First Craigslist Spanking - More Than I Ever Expected. free porn video

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When I was seventeen, I came up with the less than brilliant idea that it would be fun to walk around the neighborhood at night with no pants on. It was fun because I would experience spontaneous orgasms.  One day my luck ran out. I was caught by Mr. Harris, who gave me the choice of a spanking or being turned over to the police.  I choose spanking and it left a lasting impression.

For years, I fantasized being spanked by a man again but didn't know how to arrange it.  Then about twenty years ago, I discovered Craigslist Personal Ads. I ran an ad saying I wanted to be spanked by a dominant male.  My first Craigslist arranged spanking was, without a doubt, my most memorable.

The man who responded to my CL ad told me that he was a retired high school principal.  He had paddled many male students but he always wished he could have administered an old-fashioned OTK bare bottom spanking.  This interested me greatly.  His conditions were that it would be a real punishment spanking, for actual misbehavior that warranted corporal punishment and, that he would be totally in control.

As with his students, there would be no safe word.  He would decide the nature, duration and intensity of the punishment.  He also told me that prior to the spanking we would have a lengthy discussion about my misbehavior why I wanted to be spanked by a male. This was intimidating but at the same time was in line with what I wanted, so I agreed to his terms.

I was to be at his home on Saturday afternoon,  On my trip to his house I had misgivings about what I was getting into but was determined to see it through.  When I arrived at his house I was shocked when an attractive lady in her sixties answered the door.  I said I must have gotten the wrong address.  I was stunned when she said, "You must be Randy and here for your spanking."  She invited me in.  I was even more stunned when I encountered another lady who was introduced to me as her sister-in-law.

She said, "Tom is upstairs on a phone call and he will be down shortly.  He said you should to take off your pants stand over by the fireplace with your hands on top of your head."  Having never been in a situation like this before I was very uncomfortable and embarrassed but then decided I was here, so I might as well go along. I ended up standing there for about ten minutes facing them, bare below the waist, while they sat on the couch having coffee not saying a single word to me.

When Tom finally came down he sat on the couch with them and made me give a detailed account of my misbehavior.  Standing in front of them, hands on my head, bare below the waist, confessing was intensely humiliating. Tom, said, "We'll talk about why you want to be spanked by a man a little later." My mind flashed back to the past humiliation when I had to stand before Mr. Harris and explain why I was in his yard with my pants off.

I'm only five-foot-six and one-hundred-and-forty-pounds. Tom was a big muscular guy, at least six-feet-three-inches and well over two-hundred pounds, and had no problem pinning me down firmly over his lap. I was humiliated, feeling naughty, waiting to get spanked. This impression was made even more intense because Tom gave me a long stern lecture about my misbehavior.

Then Tom switched topics and made me explain why I wanted to be spanked by a man.  I told him about being caught by Mr. Harris. He reprimanded me.on how inappropriate it was for me to be exposing myself. He made me give a detailed account of what transpired during Mr. Harris's spanking.  Reliving the past while over Tom's lap caused me to become aroused and erect.  This went on for about fifteen minutes but at the time it seemed emdless.

My erection was readily visible to his wife and sister who remarked on my state of arousal.  Picking up on their cue, Tom slipped his hand between my legs and proceeded to fondle my erect cock. The fondling and the details I was made to relate  enhanced my arousal and humiliation to an almost unbearable level. By this time I just wanted the talking to stop and the spanking to start.

The spanking itself was quite prolonged and much more painful and severe than I had anticipated.  He started with his hand and eventually switched to a short wooden paddle  The spanking was administered slowly, but hard with no gradual warm up. The arousal I experienced while over his lap quickly waned.  This was not going to be a sensual spanking. 

My mind was transported back to my teenage years and the sense of helplessness spankings. My whole world was centered on the pain and burning of my bare butt.  At some point, I realized I was verbalizing those pleas,  "Please no more, I'm sorry, I won't do it again," all to no avail. Not that I wanted it to stop. My words transformed into sobs and then to tears, gasps and snot running out of my nose.  I finally quit struggling and lay limply across his lap sobbing as he turned my butt the color he desired.

When he stopped he pinned my legs down with his right leg and held he in place with his hands. Then he said, "Okay ladies, it's your turn."  I looked over at them and saw his wife had donned latex gloves and was holding a dildo with a wooden handle and a tube of lube. His sister had set a footstool in front of us.  I struggled  to get up but was firmly held in place. He asked me, "Do you want this?"

I felt compelled to answer, "Yes, Sir." His wife spread my battered cheeks, squirted lube and inserted her gloved fingers in my anus causing me to shudder and moan.  After loosing me up she then slowly inserted the dildo into me.and began working it in and out. The sensation on my prostate was overwhelming, causing me to become erect.

That's when his sister sat down on the footstool and began to massage the head of my cock.  I can't really adequately describe what I was experiencing. It was a combination of feelings of helplessness, humilation, and a level of sexual arousal I had never experieced before.  I couldnt talk only moan. I wanted to cum and realized I was being edged and milked.  I lost track of time. I heard the his sister remark about how much I was dripping.  Eventually it stopped and I was allowed to stand up.  I was weak and dizzy but still rock hard and wanted desparately to cum.

I saw Tom had his cock out of his pants and had put on a condom. He said, "I'll make you cum. If you want to do this bend over the chair." By that time I wanted it and much to the delight of the ladies, Tom and I both came at the same time. I was emotionally and physically spent.  My butt was reallly sore but I came to the embarrassing realization that I loved every minute of the session.

The ladies cleaned me up.  Still with my pants off, I sat between them on the couch while we shared a bottle of very good red wine. The three of them  asked me  many questions about my impressions of the session and told me how much they enjoyed themselves.  All this discussion caused me to become erect again and session ended with his sister giving me head while Tom and his wife watched.

I asked them if we could get together again and was told this was a one time only situation because they didn't want to risk emotional complications.  After this I arranged numerous spanking sessions through Craigslist, and while often enjoyable, none ever approached my first CL experience.

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It was a pure chance, on a nice day I had decided to go for a pint at my local at the edge of town. She must have pulled into the car park just as I went in the main doors. I wasn’t really taking much notice. The place was practically empty. It was only after my first long pull of my chilled lager that I saw her as she sat down. I don’t think it’s her local, but I’d seen her in here many times before, because you would notice her, an attractive woman with a blonde bob of hair, medium height...

1 year ago
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Lisas Craigslist meeting reposted

It was a pure chance, on a nice day I had decided to go for a pint at my local at the edge of town. She must have pulled into the car park just as I went in the main doors. I wasn’t really taking much notice. The place was practically empty. It was only after my first long pull of my chilled lager that I saw her as she sat down. I don’t think it’s her local, but I’d seen her in here many times before, because you would notice her, an attractive woman with a blonde bob of hair, medium height...

1 year ago
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The Craigslist Ad

The ad on craigslist had been in the women seeking women section. It read, "looking for a gorgeous, selfish, slut who will let me camp between her legs for hours on end", Rene didn't really think of herself as selfish, but she wanted to know what exactly the woman on the other end was really offering. She considered responding immediately, but was nervous about the whole craigslist thing. She searched the rest of the ads for a little while, but kept coming back to the offer that seemed almost...

Lesbian
1 year ago
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Craigslist ad 2

This story is my second memorable experience from craigslist. I wasn't horny this time, and I wasn't even looking for something like that in the beginning. In the beginning, I… This story is my second memorable experience from craigslist. I wasn't horny this time, and I wasn't even looking for something like that in the beginning. In the beginning, I was reading my messages about who need my service for a cameraman. In the past month, I took pictures for weddings ,families, engagement...

Dominatrix
1 year ago
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first time hooking up on craigslist

I was 24 at the time. 5’8 tall 190lbs and very hairy. My dick is just under 7 inches and a nice size cut and usually trimmed hair. Not much of an ass honestly and not girly in any way. But I Loved getting fucked like a whore. I have mostly been attracted to women in my life but have had the occasional experimentation with boys growing up which I may post here later if I feel like it. Here is my story. My mom called me on the phone during the week one day and asked if I would be able to...

2 years ago
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Vampire Ethans Story About Ethan Part 1

Let me tell you a little about myself if you don't know. I'm a Vampire of about 600 years of age. Vampires are actually a type of sorcerer initiated into the mystical art of bloodsucking to fuel powerful spells that keep us young, healthy, strong, powerful, and full of a variety of magickal abilities. We can sustain our powers with just a few gulps of blood per week, so we need never kill anyone. We have the power to control people's minds to various degrees. I was gifted in that skill and...

1 year ago
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The Spanking Stories 2 Memento Morey

Too many ironies, thought Susan, drunkenly. Too damn many ironies for one day.She reached for the bottle on her desk, but her hand went where the bottle wasn’t and only succeeded in knocking it into the wastebasket.Hell with it.She folded her arms on the desk and let her head fall heavily onto them as she began to weep again. Too damn many ironies for one life…First of all, the name: Susan B. Anthony. Major Susan B. Anthony, United States Army: combat-trained daughter of Quaker parents who were...

Spanking
2 years ago
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The Spanking Stories 2 Memento Morey

The Spanking Stories - #2: Memento MoreyBy Zen MackieToo many ironies, thought Susan, drunkenly.  Too damn many ironies for one day.She reached for the bottle on her desk, but her hand went where the bottle wasn’t and only succeeded in knocking it into the wastebasket.  Hell with it.  She folded her arms on the desk and let her head fall heavily onto them as she began to weep again.  Too damn many ironies for one life?First of all, the name: Susan B. Anthony.  Major Susan B. Anthony, United...

1 year ago
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Craigslist Chronicles Ch 05 SUV

A few weeks had passed from my night with Alex. God was that a night to remember. Fuck did he had the stamina of a God, ridiculous. Here I was, sitting back in the break room, horny as I'll get out. I was ready for some more fun. Looking through some of the craigslist ads, I came across a few people that wanted to hook up in a car. That could be fun, I thought to myself. One ad really caught my eye; it was a young black dude wanting to fuck. In his ad, he said he wouldn't be available...

3 years ago
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Craigslist Chronicles Ch 06 Thomas

While at work, my horniness returned. God was I ready to be fucked again. It hit me hard. I needed to be used. Stumbling through the m4m section of craigslist, I added "dom" & "dominate" to my search. I wanted someone more dominate and rough around the edges. The thought of having someone tell me what to do turned me on. Hard dom top for slave btm - 22 Horny as fuck. My regular sub has moved away... Looking for a replacement. Big load saved up. Late night ++++. I'm 180lbs, 6', fit,...

2 years ago
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Craigslist Chronicles Ch 07 Steven

This weekend was pretty fun; it was my 21st birthday. I took a few days off to relax and hang with friends. To celebrate the actual day, a few buddies of mine met up at a bar to drink and play some pool. Upon arriving, a friend of mine took it upon himself to announce to everyone that it was my 21st birthday. God, I don't like attention on me. We got our first round of drinks and the bartender, who's pretty damn cute I must say, tossed us the keys to the pool table so we could play some...

2 years ago
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My Craigslist Gangbang1

Over time I started to seek out porn of some of the things they were describing and started to get curious about some of the more extreme things. I found myself watching gangbangs and staring at so many hard cocks and wondering how she felt surrounded by them. I found myself searching other sites for dirty old men and just seeing what they would say they wanted to do to me. That’s when I met Chris on craigslist. He wasn’t like the others, as he could form a complete sentence and I didn’t...

1 year ago
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Breeding Beauty Chp2 Craigslist BBC Bull

Actually I would let her suck my cock and lick my balls then I'd lick her cunt and fuck her. After she orgasm several times she would pass out like a zombie. I'd hold off cumming so that I'd be hard for later... Her ass started off super tight and needed much foreplay...but after months of anal abuse from my cock and my hand she was as loose as a two bit whore.. I loved the feeling of her inner ass ring gripping my cock....looking at her sleeping face and telling her what a cock whore...

3 years ago
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Answering My Professors Personal Craigslist Ad Charlies Adventures 2

Introduction: This is a story about Charlies experience with her favorite professor. This is a continuation of Charlies life. I will be posting her adventures in a non-chronological order, just as they come to me. But Im really wanting to go a bit further with this story, and maybe make it into several parts. As you finish the story, youll realize how this can become a series within my Charlie series. Please comment about things youd love for Charlie and her professor to do, or any other ideas....

3 years ago
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Craigslist Hook Up

The revolution of there being a home computer in everybody's home, and the advent of the dial-up era of the internet, started a whole new sexual revolution. No longer were men and women forced to go out to bars or parties and hope to get lucky. The days of having to put a twenty-word "Personal Ad" in the back of some weekly publication were long gone. The firestorm of American On-Line, coming into homes and the creation of chat rooms started a whole new sexual revolution of the late 1990's. So...

Bisexual
1 year ago
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Craigslist Slut

I was about to turn 18 when all of sudden I hit this massive dry spell. I mean I was on my way to being a Don Juan and it just stopped, no pussy for miles. What was a man to do. This happened back when Craigslist still had the ads for sex and my friend suggested that I check those out as a way to get my dick wet. "Once you get laid you will be back where you want to be." he claimed. "I do it all the time, there are plenty of people on there looking for threesomes and foursomes or wanting to get...

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