Crosdressing Stories

Crosdressing Stories
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Created:
Monday, 28 February 2011
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  • anon7a, Fictional or Non-Fiction that is one hell of a story and is very easy to picture it in our minds as we read it. I really enjoyed the story.
    groups.wall 115 days ago
  • Berkie's Mom is an original story I wrote as SSDaly back in the late 1990's and posted on a few sites.

    The story is ficional but my own work. I hope that you enjoy it.

    Maybe Rikki can make it into a movie
    groups.wall 125 days ago
  • Berkie's Mom

    When I was a teen-ager in the 1960's I spent a lot of time at
    Berkie's house. Mom was dead and dad had gone to Canada to work and
    left me and my two older brothers to take care of ourselves on the
    small farm that dad had inherited. We got money occasionally, and we
    three took pretty good care of ourselves. I spent most of my time at
    Berkie's. We would ride motorbikes, play cards, or games, and do other
    things that teenagers do.

    Berkie's mom was a lovely woman that was always cheerful and
    made me feel welcome, no matter of the day or time of day that I was
    there. It was like being home. Sometimes, she would give me hugs along
    with Berkie if we were all having fun together. I would often eat with
    them, if I was there for mealtime, and Berkie's mom always made me
    feel special. She paid special attention when I talked and rather than
    just nodding in agreement, asked questions and challenged me to back
    up what I was saying and the like. I guess that she was as much of a
    friend to me as Berkie was. Maybe she was just trying to give me
    something that I didn't have at home.

    Berkie's family lived in a mobile home on some acreage near
    our house. Between us there was several hundred acres of pasture that
    Berkie's dad owned with a partner. The nearest neighbors were more
    than two miles away. Berkie's place had a home built addition that
    made a living room an extra bedroom and a second bathroom, larger than
    the one in the trailer part... His dad had some stock, and farm
    machinery for hire, and spent considerable time away working or on
    buying trips, leaving the care of the animals to my buddy and his mom.
    I occasionally helped with the chores, although I preferred running
    the machinery to shoveling manure.

    I would usually knock when I went over to visit, and wait for
    someone to open the door. One day I went over to Berkie's house to get
    him to go out on the bikes, and knocked as usual. There was no answer.
    For some reason, I don't know why, I went in anyway.

    I looked around for Berkie or his mom, and waited for a while.
    I had to take a leak, so I went back to the bathroom. After I was
    finished, I was looking around and saw some clothes laying in the
    corner near the linen closet. I picked them up and noticed that they
    were Berkie's moms underpants and bra. The underpants were like boxer
    shorts but stretchy. There was a little rose on the waist There were
    nylons attached to some hook things. They smelled perfumy and had a
    faint yellowish stain around the part where the legs come together. I
    sniffed at the pants and the stain and became very aroused because of
    the mixture of perfume and body odors. My dick began to swell and ache
    as I sniffed the pants.

    I was complete engrossed in the feel and smells of Berkie's
    moms underpants. I was very hard and bound up in my shorts so that I
    was in pain.

    Suddenly I heard the front door closing and Berkie's mom
    coming in the house. I quickly put the clothes back. My mind was
    racing, I didn't know what would happen if I was caught in their house
    without being invited in.

    Without thinking, I flushed the toilet and walked out to the
    living room, where Berkie's mom was straightening up. She turned and
    saw me. She looked like she had just come from town. She was wearing a
    dress and nice shoes. Some bags of stuff were on the kitchen table.
    Berkie's mom was a good looking brunette with a very pleasant smile
    and deep green eyes, that twinkled when she smiled. She always dressed
    well, in skirts when she was going to town or working in the house,
    but also looked good in jeans when she was doing chores.

    Bobby, I didn't know that you were here.

    I came over to see Berkie. I knocked, but no one answered. I
    needed to go so I came inside to use your bathroom.

    "Oh, O.K... Berkie's not here. He went with his dad to look at
    some machinery in Turley. They won't be back until late tonight."

    Then she said, "How about staying and helping me with feeding
    and watering the animals. I need to change first so just wait here." I
    nodded and she left and went back into the bedroom.

    I sat on the couch and started reading a magazine. It was a
    farm journal talked about crop reports and other stuff. I put that
    back and picked up another magazine. It was called Cosmopolitan. It
    had pictures of women and women's clothes and other things. Flipping
    through it I saw a picture of a lady in her underpants and bra. They
    looked like the same kind as Berkie's mom had, except these were light
    blue. I was fascinated by the picture and was suddenly startled by
    Berkie's mom's voice calling out, "Bobby, could you come and help me
    for a second."

    I got up and went back toward the voice. Berkie's mom was at a
    closet putting some things on a hangar. She came over to me and said,
    "Bobby, could you undo the top button on this blouse, I sprained my
    shoulder a little while ago putting the groceries in the car and cant
    reach it now." She turned around, and I reached up to undo her button.

    My hands were trembling, and I didn't know why. I fumbled
    around for a few seconds and was able to make my fingers undo the
    button. It was the last one and the blouse slipped down off of her
    shoulders. She caught it with her arms, and said, "Thank you, Bobby".

    She looked at me strangely and said, "Bobby, are you all
    right?" You look flushed.

    I - I... , I stammered.

    Oh, I know, you're embarrassed to be here, aren't you?

    I nodded.

    Well take it easy, here, sit down for a while and talk to me.

    I sat down on the bed and stared at the floor. Berkie's mom
    began talking about her trip to town and so on. I guess I wasn't
    paying attention. I was still staring at the floor and then I heard
    her say, "Bobby. BOBBY"

    Yes? I replied.

    "This shoulder really hurts. I need you to rub some Ben Gay on
    it. Could you do that for me. It's back on my shoulder blade where I
    can't get it."

    She slid her slip off her shoulder and let it down. She also
    let her bra strap down so that her shoulder blade was fully exposed.
    She handed me the ointment and I put a little n my fingers and started
    to rub it into her shoulder.

    "Oooh, that feels good, thanks Bobby."

    I continued to rub the shoulder. I noticed that her face was
    becoming red and her breathing was becoming a little erratic. Please
    rub that a little lower, below the blade, that's it. I didn't realize
    it until then but her slip was on the floor and she was sitting there
    in her underpants. They were pink with little pink flowers all over
    the back shiny part. She had on stockings that were hooked to the leg
    part.

    "Bobby?"

    "Yes?"

    "Why are you staring at my legs? You've never seen a woman in
    her underwear before, have you?

    "No," I said quietly.

    I'm sorry. Do you want to leave? I guess that I just assumed
    that since you was always her with Berkie, and we are such good
    friends, that this wouldn't bother you. I really needed your help.

    I. Just feel funny, you know.

    Oooh. I see.

    I guess she noticed then that I was hard down there.

    She stood up. Bobby, look at me. "This is what women wear
    under their clothes. She pointed to her chest. This is a brassiere or
    bra. We use them to hold up our breasts."

    She pointed to her middle "This is a panty girdle" It helps me
    to hold my tummy and bottom and holds my stockings up.

    She pointed to her nylons. These are nylons. They help our
    legs look pretty. See the way that the stockings are held up, these
    are called garters.

    I stared at her as she gave her guided tour of her underwear.
    She turned around to the dresser so that her shiny butt was facing me.
    I don't know why, but my hand reached out to touch the shiny material
    on her bottom. Berkie's mom let out a yip and spun around.

    I'm sorry, I guess I should go outside or something, I
    muttered.

    "No. No, you just surprised me that's all. Do you like the way
    that the fabric feels?" she asked.

    I nodded.

    She took my hand and pressed it against her tummy. My fingers
    moved around the front in a circular fashion. The front was shiny like
    the back but also had some flowery fabric around the edges.

    "Do you like that?" she asked, "It's called lace and it's
    pretty. Women like pretty things, and men do too!"

    "Look here!" She said, opening her dresser. "Women have lots
    of things to wear, to make us look pretty."

    She pulled out some underpants that were flimsier than the
    ones she wore.

    "These are panties. Your girlfriends in your senior class
    probably wear these because most teenage girls don't need a girdle."
    "I wear them under jeans, or with a girdle like this one. She pulled
    out a girdle that looked like the one she wore, but without any legs.
    "You hook the stockings to these just like my panty girdle." She
    showed me her garters again.

    I looked at her in bewilderment. She didn't think that I wore
    those things? I hadn't even seen them before.

    As if she read my mind, she blurted out, "I didn't mean you,
    but I meant 'you' as me - Oh, you know what I mean!"

    My mind was racing! What in the hell was I doing here? What if
    Berkie's dad found out about this? I would be dead, that's for sure.
    He would probably kill me with his bare hands, like a chicken.

    "Still, you know," she pondered, "don't you ever wonder what
    something would be like? Do you ever want to do something, just to try
    it?"

    I stared at her in utter disbelief! Why was Berkie's mom
    talking to me like this? What the hell did she want me to do. All
    through this, I couldn't take my eyes off of her girdle. I thought
    that I could see a dark patch between her legs that looked sorta like
    the hair around my dick.

    "Bobby, would you like to try on my girdle?"

    I completely lost my breath! I gasped for air, and my heart
    felt like it was about to explode.

    "No. No!"

    "Bobby, are you sure?"

    "Well, maybe. Just to see - see what it was like." Things were
    completely out of control by then.

    "Here, let's try this. First, you can take my girdle off of me,
    and then, if you want, you can try it on for yourself" She took my
    hands and put them on her waist. She stopped, and bit her lip as if
    thinking. "No wait, I have an idea. You need to know this when you
    have a girlfriend."

    She sat on the bed and put my hands on her legs. "First, take
    my stockings off," She commanded. She pulled up the leg band on one
    leg of the panty girdle and exposed the garter that was holding the
    stocking. "Unhook it in front and in back" I fumbled with the front
    garter. I couldn't get my fingers to work.

    Berkie's mom took my fingers and gently guided them through
    the motion so that the garter released the top of the stocking. "now
    the other side" After a few seconds, the second front garter was free.

    She stood up and turned around and said, "Now do the back
    ones." The garter thing was becoming easier with each one. Soon all of
    the garters were undone. Berkie's mom sat back down on the bed. "Now
    you can take the stockings off me."

    As I reached for her stockings, her legs parted slightly and
    the middle of her girdle sort of popped open. I saw dark curly hair
    and a bright pink area sort of in the middle. I could smell the same
    smell that I had noticed from her underwear in the bathroom.

    I couldn't believe it! There was Berkie's mom's pussy right
    there. I had never seen a girls pussy before, but there was no mistake
    from the talk among our friends at school, that this was it. The
    realization of what was going on finally hit me. Here I was with
    Berkie's mom, in her bedroom, taking off her underwear.

    "Oops!" she squealed, "Sorry, I didn't mean for that to
    happen."

    Things were so far out of control by now that I quit thinking
    about the situation and just followed her instructions.

    Berkie's mom stood up and took my hands and placed them on her
    waist for the second time. "Now, you can take off my girdle," she
    said, "take the waistband and pull it down over itself." I tugged and
    pulled without success.

    "They are supposed to be a little tight," she assured me,
    "just pull down a little harder." I pulled down with more force and
    the fabric stretched out and began to roll over her haunches and down
    her thighs. As I pulled down my head came closer to her tummy. Her
    smell was very noticeable now and it seemed to be warmer near her
    pussy. For some reason, I stopped, and looked at her pussy. The
    crotch of her girdle was right below it, and it was wet. I leaned
    forward a little and stuck out my tongue to taste the wet spot of her
    crotch. Both of her hands gently held my head and pulled me up from in
    front of her.

    "Not now," she purred. "You still have something to do."

    My dick was aching, and my balls began to hurt. "How much of
    this could I endure?" I thought.

    She made me remove the girdle the rest of the way and had me
    stand up.

    "Now it's my turn," she said. Kneeling down, she took the
    girdle and folded it down over on itself so that the top half of it
    was folded out over the bottom half. "Lift up your leg," she said. I
    complied, and she slid the leg of the girdle on to above my knee. "Now
    the other one," she said. The stretchy fabric felt strangely
    pleasurable as it went up over my legs. She pulled the girdle up so
    that my balls touched the wet crotch of her girdle. It was cold by
    then and my balls pulled up a little. Unexpectedly, she leaned over
    and put her lips on the end of my dick. She then used her tongue to
    tease my knob. The result was an immediate hardening of my already
    stiff dick. I couldn't believe how good, and yet painful this all was.

    She then pulled at the waistband and rolled the girdle the
    rest of the way up over my butt and straightened it up so that it was
    in place like the way that she wore it. It didn't seem as tight as
    when it was on her, but the stretchy fabric felt good and some
    pressure was being put on my hard dick by the front panel. This
    offered some relief and I was able to regain some of my now erratic
    train of thought.

    "THAT is how you put a girdle on!", she said matter of factly.
    "Boys and men don't really know that, as well as many women. They
    think that you just pull it on like shorts or socks. The problem is
    that the stretchy fabric fights you all the way like that. Spend a few
    seconds getting ready, and folding it over and it's a lot easier."
    Berkie's mom was just chatting away like I was one of the girls,
    naked, except for her brassiere. I think that I was staring again,
    because she suddenly stopped and said: "Oh, we need to put stockings
    on you. I hope that they fit." She took her stockings and pulled them
    up my legs. She made me do the garters again, though. "You need the
    practice," was all that she said.

    She stood me up and looked at me. "You look beautiful!" she
    squealed. She turned me to the mirror on the closet door so that I
    could see. I looked ridiculous! She was standing behind me, and took
    my hands and ran them over my girdle encased butt and thighs. Ran them
    down to my legs, and inside to my crotch. Ridiculous looking or not,
    it felt terrific. She was watching me in the mirror as she guided my
    hands to stroke my dick through the tummy of the girdle. The outline
    of my dick was very distinct in the mirror. I felt a surge of
    hardening down there again. As she guided my hands over the girdle,
    she whispered, "Feel that. Doesn't that feel sooo good?" Our hands
    wandered over the girdle again and again. The cold wetness of the
    girdle crotch had warmed up and was now just wet on my legs and balls.
    It felt very erotic.

    She was looking at me in the mirror when she exclaimed:
    "Brassiere! You need a bra!" She quickly turned around and said,
    "Here, take mine off, and I will help you put it on."

    I fumbled with the back for what seemed like an hour. Finally,
    the bra fell away. I don't even remember how I did it.

    She turned around , braless, and said "Here now, this will
    complete the ensemble". She helped me put the bra on and hooked it
    from behind. She turned me around to look at me. "You are going to
    need something to fill those up," she said. She then pulled some
    stockings from her drawer and pushed them into the cups of the
    brassiere.

    There I was: a pimply faced teenager dressed in a bra and
    girdle, with my best friend's mom naked in her bedroom!

    "You look so sexy!", she said after a moment. She reached
    around from behind me and began rubbing my girdle encased dick. "I
    could just eat you up!"

    She pushed me from behind, and I lost my balance and fell over
    onto the bed. She fell on top of me. I was lying face down with her
    hand underneath me, Berkie's mom was on top, and I was struggling to
    breathe. As I struggled to turn over, my eyes met hers, and I stopped
    for a minute. I kissed her on the lips, cautiously at first, and then
    more forcefully and for a longer time, like in the movies. I felt her
    tongue push past my lips and flicker against mine. I was kissing
    Berkie's mom!

    We necked for a long time. Her breath was sweet and her lips
    ere very moist. Kissing her was very pleasant and made me feel warm
    all over. While we were necking, her hand kept rubbing my butt and
    stroking my dick inside the girdle that I was wearing.

    She was still sort of on top and got up on her knees while
    still straddling my body. "Now it's time," she said as she worked her
    way up so that her pussy was near my face. "I need you to kiss me now,
    right there." She pointed to her brown patch of hair.

    I raised my head up to her crotch and started kissing her
    bush. The odor was unbelievable now since she was obviously excited
    and very wet. I stuck my tongue out to lick the patch and felt
    something underneath. I was soon licking at her parted pussy lips. The
    salty, and slightly fishy taste was new to me, pleasant, in a strange
    way. Since this had never happened to me before, I didn't know what to
    expect.

    "Keep licking sweetie!" She purred. She held my head in her
    hands and guided my tongue around until I was where she wanted me, and
    she began working her crotch against my face. After a few moments, she
    stopped and got off of me. She lay down on the bed again, with her
    head pointing towards my dick, which was still hard, still in pain and
    still in the girdle. She laid herself sideways and raised one knee so
    that I could keep licking her pussy while she began to rub my dick
    through the girdle again. Using her hands, she raised my leg up so
    that the crotch opened up. My aching balls popped out, and she began
    to lick each one gently and finally took one , then the other into her
    mouth and gently sucked on each one in turn. She used her tongue to
    lick along my crotch, along the base of my dick, through the crotch of
    her own girdle, that I was wearing. My dick and balls were in so much
    pain that I thought that I couldn't stand any more.

    Berkie's mom began rubbing my dick in earnest, then stopping
    to squeeze it through the girdle, then rubbing the head, then
    squeezing, then more rubbing and squeezing, until I felt a strange
    upwelling deep inside my guts. The feeling became more and more
    intense until my dick started pumping and jerking on its own. The end
    of my dick felt like it was on fire. Within seconds I had begun to
    spurt out a big wad of cum. Berkie's mom kept rubbing and stroking it,
    and all the while I was coming and coming. This went on for about a
    half of a minute until I was all pumped out. I was exhausted.

    Berkie's mom looked at me with a twinkle in her eye and said,
    "That was fun. You are quite the stud in your bra and girdle."

    She gave me a long wet kiss and said, "let's get that girdle
    off you and clean you up. Just lay there, and let me do everything.
    She reached down on my hips and pulled the top of the girdle down,
    over and off of the end of my dick. I was still hard, but my dick felt
    good to be out of the confinement of the girdle. Berkie's mom stopped
    for a minute and leaned over to kiss my dick, except she didn't kiss
    it. She licked at it. She kept licking all up and down the length of
    my dick and on my belly. Finally, she licked the inside of the girdle
    , that was now outside. She was licking up my wad!

    After a moment, she came back up to me and looking me in the
    eyes, began to kiss me again. Once again she pushed her tongue into my
    mouth, but unlike last time, something warm and runny came in with
    her. She had spit my wad into my mouth. I struggled to get up but she
    was on top, and I was too exhausted to fight her.

    "Hey! Hey! Hey!" she said. "This is what you taste like. It
    isn't that bad. Women have to taste it. You should learn what it is
    like."

    "Well, I just don't want to be a homo," I said.

    Berkie's mom just laughed out loud. "Don't worry, tasting your
    own sperm wont make you a homo."

    It must have been funny, because she chuckled about that for
    the next few minutes. After the initial shock, I had to admit to
    myself that it didn't taste that bad.

    Apparently, Berkie's mom wasn't through with me yet. She took
    my semi-hard dick and pushed it through the crotch of the girdle and
    pulled it back up on me. She then leaned over and began sucking my
    dick until it was again as rigid as before. I wasn't sure what she had
    in mind, however when she lay down on her back I had a good idea.

    "I need you to fuck me now, Bobby. Fuck me while wearing my
    girdle and bra."

    This was not my best friend's mom. This was some sort of sex
    maniac that had taken over her body, I was certain.

    I moved across the top of the bed and began to kiss her.

    "Kiss me down there!" She commanded. "Make me wet again!"

    I kneeled down and began to tongue her pussy like before. She
    arched her back and shoved her pussy into my mouth and said, Stick
    your tongue in! All the way!. Come on Bobby, Lick me!" She sounded
    angry. I tried to do what she wanted, abut she was becoming more
    impatient. Pretty soon she grabbed my head again and started grinding
    my mouth and nose into her pussy.

    After a few minutes she seemed to relax and started moving her
    hips around slowly and making little mewing sounds. She grabbed my
    hands and began massaging her breasts. Soon she grabbed my head and
    dragged me up to her breasts.

    "Suck!" She hissed. I sucked. I wasn't sure what I was doing,
    but she seemed to enjoy it. While I was sucking on her nipples, her
    had reached down to my dick. She took it and guided it towards her
    moist pussy.

    "Bobby, you had better fuck me now! She said. She seemed to be
    getting mad again. I wasn't sure what to do. I started wiggling my
    butt around like the boys at school had talked about. Berkie's mom
    shouted: "Oh for Christ's sakes PUSH! I pushed and popped into the
    warmest place that I had ever known. I was fucking Berkie's mom.

    "Move your cock in and out of me Bobby," Berkie's mom said
    softly. She began to nuzzle me on my neck and shoulder. I was really
    confused about the changes in mood with this woman. One minute sweet
    and gentle, the next minute a real bitch. She was not at all like the
    Berkie's mom that I knew. After a few minutes, we established a rhythm
    and moved our hips in unison working my dick in and out. She became
    wetter and wetter as be fucked. Her belly was wet, her butt was wet,
    the bedspread was wet.

    On my own, I leaned down and began suckling her nipples like
    before. This seemed to please her and she began mewing again and
    moving her hips more erratically. Suddenly she began to stiffen up and
    it became hard to stay on top of her. She bucked her hips up against
    mine. Pretty soon she began huffing and moaning and swearing. She said
    'fuck' about twenty times. I just kept on pumping her as best I could,
    until she just stopped. I stopped and looked at her. She pushed some
    hair away from her eyes and looked back at me.

    "Did you cream? She asked.

    Not sure what she meant, I said "No, did you?"

    Berkie's mom shook her head, muttered "fuck" and grabbed my
    dick. "This is evil. Yes, this dick is evil." She looked up at me and
    said in a calm voice, "yes, I came, you dumb shit. I came."

    "Can we do this some more?" I asked. She spread her legs, and
    sighed "come on Bobby, fuck me some more."

    I lay back on top of her , and we started again. She was
    bucking and I was thrusting, and we were having a gay old time. I
    thought like I was getting the hang of it, although Berkie's mom
    didn't seem like she was getting any wetter. The girdle was soaking
    wet with her juice and was beginning to stink of pussy and burning
    rubber. In fact the whole room was beginning to smell like that.
    Berkie's mom stopped me for a minute and turned over so that her butt
    was pointed into the air. "try fucking me from behind, she said. You
    can go in deeper" I slid inside her and began working her again. She
    took one of my hands and reached around so that I could rub the little
    bump in the front of her pussy. She liked that, and began to bump
    backwards against my belly.

    I was no closer to coming after ten minutes of screwing her
    from behind, when the telephone rang. We tried to ignore it, but it
    kept ringing, until Berkie's mom finally got up to answer it. She left
    the room, and was gone for a while. I could hear her talking for a
    while, and then she was quiet, and then I heard her talking some more.
    After about ten minutes, she came back into the room.

    "Berkie and his dad are staying at Turley for the next two
    days to visit my brother and his wife. They are going deer hunting
    tomorrow."

    "Oh, well I had better go then, I guess."

    "No, please stay. I could use the company, and I could call
    your house and tell your brother not to worry about you."

    "Well, I guess I could stay."

    "Do you want to take a shower? Berkie's mom asked.

    I nodded. I really wanted to get that girdle off and get
    cleaned up. My dick wasn't hard anymore but my balls ached in a
    different way than before, this was a good ache. She led me by the
    hand to the bathroom and started the shower. She took of the bra and
    girdle that I was wearing and dropped the to where the other girdle
    was laying on the floor. We quickly showered and dried ourselves off
    with no more loveplay. We got dressed in our regular clothes and went
    out to feed and water the stock.

    She prepared some sandwiches and we ate without speaking. The
    quiet was so uncharacteristic of the normal way that we related to
    each other.

    "Did you enjoy yourself today, Bobby?" she asked finally.

    "Well, yeah." I replied.

    "Why are you so quiet then?"

    "I am just not sure what to say or do right now, Mrs. C" I
    whined.

    She stood up and came around the table and gave me a maternal
    hug, holding my head to her breast. "First of all, you don't need to
    call me Mrs. C when we are alone. Please call me Alice. And second, I
    want you to know that today was very special to me, and I want us to
    still be friends. O.K. Bobby?"

    I nodded. I felt better. I also couldn't stop thinking about
    what went on that afternoon.

    "I need to do some cleaning up around here, so why don't you
    go back into the bedroom and lie down for a while. Turn the radio on
    and listen to some music. I'll be back in a little bit." She took my
    hand and led me fro the table and pushed me gently toward the bedroom.

    I took my pants off and lay on the bed. I fumbled for a while
    with the clock radio until I found a rock and roll station and
    listened to music for a while.

    They were playing something by the Beatles that I hadn't heard
    before. It was something about doing it in the road. I thought about
    the events of this afternoon and my dick became hard again. My mind
    drifted to thoughts of Alice's underwear and how it had felt on my
    body. It had been very pleasant to try those things on and I knew that
    I wanted to do it again.

    Without much further thought, I got up from the bed and opened
    one of Alice's drawers. There were all sorts of panties, girdles,
    brassieres, and something that looked like a girdle and bra in one
    piece, sort of like a bathing suit.

    This one had lace all over it and a shiny panel in the front
    like the girdle I had tried on earlier.

    Just looking at the wonderful garment made my breathing become
    heavier and I became more aroused. I decided to put it on to see if it
    felt as good as the girdle had earlier. I stepped into the leg
    openings and worked it up to my knees. I had it all bunched up
    together and tried to slip it on little by little. Things were going
    pretty good until I got the thing over my hips and tried to get the
    straps over my shoulders. Things were a little tight and I nearly
    ripped the strap in my failed attempt. Alice was shorter than me by a
    good three inches, so I guess that it stood to reason that this thing
    might not fit. After some fumbling, I got the straps so that they were
    let out a little and I was able to get them over my shoulder at last.

    The bra and girdle combination felt wonderful! It hugged my
    body all over, and gave me a very warm feeling, especially on my butt.
    I felt myself all over and noticed that instead of a split in the
    bottom like the other girdle, this one had snaps and a piece that came
    out. It was made of flimsy material and I could feel my balls through
    the fabric. I rubbed myself and became increasingly excited. I stopped
    rubbing myself so that I wouldn't come right away. I decided to put on
    some stockings, and found a pair of black nylons in the upper drawer
    with Alice's panties. After some fumbling I pulled the stockings up my
    legs and fastened them to the garters that were under the leg band. I
    felt divine in Alice's underwear and stockings. I lay back on the bed
    and felt myself all over again and again for several minutes. I must
    have been more engrossed in my self exploration because I was not
    aware that Alice had been watching me.

    "You look like you are enjoying yourself," she said.

    "I am. I think that this underwear feels so wonderful. Women
    are so lucky to be able to wear these things." I sighed.

    "You might not think so after several hours in that thing."
    She smirked. "Still, you might say that for our immediate purposes,
    it suits you completely."

    I ignored her comment, preferring instead to roll around on
    her bed, relishing the feel of her underwear.

    "Would you like to try a slip on over that?" Alice asked, "I
    have a lovely full slip here that would go well with your outfit." She
    pulled the garment from the panty drawer and held it over my head. I
    slid down over my shoulders and body like the softest glove. I was
    amazed at the overall feeling that all of these clothes imparted on
    me. Ironically, I was not aroused, but rather, content.

    I heard the front door of the house open and close, and a
    woman's voice called out, "Alice, are you there?"

    I panicked. I looked around frantically for my clothes, and
    made for the bathroom door.

    Alice stopped me by moving between me and the door. "Hold on,
    she is a friend that I called a while ago. She will be O.K. with you.
    Why not just relax and enjoy yourself with us."

    "Alice, are you decent? Oh my, what's this?"

    Alice introduced me to her friend, "Lois, this is Bobby, Bobby
    this is Lois. Bobby is Berkie's playmate and has been helping me
    around here today while Berkie is away with his dad in Turley."

    "Does Bobby play with Berkie like this?" Lois asked
    sarcastically.

    "Come on Lo'," Alice responded, "I called you over here
    because this is special for Bobby, and I thought that you might want
    to have some fun with us here tonight. Don't spoil it."

    "Listen, Alice, your judgment in men leaves a little to be
    desired. That asshole that you are married to is enough evidence in
    that area. You should never have married him as young as you were and
    you shouldn't stay with him now, knowing what you do. And what about
    this one, what makes him so special, that you want to include him in
    with us?"

    "He's so sweet, Lo', and besides, he wants to know about women
    and our world. He's a clean slate."

    Lois softened considerably at the entreaties of her friend.
    She walked over to me and ran her hand over my shoulder, down my
    chest, and along my butt. "Are you sweet?" she asked, "You certainly
    look cute. What a lively slip. What's on underneath? Why and all-in-
    one. How nice and controlling. Tell me, can you be sweet for me?"

    I was dumbfounded by this new turn of events, but I managed to
    croak out, "Whatever you want, Ma'am."

    Lois kissed me on the mouth. It wasn't as passionate as
    Alice's, but it did get my dick's attention. Almost immediately after
    she broke our kiss, she knelt down in front of me and said, "Well,
    let's see what you've got."

    Lois pulled my slip up and exposed my girdled torso. "This
    won't do at all, she muttered, and pulled off the crotch and quickly
    pulled my hardening dick down through the opening. "There," She said,
    "That's better."

    Lois immediately put my dick in her mouth and began to work it
    until it was fully erect. She sighed and rubbed my legs and crotch for
    a few moments, and promptly stood up again. In the meantime, Alice and
    left and had poured some drinks, and brought them into the bedroom.
    She offered one to Lois, who took it and set it down on the bedroom
    dresser. She took the other drinks and she embraced Alice in a way
    that confirmed that these two were more that friends. Lois kissed
    Alice full on the lips, and they were locked in that embrace for a
    considerable time. Alice had moved her hands into Lois' coat, which
    had not been removed, and seemed to be caressing Lois' breast. After a
    moment, they released each other, and Lois removed her coat and draped
    it over a chair. She picked up two of the drinks and offered me one,
    and offered the other one to Alice. She took the last. We drank
    without speaking.

    Finally Lois turned to me and said, "Bobby, I want you to
    undress me. Please take off my blouse now."

    I came around the bed to where she stood, and started to
    remove her blouse. It was a slick loose fitting material with a
    flowered pattern on it. I had to stand behind her to undo the buttons.
    When I was done, I lowered it from her shoulders, and handed the
    blouse to her. "Fine," she said, "you may now remove my skirt."

    I looked around for a button or something, and finally found a
    zipper on the side. I undid that and her skirt dropped to the floor.
    She stepped out of it and I picked it up and handed it to her. "Very
    good," she said. "Now take off my chemise."

    Lois wore a two piece layered slip that was beige colored and
    covered in lace. I assumed that she wanted me to take off the top, so
    I lifted that over her head. I then lowered the slip over her hips. I
    had not noticed until then, that Lois had very large breasts that were
    very well controlled by the heavy duty long brassiere that she wore.
    Lois also wore a high waisted panty girdle that had shiny satin on the
    front sides and back. The girdle molded Lois' ample butt into a solid
    and unyielding contour of a very voluptuous, but formal appearing
    woman. I had not noticed, but Alice had removed her clothing down to
    her bra and girdle and was pulling down the bedspread in preparation
    for what was to follow. After turning down the bed, Alice came around
    the bed to me, and gently removed my slip by pulling it up and over my
    head.

    We were all three standing, in bras and girdles, me with my
    dick hanging down through the crotch of mine. Alice motioned to me
    toward Lois, and I followed her lead by guiding Lois onto the bed.
    Alice lay beside Lois and the two resumed their passionate kissing and
    fondling. Each began stroking the other's breast through the fabric of
    their brassieres. Alice took my hand and guided it towards Lois'
    crotch. I got the general idea and knelt down to begin my attention to
    Lois.

    I spread her knees apart and began running my hands up and
    down her nylon encased legs from the knee to the crotch. The smooth
    feel of the girdle leg was exciting to me. I fondled her inner thighs
    and ran my fingers along the crotch of Lois' girdle. I found the
    opening of the split crotch, and gently moved the flap aside. Her
    pussy was beginning to become wet with anticipation.

    I moved my finger along her slit and found her knob near the
    front of her gash Lois gasped when I touched it. Alice said, "Kiss it,
    darling. Make Lois come. Use your tongue." I moved my face near her
    pussy and stuck my tongue on the knob. Lois jerked away and then moved
    back toward my face. I gently licked the area around her knob and she
    began to ooze a slippery substance from her pussy. I licked at the
    ooze and licked around the lips and the knob. Los seemed to like all
    of this as she began moving more vigorously against my face. Alice in
    the meantime had pulled off her girdle and began to straddle Lois'
    face so that her crotch was near Lois' face. Lois began vigorously
    working her mouth and tongue on Alice's pussy. Within moments, both
    Alice and Lois were panting and bucking in the throes of orgasm.

    By this time my dick was no longer loosely hanging down
    through the crotch of my girdle, but was standing straight up and was
    straining against the front of the crotch opening. This hurt somewhat
    since the opening felt like it was cutting into my dick. It wasn't
    turning blue or anything, so I didn't make an effort to get out of my
    girdle just then. Alice then began to fondle it, which made me feel a
    little better. She ran her fingers along the shaft and wrapped her
    hand around the head, and gently applied a little friction. Lois,
    recovering from her orgasm, raised herself up and gave me a deep and
    sensual kiss. Apparently I was sweet enough for her.

    "Alice dear, I want to taste this darling boy again," Lois
    said. "Be a love and move over so I can suck his love muscle." Alice
    moved her hand and moved around to the head of the bed. Lois situated
    herself so that she could suck my dick and promptly took the entire
    thing into her mouth. Lois was definitely a good cock sucker. She
    bobbed her head and sucked on the head of my dick like a jack hammer.
    Then she would go slow and just flick her tongue over the head and
    along the shaft for a while. Finally, she began pumping my shaft with
    her hand, and sucking hard on the end of my dick, brought me to an
    intense orgasm.

    She pumped and sucked on my dick for about a minute, until I
    was completely spent. She lifted her head, and moved toward my face as
    if to kiss me.

    "Swallow," I said. "Alice tried that already."
    groups.wall 125 days ago
  • i used to work at a hotel, so i would go into rooms that had girls staying in them and would always look through there panties and bras and sometimes take a pair of the panties. I was extremely lucky not to get caught but it was such a rush i had a huge collection of other womens panties. I love other women's panties the best, knowing that there pussy was inside them is such a turn on.
    groups.wall 211 days ago
  • Like others, I started wearing my mom's and when my sister got old enough her panties and bikini's, but there is no good stories there. So instead, I'll tell the story of how I aquired my first couple pair of panties. I was in college and living in an off-campus apartment at the time. It was really late and I realized I needed to do laundry. So I took my clothes to the onsite laundry facility. When I got there, it was empty and I started throwing my clothes in the washer. As I was leaving, I saw in the drier that there was a done load and I saw 2 pink panties just sitting there. I immediately got turned on, but I wasn't brave enough to take them right then. When I got back, I made the decision that if they were still there I would take them. I know its wrong to steal, but I just couldn't help it. Anyways, after the aproximately 40 mins or so, I went back and of course they were still there. I quickly put my clothes in the drier, and as I was leaving, quickly opened up the dryer, reached in and grabbed them. I put them in my pocket and left as soon as I could. Being the closeted sissy that I was, I immediately got naked and put on the first pair. It was a pink one that said princess on the back. I was in heaven and immediately rubbed myself through the panties and came all over the inside of them. Before I knew it, it was time to go back to pick up my clothes. I left my panties on, and put a pair of shorts on as well. I was nervous, but also had in mind a fantasy I had where the girl knew I took her panties and punished me for it. Luckily (or unluckily) the clothes were still there, so I put my clothes in my hamper and trudged back to my apartment. That was the beginning of my panty collection. I did get rid of all my clothes after an ex gf found out about a year and a half ago, but I am starting once again to slowly build up.
    groups.wall 228 days ago
  • When I was 16 I had been wearing my step sisters panties for 2 years and she knew I wore them and didn't mind. One saturday she asked me if I would model her panties while my mom and her dad were gone. I told her I would if I could were a bra also and she had to strip down her just her bra and panties. After she stripped down I went into the bathroom put on one of her bras and walked back into my room in just her bra and panties. I walked around and spun a few times for her, her said I looked great in women's underwear. She then asked me to walk a little closer and when I did she reached out and rubbed her hand across my cock, she then stood up and started to rub my ass in her panties. Before I knew it while rubbing my ass she had inserted a finger deep inside my butt. At this point I couldn't take it and started to jerk off and she asked me if I wanted to jerk off in front of her or if I wanted to fuck her, naturally I said I wanted to fuck her so she laid down pulled her panties to the side and told me to put my cock in her pussy. I was so excited the minute my cock was all the way inside her I came (without a condom) but being so excited although I came I didn't get soft and fucked her until she had 2 orgasms and I came inside her a second time. Looking back at it I was damn lucky she didn't get pregnant but god it was such a hot fuck. We had done that several times after that before she graduated school and moved out.
    groups.wall 240 days ago
Collect Crossdressing Stories
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I wish I could have an evening with my wife like this one. Very erotic
Last replied by Bicrossdresser on Tuesday, 10 January 2012
This is such a hot story, I wish I would have had a sister to use her panties like this
Last replied by Bicrossdresser on Monday, 14 November 2011

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