Werebear

Tenderness

I led him to the bedroom, and we spent some time engaged in sensual touch and kissing. I took my time building his sexual energy, and I was surprised by how in tune with his own body he was. He corrected me a couple of times, then apologized, “They teach workshops at the center around sensual massage and tantric practices for men. I’ve picked a few things up here and there.”

“Well I guess you’re going to have to teach me, at least when it comes to that stuff.” Then rubbing my fingers across his hole, I said, “But I can certainly help you with this.”

His asshole was super sensitive and any contact with it immediately made him shudder. “Did they teach you how to douche in those classes?”

He smiled. “They offer a series of workshops that include that, but I’ve never sat in on that particular one.”

“Well, now’s your chance.” I took him into the bathroom and gave him what he needed, explaining it as I handed it to him. “Most people prefer to do this without being watched. I’ll pull the door to and you can just yell if you have any questions.” It’s pretty straightforward so I didn’t expect he would. While he was doing that, I searched through the bureau and found my old anal training kit. I bought it years ago when my ass was as tight as his, but I hadn’t needed it for quite a while.

I heard the toilet flush and knew he was finished. “How’d it go?” I asked through the door. He just opened the door and strode up to the bed. Then bending over the edge with his ass in the air, he said, “I don’t know, you tell me.”

He certainly was not shy about asking for what he wanted. I went over to the arch and saw that Starlight was still sleeping. I pulled the curtains and, returning to him said. “We might want a little privacy.” Spitting on my fingertips, I slipped my hand between his ass cheeks and massaged his hole. Using my other hand to spread his cheeks, I brought my face in close. Like every other part of his body, the scent of his ass was intoxicating. I plunged my face between his cheeks, licking his pucker while producing as much saliva as possible. Once he was well lubricated, I began rubbing the whole length of my face in the musky wetness. The roughness of my beard made him shiver. He was ready.

He noticed the box full of butt plugs I had set on the bed while he was in the bathroom and asked about them. “A training kit, I said. Multiple sizes so you can work your way up to the big ones. I thought you might want to use them.”

He picked one up and looked at it. Then putting it back he said, “I’d rather have you in me than a piece of plastic.” Then reaching back to spread his cheeks for me, he said, “Do that some more, it was nice.”

I continued to eat his ass, occasionally running a finger across it to keep him used to my had being there. Mostly I played with his taint and stroked his cock, which was becoming increasingly hard. After a while I asked, “Are you ready for a finger?”

It was his turn to be in that non-verbal place, He just nodded and moaned. I began to apply pressure against his sphincter, instructing him to push, like he was taking a shit. I felt his hole move as he pressed out and released. “Good,” I said, “Do it again.” He did. Told him to keep it up as I massaged more spit into his hole and started to apply pressure in sync with his rhythmic pulsing. I applied just enough pressure to stimulate him without letting my finger penetrate him.

Once he had the knack, I buried my face in him one last time to make sure he was well lubricated. Then pressing my finger just a little harder than before, I allowed his ass to swallow it. All I heard was a slight gasp. He was certainly ready. I asked if he was ok and again, he just moaned. Then I told him to back up against my finger and see how deep he could take it. He ended up taking it all. Once it was all the way in, I pulled it out a little and thrust it back in, slowly finger fucking him,

From there I moved to two, then three fingers, allowing him to take his time and stretch himself out. When I finally pulled out, he let out a long moan. “No,” he whispered, wiggling his ass as if to call my fingers back. “it’s just…” he couldn’t find his words, so I helped.

“Empty.” I laid on the bed next to him and said, “I know. After you’ve been filled like that, it just feels so wrong, like a part of you is missing.” I kissed him and said, “Time for a break. I could certainly use some water after drooling about a gallon of spit on your ass.”

“But when do I get your dick?” he had rolled over and was rubbing his empty hole with longing.

“Soon. But first, I need some water, and you need to pee.”

“No, I don’t,” he insisted.

“Yes, you do, or at least, you will. Trust me, when my dick starts pounding your bladder, you’ll be grateful I gave you a heads up. I don’t particularly feel like doing piss play tonight.

“Oh,” and he padded off to the bathroom. I grabbed a bottle of water and prepared for round two.

When he emerged, I was on the bed waiting. I had him sit on my face so I could eat him out some more, but this time I told him to lean forward and suck my cock while I did it. “Get it nice and hard,” I said, before sticking my tongue up his ass. It didn’t take long before he had taken me to that non-verbal place with him, and without a word I climbed out from under him, flipped him over, and began rubbing the head of my dick against his hungry little hole. He began the anal pulsing that I had taught him earlier.

I threw his ankles on my shoulders and leaned forward, allowing my cock to apply more pressure on his throbbing hole. His face lay between my hands, directly below my face. I wanted to look in his eyes as he let me in. His eyes betrayed how vulnerable he felt. There was fear, but there was also trust. He was letting me see a part of him that he had never shared before. He wasn’t just letting me into his ass, he was letting me into the deepest part of his soul.

As I watched the fear and elation in his eyes deepen, I continued to gently thrust in rhythm with his pulses. “Whenever you’re ready,” I whispered, giving him permission. Suddenly I was inside. His ass had swallowed the head of my dick in one smooth motion. He had been keeping eye contact with me, but when I finally entered him, he rolled his eyes back and whimpered a little, and the pulsing stopped.

“It’s ok, It always hurts a little, especially the first time.” I leaned forward and kissed him softly. “Now open your eyes and look at me. Stay with me. I’m here with you. It will pass. When you’re ready you need to start pulsing again.” I watched as waves of pain passed on his face. I saw them grow less intense as his gaze turned inward and he became familiar with them.

I applied a little more pressure, to see if he was ready and he responded with a single pulse, then another. I started sliding my dick deeper in and saw the same internal struggle on his face as he embraced another new sensation. I was in far enough now that I could begin a slow gentle pumping, in and out. He grasped my arms tightly, struggling to find solid ground in this sea of new experiences. “You ok?” I asked softly.

He nodded no, but the words he managed to utter were, “Don’t stop.”

I continued, paying attention to his eyes and body language. I had taken him to his limit and maybe a bit beyond. After a while, his expression changed, and he began to squirm in a way that seemed like he had had enough. “Do you want me to stop?”

“Yes, enough,” was all he could muster. As I pulled out, I saw that same mixture of relief and longing return to his eyes. He needed a break, but he felt so empty without me inside him.

I held him as he faced the strong feelings that come with being fucked. He was an expert cocksucker, so he already understood the nature of submission, but there is a deeper level of submission that must be faced when it is your ass that’s being breached.

“Did you cum?” he suddenly asked. He looked concerned, like he had failed.

“No, but I didn’t expect to. Tonight has been about you. “Besides,” I assured him, “I can cum anytime, especially if I have you around to suck my dick.”

We drifted off to sleep, but I was awaked at three by his magic tongue. He clearly wanted to try again. I handed him some lube and told him to go ahead and sit on it as much as he wanted. This time he went much deeper before he felt the need to climb off.

The next morning held the same promise as yesterday. I awoke with intense morning wood, and me memory of the previous evening made me even harder. I rolled over to spoon with him, and he responded by handing me the bottle of lube and saying, “Do it.”

I did. This time he laid himself on his belly and let me do all the work. I could still sense some tension as he took my cock, but it was manageable now. I stopped worrying about his experience, trusting he would tell me if I were hurting him or going too fast or something. I focused on my pleasure and it wasn’t long before I filled him with all I had to offer. I stayed inside him for a while, letting my dick marinate in my own cum, and again, we drifted off.

I was awakened by the soft sounds of Starlight scampering to the bathroom for his morning clean up. I had rolled off Twinkle-Toes, who was still lying on his belly. My dick was soft but still moist with cum and lube. I must have only slept a few minutes. I leaned over and kissed the back of his neck, being careful not to wake him. Then I joined Starlight in the bathroom. “I need a shower.”

Our main task for the day was to prepare for our trip to the retreat center tomorrow morning. The naked weekend continued, and I wondered if I would be doing this there. I mean, it’s one thing to run around naked in the privacy of your own apartment, but outdoors? with lots of others around? I wasn’t sure, but I wanted to give it a try. Once again, the day passed uneventfully. We checked in with Sniff and made the final arrangements. Later we decided to visit the basement gym again, so we did have to put on shorts, but we agreed to not wear anything under them, so we could flash each other at will.

As the evening drew to a close, Twinkle-Toes asked Starlight if he would join us in the bed tonight. “I just miss being near you.” We spent the night cuddled up together in warm contentment.

Monday was the big day. We all showered and got dressed, and after a late breakfast we began packing for the trip to the retreat center. Starlight took charge. He told me and Twinkle-Toes to start loading the car while he checked in with our guards to let them know we were about to leave. By the time we put this in motion it was almost noon. The retreat center was only about a half hour drive, and the moon wouldn’t rise for hours. We still had plenty of time. We all left together, splitting up as Starlight headed to the lobby while Twinkle-Toes and I headed down to the parking garage. We dropped the bags by the car and Twinkle-Toes volunteered,” I’ll head back and make sure we didn’t forget anything.” I watched his cute ass as he began to climb the stairs and sighed. As I turned to put the bags into the car, I felt arms grabbing me and a hand roughly forcing a rag over my face. Then everything went black.