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I wiped the cum off my face and...

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  • I wiped the cum off my face and...

    My sister Jennifer and I have always been very close. She is
    two years older than me and has known about my crossdressing ever
    since she caught me wearing her clothes when I was eighteen. I'll
    never forget the day she caught me.
    Since we went to the same college we were roommates and I had
    stayed home from school that day specifically so I could get some
    privacy from Jennifer and dress up in her clothes. As soon as I
    was alone, I drew a bath to shave my legs. When I finished shaving I
    went straight to Jennifer's bedroom to put on her makeup. I had
    a lot of practice at this and did a pretty good job. Next I put on
    her blonde wig and press on nails. I then went to rummage through
    her lingerie collection. I chose a black lace bra with matching
    garter belt and panties. I was just attaching the last garter to
    her sheer stockings when Jennifer walked in. I hadn't expected her
    to come home for lunch, and needless to say was pretty embarrassed.
    Well, she wasn't surprised at all and even said she suspected it
    all along. She agreed to not tell our parents and said she would
    even like to help me become as pretty as I could.
    She sat down next to me on the bed and started to ask some
    questions, "John, do you really want to be a girl? Do you really
    want to be with men?" I replied that I'd thought about it, but
    wasn't really sure.
    She continued, "well John, I'm glad we got this out into the
    open. I've always wanted a sister and I know we can have so much
    fun together. I'll help you any way I can, but I think you should
    have a female name." I told her that she can call me Sarah if she
    wants to.
    Jennifer then let me in on a secret of her own. She reached
    under her bed, and took out a box which was hidden up against the
    wall. She reached inside and pulled out a dildo. She said that if
    I was interested, to go ahead and play around with it, and that
    she'd even like to watch some time if I thought it was okay. With
    that she left for school, leaving me there in a stupor wondering
    what would come out of this.
    Sitting there still wearing nothing but a bra, panties, garter
    belt, and stockings, I picked up where I left off and tried on some
    of Jennifer's dresses and modeled in front of the mirror. I settled
    on a blue coatdress with matching pumps. I picked up the dildo,
    which looked and felt like a real penis, and wondered what it would
    be like to have sex with a guy. I went back to the mirror and
    looked at the image as I put the fake penis to my red lips. Then
    I realized that I really did want to be a girl.
    Halloween was coming up and Jennifer was going to be
    having a big party. She suggested that I could be a girl
    and no one would care. I told her I didn't think it would
    be a good idea to dress like that in front of so many
    people, but she allayed my fears and I reluctantly agreed
    to go ahead with it.
    We had about four days to go until the party, and
    Jennifer insisted that I live as a girl until then if I
    wanted her help. Against my better judgement, I went
    along with it. Besides, I could just miss a few days of
    school with not much of a problem.
    Jennifer got to work on me right away and said
    something that kind of frightened me, "When I get done
    with you, you won't even want to go back to being a boy."
    I put on a smock, and she went to work right away.
    She put a relaxing mask over my eyes so I couldn't see
    what was happening. My naturally long hair was styled and
    cut. Several hours went by, and it wasn't uncomfortable
    until she started plucking my eyebrows.
    "Ouch!" I protested. "Not too much."
    "I know it hurts a little," she said, "But just
    think how attractive you'll be when they're gone. Now you
    know what we girls have to go through to look
    attractive."
    She then took me into a room without mirrors to
    apply my makeup and some acrylic nails. After dressing in
    my cheerleader's outfit, Jennifer brought me to a mirror
    so I could see the final product.
    I was in shock. I looked convincingly like a college
    coed with my makeup and new nails. I shook my head and
    curly hair danced around my neck. My delicately arched
    eyebrows gave me a permanently girlish expression to my
    face. Jennifer noticed my stare and said, "Don't worry
    about the eyebrows, later I'll give you some pencils to
    fill them in."
    She said I was going to have to get my own clothes
    if we were really going to pull it off. I switched into
    a regular skirt and blouse and we went to Nordstrom to
    max out her credit card. When we got there we really went
    wild: four pairs of shoes, a number of items of lingerie,
    about twelve pairs of pantyhose and stockings, skirts,
    blouses, and dresses. These clothes fit a lot better than
    Jennifer's did on me and I couldn't help but thinking how
    wild it was that now I owned everything that a typical
    college coed would have in her wardrobe.
    I was relieved to get back home so I could get out
    of my girl clothes for a while, but when I went up to my
    room, they were all gone. I yelled at Jennifer to give
    them back, but she refused and said I agreed to live as
    a girl for a few days anyway so I'm just living up to my
    agreement. I finally gave in, but I told her that I
    hadn't thought it would go this far and I wanted my stuff
    back after the party.
    We argued for a while but then decided to go dancing
    at a popular nightspot in downtown Seattle. I didn't want
    to go at first, I was pretty scared going out to a
    nightclub where surely I would be hit on, but both
    Jennifer and I agreed that I probably wouldn't have a
    problem passing. I decided to wear my new sleeveless
    black lace dress that came to just above my knees, black
    stockings, and three inch heels. With Jennifer's
    guidance, I did an expert job on my makeup.
    When we got to the club, though, I was still a
    little nervous. The place was crowded and dark. It seemed
    like there were three times as many guys as girls.
    Jennifer grabbed my hand and pulled me into the middle of
    it.
    We danced for a while and then were separated. I
    finally found her with her boyfriend Frank. I pulled her
    aside, hoping Frank wouldn't recognize me. I told her I
    think we should go because it was getting late, but she
    told me she was going home with Frank. She told me not to
    worry, "I told Frank that you're my cousin Sarah visiting
    from New York. He doesn't have the slightest clue." She
    told me his friend Mike would give me a ride home.
    I was introduced to Mike and he hung out with me for
    the rest of the evening at the club. He was nice and
    bought me some drinks, but I managed to avoid most of his
    advances. We were sitting back in a dark corner and I
    started to get tired. I asked if he'd drive me home now
    and he said to get my coat and we could go. On the way
    out he put my hand in his, and for some reason I didn't
    even resist.
    When we got back to my place Mike asked if he could
    come inside to use the phone. I let him in and went to
    sit on the couch and turned on the TV while he made his
    phone call. When he was done with his call he sat down
    next to me. Jennifer must have gone to Frank's house
    because she wasn't home yet. I was getting pretty nervous
    that maybe he was attracted to me sexually and would try
    to make a move on me, and my fears were soon realized.
    Mike's arm slipped around my waist and pulled me
    close. A moment later, he started kissing my neck. He
    kissed behind my ear and chewed on my hoop earring. I
    didn't know what to do. Being a guy, I wasn't supposed to
    be doing this with another guy. He caressed my shoulders
    and whispered, "I want you." I lost my breath and he
    pushed me back on the couch and held me down with his
    body. I shut my eyes and his body was rigid pressing
    against mine.
    Suddenly, he moved his lips to mine and forced his
    tongue down my mouth. Confused about my feelings, I
    briefly submitted, but then I felt Mike's hand on my knee
    gently lifting the hem of my dress. "Please, you
    mustn't!" I pushed him away and stood up. "I think you'd
    better leave now."
    Mike apologized, telling me I was just too
    attractive and he lost his head. The thought of his
    intentions sent chills up my spine. What if he had
    discovered my secret? I was relieved when Mike finally
    left, and was mad at Jennifer for putting me in this
    position.

    I awoke the next morning feeling depressed. I was
    supposed to be kissing the girls, not the boys. Since my
    legs were freshly shaved from the night before, I didn't
    bother with nylons, and did some household chores wearing
    a linen skirt with flats. I paid special attention to my
    makeup though, because I wanted to make sure and
    practice.
    Jennifer didn't get home until noon the next day. I
    told her what happened, expecting a little sympathy, but
    instead she actually enouraged me to go out on a date
    with him. She pointed to me sitting there in my skirt
    with dainty and feminine features. "I want you to
    experience all the things girls experience, and that
    includes dating."
    "But I just look like a girl. It's not right," I
    said.
    "Girls like men. If you don't pretend, they'll
    notice something different about you. Maybe they'll
    figure you out. Like last night with Mike, that was a
    natural thing to do. It didn't mean a thing." She then
    gave me a few pointers, "Now about dating men, here are
    the rules. How far should you go? On the first date maybe
    a kiss, and then just a little farther each date to keep
    him interested."
    By now, I was feeling pretty low.
    "If a guy gets to fresh," Jennifer continued, "just
    tell him you're having your period. I'll give you
    something to carry in your purse. You know what that
    means, right?"
    I wanted to be somewhere else, anywhere but here
    listening to this.
    Frank called Jennifer and asked if Jennifer and I
    would be interested in going on a double date with him
    and Mike. Despite my objections, she accepted.
    When she got off the phone, Jennifer got a little
    more stern with me, "John, I mean Sarah, I am getting a
    little tired of your scared antics. When I agreed to help
    you look pretty, it was understood that you do this on my
    terms. You can't just play around at being a girl. I'm
    definitely not going to tolerate living with some sissy
    effeminite boy, you're going to have to be truly
    feminine."
    Well, I was in a bind and had to go along. I guess
    she had a point. If I was feminine instead of effeminate,
    I would have less of a chance of being found out. Even
    though I had a fairly soft shape and fleshy chest,
    Jennifer thought that for our date I should use one of
    her control garments. I said, "Please, Jennifer, this
    just isn't necessary. I'm getting by okay without this
    stuff."
    She became angry with this, "Remember what I told
    you, there will be no argument about it."
    I thought of the feminizing effect this would have
    on me, and became concerned. I'm a man, not a girl.
    Jennifer picked out a long line slimmer bra with garters
    attached to the bottom. It looked to small, but she
    insisted that it would work just fine. I undressed and
    she slipped the garment around my frame. She slowly
    tightened the strings to firmly seat the garment.
    "See, that's not bad is it?" At her direction I then
    put my arms over my head while she tightened the straps
    to my discomfort. She drew several more inches to where
    I became breathless. This forced the flesh up on my chest
    to form promising little breasts and rounded my hips to
    girlish proportions. I caught myself wondering what it
    would be like to have real breasts.
    "You've come a long way young lady. Sarah, I think
    maybe you should be my sister even after the party." She
    continued, "You're a girl all this week, and I expect you
    to act like one. A little kiss or two is not going to
    kill you. If you relax a little, you might even enjoy it.
    Just submit to Mike's wishes and enjoy it. Say it, I am
    a girl. Come on."
    "OK, I am a girl." I gave in.

    Jennifer thought it would be cute if we dressed like
    we were twins for our date that night. We applied
    identical colors of base, eye shadow, mascara and red
    lipstick, the reddest I had ever worn.
    We wore identical red dresses with black belts and
    high heeled pumps. Jennifer smiled at me as we sheer
    black stockings to our black lace garter belts. From the
    matching black panties, bras, to our jewelry, we looked
    identical.
    The boys came to pick us up at about 7:30 that
    night, and we were promptly off to the restaurant. I was
    pretty quiet at first, but the meal was good and after a
    few drinks I started to lighten up. Mike told me all
    about himself, about how he was in medical school and
    wanted to become a doctor. He asked me questions about if
    I had a boyfriend back home, and I told him that I did,
    hoping he would back off.
    Done with dinner, Jennifer suggested that we take a
    walk through the park. It was late at night, and we were
    the only one's there. Jennifer and Frank walked ahead of
    us and Mike slipped his arm around my waist. He tapped
    Frank on the shoulder and said, "You two run along, we'll
    catch up in a little bit." I tried to intervene, but they
    were off and Jennifer just looked back and winked at me.
    Mike took my hand and led me to a secluded area
    where we sat in the grass. Mike leaned over and kissed me
    on the lips. He wrapped his arms around my waist and
    started caressing my thighs under my dress. By the time
    he got to my stocking tops I started to resist, but this
    just made him try harder. Mike then forced my hand on to
    the hard bulge in his pants and said, "Sarah, I want you
    to do to me what Jennifer is doing to Frank." I looked
    over at them and was shocked to see Jennifer's head
    slowly bobbing up and down on Frank's crotch.
    When my glance returned to Mike, our lips met in a
    fiery embrace. For some reason, to this day I really
    don't know, I kept my hand on his penis. He spoke to me
    softly, "Open me, Sarah." I placed my long painted nails
    on his button and zipper. I was clumsy at first, but
    managed to finally open his pants and could see the
    length straining against his underwear. I trembled at the
    thought of what was happening, but rubbed my right thumb
    and forefinger against the rock hard shaft. He gently
    caressed the back of my head then told me what to do,
    "Reach inside, just pull it out and stroke me."
    With both hands I then pulled his shorts off, and it
    popped out, swaying just inches from my face. There was
    a clear liquid at the hole, and I leaned forward, stuck
    my tongue just barely close enough to touch the tip. Mike
    moaned as I then ran my tongue slowly down the entire
    shaft and then up where I pulled back and pursed my lips.
    I let the head slip in, then stopped and looked up into
    his eyes when he grabbed my head and guided me slowly up
    and down on him. I could feel it sliding on my tongue and
    brushing the top of my mouth as I tasted the precum
    mixing with my saliva.
    He moved faster and faster, in and out of my lips,
    and I could tell by his grunts that he was going to cum
    inside my mouth. Mike suddenly tightened up and I felt
    the first spurt hit the back of my mouth. I couldn't keep
    it all in when the second shot burst into me, and by the
    time the third hit, it was coming out, dribbling onto my
    chin.
    I wiped the cum off my face and he held me in a
    tight embrace, "Sarah, you were wonderful, and I want to
    see you again. I'm going to be at Jennifer's party and
    I'm sure we can be together again." I told him maybe, but
    that we better catch up with Jennifer and Frank. We
    finally found them and I knew I was getting in over my
    head. The next few days promised to be nothing, if not
    interesting...


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