Crossdressed For A Spanking free porn video

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I was younger around mid 20's I was starting to feel the need to be spanked. So I put ad on a free site and waited for responses. I got several but only one that stood out. Most of the ones that responded wanted to know why I wanted to be spanked or what I did to deserve the spanking and would not take that I just wanted one as I enjoy getting spanked as a response so I knew those were not the ones for me. The one that stood out just wanted a couple more pics of me and then we arranged a time to meet at his place. I wore my panties and pantyhose under my normal clothes and changed when I got there. I walked out of the bathroom when I was done changing and he had me kneel in front of his sofa where he bound my wrists with rope that was tied behind the sofa. He then took out a riding crop and started to spank me with that until he got my ass bare. Then he spanked me some more with the crop then started with a paddle (was a ping pong paddle but it worked) After switching back and forth between the two he asked if I had a preference and I told him the paddle and he can spank me a little harder with it. He then gave me more spankings non stop until I told him that I had enough and had to get going. I went back to the bathroom and changed (in which now I wished I would have asked him if he had any problems with me leaving dressed). When I got out of the bathroom it was then that I realized that he had been naked while spanking me and I saw his cock hanging there. That was the other regret was that I had not sucked that cock. I knew he spanked me a lot and noticed that my ass was a dark red when I was changing but did not realize how many days that my ass would be sore after that spanking.

I had a female boss at where I worked at that time that called me into her office a couple days after I had the spanking and she told me to sit and I told her I would prefer to stand but she insisted on me sitting. Now keep in mind the boss and I were friends but did not know that I liked getting spanked. So after she insisted that I sit I slowly sat down and when I got seated I must have grimaced in pain because she asked if I was ok. I told her yes but she said it was obvious that I was not ok. I told her no all is fine but she said no that it looked like it was painful for me to sit and wanted to know why. So I told her that I had been spanked a couple days prior and she asked what I did to deserve a hard spanking that left me unable to sit for a couple days. The look on her face when I said nothing that I had just wanted to get spanked was great. She understood and we went on with why she called me into her office. She was also someone I wish I could have had spank me as I know she would give a nice hard spanking as she was Sicilian.

I am now in my mid 40s and have been spanked a dozen times and still feel the urge to get spanked. Maybe sometime after this Covid thing is over I will be able to get someone to spank me again. Whether I am cross dressed or not I just want to get spanked with a belt and a paddle and hard too with both.

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01.11.2021
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My apologies to whoever was waiting for me to continue about Mr. Walker. I mentioned near the end of my last story that I was humping the bed shortly after my friends dad left my bottom sizzling. I didn't understand why that spanking had evoked erotic feelings in me, all I knew was that the feelings were very intense and confusing. I won't bore you with details I can't remember clearly. I do know I had no one to talk to about what was going on in my head. Was I gay because I was bared and...

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Growing up I’ve always had an interest in spankings. I’m sure it all started from being spanked as a k**. I’m a happily married 52 year old white male. To give you a better picture of me, I’m 6ft, 195 lbs, short red hair, smooth body, 5 1/2 inch cut cock, decent shape.My curiosity to receive a spanking as an adult grew more and more. I was wanting to be spanked by an older man. Not a severe spanking, but one that would leave my ass red. And to have a feeling of shame, embarrassment, guilt and...

Her very first Sensual Spanking

Simply answering an advert leads to a whole new world of pleasure ! Sue sat nervously in her lounge, feeling excited yet scared as she waited for him to arrive. Over and over in her mind, she wondered if she was doing the right thing This was not the first time she asked herself this question. That morning as she answered David's text messages, following his instructions carefully, she wondered what had come over her. Each attempt to understand herself only made her more nervous and anxious....

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