought her hands to her back. "I'm a beyond filthy woman, so I should probably clean up," she answered, undoing her bra.She pushed down her panties as well and stood in front of me."What, do you think I haven't seen you naked before, Lacy? Just in the past few months, I've seen every single square inch of you,...
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Over the next few weeks, I could hardly think of anything but the idea of wearing girly clothes and how sexy it would feel. Every house I babysat at now, I would not just go through the underwear, I would dress up in it. I began to build up quite a collection of soiled panties stolen from the women of the neighbourhood. Some I would wash and return, others I kept as souvenirs. It began to grow beyond just panties, babydolls, bras and basques. I began completely to dress in a feminine fashion...
Over the next few weeks, I could hardly think of anything but the idea of wearing girly clothes and how sexy it would feel. Every house I babysat at now, I would not just go through the underwear, I would dress up in it. I began to build up quite a collection of soiled panties stolen from the women of the neighbourhood. Some I would wash and return, others I kept as souvenirs.It began to grow beyond just panties, babydolls, bras and basques. I began completely to dress in a feminine fashion...
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I had nothing to do, so I went out for a walk. I was walking for about ten minutes when a woman came walking toward me. Our eyes met and locked. She had such eyes that spoke to me on a new level. It took me a moment to regain myself. My scope of vision panned out and I took the rest of her in. She was medium height. Her hair was brown and her face soft. The rest of her looked like a model. Her breasts appeared to be firm and were barely contained in her T-shirt as well. She was wearing a pair...
Chapter 1: Phone Call I was at home, playing online chess when my phone started to ring. It was Jill. I felt blood rushing to my face. My heart was already galloping. I hadn't seen her more than three months. Back then she told me that we should stop dating and should just be friends. It was very hard for me, but there was nothing I could do. "I need your help, George," she said. Her voice was strange. As if she had problems breathing. And somehow tremulous. That frightened me. "Jill,...
Introduction: Our babysitter seeks answers about sex One of the things my wife and I loved about our house, the first time we saw it, was the neighborhood. There were kids playing outside, and everyone seemed to know each other. Since the house was also best of all we had looked at, we bought it immediately. While the house does have its issues, it has a lot going for it, too. First, it sits on a huge lot. Its actually nearly two full lots, meaning we have a huge backyard. It also has a great...
"Andrea, Susan, can you two come down here for a minute?"I heard mum calling us and felt my cheeks flush angrily. I know Susan was still young but I wasn't a child anymore and didn't want to be treated like one."Andrea, don't start young lady, my taxi's here." The neutral tone couldn't hide her impatience and I could picture her looking at her watch whilst standing at the door, waiting for me to show myself. Knowing she wouldn't leave until I'd done as asked, I resignedly sauntered to the top...
Voyeur