I Didn't Expect His Wife & Sister

One night when I was 18 I got caught nude below the waist by Mr. Harris in his backyard. Given the option of being turned over to the police or being spanked I opted for the spanking. What I got was more than a spanking and it triggered my interest in play with dominant men.

Up until my late 20's from time to time I engaged in some kinky play, mainly focused on being spanked. There was a scary encounter with a black gangster and a little time spent as a "Boy Toy" for a motorcycle club. It was fun but then my activities went dormant and vanilla for 30 years but thanks to Mr. Harris my love of being spanked never waned.

Over those years I continued to fantasize about being spanked by a man but didn't know how to arrange it. Then, I discovered Craigslist personal ads and decided to give it a try and ran an ad saying I wanted to be spanked by a dominant male.

A man responded to my CL ad and told me that he was a retired high school principal and while he had paddled many male students 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 misbehaviors that warranted Cpl. 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 not only what I had done wrong but also what factors influenced my interest in being spanked by a male. All of this sound perfect to me. I mentioned Mr. Harris but didn't go into details.

It was also a bit intimidating but it was 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 was very excited and also very nervous.

When I arrived at his house I was shocked when an attractive lady in her 60s answered the door. I thought I went to the wrong address and was quite stunned when she said, "You must be Randy and here for your spanking" and then 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.

Continuing she added "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 10 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 tell what I had done wrong and why I wanted to being spanked by a man. As requested I provided them with a detailed account of why I was in Mr. Harris' yard with no pants on and details about the spanking I received.

I felt as if I had been transported back to the time that I stood before Mr. Harris, nude below the waist. As they probed for details I felt my cock stiffen which was embarrassing. And it was a truly humbling experience to have to confess to my misbehaviors that would warrant corporal punishment. Overall it was like standing before a tribunal, devoid of any humor, banter or small talk. They jointly concluded punishment was in order.

Tom escorted me over to a wooden chair in the middle of his living and ordered me get get across his knee. I was only 5'6" and 140 pounds.Tom was a big muscular guy, about 6'3" and well over 250 pounds, He had no problem pinning me down. I was feeling like a naughty little boy waiting to get spanked.

To insure that I remained in place Tom's wife bound my hands together to the chairs bottom rung. My legs were free to kick, but with Tom's arm pinning me down there would be no escape. I found this prospect very erotic and exciting.

This impression was made even more intense because Tom gave me a long stern lecture about my misbehavior and how inappropriate it was for me to be running around with no pants on.

This went on for at least 15 minutes during which time my erection was readily visible to his wife and sister, both of whom commented on my state of arousal.

Picking up on their cue Tom slipped his hand between my legs and proceeded to fondle my erect cock while asking me if this is what Mr. Harris had done. The fondling and the required confirmation enhanced my arousal and my humiliation at the same time.

The spanking itself was quite prolonged and much more painful and severe than I had anticipated.

He started with his hand. He was a powerful man. The spanking was administered slowly and methodically with no gradual warm up. I loved being helpless and feeling the sting and burn on my butt. This was what I had fantasized about for years.

Then I gradually became aware that the pain was building up rapidly. I realized I was beginning to squirm around and my quiet moans of pleasure were replaced with audible grunts of pain.

The arousal I experienced while over his lap had waned as well. This was for real and not the sensual spanking I expected.

I was transported back to not only to my time with Mr. Harris but even further back to the sense of helplessness that accompanies childhood spankings. When I first went over Tom's lap I could hardly wait for the spanking to start. Now all I wanted was for it to stop but Tom showed no sign of tiring. It went on and on.

I was overwhelmed and shaking with pain, my butt was on fire. I decided I had enough, " Stop, please I can't take any more." I struggled to get up but being tied down i obviously couldn't. I was as helpless as a little boy over Daddy's knee.

I was relieved when Tom stopped then I heard him say, " I made it clear and you agreed that I was in charge. I'll decide when you've had enough, but my hand is beginning to hurt." I thought " Thank God, his hand and my buut gave out at the same time."

Tom was stroking my butt, a pleasant change but I was still pinned down. Then Addressing his wife, "Bring me my paddle."

She came over with a small wooden paddle, perfect for OTK use. No sooner than I exclaimed, " No please" it came down with a loud pop. My next words were "Oh, my God' followed by a screech, " Ah ah ah". Tom's slow and methodical pace changed. The paddle was landing every couple of seconds.

On my way to Tom's house I would have never dreamed that I would end up whimpering, pleading, teary eyed with snot coming out of my nose like some errant little boy.

My whole world was centered on the pain and burning of my bare butt. At some point I realized I was verbalizing those futile pleas of childhood, "Please no more", "Please no more spanking" to no avail.

My words transformed into sobs and then to tears, gasps and snot running out of my nose. I finally quite struggling and laid limply across his lap sobbing as he turned my butt the color he desired. Finally it was over.

I heard him say, "Okay ladies your turn ". Through teary eyes I saw that his wife had donned latex gloves. His wife took out a dildo with a wooden handle and had a tube of lube in her other hand.

His sister had moved a footstool over in front of the chair. I realized what was going to happen. I struggled to get up but was still tied in place. I kept saying, "No not that!" This was never mentioned in our emails.

Tom responded by saying, "No arguments" followed this by two very hard swats with the paddle which landed on my unbearably tender and sore butt causing me to scream in pain while at the same time assuring my compliance.

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 worked the dildo into me,working it in and out. All this time Tom was rubbing my butt.

The sensation on my prostate was overwhelming causing me to become erect again. That's when his sister sat down on the footstool and began to massage the head of my cock. Every time I got close she would back off.

Eventually I was let up and Tom's sister made me bend over the couch and inserted a large butt plug and used her nails on my butt and continued to tease and edge me leaving me begging to ejaculate.

I can't really adequately describe what I was experiencing. It was a combination of feelings of helplessness, humiliation, and a level of sexual arousal I had never experienced before. I could barely talk. I wanted to cum so badly but instead I was being slowly edged and milked. I lost track of time. I heard the sister remark about how much I was dripping.

Eventually it stopped and I was allowed to stand up. I was weak and dizzy and still rock hard. That is when I saw Tom had his cock out of his pants. He said, "I'll make you cum. If you want to bend back over the couch."

By that time I wanted it and willingly complied. Much to the delight of the ladies Tom and I both came about the same time. I was emotionally and physically spent. My butt was incredibly sore but I came to the realization that I loved every minute of the session.

The ladies cleaned me up. Still pants off I sat between them on the couch while I joined the three of them sharing bottles of very good red wine over several hours. I ended up sharing some of the experiences I had in my 20s. they were fascinated.

They asked 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 a head while Tom and his wife watched.

Tom confessed that the three of them had been looking at Craigslist and thinking about a mild BDSM session. When they saw my CL ad, photos and read my emails they decided they wanted to do it and made plans how it would go.

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. I understood but was disappointed,. Hell by this time I wanted to move in with them.

After this I arranged numerous spanking sessions through Craigslist and while enjoyable none of them ever approached my first CL experience. How could they?