Last night was the masturbation competition between Henry and Barry. We decided to have dinner at our house. When Carol and Henry arrived it was clear that Carol had dressed for the occasion. She was wearing a very snug short dress that left nothing to the imagination about her shapely derrière. I could also tell that she was wearing a garter belt and stockings underneath it. I also dressed in what I thought would be appropriate to administer a disciplinary hairbrush spanking to Barry (since I expected him to lose, I thought I would dress in a way that he enjoys when being spanked). I was wearing a snug black pencil skirt and a fitted white blouse. I was also wearing my sexiest white bra that reveals significant cleavage along with a garter belt and stockings. It is Barry’s favorite outfit
We enjoyed a relaxing informal dinner, after which we retired to the family room and lit a fire in the fireplace. Carol said that she was sure both men were wondering why they had been allowed to not wear a chastity device tonight (Carol and I had agreed on that, as well as telling them only that we were planning a special surprise activity for them after dinner … and that they would not need their cages for it). After we settled down by the fire, Carol then explained that we have planned a friendly competition between the men. She relayed the story of Henry telling her about having participated in ‘Circle Jerks’ while in college. I could see Barry’s eyes get wide and I was sure that he was thinking “No way do I want any part of this idea”. However, he kept quiet and let Carol continue. She explained that she and I would enjoy watching them masturbate; and she added that we had decided upon a way to make it interesting and fun. She explained that the goal would be to be the first one to climax, and that the winner would earn the right to turn Carol over his knee for a friendly bare-bottomed hand spanking. Much to my surprise, Barry was the first to say “I’m in”. Carol stopped him from saying anything else by saying, “Wait, there is more”. She then explained that the loser would stop masturbating as soon as the winner had been declared; and would then go over Susan’s lap for a bare-bottomed hairbrush spanking. Barry piped up again with “I’m still in”. It was clear that he was thoroughly motivated by the possibility of getting to spank Carol. I have to admit that I wasn’t pleased by that reaction and silently planned to make him a pay a special price for it with the hairbrush.
Henry was not so quick to accept the challenge, which concerned me a little bit. I was sure that Carol must have mentioned Barry’s ED issues to him at some point. However, he eventually agreed to be part of the competition.
Carol then provided the following ground rules:
· Each male will strip and be naked
· Each male can use the lubricant of his choice
· Each male will be given a small wine glass into which he will ejaculate
· Each male must be completely flacid when the competition begins and can begin when Carol announces that the competition has started
· Neither male is allowed to use any form of pornography or any physical device while masturbating (just his mind and his hand)
· The winner is the first one to expel semen from his penis into his wine glass
· The loser must stop as soon as the winner is declared
· The winner must then drink his semen from the wine glass
· The winner will be permitted to turn Carol over his knee and spank her bare bottom with his hand. Spanking is not to be so hard as to cause Carol significant pain. If she says the word “yellow”, the spanker must reduce the intensity of the spanking. If he does not, Carol can say the word “red”, which will signal the end of the spanking.
· The loser will then receive a disciplinary hair brush spanking from Susan on his bare bottom. This length and severity of this spanking will be determined solely by Susan. The loser must endure whatever she chooses to dish out.
After Barry and Henry agreed to the above rules, Carol and I seated ourselves comfortably on the sofa and Carol directed them to remove all of their clothing. I was surprised to see that Henry was now wearing panties. As they became visible, I nudged Carol and smiled approvingly. She smiled back. I whispered to her that I will be anxious to learn more.
The Competition Begins
Once they were naked, we had the men position themselves in front of us. Then Carol stood up. Turning her bottom towards them she placed one hand on it and reminded them that the winner would get to spank her. I then held up a heavy wooden hairbrush and reminded them that the loser would get to experience a heavy dose of it. Carol then said “Gentleman, you may start to masturbate. May the best man win.”
It was quite interesting and somewhat amusing to watch the two men start to masturbate. I must admit that I hadn’t fully shared Carol’s fascination and desire to watch them masturbate. However, this quickly became interesting. Requiring them both to be flacid at the start was not an issue. It was apparent that each of them was embarrassed by having to strip in front of each other and Carol and me. As they began, I could tell that each was trying to mentally overcome that embarrassment and to achieve arousal. It was also clear that each was also keeping an eye on the other one. Henry achieved an erection first, which was no surprise. What was a surprise was that he didn’t appear to be very ambitious in his attempt to masturbate once he was erect. It took Barry a few more minutes to get hard. Once he did, he started to work vigorously to bring himself to a climax. Henry then began to work harder, but not as hard as Barry. Carol and I both looked at each other and were quite puzzled.
We Have a Winner
After a number of minutes, Barry climaxed into his wine glass. Henry wasn’t even close and didn’t seem to be trying very hard. Carol and I looked at each other … and each quietly voiced, Henry didn’t try to win! I recovered more quickly than Carol and directed Barry to drink his output. I added, “After all, that is our house rule; whenever you get to cum you have to consume it”. I immediately saw Henry’s look of surprise and Barry’s look of embarrassment. Apparently, that was one secret that Carol had not shared with Henry.
As Barry performed his requirement to drink his semen, I announced, “I think it’s time for dessert”. I needed some time to prepare myself for what was to follow. I did not expect to have to watch Barry spank my sister. And, I did not expect to have to provide a disciplinary spanking to Henry. While Carol and I were alone in the kitchen preparing dessert, I asked her if she knew what was going on with Henry. Why didn’t he even try to win? She didn’t know either. I asked her if I should try to sort it out when I gave him the disciplinary spanking. She agreed that I should.
Carol Gets Spanked
After having dessert by the fire, I brought a dining room chair into the room and placed it facing the sofa, about four feet in front of it. I announced that I thought the winner should go first, so Barry took his place on the chair and directed Carol to come stand by his side. As she got up to join him, Henry joined me on the sofa and I reminded Barry of the rules that were established about spanking Carol. I also told him that he had better follow them completely or he would find himself getting a disciplinary spanking along with Henry.
I could tell that Barry was enjoying this moment immensely. He guided Carol into a position over his lap, using his right hand to grasp her bottom as he did so. He then took his time shifting her a bit to get her into a comfortable position for him to spank. I noticed that Carol seemed to intentionally arch her back a bit, to elevate her bottom, which didn’t please me very much. It only served to accentuate her already shapely behind. Barry then asked Carol and me if it was OK if he began the spanking over her dress instead of starting out immediately on her bare bottom. We each agreed. I figured it was that much less time that he would have to observe and touch her bare bottom.
Barry then asked Carol if she was ready for him to begin. When she applied affirmatively, he told her that he understood that she had been a very naughty girl, and asked her if she knew what happens to ‘very’ naughty girls vs. just naughty girls. When she said that she didn’t, he then advised her that naughty girls get spanked, but ‘very’ naughty girls get spanked on their bare bottom. He further explained that he was going to start spanking her on her dress, but since she had been ‘very’ naughty, he was going to eventually bare her bottom before he was done. During this entire conversation I couldn’t help but focus on the fact that Barry’s right hand was cupped around her right bottom cheek. He then began to spank her: slowly and methodically over her dress. After each spank, he allowed his hand to remain on her bottom for a second or two. I’m embarrassed to admit that I was getting very jealous and upset. I had to force myself not to make a comment to remind him to behave himself. I also had trouble watching what was happening. I wanted to watch Barry’s face to try to determine how much sexual pleasure he was deriving. I also wanted to watch his right hand to see what he was doing. You can probably guess that I was a mess! However, I managed to keep myself together.
After several minutes of rhythmic spanking, Barry eventually announced to Carol that it was time to raise her dress and asked her if that was OK. I had to admit that he was being the perfect gentleman that I know him to be. Carol replied affirmatively. Barry then slowly slid her dress up above her waist to reveal, what I am sure, she had worn to please Henry. As he did so, he revealed stocking tops attached to a silver grey garter belt, and a bottom encased in sheer pink panties. The panties had ridden up a bit to expose more cheek than they were designed to. Barry carefully pulled them back into place to cover more of her bottom. Again, a perfect gentleman. I was focused on watching what was happening, but by the sound I heard emitted next to me by Henry, I was aware that it took his breath away.
Resting his right hand on her bottom (I couldn’t stop my focus on how much his hand was in constant touch with her bottom) Barry immediately commented that her panties weren’t going to offer her much protection, but they would eventually also be removed. (My mind was in overdrive at this point. I couldn’t help but feel that Barry was creating a sexual experience for himself … and I didn’t like it.)
Barry then resumed the methodical spanking as before, usually alternating from cheek to cheek, but sometimes administering five or more spanks in a row to the same area.
After another period of time, Barry paused again and advised Carol that it was time to lower her panties and receive the spanking that ‘very’ naughty girls deserve. He asked her if she objected. When she said that she did not, he slipped his finger tips into the waist band of the panties. As he did so, Carol raised her bottom slightly to allow him to lower them. Barry slowly lowered them to her knees. I couldn’t help but notice that Carol spread her legs slightly after the panties were lowered. I could tell, even from where I was sitting, that she was providing Barry with a delightful view. It also appeared that Carol was cleanly shaved in that exposed region.
Resting his hand on her bottom again, Barry announced to Carol that this is when a real spanking takes place. He then resumed spanking, not any harder than before, but at an increased pace. I could tell that Carol was feeling this more. Barry also seemed to focus more on her lower bottom than he did before, which is much more tender. I could see Carol’s face and it was clear that she was working to handle the faster spanking. At one point Barry picked up the pace a little more, which caused Carol to utter “yellow”. Barry immediately paused and asked her if she was OK. When she replied affirmatively, he resumed the spanking at a similar pace, but with less force. After another minute of causing Carol to squirm, he announced to her that he was going to administer ten hard spanks rather rapidly, which would be the end of her spanking. He asked if she thought she could take that. Hearing a ‘yes’, he then delivered the ten as promised. Carol was very actively squirming and groaning after the first five, but she took them all. When he finished, he patted her bottom again and told her it was a lovely shade of pink, which should nicely match her panties.
Barry then helped her to her feet. She immediately reached down to pull up her panties. Since her back was facing me, I could see that Barry was correct about the shade of pink. I also glanced over at Barry’s eyes and it was very clear at what part of Carol’s anatomy he was watching. His eyes were fixed on her crotch.
At this point, Barry thanked Carol for allowing him to spank her and told her that he thoroughly enjoyed the experience. He added, “I hope you did, as well”. Carol immediately responded that she did; and that it was obvious that he did. She then directed Barry to stand up and show Henry and me his “tent pole”, adding for our benefit that she could tell he was enjoying it by the pressure his erection continually placed on her. Barry hesitated to stand, and she reached out a hand to help him. There was definitely a tent pole in his pants! Carol then jokingly added that it looks like we have discovered a solution for Barry’s ED. She then turned to me and said, “All you need to do is take a short trip over his lap for a sensual spanking … and he’ll be ready to go.”
A Surprise for Barry
Carol then stated that she thought Barry needs to get rid of his erection; and she proposed that he be required to masturbate for us again. She also justified her request by stating that she helped him get that erection, so she should get to say how he relieved it. Barry looked shocked. I was embarrassed, but not surprised, by Barry’s sexual reaction to spanking Carol. Jealousy again reared its ugly head in me. And, feeling a need to punish Barry, I quickly agreed.
We then took a break for a second cup of coffee before proceeding. We also talked briefly about Carol’s spanking and she again thanked Barry for being such a gentleman about how he did it.
Time to Sort Things Out with Henry
I then stood up from the sofa and turned to Henry who was sitting next to me. I grabbed him by his left ear and marched him over to the dining chair, telling him “We have a few things to discuss tonight about your behavior”. I could tell that my abruptness took him by surprise, which was the effect I wanted. As I did this, Carol and Barry moved to the sofa.
Sitting on the chair, I told Henry “The first thing I want to talk with you about concerns why you didn’t seem to try to win the contest earlier tonight. It was obvious to Carol and me that you weren’t even trying.” Henry initially claimed that he had tried but was embarrassed by the entire situation. After being pressed further, he finally admitted that he had decided that he really wanted to experience being spanked by me, so he decided that by losing the contest, he would get what he considered to be the winning prize. Carol piped up and asked what happened to his desire to spank her bottom. Henry, unwisely, remarked that he thought he could talk her into that when they were alone, but getting spanked by me was harder to arrange. Carol’s response was simply, “Don’t be so sure of yourself about either assumption you made”. I commented that it sounds like Henry has made the common mistake of thinking with the wrong head.
Keeping Henry standing by my side while I sat in the chair, I asked him to remove his trousers and to fold them up neatly and put them on the floor. He quickly complied. I couldn’t resist commenting on the fact that he was wearing panties and that he had an erection. I asked him if he was excited about being turned over my knee to be spanked. He indicated that he was. “Well, let’s see how long that lasts”, I remarked.
I then asked him if he has ever received a disciplinary spanking. He replied that he had. When pressed for details, he admitted that he has received them from the dominatrix he used to see before he got serious with Carol. I decided to probe further and asked him if she had ever spanked him to a point where he didn’t feel he could take anymore. He replied that she had, so I asked “And what happened then?” His reply was that he used his ‘yellow’ safe word and she lightened up. I couldn’t resist asking “And you think that constitutes a real disciplinary spanking?”
Henry Learns What to Expect
Not waiting for a response, I went on to explain to Barry what constitutes a true disciplinary spanking… and what he could expect from me in a few minutes. I first explained that he would find himself turned over my knee with his bottom bared. I would begin by using the hairbrush to thoroughly spank every inch of his bottom until it was very red and very sore. I added that the intensity would be very tolerable, and perhaps even enjoyable to him. However, I further explained that it would be a long spanking, and when I was done with that part of his spanking his bottom would be very sore for at least three days; and that the purpose of that was to make sure he thought about his punishment every day for that length of time. I went on to explain that once I felt his bottom was sufficiently tender and sore, the real punishment would begin. I would then spank with greater speed and intensity. He would quickly come to the point where he felt he couldn’t handle anymore. “However”, I added, “It will be different this time. There will be no safe word.” I went on to explain that when I sensed he could not handle any more, I would not ease up. Instead, I would increase the intensity, while making sure I held him firmly in place. He would have no choice but to take it. “That”, I explained, “is when real discipline and real learning starts to happen.”
I then asked Henry if he was ready for that. As he responded in a positive way, I looked again at his penis. It seemed to be harder than before, and I could see that it was visibly twitching. “You seem to be very aroused”, I commented. “Would you like to experience a release from that?” Not surprisingly, Henry said “yes”. Barry immediately said “Don’t do it Henry”. I gave him a look that told him to stay out of it.
A Surprise for Henry
I then turned to Carol and shared with her that it appears to me that Henry is still thinking with the wrong head. I expressed my opinion that I thought we should grant his request and then I should administer an appropriate disciplinary spanking to him. When she agreed, I asked her how she thought we should allow Henry to experience a release of his sexual tension. I was not surprised when she suggested that he should masturbate for us and drink the result just like Barry did.
Henry quickly found himself standing in the middle of the room masturbating, with me holding a wine glass to catch his semen. It took him less than a minute to achieve orgasm and express a significant amount of fluid into the wine glass. “Wow”, I said to Carol. “How long has it been since he’s had a release?” The answer was a little over a week because Carol was trying to make sure he would win the original competition. Henry didn’t appreciate it, but I quickly held the glass above his mouth and forced him to drink his semen.
Henry Receives a Disciplinary Spanking for the First Time
Henry then found himself standing by my side as I sat in the dining room chair. He was naked from the waist down. Using the bristles of the hairbrush to tease his flacid penis, I asked him if he was still excited about receiving the disciplinary spanking I previously described to him. He clearly was not. I then asked him if he knew why I was going to discipline him. I was pleased to hear him say that it was because he made bad decisions, using his dick (his word), instead of his brain. I acknowledged that he was correct and asked him to tell me the bad decisions he made. He correctly mentioned his decision to not try to win the masturbation contest with Barry. However, he didn’t come up with anything else. So, I suggested to him that by the time we were done he would regret the decision to have a sexual release before the punishment.
I then turned Henry over my lap and made him spread his legs to better expose his lower cheeks and lower groove between them. I spent a considerable amount of time methodically spanking his entire bottom and upper thighs with the hairbrush. I made sure I paid attention to the lower slope of his cheeks and the area between them. He actually seemed to enjoy it for a while. However, before long, it was clear that it was no longer enjoyable, but not intolerable. When his bottom was a uniform red color and he seemed to be squirming more, I paused to ask him how his bottom felt. It was clear that he felt it was very sore. I pushed some more and learned that it hurt more than he has ever felt before. I told him that it should and that I expect that it will hurt for several days. I reminded him that this is part of the disciplinary process.
I then told Henry that we were going to move to the next stage of his disciplinary spanking. I used my right leg to clamp over Henry’s left leg. I then asked Henry why he was being disciplined. This time he got it completely correct about the two bad decisions he had made. I reminded him to keep both of those decisions in mind during the next few minutes. I then began to spank him with the hairbrush much more intensely. I still didn’t have to swing hard. I let the hairbrush do the work. However, I increased the frequency of the spanks and often spanked the same spot repeatedly. Henry’s distress level increased significantly. At one point I paused and asked him if we were at the point he had previously used his safe word. Stupidly, he said “no”. So I took his right wrist in my left hand and held it behind his back. I then began to spank at the same frequency, but a bit harder. It was not long before he was frantically trying to get away from me. At this point, I reminded him that this is when things get learned and to think about his bad decisions. I continued to use the hairbrush to punish his already sore bottom. I was very intentional in what I was doing. When I finished, it was all I could do to hold Henry in place as I spanked him.
When I finally stopped, Henry just slumped over my knee. I asked him what he had learned. It took him some time to respond, but I was very pleased to hear that he learned not to think with his ‘dick’ instead of his brain. And, I was surprised to hear him add that he learned what a real disciplinary spanking was all about. I decided not to push it any further than that.
I looked over at Carol and smiled; and she smiled back. I looked at Barry. It was clear that he had been relating to what Henry was experiencing. His face was ashen. He knew what Henry had just experienced and obviously had a lot of empathy.
I apologize for the length of this post. It is much too long, and probably not well written. However, I was anxious to share what happened last night while it was still fresh in my mind. I will also get together with Carol later this afternoon. That will give us a chance to talk about what happened last night. I look forward to learning more about her reaction and sharing mine with her. There is much to talk about J!