Pegging My Dom

Over the weekend, I saw a bit of DeeDee and MasterDoc while DeeDee was visiting for a week. I arrived when they were just starting a show; MasterDoc had sent me a text telling me to be in sub mode when I walked in. Their guest was a  guy writing book with chapter on BDSM, looking to research it for the book. From what I heard he had some erroneous ideas about BDSM. Hopefully he will listen to what he learned from DeeDee and MasterDoc and write something at least somewhat accurate. (I’m not holding my breath.) I hid myself in the bedroom while they did their show, and it was incredibly hot to listen to the spanking from there. The pitch rose until DeeDee was begging to come. Rowr. I got called in, and found DeeDee on the sybian. MasterDoc wanted me to help paddle her while she came. I gleefully obliged. He said I wasn’t hitting her hard enough but her butt was definitely more rosy after I paddled her. She recovered on floor after, and while he tended to her, MasterDoc had me lead the guest out. When their guest mentioned needing a place to sit to put on his shoes, I p0inted out that there’s chairs in the dining room. Dickwad looked at me, said, “Yes I saw that.” So much for trying to be gracious and helpful. I wasn’t just being a sub, I was trying to be a decent hostess. Snide comments are not appreciated. Jerk.

During the visit DeeDee did a lot of the fetching but I got asked to chip in with some cleaning. I was happy to have some help , but when DeeDee would do something like get me a drink, I felt weird being at all waited on. I’m not used to that. My mother used to tell me I’m spoiled, but it dawned on me that night that I got used to caring for myself at a fairly young age. MasterDoc pointed out that I let Davey do stuff for me, but I pointed out that initially he had to convince me he wanted to do that. I would do stuff myself and he’d get frustrated because he likes feeling needed.

The plan for the evening was for me to use a strap on on MasterDoc. Yes. You read that right. It’s rare that he lets a woman peg him, and he only ever lets submissives do it – while another lady blows or plays with him. These criteria need to be met before he will do it. He’s talked for a while now about letting me do it, since we’ve developed an adequate level of trust. (The last time was years ago with his submissive at the time.) It’s funny, because usually he’s totally comfortable with liking anal stimulation as a straight guy. He’s really sex positive and not the least bit homophobic usually. But when a strap on enters the picture, he gets a little funny. He has to have another woman sucking him off at the same time so it’s “not gay.” He admits it’s absurd, but he’s to some extent a product of his generation.

We were setting up in the living room, and chatting, trying to ease into the scene. Somehow in the course of conversation I came out with, “In my time we had to walk down to the store to buy porn! We didn’t have the internet!” as an “In my day we had to walk a mile, uphill, both ways to get to school,” sort of thing. We laughed and talked about coming up with more. I thought for a bit and came up with, “In my time we had to use Crisco because there wasn’t lube at the corner store!” Hopefully I will manage to come up with a few more. (Can you think of any?)

I got down to business working MasterDoc’s ass over – massaging, lubing – while DeeDee sucked his cock. I gradually worked a finger in at his request and after trying to loosen things up gently with my finger I gradually worked a butt plug in. After some play with the plug, MasterDoc decided he was ready and he got on hands and knees as it seemed the best position. I had my harness on with my red glitter, silicone dildo, a slim one I specifically bought a few years back to peg boys with. MasterDoc kept telling me to add more lube, and my hands were so slippery I could barely handle the lube bottle! Getting lube into his ass was tricky. We need to get one of those applicators that let you apply lube inside the anus. Lubed as much as I could get him, I tried to get the dildo in. DeeDee was playing with his cock in the meantime. I’m not sure how much of the dildo got in there, probably very little. MasterDoc had me stop for a minute because it hurt, and by then my knees had given out from kneeling on the floor. We had to stop for the night. So it wasn’t entirely successful, but we gave it a shot. I’m sure we’ll try it again sometime.

As I was quite horny at the tail end of the week, and hadn’t had sex in a few days, MasterDoc offered me a horsey (sybian) ride. I had a hard time getting into mood though. Sometimes I can pop on top of the dildo and get warmed up as we go, but I needed foreplay before sticking anything in me that night. MasterDoc worked on it, sucking my nipple and such. As DeeDee walked by to go to the kitchen, he got her to come in and suck on my other tit, and I played with my bullet vibe on my clit. Turned on enough that I might come if we went further, he put me on the sybian. MasterDoc had DeeDee paddle my ass like I had done to her. She did it too light, unfortunately. I managed to come even though it was hard to get myself in quite the right headspace that night. All in all, everyone got some attention that day. I slept in the spare bedroom since it was DeeDee’s weekend with him, and to be quite honest sometimes I’m thrilled to sleep alone. I sleep so much better without a snoring guy beside me. It can be nice to have someone next to you, but I treasure those nights alone too.

I made a concerted effort to not take too much time from DeeDee while I hung out with them. Not sure how I did, but at one point I was hit with an attention craving, and I reasoned it out rather than asking for attention. Would I fall into a depression or anything serious without the attention? No. Could I “suck it up buttercup” and take care of myself that night? Yes. And so I did since I didn’t want to infringe on DeeDee’s time too much. I think I was more comfortable than I usually am. I think I’ve grown a bit more secure lately. Of course, in a depressed mood that could disappear into the ether, but for now I’m feeling good.