Barry Pegged with Witnesses

Due to a scheduling conflict which cropped up for Carol, Barry's witnessed pegging was postponed from Thursday until Sunday evening.  It turned into a very interesting time for everyone involved.  During the weekend, I seriously wondered whether or not Barry would go through with having Carol and Helen witness me pegging him.  I knew that he has a huge submissive nature and that he really wants me to peg him more often.  However, deep down, I was still surprised that he agreed to the witnesses.  I will also confess that I  had some misgivings about what I set into motion.  I began to have doubts about whether I would be comfortable performing this very personal act with my husband while someone watched.

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.

As we finished our dessert, I asked Barry to go to our guest room and change into the clothing that I had laid out there for him. While he was gone, I placed two dining room chairs in the center of the living room, about one foot apart and facing each other. When he returned to the living room, he was dressed in a lovely chemise with gartered stockings and a matching panty.  He was looking quite sheepish and embarrassed; I couldn't help but comment to the two other ladies about how cute he looked and they quickly agreed.  Helen even added a comment about how much she enjoys seeing his privates locked up.

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 taking his position on the bed, Barry was at a right angle to Carol and Helen, so he was not looking directly at them.  I had initially thought of positioning him so that he faced them, but decided not to do so.  I thought it would be better to give him the option of not having to look at them while being pegged.  This position also provided Carol and Helen with a wonderful view of what I was doing to him.   I took my time in lubing both Barry's bum hole and my strapon before slowly and gently beginning to insert it.  It took about five minutes before I was able to fully insert the dildo.  During that time Barry was acting like the little slut that he is as he moaned and groanaed the entire time and I kept teasing him about what a horny little slut he was.  After I was fully in him, I continued to slowly slide in and out of his bottom with the dildo.  He of course was loving it.

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 decided that this was a good time to surprise Barry with Carol's strapon.  After letting him get up, I placed one of our high stools from our kitchen island into the center of the room.  I don't know if Barry had noticed it off to the side of the room or not,but he seemed a surprised by it.  After directing him to bend over it, I made sure that his waist area was over the center of the stool and that he had solid footing with his legs, which I slightly spread., I again proceed to enter him and slowly fuck him.  He again went into slut mode with his moaning and groaning as he enjoyed what was happening.  I then suggested that we were going to see just how much of slut he is.

 I asked Carol to stand and walk over to face Barry.  Show Barry what you have for him, I directed Carol.  She walked right up to him and started to slowly stroke the bulge which was evident beneath her skirt.  When Barry realized what she was doing, he immediately looked back at me and pleaded "Please, no".  I just stared back at him and advised him that I thought it would be fun for him to suck Carol's cock while I continue to fuck him.  Carol began to remove her skirt and then placed her cock into his mouth.  Barry was a reluctant participant at first.  However, as I proceed to more aggressively work his butt with my strapon, he became more involved.  Suddenly I hear Carol give out a little gasp and I realized that it was because Barry had grasped both of her bottom checks with his two hands and was very actively sucking her cock while he fondled her ass.  "Look at our little slut" Carol said.  "He likes to suck cock ... and he apparently also likes my ass".  I started to reprimand Barry and make him move his hands.  However, Carol stopped me and explained that it seems to allow him to more fully take her cock all the way in.  I think he is actually deep throating it.  After several more minutes, I decided it was time to move to our final position.

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.

With us all in close proximity, I began to milk Barry more actively as I fucked him, again warning him not to come.  It didn't take long before he began to beg me to allow him to cum.  I slowed down a bit, but then raised the intensity again.  After going through that cycle several times, I could tell that he wasn't going to be able to hold out much longer, so I gave him permission.  Within ten seconds, he exploded, shooting his semen all over the front of his chemise.  Carol took advantage of that to rub her strapon in the semen and then place it in front of Barry's face again.  Much to my surprise, Barry quickly began sucking it again.  Carol repeated that act several times until she had cleaned up as much of his cum as she could.



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.

Susan