This past week at work was a mess. One of my bosses decided to schedule me for a shift that I couldn’t possibly work without some outside help. Since the car accident, kitty’s been left without a car, so he uses mine to get to work. He works late; I work early. This works out! Thursday and Friday of last week, I had to work late. This didn’t work out! I had to arrange to get someone to drive 80 miles in one day to pick me up, take me to work, drop me off home, and then go back to where they lived, right next to work. I was not pleased. I don’t know why this person even agreed to help me out! But she did, and it was sweet of her. I bought her dinner and gave her gas money. She had to repeat the morning trip on Friday but Friday night I had covered.
Joey probably had no idea what he was getting himself into when I messaged him and asked if he’d be willing to pick me up from work, instead of meeting me at my house like usual. I explained that I worked a little ways out, but if he would do this for me, it would increase his rank in the Teh Bestest Pet Ever competition he didn’t previously know he was competing in. At first I think he was tentative. I guessed this because he asked me just how far out I worked. “Just follow the freeway you usually take to get to my house to the end.” To the end of what, I could hear him asking? “To the end of the freeway.” Joey is very, very expressive. Not always through words though. Usually just his deep, brown eyes. Via text, it comes out like this: O.O
“Best pet ever?” was what he asked in return and I knew he was hooked. It might have also had something to do with the fact that I mentioned pets that could offer service as well as their backside always got me revved up, and I wasn’t entirely lying about that either. Oh, and if he picked me up, we’d have to go get this flogger I was looking at. C’mon now, it was pay day.
Friday night, he came to hang out with me at work for a while. He drove me to the store to buy the new flogger that we’d played with together the time before last when we went to buy new lube for him. This is a beautiful flogger that I almost missed in the dark of the dungeon. I’d found a whip, one without a handle, that was designed to look like barbed wire. This pushed all the right buttons for me because when I was a little younger, I used to have fantasies of tying up boys in rough rope and barbed wire, but I just couldn’t find a good way to get barbed wire into the place without breaking SSC. Now that they’d made a leather alternate, I was hooked. I lashed him with this and the way he jumped and swore had me sold. Oh, but there was no handle. However was I going to work this? Just then, peering down into the darkness, on the next shelf, which was home to floggers, I found it: a suede flogger with falls of leather barbed wire in them. I snatched that baby up and Joey barely had time to turn around to offer his back to me before it fell upon him. The same reaction! Glorious!
Well now that it was pay day, I had to have it. And have it I would!
After that, we made our way back to my house. I knew I wanted to use that on him. I also knew that I couldn’t use just that on him or we wouldn’t each have a wonderful time. Tonight we’d do a proper warm-up.
Usually when he comes over, I give him time to get in the door. I don’t kiss him right off, because it’s too much like a relationship he’s said (although I’m beginning to think he can see how this all fits together) so instead I just let him join me in the living room and we talk for a bit. The dog (the real dog) is always super excited to see him and I think it’s best that he gets some attention first, if we want him to leave us alone at all while we’re playing.
Then comes the magic moment, when the dog winds down a bit, and Joey looks at me, waiting to see what I want to do. “Strip!”. It’s said with some enthusiasm, usually. Sometimes deadpan, but with a smile. It’s so entertaining to me because he is still so shy. He watches me when he can, but otherwise looks around to everything else in the living room while he casually pulls off his shirt and lowers his pants. It’s always the hesitation at the waistband of his underwear that makes me smile. I reassure him that I’ve seen him naked before and he laughs nervously. It doesn’t make it any easier this time around.
Tonight was different though. For one, he was standing on the other side of the room. I’d ignored him up until then, trying to get some music started so the neighbors didn’t hear the sounds of floggers. When he looked at me, I went straight for him. A kiss. There was no collar around his neck yet — it wasn’t part of the scene — but it appeared to be okay. I kissed him and helped him undress. It was as smooth as I can be, which really means it wasn’t smooth at all. I’m used to him taking his socks and shoes off when he gets in the door, tucking them under the coffee table where his furry bff can’t thieve his socks away for a vacation while we’re playing. I got all of his clothes off his body, had my fingers curling around his hard cock, and then realized my mistake. Oh well. He wasn’t shy undressing that time, and that was all that mattered.
In a matter of seconds he’d finished the job that I’d started and climbed onto the couch, kneeling away from me. I started with the old flogger, Old Trusty. I can swing and fling and flap and hit and thwap with that all night long. I can really get into it too. Usually I’m pretty good with it but he’d tell you there’s been one or two strikes to the side, completely unintentional. I wasn’t quite lined up right when I let go — premature flogging, due to excitement. Each time that I bring it out, I try to hit him harder and harder. He admitted once that part of him really wants me to hit him as hard as I can and the sane part of him is glad that I don’t. We’ll get there. I know this because I can see how far we’ve gone in such a short amount of time.
Caning is another favorite and while I usually tend to keep like toys together, which would have meant the new flogger would have come second, I didn’t think he was ready to go from thuddy to super stingy. I have a very thick cane that’s very thuddy and bamboo canes that are very stingy. I’m positive that they both got used. I’m positive that he did not get such a warm up for the bamboo canes. I can attest to this because there was more time spent sitting upright, breathing, then hunched over with his ass pushed out ready to accept another strike. So little effort; so much pain. I love these canes.
After that came the paddle. My paddle is beautiful. Thick, wooden, covered in sandpaper. It was frightening enough that pup, the construction worker, felt the need to point out the quality of the sandpaper and assure me that that was the real deal, this wasn’t fine grain to help save skin. Thanks pup! To anyone less experienced with sandpaper, it just hurts. I made sure that it hurt Friday night too.
Once I was done with the paddle, there was a crop. The crop is lovely because it makes the best smacking sounds ever when it connects with an ass. Especially a lovely ass that’s made to accommodate the size of the heart at the end. He’d jump when I hit him hard. He’d jump when he thought I was going to hit him hard. Friday night was all about pushing him and making him hurt. He’d mentioned that he thought I might make him bleed that night. I told him I hoped I would.
One major difference in the way we played Friday night was that I paid some special attention to his nipples, primarily by thwacking them with the bamboo cane and ensuring that they were rubbed by sandpaper. I remember him specifically pointing out later on that his nipples hurt while the rest of his body was mostly just a dull ache.
Finally we got to it: the new flogger. I tried to go light, I really did. It’s much heavier than Old Trusty though. I wasn’t quite used to the feel of it. I tried to swing it around behind him before I made contact but I was aroused. The first fall hurt him more than I was expecting but he put on his brave face for me. We have this agreement going that the less he says ‘fuck’ in normal circumstances, the happier I am. When I’m beating him, he can say ‘fuck’ all he wants and I don’t care. I think it’s hot, actually. Well, when this flogger came out to play, that was all I heard. Thwack, fuck, thwack, fuck. Amazing.
Afraid that he might not be able to handle it, I crawled up on the couch behind him, I pressed the handle of the flogger against his collared neck and pulled him back against my body. I told him ‘This is your one chance to get out of this if you want. You can ask me to stop right now, and I’ll put the flogger away.’ He swallowed, breathed for a second, and asked, ‘What do you want?’. I was thrilled. I was so turned on. ‘I want you to take more for me.’ So he nodded, I let him go, and I hit him more. To ensure that we didn’t go too far though, I made him answer in numbers. One a scale from one to five, one being my light strikes with Old Trusty and 5 being oh god, stop please, he was to let me know where he was at all times. I got a three, a four, and a lot of fucks. Never a five. We didn’t go for much longer though — I was too turned on.
I put the toys to rest. I had him climb down off the couch and kneel in front of me. I pet him for a moment, but then I remembered that my favorite toy was out to play. Reaching down, I began to stroke his cock. He knelt nicely, letting me play. He let me know when he was getting close. He’s never allowed to orgasm without permission. One of my favorite things about him is how sensitive the head of his cock is. Just touching it is an amazing experience for me. So I dragged my fingers over it, masturbating just that part of him, and watched with delight when he actually pulled his entire self away from me to get a moment’s reprise. When he was getting too close, we stopped.
Here’s where things go a little soft, a little vanilla. Picture some kissing, some rubbing, and a boy wearing a collar for me working to get me off in a new and exciting way for him that would probably elicit some yawns from the rest of us. Not that it mattered to me — I orgasmed.
After that, I pushed him back, had him sit at the corner of the couch, and told him to jerk off. In a matter of minutes he was riding the edge, fighting between doing what I told him to now (masturbate) and doing what I told him to always (don’t come until I tell him to). This is always an exciting game for me. He asked. He begged. I gave in way too easily, but he’d done me proud with all the pain he took. He came and I told him I loved the smell of it — like fresh rain.
After that, I took the boy out to eat so he wouldn’t starve to death. Waffles at midnight are a godsend. He made a bet, as we were both yawning, the he couldn’t stay up until 4am. What? Why would either of us agree to that? Because he shook my hand for so long that we were holding hands over the table in the middle of IHOP while not in a “relationship”, that’s why. I knew as soon as he got home and had constant stimulation he’d be able to make it. The wager? $10.
Needless to say, I lost the bet. Tonight I pay up. I have my own creative way of feeling better for losing though, which ties into service, which ties into “I Can’t Promise You the World”. Tune in later!
