0 comments/ 163133 views/ 110 favorites Diane Milking Sean Ch. 01 By: stacey_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. 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. Priapism 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. Bedtime 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! Yes! 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. Diane Milking Sean Ch. 02 I lay perfectly still. Somehow, in her sleep she sensed my presence. She rolled over, still sound asleep, and put her arm under my neck, cuddling me in her arms. I guessed she must have inherited that instinct from her mother. Samantha pulled me closer. She was still sound asleep and I did not want to awaken her, risking the ensuing panic and screams of finding me in her bed. She brought me even closer. Samantha's breasts were much larger than Diane's; much fuller and much firmer. The most I dared was to stick out my tongue a bit to touch her nipple. She had a piercing! I must have shuddered at this discovery because Samantha moved a bit and rolled over to her side towards me. Her other hand lazily wandered down to my hips. I freaked out! I froze! What an idiot I am! In my desperation and stupor, I had forgotten to take off Diane's panties! Samantha's hand felt those rosy, lacy feminine panties on me. I wanted to rewind the clock! That was really stupid on my part! Samantha's eyes opened. Even in the dark I could see a sparkle. She smiled. Her hand reached down, moved crotch of the panties off to a side, and helped my still throbbing cock to leap out. She grabbed it really hard. She nestled me closer to her. And fell back sound asleep. I lay there without a muscle moving save for my cock throbbing, hard as ever, touching Samantha's perfect, unblemished skin, our bodies pressing together. By now I had learned: whenever Diane massaged my prostate and milked me, my cock would remain hard and throbbing for a good three hours. No matter how much she had made me ejaculate, I could still fuck non-stop for three hours! I thought back at what J W's girlfriend had said so mysteriously, "Diane has a way of reaching deep into people and extracting the very best out of them." Yes, indeed, that is exactly what Diane had done to and with me! For a good two hours I lie motionless. Diane had massaged my prostate expertly. Diane had milked me to perfection. I was wearing Diane's panties. Decision It was that night that I made my decision. Since I could not have Diane forever, I would make her my mother. Epilogue: two months later Diane Milking Sean Ch. 03 "Priapism is 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." Setting the rules: Sean A few months into the marriage I went to visit my daughter Samantha and her new husband, Sean. All was going very well in their marriage but a mother always needs to stop by and get a first-hand impression. They loved each other, both were quite successful, and of course, they spent a great deal of time together enjoying common interests. One evening after dinner -- and here it's my fault -- a little too much red wine Sean approached me as we were doing the dishes in the kitchen. With that silly smile of a male who's had a bit too much to drink and not enough sex that day, he asked, "So, Diane. Any chance of another massage anytime soon?" I spun around, looked at my son square in the eyes, and slapped his face as hard as I could. Standing a good two inches taller than his six feet, I glared into his eyes and told him in no uncertain terms, "You are a married man now. If I ever want to do it, I will order you. Otherwise, keep your thoughts to yourself and your prick for my daughter. Is that clear?" Reproached males have a dejected look, but Sean's was that of sheer terror. He rushed out of the kitchen and ran into their bedroom. Samantha looked quizzical and then apologized for her husband, "Sean's had a bit too much wine and he needs to get up early tomorrow to fly on a business trip." All night I felt terrible about the whole scene. Yes, maybe I had been to harsh on Sean, but then again a mother must set the rules of sexuality in the house. On the other hand, milking Sean's prostate had been a first for me, and having a man lose his anal virginity in my hands had been a momentous experience for me. It was almost dawn when I made up my mind: I was going to "make nice" with my son-in-law. Tiptoeing out of my room I went downstairs where Sean had left his suitcase by the door. Like a thief in the night, I opened it and right on top I placed the panties I had been wearing. Just like that: smack on top, still smelly from me. And with that, I went to sleep feeling a lot happier. Sean came back two nights later. Apparently his trip had been excellent and the deal he closed was enormous. Samantha and I were happy and we shared a nice meal together. After dinner I went for a walk with their huge dog. When I came back and went to my room to change for the night, I saw that Sean had already been there. Under my nightgown he had placed the panties I had given him. Only now they had been hand-washed in a scented soap. There was a little piece of paper with a simple line, "Thank you." I knew one of the reasons for his success was his secret cross-dressing in my panties I knew we had made peace. I knew he wanted me. I knew I wanted him. And I knew I had set the rule: it would be on my terms only. I flew back home the following afternoon. There was a lot to plan and it had to be done so carefully now! Setting the rules: Lisa Lisa had been dating my son while they were in college. Things cooled off a bit when he went on some super secret armed forces special unit who knows where. She remained loyal to him and now that he was back, they got married a few weeks after Samantha and Sean. The thing with Lisa is that she is ultra-shy and incredibly insecure. If my husband is to have a happy marriage and a successful life, I really need to get Lisa to wake up. Lisa is petite, standing at 5ft 2in, weighing a mere 110lb. She has small 32B breasts, and long blond highlighted hair. She is very fit, having been a gymnast for many years while in college here in Tennessee, and still keeping physically very active. A few weeks after my visit to Samantha and Sean, I flew off to spend a week with Johnny and Lisa. All seemed very harmonious with them. But there was something I saw in Lisa, something I had not detected before. It was a change in her expression. She looked different. She acted different. There was no other way I could describe it when I called my husband to report. Lisa was a cute little nymph! She avoided all talk about sex with me, blushing and running off to do something or other around the house. With Johnny it was next to impossible to get any information of any kind. But I knew like only a mother can know that Lisa's sex life was a bit different than I would have guessed when they first met. And I was determined to find out. It happened by sheer accident. One morning while they were both at work and my laptop battery died I ventured into the study and picked up her laptop. The history bar showed that the cute little nymph Lisa had been spending hours, days, and weeks reading erotica! That was all I needed. That afternoon when Lisa came home, I confronted her. She started to cry and said Johnny seemed to have lost sexual interest in her. And just now her own desires were starting to awaken. Sob, sob, sob. My arousal was getting more intense with every sob of hers. I held her close to me, a lot closer than a mother normally would, and told her that I was going to let her into the secrets women in our family passed on from generation to generation to keep our husbands interested, in line, and at home. But she would have to do what I said. She balked. All I had to do was to look down twelve inches, stare into her eyes, and whisper, "I set the rules in this family." She understood exactly what I meant. Good. Now I had both Sean and Lisa all to myself! Sean and Lisa look at each other The entire family came over to our house for a three-day weekend. My husband offered to take the two siblings, Johnny and Samantha, to visit his aging mother. Asking if we all wanted to go, I nicely pointed out that Sean and Lisa really had nothing to do with Nanna, and besides, too many people would confuse the old lady. My husband agreed. Saturday morning the three of them drove off for the day to see her. No sooner had they closed the door behind them and driven off, that I turned to Sean and Lisa, standing next to me in the foyer. "Take off your clothes. Now." I told Sean in a calm, cool voice. "Here, Mommy Diane?" he asked. My icy stare was enough for him to understand that yes, it was here. And now. He obeyed. His tall, slim body was a beauty to behold! The three, deep scars on his back gave him an added look of strength. I motioned him to turn around this way and that and he complied. His seven-inch uncut cock throbbing nicely in thin air made him look even more handsome than I remembered. Lisa too was staring. I turned to her very sweetly, "Sean is quite nice, don't you think?" Lisa stammered, "It's just that I've never seen another man except Johnny." I really was not expecting this at all! Lisa had only been with Johnny! No wonder she needed a lot of coaching and training and practice if she was going to have a happy marriage! Just as sweetly I asked her, "You too take off your clothes, Lisa." She stammered again, "It's that... it's that... it's that... Mommy Diane, it's that..." I was losing it with her, "Lisa, it's that WHAT?" "Mommy Diane, it's that Johnny is the only person that's even seen me without clothes." "Listen and listen carefully, Lisa. Either you take off ALL your clothes NOW, or else it's going to be a lot more people other than Sean and I that are going to see you stark naked today. Like all the bikers at the bar downtown." Lisa turned away from us. Trembling and quivering, she took of her blouse. Ever so meticulous, she folded it nicely and placed it on the floor very neatly. She wiggled out of her jeans. Same neatness in folding and putting down. Cotton panties with Snoopy on them. Cute but let's grow up, I was thinking to myself. Still with her back to us, her trembling hands were fumbling nervously with her bra snaps. And when she finally managed to get it un-snapped she seemed unsure what to do with it. I was losing my patience. Sean seemed frozen in time and space staring at her lily-white, petite body. She looked over her shoulder to me. I nodded. She and I knew what the question was. Her entire body was shaking like a leaf. Her legs were wobbly. She acted as if she had never taken off her panties before, first one trembling leg, then the other, a bit too careful not to lean over, doing everything possible to delay the inevitable. Finally! "Turn around, Lisa." Her right arm covered her meager breasts. Her left hand covered her pube. She turned slowly, eyes wide open like a fawn's at dawn. Sean was staring at her like the idiot males always are at this moment in time. I walked over to Lisa, stood behind her, and slapped her ass with an open palm, slapped her as hard and as a fully as I could slap her derrière. "Hands at your side, Lisa." "Yes, Mommy Diane." She had tears in her eyes. And now both Sean and Lisa knew that I meant what I said. And that any infraction of my wishes would be met with a vicious slap. Sean's face and Lisa's derrière had been the first for each. The first of many more to come and they both knew it. I let them both stand face to face, both with their hands at their sides, each looking and staring at the other. Sean's eyes raced up and down Lisa's petite figure, taking in her soft skin, her slender neck, her small breasts, her nipples darkening and perking up, her flat tummy and beyond as far as he could see. Lisa too was admiring Sean, mostly watching his cock. I could almost feel her pretty face bobbing up and down with every throb. I was giving them time and space to learn each other really well! The anal discovery I let them stand there while I went upstairs, fetched the bottle of baby oil, and brought it back down to put under running hot water in the kitchen. I took my time, calling Joel to make sure they were well on their way, that the road was free of snow, that they were looking forward to seeing Nanna, blah blah blah just to make sure I had the entire day to myself. When I came out of the kitchen and asked Sean and Lisa to the living room, I had the baby oil bottle with me, wrapped in a towel to keep it warm. Sean saw it and a smile came across his face. Lisa did not see the smile: her eyes were elsewhere. All she saw was a strong throb and a droplet of golden pre-cum ooze out. "Lisa, sit down next to me. Sean, masturbate." "Mommy Diane, how do you want me to..." "Sean, don't start on me. Pull back your foreskin. All the way. More, A bit more. Good, now hold it back with that hand. Use the other hand to pour baby oil on your cock. And let Lisa and I see you stroke it. I want to see long, slow, complete strokes, up and down, slide over, up and down, slide back, up and down." "Yes, Mommy Diane." Lisa's eyes were popping out. I had Sean step closer and turn this way and that to give Lisa a more complete view of Sean's masturbation. I was staring at Lisa. But she was lost in her concentration. She was squirming on the seat, crossing and uncrossing her thighs, not quite knowing what to do with her posture. I saw that Sean's pee hole was dilating a bit too close to the brink of a premature ejaculation. I made him stop. Turning to Lisa, I asked her point-blank, "Lisa darling, now it's your turn. Show and tell. Do you want to show or tell?" She panicked, "Mommy Diane, may I please tell?" I laughed, "Of course, darling, you will tell. Later you will have to show, too. Understood?" She nodded. Bravely she stood up and walked in front of me. I asked Sean to l sit next to me. She inhaled, swallowed deeply, and got the courage to ask, "Mommy Diane, what shall I tell?" "Lisa darling, what's the kinkiest, strangest thing Johnny makes you do?" Again, she panicked. Her body was shaking and trembling. She fidgeted and fought her self-control. She was desperately buying time. She wanted the world to come to an end. She wanted to leave to another universe. Finally, she blurted it out. "Mommy Diane, Johnny makes me wear a plaid skirt and an embroidered blouse. He says I was a naughty schoolgirl and that I have to take of my knickers. He makes me bend over the table and he spanks me with the ruler. Then he..." She was sobbing. "Then he what, Lisa?" "Mommy Diane, then he takes me from there." Sean was practically drooling pre-cum all over the place. He looked at me and I smiled back. I had to ask her, "Lisa, Johnny fucks you up your ass while you're dressed like a schoolgirl in a plaid skirt and embroidered blouse?" "Yes, Mommy Diane," her eyes lowered. "Lisa, look at me and say it loud and clear so Sean and I can hear you." "Mommy Diane and Sean, Johnny f-f-f-f-f-f-fucks me up my a-a-a-a-a-a-ass." "That's better, Lisa. And do you like it?' "Yes, Mommy Diane," her eyes lowered. Amazing discovery! The cute little nymph was into anal sex! And Sean was into prostate massages! The day was taking a totally different turn than I had planned! What a fortuitous discovery this had been! Breaking in and training -- both Sean and Lisa My mind was racing: there were so many interesting opportunities. With both Sean and Lisa into anal sex, I could have countless hours of endless enjoyment. But I knew I had to calm down and proceed slowly and deliberately. I had to be strategic and plan things perfectly. If all went well, this could be the first of many, many more anal sessions. I decided to go for the cute little nymph first. Ordering her to lie down in the living room floor, I told Sean to bring over two chairs. Lisa put her legs up on the chairs and Sean spread the chairs so that Lisa ended up with her knees wide apart and her legs up high. Motioning Sean to come closer, I told Lisa so spread her labia. Sean was staring intently as she opened herself up. At first Lisa was shaking and very insecure about it. This made it all the more exciting for me. Once she had spread her labia very far apart, as far as they would go, I ordered Lisa to unhood her clit. She was very uncertain what I meant, so I repeated it, this time in a softer, icier voice. Gently she started to pull back the protective hood. It was very uncomfortable for her, I could already see how sensitive Lisa really is. After some time and quite a bit of whining and struggling, she finally managed to pull the hood back all the way. Leaning over to get a closer look, I was surprised to see that for such a petite woman, how fully formed and well developed her clit was! I instructed Sean never to touch a woman's clit until she is screaming to be relieved of her repressed orgasmic agony. Woman have infinite erogenous zones: use and abuse all of them before attacking our clits. With Lisa thus spread apart on the floor, I told Sean to kneel next to her pretty face. While Lisa stared in amazement, I told Sean to pull back his foreskin all the way. This time I told Lisa to hold off touching the glans until the very end -- if at all. Men will do anything in the world just to have that last inch touch. Leave it alone until you got what you wanted -- anything you wanted! It was time to get started. Lisa was wetting profusely; Sean was dripping incessantly. I took them upstairs to my bedroom. Again I started with Lisa. Ordering the cute little nymph to kneel by the bed and place her torso on the bed, head on a pillow, I made her spread her knees wide apart. Telling Sean to pour warm baby oil on her ass, I taught him how to tease and taunt a woman's derrière. Warm baby oil dripping down her crack, Lisa moaned and purred. Granted, Johnny fucked her ass regularly so she was not the anal virgin I would have preferred -- but today she would learn interesting variations. Sean looked at me and I nodded. His finger pressed against her ass. Lisa was moaning. Quite simply, I told Sean to push it in. All the way in. No teasing, no foreplay, no preparation. Just go in. And I taught him a lesson he will use the rest of his life. Just as he is about to thrust into her ass, slap her derrière. Just once. Really hard. Invariably, the woman will be caught so totally off-guard she will have no control over her sphincter and will open right up. Sean smiled and continued to caress and tease her lovely derrière. When neither Lisa nor I were expecting it, Sean slapped her derrière and his finger went all the way in! The look of surprise on Lisa's face was priceless! I taught Sean how to slide his finger all the way into her ass and almost all the way out. Never go all the way out. Women have very sensitive nerve endings around our anal areas and can feel everything. Leaving even just the tip of his finger in her ass keeps those raw nerves stimulated. Lisa was moaning and purring like a kitten. She was trying to move her hips to one side or to the other. Sean quickly learned to have his finger follow her hips as they swayed from side to side. Let Lisa feel that no matter where she goes, his finger remains up her ass! Lisa tried to move her ass back, seeking deeper penetration. Again, Sean learned from me to keep his finger as deep or shallow as it was and just follow her ass. He has to set the depth of penetration, not she! More baby oil, lots of it actually, and Sean learned how to use TWO fingers up her ass. It's not just a question of more-is-better but a question of TWO fingers moving independently up her ass, giving Lisa totally new and unexplained sensations. Open the finger wide apart inside, move them side to side, feel her anal muscles struggle and tense up and relax. Sean asked me, "Mommy Diane, should I touch her clit?" I laughed. That's all men think of! Here was Lisa moaning and purring like a kitten, ready to go on for hours with such intense stimulation: make her ride the wave! But as a woman I could sense that soon Lisa might lose interest. Gently and patiently I taught Sean how to use his other hand. Again, extremely careful to avoid her clit, I showed him how to slip two fingers into her pussy and touch those up her ass. Sean seemed to struggle with this. I tried it. Lisa's pussy was even tighter than her ass! I had never seen a woman like that before, with a pussy far tighter than her ass. Must be all the gymnastics she did. I asked her if she did her Kegel exercises on a regular basis. In the midst of her anal purring her moaned, "Yes, Mommy Diane, every morning and every night." So there it was! The cute little nymph that so much enjoyed anal sex had a pussy so muscular and so tight she could actually control a man! More about this would come later! I taught Sean how -- still keeping TWO fingers highly active and deep up her ass -- how to reach into her pussy... there were two things I wanted him to find: the tiny urethral duct and her G-spot... all men think that fingering a woman deep up my pussy feels good... well, Sean learned right then and there just how sensitive the first two or three inches are... after that, we really cannot feel much difference... By keeping his pressure on her tiny duct, he could keep her from bursting... but it had to be done just perfectly... and Sean was learning just by learning from me how to "read" Lisa's body language as she moaned and squirmed and gasped... And Sean also learned right then how and where to find Lisa's G-spot... after that, it was almost straight downhill! He learned from me how to use his two fingertips to gently press down on that spongy mass of tissue... press and release, press and release, press and release... Lisa had lost complete control. She had lost her dignity. She was desperate. Amid the throes of her passion, I softly whispered in her ear, "Lisa, you are an anal whore. You are an anal slut. You are an anal bitch. Say it. Load" Diane Milking Sean Ch. 03 Lisa, hoarse and at her wit's end started to scream, "I am an anal whore. I am an anal slut. I am an anal bitch." Again and again, Lisa repeated her mantra. Sean was fingering her ass and pussy and G-spot even more intensely with every repetition. They were both responding to the mantra! Lisa's breathing was much faster. Her moaning became intense. Her groans were getting raspy. Her body was tensing up. Again and again she tried lifting her torso. I shoved her back down on the bed. At some point she even tried to race her hands down between her legs but I caught her just in time. Lisa was on the edge of the most powerful orgasmic volcano! The only thing holding her back was Sean's perfectly placed fingertip. I motioned to him to slow down. Slower. Slower. Much slower. Gently pull out. Very slowly. Lisa looked confused. She had been denied a massive orgasm. Why? What? How? I let her lie on the floor. Helping her hold her legs up high and near her face, I motioned to Sean to get a close look. Her ass was completely dilated. Her pussy was equally open, maybe not as wide as her ass, but still open. What I wanted Sean to notice was Lisa's clit. It stood out tall and proud and throbbing! Totally exposed, free of its protective hood, it looked positively majestic! Lisa was moaning and sighing and sobbing. I gave her lots of water to drink and helped her stretch out her arms and legs. "Lisa, get back on your knees. NOW" She pleaded, "Mommy Diane, will you allow me? Will you give me permission now?" I did not have time to waste. Turning to Sean, "Fuck the anal bitch. NOW." Sean wasted no time mounting her from behind. Little did he know what I had in mind for him. For them. The moment Sean's cock was up Lisa's ass, I thrust my THREE fingers deep into his ass. Fumbling around a bit, I finally found his prostate. My thumb pressing his duct, I started what was to be the longest, most intense and most enjoyable-for-me prostate massage. My other hand went into Lisa's extremely tight pussy, again completely avoiding her clit. Sean was fucking Lisa up her ass while my hand was massaging her G-spot. Sean was fucking Lisa up her ass while my hand was massing his prostate. Sean was thrusting deep into her ass. Like a wild savage, he was ravaging her petite body. Over and over again he thrust desperately into her. Just as he was wild, I was calm and methodical, sliding my fingers over his prostate, feeling it, kneading it. The gentler I was with it, the wilder Sean responded into Lisa. In his thrusts he tried to shake his body around but there was no escaping my firm grip of his prostate. Gently, softly, my long fingers cradling it, moving it around, feeling around all its circumference, pressing gently into it. What would have been many sure climaxes were prevented by the pressure I was exerting on the ducts. I knew Sean's testicles were churning on overdrive, producing sperm to inseminate a herd of women. But not a drop was flowing out! Lisa was besides herself. She had long since lost dignity and now was losing sanity. She too felt his throbbing cock slide up and down her ass. She sensed his foreskin moving around. She knew my fingers were wreaking havoc on her G-spot. Her clit was screaming for attention. I would not allow them to climax. Over and over again I played with Sean's prostate while he fucked Lisa up her ass. Over and over again I played with Lisa's G-spot while she clenched her ass tightly around Sean's cock. Gently and smoothly my fingers gliding over his prostate, driving him totally out of his mind. Like a stallion he fucked Lisa harder and harder. He bent over to give me more room to feel his prostate and in the process nibbled on her ears while she continued to scream. I nodded and he bent over further, giving me even more room up his ass to play while he found Lisa's nipples rubbing against the bed. I told Sean to pinch them. Hard. Much harder. Lisa was screaming. Sean was screaming. Without any notice, in one swell motion, I released Sean's duct while that the same time I gripped Lisa's clit in my three fingers. What an orgasm! Sean shot a single, long-lasting, abundant, powerful stream of ejaculate up into Lisa's ass! At the very same time Lisa screamed, lurched, and entered into massive convulsions and contractions as a series of never-ending orgasmic waves came crashing upon her. He kept shooting into her. And she kept shaking violently. Quickly I pulled Sean off and pushed Lisa to the ground. It took both our strengths to hold Lisa's legs wide apart. I wanted Sean to see something very few men in history have ever seen. Lisa's clit was actually throbbing so hard it seemed it was going to leap out of her body and into Sean's gaping mouth. But that was hardly the beginning. One massive throe of passion raced through Lisa's body. She lost self-control. Lisa started ejaculating! Huge squirts shot out of her pussy, long-lasting squirts, reaching clear across the room, while her clit danced desperately. She started to calm down a bit, her orgasmic throes slowing down. Her tiny pee hole began to dilate. Lisa could not help it. She started to pee on the rug. I let her, gently and softly encouraging her to finish peeing. It was a once-in-your-lifetime experience and I wanted Lisa to enjoy it to its fullest as much as I needed Sean to learn how to do it. I helped them both onto my bed and let them sleep an hour while I made some calls and prepared lunch. When they woke up, I had a treat for them. I had found Samantha's old school uniform in the closet: plaid skirt, embroidered blouse, white ankle socks and black shoes. She would dress in her husband's fetish! She fumbled feebly as she looked around for her lingerie. Her clit was still hard. She wanted to cover it up. I smiled and told her in no uncertain terms I wanted her clit exposed at all times. And that it would remain hard for a good three more hours. I had already beaten her to it. I tossed her panties over to Sean, ordering him to wear them. His cock was still hard. I would remain hard for a good three more hours. We went downstairs for lunch. She was oozing ejaculate from her dilated ass down her inside thighs. I smiled and told her it was perfectly OK. His cock was bulging and straining against her Snoopy panties. I let him move them off to a side and let his cock feel free. Slightly curved like a banana and his foreskin still quite raw and sore from the anal intercourse, he looked more handsome than ever! I felt so proud of my son and my daughter-in-law! Both were just learning the joys of intense anal sex. Both were just starting to learn the intensity of a very slow prostate massage and a slow G-spot massage. And since both would remain hard and aroused for another three hours, we could start right after lunch and a nap! While they slept in each other's arms that afternoon, I called Joel to make sure the visit was going well, I spoke with Johnny and Samantha and told them what a pleasure it was to be with Lisa and Sean for a day of "family intimacy." My perfect prostate and G-spot massages had resulted in his-and-her priapisms. Now I wanted to exploit their condition. Each would learn from the other how to do it just right. After all, I did expect Johnny and Samantha to benefit from me, their loving mother's imagination, creativity, and experience! The excellent idea I had, though, came crashing when Joel casually mentioned he had taken the video camera with them to video Nanna. So much for my idea of video recording the afternoon. Bummer! Hours later, both woke up, still in each other's arms, legs intertwined. I was sitting by the window, looking out, planning the next session. I heard them stir. Turning to look at them, I saw them hugging tight. In unison and without prompting or planning, both smiled and whispered, "I love you, Mommy Diane." They looked at each other and laughed. I walked over and untangled their limbs. Smiling, I replied, "I love you, too." Leaning over I gave each one a very soft kiss: his upon the tip of his still-very hard, throbbing cock; hers, upon the tip of her still-very hard, throbbing clittie. To myself, I thanked Priapus, the Greek fertility god often represented with a disproportionately large and permanent erection, and in whose honor the rest of the afternoon of sexual breaking in and training Sean and Lisa would proceed with unparalleled intensity.