The Bet

Author's note: This is a continuation of "The Bet" chapters 1-3. The plot will make a lot more sense if you go back and read the whole thing. Also, this story features a female-to-male transgender character with a gay man. If that's going to bother you, this story isn't for you.

*

I took his hand in mine and held it where he had it pressed up against my face.

"Sir, I'd...I'd like to try."

We sat like that for a moment, with me both hopeful and terrified. I wasn't actually sure whether I wanted him to agree or not, I just knew I'd never have the guts to do this on another night. I decided to push again.

"You said you had plans for more, sir."

"I did say that, didn't I? And I owe you a spanking for the way you talked to me, as well. Not only just now but a number of times during our evening."

My mouth went dry. He wasn't going to just let that go, was he? Allan pulled his hands free of mine and clapped them briskly together.

"Alright. The boy asks for more, more it is. Up you get." Allan put a hand in the small of my back and pushed until I was standing upright. He took my hand and led me back out of his office toward the main part of the club. We walked around the bar and past the dance floor to the opposite club wall, where there was a staircase guarded by a bouncer.

"Sam, I'm taking Ray down to the room I had you hold earlier."

"Of course, Mr. Glover." Sam looked me over as he opened the rope blocking the stairwell. "You two have a good time now." He added with a knowing wink.

He knew we were going downstairs for sex. That was the point of those rooms. I blushed. Allan just kept going, leading me down the stairs and through a door with the number 3 on it. He paused in the doorway to look into my face and squeezed my hand. "Your safeword still works, Ray. It always works. I don't think you're going to need it, but I want you to know."

"Yes, sir." My stomach was suddenly full of butterflies.

The room wasn't all that large. There was a bed on one side, and a door led into a small bathroom. There was a dresser on the other wall, but I doubted it held regular clothes. It would have looked like a typical motel room if it wasn't for the restraints visible on the bed and walls.

I took a deep breath. This was really happening. Allan let go of my hand and sat down on the bed, then gestured me to come stand in front of him. His firm hands turned me until I was standing facing him, just in front of his knees. We were about the same height in this position, and he took advantage of it by going in for another kiss. "I think I've waited long enough for this. Take off your clothes."

"What?" Allan slapped the side of my thigh with a resounding crack. "Ow!"

He raised his eyebrows. "Do I need to repeat myself?"

"No, sir. I mean, yes, sir, I mean, I'll take off my clothes, sir." My tongue stumbled over my words just as my fingers stumbled over the buttons on my shirt. Allan just watched me struggle, making me feel even more clumsy. At this point, my desire to please him combined with the pain from the blow when I didn't do what he asked was overpowering my anxiety about my body.

After what felt like forever, I managed to get all of the buttons of my shirt undone, and I pulled it off and tossed it away. My jeans soon followed, leaving me standing in front of Allan in my boxer briefs and my binder undershirt. I took a deep breath.

"I like what I see so far, boy," Allan said encouragingly.

"Thank you, sir." I grabbed the bottom hem of the binder and peeled it off over my head. It's not dignified, getting out of a binder, and this was no exception. I wiggled and fought, and there was a brief moment where I was stuck in it, elbows pinned to the sides of my head, but I got there. I reached for the waistband of my boxer briefs, but Allan stopped me.

"Turn around and bend over as you take them off."

I complied, sliding the material down over my bare buttocks. I stepped free of them and stood in front of Allan, slightly bent over and completely naked. My heart rate sped up. I hadn't been naked in front of a man since before I had come out as transgender.

Allan reached out and massaged my ass cheeks. His voice was husky. "Everything I hoped you would be." He said. "Turn for me."

I turned, his hands still trailing over my skin as I did so. He rested his hands on my hips as he looked me over. My hands fisted at my sides as I tried to not cover myself or cringe away.

"Yes, that's very nice."

I took a deep breath, trying to focus on the moment and on Allan rather than my own insecurities. Allan ran his hands over my whole body, as much as he could reach, as if he was drinking me in through his skin. My skin tingled at his touch, until my whole body felt sensitized.

He reached around to grab my butt and pull me even closer to him, so that I was standing between his knees as he sat on the bed, still fully clothed. I wanted to see him, too, so I reached out to undo one of the buttons on his shirt. Allan pushed my hands away.

"Naughty, naughty," he said, teasingly, "I didn't say you could touch, yet. I'm still enjoying my prize."

"But..."

Allan held a finger to my lips, silencing me. "Be quiet, boy. No more talking." He dragged his fingertip down my upper lip and pushed just a little, so it popped into my mouth. I sucked on it gently, looking into his eyes. I could see the heat in them, his desire for me so potent I could feel it in the air between us. Allan withdrew his finger and sat back.

"Let's remove that temptation to touch, I think." Allan reached into the nightstand and pulled out a pair of lined handcuffs. My eyes widened but I remained in place as Allan locked my wrists together behind me. Naked, restrained, alone. My anxiety mounted, moved into arousal as I reminded myself who it was that had locked me up, who it was that I was alone with.

"I believe I have a spanking to administer. This is partly in punishment and partly because I simply want to see how red I can make your skin turn." His strong hands arranged me where he wanted me; I followed their unspoken demands, feeling like a doll or a puppet, able to do only as he asked. I stayed quiet, though I wanted to protest.

Allan laid me facedown over his lap as he sat on the bed. Instead of having me dangle over his lap in the air, he placed me so that I was lying stretched out on the bed crossways, with him in the middle.

"I like this position better because it gives me a bigger surface area to work with," Allan remarked conversationally, as if he weren't rubbing his hands on my naked ass and thighs. He squeezed one cheek, then the other, sensitizing my skin to his touch.

"I don't need to restrain you because you aren't going to move." Allan paused. "Is that right, boy?"

"Yes, sir," I managed, turning my head and trying to look back at him.

He started off lightly, barely tapping my bottom and thighs with his hand. He moved up one leg, across my cheeks in a circle, down the other leg, and back again. As he continued, the blows got stronger and stronger, still moving around, until they really started to hurt. I whimpered into the blankets on the bed, tears welling up in my eyes.

It took everything I had to hold still and not jerk out of the way. Allan paused every few strikes to rub my ass and murmur encouragements, and then went back to spanking me. The sound of the blows reverberated in the small room, as did the sounds of my cries. My bottom felt like it was on fire, and still he kept on spanking me.

The pain wasn't entirely unpleasant, though, as strange as that sounds. If Allan wanted to spank me, I wanted to feel the pain. It was him giving me the pain, so I would take it.

I was crying in earnest by the time he stopped, the blankets under my face soaked with my tears. I hardly registered when he switched from blows to caresses. The feeling of his hand on my overheated skin was nearly as painful as the spanks themselves.

Allan grabbed my hips and pulled me back and upwards, so that I was laying on my elbows and knees over his lap. He shoved one hand between my thighs, forcing them apart, while the other continued to rub my sore, reddened buttocks. Every squeeze sent a shock of fire through me, making me want to cry but also turning me on. I whimpered, not sure if the sound was pain or need.

Allan's hand slid forward and grasped my clit. Thanks to years of testosterone therapy, it grew to just over an inch in length when I was aroused, like now. Allan made a pleased noise.

"I thought you said you didn't have a dick," he said, rubbing it up and down. "This will do just fine."

I moaned. Between the pain in my bottom and the pleasure of Allan touching me, I couldn't form coherent words or even thoughts. Allan kept jerking me off and lightly slapping my ass, and soon I couldn't tell the pain from the pleasure. Everything rolled together in one big mass of sensation focused on my groin. He alternated fast, hard strokes with gentler touches, keeping me on edge.

I panted hard. "Please...please..." I moaned, not sure myself if I was asking for more or less. Allan dug his fingers into my sore buttock.

"You do not have permission to speak, boy."

I whined. I wanted to beg, to scream, to thrust into his hand, but I had to stay quiet and still. Allan's heavy arm around my waist kept me from rearing back. My breath came in short, hard gasps.

"That's right, boy. You can't go anywhere, you can't do anything. You can just take what I give you." He pinched hard on one of my labia. "I like these, too. Maybe next time I'll put some weights on them, make them swing as I spank you." My whole body shuddered as I pictured it, and Allan chuckled. "You like that idea, don't you, boy?"

I just moaned again, unable to speak. Allan jerked harder. "That's right, take it. You like it when I touch you, when I hurt you." He punctuated this statement by bending down and sinking his teeth into the curve of my ass.

I screamed as the world went white and fragmented into a million pieces. I collapsed across Allan's lap as the orgasm shook me. Allan pulled his hand free from underneath me, and as my shudders slowed, smacked the sore skin, sending me back under. I have no idea how long I was lost in waves of sensation. I entered a place where time didn't matter; nothing mattered, except Allan.

I came back to reality and found that Allan had arranged me in a seated position on his lap, my face snuggled into his shoulder. My hair was matted with sweat and my backside ached where it rubbed against his pants, but I felt intensely satisfied. I sighed and snuggled deeper into his arms.

"Back with me, boy?" Allan asked into my hair, kissing the top of my head in the way he had.

"Mm-hmm." I said, too cozy to form real words.

We sat like that for a long while, until I was finally able to convince myself to move from my position against his chest and sit up.