Rosie Kowalski's Introduction To Sex. ( A Toby Wakefield Story). free porn video

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The summer of 1954 presented me with the most preposterous sexual adventure that any teenager—any man of any age for that matter—could hope to experience. Sometimes I pinched myself to remind myself that I was awake

I’ve never told anyone about my involvement with Kathy and Rosie, not even my closest friends. They were two girls who were a slice of my “coming of age” which was a lot more than most boys going through puberty ever experienced. My involvement with Kathy and then Rosie could be claimed by many young boys who have gone through the mysteries of erections. But I have to believe that my involvement at the convent at St. Bartholomew’s Catholic Church was peculiarly unusual, particularly for a young boy who was not even a member of the Catholic faith. In retrospect though, it was because I wasn’t Catholic that made the experiences possible. (See Penguin’s Preference)

Because of Father McNamara, the priest at Saint Bartholomew’s before he was replaced by another priest who turned out to what happened with me while unusual might make sense to you. During Father McNamara’s tenure at St. Bart’s, he had a secret sexual involvement with all of the Holy Sisters except one. When the gay priest arrived the Mother Superior and those of her flock who enjoyed Father Mac’s sexual attentions were confronted by a serious gap in their sexual satisfaction. Enter the fourteen-year-old Toby Wakefield.

Because the Mother Superior of the convent found me both desirable and trustworthy, I was introduced to some of the most unusual circumstances that a young man could find himself in. I would never have betrayed any of those confidences while that particular priest or any of those sisters were still alive, but they are all gone now. Mary Cecile, the youngest of the nuns with whom I was actually in love passed away just two years ago. She died of complications of uttering cancer. She was just five years older than me.

Having related much of what happened at St. Bart’s in Penguin’s Preference this story gives a little more insight into what went on in the neighborhood, specifically with Kathy and her brother Ray and another neighborhood girl, Rosie Kowalski whose family moved into the neighborhood in 1954. In that story, I related my friendship with Ray and our involvement with his younger sister Kathy. Here I tell of how the girl across the road from me became part of our special little group.

When the Kowalskis broke ground to build their new house across the road from ours it was an exciting event for us. Nothing new had happened there for a couple of decades. When the bulldozer, crane, and dump truck came to excavate the Kowalski’s property and started breaking ground for the house it was a new beginning for the entire neighborhood. From time to time we would see the Kowalski’s visiting the construction site. I couldn’t help noticing that they had a cute daughter. Just before the house was finished, I noticed the girl, Rosemary, playing with Ray’s sister Kathy. They had become friendly during the construction process.

When the Kowalskis moved in my mother and father insisted that we go over as a family and welcome them to the neighborhood. I was about halfway through my fifteenth year. Up close I could see that Rosemary, “Rosie” as her dad called her, was as cute as a button. She was a willowy girl with newly developing breasts. It was easy to tell that she was flirting with me, though shyly. Knowing no bounds my fantasy libido demanded that I add her to the stable of females that put me to sleep each night while masturbating. I’d already become involved with one of the nuns at St. Bart’s (the Mother Superior) but even so, Rosie often ruled my thoughts after the lights went out.

The fact that Kathy and Rosie were playmates made me wonder if Kathy might be sharing some of the experiences, she was having with her brother Ray and me. Kathy and Rosie were new friends. Rosie was Catholic as well, a new addition to St. Bartholomew’s. I don’t know why that should mean anything, other than the fact that I was Protestant. My sex partners consisted of four adult Catholic nuns and Kathy, a Catholic girl.

~Girl Talk~

“Good morning, Rosie,” Mrs. Warren said as she opened the door that Saturday morning. She was surprised that Kathy’s new friend was at the door so early. “You are early sweetie, but it won’t hurt Kathy to get up, I have lots of things for her to do today. Why don’t you go on up to her room and introduce her to the day?”

Shaking Kathy, Rosie was too energized to be gentle. “Wake up Kathy I have to talk with you.”

Lifting her head with sleepy eyes Kathy smiled as she said in torpid surprise “ROSIE,” and asked, “What time is it?”

“It’s about a quarter to eight Kathy. But I have to talk with you.” Just then the noise of a door opening and closing came through the wall. There was the sound of a dresser drawer being opened and a quick slam as the drawer was closed.

Kathy put her finger to her lips. “Shh, Mom’s in her room.”

Wide-eyed, Rosie said in a surprised murmur, “Your parents’ room is right next to yours too?” Kathy nodded. “So is my parents’ room, it’s like the walls in our new house are paper thin. I can hear everything they do.”

Pushing herself up on her elbows Kathy smirked and said, “You should hear them (directing her head to the wall).”

“That’s what I’m talking about,” Rosie said, blushing deeply red, “That.”

Putting her hush finger to her lips again for Rosie to keep her voice down Kathy whispered, “You don’t need to be embarrassed Rosie, I know what you’re talking about, he-he-he.” As Kathy stifled a serious giggling stream Rosemary laughed a little too loud too. “Shh,” She stifled her laughter again, “and you should hear some of the words they use.”

“Mine used the F ... word a lot,” Rosie said as she shrugged and looked around like someone might be listening

“Cock and pussy too,” Kathy said. Rosie looked at Kathy out of the corner of her eye. She wasn’t sure she could completely trust her yet. Trying to figure out what was on her new friend’s mind she said, “What is it, Rosie?

Rosie cleared her throat. “Um ... I-I have an idea what ‘suck my cock’ means but don’t even have a clue what, ‘eat my pussy’ could mean?”

Kathy giggled as she said, “You talk like a virgin Rosie.”

“What do you mean by that Kathy? Of course, I’m a virgin.”

“I’m just teasing you, Rosie. I’ve never met a girl our age who isn’t a virgin.

“I would just like to talk to one who isn’t so she could tell me more about what sex is like,” Rosie said. Abruptly changing the conversation to what they were talking about before she segued to, “My parents say things like, ‘suck my cock, he-he-he or fuck my cunt.’”

“And ‘eat my pussy,’” Kathy reminded her. She broke into an uncontrollable, nervous giggle that she had to suppress from turning into laughter.

Kathy’s mother’s door opened and then closed. They could hear her footsteps down the hall and then going down the stairs. The uncontrolled laughter became louder. Then as fast as it had started it seemed like all the levity had been sucked out of the room. Kathy said. “I had always heard Mom and Dad carrying on in their room at night, but it never meant anything to me. But when Ray talked me into playing “doctor” with him last year I saw how much different we were. When I touched his um thing it got hard—he called it a ‘boner’—and it all began opening up to me.”

Other than her aunt’s baby Rosie had never seen a naked boy. Amazed she asked, “You saw your brother NAKED?”

Kathy said, “I’ve seen both of my brothers naked before, but we were really small at the time. Three years ago, Ray told me that one of his friends told him about playing doctor with his sister. We kind of ... um ... explored each other. He touched my thing and let me put my hand around his.”

“You actually touched and HELD it?”

Kathy smirked and nodded her head.

“What did it FEEL like?”

Concentrating she said, “It wasn’t hard like you might think hard would be. It was stiff but warm and firm. He-he-he I could feel his heart beating in it. And –her eyes were filled with amazement—the skin on the outside is like a loose sheath. You can hold his penis in your hand and move the outer skin up and down like it was some kind of loose casing. Everything about is amazing Rosie.”

“Do you ever wish that you could do the things with your brother that you hear your parents doing Kathy?”

It was just like when she was in bed the night before when she was listening to her parents through the wall. She was getting wet between her legs while talking with Kathy like she had then. Her panties felt like they were getting damp.

Because Kathy told her about playing doctor with her brother Rosie took for granted that Kathy had already touched herself between her legs. She needed to confess something to her friend and decided to be bold. “Yesterday when you picked up that nasty rubber thing that was lying beside the road Kathy, I thought I might get sick. When I went home, I thought about the way we talked about what those kids were doing in their cars, where we so those rubber things and you picked that one up?”

Kathy smiled and nodded. She didn’t let on that she had already gone all the way with her brother Ray and Toby Wakefield. She wanted a friend her age to confide in but had to be sure that Rosie could handle it if she decided to take her into her confidence and let her know what was going on.

Rosie continued, “Then last night when I heard my parents um, doing it’ on the other side of the wall I got all ... um ... wet between my legs thinking about what we talked about yesterday and listening to how they said those nasty things in that silly way. It was dirty talk Kathy, but it made me feel funny. I-I started touching myself.” She had to find out if Kathy had one of those too and asked, “Do you have a bump at the top of the crevice in your vagina that makes you feel tingly if you touch it, Kathy?” Noticing how intensely her friend was looking at her she saw Kathy’s hand go beneath her covers and she started wiggling.

“I do Rosie and it does more than just tingle when I touch it.” She grunted as she wiggled.

“I was afraid you would tell me that you didn’t have one ... that I was just some kind of freak.”

“I DO have one Rosie and it’s more than just a bump. And it makes me feel wonderful when I rub it.” She wanted to tell her, “You should feel it when somebody else touches it.

Rosie thought about Kathy telling her about playing doctor with Ray. She was sinfully envious. “Kathy? I have a confession.” She watched her friend’s eyes widen in question. “I’ve been thinking about Ray and you. I-I’ve been wondering if you and he ever do anything.” She dropped her eyes in embarrassment then looked back up and said, “I’m jealous that I don’t have a brother to play doctor with.”

Delighted that Rosie had just said that she began to see the possibility of what she had wished she could include her new friend in. “Um ... Rosie ... I’ve been thinking ... um ... would you ... um ... do you think that you ... um ... could play doctor with ... um... me?”

What Kathy had said to her was so shocking and unexpected that she heard static in her ears. But she had always wanted to see another girl naked. Kathy was her friend who she often imagined as completely unclothed. “Oh Kathy, do you think we COULD? I-I don’t even know how to begin.”

Kathy was dressed in a short kind of nightie. Still, under the covers, her fingers were playing with the sexual pudding of her pussy. Clearing her thoughts she said, “I can show you what to do Rosie.” Her hopes soared when she saw the interest in her friend’s eyes. “I’m wearing a short nightie and no panties. I can ... um ... sit at the head of the bed, spread my legs, and show you mine.” Waiting to make sure that Rosie was in she went on, “You can take your panties off, sit at the foot of the bed and show me yours. What do you think?”

What her friend suggested was more than OK with her. Sitting down on the bed she quickly removed her tennis shoes, undid her pants, and took them off. She hesitated for a moment, shrugged her shoulders, and then, though blushing and unsure of herself, peeled down her panties. Lately, she had been so eager to be naked with somebody else that it didn’t matter whether the “somebody” was male or female.

Throwing back the covers on the bed Kathy rolled over, sat with her back to the headboard, and hiked up her nightie. Sitting cross-legged at the head of the bed she ogled Rosie who was cautiously opening her legs. She giggled when Rosie’s wide eyes met hers.

“Wow,” Rosie said in a quavering voice, “I’ve never really been able to take a good look at my ... vagina. Yours is fascinating. It’s strange but pretty ... kinda like a flower.”

Having never been naked with another girl either Kathy was thrilled to be in this “I’ll show you mine if you show me yours” game with Rosie. “When I played doctor with Ray,” Kathy said, “We examined each other. Would you like to examine me?”

Betraying her fascination with her excited voice Rosie said “Really?”

Stripping her nighty Kathy confirmed, “Mm-hmm.”

Rosie was so glad that Kathy appeared so casual at what she was doing. It made her feel natural and did process guilt. Taking the cue, she stripped her t-shirt top and completely exposed herself.

The girls studied each other’s bodies: Rosie’s nymph-like puffies had only started to develop. Her legs were already showing signs of becoming sculptured beauties, she had an outie navel, and her mound was completely bare. Kathy noticed that her outer vaginal lips were much thicker and puffier than her own.

Kathy’s breasts still had room to grow but they were already being nicely formed between A and B cups. Her mahogany-colored Spanish peanut-like nipples were encircled by one-inch areolas of the same color. She had an innie navel and nicely shaped legs. Her pubic area was fleshier than Rosie’s and more pronounced with a small number of hairs growing out and beginning to curl. Her vaginal lips were fleshier than Rosie’s.

Because her legs were spread wide her lips were partially opened, showing the pinkness that was framed by her outer lips. At the top of her vee was the distinct presence of a clitoris that was bulging just where her lips parted. “Well?” Kathy said, inviting Rosie to inspect her.

“Oh,” Rosie said, coming out of her awe-filled stupor. Sitting on her butt she edged closer, laid back, and propped herself up on her elbows. Kathy stretched out on her tummy and propped up on her elbows and said, “This is so exciting.” She edged closer reached out and touched her friend’s labia. “I’ve touched mine,” she confided, feeling strange in telling another person.

“But touching another person’s is ... is ... it’s CRAZY.” She said, looking into Kathy’s eyes. “It’s wonderful Kathy but ... isn’t it wrong?

“Does it feel wrong Rosie? Besides, what harm can we be doing?”

She felt all around Kathy’s mound and put her pinkie in her innie navel. “Mine doesn’t go in like this.” She tested the puffiness of Kathy’s mound. “Mine’s not as spongy as yours. And he-he, I don’t have any hair.”

“That’ll come and your breasts will get bigger too,” Kathy said as if hers were large. But in comparison...

With a hopeful look, she said, “Can I open your lips?”

“He-he-he Rosie, sure you can,” Kathy replied.

“This is so exciting he-he-he.” Pressing on Kathy’s labia she opened them. “Omigosh, it’s so PINK he-he-he. I’m SO excited.”

“So, am I Rosie, it’s so naughty but so much fun, isn’t it?”

Taking in all of what she was seeing: the pink wetness, the hole that opened when she spread Kathy’s lips wider, how there didn’t seem to be a rounded definition to the hole itself which opened in a jagged kind of manner, and the juices that seemed to be bubbling inside she wondered, “How can I see your h-hymen Kathy?”

“You can’t Rosie; I tore mine with my fingers. I’ve never seen it myself, but I bled when I tore it.”

“Did it hurt?”

“It felt like something snapped. It hurt badly for a minute ... then I bled some for another minute or so.”

Rosie was too embarrassed to tell her but since she was already looking at the inside of her friend’s vagina, she had to tell her what she discovered about herself. “I touched mine last night, I think. I tried to put my finger inside my hole but only got it in a little way. My finger ran into something that wouldn’t let me inside. I pushed on it, and it was springy. But I was afraid I would hurt myself. I guess it’s my um ‘maidenhead.’”

Eagerly Kathy leaned forward, swung her legs to the floor, and sat up. “I want to see it. Sit up Rosie and spread your legs, ok?”

“Darn it,” Rosie said as she sat up while Kathy pushed her legs further open “Is there any way I can see yours too?”

Ignoring her friend’s questions, she said “Put your heels on the edge of the mattress Rosie and spread your legs further open.” Excited about what they were doing Rosie quickly did what Kathy said. Kathy pushed on Rosie’s labia, opened her lips, and spread her vulva wide. Looking inside she said, “My GOODNESS ROSIE your hymen is ... is like a PLUG inside you but it has a tiny hole in the middle of it.” She put her finger inside and tested the tautness of it.”

“Be CAREFUL Kathy, don’t HURT me. Darn, darn, DARN I wish I could see it.”

“It’s so cool Rosie.” She thought for a second. “I think I can help you see it, though.” Standing up she went to her dresser, bringing back a hand mirror. “Spread yourself open Rosie,” she said as she squatted down, holding the mirror at an angle so her friend could see it as well.”

“Move it up a little Kathy,” Rosie said, “There. Oh WOW, that’s so COOL. It does have a hole in it. It’s like a little donut he-he-he.” She eased a finger inside herself, testing it. “I can feel the little hole now Kathy,” She pushed a little harder. “It’s going ... IN.” Easing her finger to the second knuckle she smiled. “It doesn’t hurt at all. It feels good. And it feels um ... spongy.”

Having stared at Rosie’s vulva for so long and watching her push her finger inside her made Kathy excited and wet. Her finger was now on her clitoris moving it in a firm, circular motion. “Um Rosie?” she said, breathing heavily through her nostrils, we were talking about those crazy things our parents were saying when they were ... um ... um... doing it?”

Rosie wiggled as she moved her finger inside her vagina and worked her thumb on her clitoris. She raised her eyebrows. “Like ‘fuck me’ and ... and ‘eat my pussy?” Her breathing had accelerated. Kathy nodded, imagining how strange her father had talked about eating a cat ... But she knew it had to have another meaning. Giggling she said, “It sounds like the silliest thing.”

“I know what it means Rosie.” Her friend’s eyebrows raised, and she returned a look of profound interest. “Would you like me to show you?”

“To do what?”

Kathy’s answer was not a complete lie. She had been looking through the keyhole of her parents’ door when her mother had said it to her father, and he’d gotten on his knees and put his mouth right on her mother’s vagina. She said nothing to Rosie about her brother Ray doing it to hers—and then Toby. It felt heavenly.

Not sure she was ready to go that far yet Rosie was hesitant. “Well ... um ... maybe ... ok, if you think it’s alright.”

Taking her friend’s hand, she coaxed her finger out, leaned forward, and pressed on the lips of her pussy—opening it. She raked her fingertip upward in Rosie’s groove until it touched her clitoris then put her lips on Rosie’s large vaginal lips.

Her friend jerked and said, “GEEZ-O-MAN Kathy, what are DOING?”

Kathy looked up and with an impish grin said, “I’m eating your pussy, Rosie.”

“WOW, I was so SURPRISED. But it feels so GOOD.” She reached out, placed her hands on her friend’s head and, not wanting to be too forward, gently let her know that she wanted her to continue. Kathy began lapping in Rosie’s groove and she squirmed and sighed. “What if your mother comes in Kathy?”

She said, “We’ll hear her when she starts walking up the stairs.” Kissing the lips of Rosie’s pussy, she inserted her tongue between her labia. “By the time she makes it down the hall,” she slurped, “I’ll have my nightie back on and you’ll have time to put your panties, pants, and socks back on.” Her mouth covered Rosie’s pussy again and she started lapping.”

“Kathy?” Rosie said as she stiffened. Kathy grunted her acknowledgment. “Do I smell bad down there?” She grunted “un, uh” as she masturbated Rosie’s clit and then pushed her finger inside her pussy. Holding out the finger that had just been touching Rosie’s pussy she held it to her friend’s nose and said, “It’s hard to describe what it feels like,” Rosie said. “But it smells nice.”

Kathy told her that they both smelled the same. Then she told her to taste her finger. Tentatively Rosie touched the finger with her tongue and sucked it into her mouth. “It’s hard to describe what it tastes like too, but I like it, I think.” Resuming her lapping, her tongue finally got to Rosie’s clit and circled it.

For Rosie it was like a firecracker had exploded, her ears were ringing, and she was breathing heavily, shuddering and gasping. “You just came,” she heard her friend say through static-filled ears. She didn’t know where she had come from, but she knew that what had just happened in her body was the nicest feeling she had ever experienced.

Suddenly Kathy was on the bed beside her, sitting with her legs spread. “You do mine now.”

When Kathy had put her mouth between her legs Rosie’s first thought was how disgusting it was and that it had to be wrong. But when she began feeling the pleasure, she was getting from it she became an instant convert. As she pictured her father doing it to her mother, though the picture was strange, she understood the ecstatic way her mother had moaned and sighed, not to mention the dirty words she had used.

Eager to give Kathy the same kind of pleasure she had just been given Rosie got quickly on her knees and opened her friend’s pussy. “OMIGOSH Kathy,” she said, “Your bump is HUGE.” What she’d felt of hers and seen in the mirror that Kathy had held in front of her was a definite bulging prominence with a pink tip poking out of the suede-like sheath. But it was infantile compared to the long, fleshy appendage that filled the top of Kathy’s slot.

With her face soaking in Kathy’s wet vulva, its indescribable scent, and taste filling her senses. Rosie felt like she was sampling an elegant delicacy. Suckling, she lapped and skated the velvet top of her tongue in Kathy’s slick groove. Sucking the wafer-like inner labia between her lips she tried to probe into her friend’s tunnel, wallowing her tongue in the spongy wonder between her friend’s legs. Centering on Kathy’s clitoris she suckled and nibbled it, rubbing it in a circle with the tip of her tongue. When Kathy exploded, she felt a surge of sexual juice flow into her mouth which surged over her nose and sagged down her chin.

When Kathy and Rosie came into the kitchen Mrs. Warren said, “Well, you girls look like you really enjoyed yourself. I bet you silly things were just giggling your heads off.”

Rosie gave her friend’s mother a demure smile as she pictured Kathy’s father “eating” Mrs. Warren’s pussy. Before she had come to the Warren’s house that morning, she knew so little about sex. Now her horizons were definitely on the rise.

After “going down” on each other Rosie realized that Kathy knew so much more about sex than she did. She had no idea how much experience her friend had but she knew she was curious enough to not let convention get in her way. With an older brother like Ray Rosie was sure Kathy must have been exploring more with him than she had let on. They had played doctor, and Rosie was sure they must have done more. Has he eaten her pussy? If he were doing this with his sister would Ray want to do the same thing too?

Hanky-panky

Toby: That summer Mrs. Warren knew she had to tighten her grip on Kathy. Healthy, hormone-ridden boys were on the prowl. It was becoming increasingly difficult for Kathy to get off their property and make it to “the Glade” where Ray and I cavorted with her. One particular Saturday though, just a couple of weeks after the Kowalski’s moved in, Ray assured me that Kathy would be there. When I asked if his mother was going somewhere for the day, he told me that she wasn’t. But Kathy would be coming with Rosie Kowalski. “Since Rosie and Kathy have become friends,” he said, “my mother has loosened the restraints on my sister.” In a conspiratorial laugh he went on, “As long as she’s with Rosie Mom doesn’t seem to worry as much about Kathy getting into trouble hanging around with the boys.”

I thought Rosie was hot, but I was afraid she might throw a wet blanket over what Ray and Kathy, and I had been doing together. Ray told me that Kathy said that Rosie was “hot to trot” ... that she and Kathy had done the ‘girl on girl thing.’” Then he told me this story:

“I was cleaning the basement one day when my mom was gone. Kathy came down with Rosie. We started playing around, you know like tickling and wrestling and stuff? Unintentionally Rosie put her hand on my cock and apologized. I got the idea that she did it on purpose. Kathy told me that she had hinted to Rosie about some of the kinds of things the three of us have been doing together. She said that Rosie was interested in it.

Out of the blue, right in front of me, Kathy asked Rosie if she wanted to see my pecker. Rosie acted shy and embarrassed but hemmed and hawed and finally said she did. When I pulled it out, I almost laughed out loud when Rosie looked at me all squirrely like. Then Kathy, slapping at it all playfully with her finger, made me get a boner.

Rosie looked like she couldn’t believe how big it got. Kathy said to Rosie, “Watch this,” then bent down and put my cock in her mouth. She bobbed on me a few times then asked Rosie if she wanted to try it. (They had been talking about sucking boys’ cocks). It took her a while to work up the courage, but she finally did. And she did it for a long time and seemed to like doing it. She started jacking me as she bobbed faster ... like she wanted me to come. I shot in her mouth and couldn’t believe it was her first time ... she swallowed my jizz without even stopping. After we were sitting around joking about it Kathy told me that they had eaten each other’s pussies. Kathy then told Rosie that I had eaten her pussy and Rosie asked if I would do hers too.”

“Did you?” I asked

“Yeah, I did it in the basement that day on Mom’s pile of dirty laundry by the washing machine.”

I was excited yet jealous that Ray had already done it with the new girl I wanted to have sex with.

“Have you done anything else with her?”

“I could hardly believe it, Toby,” he said. “A few days later when Mom went over to have coffee with Mrs. Kowalski Rosie sneaked over. I fucked her in Kathy’s room, she sucked me, and I ate her again.”

It made me feel left out. I couldn’t get over how much Ray was blabbing to me about having sex with Rosie and Kathy. I was afraid he might tell other guys about it too. Having never told anybody about it myself I told Ray that he could get us all in trouble if he kept talking about it. I never heard any rumblings from other people, but you never know what’s being said behind your back, and what people will say if they know about it.

“Anyway,” Ray said, “Rosie’s not a wet blanket.” He snorted and frowned when he said, “Kathy pissed me off when she told Rosie that you were better at fucking than I was though. (I felt really good about that). But she told me that she just said that so Rosie might get interested in coming to the Glade with us and finding out for herself. But now I feel funny about it, thinking that you are better at fucking than I am.”

I figured I was better at it than Ray. How could a kid have a mentor like Sister Natalie—the Mother Superior at St. Bart’s—and have as much sex as I had with the other nuns and not be better than a kid that was only fucking his younger sister?

Kathy and the nuns should have been enough for me but since Ray and Kathy were setting me up with Rosie, I wanted to make it as nice as I could for Rosie.

With her mom’s new rules Kathy, the issue of getting the girls to the Glade was no longer a problem, at least for the time being. Her mother thought that we wouldn’t like being around them because the two girls were always being so silly. So, when Kathy had a safe passage to the woods where we would do whatever we wanted she was pretty excited about it. But it was obvious that Rosie was anxious.

When the girls got to the Glade that day Rosie was nervous. Just the same she was flirting with me in an almost childish kind of way. I could see that she was nervous about being with someone new, so I said to Ray, “Why don’t you and Kathy take over the Glade while Rosie and I go for a walk.”

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Thirty-two people signed their pictures in my Armstrong High School yearbook, the most repeated comment being “Keep your winning ways and you’ll always succeed.” Mary Lou Devlin wrote: “You mean so much to me. You have taught me so much! I hope you succeed in Baltimore. I wish you weren’t going so far away!!!” I never had enough time for a steady girl but had two stalkers, Mary Lou Devlin, and Becky Baldridge. Becky was a pest. But had it not been for my commitments at ST. Bart’s and to Rina...

4 years ago
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Rina Strelnicov a Toby Wakefield storyChapter 3

As I followed the classy-looking widow from her bedroom through the hallway Rina’s husband’s silk kimono was giving me a sensuous massage. It was the most elegant garment I had ever worn. As a post-pubescent male, I was no longer mystified at how often my erections buttonholed me throughout the day. Entranced by the voluptuous swaying of Rina’s hips I almost laughed aloud when I realized how my fickle member was once again swinging heavily like a pendulum between my legs. Just the thought of...

2 years ago
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Penguins Preference a Toby Wakefield storyChapter 10

I felt squeamish walking onto the St. Bart’s campus, hoping that I wouldn’t see Father Des or Father Frank before I talked with Sister Natalie. Her door was open, and she saw me walking toward it from her desk. “Come in Toby, close the door behind you.” Rising from her chair she approached me, reached out, and placed her right hand on my cheek. “I’m so sorry that you had to go through that. Neither Father Desmond nor Father Frank will ever bother you again.” I wondered what kind of power...

2 years ago
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Rina Strelnicov a Toby Wakefield storyChapter 11

Tonight, was the first time he was aware that Cissy had a child. My child? Taken by the sphere of the whole thing: his attachment to Cissy as a young nun, their sexual shenanigans in the bosom of the convent, Monsignor McGlaughlin taking her to Baltimore where she would have her baby. Had this been planned from the time Sister Natalie encouraged their sexual union to start? And did Rina influence him to attend Johns Hopkins in Baltimore so he and Cissy could reconnect? Regardless of being...

2 years ago
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Penguins Preference a Toby Wakefield storyChapter 2

Looking up at the clock I saw that I had little more than one minute to go. I had learned early at St. Bart’s that when I lingered and was late, I got a harsh scolding from Mother Superior who was obsessive about time. Walking slowly back to the wing with the cells I went to the last one and knocked on the closed door. “Come in Toby,” wafted through the door. Opening the door, I was shy and tentative. The room was tiny and dimly lit. Blinking to clear my eyes I opened them wider. Mother...

4 years ago
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Penguins Preference a Toby Wakefield storyChapter 5

The Cleveland Indians had a great year in 1953. In 1952 they took second place to the New York Yankees. In ‘53 they repeated as runner-up to the Yankees and Al Rosen became the second person in the league to win the MVP. From the opening game in April all of Cleveland was wild about the Indian’s winning record. On Saturday, May 16th the Tribe would honor the Catholic Diocese by making free tickets available to all the priests and nuns of the Diocese who would be able to attend. The “Diocese...

4 years ago
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Penguins Preference a Toby Wakefield storyChapter 6

When the kids on the school bus got off the bus just around the corner from St. Barts, I told the bus driver that I had to pick up something from the store on the corner—my house was only a mile away from St. Barts. I walked to the convent, knocked on the door of Mother Superior’s office, and was asked to come in. Mother Superior picked up the crumpled hanky, getting my semen on her fingers, and dropped it saying “Yuk.” I had jacked off in it in the boy’s restroom just before getting on the...

3 years ago
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Rina Strelnicov a Toby Wakefield storyChapter 12

Two weeks before the dinner at Haussner: On the observation deck of Cleveland Hopkins Airport, a small crowd gazed at the sky in anxious anticipation. The plane was fifteen minutes late. “THERE IT IS,” one of them cried in relief as a spot appeared on the horizon quickly taking on the silhouette of an airplane. The thundering drone of its four engines soon shook the air as the silver, triple-tailed Lockheed Constellation emblazoned with TWA red letters flashed by. Tires screeched wafting...

2 years ago
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Penguins Preference a Toby Wakefield storyChapter 9

Two and a half weeks after the Diocese Day baseball game the school year ended, and I was out for the summer. Resuming my regular hours at St. Bart’s there was a lot of garden repair and replacement that should have taken a couple of weeks. But all my work that summer there was being constantly interrupted. Apart from Sister Agnes, the rest of the sisters seemed to have found a new fascination with my body that they wanted to exploit. Mother Superior never mentioned my day alone with Sister...

2 years ago
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Penguins Preference a Toby Wakefield storyChapter 4

All through the seventh grade, I could hardly concentrate on my schoolwork. I thought a lot about Ray’s sister Kathy, with his boner stuck up against her thing (by then we heard the older boys referring to it as a pussy and sometimes a cunt). I was wishing I could put my pecker there and shoot on her as Ray did. It would get slippery enough for me to get it inside her. I longed for summer when we would have time on our hands and could sneak away to the woods with Kathy ... find some things...

2 years ago
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Penguins Preference a Toby Wakefield storyChapter 12

The summer of 1953 presented me with the most preposterous sexual adventures that any teenager—any man of any age for that matter—could hope to experience. Sometimes while it was happening, I had to pinch myself to remind me that I was awake Kathy and Rosie were two girls who were a slice of my “coming of age” which was probably a lot more than most boys going through puberty ever experienced. My involvement with Kathy and then Rosie could be claimed by many young boys who have gone through...

2 years ago
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Penguins Preference a Toby Wakefield storyChapter 13

When Kathy and Rosie came into the kitchen Mrs. Warren said, “Well, you girls look like you really enjoyed yourself. I bet you silly things were just giggling your heads off.” Rosie gave her friend’s mother a demure smile as she pictured Kathy’s father “eating” Mrs. Warren’s pussy. Before she had come to the Warren’s house that morning, she knew so very little about sex. Now, her horizons were on the rise. After “going down” on each other Rosie realized that Kathy knew so much more about...

4 years ago
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Penguins Preference a Toby Wakefield storyChapter 3

The world remembers Saturday, November 1st, 1952, as the day the United States detonated the first thermonuclear bomb on Eniwetok atoll in the Pacific Ocean. But in Burling Village on that day the explosions I remember are the personal ones that would change my life forever. At the age of seventy-six few days go by when I don’t think of Sister Natalie. Having lost my virginity that day to Sister Natalie Callan, 40-year-old Mother Superior of St. Bartholomew’s Convent I have forever revered...

3 years ago
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Rina Strelnicov a Toby Wakefield storyChapter 4

This was an unusual Saturday: coffee with Ms. Strelnicov in the morning on the way to work a St. Bart’s. Then on my way home, she was working in her garden and waved me in as I was passing on my bicycle. Inviting me to share a glass of iced tea on the patio she gave me a blowjob which ended up fucking on the outside couch. Then all of this. I do not know the extent to which Sister Natalie, Mother Superior of St. Bartholomew’s Catholic Church had to do with me being there or if this was just...

1 year ago
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Penguins Preference a Toby Wakefield storyChapter 11

Just after Christmas break during the first year I worked at St. Bart’s (it was 1952) I went out for the track team at school. My coach found out that I was a good middle distance runner. I did well in the half mile and the mile, so well that he put me on the varsity track team (I was a freshman). We took group showers back then and after practice I would go into the shower, a large room with six shower heads. In those days we didn’t cover up in any way. There I was naked as a jaybird amid...

2 years ago
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The Masked Lady Of Wakefield Hall

THE MASKED LADY OF WAKEFIELD HALL By Sylvia Who? It was in March 1774 that the rural district of Wakefield in the County of Leicestershire had its first experience of robbery on the King's highway, following the sudden appearance of a mysterious woman, dubbed by the local populace 'The Masked Lady', who was considered either a legend - or to some people a scourge - until she melted away once more into the shadows just as suddenly, never to be seen or...

1 year ago
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How Toby Willis Lost His Soul

Toby Willis stepped off the plain and padding his chest, he took a deep breath and smiling thought, "New Orleans, here I am at last" he managed to get through the busy airport and once out, he flaged down the first cab he saw and off he went. Toby Willis was a man on a mission. He owned his own business and had been long overdue for some R and R and was ready to make up for lost time. Toby Willis was a big man at 6’1” and he weighed in at a whopping 300lbs and counting, with fish belly white...

Interracial
2 years ago
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Peeping Toby

"whoa!.....stop.... there's somebody there!" Sarah said.Reluctantly pulling myself away from her erect nipple, quickly scanning the trees and foliage.....seeing nothing.Getting my breath for a second before asking"Where?...I can't see anyone" Taking her hand away from my crotch she points to a dense clump of bushes with a small gap between them and a big tree, about 50 yards away. Now I could see him. But only just, I'd been looking in the wrong place or rather wrong height, as this guy was...

2 years ago
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Toby and Pub guy

By the end of April 2010, I estimated I had slept with around 40 new lovers in the past 5 months; the vast majority (31) were from David’s former company. None of these liaisons had been ‘just the one night’: most by that date had been 3 or 4 meetings. David’s dare for his ex-colleagues was if the guy contacted me I was to say yes to meeting “for a drink”, I was to dress up sexily, his dare was to at the very least give the guy ‘a blow job’ at the end of the evening, in fact whilst I did blow...

4 years ago
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Toby and Hannah takes it to the next level

Hannah woke up the day after. The two other guests had already left Hannah noticed. It didn`t quite dawn on Hannah what exactly had happened only after 5 minutes of slumbering. At first she got scared, or shocked rather. She lie completely still, thinking about whatever had happened the night before. Upon some pondering of consequences she started thinking about what actually had happened, how Julie had gone down on her, how Toby had fucked her from behind and how she had sucked the balls and...

Group Sex
3 years ago
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Amanda Adventures 2 Amanda introduces Toby to Ka

Amanda and Toby parked the car and proceeded to the shopping centre (meadow hall) and met Katie there. Katie looked gorgeous and extremely sexy she was wearing a summery floral print dress which hugged her figure and attenuated her slim waist and exaggerated her already ample tits.Her eyes lit up when she saw Toby, has did his when he saw her.My wife Amanda also looked stunning, she wore a grey flannel skirted suit which was very tight. The skirt was just above the knee and she wore very high...

1 year ago
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Amanda Adventures 2 Amanda introduces Toby to Katie

Amanda and Toby parked the car and proceeded to the shopping centre (meadow hall) and met Katie there. Katie looked gorgeous and extremely sexy she was wearing a summery floral print dress which hugged her figure and attenuated her slim waist and exaggerated her already ample tits. Her eyes lit up when she saw Toby, has did his when he saw her. My wife Amanda also looked stunning, she wore a grey flannel skirted suit which was very tight. The skirt was just above the knee and she wore very high...

Interracial
3 years ago
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Toby

Several months after I opened my gallery in a small town, I met Mannie’s son. Mannie owned the shop across the road. Mannie and his wife Shirley had both been married before, and Toby was Mannie’s son from a former marriage. Toby was twenty-six years old and about six feet tall. Facially, he did not resemble his dad at all. Mannie was sixty years old, a fact I was aware of having attended his birthday party a month before. For a guy of his age, Mannie was rather good-looking and I could not...

Gay Male
3 years ago
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The Infection Vector Chapter 3 Toby

Author's Note The gaps in the narrative must necessarily widen, or this tale will never be finished. Some of them will be filled in the next chapter, which is also the climax. After that there'll be a two-part coda, drawing as many loose ends together as possible. 'Feggie' is Hartlepool slang for 'me first', as in 'feggie in the shower' A 'rarf' is one of the many terms used in the Hartlepool area to refer to a particularly stupid person The Priory Inn,...

3 years ago
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Toby and Hannah takes it to the next level

Hannah woke up the day after. The two other guests had already left Hannah noticed. It didn`t quite dawn on Hannah what exactly had happened only after 5 minutes of slumbering. At first she got scared, or shocked rather. She lie completely still, thinking about whatever had happened the night before. Upon some pondering of consequences she started thinking about what actually had happened, how Julie had gone down on her, how Toby had fucked her from behind and how she had sucked the balls and...

3 years ago
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Toby and Jo Valentine

This is a Valentine's gift to my beautiful mate, she agreed to let me put it up here for some odd reason. I'll probably write more down the road and for an idea of what the characters look like I put descriptions in another file called Toby and Jo. He could feel something was different the moment he came in the door, of course the scent of his favorite scented oils might have been the first indication but there was also the feeling he only got when Jo was going to pounce on him from some...

3 years ago
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Tales of Culverin HillChapter 4 Jessica Andrew Toby

Present Day “Are you boys ready to go?” called out Jessica Parnell, standing at the bottom of the steps. “Coming, Mom!” came back a loud yell from down the hallway to the bedrooms. Jessica continued standing at the foot of the steps, waiting for her sons to come down, and was on the verge of summoning them a second time when she stopped. One of the bedroom doors opened with a crash and then came a thunder of feet as her two teenage sons rumbled down the hall and down the stairs. “We’re...

3 years ago
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Toby Chapter 01 Tonight Is The Night

Toby - Chapter 01: "Tonight Is The Night" By Kim Em Copyright (c) 2001 I guess it's over now Because I've never seen so much Never seen so much, never seen So much blood In all the confusion, there's something serene I'm just a posthumous part of the scene Now I'm floating above looking in As the radio blares and wheels spin I can see my face slump with a grin You're the last thing on my mind You're the last thing on my mind You're the last thing on...

3 years ago
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Toby the Humper

[url=http://xhamster.com/photos/view/3701034-61947110.html][img][/img][/url]My friends in high school all came with benefits. I originally had no interest in Toby. There was nothing about him that was attractive to me. He was just your average teenager until I saw the video. There was a video circulating around of him getting off. It wasn't your typically guy jerking video. Apparently Toby likes to hump, people, furniture, whatever he can press his cock against. The video was of him humping a...

1 year ago
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392 THEENLIGHTENMENT OF TOBY TRIM PT3

Together Toby and his mother sorted out the meal for the family, fully dressed now, and waiting Cyril`s tractors usual noisy return, they talked over the inevitable mug of tea, Beryl asking if he had enjoyed their ‘romp’ as much as she had, his broad grin, and enthusiastic nod, said it all, then he asked if she was serious about both being tied and spanked and “how would he know to stop?” adding “How many slaps did she want?” she looked thoughtful, then said, “I don’t know, I may not like it at...

1 year ago
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Toby and Angienaked in SchoolChapter 2

Tuesday Morning Toby Angie and I arrived at school at the same time, and parked next to each other. I asked her if she had her new purse and accessories. She grinned and pulled it out from the seat next to her. I told her to always keep the purse oriented so she could get to the gun, even while driving. We got to the door, and looked at each other. "May I?" I asked her. "I thought you'd never ask", she answered. With that, I slowly unbuttoned her blouse, and removed it, placing it in...

3 years ago
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Toby

It was the middle of summer in the quite seaside town of Ormond By The Sea so naturally it was hot even with the constant breeze that flowed in off of the Atlantic Ocean. Being just north of Daytona we didn't get many tourists up this way. This meant that we locals had the same white sandy beach without the crowds and we liked it that way. One particular Saturday my friend Steve had gone away with his parents for the day so I was pretty much on my own and bored. I went down to the beach to...

3 years ago
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Rosie loss and redemption by submission to a Lesbian Gynarchy

Rosie Rosie was my daughter's best friend from the age of six. They shared a birthday, and given her particular family circumstances, she came round to our house a great deal. She was always different. Elfin, very pretty, she had more energy than anyone I have ever known. She was funny, hyperactive and extremely intelligent. She loved gymnastics and riding her pony. When she cycled round to our house in her jodhpurs on her way back from the stables, which was next door (the...

3 years ago
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Toby My Best Friend Part 1

Toby and I had been friends for as long as I can remember. My Mom has a photo of us, sat in a ball pit in the local nursery, grinning like morons. Are teeth are gaped and there are stains on our faces and clothes, but do you know what? We’re happy, and really don’t care. But unfortunately you can’t stay like that forever… We stayed best friends, right up through all our years at Primary school. We were friends, and no one got between us, not even the bullies that took the piss out of my...

1 year ago
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Toby My Best Friend Part 1

Toby and I had been friends for as long as I can remember. My Mom has a photo of us, sat in a ball pit in the local nursery, grinning like morons. Are teeth are gaped and there are stains on our faces and clothes, but do you know what? We're happy, and really don't care. But unfortunately you can't stay like that forever... We stayed best friends, right up through all our years at Primary school. We were friends, and no one got between us, not even the bullies that took the piss out of my...

Love Stories
3 years ago
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Toby and Angienaked in SchoolChapter 3

Wednesday Morning Angie God, what a night. I'd dreamed I was sitting on Toby's face, letting him eat me until I came at least ten times, and then he'd fucked me crazy. 'Get a grip, girl', I kept telling myself. 'He's eight years older than you'. Toby picked me up at 7:30 for school, fully dressed. I was just in a skirt and blouse, with no undies. I had a bra and panties in my book bag, though. When we got to school, we went to the undressing area, and there was quite the crowd....

1 year ago
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Rosie and Steve Part 7

She smiled as she thought of how Beatrice, her daughter, had loved to ride in the cart when she was that age, but only if daddy pushed. Her smile faded as she remembered the day Beatrice discovered the man she knew as Uncle John being her biological father. Beatrice grew more distant from her parents after Rosie's split with Steve; after university, Bea moved out of their home and in with friends, contact with her mother dwindled, it was mainly one-sided anyway; Bea never rang her mother,...

2 years ago
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Rosie and Steve Part 5

Introduction: Rosie pines for her massive cock and Steve gets revenge Rosie wasnt quite herself. For a few weeks now shed been moping around the house. She felt like there was something missing. Steve was working from home, he told Rosie that his part of the project was over, which it was, but he just couldnt concentrate at work. After witnessing Rosie cheating without his consent last month, he still didnt know what to do about it. He was naturally laid back, which annoyed Rosie sometimes,...

1 year ago
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Rosie And Pauline

The two ladies walked up the steep stairs to the heavy-looking wooden door. “Welcome to my humble home” Pauline exclaimed jokingly and she unlocked the door and thrust it open. Pauline was a fuller-figured woman in her late forties with greying hair and a pretty face. “Same as I remember it” replied Rosie as she stepped inside carrying a small brown handbag over her shoulder. Rosie was heavily pregnant and despite her huge bulging midsection managed to look luscious in a tight fitting red...

Fetish
3 years ago
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Rosie and Steve Part 6

Introduction: Alls fair in love & war. Adventures in Rosieland 6 It was quiet in the house, Beatrice was at school, Rosie couldnt believe her little girl was sixteen now. Melissa, Beas half, and now step-sister was also at school. People often remarked how much the two girls looked alike, but never in front of John, there were rumours around that he wasnt Melissas father, which hed obviously heard whispered behind his back, but he payed them no mind. Steve had left her. She blamed herself, if...

1 year ago
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Rosie Wont You Please Come Home

That there’s a whore at her core is a well-kept secret. For she’s been scarred too many times. Certainly fuckable, the thinking went, but, stripped to her emotional core, was she then lovable?The morning sun crept through Rosie’s apartment window. Flickering across her porcelain skin, the rays reclaimed ever-changing patches of her taut physique from the shadows. Highlighting the genetic lapidary which had sculptured delicate beauty from granite, but not bright enough to reach the heart she’d...

BDSM
3 years ago
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Rosie Robert a Merc

Also had the small stains on the passenger seat, made by cum dripping onto it, remained - happy memories of one day during a hot, in more ways than one, summers day a year ago. I had often travelled along the same road in the vain hope of finding them again, but to no avail. While in the area, I had discovered a fantastic little country inn overlooking a lake, which served fresh caught lobster straight from it. A couple of times each month during the summer, I had gone up there to enjoy a...

2 years ago
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Rosie

Rosie Part 1 Rosie was my daughter's best friend from the age of six. They shared a birthday, and given her particular family circumstances, she came round to our house a great deal. She was always different. Elfin, very pretty, she had more energy than anyone I have ever known. She was funny, hyperactive and extremely intelligent. She loved gymnastics and riding her pony. When she cycled round to our house in her jodhpurs on her way back from the stables, which was next door...

4 years ago
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Rosie lured me in with offers of her sister

Rosie is a nineteen year old work colleague of my wife; she is gorgeous and has a great body.Recently I was asked by my wife to teach Rosie how to give a blow job in her presence. I accepted the offer and it went well.A few days later I met Rosie again and this time we were alone and had a great evening of sex.Rosie has since that day been pestering my wife for further lessons, albeit she knows nothing of the second meeting. My wife has so far been reluctant to share my cock again with this...

Group Sex
2 years ago
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391THE ENLIGHTENMENT OF TOBY TRIM 2

391THE ENLIGHTENMENT OF TOBY TRIM 2Cyril came home, tired as usual, the big tractor, his home by day, needed filling the oil checking, and parking up, Beryl heard it arrive, her queue to serve his meal, Toby seeing to filling and parking the great b**st for him, a little thing he did for his dad each day since he had learnt to handle the big machine as a youngster. Little was said, hoeing a couple of fields of cabbages tended not to give a man much to talk about. Beryl being a brilliant plain...

3 years ago
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Toby Jones

I picked her up and put her on the table. Her robe came open and I could see her tits. I reached up and squeezed them and began to rub her nipples. "No! No! Please Toby, you can't do this. Steve is your friend and my husband. Please don't do this." Her mouth was saying no, but her body was saying yes. I saw the wetness forming on her white panties. I stood between her spread legs and began rubbing her pussy with two fingers. This incident took place over a year ago. I'll tell you a...

2 years ago
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Toby and Angienaked in SchoolChapter 6

SATURDAY Angie I awoke entangled in Toby's arms and legs, our nude bodies tied together. God, I could get used to this in a hurry. I had to pee, and I did my best to sneak out without awakening Toby, but it didn't work. "Where are you going?" he asked. "Gotta pee", I told him. "Sounds like a good idea; I'll use the other bath", he said. We reunited in the bedroom, where I got on my hands and knees, and wiggled my ass at him. "The bandage doesn't turn you off, does it?" I asked...

1 year ago
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Rosie

Many years later, after taking my virginity, Rosie would tell me that it was what I wrote to her in third grade that initially endeared me to her. A couple mean boys had taunted her about her skin color on the playground and I was a silent observer of the incident. My heart went out to her when I saw her lower lip tremble, followed closely by a steady stream of large tears wetting her dark cheeks. She didn’t run away in spite of the hurt put on her by her young white tormentors. She just stood...

Interracial
2 years ago
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Rosie 6

Rosie Part 6 I will not dwell overlong on my experience with Annabelle and Georgie after leaving Rosie's room. To my relief, their response to my knock, entry, curtsey to the room, curtsey to Annabelle, reading at the desk, and Georgie, luxuriating in the bed, together with the prescribed greeting, was laughter. Annabelle's greeting was a question as to why I was wearing a pair of soaked panties over my face. I burbled an explanation about how it was my fault, that I had asked Miss...

2 years ago
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Rosie Megs plus a Merc

As a driving instructor and examiner, I loved driving, and teaching people to drive - cars and motor bikes. I was out cruising, enjoying the drive and seeing the scenery all around me. The windows were down allowing a gentle breeze to blow through the car, keeping the temperature at a comfortable level. Ahead, I saw two small figures at the side of the road, thumbing a lift. I started to slow my Mercedes, a top of the range luxury model, having no qualms about picking up strangers and...

1 year ago
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Rosie wanted another lesson

Just last night whilst driving home I saw Rosie walking through the estate.Only last Friday I had reluctantly (not) offered my cock to Rosie to use so that my wife could teach her the art of oral sex. Rosie had a new boyfriend and did not want to appear like an amateur and wanted to give him 100% pleasure.Anyway I pulled the car over and rolled the window down and called out to Rosie.Rosie came running over and asked if my wife had passed her message on."What message would that be?" I...

Oral Sex
2 years ago
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Rosie 5

Rosie Part 5 I turned to leave, my gut churning with the thought of how I could approach Annabelle and Georgia with Maria's panties over my face and my 15 hour erection outlined clearly in my silky pyjama bottoms. I felt a combination of fear and excitement, and it was only the fact that Rosie had commanded me that it made it possible to go through with it. "Wait!" Rosie's voice drifted languidly to the door, like the smoke from her cigarette. "I've got another present for...

4 years ago
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Rosie

Here is a story about my ex wife and I from many years ago, reading the stories on here regarding cuckoldry and extra marital sex I thought I would share this with you.Rosie my wife a nice looking farmers daughter not skinny not fat just nicely made pleasant to be with and we had a nice life nothing startling but we were happy.This all took place in the seventies I was working long hours and Rosie (name changed) worked in a small office in a local processing factory. We had been married around...

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