Maddie And Connor free porn video

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Connor wanted it so much, but he was nervous.
He'd been fantasizing about it for so long but now that it was actually about to happen he felt afraid, he didn’t know if he could handle it.

"Don’t worry Connor baby, I'll be gentle", she told him in a reassuring tone as she ran her fingers down his spine and sides.

The sensation of her fingertips against his bare, oversensitive skin made him shiver and grunt in response.

He was naked and on all fours on Maddie's bed as she stood behind him. She could feel he was anxious and that he needed to be touched, so she leaned over him and kissed down his back with slow deliberation all the way to the top of his ass. That made him stick his ass out at her as if begging her to start, he wanted her to take him. She licked her index finger and just ran it around the edge of his virgin rose bud making him suck in a deep breath. He knew he could trust her not to take it too fast or be too rough with him but still he wasn’t even sure he could handle her taking it slow and easy.

When he confided in her and told her what his secret desire was he was sure she would find it disgusting and turn him away, but to his great surprise she was not only unfazed by it but had actually done it before and was completely turned on by it. And that is how they ended up here, in his bedroom, with her now rubbing a good amount of lube between his ass cheeks and him biting his lips.

She was massaging his anus more firmly now, warming him up, getting him excited as she simultaneously rubbed his cock. He was rock hard and panting as he felt her push her finger against his opening with some purpose to it. He felt pain flash through him as she pushed it in to her first knuckle and he cried out. He wanted to resist her, to push the intruder out of himself and make this stop.

"Don't fight me baby," she told him, "just try and relax your muscles and I promise it will feel better soon."

He nodded his head in response and tried to focus on letting go, he knew that it will be ok because she was with him. His cock wasn’t as hard now as before, the pain had made his erection subside a little so she stroked him for a few minutes before pushing her finger deeper inside up to the second knuckle. There was the pain again but this time he bit his lip and tried to focus on the hand wrapped around his cock and not the finger that was insistently pushing into his anus.

She kept her finger in him and wiggled it a little and he felt his stomach tingle with the unknown sensation. He was starting to enjoy it and get more excited about finally fulfilling his fantasy. She pushed her finger all the way in and the pain was mingled with pleasure for him, he moaned lustfully and even pushed his ass to meet her.

"You are doing so well Connor," she leaned over him and playfully bit his earlobe. "Do you like it? Do you want more?"

"Yesssss…" he moaned in response and wiggled his ass a little.

Her finger started moving inside of him, in and out, at first slowly and then picking up pace but she wasn’t stroking his cock anymore- she didn’t want this to end too soon, she wanted his orgasm to be the prize at the end of the road for him. She kept finger fucking him for a bit, letting him feel the rhythm until he started moving on his own and pushing back onto her, at which point she thought it was time for a second finger. As he felt the two fingers going in he panicked a little, fearing that he couldn't stand it, but his rear muscle was softened by the activities so far and took them in without much resistance or pain. actually the pain was so minuscule it barely existed while the pleasure of being full was overwhelming, it made him tingle all over and the desire to cum was very strong despite his cock not being stimulated.

"You are so sexy Connor," she told him in her sensual voice. "Your tight ass is making me very wet and horny."

"Oh fuck, is it really?" he moaned in ecstasy- it was by far the sexiest thing anyone had ever told him.

"Yes it is, would you like a taste?" and with that she dipped the fingers of her free hand inside her wet snatch and brought them to his mouth, coated in her juices.

"God yesssss..." he moaned as she shoved her wet fingers into his mouth and he sucked on them.

"I think you are ready for something bigger in that hungry little ass of yours, sexy boy," she told him as she felt he was pushing himself unto her fingers harder and faster.

She withdrew her fingers and stepped to her bedside table where she pulled a toy out of the top drawer. The toy was a blue but plug about 4.5 inches in length and 1.5 inches in width, cone shaped with a wider base. Maddie turned and showed him the toy she had just pulled from the drawer.

"Do you think you can handle this?" she asked him seductively and then put the toy in her mouth, lustily sucking on it.

He gasped as he looked at her, her hand sneaking down to rub her clit as she sucked on the rubber plug and looked straight into his eyes. This was far exceeding what he had expected this day to be like, and to think he almost didn’t tell her about his desires. She moved closer to his face as he still stood on all fours; she lifted one of her feet onto the bed so that her pussy was spread open inches from his face and slowly inserted the plug into her sopping wet slit. He could smell her juices and hear the squelching of the toy as she moved it in and out of herself.

"Soon this will be inside you Connor. Are you excited?" she asked with a wicked grin.

He had no time to answer her question as she pulled the plug out of her hole, all wet and shiny with her liquid and pressed it against his slightly parted lips, making him take it into his mouth. It tasted so good after having been inside her that sucking on it was a pleasure.

"I see you are enjoying yourself," she teased him. "You better make it nice and wet so it’s ready for your ass."

Her words made him shiver with need and desire for what she was promising him. He increased his efforts on the toy, slobbering over it to show her his desire. After a few more seconds, she pulled the toy out of his mouth and moved to stand behind him. His cock was rigid with arousal and she cupped and squeezed his balls lightly just to make him moan.

He felt the toy against his asshole as she teased him with the tip; it was so smooth and wet with his saliva. He instinctively spread his legs wider, preparing himself for the object that was about to invade his most private and sensitive place. He felt her put more lube and probe the tip of the plug more firmly against his opening and made an effort to relax so that it could enter him more easily.

"That’s right Connor baby, relax and let it in," she told him. "You know you want to; you know it will blow your mind."

"I'm trying," he whimpered in response as the pressure against his puckered hole increased.

There was pain again as the plug was slowly but surely being pushed inside him; he thought of crying out for her to stop when the plug was about half way in but he didn’t, he bit his lip and held on to her bed sheets so hard that his knuckles were white.

Again she wrapped her hand around his cock, which wasn’t rock hard anymore, the pain having its effect on him. She stroked his cock slowly but with purpose as she kept pressure on the toy going into his tight ass hole. She knew from experience that the first time was going to be difficult and painful but she also knew the pleasure that the anal penetration could bring, especially to a man. The toy was almost in him, he only had to take in the wider part and then he could start to really enjoy himself.

"Connor baby, it's going to be a bit more painful now, but I'll do it quickly, so just hold on and it'll get soooo good after that," she told him matter-of-factly.

"Ok," he nodded his head and braced himself.

"Here goes," she said as she gave one forceful push and the plug went all the way in with a little popping noise.

Connor screamed with pain as the toy fully invaded him; to him it felt like an electric shock ran through his body. His muscles tried to push the toy out but it was not going anywhere. She kept stroking him with one hand and caressing his lower back and ass cheeks with the other, waiting for him to get used to the intruder in his rear opening.

Slowly but surely the pain started to subside and he could feel the pleasure take its place. Every part of his body was suddenly a lot more sensitive and the feel of her stroking him was electric. Despite being in pain moments earlier, now he felt like he needed to cum, and cum hard. He could not describe what exactly was happening but it was incredible and oh so good- just like Maddie told him it would be. He began moving his hips to meet her hand, wanting it faster and harder, and each time he thrust, his muscles would contract around the toy and make him feel even better.

"That's right Connor," she encouraged him. "Doesn’t that feel like heaven?"

It didn’t feel like heaven though, it felt like a fire ball was inside him, it felt as though he was peeing cum, as though he was about to pass out and still keep cumming. He was screaming and cumming and unable to stop or understand what the fuck was happening.

When his orgasm had finally subsided, he collapsed on the bed, breathing hard and trying to regain some semblance of self-control and logic. He felt spent and exhausted. He looked at Maddie who sat down on the bed in front of him and smiled at her.

"So did you enjoy it as much as you thought?" she asked with a grin.

"Way more than I ever thought," he answered honestly.

"Well now it's my turn to enjoy," she told him with a wink.

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Well, now it's time for school. Candace and I go to a small high school, not private, but because we are so rich, it is not exactly public either. The students have been screened by my fathers' security teams; they are all exceptionally bright, well mannered, not prone to causing trouble, and to add ice cream to the pie, all are very good looking. There are 40 students, 20 boys and 20 girls. When the school was larger it had state champion quality teams in boys basketball, girls volleyball...

2 years ago
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Handyman Candys Cabana

This is a story about a sexual FANTASY written for consenting adults. If you're not both of those, don't read it. Characters in a FANTASY don't get sick or die unless I want them to. In real life, people who don't use condoms and other safe-sex techniques do get sick and die. You don't live in a FANTASY so be safe. The fictional characters in my stories are trained and experienced in acts of FANTASY - don't try to do what they do - someone could get hurt. If you think you know somebody...

1 year ago
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Nandhini Chechi Breastfed And Got Fucked

Dear sexstory friends, this is Rajesh presently working in Bangalore in an MNC and I would like to share my past experiences with you people. I am a 38 years old horny man with a slightly big cock of 8 inches and satisfied many girls and Aunties from past 20 years. Any unsatisfied girls, Ladies and widows can feel free to chat with me on The incident happened when I was 18 years old and studying PUC in Bangalore, when a new Malayali neighbours occupied the vacant house next to our home. They...

2 years ago
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Andrea Andy and Me

(MMF, wife sharing) At the time I write this story Andrea, (My wife) is 36 years old, and quite a knockout. She's always been into bodybuilding and has been a runner since she was a k**. With all of the attention that she has given herself, it really shows. At her age she still has a hard body, and a deep rich "California Girl" tan. Her chestnut hair is beautiful. And her dark brown eyes seem to see right through me sometimes. My Andrea is a beautiful "self made" woman that any man would be...

2 years ago
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Gorgeous Indian Chechi Nandhini fed me her excess

Nandhini Chechi fed me her excess breast milk and surrendered her pussy to my 8” cock.Dear friends, this is Rajesh presently working in Bangalore in an MNC and I would like to share my past experiences with you people. I am a 38 years old horny man with a slightly big cock of 8 inches and satisfied many girls and Aunties from past 20 years. Any unsatisfied girls, Ladies and widows can feel free to chat with me on [email protected] The incident happened when I was 18...

3 years ago
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Becoming Brandee Chapter 14

Disclaimer: This chapter, like all chapters of the Brandee series is intended for adults only. Additionally, no part of this story may be reproduced without the permission of the author. Becoming Brandee Chapter Fourteen: It was almost a year since I had been transformed from smart independent CD girl, Jenni, into sweet dumb and adorable bimbo, Brandee. It was also Halloween and the final evening performance of my promotional tour being staged back where it all started, the...

3 years ago
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Andee Plays a New Version of Around the World

Andee felt a little reluctant as she stared at the calendar hanging on her kitchen wall. Scribbled in among her children’s sports and music lessons were the pending dates of her fall travel schedule again. At one time, she loved the idea of jetting off for a few days every month to another distant location for business, easily slipping into her professional role as a career woman on the move; but this time around, she felt a little hesitant.Of course, a big part of her reluctance was a direct...

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3 years ago
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Andee Plays a New Version of Around the World

Andee felt a little reluctant as she stared at the calendar hanging on her kitchen wall. Scribbled in among her children’s sports and music lessons were the pending dates of her fall travel schedule again. At one time, she loved the idea of jetting off for a few days every month to another distant location for business, easily slipping into her professional role as a career woman on the move; but this time around, she felt a little hesitant.Of course, a big part of her reluctance was a direct...

Wife Lovers
3 years ago
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Andee Poses For A College Art Class

There weren’t many people in Andee’s day-to-day life that knew about her naughty little secret. Even though she had been posing on an adult website for over twelve years, she had managed to keep it under wraps for the most part; and the people to whom she did disclose the information fell into two categories: intimate friends and persons of seductive interest.Her good friend Bella – a wild one in her own right – was someone Andee had entrusted with the knowledge. In fact, Bella had often played...

Wife Lovers
2 years ago
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Andee Poses For A College Art Class

There weren’t many people in Andee’s day-to-day life that knew about her naughty little secret. Even though she had been posing on an adult website for over twelve years, she had managed to keep it under wraps for the most part; and the people to whom she did disclose the information fell into two categories: intimate friends and persons of seductive interest.Her good friend Bella – a wild one in her own right – was someone Andee had entrusted with the knowledge. In fact, Bella had often played...

Wife Lovers
4 years ago
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Andee Learns Just What Stays in Vegas

Andee carefully removed the letter from the envelope. She had just come home from work to find it placed on her pillow, plainly marked "Just For You." She knew it was from her husband, as he had departed on his business trip earlier that day. And, as he often did, he had some scheme cooked up to add a little excitement to her life. This time the plan was for her to travel to meet him at the end of his trip in Las Vegas. He was attending a trade show and managed to get an extra flight. What she...

Wife Lovers
4 years ago
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Fernanda Teenage Lust

I had just finished my first year of college and my mom and dad insisted that I go with them on a quick summer trip to visit one of mom’s old college buddies in Austin, Texas. Normally, I don’t mind such gatherings, but for some reason or another, Austin just didn’t appeal to me. I had been there many years before and didn’t find the city attractive. When we arrived, there were the customary hugs and greetings- since our family is Hispanic. (You have to love a culture that embraces hugging!) I...

First Time
3 years ago
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Andee Returns to Las Vegas

Andee settled in for another flight. Her new job had been taking her all over the place the past few months, but the light was almost at the end of the tunnel. This trip to Las Vegas would be the last for the year. The other bonus is that she only had to spend a couple days on her own, as her husband had managed to make some changes to his own plans and would meet her for a bit of an extended weekend. The last time they had been together in Sin City, things had been … interesting. It was a...

2 years ago
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Andee Returns to Las Vegas Chapter 2

Andee smiled as she read the text message on her phone. Before breakfast, she had sent a somewhat vague note to her friend from the night before about wanting to try Roulette again, wondering if he might interpret the suggested sexual undertones – especially after the enthusiastic round of sex from the night before. She thought for a moment, wondering just how acquainted she wanted to get with Connor. It seemed her “one-night stands” in her sexual adventure were more like weekend-long affairs,...

Wife Lovers
3 years ago
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Andee Returns to Las Vegas

Andee settled in for another flight. Her new job had been taking her all over the place the past few months, but the light was almost at the end of the tunnel. This trip to Las Vegas would be the last for the year. The other bonus is that she only had to spend a couple days on her own, as her husband had managed to make some changes to his own plans and would meet her for a bit of an extended weekend. The last time they had been together in Sin City, things had been ... interesting. It was a...

Wife Lovers
2 years ago
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Andee Returns to Las Vegas Chapter 3

Andee held her coffee in both hands as she sipped on it. Thecombination of her hangover, sexual exhaustion and lack of sleep, left her struggling to bring her mind around to some sort of clarity. Her hands were a little shaky as she stared blankly at the cup. “I’m not too sure about all the details,” she mumbled across the table at her smiling husband. He seemed to be enjoying the whole thing a bit too much and had been pressing her for some information about her encounter. She hadn’t yet...

2 years ago
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Andee Returns to Las Vegas Chapter 3

Andee held her coffee in both hands as she sipped on it. Thecombination of her hangover, sexual exhaustion and lack of sleep, left her struggling to bring her mind around to some sort of clarity. Her hands were a little shaky as she stared blankly at the cup. “I’m not too sure about all the details,” she mumbled across the table at her smiling husband. He seemed to be enjoying the whole thing a bit too much and had been pressing her for some information about her encounter. She hadn’t yet...

Wife Lovers
2 years ago
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Ms Nandhini ndash My School Teacher Chapter 2 How

Ms Nandhini – My School TeacherBy KINGPHANTOMEmail: [email protected] 2Lesson – 1 – How to MasturbateThe morning after I Dry Humped our new class teacher’s ass on our school bus. I woke up hearing my older sister Nithya chechi (Starring “Nithya Menon”) calling out my name. “Shyam you idiot, come on get up. You are late for school. I am gonna tell mom, you better get up.” She shouted at me. It’s a curse to share a room with your older sister. She wants to decide on everything that’s...

4 years ago
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Andee Heats Up Houston Day 1

Andee edged her way through the crowd surrounding the luggage belt. She was happy to finally be off the plane after the three hour flight from Toronto, but still had some peculiar emotions about being in Houston. Ever since her encounter with Don back at the conference in Chicago she had been maintaining a casual connection with him, mostly on a professional level. When she received his invitation to come to Texas for a few days to explore first hand some of the research developments his...

Wife Lovers
3 years ago
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Maddies Morning Surprise

I wake to a warm ray of sun filtering through the dusty window blinds onto my face and within an instant am struck by the fact that maybe those last couple shots from the previous night were not a good idea. A need for water and aspirin is immediately apparent, but hasty movements are out of the question as well. Better to ease into a hangover. I stretch my body out and that’s when I become aware that I’m not alone in bed, as my foot finds skin behind me. Dammit. Drew. Quickly replaying the end...

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