tagFetishDiane Milking Sean Ch. 02

Diane Milking Sean Ch. 02


Needless to say Diane's panties became my most prized possession. Working all day, very successfully now, if I may brag, I looked forward every evening to come home, take our her panties, and masturbate. No matter what I did, how I did it, nor where I did it, the pleasure was never as intense as it had been when Diane had milked me.

The few girls I dated were just as sexually boring. We would fuck and I would have an climax. It was purely penile. There wasn't the full-body, total orgasm that Diane's milking have given me.

There was another concern that occupied my thoughts. Whenever I masturbated or fucked a girl, a few minutes after my climax my cock would go flaccid. The one time I had been with Diane, my erection had remained strong for hours thereafter!

I could not get Diane out of my head.


By pure chance I happened to have my physical examination a few weeks later. My usual doctor was out and instead an elderly woman was taking his place. I casually mentioned to her that a few weeks ago after sex, my erection had remained very strong for hours. She looked up very concerned, "How many hours?"

"Three or four, I think," I replied, adding hastily, "Anything I should be concerned about?"

She looked at me square in the eyes. "If it's four hours or more, go to the emergency room. What you may be having is Priapism. a potentially painful medical condition, in which the erect penis or clitoris does not return to its flaccid state, despite the absence of both physical and psychological stimulation, within four hours."

I was not sure what to do. On the one hand, I had felt really powerful with an erection that had lasted all night with Diane even after she had drained my entire body. On the other hand, the words "emergency room" scared me. What caused it?

The doctor went off on a tangent including sickle cell anemia, leukemia, etc etc blah blah blah. And she finally circled back, her white hair bobbing and a glimmer in her blue eyes, "Or neurovascular prostatal constriction. It's something so rare we learn about it in medical school but no one seems to know how to perform it!"

I thanked the elderly doctor for her patience and wisdom and walked out. I had a bounce in my step. Diane had performed – so naturally and effortlessly, as was her nature – that which medical doctors only read about but never learned how it was done. Or for that matter, if anyone ever did that! Diane did!

Such was my surprise when I got to my office that there was a message from the company president to head back to Diane's city for another huge deal. AND there was a strange letter in my mailbox. The handwriting was unequivocally Diane's. In blue ink on beige stationery with her monogram she was inviting me to a party at their home this coming Friday!

I had not contacted Diane since "The Night She Milked Me" because I knew she was married. And I had no idea Diane had my address. I thought she'd forgotten about me already!

My business trip was quickly arranged, allowing me to leave on a Friday afternoon, giving me time to spend the weekend in Diane's city and going to my business meetings early Monday morning. I was shaking like a leaf from that moment on through airport security through the flight through the car rental through the highway all the way to her house.

Diane's Party

It was late evening when I arrived and noticed a lot of cars parked outside. The door was open and I let myself in to a party that was already in progress. A tall, slender, intense, middle-age man greeted me, "Hi and welcome, I'm Joel."

This was not a plain-and-simple "Joel". This was Diane's husband, lord and master of this house, and I could tell by his eyes, demeanor and handshake that he was a powerful executive, probably a triathlon athlete, and refined gentleman.

"Hi, and thanks for having me over. I'm Sean."

He roared with laughter, my hand still in his grip. "Oh, so you're Sean that fell asleep on Diane throughout the flight!"

Cold sweat started to run down my spine. If this iron man knew what had happened, he looked like the kind of man that had ripped off the heads of his enemies before and would do it now to me. Here and now and with his bare hands.

Out of nowhere I heard a voice that made my knees buckle and heart stop. It was Diane running toward me, "Sean sweetie, I'm so happy you came! You didn't even RSVP!" She wrapped her arms around my neck and pressed me against her body. "Come, meet my friends!"

My erection was instantaneous! Like a conditioned response, my cock swelled up instantly. I felt a drop of pre-cum ooze out. Her hand holding mine, she led me to her various friends. All I could think of was that same hand deep up my ass. Her fingers seemed even stronger tonight, and that alone made my ass tighten up as I followed her around, meeting so-and-so, until she led me back to the bar and her husband.

Joel led me to the bar, poured two Scotches with a single, huge ice cube each, and offered me one. We clinked glasses and I did as he: sipped mine very slowly. As we started to talk, a lovely woman came up to us. She was about my age, say twenty-five or so, black hair, green eyes, and the same laughter as Diane. Her determination said she was Joel's daughter. Joel introduced us, "This is our daughter, Samantha. Samantha, this is Sean."

She shook my hand and laughed, "Oh, you're the Sean that fell asleep on Mommy's shoulder on the plane!"

Three things: Diane had told her husband and daughter, so I felt safe that they knew who I was; Samantha had long, slender fingers and a strong grip, and did Diane tell them she had milked my prostate?

No time to think: Samantha was taking me around, chatting away just as excited as her Mother, laughing and talking and holding my hand as if we had been together for years. A lady that said she was Diane's business partner asked me if I had the habit of falling asleep on stranger's shoulders. She winked and said it had been a clever move on my part!

My cock was throbbing inside my trousers. Even thinking about sitting on the plane, sound asleep, my head upon Diane's shoulders and my hand lazily between her thighs made me giddy. Samantha walked around and introduced me to even more interesting people.

One gentleman, Joel's golf and bear hunting buddy, asked me to join them on their next outing. It would be roughing it, but he knew I could handle it.

Another man owned a very prestigious gourmet academy that catered fine meals once a month for an exclusive dining society. Did I know how to cook? Well, I admitted I am a part-time chef. "Splendid! Diane and Joel will host the event next month and you'll be in charge!"

I met a guy, also about my age, tough as a rock. He was Diane and Joel's son, J W. Not an ounce of fat on him. Samantha led me away by the arm and confided that he was on a 48-hour leave from "over there" which I gathered was some special forces super-secret operation that I best not inquire too much.

My hormones were racing, my mind was swirling. From afar I caught a glimpse of Diane chatting with friends. She was laughing. My cock was throbbing for that laughter, the very same, generous laugh Diane had so cheerfully used when we had showered together, and again her laughter when she was talking while reaching deep into my ass and massage my prostate. I could not take my eyes off Diane. Samantha must have noticed it because she gripped my hand harder and whispered something like, " Mommy likes you – a lot."

I was feeling very much like part of the family and all Diane's friends were quickly accepting me as one of them.

Joel caught up with us. "Come, let me get you a refill!"

I protested that I'd best not since I had to drive back to my hotel later that night.

Joel laughed, "No way! Diane already prepared the guest room for you! Sean, young man, Diane said you're staying here with us every time you come to town!

My heart skipped a beat. Or many beats. Or I stopped breathing. Or my head rolled off. Whatever it was, Diane came up to me, put her arm around my and Samantha's waists and laughed how much fun it was to have all her friends over.

At that moment I was leaning against the bar. Diane turned away a bit. Her hip touched my erection. I felt it. She felt it; she must have felt it. Diane kept pressing her hip harder and harder against my erection. It was not a chance touch: Diane was deliberately teasing and arousing me wildly.

She turned and looked at me, smiling. Her baby blue eyes drove me wild with desire. These were the very same eyes that had stared deep up my ass when she had milked my prostate. These were the very same eyes that had stared and admired my cock when she had me on all fours, examining me with her eyes as her TWO fingers explored and exploited my ass. I tried to smile back but Diane was already waling away.

There was a pretty but very-stupid-looking girl all alone over there. I asked Samantha who she was. Samantha told me she was her brother's fiancée. She seemed so lost and so lonely I excused myself and walked over to her. "Hi, I'm Sean."

She looked at her feet and mumbled, "Yeah, I know, you're the one that fell asleep on Diane's shoulder."

Well, it sure seemed like the entire city knew THAT part of the story! But I felt sort of guilty with that lonely girl. "What do you do?"

Still looking at her feet she mumbled she was a high school drop out. When she had started dating Diane's son. Diane had helped her get her GED and straighten up her life. Now she was in grad school getting two masters' degrees at the same time."

I professed admiration – actually, I really did.

For once, she looked up at me, "Diane has a way of reaching deep into you and pulling out the best. If you know what I mean."

I nodded, "Yes, I do."

She walked away.

Yes, I do? What kind of idiot am I? Yes I know Diane reached deep into my ass, massaged my prostate, and milked me wildly! What on earth did Diane do to that woman? Or for that matter, to anyone and everyone at that party?

Two very gay men walked up to the bar and ordered the same I was having. One of them happened to brush his hand past my crotch. Feeling my powerful erection, he laughed, "My, my, my! Someone's going to have a nice time tonight!" and really placed his hand on my cock. I was at a total loss as to what to do and what to say. Samantha quickly replied, "And it looks like you're having a nice time, too?"

If Samantha had Diane's looks and wit, she also had Joel's strength of character. I looked around and saw Diane in the distance. Our eyes locked for and instant and she smiled. A few more drops of pre-cum flowed and my ass quivered.

Samantha and I continued to party, Joel served me a few more drinks and told me some very good jokes, the brother was quiet... everything went perfect until the guests left. I helped the family clean up. At one point when Diane and I were alone in the kitchen washing glasses she casually mentioned, "Your bottle of baby oil is in the cabinet in the guest bathroom. Please put it under running hot water before you go to bed tonight."

I was about to either leap out and grab Diane and kiss her or about to cum right then and there or to scream out to the entire world that I was the happiest man alive or let my balls explode or who knows what. Diane smiled and walked back out.


Everyone had left and everything was neat and in its place. We all said our good-nights and I walked to the guest room. What was I supposed to do? Well, for one, get the bottle of baby oil ("your bottle of baby oil", Diane had said) and put it under running hot water. My cock was throbbing so hard it was almost hurting. Let's put it this way: my balls were positively hurting so bad from the swelling and desire. I washed up, brushed my teeth, and went to bed.

Should I strip naked or not? Might as well. Diane already had seen me. She knew me. She had even looked deep up my ass already.

I undressed completely and lay on my back on the bed, dimming the lights. Hoping and praying and imagining.

A good twenty-five minutes later Diane walked in, more lovely than she had been all night, washed up and freshened, in a cute but simple nightgown. In her hand she had a very large crystal snifter with about half and inch of rich, dark cognac. She turned the lights all the way up. Asking me to part my legs wide, Diane knelt between my thighs. Her blue eyes were staring at my cock. It was throbbing. It was throbbing very hard. It was throbbing in thin air. Diane stared and stared right at it. She was smiling a lot. I tried to say something but Diane put her fingers on my lips, motioning she wanted to concentrate on my cock. I was ready, willing, and eager to leap up and fuck her brains out. But I knew better. I knew what Diane had in mind for me. For my ass. For my prostate. Or at least, I hoped. So I kept still and quiet.

A good while later, Diane looked up at me, "Sean darling, pull back your foreskin."

"Diane, I want you to do it. I want you to touch it."

Diane laughed, "Sean sweetie, you do as I say. Always. Is that clear?" And when I nodded, she continued "Good, now pull back your foreskin. All the way."

I did as best I could. Her blue eyes were staring, unblinking. She moved the lamp on the night table closer, shining right on my cock.

"Sean, darling, a bit more, please."

Now I was pulling back my foreskin past its natural limits. Diane seemed to know this and with her eyes motioned I should try just a bit more.

For the longest time, Diane stared at my exposed cock. Gently and slowly without taking her eyes off it, she reached over for the warm bottle of baby oil on the bed. Perfectly, like only Diane knows how to do, she opened the top and let one, single, just one droplet fall out. Perfectly and squarely. Smack on my dilated pee hole. Just like that! I felt its warmth flow down my urethra. Gosh, this woman really knew how to make a man feel like a stallion!


Softly, almost quietly, Diane asked me, "Assume the position."

Like the other night, I knelt at the bedside, my torso on the bed, knees on the floor, spread apart. I was trembling with desire and anxiety. Diane walked around back and forth, staring at me. She noticed my trembling and whispered, "I know, sweetie, I know. Relax, darling, do your best to relax. You're doing this for me. So I want you to relax and be good to me."

Her voice was soothing and I calmed down. She resumed her good mirth, talking and laughing while she caressed my ass, slapped it playfully from time to time, spreading my cheeks wide.

Diane knelt behind me and made herself comfortable. My ass was at her eye level. She poured warm baby oil down my crack and chatted away happily as I moaned with desire.

Diane started with just one finger, slowly, deliberately, without pause nor hesitation, ignoring any resistance my sphincter may have thought of offering. Sliding all the way in and almost all the way out, she slowly got my ass to widen. A good five minutes of this, while she chatted and laughed, TWO fingers were inside me, sliding effortlessly in and out. She soon found my prostate. TWO fingers massaging from inside!

If the first night all this had been a complete and total surprise, now it was sheer ecstasy. Maybe because I knew what to expect and was living the moment to its fullest. Or maybe because Diane knew me so well she could and was exploiting me to perfection.

All along, Diane chatted and laughed and made me feel sexually powerful.

She asked me if I continued to masturbate incessantly. I told her I did.

She asked me if I fantasized about her milking my prosate all the time. I admitted I did.

She asked me if I thought of her while I was fucking my girlfriend. Yes, I did.

Diane asked me if I enjoyed wearing her panties when I masturbated. I told her about cross-dressing in her panties for major business deals and when masturbating alone, always careful to hand-wash them gently in warm water and hand soap. She seemed to like that last line quite a bit because she moaned and did something very special to my prostate right then and there.

I gasped when I realized a different sensation. THREE fingers were inside my ass! Her thumb continued to press very firmly that particular spot so there was no way I could let even a single drop of anything flow out of my cock.

THREE fingers! Diane was massaging my prostate. She was clawing it from within. She was cradling it between her THREE fingers and squeezing it and pulsating it!

My cock was throbbing wildly! Diane was probably staring alternately at my cock and deep into my ass. She laughed, "Sean, you have such a lovely cock, darling!"

I tried to buck my pelvis, indicating I wanted her to stroke my cock. Diane was too good for my simple ploy. She simply slowed her tempo until I calmed down a bit.

Instead, she placed a srcunched pillow under my left knee. It was like I had a raised knee, somewhat akin to a dog peeing. And in that position, Diane was able to maneuverer her THREE fingers around to massage my prostate from the side. Sheer glory!

There was no way I could possibly ejaculate. Diane was playing with my insides and at the same time applied just the right pressure on just the perfect spot to keep me from squirting.

I heard her moan softly. Diane had told me the first night she had cum while massaging me. Now I knew for certain that she was cumming. I could sense her THREE fingers going totally wild inside me, flickering my prostate from all directions at once.

I was seeing stars and galaxies and black holes and novas and supernovas and Diane just kept going.

For no reason, she took the large crystal brandy snifter in her other hand. Without saying a word, without letting me know, without even preparing me for it, Diane released her thumb.

What a massive, uninterrupted, continuous ejaculation that was!

No pulsations, no contractions, nothing from any part of my body. Just a huge, long-lasting, interminable ejaculation!

I heard it shoot right into the snifter, like opening a water faucet wide open and shooting a torrent of water into it.

I was drained!

Physically, sexually, orgasmically, semenally... drained.

Diane helped me onto the bed. My legs were wobbly. My arms were limp. My face was motionless. Diane sat on the bed and held my head on her lap. I looked up and admired her blue eyes and smile again and again.

In spite of my massive orgasm, my cock was still throbbing hard.

I really wanted Diane to breastfeed me. My hands feebly went to her nightgown to exposer her tiny titties and hard nipples. Diane let me fumble a bit, smiling as always. Instead, she brought the snifter to my lips. Gently, lovingly she poured that bizarre cocktail of rich, dark cognac and my creamy, bittersweet ejaculate into my mouth. I knew what she wanted. Slowly she poured it into my mouth. Just as slowly I savored myself and swallowed.

When it was all finished, she smiled, arose, and helped me lie back flat. Standing at the bedside, she wished me a good night.

I looked at Diane. Perfect, beautiful, expert milkmaid.

My cock was still throbbing hard, harder than before, I think.

For no reason, very quietly she took off her panties. Rose-colored, very lacy, very feminine. She touched my thighs. I knew what she wanted. I raised my legs a bit and she slipped her panties on me. I raised my hips a bit and soon I was wearing her rosy, lacy, panties that exuded her exquisite femininity.

Diane walked away, turning off the lights on the way out and closing the door behind her.

My cock continued its hard throbbing.

And hour passed and I had not fallen asleep. Nor had my cock gone flaccid.

In sexual desperation – and maybe the mixture of too many Scotches plus the cocktail of cognac and my semen – I took a brave step. Getting out of bed, I tiptoed to Samantha's room. Trying the door, I found it unlocked. As quietly as I could, I tiptoed in, and super quietly slipped into bed with her.

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