“Life is meandering between passion and pain.” – me
“Life is pain…As light as pain.” – Gray
“Life is as light as pain and as heavy as love.” – me

Today (the 15th) was Gray’s birthday. He just so happened to be teaching a cigar play class near me, for which I was the demo bottom. Before heading to the Playhouse, I picked him up, dressed as dapper gentleman, down to his stylish suspenders and handsome hat. We had a delicious sushi dinner, which I tried to pay for (it was his birthday), but he insisted on giving me half the bill in cash later.

“I got the impression he was into you.” – Gray
“Really?” – me
“You didn’t get the impression that he wanted to play with you?”
“Yeah, when stuff like that happens it almost always goes over my head.”

The class was quite fun. Gray and I have played a lot with cigars; my lamp table, with its cute assortment of burnt clothing, can attest to that. Though I knew the basic outline of what was going to happen, Gray also incorporated more activities he’d picked up in his travels. I enjoyed the “smoke rise”, as well as his sadistic sensation play with the hot cherry.

But, of all the new tidbits, my favorite was the cig-matta. With ash from Lochai’s cigar in Gray’s palm, Gray grabbed my hand and made me endure the pain of the hot nugget. All the while, he felt the same; we shared the burn. Next time I will stare into his eyes as he had wished me to tonight; I could not fulfill his request at first. I can still feel the spot in the palm of my hand from his hold.

“Wow, that yoga is really paying off.” – DeepEnd

“It looks like pounds have melted off of you.” – Gray

It’s hard for me to see it, but two different people tonight commented on my lost weight. I still don’t know how to process that other than I will keep up with my yoga/treadmill/bike riding, if for no other reason than they are fun activities that help get me out of my head. And I guess because obviously others are noticing what I cannot.

“Do you want to suck my cock?” – Gray
“Yes.” – me
“Beg me for it.”
“Please let me suck your cock.”
“I don’t believe you.”
“Please let me suck your cock. Please. My mouth misses the feel of your cock inside it. Your cock is the only cock I want in my mouth.”

After the class, which included elements of service, knife play, a lovely smack across my breasts, a cigar blow job (which I quite enjoyed), and so much more, Gray and I had time to play. He brought an assortment of mean things to use on me.

His cane was the first of Gray’s toys to receive attention. Initially Gray had me lying on the floor, using the heels of his shoes to press into my nipples. He then used the cane to hit my nipples, at first lightly, but then with suffering blows.

Gray spread my legs and focused his attention on my clit and pussy lips. Again he started lightly before steadily increasing the force of his blows. Pain and pleasure danced in my nether region as I moaned through his strokes.

Gray ordered me to lie in front of him in child’s pose. With my arms at my sides, my chest rested against my bent knees. Gray went for my ass, starting with soothing strokes. As he increased the pain, I started yelping.

Gray ordered me to reach back and begin fingering myself. As his strikes stung and burned against my flesh, my fingers whirled frantically. The pleasure rose and I begged permission to cum. Gray said I could, but only after he inflicted three wicked blows across my ass.

Ordered up on my knees, Gray used his cane on my breasts once more. Pinching a nipple, he lifted my breast and struck on its underside. This was a first for me.

Finished with his cane, my ass then christened his new paddle. Gray had me lay across his knee, my ass ready and accessible to his bidding.

Gray started unexpectedly with thuddy strokes using the edge of the implement. As he beat into me, I moaned. Gray then switched to light stingy hits. He was preparing my ass for what was to come.

Gray smacked my ass hard, the crack of the blow bouncing off the walls of the small smoking lounge. Again and again, he wailed on my ass, but while also fingered my clit with his free hand. My voice traded shrieks and moans back and forth. His playing with my clit caused another orgasm to rise in me.

Like always, I asked permission. He said I would have to endure five hard paddle strikes before my cum. In quick succession he stung my ass with the toy, holding for a moment before giving me his fifth stroke, and with it my permission to cum. I writhed across his knee, moaned, struggled to breathe as the sensations rolled throughout my abdomen.

Afterward my reward came the fun part for Gray. With sadistic glee, he again used his paddle to beat my ass, no pleasure given to ease my pain. He steadily increased his hits until, in need of a moment of respite, my knees buckled and I collapsed down.

Two breaths later, I was back up across his lap ready to endure whatever more pain he wished to inflict. Again he smacked my ass, stinging blow after stinging blow. Finally my body let go, the pain washed through me, and I sobbed and cried.

Gray put aside his paddle, and brought me into his arms, soothing my cries. As he stroked my hair and held me tight, he softly whispered, “That was beautiful.”

I was granted the pleasure of sucking his cock multiple times over the course of the evening. He helped me practice my deep throating, first swelling inside me and later ordering me to hold his cock in my throat for a few breaths at a time. I still need quite a bit of work. I gagged multiple times, but once or twice I was able to keep his cock down while relaxing my throat muscles. Baby steps.

Once, as we were coming down and I softly nuzzled his crotch, he allowed me, as part of the process, to again suck his cock. He dubbed it a “cuddle blowjob”; I lightly, softly sucked on his cock in a nurturing comforting fashion as my head laid in his lap and he brushed my hair.

Gray also, as a part of our aftercare, drove me to orgasm just by pinching my breasts and nipples incredibly hard. At one point, he pinched them as hard as he possibly could. There is just something magical about my nipples and the mixture of pleasure and pain. My orgasm was a new experience for the both of us.

As the night grew to a close, we gathered our things and prepared to leave. There were hugs all around for the few who stayed for so long, and pledges to see one another at WinterFire.

I drove Gray home; sleepy conversation and general checking-in made the drive pleasurable.

“So, what is your relationship status?” – Gray
“Ha, I have no relationships. I have lots of friends. I fuck a few people. I play with a lot of people. I am emotionally connected to some, but no. I have a lot of friends, but no partners…I have a plethora of appetizers, but no main course.” – me

At one point, Gray grabbed my hand to demonstrate a special sub-dermal piercing two known figures in the kink community had. As he held my hand for that short time, less than thirty seconds, it dawned on me that I had not held hands with someone in a long time.

And at once my mind cut itself on a dual edged sword: I am a happy-go-lucky free single kinkster having lots of slutty fun. I have no one to share in my happy-go-lucky slutty kinkster existence.

And just as the thoughts came, Gray released my hand and I went back to focusing on driving. The trick with being Unpartnered Poly is to not think about it. Just let life take you wherever. When you figure out how to do that, please let me know.

I picked Gray up at 4:35pm (traffic) and dropped him off at 12:15am. I have yet another set of burnt clothing to add to my collection, as well as two burnt cigars from our presentation. He has a handmade scarf and some chocolate to snack on.

It was a lovely evening spent with a great friend on his birthday.

Categorised as: Cigars | D/s | Gray

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