I guess it is all about timing. part 1

I have been living with my buddy John for 5 years. I could
not have asked for a better roommate. He has a brother Nick. Well, Nick is
still finding himself. He is 22 and kind of dated girls all his life till about
3 years ago.
Nick knew he was just not that into girls but did it because
well, you know that is what he thought he should do. Deep down he knew
something about him was different. But he also was not sure or had a hard time
thinking that maybe girls are not for him.
In this time of the world, being gay was not that big a deal
but at the same time. It was as we all know.
Now it sounds like I’m trying to say I know everything about
it as if I’m gay. But I’m not. I’m straight but am far from homophobic. I guess
you can say I have always been forgiving and very open minded to people that
are gay. For me no big deal. What ever makes you happy.
For some reason Nick came out to me first. I say came out
but Nick really didn’t know if he was gay. Just had so many things going in his
head that he needed to vent.
My roommate was at his girlfriends for a weekend 3 years ago
and Nick and I were drinking and he just let it all out.
It all started with him telling me he was still a virgin. I
was shocked and as we talked most of it was because of him that he didn’t go
there yet.
We started talking about girls and sex and it came out that
he was not even sure he wanted to have sex with a girl. He started telling me
that there was something about guys he was intrigued about. But at the same
time, he was saying as a boy he could not see himself kissing another guy. 
Him and I talked for God like 10 hours about all of this
that night. It was day light the next day when we realized it.
He thanked me for me lessoning to him about all this and was
so happy to have been able to talk about it all.
He moved away for collage and comes home for the summer
every year. When he comes home he will stay with us.
Collage was a great thing for him as it let him really open
up to himself. Being somewhere where people really didn’t know him. Let him
explore and start to find himself.  
Him and I kept talking as he felt comfortable talking to me
as I was his first to know anything and he know I didn’t care about his
sexuality. I just wanted him to be happy.
Well back to why we are here. John and his girlfriend went
to Cabo for a week.  Nick was back for
the summer.
Let me resay that Nancy was back for the summer. Nick came
to the realization that he was gay. But at the same time still felt odd about
being a boy and wanting to be with boys. So, he took a big step and wanted to
explore transitioning to being a girl. Now Nick/Nancy is still finding himself
and I say, him still as he goes back and forth from being Nick and being Nancy.
I have known him for a long time and I mostly call him Nick as habit but I also
am one of the few that know all and when he is Nancy, I do refer to Nancy as
Nancy.
Nancy started taking hormones about 2-2 ½ years ago. Nancy
didn’t come home last year because of just starting the hormones and dressing.
Nancy was not ready to be fulling out at home yet and very few knew.
I get home and knew Nancy was coming home so was excited to
see her for the first time. Nancy and I talk all the time but I have not seen
Nick/Nancy senses the hormones.
I’m waiting for Nick/Nancy to get there. It was about 11 at
night and still not there yet. I was thinking. Fuck it I’m going to bed and I
see lights drive up. I open the door and it is Nick.
He can see the look on my face as I’m not sure what is
happening. I have known everything about what he has been up to when it comes
to being Nancy. He told me how excited he was to come home and be open about
it. That for the first time he was going to be Nancy at home. He even told me
he had been talking to this guy her for about a year and was going to be going
out on a date with him. Etc etc
But here standing in front of me is Nick. Well Nick with
long hair. He is dressed just like he always use to be. Looking like that guy I
have always known.
He comes in and it is kind of awkward silence. I’m just
looking at him trying to see Nancy in him and the only thing I see is his long
hair and for the first time. He ad 3 bags with him. Normally he would show up
with just a gym bag and that was it. This time he had his gym bag but also 2
big rolling suitcases.
He breaks the air. I know I know this it not what you were
expecting.
I just shook my head agreeing.
Then I say. Look you know me. I’m want you happy. If you
need to be Nick. I’m cool with it. If you want to be Nancy, I’m cool with it.
What ever you need I’m here for you.
We set down and catch up. Have a couple of drinks. It was
getting late and we were both tired and we go to bed.
It was about 20 minute later I hear Nick’s door open and
then close. I didn’t think anything of it. Just thought he hit the bathroom.
I get a text, I need your help.
Sure anything.
I really want to be Nancy this trip. So, I put all my Nick
clothes outside my door. Will you take them and hide then so I have to be
Nancy?
I pause and then say are you sure?
It was a good 10 minute and I get a text back.  Yes, 100% sure. Please help me I need this.
Ok I will help.
The next morning, I get up and the bag is outside the door
still. I’m heading to work so I grab the bag and put it in my trunk and head to
work.
I do not hear from Nick/Nancy all day and it is about 2pm
and I get a text.
What did you do with my clothes? I need to got to the store
I forgot something.
I didn’t know how to answer this. I knew what he wanted. But
at the same time, he begged me to help him and to hide his clothes for the
summer.
So, I text back, hey Nancy, did you rest good?
Yes
Then another text asking for the clothes.
I play it off like I didn’t read that. So, Nancy, are we
going out to dinner tonight or would you like to stay home and me cook?
I do not get a text for some time. I text again. Look Nancy,
you asked for my help and it is time to jump in the deep end. I will be there
to help but I’m also going to push you. I will be home at 5. I will take you to
the store when I get home. You will pick up the couple of things you need and I
will pick us up some stuff for dinner. It will only take us about 30 minutes
out and we will be back home and I will make dinner.
I know Nancy needs this push. I know once the first outing
is under the belt. It will be easier.
I get a text back; Ok I will be ready when you get here.
I get home and walk in and I almost stop in my tracks. Nancy
looks amazing. I have known Nick for years so I can see some of Nick there but
at the same time. There is no doubt this is Nancy now.
I’m looking Nancy over. Nick has always been a little guy,
skinny etc. But standing in front of me is a woman. Hair is on point, not much
makeup but hits all the right things, little sundress with a hint of tan lines
from a bikini top, pulled in at the waste and I swear she has hips, legs are
nice and tan and had on little high heel sandals, painted toes to match her
fingernails.
I look back at Nancy’s eyes. She is looking down and I can
tell shy and nervous.
I walk up to her and lift her face to look at me and I say,
Nice to meet you, Nancy. I give her a hug and ask. Are you ready to head to the
store?
I hear Nancy take a breath and shake her head yes.
We head to the store and that breaks the ice for her.
We spend the week getting to know Nancy. Nancy is really
opening up and be her. Going places etc. We just click and we are like this is
nothing new to us. She is being 100% Nancy. It is like we have been living
together like this for years. I have seen it all from her. From all dolled up,
to messy bun, tanning in a bikini by the pool, silk PJ’s, little baby doll, to
getting out of the shower rapped in a towel and hair up in the towel. Etc etc.
It is never being about sex or trying to turn me on. She
just wants to be Nancy in all ways and this makes her feel good.
It is Friday night and her and I both have dates. I’m in the
kitchen and she comes out.
Damn girl, you are so getting fucked tonight.
It’s a hot night and she is in little to nothing of a dress.
She spins around and goes, you think?
I will not lie; I have been talking to this guy for about a
year. I have been wanting to lose my virginity for years now and I hope he
finds me hot and wants me.
Oh, he will, and use a condom and make sure you have lube.
Don’t trust he is ready and has everything.
Nancy turns red and smiles.
We go our ways.
I get stood up and I’m at the bar drinking. I’m a little
pissed about it as it has been a while for me. I’m kind of newly single and
have not been on a date is about 6 months. We were not anything but you know I
was hoping for a good time.
It hits me I’m drunk and so can’t drive. I call a uber and
head home.
I walk in and Nancy is home also. There is an empty bottle
of wine on the table and another one open. Nancy is on the couch and playing on
the tv is porn.
I say, someone must have had a good night.
She didn’t hear me come in and it startles her and she grabs
the blanket on the back of the couch to cover up and tries to turn the tv.
She is fumbling with the remote and I tell her no. Leave it
on.
I tell her. I got stood up so porn is what I need right now.
She laughs. So did I hence I’m on my 2nd bottle
of wine and watching porn alone.
She is laying on the couch and I grab a drink. I fill her
glass up with wine and I lift her feet and set at the end of the couch with her
feet in my lap.
She goes to set up to make room for me and I say, No just
relax.
I pick the remote back up and start the porn again.
It kind of surprises me that it is normal porn and not gay.
We really do talk about everything and being drunk does not
help. So, I say something about it.
She is like. To tell the truth I do watch both. But when I’
feeling my full Nancy self like tonight. I really do see myself as the woman
and so seeing this makes me think I’m them or fantasize about it. To top it all
off my male part has always been very small and with the hormones. I don’t get
hard anymore. So, they will not want me for my dick.
As we watch, again it is a worm night and when I scared her,
she grabbed the blanket to cover up. So, when I sat at the end with her feet on
me. Half the blanket is on me.
Damn is it hot in here or just me? As I push the blanket off
me and her feet.
She is like right this blanket is killing me. She pushes it
off her also and we keep watching the porn.
This is when I noticed for the first time that night she had
on stocking. They were black with a really cute sexy design in them. I can see
her painted toes through them and I found my eyes running up her legs. She was
still dressed in her dress from the night. But as my eyes ran up her legs, I
found her stockings were thigh highs.
As we watch the porn, I find myself getting turned on more
and more and my eyes shifting from the porn to her feet and legs.
I don’t know if she started it or me but at some point, I
noticed my hips rocking a little and her foot rubbing my hard cock. I looked
down and then up her legs. Her skirt was riding up and just barely covering her
panties.
I’m so hard and turned on from the porn and her her feet and
legs look so sexy. I take a drink and I’m empty.
She sees this and tells me. My turn and gets up and refills
us.
She hands me my drink and looks right at my cock and lays
back down on the couch and slides her feet back on my lap.
I look over at her and her eyes are glued to the tv again.
But I find myself really looking at her. Just a little make up, lip gloss and
makes her lips so wet looking, the light dress laying on her chest and her hard
nipples showing, the dress is even up higher now and her panties are black,
lacy, with a nice camel toe showing, Legs are just parted a little and so tan
at the top, the thigh highs in the right spot holding her legs nice and tight
and looking so smooth, and her cute painted toes right at my cock.
I look back at the tv trying not to stair.
This time I know it is all her and her foot starts rubbing
my cock again. The porn playing goes to full on oral.  It is a guy slowly licking the girl’s lips.
Teasing her as she begs him to make her cum. He would just lick her lips and
ever now and then he would dip his tongue down to her ass and lick from her
hole up between her pussy lips brushing her clit. Her body would shiver and
jump every time.
When the girl moaned out, I swear I hear Nancy moan a little.
I look over and her dress is up a little more and her panties are pulled so
tight to her that it looks like big fat lips. I look at her face and you can
see the lust in her eyes as she watches the guy licking the girl on tv.
The guys tongue licks the girls clit a few times and the
girl whimpers she is going to cum.
Nancy goes. God I wish I knew what that felt like.
I knew what she was saying. She wished she had a pussy and
someone was licking it.
When I looked up her legs and saw what looked like a fat
pussy. I had to taste it.
I picked her foot up and started kissing it. Licking and
sucking my way up her leg. I felt her leg shiver. Her legs open more and I kiss
my way up them. I get all the way to the top of the thigh highs and Nancy’s
hand covers her camel toe and she softly tells me. I’m not a girl.
I look up to her eyes and tell her. Yes, you are. As my lips
touch the inside of her bare thigh for the very first time and I softly kiss,
lick and suck her soft smooth skin just above her thigh highs.
The feel of my lips on her skin made her moan out, “oh fuck
yes” as her hand move up to her tits and she grips her nipples and her legs
open more for me.
I keep kissing her thighs and working my way closer to her
camel toe.
Her panties are laying perfect. The seems running down her
hips and meeting at her taint. The seem holding the small lacy panties together
running down the middle of the front of the panties digging in holding her down
and parting her as it goes down to the gstring making her look like nice fat
lips.
I trace my tongue over her camel toe licking her lips. Just
taking my time teasing her like the porn. I look up her body and one hand is
pulling a nipple through her dress and the other is in her hair as her mouth is
open and moaning.
I just keep licking all around her camel toe. I can now feel
her rocking her hips up trying to make me lick more and harder.
I slide my hands under her legs and lift them up and my
tongue traces the string going in her ass to her little start and I lick it. He
body tells me everything I need to know and her moans are music to my ears.
I now run the tip of my tongue from her star up her camel
toe parting it just like the porn and I feel for the first time the thick
clities she has.
Her body jumps and she cries out.
I move back down and find her star again and run my tongue
up over her clitie.
“OH FFUCK” and her body shakes.
I keep doing this over and over.
She is whimpering saying she is going to cum.
I drive the tip of my tongue in her star and work it a
little and push my tongue hard to her taints and lick my way up.
This time she grabs my head mashing my tongue between her
camel toe as she starts rocking her hip and moaning, she is cummming.
Next thing I know I feel something hot seeping through her
panties all over my tongue and face.
It hits me, she is cumming and she rides it out.
She passes out and I pull away and she the gooy mess oozing
out of her panties.
I get up and go to bed. My cock is in my hand in no time and
I I’m cumming all over myself.  

Source: reddit.com/r/Erotica/comments/qfkgx9/i_guess_it_is_all_about_timing_part_1