tagFetishDiane Milking Sean Ch. 01

Diane Milking Sean Ch. 01

bystacey_lynne©

Frankly, I have lost interest in sexual intercourse. For that matter, ditto for blow jobs, hand jobs, foot jobs, etc. Please, don't get me wrong. It's not that I dislike sex. Quite to the contrary: I enjoy fucking a woman just as much as the guy [or gal] next door! The change is that Diane – lovely Diane – has milked my prostate and the ensuing orgasms are unparalleled in their whole-body, deep-throbbing, long-lasting effects!

Meeting Diane

It's been a week form hell at work, long hours and intense concentration to detail draining me of all energy. The proposal is finally finished and I rush to the airport to catch the very last flight, hoping to make it to my presentation early next morning. Such was my exhaustion that the instant I sat down and buckled my seatbelt I fell sound asleep. I don't remember anything during that long flight. I wake up groggily when the pilot makes the announcement of our approach. Such is my confusion that for a while I have no idea where I am, much less what I'm doing. My head is leaning upon a woman's shoulder. My hand is resting high up on her thigh, practically at her crotch.

Embarrassed, I straighten up and mumble some sort of apology, "I must have fallen asleep."

The woman smiles very sweetly, "Indeed: when I came to take my seat, you were already sound asleep. And you didn't stir all flight long!"

My next thought of course is to take away my hand. Her thighs are firm and I think I can feel she is quite moist between her legs. Very unaccustomed to this kind of situation, I slide my hand very slowly away. She turns away from me, looks out the window, and nonchalantly replaces my hand where it was. Maybe even a bit closer to her crotch, but I am not sure.

Not a word passes between us as the plane taxis to the gate and we disembark. She smiles ever so sweetly, "Do you have a car?"

My answer is as tentative as it is cautious. "I am here on a business trip. I will be renting a car, heading to my hotel, and getting a good night's rest. Big day tomorrow."

She puts her arm around my waist, cheerfully walking alongside me, "In that case, I will let you drive me home. I was planning to get a cab, but given the late hour I feel a lot safer with you. Besides. It's on the way downtown: you can drop me off, if you prefer."

Somehow I felt very much at ease with her, her cheerful disposition, business executive manners, and suave Southern accent. Walking briskly alongside me, maybe even a step or two head, she exuded self-confidence and tremendous energy. I felt good with her.

Picking up the car at the rental place, we drove away. Once on the highway, she smiled as she told me which highway to take, turned on the radio, and unzipped my trousers. Just like that! Simply and efficiently unzipped my trousers like it was the most natural, common thing to do!

Her fingertips started to play with the head of my cock. She was gentle, consistent, and deliberate in what she was doing. I could sense she was good, very good at this. I moaned and said something like, "It feels so good!"

She turned to look at me and smiled, "It's the least I could do. After all, you made me cum two or three times during the flight while you were sleeping and touching me!"

Whatever. The right thing or not to touch a woman on an airplane was irrelevant now. All that mattered is that she was stroking my cock. A good, strong erection in the hands of an expert woman: what more could a man ask for?

Bathing with Diane

We got off the highway and she asked me to stop at the drugstore. I walked in with her. She went straight to the back, picked up a bottle of baby oil, and walked back to the checkout. She glanced back at me and caught me eyeing the condoms. She laughed, "Oh, don't bother. You won't need those tonight!"

Well, so much for that fantasy. Even my erection subsided. I continued to drive, now in confused silence.

Her house, about half an hour's drive from the airport, turned out to be quite some house: big, with a sprawling lawn, large windows, and a long driveway. I drove up, got out to take her carry-on out of the trunk and walked her to the door.

She smiled, "Get your things, too. It'll save you half an hour's drive into town, you can get a good night's rest and breakfast here, and be out early tomorrow morning. Your meeting is in this general area anyways. It'll save you time and money!"

Naïve and silly that I am I still did not know what to do. Meekly I followed her inside, up the stairs and into a large bedroom. Pictures everywhere told me she was married with children. Yet she was so casual about everything! I looked at a family picture on the dresser. She saw me staring and smiled. "That's Joel and me last summer, and these are our kids, J W and Samantha."

I was still quite confused but she went on as if nothing. Taking off her blouse and skirt, she lay them neatly on the chair. "Come!"

I followed her into the bathroom. She sat on the toilet, parted her legs a bit, raised her heels on tiptoes, and started to pee. Very noisily, too. She looked up at me and smiled again, "On the plane I couldn't get up because I was afraid I'd wake you."

There she was, peeing away noisily, happy and smiling. She sighed. Taking off her panties, she handed them to me. "Please be a sweetheart and hand-wash them. The sink is right there. Use warm water and hand soap."

"Men handle women's panties like women handle a loaded gun."

Whoever said it must have been looking at me. Those panties felt so delicate, so frail, so soft in my hands. As I let the warm water run, I could sniff her femininity and almost even feel her warmth. Hand washing her panties was the single most erotic thing I had done to date!

But there was little time to waste on her panties. She had already stepped into the shower and was calling me to join her. Eagerly I too undressed and stepped in. For the first time all night I noticed exactly what her body was like. She stood about 6 feet 2 inches (I know because she was about two inches taller than my six feet), very lean and tight-bodied, toned muscles, and a flat tummy. Her breasts, maybe a 32 A or so (what do I know, except that she was small-titted) were capped with very perky nipples. For a woman with children about my age, she was in remarkable shape. Better than most women I know, actually.

Her hands were already starting to lather my body. All along she was chatting and laughing as if we had been together for ages. It was all so natural and so casually intimate! She lathered my torso and back. If she was intrigued by the three deep scars on my back, she did not say a word, except that I know she skirted them carefully.

Soon she was kneeling next to my thighs.

She slipped her soapy thumb deep into my ass!


Just like that! And she continued lathering my thighs and calves and feet, with her thumb deep into my ass! It felt so good!

Her hand rode up to my balls and she lathered them, maybe a bit longer than necessary merely for hygienic needs. Her thumb came out of my ass. I moaned, genuinely sorry. With one hand she held my seven-inch cock and pulled my foreskin back as far as she could. And then just a bit more. The other hand lathered my cock head, her eyes at the same level. I could tell she was noticing everything about me.

She stood up and handed me the soap. I did the same to her, lathering her back. She turned and now I had no choice but to lather her breasts. She smiled a lot at me. I could feel her nipples' hardness and the fullness of small breasts in my hands. I worked my way down. She was relaxed and comfy. Here was a woman with very abundant black hair and blue eyes, and of all things, she did not shave her pussy. It too was thickly matted, just like her head.

Following her lead, I knelt and lathered her legs. Moving up, I dared. Slipping my thumb up her ass was the very first time I had ever fingered a woman's ass. It felt so good! She parted her legs a bit, as if to ease my entry. Once my thumb was deep inside, she moved the right leg off to a side, turned out it a bit, and lifted her heel. In this position I noticed my finger could slide in another fraction of an inch up her ass. She really knew this stuff well!

When my other hand started to lather her pussy, she looked down at me, smiled, and opened her labia for me. Amidst all that thick hair I could make out the slender lines of thin labia and what must be an even tinier clitoris. But I did not find out. She smiled, nudged me to get up, my thumb came out her ass, and we rinsed.

Opening up for Diane

We toweled off and I noticed she was all smiles and happiness. Casually she told me to rinse her panties that were still in the sink and hang them to dry. While we brushed our teeth, she asked me to put the bottle of baby oil we had just bought under running warm water.

She leads me to her bedroom. I am not sure exactly what I am supposed to do. All I know is that my hormones are racing and my testosterone levels are sky-high. But she is quite in control here and somehow I feel good in her presence.

She tells me to kneel at the bedside. Placing a towel under my legs, she tells me to spread my knees far apart. My chest is on the bed. She places a soft and fluffy pillow under my head. I feel so aroused! A constant stream of pre-cum is oozing out. It feels so very good!

She is at my side, caressing my ass, chatting away, caressing my ass some more, laughing every so often. For the longest time she caresses every part of my ass. Sometimes she uses both her hands to spread my cheeks wide. She relaxes them completely. I keep looking at her. She is so beautiful! Black hair, blue eyes, soft skin, small breasts, tall, slender body, long fingers, muscular hands – she is perfect!

She laughs and kisses my mouth very lightly. She stands. She walks around and sits on the floor right behind me. My ass is at her eye level. I feel so totally exposed and vulnerable – and yet so totally at ease – and at the same time, sexually overdriven!

She pours warm baby oil down my crack. Slowly and abundantly. I feel it sliding down. When least expected, she approaches her finger to my ass. Without further ado, without any warning nor any announcement, she slides her finger easily past any resistance my sphincter should have offered. She just slid her finger deep up my ass!

Gently, methodically, expertly, she is fingering my ass with one hand. The other is sliding up and down my back. She knows what she's doing! In all the way, out almost all the way; in all the way, out almost all the way she is finger fucking my ass in the most glorious way I have ever felt!

I am vaguely aware that she has not touched my cock at all, even though it is inches away from her face and staring eyes. Somehow, it doesn't seem to matter, does it? But she senses my thoughts. "You have a beautiful cock, you know? I love how smooth and long and richly veined it is!"

I squirm a bit, hoping maybe-just-maybe her hand moves to my cock. She is too good at this. She laughs. Instead, she surprises me by quickly slipping TWO fingers up my ass. I try to lurch up, but she was already expecting this reaction and her other hand was on my back, keeping it down.

She let me get used to her TWO fingers up my ass.

Then she started.

The most perfect sexual sensation a man has ever had.

Sheer bliss!

Her TWO fingers found my prostate. Slowly, gently, expertly she massaged my prostate. I felt a wild urge to pee. Do to something. Nothing could happen. She had her thumb perfectly positioned to press against something in me that blocked any fluid from moving. And yet, she kept at it. TWO fingers deep up my ass massaging my prostate deeper and deeper, better and better. I knew she was staring at my cock throbbing wildly, savagely. I knew she was staring at my balls, just as desperate. She simply continued slowly with the prostate massage.

She was so adept!

Diane would slide her TWO fingers very slowly up my ass. When I thought she could go no further, she managed another push further in. She would slide them back out, just as slowly, almost all the way out, letting me feel the desperation of the ensuing emptiness. She would flare open her two fingers and slide them back in and back out, dilating my ass even further. At times, her TWO fingers would slide over my prostate, sending electrical storms up and down my entire body. Or else, on the way in or out her TWO fingers simply pushed up and away from my prostate, making me desperate for her touch.

Diane was at eye level with my ass. She could see everything she way doing to me and how my body was reacting. She was calm and poised. In her soft, sensuous voice she kept talking to me all along about anything and everything: how tight my ass was, how I was learning to relax, that I have a beautiful cock ("please, Diane, please, grab it and pump it"), about how she imagined I liked to fuck other women my age.

In addition to taking about my cock, Diane also made comments on how my balls looked so full and so firm. Did I masturbate very often? I admitted I did, hoping she could not see me blushing. Diane went on to say that it was very healthy for men my age to masturbate incessantly and keep my balls churning on overdrive. She said she was thrilled I was uncut and when she felt me shudder at that comment, she gripped my prostate even more fully, making me feel like a million dollars. Diane was good, really good at this!

She was perfect at sensing my reactions. Early on Diane had asked me if I was still an anal virgin. Sheepishly I had to confess I was. She seemed to have shuddered right at that moment, but I was too taken afar with her massaging. If I would contract my sphincter, Diane would slow down and stop, letting me relax before moving on again. If I dilated it too much, she would flare her TWO fingers open and gently pull them almost all the way out. Maybe she was looking INTO my ass?

Again and again I knew I was going to explode in a wild climax. But her thumb had me totally under her control. Her massage was intense, deep, complete. I was seeing stars, then entire galaxies. And yet, she would not release me. There was no way I could possibly hold off any longer. Either she let me climax or else I would spin around and shoot my load into her blue eyes!

For no reason, she suddenly stopped.

Her TWO fingers seemed to be gripping my prostate from within.

Her voice became very soft.

"My name is Diane."

And with that, she released her thumb.

A torrent of ejaculate shot of out my cock!

A torrent, a stream! Not a set of pulses and shots like I had always had before. No! This was like opening a hose and just letting it all out! I knew it was the strangest orgasm of my life. An entire load of semen shooting out of my cock. Not a single pulsation or contraction or any other forms of penile muscular reaction!

And I knew it had been a huge load. I had heard it splashing against the towel between my legs. And now I could smell its bittersweet scent.

I was drained.

Diane helped me up, limp as a wet rag that I was, and onto the bed. She cuddled me in her arms, as if I was an infant. She turned a bit and placed her nipple next to my mouth. Feebly, I protested, "It's MY turn to make YOU happy now."

She drew me closer to her and laughed, "But I've cum three times while I was milking you! It's my first time deflowering an anal virgin! Besides you haven't even told me your name. And now I need to breastfeed you. I've got to get up very early to got work out and you've got your presentation to make in the morning."

"Sean," I whispered coarsely.

And fell immediately asleep.

Again, next to her, twice in one day.

Twice during the night I woke up cuddled up in her arms, still with a throbbing erection. My fingers sort of slipped down to her hairy pussy but I was so tired I simply fell back to sleep.

Closing the deal – for Diane

The alarm clock went off around 6 am. I looked around and had no idea where I was. Slowly things came back. My erection was still as hard as the night before. Diane was nowhere to be seen. But I did not have time to waste. I showered, shaved, got dressed and made my way downstairs. The table was set, breakfast was served: freshly brewed, strong coffee, orange juice, toast, and fruit preserves.

Next to my plate, something strange. Something only a woman would do. Her panties, the same panties she had worn yesterday and that I had hand-washed last night, were there with a note in impeccable handwriting:

"Sean sweetie, you performed admirably last night.
I am so proud of you!
Here is a small token of thanks.
Softest kiss,
Diane"


Lazily I picked up her panties, smaller and more delicate than I had noticed them last night. She had even had the presence of mind to scent them a bit with her perfume!

I went to the presentation and clinched such a fantastic deal that the company president was in awe of my self-confidence. The customers were just as surprised at the size and scope of the deal. And the promised of an even larger one to come soon.

Only I knew – and probably somewhere in this huge city, Diane too – that I was wearing her panties throughout the entire day. The night before, Diane had milked my prostate and given me the most intense, powerful, long-lasting orgasm any man has ever felt. By cross-dressing into her panties, she had conveyed onto me her powers and sensuality.

Diane is perfect!

I will never have an orgasm like hers ever again. I know that for sure now!

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