Date: Thu, 17 Jul 2008 17:38:36 +0000 From: william michael Subject: Panties Are a Boy's Best Friend The following is a tale of teenage crossdressing, mother/son sex, teenage gay sex and various adult/teenage sexual encounters. If you find this offensive, please move on. If you are underage, please move on and come back when you are legal. Otherwise, strip down, sit back, lube up and enjoy. Laurie Simpson lay with her head on a firm bare abdomen; her lips nearly touching the tip of a semi-hard cock. Her right hand was cupping a large, smooth pair of balls partially encased in the sheer front panel of black nylon thong. Her other hand was lightly rubbing the edges of her own swollen pussy lips. While this might not seem to unusual for a reasonably fit and attractive middle aged woman fortunate enough to find a hot young stud, that fact that this young stud was her sixteen year old son makes the story a bit more unusual. That the thong was the lower half of a matching bra and panty set that had originally belonged to one of her now adult daughters merely added to the sense of the bizarre. She let her tongue slowly snake out from between her parted lips and lightly flick the tip of the flaring cock head. In the dim light of her bedroom she could see the cock twitch a bit and begin to swell. She continued her tongue work until the hardening shaft expanded to allow the cock head to first touch, then pass her lips. She closed her eyes in pleasure and she began to suck at the head of the best cock she had had in many years. She could feel that her son was moving as the effect of her attention began to seep down into his sleeping brain. He began to mumble a bit then awoke enough to speak coherently. "Oh, mom, again?" She let the cock pop out of her mouth and said quietly, "Please, baby, just one more time and then we'll sleep. I haven't had anything like this in years and years." "Ok, mom, but I don't know how much I have left." "You just lay there and I'll take care of everything." At this point he let her hand slid up to capture the base of this young, thick, eight inch cock that had become the focus of all her attention. She let her mouth enclose the head again and begin to work its way down towards the panty clad balls. She knew from earlier attempts that she couldn't take it all in but she didn't care. She just knew that she wanted her mouth as full as it could be. She heard the groan and felt the warm weight of her son's hand on her back. She worked her mouth up and down, leaving the smooth skin glistening with her saliva. She could taste the precum start to ooze from the tip. It was the sweetest thing she had ever tasted. She let her mouth drift to the top of the head with just her lips in contact in a loving, motherly kiss and then plunge back down to fill her mouth with the hard meat of this beautiful teenage cock. Now some of you may be wondering just how this turn of events had come to pass. Let us turn back the clock by just a handful of hours to earlier that same day. Laurie Simpson is fifty years old and is the single mother of three children, two daughters, 23 and 21 and one previously mentioned son, 16. She's been on her own for 13 years after her husband left for reasons not germane to this tale. She a marketing exec for a mid size consumer products company and is often required to work late. Today was supposed to be one of those days. She had told her son, Mark, that she had a dinner meeting with some prospective new clients and would likely not be home until after nine. This was nothing new for him and he told her not to worry, he'd be home right after school and had plenty to keep him busy. Around three in the afternoon she found out that they clients had been delayed in taking off and they wouldn't make it in time, could they reschedule for lunch the next day. Laurie agreed and took advantage of the situation to leave a bit early and head for home. She didn't bother calling her son; she thought she'd surprise him and bring home some pizza for dinner. She rolled into the driveway around five o'clock and as she walked into the kitchen through the side door she called out, "Mark, honey, I'm home. The dinner was cancelled." She didn't hear any response so she figured he was upstairs in his room and she went to the bottom of the stairs to yell up when she saw something she never expected. Her son was in the living room, shades drawn and the lights low doing a slow dance of sorts wearing head phones. What was really shocking was that he was dressed in sheer nylon thong panties and a bra, thigh high stockings and a sheer jacket that just came below his ass cheeks. His eyes were closed and his face looked dreamy as he listened to what ever music was moving his body. And what a body his mother thought. Mark was not an athletic boy in the usual sense. He didn't go in for the usual sports such as football, basketball or baseball. He preferred to ride his bicycle or walk. He was slim and trim with a slightly wiry muscularity. His skin was practically hairless and what hair he had on his head was blond and straight and cut just below his ears. With it pushed back behind the earphones it made it a very feminine looking hairstyle and overall Mark was showing a very feminine figure, flat chest not withstanding. She stood stock still watching as he swayed and turned, unintentionally showing her every angle of his body. His firm ass cheeks showed clearly through the shear jacket material with just the thin string framing them. When he was sideways she noticed the front of the thong bulged noticeably. To say that she was shocked would be an understatement but not entirely surprised. As a baby and young boy he would often find himself dressed up in his sisters' clothes as if he was a living doll. He would never complain or fuss. He seemed to actually enjoy his sisters' attention and they were never malicious about it. Often she would come across them playing their dress up games and the girls would be hugging and kissing him and dancing him around the floor. After a time Laurie had become concerned and by the time he was around seven she called a halt to it. The three siblings weren't thrilled but they adjusted. Or so she thought. She was conflicted as what to do next. Should she just go away and let him `discover' she was home, confront him or leave the house and try and forget it happened? Fate intervened at that point as the song must have ended and he stopped dancing facing directly at her. He opened his eyes and froze like a deer in headlights. They stared at each other for a few moments but he was the first to recover. He whipped off the head phones and said, "Mom, I, uh...," he tried to stammer out then he turned to flee. "Stop right there, Mark," she said sharply. He slowly turned to face her, his eyes wide and misty, his lower lip trembling. His mother looked at his dismayed face and her heart began to melt. More softly she said, "Mark, dear, tell me what this is all about will you? What he managed to stammer out through gulps and few sobs was that with both his sisters now gone he was feeling lonely in the house when he was by himself and a few weeks ago he was rummaging around in their room and found a box full of old clothes and things, things being underwear, lingerie etc., and remembering how much fun the three had playing dress up, he tried some of them on. He said it felt good and helped him feel close to his sisters again and since the dancing had been a fun part of it he tried that too. He finished with a last sob, a few tears running down his cheek. "You don't think I'm sick or hate me or anything, do you?" Laurie stepped quickly across the floor wrapped him in a hug. He was a couple of inches taller then she but with him in stocking feet and her in her low heels they were about even. She held him tightly to her and said in his ear, "You are my son and I could never ever hate you. But this is something we need to talk about. Put on a robe and come into the kitchen, I brought pizza home." Looking relieved he dashed up the stairs and she walked into the kitchen, kicking off her shoes and opening the boxes so she could reheat some slices. A few moments later Mark came into the kitchen wearing his usual knee length robe, but she could see he hadn't taken off the stockings. She herself was wearing a dark navy blue business suit with a hem just above the knee with a matching jacket and white blouse underneath. She removed the jacket and put it over the chair back. They sat at the breakfast bar next too each other. "First of all, Mark, I want you to know you're not in any trouble over this. What we need to do is come to an understanding aboutit. Is your interest in wearing girls or women's clothes something recent?" "Um, not really. I know I used to like it when Liz and Rita used to dress me up. It was fun playing with them and getting all that attention. But I liked the way it felt too. I know you kind of told us to stop but we used to find ways to sneak around and do it. The last time was about two years ago in fact. You were out of town and they were both home. They had me done up in a complete school girl outfit. They even made up my face." "I see. Well, I'm not thrilled that you disobeyed me but it could have been worse I suppose. Is there anything else I should know about? You know there are a lot of people out there that would love to take advantage of someone like you. Internet predators and such." "Oh, no. I don't do any of that. I keep it all to myself." "Well, that's a relief," she said, looking at him more closely. "You know, it's an odd thing for a mother to say to her son, but you did look very pretty dancing around in the living room." "Really? Wow, thanks, mom. But I don't think I look as good as you do." "And how would you know that, young man?" she asked. "Um, well, I've see you in your, uh, underwear a time or two, just a bit you know, if you didn't close a door fast enough or going from your room to the bathroom in the morning when you're getting dressed." "I see." "I'm sorry if I wasn't supposed to notice but you looked so good in your under things, filling em out the way they should be. Liz and Rita were always so worried about being thin but that just made them look like me, a boy in girls' clothes." "Well, thank you, Mark, that's very sweet of you," she said and leaned over gave his a kiss on the cheek. She felt him lean into it. When she saw the lipstick mark on his face she laughed a bit and took a napkin and wiped it off. Then she put her arm around his shoulder and pulled him close and he laid his head on his shoulder. "Now this is nice. The reason we got to it is a little unusual but it's nice to just sit here and be close." "I know," Mark answered. "Liz and Rita were always hugging me and I miss that. You've always had to work a lot to keep us going and now that they're gone, it get's lonely." "I tell you what, let me go get changed, then we'll take the pizza into the family room and have a movie night, how does that sound?" "That sounds great. Um, should I get changed too?" he asked quietly After a pause, Laurie replied, "Not if you don't want to." "Ok, thanks, mom." Laurie gave her son another squeeze and went upstairs to change. She slipped out of her skirt and blouse and she stood in front of the full length mirror on the closet door. She cast an appraising eye from head to toe and had to admit for an old broad she still looked pretty good. A bit thick in the waist perhaps but the skin was still firm and her 34Ds still looked good in her black lace bra that matched her low rider panties. On a whim she just pulled on a Japanese style robe that had been a gift from an overseas client and walked back downstairs on stocking feet. As she walked into the family room she found Mark standing there waiting for her. Slices of pizza were on the coffee table along with their drinks and the flat screen TV was on. He smiled shyly at her and she came over and again wrapped him in a tight loving embrace. She could feel him shiver a bit and she felt a tingle on her skin as well. His arms tightened around her and his soft smooth cheek was pressed to hers. She felt warm all over. They finally pulled away smiling at each other and Laurie said, "Now this is nice, some quality mom and son time." "Yeah, it's been a while since we've done this," Mark replied. That sat down next to each other on the couch and began to eat their pizza. They watched a couple of sitcom reruns, the ones where the dad's an overweight goof married to a stunning mom. "How do they expect us to believe that a looker like that would actually marry that guy, mom?" "Well dear, a lot of times a man that doesn't look so good now, looked a lot better in his late teens and early twenties. Sometimes they just let themselves go. In real life, the women do, too." "Well, this is real life and you didn't. You look great." "Thank you, sweetheart," she said and again kissed his cheek and again she felt him lean into it. At eight o'clock the new shows started up and they watched a drama. About half way through one of the female actors was shown in her bedroom wearing just panties and bra under an open silk robe and stiletto heel slippers. "Now there's a gal who didn't let herself go." "Come on, mom, she's probably thirty, what can you expect. You'd still give her a run for her money." "You think so?" "I know so." On a whim Laurie got up and stood next to the screen and opened up her robe revealing her lingerie. She struck a pose and said, "Think I still look good enough to be on TV?" "Oh, yeah, definitely." "And what about you? Think you're cute enough to strut your stuff on the screen?" "Maybe on the Bravo channel but I could never do that, I'd be too embarrassed," Mark said. "Don't ever be embarrassed by who you are, baby. Come here." Mark got up slowly and approached his mom. Her robe was open wide enough to fully expose her body from the front. She looked at him; full of the love a mother has for her son and said, "Take off your robe." "Are you sure?" "Yes, honey, I'm trying to make a point." "Ok," he said and slowly opened the robe and let it slide off his shoulders to the floor. He was still dressed in the panty and bra set with the sheer jacket over it. His hair was forward on his face now that the headphones were gone. He had his hands held loosely in front of him, partially obscuring the front of the panties. Laurie looked at him and had to admit he was a very cute person regardless of sex. "I want you to understand something. This is part of who you are. So is the fact that you are smart, funny, caring and considerate. Nothing about you should be an embarrassment. Yes, there are a lot of people that would find your desire to wear women's clothes abnormal, but a lot of people do it. You will just have to be careful of where and when you chose to do it and to whom you share it with. But never, ever, feel bad about yourself because you do, understand?" "Yes, mom, thanks." "Now come here and give your mom another hug. I've forgotten how nice those feel." They came together in an embrace and this one felt a whole lot different. This time lots of warm skin had come together that suddenly felt a whole lot warmer. Her hands were on his back feeling the thin material of the sheer jacket while his felt hers through the soft silky material of her robe. She could feel something else as well. The sheer nylon panel of his thong panties was pressing into her abdomen just above her own panties and the pressure was continuing to grow. She found this oddly exciting. A tingle she hadn't felt in many months was starting at the base of her spine. She gave her hips a little wiggle and heard Mark's breath catch. She whispered wetly in his ear, "Is that because of me, baby boy?" "Um, I guess so, mom, I'm sorry." "Don't be sorry, baby. It's very flattering," she said this as she pulled her face back a bit and she was again going to kiss his cheek but he turned his head a bit and her lips contacted his about half and half. "Mmmmm, that was nice," and she meant it. She wasn't sure why but she knew she wanted to do what happened next. "But I think it should be more like this." This time the kiss was squarely on his lips and it was warm and wet and after a moment involved her tongue pushing past his lips to find his. She let her hips move a bit more and she could feel something definitely happening down there and what ever it was it was substantial. She let one hand drift to the back of his neck and pulled his lips tighter. When she first kissed him he had stiffened but now he was just melting into it and letting it take him wherever it would. Laurie was the first to break off the scorching kiss but it was only so she could shrug off the short robe she was wearing and push his shear jacket off. She pulled him to her again, this time with her hands on his now fully bare ass cheeks and his hands roaming all over her back and panty clad ass. As she pulled his hips tight up against her she could feel something hard, warm and slightly sticky rubbing on her stomach. She let a hand slide around his hip and slip in between and she was greeted by a thick hard shaft and large head that was already drooling precum. "Hmmm, I wanna have a look at that," she mumbled into his mouth. She pulled back and looked down and saw a beautifully formed cock poking up above the top of the thin film of material, the head of which was glistening with sticky fluid. "Oh, baby, what a beautiful cock you have there." She let her hand slide down the shaft and inside the skimpy panty material. She could feel the smooth skin of his ball sack and she wanted to see if what she was feeling was a big as she thought. She slipped the panty front down and let it tuck up under his balls, which now hung free and loose. They were an impressive sight. She continued to fondle his very impressive package as she looked him in the eye. "My boy has sure grown up. Are you sure this is ok with you?" "I'm loving it, mom. I know it's not something we're supposed to do but I'm not supposed to be wearing women's underwear either so..." he trailed off. She pressed her lips to his again but this time left room between them so she could play with his hefty balls and big cock. He in turn took the initiative to begin to massage her heavy tits through the thin bra material. He was rewarded with a deep moan and tight squeeze on his dick. After several long moments of this she began to lead him back to the couch without breaking lip or hand contact. They flopped down onto the couch and then Laurie leaned into her son until he was lying on his back and she was laid out on top of him. Now she was grinding her panty clad pussy along the hard underside of his shaft. Mark could soon feel the wetness leaking through the material as it lubricated his shaft. He slipped his hands under the material covering her ass and began to squeeze and knead the soft warm flesh. "Omigod, I've got to have you, baby," she rasped. Sitting up, straddling his hips, Laurie pulled aside her panties and began humping his cock with her bare, swollen lips. The she rose up a bit and let the head come to rest between the swollen lips. Then she let her weight push the head in and Mark let out a groan and his head lolled back. She sank further down and as the thick shaft followed the head she began to moan and Mark's hands came up to rest on her hips. She sank all the way down until she was sitting on his thighs and she leaned forward until her clit was rubbing on his abdomen. She began a slow grinding, letting his big cock work its way around inside her. It had been over a year since she had had a cock inside her. Not since that seminar where she spent three nights fucking the hell out of a thirty year old black sales rep and Mark's dick was a match and then some for that one. His hands had once again come to massage her tits through her bra. She sat back a bit and pulled the cups of her bra down so that the full breasts could hang out. She reveled in the feel of his smooth warm hands rubbing the skin and playing with her stiff nipples. Nothing anyone could tell her at that moment would convince her that this was the wrong thing to be doing with her sweet beautiful son. She continued to ride his magnificent cock as a strong tension began to build inside her. She clamped her hand over her son's and she began to grind and buck her pussy all over his well lubed dick. "Oh, baby, yes...omigod...I'm going to, yes, oh yesssssssssss.." she began to hiss as the first wave of her orgasm hit her. Mark had been getting that familiar tug at his balls but it was stronger then he ever remembered. It felt like his cock was going to burst along the entire shaft. As he felt his mother's pussy clamped down on his shaft as she bucked through her orgasm he let out a groan and began to hammer his hips up at her as his own orgasm propelled thick streams of hot white cum into his mother's pussy. They continued this way for a seemingly endless moment until they were both drained. Her hands dropped to her sides as his slid down to her waist. She leaned forward until her chest was pressed against his and her lips were hungrily grinding on his. His hands came up around her back to hold her tight and his cock remained implanted deep inside her, occasionally twitching. After a few more minutes of hot kissing she pulled up a bit and said, "Oh, my baby. You may only be sixteen and wear women's panties but you fuck better than any man I've ever known." "Does that mean I have to stop wearing them?" "OHHH, no. You can wear them anytime you want inside this house. We'll look for some of your own from the catalog," she said as she kissed his lips. "Maybe we'll add a little make up. You'd look gorgeous with a little effort." The idea of having his mom make up his face like his sisters used to gave him a thrill down his back that he felt arrow straight to his balls. He pushed up with his hips and ground against his mother's weight. She purred a little as she looked down at him, her eye's half closed, "Hmm, my baby likes that idea, huh?" she said as she pushed back down. "I think you'll like this idea even better." She lifted up off of him, letting his cock slap against his belly. She slid down so she was kneeling between his legs and ran her tongue along the glistening shaft of his dick. She reveled in the taste of the combination of his cum and her pussy juices. She continued to lick him as he squirmed and moaned. Once it was clean she took it in hand and began to lay sucking little kisses all around the head. Then slowly she fed the head and part of the shaft into her mouth. She couldn't believe how hot it felt resting on her wet tongue. She began to suck in earnest, applying suction when just the head was between her lips and squeezing and stroking the shaft as her lips rode up and down. She let her free hand slide up his firm abdomen and slip under the cup of the little bra he wore, finding his hard nipples to rub and pinch. His hips began to buck and twist as his balls pulled up tightly. In less then ten minutes he was ready to fire another load though his man sized dick. "Uh, oh, mom, I'm gonna cum..." She didn't back off. She continued to suck and stroke and rub and pinch until he finally arched his back, driving his cock deep into her willing mouth. With a grunt he let go with a thick stream of cum that splashed at the back of her throat. Two more thick streams followed and she struggled to capture it all, but she did. She didn't release his dick from her mouth until his orgasm faded and she kept sucking until every drop was pulled from his balls. She let his cock drop back against his belly as she slid her body snakelike up his torso, her heavy tits pressing her hard distended nipples into his skin and dragging them along his body. She brought her cum smeared lips to his and began a long slow grinding kiss, pushing some of his cum into his mouth and then mixing her tongue with his. After a long moment she broke the kiss and smiled at him, "How was that, baby?" "It just keeps getting better and better. And thanks for sharing some of my cum. I always lick my fingers clean after I've jerked off. I love the taste." "I'm glad baby," she said lazily. "We'll share many loads together from now on." She started to kiss him again and they kept it up for many minutes. Finally she let her head slip down to his shoulder and with his arms around her they drifted off into a contented sleep. After an hour or so, Laurie began to stir and as her eyes opened she focused on Mark's black bra clad chest. She smiled a little and wondered how all of this was going to play out but at the moment what she felt she needed most was a long warm shower and she didn't intend on taking it alone. She moved her head up and planted a little wet kiss on his ear. "Wake up, baby." "Hmmphffff," was the only response she got. This time she stuck her tongue in his ear and gave it a wiggle. Mark's eyes shot open and he looked around a bit confused trying to get his bearings. "Hello, my beautiful boy." "Oh, hello, mom." He had turned his head so she took the opportunity to plant a smoldering kiss of those perfectly formed lips. The traded tongues for a bit and then she pulled off. "I need a shower and I think you could do with one as well. We'll save some water and take it together." "Really?" he said in surprise. "Oh, absolutely, baby boy. Come with me." "Every chance I get." She laughed as she recognized the pun and let him roll off the couch first and then standing above her with his limp cock hanging over his black panties he offered her a hand up. As she came to her feet he pulled her into a tight embrace saying, "I love you, mom." "I love you too, baby," she replied and proved it with another long burning kiss. By the time they pulled apart he wasn't limp any more and as they walked hand in hand upstairs to the shower his cock was bobbing in time to her tits which were still free of their bra cups. Laurie started the water flowing and they each stripped out of their lingerie. The shower stall was steamy as they got wet and began to soap each other up, cleaning away the residue of their passionate sex. Needless to say all this attention hand them both wound up against the stops again and soon they were embracing, kissing and grinding against each other, aided by the slippery soap suds. Laurie pivoted in Mark's arms and pressed her back to his chest, feeling his fully rigid cock pressed into the upper portion of her ass and the small of her back. His hands came around and cupped her weighty, very slippery breasts and he fondled them for all he was worth. They were both moaning and groaning as she pushed her ass back hard to increase the pressure on his cock. She swiveled her hips to further stimulate her son's already dripping dick. She then reached for the tube of oil gel that was on the shelf and turned to her son. "I have another treat in store for you, baby." "Hmm, I love your treats, mom," he said with a smile. She poured a large dollop of gel onto his fat shaft and began to rub it all over including the head. Mark closed his eyes and tilted his head as he reveled in the feel of the cool gel and her warm hand. She squeezed a bit more onto the tip and left it there. Then she turned around and leaned forward a bit. With one hand she pulled an ass cheek to one side, exposing her pink asshole. With the other she took her son's slippery shaft and placed the slick head to her hole and leaned back into it. "You grab my hips, baby, and keep the pressure up. You're going to love this and so will I." Too stunned to even speak, Mark took hold of his mother's wet hips and pushed forward with his hips. Their combined efforts resulted in the slippery head smoothly flowing past the tight ring of her ass. While Laurie was no anal virgin it had been a long time and she was very tight, but very eager. With some coaching and coaxing and some combined effort she soon had the entire length of his gorgeous cock embedded in her ass. She was cooing and moaning and Mark was grunting and `ohmigoding' as instinct took over and the natural rhythm of man fucking woman took over. Laurie braced herself against the stall wall as Mark plowed her ass for all he was worth. Where his mom's pussy had been warm and wet, her ass was hot and tight and the lube gave it a delightfully slippery feel. Seeing her ass jiggle each time his hips came in contact was turning him on more and more. Her moans and groans were music to his ears. He pushed his cock in as deep as it would go and he let his hands slide off her hips up to her full hanging tits. He squeezed and fondled the heavy flesh, the hard nipples pressed into his palms while his hips pushed and twisted to grind his cock in and around her asshole. He could tell that she had at least two orgasms while he butt fucked her from the way she stiffened and the vise like grip as her ass clamped down on his shaft. He could now feel her working up to a third that should be the biggest of them all. He pushed and squeezed as hard as he could and when he let one hand slide down to flick her clit he felt her go over the edge. She squeezed on his dick so tightly that he couldn't move it but it was enough to send his cum shooting far up inside her as his big balls unloaded their heaviest delivery of this wild day. His mother screamed out her ecstasy as he let out a low, loud moan. Their bodies jerked and quivered and spasmed for what seemed forever until they finally had nothing left to give. Laurie was the first to move as she pushed off the stall wall and leaned back against her son, her head resting on his shoulder. His arms were around her waist and he was kissing her neck. He could still feel little jerks and spasms from his cock as it remained firmly encased in his mom's warm wet slippery ass. "Oh, baby, that was the greatest ever. You fuck me better then any man I've ever know." "That's because I love you more then any man ever could," Mark said into her neck. "Hmmm, you may be right. I wish we could stay like this forever but we need to clean up and lay down before we fall down." With that said she moved forward and felt his fat delicious cock slither out of her well fucked ass. They soaped each other up and in the last remaining bits of warm water got clean. They stepped out of the shower and dried each other off, taken time to kiss and cuddle and fondle. She then led her naked son to her bed and they lay there cuddled up, he on his back, she pressed to his side, one arm over his torso, one leg over his and they fell into blissful sleep. It was a few hours later when she awoke and found herself staring at the head of the most beautiful cock she could imagine, made all the more enticing since it was her own son's. And so we come full circle in this tale. And she began to suck and fondle as her somewhat awake son lay there with his hand on her naked back, and she sucked until she was once more rewarded with a much smaller but still satisfying load of teenage cum. And as promised she shared it with the teenage son that gave it too her and having shared one last long cum smeared kiss they faded back into sleep and completed the first of many nights on what was to prove a long and loving journey of discovery and sharing. To be continued.