Date: Mon, 13 Sep 2004 15:23:21 -0700 (PDT) From: Wendi Darling Subject: My Michaela 'Sissy Michaela' {Wendi} ( real con MB cd anal ) [1!3] Michael is my sixteen-year-old across-the-street neighbor who has been mowing my lawn for the past three years and playing with and walking my dogs, Prince and Princess, since I got them about seven months ago. He lives with his mother and an older brother, hangs out with the other neighbor kids, and had been seriously sniffing around Ashley, a short athletic well-packaged fourteen-year-old blond girl who lives two doors down from me. She lives with her mother and father and adorably cute and slender twelve-year-old blond sister, Brittany. I had recently been paying Michael ten dollars to mow the lawn, which I consider a fair wage considering that I supply the mower and the gas and oil. The job usually takes him about an hour or so, and his service is normally required from three to four times a month between March and November. That which I paid him supplemented what other income he had, allowing him to spend it on whatever it is that teenagers splurge on these days. I had casually talked with him before, about nothing in particular, and usually took him out some Powerade or water to quench his thirst. On one particularly hot day last April when he was cutting the lawn, I asked him if he wanted to come inside out of the sun and into my air-conditioned house while I got him a nice cold drink. He was amenable to that, so I had him come into the family room, and told him to have a seat and turn on the TV if he wanted, while. "Where are the dogs?" asked Michael. "They're over at the Vet's, today," I answered. "Check ups and shots and baths and shit like that." "Oh. Just wondered," he said. I went upstairs to get him a drink, and when I came back down with a coke-on-the-rocks for both of us, I found him leafing through my collection of adult and child pornography that I printed off the Internet, and had forgotten that I left sitting on the coffee table. "Hey! Who told you that you could look at those?" I said to him. "Well, they were just sitting there," said Michael. "They're really awesome! Where did you get them?" "Some off the Internet, but I get a lot in e-mail that all my pervert friends send me." I replied. "You've got pervert friends?" asked Michael while he absorbed all of what was in my porn stack and sipped on his coke. "Sure, Mike. Who's a pervert going to have for friends if not other perverts?" I said. "You mean you're a pervert, too?" "Why not?" I laughed. "Somebody's got to do it." "Wow! That's kinda cool, I think. You got more like this?" "Shitloads," I said, "but don't worry about more. You just started looking through those." I sat down on the sectional sofa, sort of 90 degrees from where Michael was sitting, and watched him. He is about my height (5'9"), weighs maybe 135 pounds, is muscled but not overly so, has short-cropped light brown hair, and was wearing a muscle shirt and knee-length khaki shorts with, from what I could observe, nothing at all underneath. His brown doe eyes widened every so often as he was looking through my 'filthy' pictures, and I could see a bulge starting to appear at the front of his shorts. "Like them?" I asked. "Oh, yeah!" said Michael. "I see that you've really been hanging around Ashley. You two look like you're joined at the hip." "What do you mean?" he asked, a quizzical look on his face. "Well, I see that you're always over at her house, and then I've seen her sitting and holding hands with you on your porch." "Oh, yeah, well..." said Michael. "Have you guys kissed?" I asked. "Sure," he answered almost absent-mindedly, while engrossed in poring over the porn pix. "I mean really kissed." "Of course," he sort of mumbled. "Have you done anything else with her, like feel her up?" I asked. "She lets me squeeze her boobs," he said, now being a little more attentive. "And she let me put my hand down her pants and rub her pussy, but only through her underpants." "That's cool, but it all kind of one-sided, isn't it?" I asked. "Ashley's getting all the pleasure feels. Has she done anything to you, like grab your crotch?" "Well, no, not yet," Michael admitted. "Then I can safely say that she's probably never given you a blowjob," I said. "Have you ever had anyone even rub your crotch or your dick?" "No, but Kenny and I have watched each other jack off," said Michael. Kenny is my next door neighbors' 14-year-old son, and he is Michael's best buddy. "You just watched each other? Didn't you even touch each other's cocks or play with each other?" I mockingly asked. "We don't do that!" Michael exclaimed. "We're not queers or gay or anything!" "You don't have to be queer or gay for that," I told him. "Ill bet that you'd like to, though. I saw your hard on get bigger when you were looking at the pictures of those guys blowing and fucking each other. Nothing wrong with that." I kept slowly sidling closer to Michael while we were talking until I was right next to him, my left thigh up against his right. I slowly put my right hand on his bulging crotch, but instead of him moving away as I had expected him to do, he put down the photos and moved his pelvis pressing his boner hard up against my palm. "Oh, my God!" he gasped. "Do it some more!" I happily obliged, and started rubbing and kneading his big bulge through his shorts. He responded with a long sigh and ground his groin to meet my massaging hand. I found the zipper under his shirt and pulled it down and his lovely 7-inch circumcised cock sprang straight out of his fly. It was as hard as a rock and I could see the blood pulsing up to the glistening head. I pushed his shirt up and out of the way and put my hand around his large boyhood and began to slowly pump it. My dear Michael put his arm around me and pulled me closer to him. I leaned over and gently kissed him on the lips, lightly teasing them apart with my tongue. He opened his mouth and I pressed mine over it. His tongue probed deeply into my mouth, and both of our tongues parried with each other, while I continued stroking his throbbing penis. "Would you like me to suck you off?" I whispered in his ear. "Oh, yeah, please blow me, Ed," he moaned. "Oh, yeah, please, now." I slid off the couch to my knees, and moved around in front of his. I reached up and undid the waist button of his shorts, and slid them down to the floor. After I removed his sandals and shorts, and pushed up his shirt, my lovely lad was now naked for me from the waist down. He had a small about of silky light brown hair at the base of his cock and a few strands on his adorable ball sack. I played with his nuts for a while, softly squeezing those jewels. They were slightly swollen and firm, and I know they contained a goodly load of cum for me. "Please hurry and suck me off, Ed," pleaded Michael. "I can't stand it, anymore." I spread the boy's legs wide apart, and bent forward and kissed the purplish head of his delicious looking cock. He almost jumped out of his skin. I licked the head and up and down the entire shaft while I fondled his balls, and he almost went out of his mind. Opening up, I took the head inside my mouth and then slowly engulfed the rest of his throbbing member until I had swallowed the entire 7 inches. His hairs tickled my nose. Michael moaned in ecstasy. Michael sat with his legs spread wide and his head back on the couch, and he had a dreamy glassy look in his big brown eyes. He was totally lost in the ecstasy of getting his cock sucked for the very first time. Slowly, I moved my mouth up and down on his delicious fuck tool, savoring the taste of his teenage cock. When I tasted the first oozing of precum from it's piss hole, I picked up the pace of my mouth massage. My head bobbed up and down, faster and faster on that piece of meat, from its swollen head down to the base of the shaft, while I sucked harder and harder. I deep-throated my honey. "Yesss, yesss, yessss!" hissed Michael. "Keep doin' it, Ed. Feels sooo good. Think I'm gonna cum!" Quickening my pace even more, I kept sucking on him. I felt him stiffen, and his cock flared out inside my mouth. Then I felt the muscles in his thighs tighten, and he grabbed me by my hair. He forced my head down on his rod, while his pelvis unconsciously came up to meet it. The head of that magnificently innocent pole hit the back of my throat, and he humped oodles of hot salty cream down my gullet. "Oh, God, oh, God, oh God!" he cried, as he emptied what seemed to me like gallons of cum out of his balls and into my waiting receptacle. I didn't let a drop of that delicious liquid go to waste. I somehow managed to swallow his entire load without spilling a drop. He kept moaning and moaning while I kept up my sucking. He was finally drained of his juice and his prick went limp. I released his prod from my mouth and proceeded to lick his dick and nuts clean of any traces of jism. He just laid back, totally drained and exhausted. "Well, how did you like that, Michael?" I asked, still on the floor between his knees with my head on his thigh and my hand fondling his genitals. "How was that for your first blowjob?" "Oh my God, it was awesome!" said Michael. "I never felt anything so terrific in my life! Fuck! It was fantastic! But from another guy?" "I'm glad that you appreciated my expertise," I told him. "Only another guy can give a truly good blowjob. Girls just can never know how it should feel. Besides, I've had plenty of practice. And don't worry about it being from 'another guy.' It's just sex and it's okay to do another guy just like it's okay for a girl to do another girl. If it makes you that uncomfortable, you can think of me as a girl. I'm bi, you know. You can even call me 'Wendi.' I'd like that a lot, but just when we're alone together." "I guess I could do that," said Michael. "You mean I can come back?" "Well, of course you can, sweetheart. Everyday, two or three times a day, whenever your little heart desires. Besides, you're here cutting my lawn three or four times a month, anyway. I'll make you feel like you died and went to heaven! I'll give you more than that Ashley will ever show you. You'll be hanging around me instead!" "I don't know about that, Ed...er...Wendi. I kinda really like her." "That's okay, dear," I said. "I won't be jealous. I'm willing to share you. You can do things with her, too. I wouldn't mind screwing the hell out of Ashley, myself. She looks like she'd be a wild fuck!" "Ya mean you like young girls, too?" asked Michael. "I like all youngsters," I told him. "I wouldn't mind throwing a good hump into her luscious little sister, Brittany, either. Or into Kenny's tall young cunt of a sister, Missy, for that matter." Missy, short for Melissa, is Kenny's rather tall (5'10") and sexy brown haired, blue eyed, 12-year-old sister. "But, don't you like any older men and women?" he asked. "Sure, but I really prefer kids and men," I replied. I was married to a wonderful woman and sex partner. She died over four years ago." "Oh, yeah. Kenny told me. I'm really sorry." "Thank you. That's sweet of you to say. I miss her very much. I'd like you to be my lover." "I don't know..." he said. "I'm not going to force you or anything, love," I said. "Just think about it. I would just adore having you as my own. Would you like another coke? I'll get you one while I'm upstairs. Do you ever drink alcohol? I can put a little rum and a squeeze of lime in it, and serve you a Cuba Libra." "I don't really drink, but that sounds cool," he said. "Thanks." "No problem, honey," I told him. "Take of your shirt, if you want, and make yourself comfy. It's all right for you to lie naked on my couch; I always do. You can turn on the tube or catch up on your reading while I'm gone. I won't be long." "Okay," said Michael, as he flipped off his shirt and laid his hot nude body on the sectional. I ran upstairs and into the bedroom. I ripped off my T-shirt and jeans, applied some 'Soft & Dri' Baby Powder scented Clear Gel deodorant under my arms and liberally spritzed myself with 'Jovan Musk for Women' spray cologne. I wanted to smell sweet for my sweetie. I put on a pair of black thigh-high nylon stockings, a pair of bright red satin bikini panties, and a red low-cut sleeveless belly shirt with peek-a-boo holes to enticingly show off my small but firm young girl titties. I put on a pair of red pumps with 2-inch heels, and grabbed a pair of suntan thigh-highs and a pair of hot pink satin bikinis for Michael. I hurried and made the drinks and went back downstairs, leaving Michael's apparel on the landing. "Ta da!" I said, as I made my way the rest of the way down to the family room with a drink in each hand. "Oh, my God!" exclaimed Michael, dropping a stack of porn from his hands. "You have tits! No wonder you want me to call you 'Wendi.' You look like a girl! We thought we saw you outside one time dressed like that, but we weren't sure." "Well, I am a girl, almost, sweetie," I said. "I have tits, a lovely 'clitty,' and a nice tight 'pussy.' And it's all for you! What more can a young man want? How do I look?" "AWESOME!" was all he could blurt out. I handed Michael his drink and he took a big gulp. He was sitting up again, so I sat down next to him, put my arm around him, crossed my legs, and whispered in his ear. "Would you pretty please do an itty bitty thing for Wendi," I cajoled. "It's just a tiny thing and it would mean so much to little ol' me." "What do you want me to do?" he asked, nervously, while taking another big swig of his drink. "I'd dearly love for you to wear a couple of nice little things for me," I answered, slowly moving my fingers up his high toward his crotch. "Just some girlie things." He took another sip from his rum drink, and finally agreed. The alcohol was making him loosen up and shed his inhibitions. I retrieved the lingerie from the landing and knelt before him. I rolled the thigh-highs and put one on each of his feet, in turn, and rolled them up from his toes to his knees. I stood him up and rolled the stockings up the rest of the way up his legs, making sure that the elastic bands hugged his thighs snugly, and purposely brushing up against his lengthening cock and tight young ass. I held the panties in front of him, and had him step into them. I pulled them up his legs and around his slender hips, and tucked in his penis with my have. He started a bit at my touch. "You look soooo cute, honey," I cooed, as I took his hand and ran to the bathroom with him in tow. "Come see yourself in the mirror!" "You are just a little darling," I said, positioning both of us directly in the center of the full-length 3-view mirror. "Don't you just look adorable? Don't we make a lovely couple? A couple of girlie guys! Since you're now to call me 'Wendi,' I'm going to change your name from Michael to 'Michaela' when we're together, but I think that I'm going to call you 'Mikki' for short. How does that sound, Mikki?" "Okay, I guess, Wendi," said Mikki, blushing from head to toe. "Come along, then sweetheart, and sit with me," I said. "There are a lot of nice things we've yet to do together." I sat Mikki back on the couch beside me, and snuggled up to him. I put my hand on his hairless chest and began to caress it. He sucked in his breath as I toyed with and then bit and sucked on his nipples. I guided his hand up under my shirt to my tiny breasts and my own hard swollen nipples. He kneaded, squeezed, and pinched them, and I moaned in delight. He was getting the hang of making love to another male, and I was sure that the bit of alcohol swirling through his system had helped. I pulled my top up and off, and Mikki's mouth went to my breasts, his teeth biting and his tongue teasing my aching nipples. The hormones that I was taking were really doing their job. My clitty was almost tearing a hole right through the front of my panties, and I could feel the wet sticky precum inside them. I reached down and slid my now soiled panties down off of my hips. My short engorged member sprang right up and stood proud and throbbing. I guided Mikki's hand to it and he wrapped his fingers around it. The built-up sexual tension from the sex that I performed on Mikki almost caused me to blow my load right then. I got up, grabbed Mikki's hand and flew with him into the guest bedroom. I flung myself back on the bed, dragging Mikki on top of me. I told him to jack me off. "That's all I'll have to do, isn't it?' he said. I don't know if I could give a blowjob." "That's all, damn it! Now, get on with it, Mikki, before I go insane from desire. We'll make a good woman out of you later. Maybe tomorrow or the next day! Hurry!" Mikki lay down beside me and again took hold of my throbbing clit. He put some of the lube I gave him on it and slowly began an up and down stroking motion. It was sheer ecstasy! I don't know where he learned it, maybe by jacking himself off, but I had never had anyone masturbate me like this young kid was doing. He applied just the right amount of pressure, and with the slickness of the lube, the amount of pleasure that I felt was indescribable. He slid that magic hand up and down the entire length of my oh so sensitive stick. My hips started grinding with a mind of their own and bucked up uncontrollably to meet every movement of his hand down to the base of my red hot shaft. I now felt the pressure building inside my balls, and they ached something terrible. With a couple of gentle squeezes on them from Mikki's other hand, my cum erupted from my cock like something akin to a volcano. He kept pumping my dick until I was drained dry. There was cum all over his hand and arm and all over my thighs, groin, abdomen and chest. I never thought that my nuts could hold that much cream. He wanted to wipe it off, but I told him that since it was because of him that I made such a mess, it was up to him to lick us clean. He initially balked, as I had though he might, so I reached for his hand and started licking my cum off of it. "See? I told him. "It's not all that bad. If I can do it, so can you. Now, be a good 'girl!'" "It's kinda salty and sticky, but it doesn't have too much of a taste at all!" he said as he lapped and licked the rest of my juice off of his hand and arm. "You've had you first taste of sperm, baby," I said to him. Now, do all of me! He dutifully sucked up the every bit off of me, even licking my balls and dick clean. "You tasted mine and I tasted yours. That sounds like a fair trade," I told Mikki. Now, how's about I take care of your newly acquired hard on? I'll be your bitch." I flipped my shoes across the room, and turned over on the bed and got on my hands and knees. I flipped him the tube of jelly and told him to squirt some up and around my asshole and then lube of his cock. I told him that he was going to fuck me. "I don't know," he said. "Guys don't do this!" "What do you mean 'guys don't do this?'" I said. "They most certainly do 'do this.' And what's with this guy-guy hang-up that you have? We've been doing guy-guy sex for the past couple of hours. Look. You're temporally back to being Michael, again, a guy. I'm Wendi, and I'm a slutty bitch whore, and you're going to fuck me. What's your problem? Besides, I really like to have my ass fucked, and if you won't fuck me, then Prince will after I pick him up. Now, let's go! It's almost time for me to pick up the dogs." "You let Prince fuck you, too?" "Yes, yes, doll face," I said. "And I fuck Princess, too. I'll let you have some fun with them, too, if you're good. Now, get with it. I don't want to waste that lovely hard on of yours." I helped him spread my cheeks, and then, finally, I felt that utterly divine cock of his touch my rosebud. He firmly pushed in, while I pushed my bowels out, in order to relax my sphincter muscle. I felt the rush of the mixture of erotic pain and pleasure as the head of his dick slipped inside me. He put his youthful arms around me and played with my tits as he slid his cock up to the hilt into my bowels. My God, what a feeling! There is nothing quite like having a young lover fuck one's asshole. He started with a slow steady rhythm, pushing his cock all the way up inside me, and then pulling it out until only the head was still in my ass. Then, all the way in, again. Those six inches of piston motion drove me practically insane. I could not wait for his inward thrusts and consciously moved myself back each time to meet them, my hips gyrating wildly. He really got into it as he lustily moaned and gasped while he rammed that pile-driving prick up into my rectum, and I groaned with total sexual abandon in return. After a while I lost all track of time, so lost was I in the throes of heavenly pleasure. My own clitty was on fire, but there was no relief for it right then. I came out of my sexual trance when I felt Michael banging me as furiously as I had ever been screwed before. I knew that he was about to cum in my hole. He stiffened, and then rammed home six or seven times with a force so hard that I thought he might tear me open. I then felt his hot cum filling my insides as he pumped himself dry. Simultaneously, my cltty started jerking as I experienced the most violent orgasm I ever had. I shot out so much sperm that I was amazed. And all this after having been jacked off to completion only a short time before. The other drugs I had taken to give me long-lasting erections and intensify and lengthen my orgasms and increase my cum output must have done their job. Mikki held me in his arms with his softening cock still implanted in my 'cunt,' as he played with my breasts. Once he finally, pulled out, I felt the load of cum that he deposited in me, start to leak out of my ass, soiling the bedsheets even more. I turned over and sucked that magnificent cock clean, and he surprised me my lapping the mixture of our sperm off of the bedclothes. "See, Mikki? With bisexual semi shemales like me, you can have the best of both worlds. Can Ashley do that for you? Stay and play with me a while and you'll never want to go back to her." "I'll see, Wendi. Haven't decided. By the way, can I come over tomorrow?"