My Caretaker: Bob free porn video

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Before i get to the main part i would like to tell you a bit about me. I had turned 16, i was a chubby kid, with thick thighs and a big wide ass. I was 5ft 7 and had an average cock. I was an innocent kid, had no exposure to porn or sex. Now my caretaker, Bob, was at this time in his late forties. He had been working for my family ever since i was born, since my family was out of town most of the time. He would cook for me, drive me to someplace and taking care of the house. He would also help me with homework and all. Bob was a complete bear, he was very hairy. Bob was also very sexually active, he had fucked every women in the neighborhood. Bob was like family since he had been with us for 16 years.

Now when all this happened i had my 3 months vacations. My family always took me with them on their trip when i had vacations but this time i decided to not go. I was home alone with Bob. The first week nothing happened, i spent most of my time in my room playing on my xbox. Bob would often come and give me food. Now it was really hot these day, Bob has his own room but it had no Air conditioner, well mine did. Bob one day asked if he could sleep in my room, i had no issue with this i considered him family.

At night bob came to my room, sighed about how cool my room was. I played on my xbox and he also joined in but had no knowledge of game, I taught him how to play and we played till 2 am. It was late and we both were feeling drowsy. Now i went to the bathroom and changed into my boxers shorts, i slept shirtless. Bob kept staring at me, i got on the bed and laid down. Bob also started to unbutton his shirt, he unzipped his pants and stripped down to his white underwear. I was also staring at his body, it was the first time i saw him like this. He got on the bed and slept.

I woke up in the morning earlier than Bob, He was still sleeping. I saw a tent in his blanket, it made me curious, i slowly removed the blanket not to wake him up. His underwear was down to his knees, he was having morning wood. I saw his rock hard cock. It was so big and hairy. It must be about 9-10 inches. Bob was up and he was watching me look at his cock. He however still pretended to sleep to see what do i do. I didnt do anything, i slowly covered him with the blanket and went to take a shower. I was also having morning wood, i couldnt stop thinking about his cock, i jerked off in the shower. I came out and saw he wasnt in the room, he later came and brought me breakfast.

The whole day i couldnt stop thinking about his cock, mine was about half his size. Well it was dinner time, Bob still hadnt brought me my dinner. I went out to look for him in the kitchen, the food was being cooked but he wasnt there. I went to look in his room, i knocked but didnt hear a response so i peeked inside. I saw that Bob was completely naked sitting, he was stroking his cock. It was so exciting watching him jerk off, he had heard the knock but pretended like he didnt. He was stroking his cock faster and soon shot a huge load across the room. He knew somehow that i would watch him and he was right, i watched him jerk off. Well after he finished i ran to my room. The whole scene was giving me a boner. He soon came in with my dinner and left. I thought about jerking off after dinner.

After i had my dinner, Bob came inside, i got no chance to jerk off. He proposed we play something on the xbox. We sath down and started playing. My boner was poking in my shorts, and Bob had noticed this. He was slowly getting closer to me. I could soon feel his legs touch mine. We played for sometime. After that we stripped down into our undies, we were about to sleep. Bob and I were on my bed inside a blanket. Bob took out his phone and was watching something. I could barely hear it, i asked him what was he watching. He replied "Ill get in trouble if i show you this but if you promise not to tell anyone ill show you" I told him i wont tell anyone. He got close to me, like really close and showed me the screen. He was watching porn, My first porn video, it was making me horny. After sometime we were laying side by side, he was behind me. He was slowly getting closer, his cock was touching my back. His hairy chest was touching my back, it was making me so horny, i soon blew a load in my boxers. I told bob i wet my bed, he laughed saying "Did you wet yourself or did u cum?" He told me it was alright and i can just slide my boxers down. Its not like he hadnt seen me naked before, i slide my wet boxers off and we continued watching porn.

Bobs cock was still hard, and without me noticing he slide his underwear and i could feel his cock on my ass. He then changed from straight to gay porn. It was so hot, we were watching a twink suck another guys cock. I turned my face and asked him about gay sex, he told me about his experiences and how much fun it was. He told me that guys liked his cum alot and would swallow it all. I told him that sounded disgusting, he laughed and told me i wouldnt find it disgusting if i tasted his cum. He then said "Would you like to try it out?". At first i said nothing, and then I asked him "Can I?". He removed the blanked and started to jerk his cock infront of my face. He was about to cum, when he was close he asked me to open my mouth. I opened my mouth and then he shot his load, 8-9 streams of warm cum fell on my face and inside my mouth. He wasnt wrong his cum did taste good, he scooped up all the cum from my face and shoved it all inside my mouth. He made me lick his finger.

He laid next to me, still catching his breathe. He turned around and asked me how was it. I responded it was nice. He said if i wanted more i can always ask. I smiled and then we went to sleep. The next whole day i couldnt stop thinking about what happened last night. It was night and we were about to sleep. Bob just got naked and got on bed. It made me wanna get naked too. I got naked and got on to the bed. I wanted his cum again, i just didnt have the courage to ask him. He saw i was restless, he asked me what happened to which i told him everything. He laughed and removed the blanket. He grabbed his cock and said come. I got up and went towards his cock. He grabbed my hand and placed it on his cock. He was stroking his cock with my hand. Then he removed his hand and i continued to stroke his cock. He placed his hand on my head and said why dont you suck on it. I was really horny, i leaned down and opened my mouth. I started licking his cock. He was moaning like crazy. He asked me to take it inside his mouth and suck him like we saw in porn yesterday. I started to copy that and started to blow him.

I was blowing him and he was rubbing his hand on my ass. He grabbed my thigh and pulled me closer to his face. He placed my ass on his face and started to lick my hole. It felt so good i got a boner. He was rubbing his tongue on my hole then he slowly pushed his tongue inside my hole. I let out a loud moan. He was pushing his tongue deeper. He then licked his finger and rubbed on my hole. He slowly pushed it inside, it was a pinching pain but i was able to handle it. Soon his whole finger was inside my hole, he was fingering me. After some time he inserted two fingers, then one more. I was being fingered with three fingers. I was moaning my crazy.

After a good finger fuck, my hole was pretty loose now. He moved me and made me get on all fours. I came behind me, he spread my ass and spit inside my hole. He placed his wet cock on my hole, he slowly pushed inside and entered his tip. I jumped in pain. He told me to relax my hole and then he slowly pushed more. He stopped and gave me rest every time i felt pain. Slowly and gradually his cock was deep inside me. He was licking my ear. After some time my pain was gone, he took his cock out and turned me over. He grabbed my legs and placed them over his shoulder. He entered me again and kissed me. He was pounding me really deep. His cock was hitting my prostate, my cock was leaking cum. I was moaning like crazy, soon he gave a powerful thrust and moaned. His cock was pulsating inside my hole, i could feel his warm cum inside my hole. It made me shoot another load on my chest.

He removed his cock and laid next to me. I eventually slept, i woke up hours later. I was on my stomach, Bob was pounding me from behind. He made me get into doggystyle. He started pounded me, he was simultaneously spanking me. My ass was red due to spanking. He fucked me for 40 mins then placed his cock in my mouth and fucked my face till he came in my throat. I swallowed all his cum. He still had his cock in my mouth. He said "I want you drink my piss" What? I tried to resist but i felt his warm piss in my mouth. It was filling my mouth up, i had no choice but to swallow it down my throat. He removed his cock and i gagged and coughed. He grabbed my neck and kissed me. He said "Suck my cock". I got up and started sucking his piss covered flaccid cock. I sucked him until he was hard again. He asked me to ride him, I got on top of him and sat down on his cock. I was bouncing his cock. He was stroking my cock as well. I ended up shooting my load on his chest and he made me lick it.

He then made me get into doggystyle, he was spanking me and pounding my ass. He fucked me like that for an hour. Then he shot his load inside me. He asked me do you want more, i said no i was tired. He said "Well it doesnt matter if you want it or not". He then started pissing inside my hole. I tried to move away but he grabbed me by my waist tightly. His piss was leaking through my hole. He removed his cock, all his pissed and cum spurted out on his cock and legs. He made me lick him clean and i did. After that we both kissed for a long time before sleeping.

He fucked me again first this in the morning. He also pissed in my hole and made me hold it while he spanked it. I held it for 10 mins but then i couldnt hold it. He made me lick it all. Bob and I fucked everyday. We tried different things. Bob fucked me alot. My parents only came home for a few days, those were the days we didnt fuck.

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Walts Poker Pal Bob

Before I left Chuck's house I asked if I could change into my last outfit for Bob and Chuck agreed. When I finished I has on a one piece out of a short black skirt that barely covered my ass and a sheer black top that easily displayed my tits and a pair of 6" stiletto heels. "OH fuck baby" Chuck said when he saw me come out of his bathroom "You're one fuckin' great lookin' whore" he added and I moved up and kissed him nice and tenderly. When I backed off, "Thanks lover" I said to him "Maybe...

3 years ago
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Plain old Bob

Plain old Bob Janet L. Stickney [email protected] My name, like the rest of my life doesn't make me stand out. Bob. Plain old Bob. I'm only 5'7" tall, average to thin build, weighing maybe 135. I have light brown hair and blue eyes. Just your average fellow. Not big enough to play on a sports team, not smart enough to hide behind a geeky face, or even try acting. My tenor voice doesn't carry well I was told. I don't even have a girlfriend. All in all, I go through the endless...

2 years ago
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The Sexual Education BluesChapter 16 Lori and Bob

In the end, Bob and Lori were all that were left. She still sat on his lap, her arm around him. "Do you want to go do something?" he asked. "No, I like it here," she said, wiggling against him. "Let's kiss some more." "This is going a little faster than I planned," he said, looking into her eyes. "I don't care," she said. "I'm having the most fun of my life. Even the guys looking at me wasn't so bad." "This fun can turn very serious," said Bob, stroking her...

2 years ago
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Bobo

Bobo by Vickie Eggie Simply put, Virginia wanted to fuck. She didn't care who or where just as long as she got some hot male sausage to stuff into her aching pussy. "A girl can only go so long without riding the big shaft," she thought, "and I've gone about as far as I want to go."It had not been all that long. Only yesterday she had screwed the mail boy down in the basement of the building she worked in, and last night Ralph had pumped her cunt full of cum before he had to hurry off and catch...

3 years ago
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What About Bob

With Sarah Goodwoman's kind permission, here is a continuation of her short story WHAT ABOUT THE CHILDREN, an excellent little slice-of-life tale about the everyday hassles of trans people, which you might want to read first. Both stories are very short, and together won't take up much of your time. ===========================0 WHAT ABOUT BOB? (What About the Children Part 2) Laika Pupkino 2017 ===========================0 Esther Krumnagle was furious! The pervert---one of these...

3 years ago
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Becoming A Slut Husband Bob

I suppose that I have my wife to thank although I never will. In fact, I hope to God she never finds out because that would change things and the Good Lord knows that I don't want that to happen. It started the day that I found out that my wife was an unfaithful whore. It was a story as old as time. We had planned to go someplace, something came up and I had to cancel and my wife went alone. I got loose from what I had to do and showed up just in time to see my wife go off with another man. I...

3 years ago
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bobbi

bobbi by dvs For a few seconds, James just stood there looking at bobbi. I’m sure he was soaking it all in. I know I would have. The image of a naked woman, bound and helpless, and that look on her face as she said those words. What man could resist? Not me. James’ face began to glow with desire. I could see those wheels of lust churning in his head as he looked down at her. I’ll say one thing for that slut. She knew how to get what she wanted. She knew the walk and the talk. That wasn’t the...

4 years ago
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Bobbi

Bobbi - New Girl in Town(TV, Transsexual, Prostitution, Gay & lesbian sex, Anal, Oral)[Note: the original author of these stories prefers to remainanonymous]Margo sat next to me in the coffee shop late that Saturday afternoon.His real name was Mark, but he was one of the loveliest Drag Queens inNew York City. I had been dressing secretly at home in my mother's and sister's clothes for just over three years, but at 18 years old, I hadnever been in public as a woman. Margo lived now as a...

2 years ago
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Tommy and Bobbie

As a teenager, sometimes I wished I could go for an entire day without thinking about doing it. From the time I discovered that orgasms felt good, I seemed as if I thought of nothing else but doing it with a girl. I discovered that girls liked to go out on dates with guys, but contrary to the things I heard from some of the older guys, they weren't ready to fall into the back seat of the car after a movie and a Coke. It wasn't for lack of my trying! I heard two seniors talking about...

1 year ago
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Bobbi

Margo sat next to me in the coffee shop late that Saturday afternoon.His real name was Mark, but he was one of the loveliest Drag Queens inNew York City. I had been dressing secretly at home in my mother's and sister's clothes for just over three years, but at 18 years old, I hadnever been in public as a woman. Margo lived now as a female, and couldpass anywhere. I complimented "her" on it, and "she" said, "You coulddo just as well, you know." I was flattered, but not as sure as shewas. "Come...

3 years ago
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Bob Becomes Bobbi

This story deals with sexually explicit material. If it offends or your not 18 or older do go any further. BOB BECOMES BOBBI by TIFFANY [email protected] I was just turning 10 years old the summer I met Marshall. I lived in a small rural town and keeping busy during the summer vacation was always a problem. That's why when Marshall a 14 years old and his 12 year old sister came to visit there Grandparents who lived just up the street it was an opportunity to escape some...

2 years ago
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Transforming Bobbie

Transforming Bobbie It was a typical Monday morning. I woke up, showered, dressed for work and had a glass of orange juice. Everything was fine and then suddenly I felt a "pop" in my lower back followed by a great deal of pain. It was not the first time my back had gone "out" but it was by far the worst time. I called in sick. Then I tried to sit or lay or find some way to ease the pain, but there was no position which would give me any relief. My wife Mary came downstairs. ...

1 year ago
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BOB BECOMES BOBBI

I was just turning 10 years old the summer I met Marshall. I lived in asmall rural town and keeping busy during the summer vacation was always aproblem. That's why when Marshall a 14 years old and his 12 year oldsister came to visit there Grandparents who lived just up the street it wasan opportunity to escape some of the boredom. Marshall and his sister,Jennifer, were from the big city. To them we were all hicks.Marshall was quick to start up an association with me only because I...

2 years ago
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Bobbi

I had my "secrets" we all have them. I guess on the one hand we are terrified we will be discovered but on the other, there is that little part of us that wants to be discovered. At least that's the way it was for me. Meeting Ms. Anders changed all that. Somehow, from that first meeting, she could see all the way through me. She could see that dark secret that I always thought was safely hidden away.I should start at the beginning and maybe this will all make a little more sense. My names...

4 years ago
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Caretakers Dillema

Copyright© 2000 She'd gotten off early Thursday afternoon for a doctors appointment. As soon as she was through with the exam, she headed for the hot springs. David and Ellen would be driving up together Friday afternoon. Almost two and a half decades long, their friendship had been a gypsy sort of thing. Dave had been her housemate, then Ellen's boyfriend. That's how she'd meet Ellen. They'd done the sixties together, then they'd moved to follow the grad school path, while she'd taken...

3 years ago
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Bosomy Bobbie

"It's Bosomy Bobbie," I say to Anne, holding my hand over the receiver. "Tell him we're not here. Tell him we're not her... tell him whatever you want." "He's all dressed, he says. He's got that whiny tone in his voice." "That's the only tone he has!" Anne screamed. "Oh God... why hath thou forsaken me? Alright. Tell him to come over but use the side entrance." "What side entrance?" "You know, the one next to the imaginary elevator." "Oh, that side entrance... Yeah, she...

1 year ago
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Bobbie

BOBBIE Oh Lord, here he is, drunk, falling down drunk, Anna thought. She heard her husband of thirty years come home in his usual state. He spend all his days in the pool hall and his evenings at Maloney's Bar. The fact that he could afford it was not the point. Ever since they won the lottery and he gave up working he spend his days drinking. Half past seven and he could barely walk. He started early. She had attempted to get him help but he was not interested. His...

4 years ago
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Bobbie

It was Saturday night. I was ready to make the bar scene, and meet the girl of my dreams. Well, maybe just the girl of my desires. Or even any girl willing to make out with me for a while. There wasn’t much happening in small-town Iowa these days, and I’d already met every girl within fifty miles. If I got really lucky, there’d be someone new, or at least someone who’d give me a second chance. Otherwise, it’d be Ms. Hand again tonight…It was just after nine o’clock. The band sounded good, and...

Gay Male
2 years ago
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Bobbie

Bobbie By Alyssa Davis I wound my way around to the back door and let myself in to Aunt Mary's house, something I have done routinely for years. Usually I just came over to visit, since I was very close to my aunt. She was like a second mother to me, only I was more comfortable talking to her...to confide in her. She never had children of her own and now, she was a widow. So she considered me like her own son. And as such I did many chores for her. Now that school was out for the...

2 years ago
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Bobbie

I met her in my office. She was assigned to one of the other consultants I share space with, and there was something about the way she moved that caught my eye. She seemed confident, and roamed the office at will. Normally, a new assistant will spend most of her time at her desk, and will only speak to a consultant if spoken to. Not her. She would captivate groups of us at once, telling us flirtatious stories, flashing her playful baby blues at us all. Bobbie was small. I figured her for four...

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