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My love of cross-dressing began at an early age, barely over sixteen. We were a family of three, Mom, my older sister Beth, and me. One of my chores was doing the laundry. It was a laundry day, and I was home alone. As I sorted the dirty clothes, I came across a pair of Mom’s panties. She did not, as a rule, put her lingerie in the clothes hamper. I assumed that she had put them in the dirty clothes without thinking. The panties were purple and felt very silky. My sister’s lingerie was usually in the dirty clothes, along with the rest of it. I had worn Beth’s panties many times, but mom’s just seemed somehow different; perhaps it was the dried stain in the crotch.

Without thinking, I brought mom’s soiled panties to my nose and sniffed them. The aroma was much different than that of my sister’s. Unlike anything I had smelled before, but I did notice my cock getting hard. I am not sure, but I think in that instance, I decided to put them on and see how they felt.

I dropped my pants and undershorts to the floor and slipped the panties on. I was thrilled as I pulled them up on my legs, and the feeling of them once I had them on was unbelievable. My hard cock stuck out the top of them, and I decided to try on some more Mom's clothes. I left the laundry room and rushed upstairs to Mom’s room, wearing just her panties.

I found a full slip hanging in her closet, it was black and felt silky. I raised the slip over my head and slid it down my body. I felt like this is what I should be wearing. I put on a pair of her three-inch heels, and soon as I could walk in them, I pranced around her room and preened in front of a full-length mirror. I felt terrific; my cock was was harder than it had ever been and throbbing. I began masturbating, and when I lost a load of cum into the panties I decided I should finish the laundry.

I hung her slip back in the closet, took off her shoes, and went back down to do the laundry, once again wearing just a pair of panties, but now they were soiled with my cum. I finished the laundry. Every laundry day after that was a repeat of trying on Mom’s clothes, except now I started wearing more and more. I was soon using lipstick and make-up.

Then one day, about six months into my cross-dressing adventures, what I thought could be the worst thing that could happen, happened. I was dressed in a pair of panties, nylons, a black mid-thigh skirt, and a white satin blouse. I had just finished applying make-up when I saw a movement out of the corner of my eye. I spun around toward the door, and there stood Mom.

I started stammering, trying to come up with why I was dressed like this. With a smile, Mom asked, “Is this the way you feel you should dress?”  

Looking at the floor, I murmured, “No.”  

“I see,” she said then asked, “Why then are you wearing my clothes?”  

I gathered all of my courage and looking in her eyes, I said, “Because it feels good.”  

“Yes, I understand you enjoy wearing them,” she stated. Then asked,’ “Does it make you feel like you are a girl?”  

“I don’t know. I just like the way it makes me feel.”  

With that, she told me to sit down, and she stripped all of her clothes off. She stood naked in front of me and said, “This is what a girl looks like. Even though you can wear girls clothes you are not a girl. Now take my clothes off and put yours on as I go down and start dinner.”   Mom then redressed and left the room.

During dinner and the rest of the evening, Mom would look at me with a sight smile. She winked at me several times when my sister was not watching. The next day was a Saturday, and my sister went to one of her friends’ house where she was going to stay for the weekend.   Mom told me we were going shopping. On the way to the stores, Mom said to me that we were going to buy some girl clothes for me. We purchased six pairs of silky bikini cut panties in assorted colors and then six pairs off silky thongs, also in assorted colors.

We got slips, and half slips, sundresses, nylons, a pair of three-inch heels, a pair of two-inch heels, and a pair of penny loafer type shoes. Then we went to Victoria’s Secret and got me several sets of sexy loungewear as well as sleepwear. Then we went to another store and got me three different shades of lipstick, nail polish, mascara, and two bottles of spray-on cologne. I am sure the excitement I was feeling was showing in my eyes, and soon as we got home, I ran to my room with most of my treasure. Mom followed me with the rest of my shopping booty.

I was laying everything out on my bed, trying to decide what to put on first. Mom reached into one of the bags she was carrying and brought out a bottle of body hair remover.

Mom held out the bottle to me as she said, “If you are going to dress like a girl, you must also groom yourself like a girl. Take this into the shower and remove all of your body hair. You can keep some in your groin area if you like but trim it well if you do.”

Mom left the room, and I hurriedly stripped off my clothes, and excitedly went to the shower. Following the directions on the bottle, I removed all of my body hair. I marveled at how good it felt to not have body hair. When I got back into my room, Mom was sitting on my bed waiting for me.

“Now,” she began as she held another bottle to me, “you need to moisturize your skin. Use this lotion and rub it all over your body. I will help you if you wish...

I took the bottle, and she noted that I did not know precisely how to begin. She took the bottle back and poured some lotion into her hand and first rubbed it onto my face and neck then she went to my neck and chest, she had me turn around and covered my back, buttocks and the back of my legs. She had me turn around again and started finishing my front side.

I started getting hard when she massaged the lotion onto my buttocks, and when she lingered with a finger on my hole, it did not help. As she rubbed my front, she slowed down and cupped my balls as she leaned forward and kissed the head of my cock. Of course, my cock leaped and, in so doing, landed in her mouth. I do not know for sure if Mom had intended to suck me off, but she did. After I shot a massive load of cum into her mouth, she dropped my cock from it and swallowed all of it.

She licked her lips, and then said,” There, that is taken care of; we cannot have your hard cock stretching your cute new panties.”

She then stood up as she said, “You go ahead and dress. When you finish, call me. I have a surprise for you.”

I dressed, first a black thong, then a pair of thigh-highs. A padded bra, a full white slip, and a yellow sundress. Last I slipped on a black pair of three-inch heels.

When I finished, I admired myself in the mirror and called for Mom. Mom appeared in my doorway and told me to come to her room.

When we got to Mom’s room, she had me sit down at her vanity, then she produced a wig. The hairpiece was shoulder length and auburn in color. Mom had the bag with the lipstick and mascara sitting on the vanity. She slowly applied the mascara as she explained how I should do it. She used the dark maroon lipstick on my lips and then fit the wig to my head.

When I looked in the mirror, I stared in disbelief. Staring back at me was a gorgeous girl. My mom patted me and said, “Tomorrow, we will learn to use nail polish. You are very beautiful now as you are and I will start treating you like another daughter. Your sister will not be home until Sunday night, and in the meantime, you can live as a girl, if you wish.”

The rest of the day and evening, we spent as a mother and her daughter. Mom hugged me at times, and I just melted when she did. When it got to be time for bed, Mom told me to go put on one of my sexy nighties. I put on a purple, sheer baby doll, I felt very girlish and sexy and went to show Mom.

Mom gasped slightly when she saw me. She hugged me and said, “Baby, you are gorgeous.”

I beamed and felt my cock start to stiffen. We went upstairs arm in arm with me not wanting this fabulous day to end. When we got to my room, I think Mom could sense my reluctance to leave her.

She hugged me as she said, “Baby, you can sleep in my room with me if you would like.”

Of course, that brought all of my happiness back as I agreed.

We got into her bed, and she held her arms open as she said, “Come here to mama, sweet girl.” I rolled into her arms, and we held each other tightly. I tried to maneuver my body so she would not feel my hard cock. I failed as both my hands landed on her tits, one in each hand. My leg slipped between hers. Now I have a tit in each hand. My leg is between hers, pressing on her mound and my hard cock poking at her belly.

“Oh, my sweet baby girl, it feels like you may not want to be a girl after all ,” she gently said.

“I’m sorry, Mom. I just can’t help what is happening, but I do really want to wear sexy girl clothes.”

Mom kissed me lightly on my lips and whispered, “That’s okay sweetie, you can be Mommy’s little girl whenever you wish to be. But right now, we are going to have to take care of your boy parts.”

Mom kissed me again, but this time she licked against my lips. I parted my lips, and her tongue entered my mouth. I gently sucked her tongue as she moved her body around a little. I was lying on top of her, and mom spread her legs apart as she reached between us and took hold of my hard cock.

She guided my cock to the entrance of her pussy, and my instincts took over. I pushed against her, and my cock entered her very wet and warm tunnel of pleasures. I slowly sank my cock into her until I was balls deep in her pussy. Mom wrapped her legs around me as she murmured, “That’s it baby, fuck your mommy. Shoot your boy cum into the womb that you came from.”

Then holding us tightly together with her legs and arms wrapped around me, she began grinding against me. As we ground against each other, my balls tightened, and I felt my cum entering my cock shaft. As I started cumming, Mom shrieked and clasped her legs around me even tighter. As she climaxed, her pussy tightened around my cock, and I began shooting my cum into her. I do not know how many spurts of cum I shot into her, but it was several.

We kissed as we held each other, enjoying the afterglow of our lovemaking. As we held each other tightly, my limp cock was plugging Mom’s pussy, and it was not long before it began to stiffen again.

Once my cock was again hard, I began to slowly pump in and out of her as we kissed. As I slowly fucked Mom, she made soft mewling sounds each time she had a mini climax. She had several mini orgasms, and as they gained in intensity, she mewled a little louder. I pumped in and out of her pussy for at least twenty minutes, probably longer.

When I felt mom pushing back against me a little harder, I increased the tempo of my cock plunging in and out of her. Soon I was pounding on her pussy mound very hard and fast. Mom was now panting and mewling very loudly. As I felt my sperm rise in my cock, I slammed it as deep as I could into that beautiful pussy. Mom shrieked very loudly as her legs flew around me, holding me tightly there.  

Once again, I gave her many ropes of my cum before collapsing on top of her. We kissed as we held each other, and eventually, my cock was limp, there was a loud, juicy pop when I pulled it out of her well-fucked wet pussy.

We kissed and caressed for a while and fell asleep in each other’s arms.

I awoke the next morning, alone in the bed, and I could hear mom in the kitchen. I left the bed and went to the bathroom, looking in the mirror. I saw that my lipstick was smeared, and my mascara was a mess. My wig was twisted on my head, and I took it off. I washed up then put my hair back on. I decided not to use make-up on my own yet and went to my room. I put on a lilac-colored teddy and a pair of slippers then went downstairs.

I walked into the kitchen, and Mom sat a cup of coffee on the table for me. She had a radiant smile as she said, ”Good morning, sweetie, I see you are a girl again today.”

I looked at Mom; sheTo continue reading this story you must be a member. Join for FREE here.

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Hi ISS readers, I am a regular reader to ISS stories somehow I felt most of the stories are fake, I fail to understand how can one make 5 times love in next 2-3 hours. Anyway I am hardly concerned about this. Let us straight come to the incident. I still remember I was sick my age would be around 18 and suffering form high fever. I used to sleep in my room. My mother came to see me when she touched my head and realized that I am suffering from very high fever. She just slept beside me to take...

Incest
3 years ago
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Hot Office Sex

company, I was the only one there. I had some more work to get done and didn't want to work on Saturday. I like to wear sexy clothing, but its not allowed during business hours, so I bring a change of clothes to work with me. That night I was wearing a real tight mini skirt that was quite thin and a little transparent and sat low on the hip. I was wearing a black thong underneath. I had on a light skimpy spaghetti string top that was also transparent and fit high enough to show my...

4 years ago
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Obedience Training

Please read other chapters first. Thank you!http://xhamster.com/user/Leaflee/posts/124721.htmlhttp://xhamster.com/user/Leaflee/posts/125875.htmlhttp://xhamster.com/user/Leaflee/posts/127435.htmlAfter sleeping some, Master said it was time for my obedience training. My collar was tightened around my neck and I was given instructions to put on the sluttiest outfit in the closet.I fretted somewhat checking the variety of the wardrobe. What I deemed slutty may upset the Master. I quickly decided...

2 years ago
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Thicker Than BloodChapter 6

2001 I was impatient for the lady to call me. The school was small, but that’s what we, Stacey and I, were looking for in a high school. No public school for our baby, well she wasn’t exactly a baby anymore, she was thirteen, gonna be fourteen soon. “Mister Carter?” she called. I rose from the waiting room seat I’d been occupying and went over to her. She handed me the papers: Jenna’s class schedule and a short list of other things we had to get taken care of: the standard health clearance...

3 years ago
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No Angel

I am no angel, and neither have I ever claimed to be one, but this was right on the edge of legality, at least as far as our present society sees it; evil... ? I don’t know, how do you quantify evil? I mean, I am not hurting anyone, am I? Her mother had said that she was a virgin, just turned fourteen, already started bleeding. The girl, herself, couldn’t tell me her age either, she was functionally illiterate – and I’m not certain that her mother was any better. The man of the house,...

4 years ago
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Bombay Dreams

Hi… Sometimes there are stories, which one would like to keep under covers and yet the sweetest incidents often turn sweeter when memories are told to friends and shared under the blanket of a pseudonym. First I accept you as a friend before sharing this memory with you. This sweet tale is of Sangeeta a pretty young woman who worked in my house in Bombay (now Mumbai). Back then I was just 20 and filled with dreams of love and yet Sangeeta till then had never been a part of my dream. Strange...

2 years ago
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Carnival II

Carnival II by C.J. Wenhurst It was five years since the big pier hosted the flickering lights of the huge carnival rides and the smell of cotton candy. The official start of summer was just a mere two weeks away. New colorful advertising signs were posted all through town on phone poles, in grocery store checkouts and even appeared on broadcasts of local radio stations, inviting the general public to the upcoming big event. "The Carnival," the signs read,...

3 years ago
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SEX IS LIFE AND ENJOY

I LIKE WOME I LIKE SEX WITH THEM FEEL DREAM FEELING WHEN HAVE SEX WITH THEM DESPITE I MA NOT DOING IT WITH THEM ALWAYS TIME TO TIME BECAUSE MY POOR SITUATION OF NOT HAVE MONEYS AND TO FOR MY SMAL COCK 13 CM FEELING ME THAT WOMEN NEED BIG COCK WHO IS OPEN THEIR ANAL AND THEIR ASS AND THEY FEELING GOOD OF BIG COCK .BUT AFTER MY SEE THAT IS THEIR FEELING IN HOT SEX FIND IN THE FIRST OF THEIR ANAL WHO ARE FEELING GOOD SEX .I LIKE SEX DOING ALONE EVERYDAY IN GENERAL .ENJOY AND HOT INSIDE ME AND THAT...

3 years ago
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Stacies Mom

"No Mark you cannot go out on a date with this Stacie Girl: I have never met her OR her folks and don't want you getting in some kind of trouble." Luke Barrister said from under the body of the 89 Buick station wagon he was working on while his younger brother Mark and younger sister Wendy asked him if Mark could go out with Wendy's new friend Stacie Downs. Luke had been reluctant enough to let Wendy hang out with her at the mall, that was at least a public place and Wendy was the more...

MILF
2 years ago
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WHATEVER HAPPENED to ELLIE Part 2

When I dropped Ellie off at her Mom Helen,s she came out clutching a set of keys. “Got the keys to our cottage at the Lake. Mom hardly ever uses it now Dad,s dead so we can fuck I disturbed out there and also go for a swim.” She Tod me as she slid close on the passenger seat. “Don,t have my swim trunks with me.” “Who bothers with swim suits silly?” She laughed, fished out my hardening penis and started playing with it. It was stiff as a board by the time we parked in front of their “cottage” a...

4 years ago
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No stupid cunt

A city, somewhere, dawn The boys were breaking up after a night out. Stephan, barely standing, was elucidating to all who listened on his sexual life. Nobody listened, the drunken boys staggering forward in silent determination not to take to quadruped locomotion. They had spent their ticket fare on White Lightning - public transport was soooo overrated ... - I can fuck shree times ... no ... four timesh ... yeah four timesh ... every time ... and in the morning ... twish ... I...

2 years ago
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The Widow Ch 20

Passion in James County XII The Widow By D.C. Roi Chapter twenty On the way back to the lake, the women steadfastly resisted every attempt the men made to find out which of them was going to get the surprise. As he and Joanne walked back to Fran’s house, Larry looked at the packages Joanne was carrying and wondered if he was the one who might be getting the surprise. She did have quite a few packages and, as they neared Fran’s house, he found himself looking forward to finding out what was...

1 year ago
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Group Fun

We had gone for a holiday trip to switzerland n had already booked a luxurious hotel. We had fun at playing pool. Than w went to our room i and my 2 frends. We were enjoying every moment. we also came to know that priyanka chopra is here. v started imagining her n talked dirty. Suddenly someone kncked at our door. To my surprise it was priyanka in her nity that was jst some 2 inch below her ass.She came in shouted on us n told wat the fuck rubbish we were talking abt her. I told her sorry for...

Group Sex
3 years ago
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Getting Help With My Story

So, after dating a new girlfriend for a couple of weeks, I started to show her my stories. Linda actually read the first dozen or so and didn’t leave the room running. I took that as a good sign. “So, did you like anything I wrote?” I asked cautiously. “Um, yes…I think some of them are funny,” She started, “I just read the one where you say Grace. Did you really do that?” “Hey I’m a Catholic boy, I was taught to say Grace before I eat.” I answered honestly. “A good Catholic...

3 years ago
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Becoming Traditional

"Becoming Traditional" by Geode Jack's life could never be described as "traditional". He was raised by a strong mother and three harsh older sisters. Being Married to a woman that was an electrician that owned a very large and successful contracting company. Even his work was untraditional, being a man in the predominantly female Social Work profession. Although all that changed on his Silver Wedding Anniversary second honeymoon. I was born nine days after my father's death in...

4 years ago
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Please Part 2

Thursday afternoon, 4:00pm, the time had a significance for her, especially now. She looked forward to the liaisons, her body ached for them, the anticipation made her wet. She had a routine here, but didn’t know what to expect. As were her instructions, on arrival, she removed her clothes, took her place in the room and waited.The majority of the room was dark, only the one familiar light from above. It comforted her. The room was large, so large that under the single light, she could not tell...

Group Sex
1 year ago
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NuruMassage Lilly Bell The Arousing Race

Lilly Bell and Codey Steele run into a massage parlor and take a moment to catch their breath. There is some tension in the air as they soon start to bicker, each laying the blame on the other for getting lost on the way here. It turns out that Lilly and Codey are a married couple who are part of a special race that involves visiting local businesses to complete challenges. This massage parlor just happens to be where they will complete their next challenge, which is to use an ENTIRE bottle of...

xmoviesforyou
3 years ago
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A roll of the die Part Two

((continued from part one here, )) Karen managed not to laugh and kept her tongue slipping up and down Lisa’s pussy. Lisa shifted and Karen looked up to see Lisa turn her head to the side and stuff Jeremy’s long hard cock into her mouth. Karen felt Dave’s fingers smoothing the edges of her pussy and she purred her delight into Lisa’s. It was official, she thought. It had become an orgy. The pleasure his fingers sent into her depths fed the alcohol coursing through her veins and Karen...

Group Sex
2 years ago
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Day With Drugged Mom

Firstly I would like to give a description of my mom and me. My mom is 44 years old and I am 17 years old. I am 5 feet 9 inches, lean and muscukar body while my mom is an average indian housewive 5 feet 4 inches with an incredibly hot figure. This experience of mine is about 6 months old and I could not wait to submit it. It was a normal sunny day and my mom was working the daily chores. She had not taken a dupatta and whenever she was bending or doing something, I could have a complete view of...

Incest
2 years ago
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Bla Book 6a Jurassic Bed BreakfastChapter 18

Frank stopped in his tracks, staring at the sweet young girl holding that murderous tool in her hands, not believing for an instant that she truly wanted her sweet, sexy pussy turned into chunks of raw, bloody meat. He could see almost every inch of her petite, well-formed body right through the transparent nylon cat suit that she pretended were her clothes. Still on her knees, Vanessa held the mangler up higher, stretching her sexy body toward him almost worshipfully, imploring him to...

3 years ago
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Sex With Beggar Worker In ATrain

Hi Friends I am Tanvi. I am here to narrate my real life experience which happened me in a train journey (Excuse me for my English in this story) .I am engineer by profession and a keen reader of Sex stories. It is evident that we all have some kind of sexual experience which does not fit the normal criteria. I have born in Delhi and belong to upper middle class family. When I was 8 yrs. old I was sexually abuse by my cousin. I was unaware of such things and he took advantage of my innocence in...

2 years ago
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The Witch and the Dragon Part 5

Toeing off her glass heels, she bit her lower lip wondering what he was going to do next. She didn’t need to wait long when he gripped her arms and hauled her out of the Viper. Zak was not very gentle when he simply gripped one arm and hauled her after him toward the tower. She could barely keep up with his long strides, and by the time they dropped into a damp hole in the ground and made their way up into her old tower room, she was sobbing. He pushed a door she never knew existed in her...

Supernatural
3 years ago
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The HeirChapter 13

We damn near lost Remus as well. It happened the day after I checked the freezer in the garage and saw that we were down to less than thirty pounds of buffalo meat. Our twin hunters decided it had been long enough since the ranger was poking around, and that it was probably safe to take another deer. I told them I was getting ready to order another buffalo from the ranch in Wyoming, but that I’d hold off to see how they did on their hunt. The next morning, they left the cave through the...

4 years ago
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Poor Rob

There were times when it sucked to be me and in the last three years those times had been too damned frequent. As I sat at the bar in my favorite night spot and nursed my beer I did have to admit to myself that I brought a lot of those times down on me on my own. I seemed to have the world's best AND worst taste in women. Best because I always seemed to come up with the great looking ones; the ones with personality to spare and who were fun loving and a joy to be with and who usually grabbed...

4 years ago
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It Just HappenedChapter 7 Having the talk

The next day I got up early and sent a fax. "Miss Spencer, I hope you enjoy a Happy Thanksgiving, Ben." The words we overheard when Jen was talking to her sister, "I can't. I just can't sit at that table and pretend... ," haunted me. Was she saying she couldn't sit at her parents' Thanksgiving table and pretend that the man she had given her virginity wasn't there? Was she saying she couldn't pretend that she didn't love me? Millie, I decided, was the only person who could tell me...

3 years ago
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Introducing Miss DriscollChapter 2

Two weeks had passed since Miss Driscoll’s sex education assembly and, like most of her 14 year old classmates, Molly had thought of little else. For them, it had been a period of illumination. The girls, none of whom had previously admitted to masturbating, would now openly swap tips and experiences, giggling in the corridors as they regaled stories of their first orgasm, what they were thinking of and, in one case, which family member had caught them making innovative use of an electric...

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