James,
Envy of the tales of your spanking adventures has caused me to be proactive in having some of my own. Unfortunately, my wife has expressed no interest whatsoever in participating in such activities on my behalf. However, she has agreed to “look the other way” if I am able to arrange spanking sessions with others who provide this service.
To this end, I recently placed an online ad seeking a senior woman to participate in a confidential relationship that would result in her spanking a married senior man. Miraculously, I wound up chatting with an interested widow who lived right here in my development.
When I felt comfortable with her ability to maintain confidentiality, and her genuine desire to do the spanking deed, I agreed to meet her at her house last Monday. Sarah was widowed about two years ago but during her marriage, she and her husband were devoted practitioners of kink, some of which involved spanking, with most of the sessions involving her being the top.
I presented myself at her door on Monday afternoon. It was one of the nicer homes in the older part of our development with an outdoor foyer(?) enclosed by a wrought iron fence/gate arrangement. When I rang the doorbell, a voice from the intercom/camera system asked me a security question we had agreed upon ahead of time and when I answered correctly, she told me to demonstrate my sincerity to the venture and to achieve entry to her home, I would have to completely disrobe in front of the camera.
As you can imagine, I was extremely leery of this request, not to mention nervous, since, even though I was inside the foyer and there were several trees and shrubs in the front yard, it would be possible to see me if a passerby was really paying attention. But I felt committed to the scenario and figured it was payback for all the tough questions I had asked Sarah during the screening process. So I stripped!
Fortunately, the door was opened after just a few seconds and I was greeted by a very attractive and well-preserved 60-something lady dressed most provocatively in black lace bra, panties, and garter and stockings. Long black velvet gloves and black strap high heels completed her dominatrix look. Wow, I thought. This might turn out to be very interesting!
I noticed she was also sporting a small riding crop when she used it to greet my slowly growing cock. Just a couple of taps on the top of my cock was enough to get my attention as this take-charge gal explained the rules for our session.
“You came here to be spanked and we will certainly get that done… with a few stipulations. I will be your Mistress and you will address me as so. You will obey my every command, without question or hesitation. And you will thank me respectfully as I provide you with the discipline you deserve. Just to insure you get the full benefit of our session, I will require you to wear these leather wrist and ankle restraints that will help keep you still as I put you through your paces.”
With that, she handed me the restraints and instructed me to buckle them securely on my wrists and ankles, to which I quickly complied. She clipped the wrist restraints together behind my back, grabbed me by the cock, and led me down a long hall to what I assumed would be the master bedroom.
I was wrong! This lady had a full-blown play area set up in what would have been a guest bedroom. The room was fairly dark to enhance the ambiance, and the dark red walls were decorated with large pictures and posters of various BDSM activities. I immediately noticed a leather spanking bench and a wooden wall rack upon which were hung a variety of whips, paddles, crops and floggers. There was a small dresser cabinet that I assumed held all sorts of tools of treachery, which I hoped perhaps I might soon experience.
She opened a cabinet drawer and withdrew a leather-wrapped spreader bar with "Y" shaped brackets at each end, which I assumed were to hold someone's ankles in place. I was soon to find out as she knelt behind me and fastened the bar in place by attaching its snapclips to my ankle restraints. OK, now this is getting serious!
At this point, she felt the need to determine my tolerance for the crop as she snapped it numerous times over various parts of my body. None of the strikes were strong enough to leave a mark or even hurt that much; it was obviously play, and we both enjoyed it. Until we got to the genitals! I learned that I could stand a pretty good hit to my cock, but the family jewels were much more sensitive, and even a light strike in the right place sent a shock wave through my entire body and elicited a mighty flinch and a cry out in pain. Thankfully, we moved on.
She moved to the cabinet once again and returned with a small tupperware-like container full of long red clothespins. The container was not exactly in keeping with the BDSM motif but the menacing jaws of the clothespins made up for it. When she placed the first couple of pins on the lower area of my scrotum, I was relieved to learn that, once again, these were not calibrated for severe pain but rather for play and appearance. She attached 4 more in a line along the bottom of my sac, then 3 along the bottom side of my cock. Not super painful, but I was certainly aware of their presence.
All of a sudden, my heart stopped as I heard the sound of the back door opening and closing, and a female voice yelling, "Eleanor, I am home! Sorry, I am late. I got caught in traffic!"
What the fuck?
Then I heard the voice growing closer, "Eleanor, where are you? Did our guest of honor show up on time?"
Eleanor, I thought. What the fuck was going on here? What have I gotten myself into?
When our intruder entered the room and surveyed the scene, it became immediately obvious she was Pissed!
"Eleanor", she cried, "What the fuck are you doing? I have told you over and over again not to start without me. Put away those clothespins and take off my bra and panties, now! Get yourself naked and assume the position while I go get changed. I will deal with you when I return."
Tears were starting to pour from Eleanor's eyes as she replied, "I am sorry, Sarah. I didn't know how long you would be and I thought you would be pleased that I got the scenario started."
Sarah ignored her pleas and turned to me. "Hello, you must be Benjamin. We will refer to you as Mr. B. I am Sarah, and I must offer my sincere apologies. Although it looks like Eleanor is doing a pretty good job of entertaining you in my absence, she knows better than to interfere with my play time. If you wish to continue, I will quickly change into my playclothes and provide you with the session we had discussed earlier, although I will understand completely if you wish to call it off at this point."
I didn't really have to think about it. This was Awesome! Of course, I want to continue.
"Well, I am kinda into it at this point, and it would be a shame to call it off now. Let's do this!” I told her.
"I agree,” she said. “I will be right back."
In the meantime, Eleanor was off in the corner of the room quietly divesting herself of Sarah’s exotic outfit. The tears had subsided, and she was concentrating on neatly rolling down her black mesh stockings so as to be ready for Sarah's return. I was not sure what the relationship was between these two attractive ladies, but at this point, I was most eager to learn more.
Sarah was back in the room in less than five minutes and she was HOT! She wore a similar outfit to Eleanor that was highlighted by an incredibly sexy pair of thigh-high vinyl boots with 4-inch stiletto heels. Another show-stopper was her lack of panties, which showed off her neatly trimmed black landing strip! This gal knew what she was doing when it came to exuding sexuality, and I, for one, was greatly appreciative!
"First things first," she declared. “Eleanor, I told you before I left to assume the position. Now, Do It!"
Eleanor immediately moved to the center of the room, spread her legs about shoulder width apart and placed her hands on her knees, providing a tempting target to anyone else in the room. She seemed to be careful to keep her eyes looking down and not making eye contact with Sarah or me. She, too, was sporting an attractive landing strip and looked a picture of mature sexiness.
"I am really sorry, Sarah," she declared. "Please forgive me. I promise I will never disobey you ever again!"
“Well, Eleanor, you know that I cannot tolerate that sort of behaviour and that to be effective, the punishment must be swiftly administered. Normally, I would not want to dole out your punishment in front of a guest, but in this case, I think it best to make an indelible impression. Please prepare to accept your discipline.”
As Eleanor moved into position right in front of me, Sarah walked to the wall and returned with a large leather paddle. The first paddle strike on Eleanor's bottom made a loud 'Smack' that reverberated throughout the room. Similarly, with strikes two through ten, as Eleanor accepted her punishment quietly and without even flinching.
I had never witnessed a spanking session in person, and I found that the whole scenario was causing a stirring in my groin, resulting in the beginnings of an erection, even through the pain of the clothespins. This session was obviously way more than I had anticipated, and my biggest fear at this point was that eventually it was going to end!
Sarah stopped after the ten strokes, turned to me, and offered me the paddle. "Would you like to do ten?" she asked. "I think it would be only fair." Without waiting for my reply, she walked around behind me, unhooked my wrist restraints from each other, then handed me the paddle. Since I was still attached to the spreader bar, Eleanor was repositioned in front of me so that I could easily perform the task at hand.
My first strike was pretty feeble, even by my standards. The paddle slipped sideways in my grip and instead of a nice loud 'Smack', I got sort of a dull 'Thud'. The first one to the other cheek was much better and I felt the remainder of the strikes were reasonably well done for a rookie amateur.
Both ladies seemed satisfied with my performance and Sarah declared the session ended. She turned to Eleanor and proclaimed, "That's enough for now. We will talk about this again later. Let's not forget we have a guest here who needs our attention."
Sarah turned her attention to me while Eleanor busied herself with getting her sexy outfit back on.
“First of all", she said, "my apologies for being late for our appointment and for the behavior of Eleanor. She knows better, and I will deal with her later to ensure she will never behave like that again! This must have all been very confusing to you."
"Well," I explained, " Not knowing what you looked like, I assumed I was dealing with you from the beginning and of course, wanting to please you, I complied with all Eleanor’s commands. It seemed to be going quite well until you showed up. That was the part that really had me going! I had no idea who was dropping in to our scene!"
"Fortunately, that is all over now! Let's take that spreader bar off and get on with our original objective. I believe you came here for a spanking," she said with a smile.
"Yes, let's do that!" I replied.
When the spreader bar had been removed, Sarah pulled up an armless chair, sat down directly in front of me and began to remove the clothespins one by one. They hurt going on and for the time duration since but I was not prepared for the intense pain provided by the blood coursing back into the areas where blood flow had been restricted by the pinch of the clothespins. “Ow!”
Mistress Sarah took a few minutes to gently massage the affected area, which initially helped to ease the pain but soon began to cause a growing erection once again.
“Unfortunately, we are not here for that,” she proclaimed, and directed me to lie across her lap. Now this is what I came here for!
She spent a minute or two gently rubbing my back, my thighs and my butt. Once or twice, her fingers traced a gentle track up and down my butt crack. This was really getting good! Then, with my legs spread just enough to allow her access, she reached down to caress my balls and stroke my cock. Forget the spanking; this is Heaven!
Realizing it was time to move on, Sarah stopped the gentle stroking and returned to the ministrations of my butt.
"Are you ready to get started?” she asked.
"Yes, Ma'am," I replied.
"You will address me as Mistress or Mistress Sarah, and you will thank me after each stroke," she instructed.
"Yes, Mistress Sarah."
"If it gets a little intense and you need to take a break, you will say, 'Yellow.'"
"Yes, Mistress Sarah."
"And if it gets to be just too much or too painful, you will say the word, 'Red', and I will stop altogether. Understood?"
"Yes, Mistress Sarah."
And with that, I felt a sharp slap on my butt. Not too hard, but enough to remind me why I was there.
"Thank you, Mistress Sarah."
And then a series of successively harder spanks on alternating cheeks, after each one, I replied, "Thank you, Mistress Sarah."
Then, just about the point where I was tempted to ask for a break, the spanking stopped.
"My palm is getting sore; I think it is time we graduated to the bench!". she exclaimed.
I wasn't sure I was ready for "the bench", but I welcomed the opportunity to let my buns cool down a little bit. Sarah led me to the spanking bench as I marveled at its simplicity. There was a series of strategically placed padded shelves, upon which I was to mount facedown and place my chest, forehead, shins and forearms. Once in position, Mistress Sarah buckled the straps on each shelf, which placed me in total immobilization mode with my reddened bottom tantalizingly raised and totally exposed for her pleasure.
"Now we are going to play a little game," she explained as she brought forward a series of spanking implements. " I have here a wooden paddle, a long-handled bath brush, a leather paddle, a riding crop, and a leather flogger. I will be behind you so that you will not be able to see which implement I am using to spank your bottom. I will pick one device and spank you once on each cheek, after which you will have to identify which one I am using with only the tenderness of your buns and the sound of the impact to help you decide. If you are right, I will gently caress your red-hot buns as I was doing before. If you are wrong, I will immediately give you ten more on alternating cheeks. We will repeat the game as I try out some of the different utensils, or until you decide to stop.
“Sounds interesting, Mistress Sara. Let’s give it a try!”
The first two slaps were not particularly loud in comparison to the ministrations to Eleanor’s behind, but the sting sent urgent messages to my nerve center that something or someone was definitely trying to hurt me. Being new to the game and having nothing to compare to, I took a wild guess and offered, “Leather paddle!”
“Good guess,” she replied, “you might be quite good at this!”
The next implement landed with a loud “Smack” and produced a sharp stinging pain much more intense than I had anticipated. “Bath brush,” I guessed.
“Ah, not so lucky this time! I will give you ten more with this wooden paddle, so you will be sure to recognize it if we use it again,” she advised me with a chuckle. I think she was enjoying this!
By the tenth spank, I was about ready to call it quits! Each successive spank stung just a little bit more, and by number ten, I was beginning to wonder if this was such a great idea.
After a well-appreciated short rest where Mistress Sarah gently rubbed the affected area of my now tender bottom, she warned me of the next two to be delivered.
Smack, Smack! More pain, now almost indistinguishable, since a large portion of my buttocks was extremely sore. “Riding crop,” I ventured.
“Wrong again,” she cried. "This game keeps getting better! I am really starting to enjoy this, Mr. B. I hope you are as well.”
“Please call me Ben,” I asked. “I am sure I am not enjoying it as much as you are, but I must admit, when the intensity of pain gets to a certain point, which is extremely painful, it doesn’t seem to get any worse. I think I can probably handle a couple more wrong guesses.”
“Well then, let’s just drop the game facade and give you a few more series of ten with a little break in between. If you can tolerate that without calling “Red,” I think we can call it a day. Quite a respectable achievement for your first session!”
And that’s what we did! I was able to accept that pain threshold, get dressed, and slowly and gingerly walk home.
I rate my first spanking adventure a success and have made arrangements for a second session with Mistress Sarah next week! Thanks to you, I am on the road to becoming a full-fledged Spanko.
Appreciate your guidance,
Your Eager Protégé,
Ben
