From alt.sex.stories.tg Thu Jun 6 00:04:59 1996

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~From: someone@somewhere.com (Someone in Seattle)

~Newsgroups: alt.sex.stories.tg

~Subject: New TG:Sarah

~Date: 2 Jun 1996 21:18:48 GMT

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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...