However, Carol and Helen arrived at 7:00PM and I proceeded with what I had planned. Helen brought a lovely dessert which we enjoyed with coffee in the living room. Conversation was a little stunted at first, which I think was due to a little nervousness on everyone's part.
I saw Barry looking at the two chairs, so I explained to him that I thought he might enjoy receiving a little spanking from Carol and Helen while I took care of some final preparations. He smile and agreed that being over their laps would be a pleasure indeed. I suggested that they take their places in the two chairs and proceed to provide Barry with a nicely warmed bottom as a prelude to my pegging him. I also explained that it was not to be a harsh disciplinary spanking, but it would be lovely to see some bright red color when I return. I suggested that they monitor his state of arousal and spank as hard as they could without causing him to lose his erection.
As I left the room, Barry was over their two laps and the spanks were beginning to resound in the room. I then proceeded to the bathroom where I prepared an enema bag with about six cups of luke warm water and a little soap. After taking it to the guest room and making sure I had all of the desired toys arranged on the dresser, I returned to the living room to let everyone know that all things were now ready. When I arrived, Barry's bottom was nicely colored and Carol and Helen were teasing him about what was going to happen to his bottom tonight as they spanked him.
When we arrived in the guest room, everyone immediately saw the enema bag and nozzle hanging from a bedpost. Barry immediately groaned. I explained to the two ladies that pegging is much more pleasant if the recipient's bottom is cleaned out a bit, hence the first step would be for Barry receive a nice warm, soapy enema. I then sat on the side of the bed and placed a towel over my lap and instructed Barry to lie across my lap. I then inserted the nozzle and started the flow.
In the meantime, Carol and Helen had taken their places in two upholstered chairs off to the side of the room. Our guest room is quite large which allows for a nice little sitting area with an open area between it and the bed. The sitting area provides a comfortable viewing space from the two ladies can enjoy the proceedings. Once the bag was empty, I replaced the nozzle in Barry's bum with a penis shaped butt plug. Keeping Barry in place, I then began to give him another spanking, explaining to Carol and Helen that I just really enjoy pegging Barry's bottom when it is nice and warm and red! After about five minutes, I sent Barry to the bathroom to expel his enema, instructing him to make sure it is all out and to reinsert the plug before returning.
While Barry was gone I proceeded with more preparations, but getting my strapon in place. I also helped Carol strap on my old harness and dildo under her dress. She and I had made previous plans to surprise Barry with her wearing one that she would make him suck. She and I both knew that she would not be permitted to peg Barry, but he wouldn't know that.
When Barry finally returned Carol was again seated, showing no evidence of what was under her skirt. However, Barry could easily see what I was wearing and he quickly realized that it was not the smallest dildo we own, but is significantly larger than his own penis. Standing in the middle of the room I directed Barry to come and kneel in front of me and to begin sucking my penis. Glancing over at Carol and Helen, he reluctantly complied. I kept him doing that for about five minutes before directing him to bend over the end of the bed. When he stood up, I could see that his penis was straining at the cage, so I commented about how aroused he got while sucking my cock. I also suggested that we could remove the cage if he would like. He quickly agreed and I made sure that Carol and Helen go a good few of me slowly releasing him.
After several more minutes, I withdrew from Barry and told him to stand up. I then laid on the bed on my back and directed Barry to straddle me and lower himself onto my dildo. This gave him control, but also forced him to do the work of allowing my strapon to penetrate him He slowly got into position and managed to squat onto the strapon. Once he was fully onto me, I began to move my hips and directed him to do the same. This cow girl position is one that Barry loves to do with me when we have intercourse, so I thought it only fair that he get to experience what it is like from the recipient's perspective. It became quite clear that he found in more uncomfortable than when he is on the bottom :-). Consequently, we didn't stay in that position very long, but I could also see that Helen and Carol were enjoying the perspective. They also began teasing him about being such a slut and commenting about how hard his penis was.
I then positioned Barry on the bed on his back with his bottom raised with our Liberator wedge. That put him in perfect position for me to kneel between his legs and have access to ass while looking him in the eye. It also made his genitals completely accessible. By now it was very easy to fully penetrate him, which I quickly did. Proceeding to deeply fuck him, I also began to gently tease his genital area with my hands. However, I also sternly warned him that he hadn't better climax unless I gave him permission. Carol commented that perhaps Barry would like to suck her cock again. After I gave her the OK to find out, she came over to the side of the bed and positioned herself where Barry could get his mouth on it again. Much to my surprise, he quickly did so. Since she was blocking Helen's view of that action, I suggested that she might want to come closer so she could see just how much of a slut Barry is.
I then suggested that Carol and Helen return to the living room to give Barry and I a few moments alone and that we would then join them. I used those few moments to help Barry get cleaned up and do a check on what he was feeling. I'll share more about that in a later post, but Barry was basically fine with all that had happened and really seemed to enjoy it.
When we returned to the living room, Carol had poured another cup of coffee for each of us and she and Helen seemed to be having a spirited conversation about what had taken place in the guest room. I'll share more in a later post about their thoughts and reactions. This post is getting much too long again, so I feel it will be better to save that for later. Barry, again, has volunteered to add some photos to help break up the length of this one. He and I both hope you enjoy his selections in an attempt to depict what he experienced.
Before Carol and Helen departed, I mentioned that I felt that Barry owes Carol an apology for his behavior. He immediately acted like he didn't know what I was talking about, so Carol piped in that it is for the way he was groping her ass. She added that she feels he not only owes her an apology, but also deserves a good spanking from her. I quickly agreed and told her that I would be happy to arrange the opportunity for it to happen. However, I added that it would not be tonight, because I had other things for Barry to attend to tonight. Carol and Helen quietly smiled and suggested that they really needed to get going.
After they departed, Barry and I had more time to talk and debrief, but not before we retired to our bedroom, where he took very good care of my personal needs.