Sissy Outed Brandon to Brandy
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A Sissy And Four Brothers free porn video
A sissy and four brothers -What is it like? Mother is very strict about
separating me from 'the boys' but they've never experienced a 'sister' in
the house before so there seems to be a lot of snooping around. A few of
my readers have asked me for some additional information about farm life
and living as a sissy with four brothers, and I'll respond to the
question about seeing Jack again. Jack's mother called me and told me
that I'd done wonders about boosting his self-esteem and she asked if I
wouldn't mind going out with him again. Of course I said 'yes' because
Jack was a perfect gentleman.
When I was just 'one of the boys,' I slept in the upper bunk of my
brother 'I." I've decided to make life a little easier, I'd just name my
brothers 'F,' 'G,' 'H,' 'I,' and then there is me. 'J' for Jamie. Father
built our farm with his brothers and his father, so the land has been in
our family for many years. It's divided up into smaller family farms and
most of Father's brothers live in the area. They are all understanding
about the 'Jamie' situation because they all have daughters. My mother
and father were the only ones without a daughter. It's kind of not talked
about, like I'm the oddball at all the dinners and visits and stuff like
that. I am not usually the topic of conversation when I'm in a room.
So, any who how, when I was one of the boys, I slept in the same room
with 'I.' I was in the upper bunk because I'm smaller. There is another
bedroom with a bunk bed and a single bed. When Mother requested that I be
allowed to help her and I started becoming a little (okay, a lot) more
girly, I was moved into my own room (Mother's sewing and craft room.) F
and G, hell, I'm just going to call them Frank and Gill, Hank and Ignus
(but we just call him Gus for short.) So Frank and Gill live in one room
and Hank and Gus in the other. I'm closer to Mother and Father's room,
and I have my own separate bathroom. The boys have a bathroom between
them. * I know that I changed my brothers' names - to protect the
innocent. In the other story I told you my brother's name was Dave. But
this time I'm using letters of the alphabet (did you notice that?)
So that's the living arrangements. We got rid of the bunk beds because
the boys are really too big for them now. We're all a year apart. Frank
being the oldest, then Gill, than Hank, Gus, and I was born last. I
mentioned that because I got picked by Mother to help her with the
'women's work' because I'm the youngest and the smallest. Not only
because I'm the youngest, but I'm just not as big as my brothers. Not
petite, mind you. Just the runt of the litter, I'd say. That's farm talk
for you city folk. I'm not as hairy as they are anyway, and the hair on
my head seems to grow faster than theirs, so Mother and I have agreed to
let it grow. She has some weird desire of brushing my hair a lot, and
since I'm closer to her room now, she comes by and visits me in my room
and I let her brush my hair.
So, like I said, Jack's mother called and asked that I consider going on
another date with him. I mentioned in a previous story that he and I went
skating together. I wore my purple leotard dress, with white tights and
cute socks. I let him put my white ice skates on me. I thought that was
kind of sexy. I'm not sure why girls like that, but for him to be lacing
my skates for me, I felt a little helpless and he was like my knight in
shining armor, coming to my rescue. I know, it sounds silly, but hey, it
felt that way. The reason I mention this, and why I want to talk about my
brothers and boys in general, is that they have some peculiar fascination
about seeing what we're wearing under our skirts.
Like I said, Mother and I have been doing the laundry around the house,
you know. Cleaning up my brother's rooms and washing their clothes and
all. It's not a big deal, as you'd expect their clothes to get really
dirty, working on a farm. And I don't mind helping Mother in getting,
washing, drying, and putting away their clothes. It was mine and Mother's
things that started my fascination about my brothers looking at our
things hanging on the line. Now that Mother had another 'girl' around,
we'd started washing our intimates together. You know, delicates and
dresses and that kind of stuff. Well, one time, I was hanging our panties
and bras, some pinafores and dresses on the line. I didn't think much of
it, but when the boys came in for lunch that day, I noticed them all
staring at the clothes line. I didn't do it on purpose, but I'd hung our
panties in a way that was easier for them to see.
Mother told me next time to put the undies on the inside and the dresses
on the outside, so they wouldn't see our intimates. Opps! Didn't think of
that one, but what is it about a boy's fascination with seeing our
panties? Then I got to thinking about Jack. I did pull my skirt up a bit
when he was tying my skates, but even if I'd pulled my skirt all the way
up, all he'd see would be the leotard. It's not like boys haven't seen a
girl in ballet clothes, I thought. Then I remembered that Jack didn't
have a sister, so maybe he'd never really seen a girl in her dainties. I
wondered if he was all weird about seeing what I was wearing under my
leotard dress. I got to thinking about this a little more than usual. As
a boy, was I really that curious about what girls wear under their
dresses and skirts? How would a boy find out about that kind of stuff?
We'll duh, it really was easy. Just show them the advertisements in a
weekend paper, or maybe a Victoria's Secret catalog, or something like
that. In the old days, they used to have the JC Penney catalog. I
remember looking through that and flipping fast through the women's
intimates or young girls' bras and panties section. But a boy now might
not have the opportunity to see these intimates for sale. Of course, now
they have the internet, but that seems perverted in a way. Like the boy
would be abnormal for looking at girls either naked or partially dressed.
It just seems like pornographic material to me (as a boy!)
But as a girl, I don't look at the girl. I look at how high the brief
goes up on her belly. Or whether I like a color or a style. I think that
a 'boy cut' panty is ridiculous. Boys don't wear panties so don't even
describe a panty as a boy cut. I now understand bra comfort and I look at
bras totally different. As a boy, I'd think they didn't care about the
bra at all, but just want the girl out of it so they can suck on the
breast or something like that. But as a girl, I imagine what dress I'd
wear and coordinate my panties, and maybe think about Jack seeing me in
these intimates and wonder if he'd get all hard. Then I start getting in
the mood as well. Now a regular girl would start getting a little damp
down there, with her vagina starting to become moist as she thought of
sexual arousal. Maybe dancing seductively in front of her 'guy' and then
she'd remove her panties and her bra and they'd make love like a normal
couple.
My panties get damp for a different reason. I think about the girls in
their undies and me in my girl undies and we have lesbian sex. I lick on
them until they come and they give me a blow job, but I'm still in my
panties. I like to wear a bra because girls my age wear bras. We like to
mix and match and wear our intimates so they coordinate with the dress,
or skirt and blouse we're wearing. I know I like it when I see a girl
wearing a pink bra (you can tell by the bra strap) and a pink cami tee-
shirt with the cute lace around her tummy, and then another blouse (pink
or maybe purple) but it all matches. What I hate is when a girl is
wearing a black bra and it's obvious it doesn't coordinate with the top
she's wearing. It seems so slutty. Now that is the difference between me
and my brothers. They wouldn't notice that the black bra didn't
coordinate with the top. All they'd notice is that the girl was wearing a
black bra and they'd think that was sexy and they'd probably wonder if
she were wearing a sexy black thong panty and they'd want to get her out
of that stuff and see her naked. To me, I'd want to take her to her panty
and bra drawers and show her which bra and panty would be better to wear
with the outfit she was wearing. Of course, I'd love to play in the panty
drawer and see what intimates she wore and then maybe we would make love
but it all still has a lot to do with her clothes.
So, I agreed to go out with Jack, but I told his mother that he had to
ask me out this time. I mean, I had to have my brother ask Jack to ask me
out. It was like pulling teeth. This time, Jack's mother told me he
wanted to ask me out but didn't want to be rejected. I told her that I
wouldn't say no, so he should ask me out. Of course Mother got wind of
the plans and started planning on what I'd wear and where he would take
me, and what kind of makeup I'd wear if we were going to a restaurant, or
a different kind if he were taking me miniature golfing. You can see how
complicated it is as a daughter. Mothers don't care about that kind of
stuff for a son.
She took me to my room and we started looking through my closet to see
what I had in the way of dresses. Anywhere we were going, I was going to
go in a dress. Mother decided that one for us.
"Time to go 'date' dress shopping," she proclaimed. Apparently, 'date'
dress shopping is different than regular dress shopping. "Of course," she
said. "He's going to be undressing you with his eyes all night long, so
you'll want to wear something that he'll want to take off you."
Okay - So Jack called and invited me out to dinner, at a nice restaurant
a few miles from the town we live near. It's a pretty fancy restaurant.
Not like some cheap diner or anything like that. This one you have to use
real cloth napkins. Mother informed me it was time for that little black
dress or LBD for short. And black lingerie is like 'totally' appropriate.
This is one time she informed me, that I'd want him to see I was actually
wearing a black bra.
"Mother!" I couldn't believe it. She and I were going to go shopping for
a black dress and black lingerie. I don't know if you've ever heard that
a girl who wears black lingerie 'wants to get fucked!' and I'm sure
Mother has heard that before because she said that, without the
profanity, mind you. We went to one of those specialty women's boutiques
and Mother made it plain to the salesgirl that I was there for a special
date dress with 'all the fixin's' as she described it. That meant a
strapless long-line bra, black panty-girdle, garter belt and stockings.
Really sexy ones, and of course, a black off-the-shoulders dress. "This
is a special occasion bra," the salesgirl informed me. Mother selected a
dress with a low-cut back so the bra had to be low-cut and the girdle
couldn't go too high up my tummy. The salesgirl informed me that a corset
was definitely out of the picture, and that was too bad because she said
I could use the shaper to give me a curvier figure. Like duh? I'm not a
real girl, so I don't have that curvy figure some of the girls in my
school have. I must admit that wearing a garter and stockings instead of
tights really was kind of sexy. I mean, I felt more like a woman than I'd
ever felt before when I went into the dressing room and tried on all that
stuff. Mother was in there with me, so the salesgirl let us be.
Mother made it clear after I had all the things on that Jack would
definitely want to get into my panties. A little too much information, I
informed her, but looking in the mirror, I think I had to agree. The cost
came out to over a hundred dollars, but Mother said I was worth every
penny. Of course, I would have to show Father so we planned on my giving
him a little fashion show around dinner time. Of course my brothers would
be there.
Remember I said that my brothers were kind of staring at my undies when
I'd hung them on the clothes line? Well, you can imagine how I knew
they'd react when their brother came into the dining room wearing an LBD.
And I was right. Everyone's mouth dropped when I came out at dinner
dressed in that dress. It was weird thinking all my brothers were looking
at me like I was a sex object instead of their brother. I hoped I wasn't
causing much discomfort, but I decided that I'd eat dinner wearing that
dress when I wore it in front of Father. Mother was absolutely beaming,
she was so proud. She'd helped me with my makeup before Father and the
boys got home, so I must admit I looked pretty hot!
Well, Jack did take me out to dinner, that Friday as a matter of fact. He
drove the family sedan instead of a pickup, which was nice because I
didn't want to be wearing that black dress and trying to jump up into a
pickup. Girls have it tough in some situations, I can tell you. Jack
picked me up right on time. My brothers were all standing around watching
when I left arm in arm with Jack. They watched as he opened the car door
for me. They watched as I slid in (properly, as Mother and I had
practiced.) A girl has to be careful about sliding into an automobile,
lest she show her delicates. And I knew my brothers were watching!
(Sickos) trying to look up their sister's dress to see her panties. I
slid over a bit and sat close to Jack. I know I was getting him in the
mood. I mean, there was like an actual tent in his pants. I couldn't
control myself. I knew I was doing that to him, so as he drove, I
unzipped him and out popped his cock. For a guy who everyone thinks is
gay, his privates where definitely at attention, and for whatever reason,
I really wanted to see my lipstick print on the head of that one-eyed
giant. I started kissing it and licking while he was driving. My panties
were definitely getting wet. I came in my panties without even touching
myself.
I hadn't had him in my mouth for more than a few minutes and he spurted
his cream like all over the place. I mean, I was on it, and loving every
second. I didn't know any guy could have that much semen backed up like
he did. I did my best to swallow as much as possible, and I used a hanky,
(I'm glad Mother had me carrying one) to clean up as well. My lipstick
looked so sexy on the head of his penis.
We had to pull over for a few minutes so Jack could catch his breath.
Fortunately, nothing got on my dress, or his slacks. Wow, for someone who
claims not to be homosexual, I'm not doing a very good job of proving it,
am I? I had to use the vanity mirror to readjust my lipstick and I asked
Jack to let me out of the car for a moment to make sure I didn't get
anything on my dress. We eventually made it to the restaurant and had a
wonderful meal. That was like my second, if you know what I mean. Jack
surprised me after dinner. He said he'd planned on taking me to the movie
theatre but after that little sexual escapade, maybe I'd like to go to a
motel room, instead.
He said that since I'd satisfied him so well, maybe I'd like an
opportunity to enjoy some sex as well. We kind of laughed about it for a
while as we really are kind of young but I agreed that I would like for
him to see what I was wearing under my dress. So we agreed that we'd go
rent a motel room for a while. A couple of hours at least. He came so
fast in the car, I was wondering if we'd need a couple of hours. He paid
for the meal and drove us to a nicer motel. It wasn't all sleazy if you
know what I mean.
So here we go; my first sexual experience as a sissy, in a hotel room,
with Jack, whom many think is a homosexual. I mean, he's here in a motel
room with me. But I do look really pretty damn sexy, let me tell you. I
let him unzip my dress. I walked over to the hangers in the closet and
pulled one out. I hung my dress, again looking for anything like dried
semen or maybe a food stain or something. My dress was clean. So I was
standing in front of Jack wearing my shoes, stockings and garter belt, a
black panty-girdle, and a long-line strapless bra. The dress had a liner
so I didn't need to wear a slip, though I felt kind of naked without one
at this moment. I was thinking that the first time, I'd be wearing a
nighty or something while with a guy. This was like real woman stuff
happening now.
I walked over to him seductively and helped him pull off his tie and
started unbuttoning his shirt. He allowed me to do that as he unhooked
his belt and unzipped his pants. I tried to tell him to slow down, but I
don't think he could. If he was gay, he was doing a pretty good job in
hiding it. When his cock popped out and he removed his underwear, I asked
him to rub it up against my pantied- ass. I wanted to feel it rubbing
against the softness of the material of the panty. I removed the garter
belt and sat on the bed to remove the stockings and my shoes. He pulled
the blanket and sheets down and I slid up to the pillows, now wearing
just the girdle and the long-line bra. God, I felt so sexy. He was
completely naked, with his penis sticking out like a... I don't know what
it was like, just sticking out. Pretty damn big, that baby. Looking like
it'd hurt wherever he was going to put it.
I took off my panties. I lied on the bed with my back facing him. "Be
gentle," was all I said, lying down facing away from him. I let him
explore my body, even my penis which was sticking out as well, but half
as big as what he had between his legs. Now it sounds like it's getting
all gay and everything, and I don't want to make it sound that way. He
touched me like he would a woman. And I allowed him that. I pleased him,
and he pleased me. He didn't take me in his mouth, but he rubbed his
penis against my bum. I kissed it and moistened it so it wouldn't hurt so
much going in, then he penetrated me, like I was now his woman and wanted
him to fill me with his manhood. Which he did wonderfully. I felt
fulfilled. A woman in a man's arms, being filled and complete. Now I
understood why women like this so much. There is much satisfaction having
a body void filled and complete. He came inside me, and I'm so glad I had
the appropriate woman's gear in my purse. A heavy pad to protect my
pretty undies. We'd made love for about an hour, I took a shower and
cleaned myself as best I could. I definitely redid my makeup. I couldn't
have Jack drop me off after a date and me looking like I had sex would
not have gone over well with my father. I'm sure my brothers wouldn't let
me live it down either. Jack and I agreed that we'd had dinner and gone
to a movie, even though both of us had our first sexual encounter
instead.
Mother came into my room while I was undressing, and she noticed I was
wearing a maxi-pad. She didn't say anything but I don't think I hid it
very well that we really didn't go to a movie. She asked, and I couldn't
answer her questions very well about what movie we'd seen and all that. I
wasn't going to respond to her questions about our having sex, and I
think she knew that. She helped me get undressed and pulled out a nighty
for me. She asked if I thought Jack might like to see me wearing
something like the nightgown she'd selected and we both giggled a bit.
"Yes, I'm sure he would!" I responded.
I walked a little different the next day, like because my bum was a
little sore. I had to use a tampon and a maxi for the day, and I put some
lotion on my behind to help with the pain. I think Mother noticed I was
walking like I was a little sore. But then, again, she didn't say
anything.
I hope this answers the questions people have asked about sex with Jack
and what it's like living with a bunch of brothers. I hide my undies a
little more, because I think it's gross that they'd want to see them.
It's not like I walk around in my bra and panties. My brothers all still
walk around in their underwear around me and my mother and father. It's
like they don't care about that kind of stuff. I happen to like having
some special occasion undies for dates and stuff like that. Every girl
needs an LBD for weddings and special occasions.
Will Jack and I become a couple? No, I don't think so, though I'm glad he
was my first sexual experience. I told my girlfriends at school
everything. I want them to know that we, Jack and I both, are sexual
beings. I want them to know that Jack is really probably not gay, though
I can't say for sure. I mean, he's kind of gay, like he's afraid of girls
and all that, but once you get him out of his shell, he's really an okay
kind of guy. Just not the jockey masculine type. My friends all wanted to
know more about the dress and lingerie, and about our little romp at the
motel. Like I said, I told them everything, and I feel more like a young
woman because of it. I did things that a woman would do. I think I moved
up a few notches in their opinion of me, that I really am as much like
them as I can possibly be. I certainly hope they don't think of me as a
slut or anything like that. I tried to be as much a lady as possible,
though with feminine desires of wanting to be filled with a man.
I'll let you know if Jack and I go out again. I mean, if you interested.
I hope I didn't give too much information here. Just want my readers to
know who have been following along what it's like to be 'Jamie.'
I'm going to bed, my bum still a little sore, but knowing what it's like
to be sexually fulfilled as a young woman, wearing a nice warm flannel
nightgown and gray briefs, feeling kind of pretty.
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