Louise and Sherry


Louise and SherryThis is a work of fiction intended to entertain and nothing more. It is contain cross dressing as well as sexual intercourse. I would love a thumbs up if you enjoy the story, it encourages me to continue writing.“We are like clay when we are young,” Louise said, “and our life’s experiences mold us into a shape in our young impressionable years.”“I am so sorry,” I said as she looked at me standing in her bedroom wearing her full slip. What she hadn’t noticed at this point was the fact that I was also wearing her new long leg panty girdle. Both items were lying on her bed when I passed down the hallway. I thought I was alone and in a instant a voice inside of me told me to try them on.Louise was to become my mother in law in a week and our lives were filled with all the preparations for our wedding day. Sherry’s mother was a wonderful person that had accepted me more as a son than a future son in law. A big turning point in my life was when Sherry and I had met at the age of 16. I suddenly felt as though my 5 year obsession with cross dressing had ended forever. Now 6 years later I had been caught red handed in a fetishistic moment of weakness.I won’t say it was snooping, Sherry had asked me to take some wedding gifts from my place to her bedroom. She was still living with her widowed mother in the bedroom she had grown up in. I was intimately aware of Sherry’s bedroom, I had taken her virginity in that room 6 months after we met and it was always a special place to me. We’d had been very discreet with our sexual relationship because she worried her mother would be upset if she knew we were sexually active.I had dropped the gifts in her room and after a moment of reflection on our first time in this room I was to say the least, aroused. I thought back to that lazy summer afternoon after swimming at the municipal pool and I drove her home to change for an early dinner and movie. “Come inside and wait Larry,” Sherry said, “it is too hot out here in the car.”Louise was at work and the moment the door was closed I had my arms around Sherry. Her one piece swimsuit was soaking wet and clammy feeling against me. I had nothing but swim trunks on. We kissed passionately and my cock responded as it always did when we were close. And this is as close to her bare body as I had ever been and I knew she immediately felt my hard cock pressed against her. I pressed my erection against her and she responded by grinding against me as she broke the kiss.“Let’s go to my room,” she said and led me by the hand to her bedroom. Her room was typical for her age, all girly and some of her clothing d****d across chairs and stands. As we hugged again I saw her pink panties lying on the floor where she must have slipped out of them getting ready to go swimming. I let my hands move down her back and onto her butt. She didn’t do anything to stop my advance so I cupped her butt and pressed her against my erection again.We kissed and our breathing became ragged and our tongues met. This was not the first time we had kissed, nor was it the first time I had my hands on her butt or between her legs. But this was the first time that there was nothing but a thin bit of spandex between us and she responded to my caresses with quiet little moans. I ran my hand around front and instead of going for her breasts as I always did my fingers rubbed the spandex suit between her lips. She humped against them as she looked into my eyes.I looked into her eyes, they seemed to be begging me to take charge, “or was it my imagination?” I wondered. I slid a finger under the crotch of her suit and she was warm and wet, not wet from swimming but wet from her arousal. Her hairy patch tickled the tips of my fingers as I explored her slit. This was completely uncharted territory for me but I had heard plenty of reports on what to do. I slid my middle finger deep between her labia and felt her vagina, the fluid was thick and slippery and she humped against my finger pushing it in past the first knuckle. I pushed in as far as I could but standing and suited I was not getting in very far.We backed towards the bed and I eased her down reluctantly pulling my finger out from between her legs. She jumped up and my immediate reaction was to apologize, “I’m sorry,” I said, “I thought you wanted…”“I do,” she said, “but I don’t want my wet swimsuit to stain the comforter.” She flipped the comforter and top sheet back and then turned. “This is the way I want my first time to be, naked and in bed,” she said as she slipped the straps off her shoulders and peeled the suit off.All our sexual contact before this had been over each other’s clothes, now she stood in front of me naked and shaking. “Are you scared?” I asked.“A little,” she said, “but not so scared that I want to stop,” and she pulled my trunks down exposing my erection. “I have never seen a penis before,” she said as she wrapped her fingers around my shaft. “I have only felt yours through your jeans.” I felt a shiver run up my spine with the pleasure of her soft hand on my cock. I was the only one that had ever touched my hard cock and her touch felt beyond what I thought it would be. “Is this the way I should do it?” she asked as she slowly ran her hand up and down my cut cock.“Yes Shelly,” I said as I cupped her bare breast for the first time. I was amazed at how soft they felt outside of her bra. Yet they were firm enough to not sag like the old hags I had seen in an old porn magazine a guy had at school. Her nipple responded to my touch and she closed her eyes and our lips touched. I felt her hand push my cock down and rub it against her wet slit and I felt like I was going to cum immediately. I pulled back from her slit and her hand.“Did I hurt you?” she asked.“No, it just feels so good I don’t want to cum right away,” I said. “I want to make you cum only this time not in your clothes like we have been doing. I eased her back on the bed and lay beside her. The scent of chlorine from the pool mingled with the scent of her arousal as my fingers slide along her slit and I found her clit.“Oh yes Larry,” Shelly said, “just like that. You will make me cum, ummmmm,” and she did. I felt her tense with the start of her orgasm and she moaned softly. She turned her face to me and I could see this dreamy look in her eyes as she smiled. “That was easy, I have wanted you to touch me this way all day. Now it is your turn.” She said.I rolled onto my back expecting her to give me a hand job. Instead she rolled on top of me, “I want you inside of me, just don’t cum in me.” She said. She didn’t wait for me to respond and put her hand between her legs and guided my rock hard cock to her pussy. “Go slow Larry, my girlfriends’ say it hurts.”I pressed into her and almost shot my wad before we started. It took all my will to think of anything but the fact that Sherry and I were having intercourse. I felt her hymen and stopped. “Are you sure?” I asked.“Yes,” she said and I felt her press down on my cock. She bit her burdur escort lip as I broke through her maidenhead that had never before been touched by a cock or even my fingers. I saw her blink her eyes and asked, “Are you okay?” “Yes, just give me a second.” And I watched her face as it seemed to soften and I felt her drop down against me. I was balls deep inside of her warm wet pussy and knew I wouldn’t last. “We need to be careful,” I said, “I am real close, maybe I should pull out.”“No just hold there, I love how you are filling me up I have never felt anything like you being inside of me. I won’t move if that helps.” She said and bent slowly forward and her breast brushed past my face. The distraction of her nipples brushing against my lips gave me momentary control over my pending ejaculation. I was scared to death of blowing my cum inside of her but held perfectly still until she said, okay let’s stop until we can get a rubber for the next time.”I felt her hips move and as she started to pull off of me and I felt that cramp deep inside and arched my back to pull out and squirted my cum all over her tummy. “You weren’t k**ding,” she said as she watched my cock jerking out my pearly white cum. “Is it always that much?” She asked.I looked down, “sort of I guess.” I said hating to admit that I jerked off a lot and knew exactly how much there was, and this was more than when I jerked off. Sherry rolled off of me and laid beside me. Her breasts pressed against my arm as her hand cupped my cheek and pulled me to her for another kiss.From that day forward Sherry and I had what every young couple has once they have broken past the awkwardness and anxiety over their first time. We became very adept and at bringing each other pleasure and satisfying our needs. And yes I did enjoy seeing her wearing a bra and panties. On several dates she wore a girdle. My favorite was the traditional girdle that allowed me full access to her pussy without stripping off the tight constrictive girdle that I had loved in my cross dressing days.And now a week before my wedding it seemed I had ruined a very good thing. My soon to be mother in law was looking at me wearing her full slip and panty girdle. I felt like I should cover myself but my clothes lay in a heap beside the door showing my impulsive act. I would not look at her being so ashamed of what I had done. “Just like the potter or sculpture molds a piece of clay into something of beauty I believe we are all molded into a shape that becomes pleasing to us and to others.” Louise said as she circled around me. I felt her hand on my shoulder and it moved down onto my girdle covered ass. “Do you know how long it has been since I have felt this?” Louise asked. “Of course not, Sherry knows little of her father. I lost Henry so many years ago,”I felt her hand run down over my firm girdled ass, gliding over the silky slip. “Henry liked the softer side of life as well and it was always part of our love making.” I felt her finger tips trace the line of the back satin panel that ended as it met the nylon crotch panel. My cock was hard inside the girdle but safely hidden from view. “It has been 12 years since I enjoyed a man in my bedroom and I never thought I would find another Henry.” She said as she cupped my ass and then circled around me.“Tell me Larry when did you first wear women’s things?” Louse asked as she stood in front of me. I could smell the scent of her sweet lilac scented perfume. Her breasts were just inches away from my chest as her hand lifted my chin. “Tell me how this started.” She said with a soft soothing tone in her voice.From my earliest thoughts of sex I had been drawn to any woman’s undergarment and had been a horrible little wretch with snooping in any drawer I could find to discover the secrets of woman’s under clothes. Of particular interest to me were my mother’s full slips. I have no idea how many times I had pulled one out of the clothes hamper, off the basement clothes line where one had been drying, or out of her dresser drawer. But I know that my first orgasm came as the result of the touch of that soft silky nylon on my little cock. “How could I tell my future mother in law these sordid details?” I thought as I looked for the right thing to say.Louise ran her hand down my front and again traced the lines of the paneled girdle and then I felt it. Her finger tips found the tip of my cock held hard against my pelvis. She circled the tip of my cock with her forefinger tip. “I see you are aroused,” she said as she looked into my eyes, “A girdle was henry’s favorite, it made him so hard.” I looked at the woman I had known as Sherry’s mother and for the first time realized I knew so little about her. “You have nothing to fear Larry,” she said. “This will be our little secret but I need you to tell me how this started.”“Well I was dropping off the gifts ….” I started to explain.“No not today,” Louse said with a smile, “I can see you stripped out of your clothes and into my under things, no tell me when it started.”“I think I was 11,” I said. “It was my mother’s full slip.”“I thought so,” Louise said, “tell me more.”For some reason it just felt like a relief to finally try to put into words what had happened to me at that tender age. “I would slide the slip over my naked body and feel it cascade down my body. It was always too long, nearly to my feet, but the luxury of that nylon was like heaven to me. At first I thought this must be like a girl wanting to be a princess as I would whirl and twirl in front of the mirror.” Louise guided me to the bed and sat beside me.“You were young and innocent,” Louise said. “Just like I said we are but clay that becomes molded and wearing that slip was part of what molded you into what you are. Will you tell me more?” Louise asked as her hand caressed my knee and ran up my leg.“Well the more that silky nylon spun across my penis the more excited I would get. Then one morning while all alone at home right in the middle of my little dance and fantasy my body took over and I was never the same. I felt like I had to pee but unlike that urge I couldn’t stop what happened.” I told her not believing I was admitting all of this to her. I had never told anyone about this.“So you had your first orgasm,” Louise said pushing my knees apart and running her hand between my legs, sliding the slip along my girdle covered inner thighs. “And that experience molded the clay as well.” She said. My cock was held tightly inside of the girdle as her hands moved up and down my thighs yet it seemed I could feel something building inside of me. I was horrified. I had learned to control my approach to an orgasm but suddenly it felt like I had lost control.“Tell me about the first time you had an orgasm.” She demanded. For some strange reason I had lost all inhibition about the subject and the rest just spilled out of my mouth. “My little cock jerked and spurted something out the end and it soaked into the beautiful mint green slip. escort burdur Then it did it again, and finally a third time.”“The slimy stuff soaked through the slip. I was shocked and immediately felt this horrible thought that I had ruined the slip. This was coupled with thoughts of shame and guilt for touching the garment and then wearing it. I stripped out of it and looked at my little cock. It was still hard and pointed up at me as if pointing to the guilty culprit that devised this horrid plan. I saw the creamy white fluid bubble up on my tip and touched it and a little more oozed out.”“And that was the start to my years as a horrible little wretch. I had no self control. But when I met Sherry all the urges stopped, I swear Louise this was an impulse I will regret for the rest of my life, can you forgive me?”Her hand had never stopped moving. I watched her long slender fingers with her bright red nails slide up and down my leg. Then her hands were between my legs gliding to where my balls were hidden under her girdle. “You have nothing to be ashamed of Larry.” She said.“Your story is so much like Henry’s that it is remarkable. Like him, you were molded by these early experiences. And regardless of the layers time applied to the surface of the clay the underlying shape remains. Does Sherry know about your secret?” She asked.“No, I thought it was gone and over,” I said wanting to just bolt out of that bedroom but knowing my life with Sherry was at stake.“I will tell you I was molded by Henry’s desires. Instead of rejecting him when he told me his story I accepted it. Unlike you his desires only grew stronger when he started seeing me wearing my underthings. And these desires became a part of our sexual life. I am not sure Sherry would accept it, but I do.” She said and pushed me back onto the bed. Her hand slid under the slip and she ran her hand fully over the bulge of my cock in the girdle. She ran her hand softly over the satin panel of the girdle stimulating my cock to the point I knew I would be leaking pre-cum.“It is time to take off the girdles,” Louise said and stood. She opened her dress and dropped it to the floor. Her white full slip covered her body like liquid satin. It was a pretty lace covered slip that begged me to touch. She pulled at the skirt slowly and I could see she was wearing a panty girdle with short legs and a plain white bra. Her fingers caught the waistband of the girdle and rolled it down. “Henry said it was as much fun watching me take the girdle off as it was for him to watch me put it on.”I couldn’t believe this was happening. I was watching my mother in law disrobe and I did nothing to stop it or look away. It was like I was in a trance, like a moth drawn to the flame. “Please don’t deny me Larry,” Louise said, “I need you so badly.”With her girdle lying on the floor she let the slip cascade down over her trim figure and had me stand. I felt her hands raise the slip I was wearing and she rolled the girdle off of me. “We always need to take care here,” she said as she pulled the girdle away from my hard cock. “We don’t want to hurt this guy before he does his job,” she said guiding my cock out of the girdle.I should have protested. I should have been stern and left the room. But in that moment I wanted her as much as she wanted me. I had never had a thought of her in any sexual way. But her soothing voice and gentle touch was more than I could resist. With the girdle at my feet Louise pulled me to her and my slip covered cock glided across her pelvis.Suddenly this moment felt like the time I took Sherry’s virginity. But Louise was 20 years older and the mother of my soon to be bride. Yet it felt so right. We tumbled onto the bed and my hands were all over her back and her butt. Her slip was so silky and soft and I couldn’t stop touching her body.She caressed my slip covered cock gently, “I think you are not going to last too long with all this stimulation she said,” as she stopped caressing me. She rolled me onto my back and swiftly mounted me pulling her slip up to expose her hair covered pussy. Her arousal glistened on the dark curly hair as she pulled my slip up exposing my rock hard cock.She guided me between her legs and I felt the heat and wetness and was lost to any reality. I plunged deep inside of her. Her bra covered tits were hovering over my face, I wanted them bare and in my hands. I wanted her nipples in my mouth. But I knew I was not going to last very long.“We need to be careful,” I said, “I don’t want to get you pregnant.”“I won’t,” she said, “there were complications when Sherry was born, that has all been taken care of,” She said closing her eyes and began rocking hard against my cock. I looked at her face, it was an older Sherry, and just like Sherry’s first time with me, there was a determination in her expression. I could not imagine going 12 years without sex. I decided that since my marriage would probably never happen now I just as well give Louise the best I could give.Louise rocked against my cock with our slip covered bodies slipping effortlessly against each other. Then I felt her tense up and stop. Her pelvic muscles gripped my cock and she made a deep throated sound of pleasure and then rocked spasmodically back and forth on my cock and then held tight against me. Her orgasm seemed to last for a long time and then she opened her eyes.Looking down at me she smiled, “that was a long time coming Larry,” she said as she slid off of me. I started to move, “Stay right there,” she said as she pulled her slip up and off. She reached behind her and released the hooks of her bra. Her ample breasts showed every line from the seams of the bra. “Now we are going to get serious,” she said as she crawled back on top of me. A woman of forty is still vibrant and sexual and she proved this as we coupled again.It was like I was possessed. My hands were all over her like we were long time lovers. She rocked hard against me and caressed my slip covered body. “I love a man in a slip,” she said as she took me to the edge of an orgasm. She seemed to sense it and stopped and smiled. “You are so close aren’t you?”I nodded yes. “Well this time we won’t stop,” she said as she began moving again. And we didn’t stop and I did fill her full of my cum. I grunted out loud with the force of my ejaculation and I felt her muscles grip me again. I wasn’t sure she had another orgasm but I knew from her expression that I had satisfied her needs. As my cock spurted in her she lowered her breasts against my face. The scent of her perfume and natural scents filled my head. The softness of her breasts pressed against my cheeks as she whispered, “suck my nipples baby,” and I did. Her nipples hardened between my lips and I thrust into her a couple more times with a cock that was quickly losing its hardness.Louise rolled off of me and whispered, “Don’t move, I’ll be right back.” And she left the bedroom. She returned with a wash cloth, had me stand, and cleaned me up from burdur escort bayan our sex. Still naked we sat beside each other on the top of a large cedar chest at the end of the bed. I noticed her breasts that still held their shape with little sag. I knew now where Sherry got her figure.“Larry I need you to understand something. All this wedding preparation has been stressful for me. I know I am not losing a daughter, you know the old cliché about gaining a son. I have also had thoughts of what Henry has missed, and how much I miss him. There are also thoughts that it has just been Sherry and me and now, well I guess I saw something in you today that took me back. As I said, I was soft clay that was formed as well. Henry and I were formed by each other.” Louise stopped for a moment and dabbed a tear in the corner of her eye.I wanted to comfort her yet it seemed strange, a guy wearing his soon to be mother in laws full slip. That same guy just had sex with her and she was naked. “How twisted is that?” I thought. But regardless I put my arm around her and pulled her to me. Her breast slid across the soft nylon slip and I felt her move her head.Without hesitation I kissed her lips. She melted against me and parted her lips to admit my tongue. It was a long passionate kiss that ended with her saying, “All of this today is our secret. I will not allow myself this privilege again. Sherry deserves that same sort of man as her father, ever faithful. I have kept Henry’s secret and will do the same for ours.” And with that she stood and gathered her clothes leaving the bedroom.Our wedding came off without a hitch regardless of my state of mind the rest of the week. Each time we were with Louise I felt like things had changed yet she treated me exactly as she had before having sex. I tried not to give her looks that begged for something to be said yet it seemed that we parted with not much said. Yet I was also worried that it felt like I had cheated on Sherry. The night before our wedding my parents hosted a rehearsal dinner and as part of it I shared a dance with mother and as the music changed she danced me over to Louise. “Larry I think you should ask Louise to dance.” I knew it was the right thing to do so asked and she accepted. I tried not to get too close, but it was a slow dance and I discovered that she was a wonderful dancer. And surprisingly she actually made me look like I knew what I was doing on the dance floor.“Are we okay?” Louise whispered in my ear as she pulled me close to her. Her breasts crushed against my chest and I fought thoughts of that afternoon.“Yes,” I whispered back as we moved around the floor. “I am sorry that I put you in an awkward position.”“I loved my position, especially the second time. But that is not what you meant,” she said quietly as she pulled away from my ear. “You have nothing to be ashamed of, nothing to feel bad about. It was a stolen moment for two people that know the pleasure of the softer side.” She said as the music came to an end. “Never regret those moments,” she said looking into my eyes. “My daughter is going to marry a remarkable young man and I will have a very fond memory to hold deep within me, just like I do Henry’s.”The wedding was a big church affair with all the trimmings yet simple enough to be a real family event. As we formed the receiving line Louise stepped in front of me and looked into my eyes. There was a sparkle there but no admission of guilt or regret. My arms went around her and I felt her ample breasts pressed against my chest as she hugged me. Louise kissed my cheek and whispered, “now I have a son.” I remembered that day as if it was yesterday. Over the years I thought of it often but like Louise I never allowed myself the “privilege” of sharing her bed again. It seemed impossible that 49 years had passed so quickly. In all of those years of being around my mother in law there wasn’t another mention of that afternoon. She kept her promise to keep this as our secret. And I did as well.We had a wonderful loving relationship and she passed away I was as hurt with her passing as my wife. The funeral was behind us and we had been cleaning out the home place. “Just move the cedar chest home,” Sherry had said as she watched me load it onto a furniture dolly. “I will go through it when I am stronger.” I thought of that afternoon, setting beside her on this chest and then felt awkward thinking of a sexual tryst with my mother in law. The chest became a fixture in our bedroom for the past year.One afternoon while alone in the house I looked at that old cedar chest and remembered that afternoon with Louise. Just like that afternoon I had an uncontrollable urge to act on an impulse. To my knowledge Sherry had not opened the chest. Perhaps the reason I opened it was to find a reminder of the woman that had been a part of my life for over 50 years.The hinges creaked as I opened the heavy lid and my senses were filled with the scent of the cedar lining of the old chest. But there was another scent, something from my youngest sexual stirrings. It was the scent of rubber and that faint scent of sachet that women used in those long lost days. It was the sweet floral scent of a woman’s lingerie drawers.Lying across the top of the chest was a dress that I immediately recognized. It was the knee length dress my mother in law had worn at our wedding 50 years ago. I touched the brocade fabric and remembered how it felt on my hands on our wedding day. I was caught in that moment when a polite new son in law hugged his mother in law. But still fresh in my mind then and now was the sexual encounter we had. Now I was kneeling on the carpet and my cock had responded to the feel of that fabric.As strong as the scent of cedar and old sachet was there was the unmistakable scent of the rubber that I knew comes from an old girdle and perhaps a bra. I carefully lifted the dress and there below was the most beautiful blue slip and beside it a classic old panty girdle. The girdle had very long legs with 3 garters in each leg. The center and side panels were heavy satin finish in a very pleasing shape. I immediately recognized the slip and girdle from that afternoon with Louise.At this moment I remembered how Louise had talked about being molded like clay. And even though my shape was molded so many years ago and long since set in a shape, I could not deny that my earliest life’s experiences started me on a journey that was completed that afternoon with Louise. And life had added layers like the glaze of fine pottery. Like glaze on pottery much of the form remained unchanged. None of life’s events had erased the early forming of my inner self.There was no denying that deep inside of me there was a longing for “the softer side” as Louise had called it. Yet as my fingers slid over the silky slip and I lifted the girdle and heard the tinkle of the 6 metal garters, I realized that a special memory should never be spoiled with a moment of impulsive action. I replaced the garments and closed the lid wondering if there would ever be a moment like my first time with Sherry or like that moment with her mother. Both were such important experiences that molded this 71 year old man into what he was today.

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