It began as two boys who both were tentatively available on Wednesday... boy m and the new boy d, whom I met in the dungeon. I told them that the first to confirm gets the date, and that was d. When m tried to confirm, I was initially slightly stressed about letting him down and missing the opportunity, since it doesn’t happen often.
Then I realized: this is not a bug, it's a feature.
boy m is My lightly collared bi boy, and d is curious about playing with a man for the first time. I’ve been popping a number of d’s cherries, feels like at least one each visit. And I have tried at least twice to arrange boy play for m with previous partners, but it never panned out. I adore them both, find them both very attractive, enjoy them both naked. This. Could. Work.
If I dared to try.
It could go down in flames as have prior attempts. But it looked bolt-of-lightning suddenly promising.
I sniffed it out, the two of them being willing to meet and play. Figured out their concerns, got prelim buy off, enough to proceed. They agreed. And neither cancelled.
In a snap, there we were, the three of us, all in one place at one time, on the same page. d brought a dynamite dinner. m brought good wine.
I had m strip and put on My house uniform slave pants in addition to his survival ankle-bracelet collar.
We assembled dinner together with m half naked, d at the stove, Me directing what to do next in coordination of the activities in a small space. I alternated touching them individually, first out of sight of each other, then within sight, warming each up and bringing them along the path step by step, leading to having m embrace Me from behind while I pulled d into My front. I got to be the filling in the oreo.
It was already Good. As we ate the yummy dinner and sipped from My crystal goblets, using My nice vintage dishes and silverware, I teed up conversation and asked directed questions to deal with all the issues and make sure they each displayed to the other the things I knew would be attractive. We had a lovely dinner of panzanella salad and an italian eggplant with egg dish, just divine, the wine was great. D remembered My dietary preferences without prompting, which touched Me.
d wanted a masculine guy, and m is that. In his 60s, m does crossfit and triathlons, was a military pilot. That was more than enough for d to start cuddling up to Me so I knew he was ready to be sucked by m.
m is a slut and I rather doubt he would have refused any cock I order him to be used by. But it was also the first time we had done this so I was taking nothing for granted. As dinner progressed, I reached out and petted each on the thigh, prompting them to slide their chairs closer.
After dinner I had them clean up and put away, at first just by themselves with Me sitting in luxurious idleness in the living room. Their first time interacting one on one; I listened closely from a remove. Then a question came up that required My presence. So we talked as they work worked, m washed the dishes shirtless in his collar and slave pants. he told d about his collar and what it means, how it works for us.
After another the sandwichy hug, I took them each by the hand and said... dessert is upstairs.
Upstairs, I turned off the overhead lights, turned on the salt lamp for ambiance, ordered them to strip, then pulled them in for a three way hug. m let his hand slide down to d’s cock early on, d didn't reciprocate immediately. I ordered them onto the bed, Me in the middle, and they petted, nibbled, caressed and took turns fingering Me in an amusingly chivalrous way.
I had two hard cocks to choose from, both delicious specimens and each attached to a sexy man I like very much. Both are otters, I apparently like otters.
It was magical, everything was flowing, there was good conversation and smiles, it was lots of glow. I felt Myself steering events, but with a light hand, keeping everyone on an even keel, including Myself.
At one point I told m to move his hand up one centimeter as he fingered Me and that got Me a nice, medium cum. They later both laughed about Me very specific measurement instructions, which was a sweet moment for the three of us.
After My cum, I ordered m into the middle and he never even laid down, he went straight for d’s cock which was fully hard fast, and d raised his arms over his head in that gesture of surrender I love to see. It must be some kind of mammalian rub-my-tummy reflex.
m threw himself into the task, crouched over, ass in the air, their feet touching which I found very sweet to see.
Then it gets blurry what happened when and how. I watched, I petted mike, I laid beside d and talked to him, I dirty talked each of them, making them say what they wanted, what they liked, making them own it. I tortured d’s nipples, even slapping them hard. Such a little nipple pain slut he is, gets him going. Eventually, I got up, gloved up and penetrated m, first one finger, then two. That made him moan a little, d liked the moaning around his cock so I made m moan more. It was getting extremely fun.
Now I was talking about how m needs to be used at both ends, needs to be full of cock in all his holes, and how lucky d was to be the beneficiary of m’s holes... I made sure to hold eye contact with d as I penetrated m, made sure d knew what m was experiencing while he sucked.
I coached d to use his hands to guide m’s head, show m what he needed, make good use of him, they both liked that.
After opening him with two fingers, I put a condom on a good sized dildo and pressed it in firmly. I was telling d how m likes it when a man pushes past his resistance and isn't too gentle, so I wasn't too gentle. m began moaning louder with the prostate stimulation, which d enjoyed. I gave m a little reach around but he had softened. Eventually I had him kneel up and gave control of the dildo to a surprised d... m liked that even better, and I put some lube in my hand as I stroked him soft.
I quietly told d I was sure m would welcome getting fucked at this point, but d demurred. m let it be known he needed a break and went to the loo. I laid myself on d and asked him if he was ready to suck cock for the first time, right now. he eagerly said yes.
When m returned, I ordered him to the middle of the bed, d quickly got into position. m was not hard after taking a dildo and having a bathroom break, so he encouraged d and let him know it felt good even though he wasn’t hard yet. d persisted in figuring out how to get m’s sizeable cock in, how to vary his attentions. m gave him good feedback and soon d had m breathing heavily, his arms above his head, Me along side kissing and petting him and interwaving My fingers with his, sometimes reaching to run My fingers through d’s hair or hold his arm for a bit so he felt connected. m would periodically offer a sentence about the different facets of sucking cock... sometimes it is just about cock, having a cock in your mouth, needing a cock in your mouth... sometimes it is about cum, you want him to cum... sometimes...
As d sucked and m alternately moaned and talked, something unexpected happened. It took on a quality of timelessness, the older man teaching the young inexperienced one how to please him. For a few seconds, it felt deeply ancient to me. Suddenly felt very much the window I have long wanted into the gay men’s community, watching older men teach younger men, watching a Daddy be a Daddy to his boy, in the way of the ancient band of Greek warriors who were lovers.
I offered d a break after a while, to rest his fatiguing jaw, but he declined. Eventually they took turns back and forth. I should have made them 69. I fondled and petted them, My two beautiful pleasure boys together.
I reminded m, as he spoke about sometimes it is the cum, that he was not allowed to cum until he asked and was granted permission. In time I heard: Miss, may I please cum?
I asked d if he was ready for m to cum and he affirmed, so I commanded m to cum, talked them through the cumming, and d kept steadily to his task, drinking him in without hesitation. When it was complete, I motioned d to join us and he lay on top of Me and m, and we caressed and petted and held him. After I moved him to my right side, I turned and congratulated him, told him I was proud of him, told him I just knew he would be a good little cocksucker. he blushed a little and cuddled into me further. I turned to my left and kissed m, stroking him and smiling. We lay like that a delicious good while, floating together in a pink salt lamp haze of happy hormones, Me held by two arms on both sides, completely embraced with just the right pressure, alternating back and forth between two men I adore. m kissed Me tenderly on the forehead. It was as if I was being truly hugged in the way need, for the first time ever.
Eventually I had to ask the time, m had a hard stop that I respect. The clock gave us just a few more minutes then I had to order him up and dressed. I popped a dress back on and after a half hug followed up with a hale and hearty, manly handshake (“Great to meetya, man!”), m and I went down stairs, and I saw him out the door.
d and I spent another two hours cuddling, playing a little more, processing, talking, laughing, until it was time for him to go too. In this time, we each said: I like you. The last go-round he added after a pause... a lot. I wanted another cum but some switch had flipped, maybe probably I was just replete with all that had happened. It is enough for now.
d dressed and buttoned only one button of the shirt, as he sailed out the door, I felt dimly that his hands were too empty. Five minutes later I realized I didn’t given him back the salad bowl from the dish drainer or the box of things on the desk. No matter.
he is making Me pizza Friday.
I feel something important happened here. Not just that after 25 years I finally was able to watch close up as two attractive men pleasured each other. The Princess work paid big dividends tonight. Here are some of the ways:
- I didn’t overstress about having double booked them
- I quickly realized that the problem was an opportunity
- I dared to dream it could happen. I named it. I risked it.
- I communicated what I hoped for and coordinated a willing threesome
- I didn’t particularly worry about it going badly in the hundred ways I was fully aware of
- I did a lot - I did everything right - to create the conditions for success, and I did it with ease and grace. Even the 30 minutes of fast house cleaning between work and their arrival was ok
- I remained present in the moment, present with each boy, with Myself, and with them together.
- I stayed in My body and allowed myself to be pleasured by two men, allowed Myself to relax into that experience
- I didn’t do anything much that I didn’t truly want to do
- I teed up the questions that needed to be teed up; I engaged in the kind of deeply intimate leadership I’ve maybe not been good at earlier points
- I led each boy in the way particular to his wiring, balanced with consideration for the other
- And I held onto Me, what I want, throughout. I kept enough focus on Me.
Also, I really really felt Masterful having two boys serving Me in the kitchen and doing a good job. I would love to be accustomed to that. I felt ready in those moments, ready to allow more than one person at a time to love me, in all my glorious weird wonder. Maybe in some small way I didn’t notice, on some level I have been dismissing each individual boy as a fluke, an outlier. But two of them together working in tandem like that, wow, that felt very real. That was an almost out of body experience of feeling so loved and supported I was floating.
I was Sally Fields inside right then: You like me. You really like me.
“Everyone likes me. I like people. People are kind to Me.”
Something very deep in Me and Princess, something I didn’t know was there, got something it has really needed.
It was only afterward that I thought of it as a menage a trois, Fmm. I really had not focussed on the idea of them both pleasing Me. In the planning, I had thought of it as Me procuring what they wanted so I could watch, fulfillment of a wish I first made half a lifetime ago. I thought that’s what I wanted. But looking back, what was most powerful was being held by them, one on each side of Me. Held, caressed, pleasured, cuddled, honored.
And with the Princess vulnerability, I was relaxed and received it all. On some level, I felt hugged for the first time in My life. I could FEEL it, it felt more right than one person hugging Me ever has. That was strange and awesome. I can only imagine what dormant early wiring that might have activated.
I thought I might have let go of the Master energy or lost it when Princess arrived, but it came roaring back, somehow more real than before. More... authentic.
I spent the next 24 hours, including a whole day at work, on clouds. High, actually. Definitely a neurochemical high. I laughed in the office maybe 8 times that day, that never happens. It felt so good to laugh so easily, to feel joyous laughter just bubbling up out of Me like from a spring or fountain. It was delicious. I would love to feel that way all the time.