Chapter 17: A Date With Winnie

Before I reached my place it occurred to me that I hadn’t even called Winnie in over a week and did so, recalling the special items we had purchased on our sexual shopping spree the last time they were together.

“Hello?” Her voice had a tremor in it. I realized she knew it was me calling and so got right to it, not bothering with formalities. “Get your ass over to my place; and be ready for me.”

“Oh god, Donnie I didn’t think you were ever gonna call me again,” she said in a syrupy voice.

“Did you hear me?”

“Yes--yes, I did!” He imagined her signaling Evie of his call and how the other girl had hurried over to listen in.

Despite his tone, Winnie continued talking about her and Evie. “Oh ... well because of me and Evie doing all those things ... you know?”

“You thought that displeased me?” I said, relenting somewhat, realizing she was overly concerned about nothing.

“Yeah ... didn’t it?”

“Not at all, Winnie; in fact I found the two of you very interesting. Very interesting, and I especially want to see you again.”

Let me give you my address, in case you don’t have it, or can’t find it.”

“Oh, I know it!” she said excitedly, and recited it for me then and there.

. Can you be here in an hour?”

“You can’t pick me up in that nice car?” she said plaintively.

“No,” Donnie replied with a finality that shook her confidence so much that she began to stammer and promised to be there within the hour.

“You’re not listening to me, Winnie. I said be here within the hour. That means ... since it’s now exactly four ten that you be at my door at exactly five. Not before, and certainly not after.”

“Your door at five...” Only then did Winnie realize she was holding a line that had gone dead at the other end.

In her apartment, Winnie held the phone in her hand thinking about the last time she’d seen him, his hand in her hair; his body on hers. There was something that pushed the moments spent with him to hyper reality. The way he half-closed the red curtains in her place and made the light from the street glow crimson on the white walls.

Truth be told, Winnie didn’t even really like him. That’s not to say she wasn’t already wet by the time she put the phone down. She hadn’t seen or heard from him in almost two weeks and yet he was constantly in her thoughts--and prayers.

All right, she liked him well enough. He made her do things she didn’t want to do, but all the same she loved the results. God, he’d found spots she hadn’t know existed and they were part of her. And he was generous ... wining and dining her ... buying her things--ohhhh, like those tight pants she loved putting on and then taking off--with difficulty, but she’d gotten off twice that way, and he wasn’t even around to see it.

He was a good listener too, and he was the best she’d ever known or even heard of as a lover. Okay, he made her do weird things ... mmmm, dirty things ... maybe she craved them too, but he was the instigator. No, face it girl, you need him doing those things to you, and you know it!

Jesus, look at me! I’m diddling myself! Better stop--well maybe another couple times and I’ll cum--maybe he’ll know--better stop before that happens. He’ll be calling me a slut and spanking me ... Ohhh Christ ... I’m gonna cum!

Donnie watched from a second floor window as Winnie drove up and parked in his driveway. He smiled approvingly at her attire—a white stretchy top; he couldn’t define it, but knew he’d seen something like it before ... then it hit him, his sister’s had both worn them--it was a leotard of sorts and she’d added a short black skirt that made for a startling contrast on her olive skin. She’d also worn sensible black shoes and not heels.

It was precisely five when she rang the doorbell. Donnie opened the door and told her to come in and sit down in a chair that had been placed in the center of the living room.

Winnie did so without a word, and then waited.

“I like you Winnie, I really do. Evie’s all right, but I like you. Do you understand?

“Yes, I do. I like you too, Donnie, very much.” Her hands were clasped and placed in her lap. Her eyes never left his. He discerned a slight trembling in her hands and thought that if she were standing her knees might very well be shaking. It was quite obvious that Winnie was frightened or nervous or both.

“I have a special treat for you tonight, Winnie.”

“Oh?”

“Yes ... a special treat, and mind you it doesn’t involve pain, but does entail a great deal of pleasure. Are you up for it?”

“Yes ... yes, master.”

“Am I correct in that you’re wearing a leotard?”

“Yes, you are.”

“Good. Now please take off your skirt and shoes.”

Winnie complied without a word then stood there before him awaiting his next order.

“It suits you, Winnie. In fact it looks stunning on that nice supple body of yours.”

A series of electric pulses shot through Winnie’s sex and left her nipples tingling and erect. Donnie took note and smiled.

“Is it too cold in here, Winnie?”

“N—no--No it’s fine.”

“I see your nipples are at attention ... I just thought...” He left it there.

“Umm, you know...” She began and stopped.

“I think I do know. Did you get wet when I called?”

“Yes.” There was no hesitation before she answered.

He smiled again.

“Would you like to know what I’ve got planned for us?”

“You ... umm, you don’t have to tell me. It could be a surprise,” she said, clenching and unclenching her fists.

“Why don’t we go into the master bath, then and get started?”

“You want me to piss myself? I can ... I didn’t go after you called.”

This was a reference to their last time together when he’d had her do exactly that after taking her shopping.

“No that won’t be necessary, Winnie. If you need to please relieve yourself and let me know when you’re ready. I’ll let you have your privacy, and wait in the bedroom. Oh, don’t worry about the table in the master bath. It’s for us, but take care of business first. Go on, that’s a good girl,” he said ushering her toward the master bath.

He listened to the stream of urine splashing into the toilet water, and the flushing sound that quickly followed.

“Um, I’m ready, Master,” she called softly, and he joined her in the bathroom to find her looking quizzically at the table standing next to the Jacuzzi.

“Just so you know what’s coming ... I’m going to give you a pussy massage. I read about it the other day and it seemed the right reward for you’re being such a good girl while I was gone.”

A perplexed expression appeared on her face. “Oh, you thought we were going to fuck ... well, we may get around to it, but first I thought this would warm you up.”

“Yes, Master, should I get up on that... ?”

“Please do--on your back, please.”

Once she had settled into the proper position I poured some warm oil into my palms and slid my fingers over Winnie’s neck and shoulders, molding the muscles, coaxing them to relax. I continued working her flesh, rubbing, squeezing and stroking the warm oil over her leotard and skin without really noticing the difference. I began rubbing a liberal amount into the material covering her breasts. “Don’t worry about the leotard, you can wash it after we’re finished,” I whispered.

“I ... I can take it off if that’s...”

“No, I want it on,” I said, overruling her.

“Oh, okay,” she replied and let her arms drop to her sides.

The white material became translucent with the application of massage oil. Her nipples, still hard pointed straight up, her areolas, now pebbled were complexly visible to my eyes. Winnie couldn’t see this at that point, but without a doubt knew how hard her nipples were as my palms roamed softly over her breasts until hearing her first moan of satisfaction.

Then leaving one hand massaging her breasts I sent the other to her pudenda and with fingertips pointed directly at her sex lightly ran then up and down from what I took to be her opening to the point I assumed her clit to be hiding.

Winnie’s hips jerked upward.

“Easy girl, it’s only the beginning,” I said softly.

“Ohhhh, jeez ... that felt...”

“I bet this is even better,” I whispered, inserting the tip of my index finger into the white material and forcing it into her vagina about half an inch. A low, guttural groan escaped her as I pulled back then pushed in several times in a row.

Not wanting to stay overly long in any one place for the moment, I left her mons and ran both hands over the actual flesh of her buttocks. You must know how pleasurable it is to have your ass rubbed, it is most enjoyable to be sure; and the fact that most young dancers today spend a great deal of time ‘humping’ their respective partners without repercussion of inappropriate touching would appear to prove the point.

Next I went right to her nipples, lightly swatting them both with my thumbs.

“Christ, Donnie ... I don’t know if I...”

“You can take as much of this as I give you, Winnie. Just relax and enjoy it, okay?”

“Yes, Master. I’ll certainly try. It’s almost overwhelming, you know?”

“You’re tits seem to like it, don’t they? Can you see them?”

“Umm, no, I can’t, but maybe if I stretch my neck some.”

“Please do so.”

“Ohhh, my God ... I don’t think they’ve ever been so big!”

“I could lengthen them out with some clamps I have,” I offered.

“Oh, no ... this is fine. No, this is wonderful!”

I spent a minute or so pulling and plucking on them through the material, which had a silky feel to it from the oil. “Let’s see what’s doing down below, shall we?” I said and heard her groan with excitement. This time I stretched the material at her crotch to one side, revealing her cunt to my eyes.

The labia were already swollen and her juices seeping out to lubricate them.

“You have the loveliest cunt, have I ever mentioned that before?’

“Not in those words, Master.”

“Well you do,” I told her as I spread her labia apart and peered into the coral succulence of her vaginal entrance as she gave out a soft sigh. With age old feminine subtly Winnie lifted her pelvis as if to reposition from lying in the one spot all the time. When she rested back down, it was clear that her legs were now further apart, providing me with even greater access.

I obliged her, running my middle finger the length of her slit, this time without the leotard’s skimpy material between her flesh and mine. And this time I discerned her clit emerging from its hooded hiding place and circled it without actually touching it. Winnie’s breathing became more rapid and shallow until she crowed, “Ohhhhhmmmmyessssss!” And then spread her legs even wider in complete invitation.

By this time my own cock was raging hard. I rubbed it through my pants and felt the cool wetness of pre-cum leaking out onto the skin of my stomach.

But Winnie came first--that was the plan and I intended to follow it to conclusion. I allowed the tips of my fingers to nudge the clitoral end of her pussy. Moments later I let the edge of my palm brush back and forth along the edge of her mound. Her breathing continued to quicken, was then drawn in and held briefly before being released in a long slow moan, as her body tensed and relaxed, her pelvis arching to meet the downward sweep of my palm.

There was now a constant to and fro motion against her cunt and I could now feel as well as see the wetness that was being massaged out from between her lips.

“Now, roll over on your side,” I said softly and she quickly did so. Then, with one finger jabbing lightly into her cunt, I began tracing small circles around her asshole with the fingers of my other hand.

“Ohhhh ... please!’ Winnie pleaded.

“What is it?” I teased.

“Fuck me! Please ... fuck me!”

“Who’s in charge here, Winnie?”

“Umm, you are ... but...”

I shushed her and went on with the massage, working her both holes while spreading then closing her buttocks, and then spreading them again with Winnie now moaning non-stop.

“On your back, please,” I said in due course, and of course, Winnie obliged as I turned away to get more oil.

From the corner of my eye I watched as she surreptitiously ran a finger between her legs then lifted it to her face and inspected it. She needn’t have done so as the trail of mucus was obvious. She wiped the finger on the sheet covering the massage table, then a little embarrassed that I would see her freely running cunt, she repositioned the leotard so that it covered her genitals completely.

Deciding to tease her without her realizing it at first, I moved to the head of the table and applied more oil to her breasts then spent several minutes massaging them and playing with her nipples.

“Like this?” I inquired.

“Mmmm, very, very much, Master,” she answered after a brief pause which I gathered was as a result of her dream-like state.

I traced circles of oil around each breast, this time running a trail directly across the nipples, causing an involuntary flinch from Winnie. I was careful to knead the peripheral tissue before paying any attention to the nipple. When each nipple had received the same attention I placed a hand on each gleaming teat and continued the massage.

Her nipples looked like they were ready to explode!

I slowly lifted my hands so that the fingers contracted towards the nipples. On reaching the nipples my thumbs, index and middle fingers closed around the base of each and gently drew them out. I repeated this several times and sensed Winnie was about to cum at any moment so I stopped.

She let out a sobbing moan and I couldn’t help but laugh. I immediately apologized to her for it really wasn’t a laughing matter, especially to poor Winnie.

In an attempt to prevent her climaxing, I asked: “Isn’t this preferable to being spanked?”

There was a long pause before she responded.

First she sniffed back another sob, and then she said haltingly, “N—no ... umm, yes—yes—yes! It is better!”

I was now facing her feet and began spreading more oil on her lower abdomen. My hands were working down the sides, then sweeping into the middle, regularly sliding a few inches short of her pubic bone which she automatically tilted toward me in hope that I would give it the attention she wanted. I made her wait for it, but eventually reached her pleasure palace once again. This time I allowed my fingers to slip under the edge of the leotard and graze her slippery lips. Somehow the material of the leotard had become firmly fixed in the crack of her ass. While I couldn’t see it at the moment it meant that her cunt was fully exposed as the material had to have bunched up on the front as well as the backside.

“Can you kneel for me?” I inquired, and Winnie quickly presented her ass to me while burying her face into the table.

A gentle almost unnoticeable tug exposed her starfish to my eyes, but I continued kneading her flesh, with a hand on each side of her buttock, rotating, drawing together, and the whole time exposing more of what lay below her anus...

I leaned forward and blew a little breath directly on her asshole. Winnie gave a little flinch and a stifled gasp escaped her lips.

“Oh God--Oh God!!” she said apologetically.

“Did you like it?” I asked.

“You know it, Donnie ... I mean Master.”

Her hand reached round my waist and brushed over my erection. “Mmm, I see you’re excited too,” she said in a low guttural tone.

“Mmm, yes I am. But we’ll get to that in a while. First I want to pay even more attention to you.”

“Oooooohh!”

Taking the bottle of oil I dribbled more across her cheeks, allowing a pool to form just at the top of her crack. As it overflowed and a trickle ran down over her anus I placed a finger on the patch of skin between her vagina and anus as if to stop the “accidental” flow. Winnie flinched and then groaned as my finger moved over her anus scooping up the excess oil but causing her sphincter to constrict involuntarily. Then I took a slickened cheek firmly in each hand and made several sweeps from the center outward, stretching her anus so that it opened considerably without benefit of my finger or cock.