Sissy Stepson 10 Stepmother s Sissy
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I was a typical 41 year old guy, unmarried, reasonably well off, with the
sexual drive that goes with being in pretty good health. I had met an older man,
a widower of 65, through an acquaintance. He had come over to my house to check
out some furniture I was getting rid of. Unfortunately, he stopped by about an
hour earlier than we had planned - while I was right in the middle of a session
of internet porn and jacking off. To make matters worse, I was at the computer
near the front of the house, so I suspected that he had heard the sounds of sex
from inside when he came to the front door.
I hurriedly pulled my pants on and closed the window on the computer. After
composing myself and getting a shirt on, I answered the door.
He was an average looking guy with grey hair, and about 15 extra pounds around the midsection. We chatted, and looked over the furniture. When I asked him how much he thought it was worth, he suggested we check some things out on the internet for comparison. I didn't see a problem, until, that is, he accidentally clicked on the history menu. Busted! There were all the sites I had been on.
"I like the first two myself, but that last one doesn't do anything for me", he smirked. I stammered a little at first, but then reluctantly agreed with his judgment. The last one was one of those cheesy commercial sites with lame actors and no "soul". The first two were amateur swap sites.
"Mind if I check one out?", he asked. "I haven't been on for this kinda stuff in a couple weeks."
"Sure - knock yourself out".
Well, it was probably to be expected at that point that we would end up both lying in the bean bag chairs, watching blowjob videos and jacking off. I wasn't a complete newbie to this, but it had been very infrequent. The sight of eachother's growing penises turned us each on, and I for one was stroking pretty furiously.
We took turns choosing the video, but I noticed that he liked deepthroat videos as much as I did, along with videos of some nice wife on her knees in front of her standing man, long hardon nicely sliding in and out of her soft wet mouth, until, of course, he pulled his tool out and covered her adoring, smiling face with copious amounts of seed.
"It's been years since someone has done that for me," he almost gasped as his breathing got heavy. "How 'bout you?"
"Even longer, but I was never as much into getting oral with my wife as in giving it."
"A giver, huh...boy I would love it if...." his voice trailed off, not wanting
to cross any lines or ruin the great time we were having.
I thought about what he meant. I had sucked dick once before, but had basically enjoyed it. And besides, his penis was a nice, average, clean one with a squishy mushroom head and a big, round tight sack tucked below it. I had been watching him pleasure himself for almost 20 minutes now, and I was as horny as could be.
"Would you like me to break your dry spell?" I asked, almost amazed to hear my own voice saying it.
"Would you really? I can't TELL you how bad I want it!" He stood up.
"OK" - In an instant, I was the "loving wife", on my knees in front of him, caressing his tool. It looked so much bigger from this distance, and it smelled wonderful. Once I popped it in my mouth, there was no turning back. I lost myself in the pleasure of making this nice older gentlemen feel the ultimate pleasure. Soon, I was moaning, slurping, pumping, caressing and licking. His lovely penis was so hard in my mouth, and the head felt so good as it filled up the back of my throat. I would hold it back there and reach my tongue out to lick his scrotum and the base of his cock. Then I would draw my lips tightly against the shaft and slowly pull it out, then just as slowly slide it back in.
"Start just bobbing on it, a little faster, I'm getting really close. Watch out, I think this is going to be a realy big load." I did as I was told.
"Rub under my balls and take the cock all the way in..."
"Now just suck really hard ... oh,...there it is...keep it in your mouth...I really want you take my sperm...oh, oh.." and then I felt his hand gently on the back of my head, easing my mouth even deeper. I have never been so sexually thrilled in my life - I could feel his heart beating in the throbbing of his cock head against the back of my throat, and then the warmth and salty taste as his sperm rushed all around my mouth, tongue and out over my lips and chin.
With his softening tool still gently resting in my lips, I look up to see an
expression of such appreciation and joy. I understood then why so many women
love giving head...
We had almost weekly sessions after that, until I had to move away.
Chapter Five: I realize I needed to understand Robert's motivation and desires betterIt happens again the next morning.I arose early, slipped out of bed without waking Robert. Silently, I went into the bathroom. I turned the water on, giving the hot water time to work its way through the pipes for my warm shower. While waiting for the water to warm up, I stared into the mirror and assessed my thirty nine year old body. Objectively speaking, I was in excellent shape. My breasts were firm and...
TabooThe vulnerability of my stepmother aroused me first, a primitive biological urge harkening back to the plains of the Great Rift Valley when our ancestors slept in trees and sowed their seed whenever and with whomever they could in the survival of the fittest or, in my case, the most voyeuristically surreptitious. Add the sibling rivalry of a brother with his stepsister and color it with the twisted desire of i****t, one of the biggest taboos of our culture, a taboo so tempting that it is...
On her fourteenth birthday, she went out with friends to a karaoke bar and had a lot of fun with friends, but when she came home her mother said that she had to talk to her. “Jenny, you know how much I’ve said that you have to date a white man when you grow up right?” “Yeah...” “I talked to your stepdad and I think it’s important for you to learn how to be with a white man.” “Okay.” “When you wake up tomorrow, I want you to talk to your stepdad about learning how to be a woman.” Jenny...
July, 1983, Chicago, Illinois On Sunday morning, the phone rang at 6:00am. Stephanie was calling to say that she was leaving home and that she and Trish would be at my place in about six hours. After I ran and ate breakfast, I called Karin, despite having just seen her a few days before. After our call, I double-checked that I had all the food I needed and checked that the guest bedroom where Trish would sleep had clean sheets on the bed and that there were clean towels in the downstairs...
Sissy Stepson Part 1 ? Stepmother's Trap Carl Monet was a shy boy of about 15 when his widowed father married Rita Parker. Mrs. Parker was 20 years younger than Carl's father Larry. Carl was very shy and sheepish toward his new stepmother and the new Mrs. Monet was rather cold and distant towards him. Carl's father was gone quit often on trips abroad for weeks at a time and Mrs. Monet was often gone shopping with her sister Maryann and her mother Regina. Carl was...
Stephen and Stephanie Now the idea of crossdressing had appealed to Steve for a few years, he wouldn't deny it, but actually doing it for real, no he hadn't got the nerve. A surreptitious wearing of bra and panties, yes once or twice, but for nothing more than a different masturbation thrill. The full works, no he wouldn't know where to start. It wasn't even like he was gay or even bi, it was just a thing that fascinated him. He'd thought about asking one of his Mistress...
On a scorching hot day in July, the courtroom resounded with the final blow of the gavel. I sat there, relief overtook me as the realization of what just happened began sinking in. My now ex-wife stormed out with her lawyer, the judge had ruled in my favor and she walked out with nothing.Elsa, my now ex-wife cheated on me with another woman, and tried to ruin my reputation along with my business by concocting an elaborate scheme. Here claims were unfounded, she accused me of being an adulterer...
Taboo“Jenny, I want to show you why you suck off a man. Men can give you great pleasure too if you help them out first.” He said. The asian stepdaughter submissively nodded with tears in her eyes while saying nothing. “I want you to take off all of your clothes.” Her stepdad ordered. Jenny began to remove her shirt and reveal her small but round teen tits. Her baby fat perfectly framed her face and showed her more childish side. She pulled down her jeans and revealed her slight hourglass hips....
Becky creeped around the bushes of her house, trying to be stay quiet and out of sight of any nosy neighbors. Her parents were likely already asleep, but it never hurt to be careful. Her friend, Harper, had had a big party at her house, and Becky had snuck out to go to it. Not only would her parents not approve of her going to a party that started at 10:00 pm and ended at two in the morning, but she had also been grounded for getting caught smoking weed by her mother.It was a big risk, but she...
ReluctancePregnant?! that would explain the nausea, at least. How dare Stephanie do this to him! Now they were pregnant (and how was that thing to come out?) and some guys' names were tattooed on the body they shared. AND they were on the way to fuck him. Oh, yeah, and he now had breasts! Not to mention that his soon-to-be lovers had sole possession of his bank account. What to do??? He wanted to get out of this fuck-up, and quick. Suicide was the first thought, but he knew this idea...
Stephen prepared for his change. Every solstice it was the same: get ready for his six month sleep. He didn't remember when this all started, but the centuries seemed to blur after awhile. All he knew about her on the other side was kept in the journals they wrote back and forth to each other. Once a year he would go to sleep after leaving her a written message, then he would wake up six months later with no memory of half a year. She would leave him a message, too, usually...
As neighbors, Carol, Karen and I regularly met up on weekends during school term and more often during the holidays. We played many games together, and I happily joined in, despite their girly nature; I even played with dolls. Of course, the kids at school found out about this, and I was bullied mercilessly for being a sissy. I tried to explain that no boys were living nearby to play with, but in truth, I didn’t relate to macho boys while I was happy and comfortable with Carol and Karen. Our...
CrossdressingPart 4 - Stepmother's Test She crossed her legs and began dangling her high heel again and Carl became excited. His sissy stick started to stick up as he watch the dangling show and fashion models prancing on the run way. He had no where to escape and his stepmother noticed her panties bulging with his sissy cock. She nonchalantly let the shoe fall on the carpet and said, "Well, missy are you going to pick my shoe up and place back on my toes or can't you get up!" "Yes, ma'am, I...
October, 1983, Chicago, Illinois On Sunday morning, I let Jackie know I was going out for my run. We kissed and she headed for her room so that she could shower and I headed outside. When I got back I showered and made my usual call to Karin, then went downstairs to make myself some breakfast. Our Sunday afternoon discussion was fairly tame, as nobody seemed up for any controversial talks. Jorge, Charlie, and George were there, though Jamie was absent as Jackie had predicted. We discussed...
Shaking a little, Stephanie waited on the doorstep of David's home, a detached four bedroomed house in quite a good neighbourhood. Barbara gave her a lift so she didn't have to get a taxi or trundle her case along the road. "Good luck Steph," she called back when they parted, "Go with the flow. He's not a bad man really. You've seen him at his worst for the last few days." Compared to her own one bedroomed flat, this was a palace but in fact in was just a good middleclass dwelling....
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Dear Stepdaddy, I'm in eighth grade and now I got a problem. It was all fine until last summer when Mom married Roy, my new stepdad. No, it ain't what you think, Roy's not fucking me. Though I know my age's not bothering him, since he is screwing my friend Tabby. He doesn't know I know, but her and I tell each other everything. The problem with Roy is that he makes me get good grades. Mom never cared much, but Bob says if I don't get good grades, he's gonna make me go to summer school...
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Pluto was rudely awakened by a loud dinner triangle, ringing as Persephone walked down the stairs. “Time to eat up slave!” as she walked down the spiral staircase. Pluto had been locked into the large cage he had seen the night before. He was still completely naked, save for the chastity cage which very uncomfortably suffocated his penis. He looked up and his jaw nearly dropped. He had seen Persephone last night, but that was in a confusing, hazy daze. Now he had his full senses about him and...
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Persephone finally had Pluto where she wanted him. It had been a tiring chase, but she knew the prize was worth it. With most men being hunted nearly to extinction, she was determined not to let this one get away. Now he was tied down on her milking table, in the depths of her dungeon. And she was going to extract every drop of semen from him however she could.With technological advances and women's growing superior intellect, most women decided that the world did not need men and all of their...
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Disclaimer: None of these characters belong to me. Harry Potter and all the associated characters named in the story are the property of J. K. Rowling and her publishers and have been used without permission. As fan fiction, no money has been charged, or may be charged, for publication of this work. Hermione Granger had snuck out of the castle that was Hogwarts School of Witchcraft and Wizardry because Hagrid, the half-giant game keeper, had finally agreed to show her what she had wanted...
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"Damn, Milos was right; these baked onion rings are great. Hell if I'll let him know that, though." Ben took another pull on his craft beer. As crazy as Milos was, this gay sports bar was making them both a lot of money, perhaps as much because of the irony.The waiter, with fashionable facial hair, dressed in a football jersey with a cheerleader's skirt came up, asking if he would like another beer."Sure, but make it a good German beer this time. Can I ask about the outfit? Why the...
In this chapter, Syren De Mer is my stepmom Brandi's best friend from high school that Brandi invites over to catch up over a glass of wine. Chapter 2: My Stepmom's Best Friend I woke up to find that I was still snuggled up with my stepmom, Brandi on the living room couch. We we're still naked. I woke up thinking what happened yesterday was all a dream until I woke up naked laying next to my beautiful stepmom, Brandi. I started to gently play with one of her huge boobs as I sucked on...
My Mom married James when I was 12. My father had died two years earlier. He only had a small life insurance policy and our family had been struggling to get by. We moved in with James the day after the wedding. They never went on a honeymoon. I had previously met my new stepbrothers a couple of times, including at the wedding. But the following weekend was the first time that I spent any significant amount of time with them. All four were older than me, anywhere from 6 months to 5 years...
Having enslaved Stephanie, Blair and Joanna still had to deal with the fact that she was probably pregnant with Blair's child, and the fact would soon get out to his staff. True, he was the boss, but would his employees ever respect him after this episode of incest? The couple agreed that Stephanie would stay at home to babysit Oscar during the day, and that she would do all of the household chores as well. Only then would she be rewarded with sex and other privileges. She would also have to...
Group SexChapter 1 Stephen sighed as he watched the world go by. "I still don't see why we have to move," he told his wife as he turned to look at her. "Because honey, the company is opening a new store in Stepford and they asked me to run it," Emily replied, not taking her eyes off the road. "Besides, the offer was too good to turn down and the house came as part of the job," Emily continued. "I'd thought that you'd be proud of me," she added. "And I am. Really," Stephen added as his wife...
Wishbone LITE By TwoSpiritsTG ----------------------------------------------------------------------- This was a short story I entered into a TG fiction competition a few years back with a 1000 word maximum (This story is 1010 words). For the record, I did win first place. I originally wasn't going to upload it here because of how short it is, but decided otherwise and here we are. If there is demand to expand it to something more I'll gladly do...
"Mount up, babydoll!" he said. At last understanding, Christine squealed and leapt to her feet. She pulled up her skirt and wiggled her hungry red beaver at him. She needed a trim. With a wish, all her pubes fell out, then an arrow-shaped landing strip grew in their place. "Are you really going to fuck me Mr. Phillips?" she asked eagerly. "You bet your sweet ass I'm going to fuck you, Christine!' he exclaimed, reaching around to grab said ass. "It really is your only hope of...
February, 1983, Chicago, Illinois The drive back to Chicago was, as it usually was, uneventful. We arrived home just before 6:00pm and to my surprise, Stephie was making dinner. I gave Stephie a quick kiss and took my bag to my room then came back to the kitchen. Eduardo said goodbye and headed back to his dorm. I poured myself a glass of red wine and sat at the kitchen table while the girls finished making dinner. They got everything on the table then sat down so to eat. “How was the...
November, 1983, Chicago, Illinois The week before Thanksgiving break flew by. It was pretty much the usual - class, studying, karate, Penny’s computer lessons, my usual Thursday afternoon with Anala, and Elyse and Jackie alternating nights with me. By 6:00pm on Friday evening, only Katy, Stephie, and I were left at the house. Stephie offered to come with us to Midway so the three of us left just before 7:00pm. At Midway, we waited with Katy until she boarded her 8:30pm flight, then headed...