Two (Part 2)

Two (Part 2)

The question, of course, was “what next?”

It took a couple of weeks before the right idea hit me. I was sure Amy was interested in sleeping with Allison (at least when she was turned on, which is the vast majority of the time), but I wasn’t certain what Allison wanted, if anything. Also, she was an important part of my little business, and I didn’t want to lose both a talented, trusted secretary and a friend.

But then the idea came, and all rationality evaporated.

I had to take a business trip to New York, and I would be out of town for four days. In my usual mad scramble to get out of the office and to the airport, I handed Allison my list of things that needed to get done while I was gone, like I always do. As we went over it, I threw a few more things into my briefcase. I headed for the door, then stopped, my hand on the door handle, my heart racing, and my cock hard in my boxers, trying to act like I had just thought of something. “Oh, one thing I forgot. Amy needs her weekly spanking. Thursday night. I wrote some instructions.”

I was rewarded with a very nice, deer-in-the-headlights look, her mouth hanging open. I smiled and winked at her, then handed her an envelope. Turning back to the door, I said, “Goodbye. And have fun.”

The letter in the envelope said:

Dearest Allison,

As you are perhaps aware, Amy gets quite moody and unhappy if she is not regularly disciplined. For this reason, she receives a thorough and rather hard spanking each Thursday night. Since I will be out of town, I would appreciate if you would administer this week’s discipline.

Feel free to ask Amy how the spankings generally go, but since she’s bound to fudge things, I’ll just tell you that she’s always completely nude for her punishments. I typically tie her hands behind her back with an old tie, and most of the time I blindfold her.

In appreciation for your assistance, she is yours for the night. Please do have fun with her—make her cook you dinner or give you a massage, etc. An important aspect of it all is to humble her a bit, so please find a few creative ways to accomplish this. And as you saw in my office recently, her bottom can take a quite a lot. And, frankly, a middle of the road spanking will not properly correct her behavior. Please be aware that she is very good at acting as if the spanking is about to kill her—do not fall for it. Be very thorough.

If, upon my return, I am not satisfied with the state of her bottom, I’m afraid your bottom will have to suffer for it first thing Monday morning. 

Enjoy,

S.H.

I didn’t tell Amy anything. She did have orders not to come while I was gone, but that was it. I had no idea if Allison would do it or not, but, man, did I hope.

I talked to Amy on the phone Wednesday night, but I didn’t say anything about Allison. Amy did not mention her either. All day my cock had been getting hard, begging for some relief, but I held back. During every boring part of each meeting, or when I was sitting around doing nothing, my mind instantly went to a great picture of Amy bent over my desk, up on her toes with her wonderful ass high in the air, with Allison, only wearing a dress shirt of mine, pulling back and cracking my soft, soft leather belt into Amy’s red ass. I don’t know where the image came from, but I liked it.

Thursday night, I hoped to hear something, but didn’t. My disappointment was growing. And my cock and mind continued the game of let’s-get-real-hard, oh-just-touch-it-a-little, no-we-should-wait-and-not-come. My blood was flowing pretty well by that point.

Friday night, I called home.

“Hello, love,” I said.

“Oh, hello, you wicked man.”

“Wicked, me?”

“You are very wicked. Allison called me yesterday.”

I chuckled. “Why would she do that?”

“She paddled my ass pretty good.”

“No, you goof. You’re supposed to tell it like a story. From the start. What did she say when she called?”

“She said that you had asked her to take care of our Thursday night ritual. I was clueless for a minute, but then she said ‘Your spanking,’ and it sent the biggest shiver down my spine. I was speechless.”

“Did you get wet?”

“I’m sure my panties were suddenly soaking.”

“What else did she say?”

“She said to be at her apartment at 8:00. I think I managed an Ok. Then she said goodbye, and that was it.”

“I bet you were turned on, like big time.”

“Oh, yes. And it scared me, which turned me on more.”

“Did you play with yourself?”

“No, of course not, you ordered me not to.” The sarcasm in her voice was pretty thick, but it would take me looking in her eyes and asking her to really know if she did or not. A spanking wasn’t exactly a deterrent, but then sometimes she would do everything exactly as asked.

“And how was yesterday, walking around thinking about Allison spanking you?”

“God, all day, that’s all that I could think about. I wasn’t worth a damn at work.”

“So were you on time?”

She laughed. “No. There was an accident. Traffic a mess at 8 at night. Who would have thought that? I was ten minutes late.”

“Were you nervous?”

“Like you wouldn’t believe. It took me a while to get out of the car. And I think my panties were soaked as I walked up to her apartment. She was waiting for me, and opened the door before I knocked. It was an awkward moment, but then she smiled and leaned in to give me a nice, warm kiss.” That made my cock hard, for like the 60th time in two days.

“What was she wearing?”

“It looked like her clothes from the office. A suit thing, with pinstripes. She looked good. She was having a glass of wine. I could taste it on her lips.”

“What did you wear?”

“I worked out after work, so I was in jeans and a T-shirt. A T-shirt of yours of course.” She liked how they smelled.

“She led me by the hand to the couch, and I noticed a hairbrush and some rope coiled on her coffee table. That’s when I knew she really was going to spank me. It was suddenly real, and I was scared and turned on. Just like the first time you spanked me.

“She said ‘So he spanks you every Thursday night?’ I told her you did. She asked a few questions, and then sort of out of nowhere, she said ‘Take off your clothes, Amy.’ I looked her in the eyes, and went to kiss her again (Amy’s normal stalling tactics), but she stopped me with a finger on my lips, and pointed me to the center of the room. I untied my shoes, and slipped them and my socks off. I was moving pretty slow–feeling vulnerable–and I could sense she was getting annoyed. I stood up, and pulled the T-shirt over my head. No bra, of course. She seemed to like looking at my breasts. I rubbed my nipples, smiling at her, still wanting that tongue. Then I slid my jeans off, turning around so she could take in the view. I looked at her, wanting her just to stick her tongue in me, but she motioned with her head for me to take off my panties. I wore the little, white ones you gave me. I turned around, and slowly slipped them down my legs, bending over for her as I did. She just drank me in for while, like she was going to eat me, as I stood there with goose bumps.”

Something must of changed in my breathing, because she asked, “Are you playing with yourself?”
“Just rubbing it a little. You?”

“Rubbing against the bed. On my stomach. What are you wearing?”

“My T-shirt and boxers.”

“Would you take them off for me? I like the idea of you laying there naked and stroking your cock.”

“It would be better with your mouth here.”

“Oh, yeah, it would.”

“What are you wearing?” I asked.

“Nothing. I got undressed, hoping you’d call.”

“Good girl. What happened next?”

“Hmm. Oh yeah. After staring at me for awhile, she stood up and walked around behind me. Ran her hand down my back and across my ass. She squeezed one cheek, and said, ‘You have a great body. I liked it when I saw it in the office.’ She turned my head and kissed me, her clothes pressed up against my back. It was really cool. Her mouth just seemed so awesome and delicate.

“She sat back down on the couch, and told me to light all the candles. She has candles everywhere–must have been thirty or forty of them. And she just watched as I lit each one. I felt very naked, her sitting there like that. It was very erotic, or something.

“When I was done, she had me turn off the lights and stand in front of her. She kissed me again, then blindfolded me with a scarf, and had me turn around. She tied my wrists together, behind me, very thoroughly, wrapping the rope around and around, almost up to my elbows.

“She pulled me down across her lap. She ran her hands over my ass. It felt great. My heart was thundering in my chest. Then she said, ‘Ops, I almost forgot. You’re supposed to kiss my feet.’ It was awkward–she sort of pushed me off her lap.

“On the floor, on my knees, I found her leg and kissed my way down. I kissed each foot, and waited for her to pull me back to her lap. ‘You can do much better than that, slavegirl.’ She pushed my head back down to the floor. I planted small kisses all over the top of one foot, moving around in circles. I licked her ankle, then kissed down to her toes. I started with her big one, sucking it into my mouth like it was your cock. I sucked on it, licking it with my tongue, and heard her sigh. Then moved to the next. When I had sucked all of them, I started with the little one and the next one–what do you call that one?”

“The ring toe? Who cares?” My voice was a whisper.

She chuckled. “Then, two at a time, I worked my way back up to her big toe.”

“Did it turn you on?”

“Yeah, it did. Mostly because she was making me do it. Then I did the same thing to the other foot. When I was done with the toes on her right foot, I start working my way up her leg. She stopped me when I got to her knee. ‘Time for your spanking, now.’

“I started to climb back into her lap, but she stopped me. She stood up, and I could hear her taking off her clothes. I could smell her, then. When she was done, she pulled me up onto her lap. I could feel her bare skin against mine. I was so turned on I was going crazy. Like the time you spanked me in the park, or when you took my ass for the first time.”

“So horny you’ll do anything.”

“Oh yeah.

“She ran one hand across my ass, and told me that she heard I was supposed to beg for it. I said, ‘Please spank me.’ She didn’t make me count them like you do. She just smacked one cheek, and then the other. Her hands felt tiny after yours. Sometimes five or six on one side, then she’s switch to the other. It didn’t hurt very much though, with just her hand. But I knew that hairbrush was still sitting there, and it looked mean.

“And it didn’t take her long before I felt her reach for it. She told me to arch my ass up for her, and asked me if I needed a hard spanking. I told her I did. She told me that your letter said you would spank her if she didn’t spank me hard enough. Then she laughed a little and said, ‘You’ll probably tell him I didn’t spank you very hard no matter how hard I spank you, won’t you? You’d like to see me over his desk, that belt whipping my ass, wouldn’t you?’ Fuck yes I would. I told her that I was going to tell you she barely spanked me, that she couldn’t resist my pussy. Then I lifted my ass up high, and asked her to spank me. To spank me hard. To make me pay for her going over your desk and taking your belt.

“She pushed my head down into the couch, to shut me up, and I think all her inhibitions where gone then, cause she let me have it. That damn hairbrush was hard, and it hurt, and I think she was both pissed off and turned on. Oh it hurt. She kept the one hand holding my head down, my ass all up in the air, and blistered it. Four or five on one cheek in a row, no time between them. And every time it would start to hurt too much and I’d squirm away or drop my butt, she’d just wait for me to put it back up in the air, telling me she it was costing me extra, but never saying how many.

“After I don’t know how many—maybe a 100 on each side–she stopped, and rubbed my cheeks. They were throbbing, and tears were running down my face.”

It’s a little disturbing, but her tears always turn me on. I like her to suck my cock with tears running down her face. And she knows it turns me on.

“She spread my cheeks, and ran a finger through my crack. She didn’t play with my pussy, though, like you do. God, did I want her to.

“She asked me if I liked to be spanked–if it turned me on. I embarrassingly told her it did. I asked her if she liked spanking me. She laughed.

“Then she started in on my ass again. I couldn’t believe it, but she gave me 30 or 40 more, just as hard as the first ones.”

“Is your ass still sore?”

”Yes, very. Bruised, too.

“Suddenly, she pushed me off her lap. Back on the floor, on my knees, she pushed me sideways onto my side, and then onto my back, my ass screaming from the carpet rubbing against it, and my hands trapped and uncomfortable underneath me, but she didn’t care. She grabbed my hair, and I could smell her up close then–she was above me, and I lifted my head up and suddenly found her pussy with my lips. She was so wet. ‘Put your tongue in me,’ she said. I pushed it in as far as I could as she pushed down, trapping me, grinding against me, as she pushed me further into her. My nose was rubbing her clit.”

“Did it turn you on to be tied up, helpless, as she fucked your face.”

“Fuck, did it ever. I think I almost came without anyone touching me.

“Then she pressed down even harder and she started shaking. It turned me on even more to make her come so hard, having her treat me as her toy. Knowing it was mostly from her spanking me.

“When she was finally done, she let go of me. I rolled on my side, to give my arms and my ass some relief, and I felt her move next to me. She kissed me, tasting herself on my lips. My face was so wet. She pushed off the blindfold, and looked into my eyes. She was kneeling next to me, looking down at me on the floor. Then she kissed me again.

“She moved down in front of me, so we were face to face, our nipples touching and bumping into each other. She licked and sucked them. We just made out like that, sometimes her leaning down to suck and nibble on my nipples, sometimes her feeding me hers, or her hands sliding around to rub my sore, sore ass.

In a bit of a different voice, Amy said, “She has beautiful tits. Bigger than mine. I really liked sucking on them. I bet you want to suck on Allison’s beautiful tits.”

“That wouldn’t be bad,” I said, “but a much bigger turn on will be watching you lick them.” It was clearly a dangerous area–Amy works out so much that she doesn’t have much body fat, and her breasts are not big, but they are so cute and perky. I always tell her they’re perfect, but she still has doubts. I’m not a complete idiot, so I said, “And her pussy. I want to watch you lick her pussy, with her tied up, and both of your asses red and striped. I want to watch you making her come like crazy on her tongue. Her tied up so she can’t get away from your tongue.”

Her voice went back to it’s low, turned on setting. “Eventually, she stood up. She mentioned something about her bed, but halfway out of the room, she stopped and looked at me. ‘I almost forgot. You were late. Naughty, naughty. I don’t like it when people are late.’ She was smiling at me with a really wicked smile. I felt like I was in trouble, cause my ass couldn’t take much more.

“So she ordered me to go get a yardstick from the kitchen. By this point, I needed to come so bad, but I went and got the yardstick, carrying it behind my back. It was not one of those light, flimsy ones, either. She had me stand in the middle of the room, and bend over, with my head on the coffee table. She wasn’t satisfied with that, so she made me spread my legs apart, then even further apart, tapping the insides of my calves and thighs with the yardstick. She even tapped it against my pussy, very lightly, then slowly harder, getting me high up on my toes.”

“I bet you liked that.”

“I could have come if she kept doing it, but instead she said, ‘I’m afraid that’s going to be 12 hard ones across your ass. These I want you to count. And, you will get extra if there’s any squirming, or anything other than that ass nice and high in the air. Is that clear?’ I said yes, ma’am, back to her, and the first one cracked into my ass. After the hairbrush, it hurt almost as much as when you zing me with the riding crop. It hurt.”

I almost said ‘wimp’, but I didn’t want to break her flow. I was pumping pretty good on my cock, but trying not to come until she did, or the end of the story.

“She made me ask for number two, and it zinged me right below the other one. She took her time and worked over my whole ass. Sometimes she would tap my pussy in between strokes, lifting me up higher on my toes. By eight or nine, my legs were shaking violently–I wasn’t sure I was going to make it and I wanted to please her and keep my ass high in the air for her, but I couldn’t stay up on my toes. She gave me three extras for that. I so wanted her to spank my pussy with her hand. She took me to the edge like you do, making me strain higher and higher to please her, with tears running down my face. I was crying when she was done.

“I wanted to go to my knees, but she said she wasn’t done with me. She leaned over me, her nipples against my back, and held me. The she started kissing down my spine, her hand playing with my ass. She was tracing the stripes with her fingers. My ass was so hot and sensitive it felt odd–painful, but so good. She must have knelt behind me, because she kissed each cheek, and started tracing the stripes with her tongue. Small kisses all over my ass, down my thighs, and into the little space between my ass and thighs near my pussy. She rubbed her hair over my ass. Then her fingers found my cunt and my clit. She kept kissing my hot, sore ass as she slid a finger in and started sliding it in and out while teasing my clit with the fingertips of her other hand. Then she licked the back of my cunt. Just tiny little licks, teasing me. Her nails felt cool on my clit. She would take her nails and lightly pull on my clit, and rub it between them. Fuck it felt good. Then, as I started to come, she starts licking my asshole, slipping her tongue in and out. I went nuts, thrusting back against her face, coming all over the place. Like you, she didn’t stop, just kept fingering me. She grabbed my wrists to keep me from getting away, then shoved two fingers in and just fucked me. I made a lot of noise.”

I mumbled an uh-huh into the phone.

“Eventually she let me ease down on my knees and kissed me again. She untied my wrists, rubbing them and kissing my fingers. Then I sat there and watched in a daze as she blew out the candles, all except one. She has an awesome body—I liked watching her.” Another dangerous moment, but I was close to coming and ignored it. “She grabbed the wine, and led me into the bedroom. We shared one glass–her holding the glass to my lips when it was my turn–in the almost dark, and then we started making out again. It was oddly romantic, sitting on a very sore ass, but with the one candle and the wine. So nice and slow, just lying there on our sides, pressed against each other. Her leg slid between mine, and we rubbed against each other and licked and kissed each other. It went on forever, sort of like we were in a haze. We both came once or twice–just awesome, little, cozy ones. It was just so different being with a chick, and us laying there and doing the same thing to each other at the same time. Sort of like when we do it when you’re behind me on our sides late at night, and we are both half asleep, and it’s just wonderfully close and nice. Sort of like that, but different.”

“So what happened next.”

“I woke up late for work, and had to rush home. She didn’t seem to be too worried about being late. Something about her boss being out of town.”

“Maybe I’ll have to spank her for that.”

“I would like to watch that.”

“You would? What else would you like to watch.”

“Are you stroking yourself?”

“Yes.”

“Are you close to coming?”

“Yes. Are you?”

“Yes. I’m on my stomach. My hand is underneath me. My ass still hurts from that damn yardstick.”

“We’ll have to get one of those.”

“So would you like to watch Allison and me together.”

“Yes.”

“Me licking her. Maybe she could lick me while you fucked me. Would you like to feel her tongue on your balls?” I could tell from her voice she was very turned on, and close to coming.

“Oh, yeah. I’m real close.”

“Come for me. I want to taste it on my tongue. To swallow it.”

“I wish your mouth was here for my cock. So my cock could fuck your sweet mouth.” I heard her suck in a deep breath, and let out a little moan, and then it was too much. Thinking about her bent over the coffee table and Allison with the yardstick. Thinking of her lying on her stomach, striped butt, humping her hand. Thinking of her blindfolded and tonguing Allison. I came hard, all over my stomach and chest, pumping it with long, long strokes, trying to empty my balls. All the tension and wicked thoughts from three days finally being released.

“I like listening to you come,” she said.

“Me, too. Did you come good?”

“Yeah, telling you about it was almost as good as doing it.”

“Hey, you’re not allowed to come until I get back. You’ll have to be punished.”

“I can’t wait.”