Date: Wed, 27 Sep 2023 11:43:51 +0000
From: Emily Kink <kinkyemily80@proton.me>
Subject: Taby's Sissy - Part 1

The following is a fictional story including incest, crossdressing,
bisexual fun, and will eventually lead to a transgender story. The author
loves communicating with enthusiasts at kinkyemily80@proton.me
Please donate to Nifty to keep this wonderful resource going!

Taby's Sissy - Part 1

Nick was not a stranger to Craigslist hook-ups, but this would be the
first time he was posting rather than simply answering others' posts.
Given his need to stay discrete for work, friends, and family sake, he
had never considered posting but his desire to really find a specific
match was stronger than ever. Having explored his fetish for wearing
lingerie more, he was ready to try playing with other CDs or couples into
the same fetish. He had a specific fantasy he kept dreaming about and
figured it wouldn't hurt to post about it just in case he was able to
get lucky. After all, the choice and power were still in his hands, if
the situation did not feel completely safe, he did not have to engage
with the person responding. After a couple drafts, he finally landed on
the best version of his post: "32/biwm, D&D free, fetish for CD/lingerie
and strap-on fun looking for bi couple with same kinks. Love to play masc
or CD role. Prefer you host, discretion is a must. Hoping for long-term
playmates."

Nick knew to expect a string of one-liners and single guys, which
inevitably came almost immediately after the post went up. There were a
couple single CDs that seemed like a good back-up if a couple could not
be found, but later that night he received a promising email.

"Hi there, we're coming into town in a couple days and may want to
play. Naughty mommy likes to dress her boy toy up in sexy lingerie, and
I've been training his ass for a real cock. We're staying at a local
hotel and could probably host. Let me know if you are interested.
-Tabitha"

Nick loved the idea of finding a first-timer. He had engaged in bi-play
before, but given this would be the first time he would be dressing and
playing, he thought it might put him more at ease knowing the guy he was
playing with was also trying something new. As he responded he did not
want to come off as too eager although he became more and more excited as
he typed.

"Hi Tabitha, that sounds wonderful. I also love role play - especially
with a naughty mommy like yourself. Given what you shared, perhaps our
play could include us boys dressing up and playing together, and we could
take directions from mommy who can use her strap-on on us as a reward for
being two good sissies. I'd prefer you host. I am very discrete and
promise the same in return. -Nick"

Nick anxiously waited for a reply and receive one a couple hours later.

"Nick, we love this idea, but for the first time, we'd prefer that you
play the masc role as my little sissy is earning you as a reward. Are
there any limits to your role-play? The kinkier or taboo the better for
us. You're right, I'm a REALLY naughty mommy. Hosting should not be a
problem. -Taby"

Nick responded the moment he received Tabitha's response - he wanted to
be seen as ready and eager as ever, "Taby, or should I say, mommy, the
kinkier the better for me as well. Typical limits: no pain, blood, scat,
etc. I like dressing and having mommy treat me like a sissy, but not
humiliated - does that make sense? I'd be fine playing the masc role if
my reward can be mommy dressing me up the next time. ;-) Tell me more
about what you two like. It sounds like we may have a good match here.
-Nick."

Given the time of night that Nick responded, he assumed he would have to
wait until the next day to get a response. He could barely keep himself
from hitting the refresh button in his email. In the meantime, he took
down his post to stop the one-liners and singles guys he was still
hearing from. He woke up to a response that almost seemed
too-good-to-be-true.

"Good morning, Nick. "etc." can mean a lot of things, hehe. Perhaps
we'll find out what your real limits are. I complete understand what you
mean by no humiliation. We are not into that either. Here is what we were
thinking - let us know you are into this: Mommy catches her son trying on
her underwear. Between being deprived since her husband left, and always
wanting a daughter, she supports her son's curiosity. She lets him
explore her lingerie and then buys some of his own. Soon, they begin
developing his feminine persona, Emily. After a while, they agree that he
will live as Emily most of the time at home. Mommy helps Emily with
make-up and acting like a sexy little girl. The sexual tension between
Emily and Mommy grows as they continue embracing their new lifestyle, and
Mommy eventually gives in and kisses Emily. Emily, having just hit
puberty, is hornier than ever and wants to go farther with Mommy. They
keep going and eventually get into having Mommy train Emily's ass with
toys (and a lot more in between). Both Mommy and Emily express that they
want to play with a real man, and realize that a guy who also enjoys
lingerie would probably be the safest to play with as they take things to
another level although Emily wanted the reward of being pleasured by a
man/masc role. Thus, we meet you and go from there. I hope that isn't
too much beyond your "etc." -Taby"

Nick, found himself dripping pre-cum from reading the email. He read it
again, this time stroking himself, and came from the amazing fantasy Taby
described. What a fun couple, and what luck in him being able to connect
with them. "God, why did I wait so long to post?" he thought. He
cleaned himself up before responding, "Taby, I hope you won't mind me
sharing that your story made me cum. You are a great couple and no, that
is not outside my "etc" at all. As I said in my original post, I'm
hoping for a long-term thing with new playmates - you two sound like we
would never get bored trying to kinks, role play, ETC, emphasis on the
etc haha. I'm ready to say I'm in if you two are. As I shared before, I
need to be discrete, and thus I don't send pictures before meeting, but
always prefer that we meet somewhere publicly so we can ensure we are
still feeling good about playing together. Perhaps we could grab a drink?
Would that work for you two? -Nick"

Nick was tempted to say, "I don't need to meet, tell me what hotel
you'll be at and I'm there," but despite being completely turned on by
the role play scenario still did not want to come off as too eager or
excited. As luck would have it, Taby must have been checking her email as
Nick responded as she replied within minutes.

"Nick, I'm happy this naughty mommy could turn you on today. Thank you
for offering to meet, that is definitely the safest option. Given my
explanation you can tell this is our first time trying this sort of
thing. We get into town Friday morning and we're staying until Monday
morning. We want to do some shopping on Friday, so the mall would be a
pretty nice place to meet. I just ask a couple favors: first, I want you
to be a surprise for my little sissy so when we meet, he'll be nearby
but won't know I'm meeting you. Second, if we turn out not to be your
cup-of-tea, I hope you will just walk away and agree we will no longer
contact each other. Could you meet us early in the afternoon? -Taby"

Nick was working all day Friday but did not hesitate to immediately
decide to take the afternoon off to make this work, plus he was hoping to
get a jump on the weekend by playing earlier in the day with them. He was
not thrown off by Taby's statement about not contacting each other
although it was probably the strongest statement a potential hook-up had
every clearly articulated. He chalked the comment up to their first-time
jitters.

"Taby, that works perfectly for me. I work a traditional job but taking
the afternoon off is well-worth it. Do you have any suggestions on how we
could make this work so we can meet without tipping off our sissy -
presuming we will like who we see when we meet? - Nick"

Again, Taby responded almost immediately, "Thank you for using some of
your vacation time for us, Mommy will have to make sure we make that up
for you. How about this: meet us at the Dick's Sporting Goods at exactly
1:30pm. I will be in the girls' swimsuit section, and I'll make sure he
is somewhere else. I'll point out where he is so you can discretely
check him out and let me know if you're still in. I'm about 5'6" with
straight blond hair, I'll be the one looking around for you. How does
that sound? -Taby"

"Wow," Nick thought, "she really planned this through." He
appreciated her attention to detail and how clever she apparently was. So
many hook-ups include, just come to my place and let's go, or similar
agreements. Nick expressed that sentiment in his response, "I appreciate
your level of detail and cleverness - what a package, a naughty and
clever Mommy. That works for me, if for some reason we find each other or
you're delayed, I'll check my email. Given that is the day after
tomorrow, is there anything you'd like to know about me or discuss?
-Nick"

Taby answered within minutes, "Great - I will check my email as well. I
would rather not email anymore if that is OK, I'm excited to meet you in
person, and I hope you're into us. See you Friday! -Taby"

Nick responded with a simple message that shared his excited to meet them
as well, and assumed the two would be traveling and thus the reason to
not email any further. The next day and a half seemed to crawl by for
Nick as he anxiously awaited going to the mall. He worked that morning as
planned and went to the mall early to grab lunch. As he walked around to
kill more time, he glanced at every couple he passed wondering if they
could be the ones he'd see at 1:30 in Dick's. He also started to wonder
if the situation was too good to be true: he had a bit less email
back-and-forth with Taby and here they were, about to meet. He tried to
dismiss the doubt, but figured it was worth the risk given the fun they
could have if this turned out to be real. If they no-showed, he would be
disappointed but he could get right back to responding to others who
emailed him about his post.

As the clock struck 1:30pm, Nick walked into the Dick's Sporting Goods
store. He had been in it before but was not familiar with the whole
layout. It did not take long to figure out the direction he needed to go,
and as he approached the girls' swimsuit section, he could see the top
of a blonde woman's head among the tall clothing racks. His relief of
hoping this was Taby, and that they had shown up was immediately replaced
by some self-doubt: what if she did not like the looks of him?

He took a deep breath and walked up to her. In the split-second that
transpired as she turned around, Nick took in the first view of her. She
was a slim, pretty, 30-something-ish, mom-looking type. They smiled at
each other as they realized this was it.

"Taby?" Nick asked.

"Yes Nick, it is great to meet you," Taby started as she looked over
Nick's shoulder, "don't worry Emily is in the sneaker department. I
figured you could walk over and take a look, and if you're still
interested, come back here. If not, can we agree you'll just walk
away?"

"I, uh, I don't think I'm going to feel that way. Not to be too
forward, but you're gorgeous, so I can't imagine Emily would be such a
turn off that I won't be interested," Nick responded.

"Thank you, Nick. You're not so bad yourself," Taby said with a light
laugh, "Well, you're in for a bit of a surprise. This will make sense
once you go to the sneaker department, but let me be very forward with
you, and I hope you'll give us a chance and not be turned off by this.
If you're not into this after what you see, walk away. If you walk away,
don't try to contact me, you won't be able to find us. I know this
sounds strange and like I said I hope I'm not turning you off right now.
You'll understand soon....but I really hope you walk back here...still
interested. I think we can have a lot of fun together."

"Oh, OK," Nick let out slowly, glancing in the direction of the
sneakers although it was not possible to see, "Now I'm really curious,
I hope this isn't some sort of joke."

"No, not at all, I'm sorry I'm not making much sense," Taby said,
beginning to sound like she was second guessing the whole thing.

"It's OK, I know this is your first time. It's ok, really. How will I
know who to look for?" Nick said reassuringly.

"Thanks Nick, really. Well, blond hair almost as long as mine, we're
growing it out so that Emily doesn't need a wig to be feminine. Sport
shorts, blue t-shirt. Remember, they don't know anyone is looking for
them, so you do not have hide or run by," Taby said.

"Great. I'll be right back," Nick said as he put his hand on Taby's
arm, thinking he needed to help her relax.

"I hope so, but please remember what I said," Taby said as Nick began
to walk away.

He turned back to see Taby had a nervous smile on her face. Nick's mind
spun as he walked toward the sneaker section, which felt like a mile
away. What could this possibly be about...walk away and don't try to find
us? In the short walk toward the other end of the store, Nick conjured up
random reasons why he might not be into this guy: is he huge, disabled,
what the hell could it be?

As Nick was able to make out who was around the sneaker section, it was
busier than the other parts of the store. Long blond hair...blue
shirt...long blond hair... Nick couldn't see any guys matching that
description. He looked at all the guys, and then looked around the
adjoining areas of the store, no guys with long blond hair and blue
t-shirt. Then, a head popped up, almost shoulder length blond hair, blue
shirt covering their shoulders. "Oh, he was sitting down trying on
shoes," Nick thought. He walked a little closer and, in an instant,
Taby's email which described the role play shot through Nick's head.

"No. Fucking. Way," Nick muttered aloud. He pictured every email
exchange he had with Taby again. "No way I missed this...she did not
specifically say...but she never said otherwise..."

It wasn't a role play, well, not a complete fantasy anyway. "Emily"
was really Taby's son...just about puberty age as she described. The boy
was oblivious to Nick standing nearby, jaw on the floor, frozen.

"Oh my god," Nick thought, "Fucking run." Nick expected a camera crew
or the police to come running up to him any moment. His eyes darted
around, where the fuck are they? "Fucking run right now," he told
himself again. He stepped back into the nearby baseball section and hid
from the view of the sneaker section, his eyes still darting to every
angle of the store, assuming he had been set up. After a couple deep
breaths, he realized nothing was happening. Just as that thought occurred
to him, the boy smiled at a clerk who was offering to help him, and Nick
could not help but think, "Cute kid."

He stepped backward through the baseball section. "What are you
doing...what are you doing?" he asked himself aggressively. His mind was
telling him to get the fuck out of the store and never look back, but the
rest of him was considering the scenario Taby shared in the email which
Nick thought was just a role play. Nick walked slowly back toward the
girls' swimsuit section. "What are you doing...what are you fucking
doing?" he continued to ask himself. But he knew. Deep down inside he
was turned on. He had experimented at that age, and although he didn't
think of his own mom in that context, he imagined how amazing it would
have been to have Taby as his Mom, and sharing that experience.

He walked back up to Taby, half in a daze. He refocused on her to see the
same nervous smile.

"You didn't walk away," she said.

"I...no...I...sorry...I'm...just...," Nick was still in shock.

"I know this is shocking. I hope you understand why I didn't come right
out and tell you everything...," Taby started.

"I'm sorry if I didn't catch...," Nick started to interrupt.

"No, I was very vague and careful on purpose, I honestly expected this
to be so shocking that you would have no choice but to walk away." Taby
said, still trying to gauge what was going on in Nick's head.

"I...honestly almost...ran away...I thought this was some sort of set up."
Nick said, gathering himself.

"Oh no...not a set up at all...we're real. The story I shared with you is
pretty much exactly our story. Look, I know this is a shock, you can walk
away. I shouldn't have done this. But seriously, I was really careful, I
already deleted that email account, if you walk away we're gone and
you'll never find us. This store doesn't have cameras, I planned this
all very carefully," Taby started to say, getting more frantic with
every word.

"No...Taby...I'm not...I'm not walking away," Nick said, finally able to
look Taby in the eyes again, "I know this isn't right but..." Nick
realized he might have said the wrong thing to Taby given what she was
doing, "Sorry...I..."

"No, I know this isn't right. But this is what it is. I told myself we
shouldn't be doing this about a trillion times, but...it just feels
right. Emily...I've told them we should stop and they begged not to,"
Taby said. Nick looked deep into Taby's eyes, searching for some sort of
warning sign, or a sign she wasn't well, but he just saw a sincere mom.

"So...I'm not walking away...what do we do next?" Nick asked, completely
at a loss of what the next step could actually be.

"Well...we...we did offer to have you over to our hotel," Taby said, "We
actually do have some shopping to do so I figured if this somehow
actually kept going...maybe you could come over this evening?"

Nick glanced down to see Taby holding a girl's one-piece racer swimsuit,
"Is this for Emily?" Nick was trying to break the awkwardness.

Taby giggled, "Um, yes actually, what do you think?" She held up the
swimsuit.

"Maybe Emily and Mommy should find matching suits," Nick suggested, his
mind now open to the fantasy that was forming in his head.

"Good idea- and that's why we have more shopping to do. Emily wants
matching lingerie with her naughty Mommy," Taby replied, also feeling at
a much larger ease, "No one suspects a mommy dragging her son around a
Victoria Secret."

They both chuckled and realized they should be a bit more careful
speaking in the store.

"I would love to come over this evening. Where should I go?" Nick
inquired.

Taby shared their hotel information and suggested Nick arrive at about
7pm. She reminded Nick that it was actually a surprise for Emily,
although Mommy had been hinting about this "reward" for some time now.
Emily might not be completely comfortable given it was their first time
with a man, and she hoped Nick would understand if it didn't work out.
Nick and Taby would meet at the hotel bar.

"I completely understand, you just say the word and I'll walk away
tonight," Nick assured her.

"You're too good to be true," Taby said, giving Nick a kiss on the
cheek.

"I am?" Nick practically shouted, "Part of me still thinks this is a
dream."

Taby reached out and pinched Nick's arm. Just as he was about to mutter
an "Ouch," Taby leaned up and kissed him on the lips, "Nope, we're
wide awake," Taby said with a devilish smile.

"See you tonight, Taby," Nick said stepping away.