First Time CL Hookup With Older Daddy free porn video

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I'm mostly straight, but as long as I can remember I've been super turned on by the fantasy of bottoming (and submitting) for a much older daddy type, especially the "straight" MWM types. I'm not attracted to guys my age at all, but I find the cross-generation thing to be incredibly hot. I'm pretty masculine and dominant most of the time, but always wanted to sub to an older dom daddy. This is the story of the first time I got up the nerve to actually do it.

I was 22 and in college. I was a regular lurker on craigslist, looking for older tops looking for younger. I'd email with a lot of them, occasionally put up my own posts, but invariably chickened out. I don't know what was different about this time, but it sounded like we had similar interests, we discussed what we both wanted, and I just said fuck it, let's do it. He worked nearby, so we set up a plan after very little chat, and met at his car in the parking lot in the middle of the day and went to his house. He was married, balding, and gray with a bit of a belly, about 55, aka exactly my type.

I was nervous as hell. Here I was, 22 years old in a car with someone 30 years older, about to live out my most secret fantasy I've had since I could first jack off. We're exchanging pleasantries, but my mind is a haze, and it's obvious we're both nervous and excited about this forbidden little tryst we're about to have.

Skipping the small talk, we get to his house and go to a bedroom. We're standing, and he starts by taking off my t-shirt, and he's caressing my chest, going to the nipples... he pinches and twists both my nipples pretty hard, and it was like a lightning bolt went off. I immediately felt completely submissive, wanting nothing more than to be his little sissyboy. When he started to suck and nibble on my nipples, I moaned and whimpered like a bitch in heat. I barely whispered "I like that, daddy." All I wanted was to submit to this near-stranger more than twice my age, for him to m***** me and use me for his pleasure.

Still standing, he unbuckles my belt and drops my jeans to the floor, still in my boxers. He lays me back on his bed, legs off the edge, gets on his knees and starts to nuzzle my cock and lick and chew at it through my boxers. He pulls my boxers off, and there I am laying completely naked feeling completely exposed and incredibly turned on. He practically attacks my cock... buries his face in balls, sucking them hard. This is nothing like any BJ I've ever had for a girl; this man wants my cock bad. He puts amazing sucking pressure on my cock. It's a very different kind of blow job... where I feel like I'm submitting, being used for his pleasure. I whimper "thank you daddy."

He stands up, and takes off all his clothes, and sits at the edge of the bed. "Lay across my lap, boy" he commands. Feeling like a proper submissive slut, I reply "yes daddy" and lay naked and exposed over his lap. His hands go straight to my muscular ass, kneading the cheeks, spreading me open, rubbing everywhere. Being man-handled like this feels so exhilarating; I'm in that haze of a headspace only really submitting can feel like. I'm ready to be disciplined. "You've been a naughty little slut, haven't you boy?" he says in a commanding tone. "Yes sir, I'm sorry sir" comes my meek reply. "Hands behind your back" he orders. I put my hands behind my back, with one hand he holds both wrists together, pinned to my lower back.

Smack comes the first spank. No building up to it, the first strike is hard. "I'm going to teach you to be a good boy" he taunts. "Thank you daddy" I whimper, just loving the dirty talk. The spanks and verbal abuse keep coming, and hard. It's almost too painful to stand, but I'm loving it in the way only a sub can. Finally the spanks stop briefly, he resumes rubbing and caressing my now very red ass. He spreads my cheeks, I've never felt so helpless and exposed. His finger starts gently rubbing at my hole, and I moan like a whore. "Thank you, daddy." "Good boy" he replies. He spits on my ass, and starts to penetrate my hole. Not rough or aggressive, but strong; it's obvious he's in control.

Then the spanking resumes. This goes on, alternate between spanking and fingering my hole. I'm incredibly turned on by this point, every nerve ending wanting nothing more than to feel him in my ass.

"I'm going to fuck you now, boy" he says to me in a commanding tone. "Yes daddy, please fuck me" is my reply. I'm nervous and scared, but all I know is how badly I want to submit to him, and I know I want to be fucked. He positions me on my hands and knees at the edge of the bed, puts some KY on his fingers, and starts really lubing me and opening me up. His other hand is between my legs, groping my cock and balls from behind. (I didn't even know at the time, but I realized being touched like that is a major turn-on for me.) He's verbal, and I'm loving it. Variations on him telling me what a good boy I am, and me saying thank you daddy.

At this point I'm begging for it, my face is in the mattress, ass in the air, daddy's fingers in my hole. "Please fuck me daddy" I beg. He rolls on a condom and lubes up his cock. My asshole is twitching, eager, and a little scared. He lines up his cock, and gradually slides into me. I can feel my hole being stretched open by the head of his cock, and a moan escapes my lips. "Good boy, take daddy's cock" he says. It hurts, it's big, but I want it badly. He eventually gets it all the way in, and starts a slow steady pounding of my now no-longer-virgin ass, all the while telling me what a good boy I'm being.

I'm loving this fuck, it hurts in the best way imaginable being used like this. I know you're supposed to relax, but I can't. My hole is continually twitching and clamping down on his cock. Feeling it inside me, unable to fully close my hole... just incredible. I reach down and start jacking myself and I moan. He immediately grabs my arm and slaps it away, and says "oh no boy, don't you dare cum yet!" and fucks me even harder, slapping my ass. I still get rock hard remembering that. Eventually he starts moaning, and fills the condom with his load.

Exhausted and feeling so well-fucked but still so extremely horny, I collapse back on the bed and start stroking myself. He lies down next to me, grabs my legs and pulls them up, and his mouth finds my nipple and he sucks on it aggressively. His fingers find my well-lubed, well-fucked ass, and he starts fingering me with 2 or 3 fingers. Moaning like a whore with my knees by my ears, and this much older man sucking my nipples while he finger fucks me, I blast cum all over my chest.

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My wife gave me a quick kiss and let me know she had to use the bathroom after travelling. She headed to the bathroom right there on the main floor, giving me time to clean up. I grabbed her bags and rushed upstairs. I dropped them as soon as I entered our room and darted to the bed to straighten up. "Honey," I heard my wife, "where'd you go?" "Brought your bags up for you," I replied. I finished smoothing out the bedspread just as she came in. "Thanks sweetheart," she smiled...

1 year ago
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First Real Hookup

Hey! My name is Chris and I'm 19. I've always hooked up with girls but have always had a feeling in the back of my mind that I would enjoy being sexual with a guy. Never anyone I knew because I would be too weirder out but someone around my age and sexy and random. I'm white and I'm 5'11" with and athletic body. I've always been told I'm very good looking. I have brown hair and eyes and some body hair. I don't shave anything though. My dick isn't too big soft but grows to be around 7 thick...

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4 years ago
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First Time Meeting Daddy

First time meeting daddy Sissy fiction by Meganprincess (An experiment in dialogue) I was so excited that night. Maybe too excited. I was to finally meet and be used by my on-line daddy. I had no idea how it would go but I wanted to capture it. And so, I strategically hid a camera in the living room in the corner by a window. Unfortunately for me, the curtain fell a tad as I walked away. The result? One hour of riveting footage of a beige curtain sash on high def video. The...

2 years ago
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First CL Anon Hookup

I had been fantasizing about meeting up with another guy for sex, and sucking cock for the first time. I'll save the "why" for another story; suffice it to say I had been thinking about it for a while, and had jerked off a fair amount while browsing the m4m personals on Craigslist.One weekday morning for whatever reason I had the day off. I plucked up the courage to respond to an ad posted by a guy in his late 40's who worked from home during the day. One of his ad pictures was a of...

3 years ago
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first online hookup crazy fun

As I log on to my social network of choice, I put down my bottle of cola for a moment to input the password. As the page loads up I taste the sugary drink. In the corner of the screen there is 1 new friend request. ‘Maria’ 20. I remember working with Maria a few years before that, she was about 3 years younger then me but she was pretty open about what she wanted, even when she was 15. I accept, thinking to myself ‘worth a shot now’. A few moments later an IM bubble pops up ‘ hey stranger,...

3 years ago
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first online hookup crazy fun

As I log on to my social network of choice, I put down my bottle of cola for a moment to input the password. As the page loads up I taste the sugary drink. In the corner of the screen there is 1 new friend request. "Maria" 20. I remember working with Maria a few years before that, she was about 3 years younger then me but she was pretty open about what she wanted, even when she was 15. I accept, thinking to myself "worth a shot now".A few moments later an IM bubble pops up " hey stranger, how...

3 years ago
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Daughters First Time With Her Daddy

My daughter girl is lying stark naked on the bed, on her back, with her head facing away from me, her long hair splayed out on the pillow. One hand is between her legs, rapidly rubbing her pussy, and the other hand is squeezing her lovely breasts and pinching her nipples. She has her electronic tablet propped up beside her and it is obvious that she is watching a porn video while she plays. It looks like an older man is playing with a much younger woman. I wonder why I don’t hear sound from...

3 years ago
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Red Nixy Shower time with Daddy

Shower time with Daddy I want to be your Daddy's girl that you love more than anyone else in the world. I want to walk around the house in short cheerleading shorts with a tight small undershirt on with no bra on. I am sitting Indian style on the floor of the living room texting friends on my phone but when you get up and walk by to go to your room I will pull the fabric covering my pretty pink pussy to the side and show daddy a little bit of his naughty girl. I am so excited that my Daddy saw...

2 years ago
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First Online Hookup

Every once in awhile I get horny enough to hop on a male for male hook up site and browse around, luckily for me most of the guys on the website are older so it’s nice jackoff material too. I usually just browse around till I’m horny enough that I’m on the edge of cumming then jack myself off to take care of it. This day was different though. I log in to the website and within about 5 mins, an older man in his 50s messages me asking me how my day was. I was horny as hell that day so I told him...

3 years ago
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A Sissy Fantasy A Day And Night With Daddy

A Sissy Fantasy - A Day And Night With Daddy Daddy's Cocksucking Princess I awoke after falling asleep after last night's escapades, and the first thing I I notice is the chastitiy, it immediately reminds me of what happened last night. I wasnt expecting to be put in chasitity last night, Daddy had hinted at it, but I did not think he was have me in it so soon. I did not really want to have my clitty locked up like that, but I really want to please Daddy, so of...

2 years ago
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Melody8217s Life With Daddy

The morning sun broke through a crack in the curtains, flooding her naked body that lay on the bed. The sunlight hit her back and ass; warming it from the early morning chill. Melody stirred, still half asleep reaching over hoping to find a warm body next to her in bed. She found that there was no one there. She slowly opened her eyes and looked at the clock, it was already a little past nine thirty, she must have not heard the alarm go off. She rolled over on her back, and opened her eyes...

2 years ago
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Hookup Sex With A Gorgeous Lady in Delhi

Hi. This is Aditya again, back from Delhi. I am submitting a story almost five years after my previous submission. Hope you will enjoy it. This real-life incident is from April 2018. I was hanging around and chilling with some friends at Khan Market and having delicious pizza at the Big Chill café. Being Saturday, the group population started dwindling until just me and a friend of mine Sneha were left. We were talking about crushes and best sexual encounters and were completely unaware of the...

3 years ago
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Sex chat hookup with stranger an 8 inch cock

I’ve been active in sex chats before. But I’ve never actually met up with someone…until now. One night I opened my profile to this message: in town for one night, 8 inch cock. I was mesmerized by the pictures of his dick. So I sent him a message last night. We agreed to meet up early next morning. I had a hell of a time getting to sleep, nerves, and excitement just thinking of that huge cock filling me up, my dripping pussy stretched with that manly girth, making me feel like a virgin all over...

3 years ago
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BiCurious Xhamster Hookup With Married Dude

Luke and I had been messaging on Xhamster for about a week and finally decided we were ready to try sucking each other's cocks. He's married and I have a girlfriend. But the memory of how my c***dhood buddy's dick felt in my mouth has been haunting my fantasies lately. I like girls and don't connect with guys in a sexual or emotional way. But, lately I just want to suck a cock and feel it throbbing in my mouth with a load shooting while I stroke it with my tongue. Once I found Luke and found...

2 years ago
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Hookup With Guy I Met Online

Hi guys my name is Ankit Singh and this is my first story in indian sex stories dot net. I often read stories here especially gay male category and enjoy reading it. I have decided to share my first and only sex experience with you guys. I was living with my relatives in Surat and was preparing for my CA exams which soon ended. After the exams I had nothing to do and I started feeling lonely because I didn’t know anyone in Surat and my relatives were not free either. I felt very lonely and...

Gay Male
2 years ago
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one night hookup sharing my wife with her Ex

We met my wife's ex at a recent party and what a night it turned out to be.I knew she had often mentioned there sexual encounters as i loved hearing how he fucked her while she was riding my hard cock making it even harder every time.The party was at a hotel restaurant and being a big night we booked a room for convenience.No sooner had i left the table for a toilet break her ex was all over her at the table on my return. She left for the ladies powder room and i noticed he followed her shortly...

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