I met a newbie to the local BDSM scene we will call "Kitty" and attended a few events together and got acquainted. I shared with her the concept of a CFNM party but I wanted (selfishly) to be the only male present.
We settled on a date about 45 days out so I could get in better shape and have the necessary waxing. We agreed that there would be a mix of kinksters, kink-friendly folks, and a couple of her vanilla friends who would be "open minded" about this experience. We also discussed various activities and food/beverage service. We planned that I would answer the door nude, that I would provide and serve food and drink, and then be the "featured entertainment" lol.
For those activities we agreed on fairly hard impact play (safeword respected), me riding a pegboard (five progressively larger anal dilators mounted on a bench), and then I would be pegged by Kitty with a fairly large strapon that I would have to deep throat first...to all the ladies' satisfaction. And finally, IF IF IF I had performed to everyone's satisfaction, I would be allowed to masturbate to climax and consume the results.
It was a Friday evening. I got off work early so I could shower and have a couple of enemas. After that I stopped at the restaurant and picked up all the food, stopped at the liquor store for the wine, then presented myself at Kitty's house. She and a friend were waiting for me.
They helped me bring in all the food and drink and after everything was set and ready, they produced a plastic garbage bag and proceeded to strip me naked, placing my clothes in the bag. Then they put leather restraints on both wrists and both ankles, and a leather collar with ring around my neck. Shortly the first guest arrived and both smiled and laughed when I answered the door naked. Perhaps they weren't expecting the restraints. The others took it in stride but a few were taken aback as they still weren't sure what to expect even though they had been briefed on the event.
I proceeded to serve food and drink and enjoyed a few pats and pinches. Kitty asked me to pause serving and get erect and then played a little "ring toss". I was rather nervous and needed a little bit of help with the erection so one of her friends gave a quick sensual touch and a kiss on my cheek and that did the trick and then some!
After dinner was over I served cake and coffee. After that they brought me into the main room. One lady with a rather tough and foul disposition then ordered me on all fours and laid into me HARD with belt and cane. I mean HARD. I was close to using my safeword but didn't. Several other of the ladies were invited to try a few strokes.
After the punishment round was over (and I was quite marked), I was placed in a chair and asked a great deal of very probing and personal questions about anything and everything. You might call it the "interview" round but it was more like being in trouble at work and having to speak to HR! Then they all took turns prodding and probing me but I had to draw the line at nipple clamps. I don't know why, but even slight pressure/pinch on my nipples brings major pain. I guess we're all built differently.
Then Kitty decided that it was time for me to ride the pegboard as a lot of the ladies had never seen one before and were curious. Kitty put on gloves and had me get on all fours with my ass up in the air and then she filled me full of lube with a syringe you can buy in sex shops called a "lube shooter". Highly recommend it. Once I was prepped, I got over the pegboard. Ideally it should look something like a sawhorse, but the best we could do is mount the dilators on a wood plank and then set that between two chairs.
I straddled the board and eased myself down on the smallest one to start. It went in surprisingly easily. So far so good...then I moved up to the next one. This one was harder but still not painful. One lady who was experienced in this kind of play said she fully expected me to stop after the first one. And also needless to say my welts and bruises from the belt and cane were on full display and added to the visual spectacle.
I moved on to the third one which required I go a bit more slowly, but it wasn't painful. Another round of applause and a quick kiss on the cheek from one of the ladies. I moved on to the third, and this one hurt a bit but by going slow and moving up and down a couple times, gradually increasing the penetration I managed to get it all the way in. Another cheer.
Kitty asked me if I wanted to try the fourth but that I had nothing to prove. I moved on to the fourth one. This one did hurt and I went quite slowly. After about two full minutes, I got it in! This seriously impressed the ladies and I got high fives and careful hugs all around, since it was still in.
I decided that was enough and passed on the fifth, which Kitty felt was wise. Then came time for the strapon. Funny, you might think it was anti-climactic after the pegboard but Kitty wisely chose to really make a show of it. She remained fully clothed and put the harness and dildo on over her jeans. Then she worked her way around the room and had me deep throat the dildo while on my knees as she paused in front of each lady.
Each of the guests offered encouragement and I did my best not to gag completely. Then when it came to actually fuck me with it, Kitty had a bit of a conundrum.
Bent over a chair?
Her sitting and me doing "reverse cowgirl"?
Since we didn't have a proper spanking bench, just having me on all fours with her kneeling behind me seemed the best choice. She entered me and due to my previous stretching from the pegboard I was very relaxed and loose. Not only did it go in easily, it felt AMAZING! She gave several thrusts and then had me move to another spot on the floor so all the ladies could have a good view.
One remarked that my cock was completely limp. I told her that from all the pegging videos I had watched, that was fairly common. She said "then DO something about it!" and Kitty gave me permission to touch myself. I started wanking and was hard in short order.
After a few more minutes of pegging, Kitty suggested we take a break and I serve a fresh round of drinks and seconds on cake. While I was doing so, several of the ladies complimented me on my endurance and willingness to please. Then after clearing away the plates, Kitty suggested it was time for the "finale".
First, she went around the room and asked each lady to honestly judge whether or not I had earned my climax and if there was anything else they wanted me to do. Every single one agreed I had earned it and no more pain or service was needed. So, after some discussion on position, Kitty felt it would be easiest for me to lay back on the recliner with a towel under me.
So I took my place and started wanking with earnest. However, despite all the sexual humiliation and pain and other things I had done that night, for some reason I had "performance anxiety" and couldn't get a solid erection. The ladies were all very understanding and gathered close to me and started gently stroking and fondling me all over.
OMG THAT DID IT! I got VERY hard and after another minute or so I burst into a climax SO intense that it almost hurt. I shot a massive load all over my stomach and chest. After pausing a few moments to recover, I scooped up as much as I could with my fingers and ate it all.
What an incredible evening!!!
