Cuffing Season Ch. 02 - The Awakening

All persons in this story are over 18 years of age and the names of characters and places have been deliberately changed to protect the identities of all involved.

It was Sunday: Ben - my gardener and handy man for years-- had a big mess of overgrowth and high grass to take care of in the front yard. After a solid hour of work, he finished and came inside. (Inside is slightly cooler than outside in the tropics.) He took off his sweaty clothes and got in the shower: I had lots of fantasies but his cock and my parts just didn't match up at 6' something- really- fucking- tall with my 5'6". I watched him soap and stroke himself, slapping his cock on his belly, showing it off, before forcing myself to wander off to the air conditioned bedroom.

In a few minutes he appeared, toweling himself off, and the two of us plus a towel landed on the bed. I confess I couldn't resist his shiny clean dick and real quick I bent over and licked from his balls all along the underside to the head, and swirled my tongue around it. I took the head in my mouth and proceeded to see how much of his dick I could get in there... aaaand Ben's cock is so big I couldn't get my mouth around it. I felt defeated-- first the height difference made it impossible to fuck my ass in the shower and now I couldn't get my mouth to open wide enough to deep throat him. It was depressing.

In a few minutes he was piledriving into my pussy, taking my mind off our size differences- although occasionally I did have to let him know that those ribs he was laying on could possibly break and shit. My feet touched the headboard several times and it felt fucking great.

So my nipples are really sensitive, which Ben uses to his advantage. He had one sucked into his mouth, flicking the other one with his finger, and I have that bdsm thing where pain is pleasure to me, so I would gasp and tighten my pussy every time he flicked it hard- and he pulled away, still fucking me, and told me to play with the little man- nipple sticking out from his pecs. Okay, I put my mouth on him and licked and sucked, making him moan in pleasure... then I took my mouth off and twisted it. He yelped, so I put my mouth back and licked and sucked him some more, until I heard the happy moans... and I stretched his nipple out between my fingers, and twisted it even harder. Silence this time. I stroked his chest, trailing my nails across his skin- back and forth, up and down, his skin quivering when I touched him. My hand stroked his neck while he moved his head up, eyes closed in pure bliss- and my hand tightened around his throat. He didn't pull away and I could feel his pulse quicken. "Oh, you LIKE that, DON'T you" I absolutely purred, not loosening my grip. His dick was rock hard and he whispered "Yes..."

I pulled away from him and stood up. "Get on your knees. Here " I patted the foot of the bed.

Ben stood, erect cock waving in front of him... moved to the foot of the bed and knelt there in silence. His eyes were closed and his hands were at his sides. I went into the next room, to my Big Bin O' every sex toy ever invented... and came back wearing my biggest strapon, the same one he used on me when we first fucked. I gently pushed him forward until he was on all fours.

Ben is bisexual, verse, and told me only guys with very small cocks can fuck him because his ass will not let in a bigger cock. He pushed his face into the bed while I lubed up his asshole and penetrated him with a finger. I stretched him inside, gently, while stroking his back and ass. He gasped when a second finger went in, but I continued to open him slowly and sensually. I manually stretched him until I felt his sphincter loosen.

I let him feel the big glans of my strapon cock at the entrance to his ass-- and then I entered him.

Ben whimpered, and I knew that I knew. I'm a Switch, and have always known that pain can turn into unbearable pleasures. I know that whimper... and now I would initiate my lover into that secret world.

I could feel my cock opening him inside. When about 4 inches were inside him, I began to move in and out, each time going in a little further. His eyes were still closed and each time I went a little deeper into him, he said "Oh." It took several minutes of slow movements before my cock was all the way in his ass. He shuddered so I stroked his back and his ass and his powerful, muscled legs. I gently fondled his balls and I stroked his hard cock as it hung between his legs. I took my time.

And then I fucked him, the way men fuck when they intend to dominate: I fucked him hard, deep, not intending to stop until I felt him submit, until I felt his body shake with the feelings I pulled out of him, until he realized he wanted to feel this again and again. I made 4 or 5 shallow thrusts, then went deep into him. My cock opened every inch of his tight ass, pulled all the way out, drove back deep into him, pulled out again, and drove into him again. Every stroke he said "Oh." Oh. Oh. Oh. I leaned over and told him "Good boy" as my cock relentlessly destroyed his ass. "Do you want me to stop?" He moaned "No, oh god" as leather slapped against his balls. He was now making a nonstop wail- oh god, oh god, please please ohhh- and I saw his dick twitch and jerk when he came. His whole body was shaking and as I withdrew my cock, he collapsed on the bed. I left and came back with a washcloth but he was already curled on my bed, eyes closed, falling asleep. Oh, Ben, you're just like me. You will crave this feeling, the pain that brings out the submission that you need like you need the oxygen you breathe.

Ben slept like a baby for two hours and I was laying next to him when he woke up. He stretched and yawned as his hand reached for my mound: his finger penetrated me, I gasped out loud, his dick revived to hit his belly again, and he fucked my brains out for an hour. His pinned me to the bed, sliding his big cock up my ass and finished by putting my legs up on the headboard again. Several times. I was so aroused that a single stroke of his cock made me cum.

He didn't mention me pegging him, but he will. I know how this rodeo starts and how to show him how it works. He snarfed down a couple of chili dogs and I drove him to his train station while he yawned the whole time. Oh, how fascinating it will be to see where this goes. My good boy, my lover, let me show you around my side of town.