Date: Mon, 02 Oct 2023 11:48:49 +0000
From: Emily Kink <kinkyemily80@proton.me>
Subject: Taby's Sissy - Part 2

Please post the following story in: Bisexual/Incest, and
Transgender/young friends.

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 2

Nick arrived at the hotel at 7pm and grabbed a table in the hotel bar. He
sat facing the exit, still wondering if he was walking into a trap. Just
as he began to second guess his decision to risk it, Taby walked up to
the bar, looking around for Nick. Nick waved and stood up. Taby was
wearing a tight sexy black dress, almost as if she was going out for the
night. "Fuck she is so cute," he thought, "How the fuck did I get this
lucky?"

"I'm so happy you're here," Taby said, reaching out to give Nick a
hug. Nick hugged her back and then motioned for Taby to sit down.

"Taby, I um, can't help but think this is a set up. It's strange, you
didn't tell me the obvious issue here before we met, but, you know,
I've seen enough set-ups like this on TV that...," Nick started.

"Nick, I totally get it - but that's the key, it would be a strange set
up for me to not share those details and then try to trap you, right?"
Taby tried to assure Nick.

"I don't want to ruin the mood here, but..." Nick stopped as the server
came up to the table. They ordered some wine and Nick started again.

"How can I really...," Nick started.

"We're both taking a risk here, for all I know you're wearing a
wire," Taby said with a smile. Nick reached down and discretely
unbuttoned a couple buttons on his shirt, showing he was not wearing a
wire. They both laughed. He quickly buttoned back up as the server
returned and dropped off the wine.

"I can't ask you to show me you're not wearing a wire under that
dress," Nick said with a smirk.

"No, I'll have to show you that in a bit. But, I can show you this...,"
Taby said as she looked through her phone. She looked around to make sure
no one was too close to the table, and slid the phone across to Nick.
Nick picked it up to see a video was paused, "The volume is really low
so hold it close."

Nick held up the phone and pressed play. The video showed Taby starting
the recording, briefly looking into the camera before pointing it away
from her face. She was laying down on a bed, naked. "Come over here,
Emily," she instructed from behind the phone. Her son walked over,
dressed in a girl's nightgown. "Mommy needs her little sissy to lick
her pussy," she said. As she panned the camera down, she spread her legs
and her son crawled between her legs, burying his face into her bare
pussy. Nick stopped the video - he wanted to watch more but had all the
proof he needed to relax. He slid the phone back to Taby.

"You're a dream come true - you're the naughtiest Mommy I've ever
met," he said.

Taby took a deep breath, "I may have to chug this wine, showing you that
video was probably the riskiest thing I've ever done."

"I think what you and Emily are doing is probably the riskiest," Nick
responded.

"We really just met so know, our secret was much safer than that," Taby
replied.

"Yeah, you're right, but given what I hope we'll be doing tonight,
we're all bound by that secret," Nick started, "and I'm so happy
you're including me. I probably asked myself a thousand times how I got
so lucky since the mall. Why did you respond to my post given the
hundreds on there every day?"

"It was actually Emily's idea. They knew our safest bet would be to
find a guy who was also into dressing, lingerie, and similar kinks. I
didn't tell her that I actually tried the idea, well, until dinner
tonight when I broke the news. They are so excited. They're getting
ready right now," Taby shared.

"Are they always Emily to you? I mean, are they going to eventually live
full-time as a girl? What's their real name?" Nick asked.

"All good questions, I actually don't think so. At home, she is Emily
90% of the time, but they really enjoy their traditional identity as
well. I offered for us to try taking Emily out of the house, but they
said they have no desire to live that way outside of the house...and,
well, for now she'll just be Emily for you," Taby shared.

"Got it. I'm happy to hear Emily is excited for tonight. I hope you
don't mind all the questions," Nick asked.

"Oh God no, I love that I can finally talk about this with someone. My
email to you was the first I ever shared that story with anyone," Taby
said.

"Did it really start and progress like that?" Nick asked, touching
Taby's hand to acknowledge her feelings.

"I left out a thousand details, but yes, I suspected they were playing
with my panties, and then I carefully caught them in the act, not wanting
to scare or shame them. To my surprise, they were wearing my panties and
bra. It was honestly the sweetest thing I had ever seen, and I just held
them forever telling them it was OK. I offered to buy them their own
lingerie, hoping to get them to laugh, but they said yes so fast I knew I
was onto something. Soon we were having dress up time all the time, I
joined in, and then what I shared in my email happened. We talked about
the line we were crossing, and agreed we both wanted to try to go
farther....and well...here we are," Taby shared, "Fuck, what release,
this is better than therapy."

"You're not the naughtiest Mommy I've ever met, you're the most
wonderful Mommy I've ever met. Everyone into this kink dreams of having
an accepting person in their life. I don't think I could ever...you
know...go over that line with my mom, god rest her soul, but that's
amazing. I should say you're the most wonderful and naughtiest Mommy
I've ever met." Nick said, still holding Taby's hand, "So how do we
make this the best time for Emily?"

"You're very sweet, Nick, thank you. Well, I told Emily to get ready,
they've gotten really good at dolling themselves up. We like playing
where Emily is taking directions from Mommy, but not in a dominant way.
I'll get us going but honestly given this is new territory for us,
let's see where it goes. She knows how I set this up, but the little
role-play we want to try is that I met you at the bar and told you about
my little sissy upstairs and how I wanted you to be their reward for
being such a good girl."

"Before I get my hopes up, I told you I was looking for long-term
playmates. Assuming we're going to enjoy each other tonight, do you plan
on coming back to the area?" Nick asked.

"We're here all the time, actually. My family lives here and given
their dad's family left with him, I want them to have a close connection
with my siblings and parents. We only live about an hour away, but I have
enough points from work travel that we always stay for free - almost
every other weekend," Taby replied, "We're off to a good start here,
so I hope we may want to make this more than a one-time thing." Taby
raised her wine glass and Nick did the same, tapping them together,
"Cheers to that!"

They finished their last sips and Taby insisted on paying the bill. Nick
didn't argue knowing Taby had mentioned the travel points she had with
the hotel, but insisted that he would be paying next time. "I'm so
excited for this...and for Emily...," Taby said although she came off as
nervous and excited. Nick took her hand and they held hands as they
walked toward the elevator. Taby smiled at Nick, appreciating the
gesture. The elevator opened and they walked in. As soon as the doors
closed, leaving them alone inside, Taby swung around in front of Nick and
planted a firm kiss on his lips. Nick wrapped his arms around her and
held her tight as they began to make out. The elevator sounded the
expected "ding" as they arrived at Taby's floor. She quickly pulled
back and laughed as if they didn't want to get caught making out in the
elevator.

Just as they arrived at Taby's room and she took out the keycard, she
pointed out to Nick, "We have a nice suite. Let's go in slowly, the
plan is that Emily will go to the bedroom as she hears us coming in."

"Ok," Nick responded in a whisper.

They slowly walked into the room, "We're here sweetheart!" Taby
announced.

"I'm in the bedroom," a young voice said from the adjoining room. The
suite was a fairly large one, with a bathroom right inside the doorway as
usual, and a decent sized living room with a couch and two chairs facing
a TV. The bedroom door was to the right, with the door slightly cracked
open. Taby paused to fiddle with the light switches, leaving on only a
couple recessed lights around the edges of the room, making the room a
romantic level of dim. "That's nice, right?" she asked of Nick.
"Perfect - I'm just going to freshen up," Nick said, stepping into
bathroom.

"Make yourself at home, I'm going to check on Emily," Taby replied.

Nick straightened himself up in the mirror and washed his hands. He was
happy to see a small bottle of mouthwash on the counter which he helped
himself to. His heart began to race realizing what was about to happen.
He stepped out of the bathroom as Taby was coming back into the living
room.

"Oh boy are we in for a treat, she is sexier than ever," Taby said.
Nick smiled with nervous and excited energy. Taby did the same, "Why
don't you have a seat on the couch?" Nick walked over and sat on the
couch.

"Emily, are you ready to join us in the living room?" Taby called over
her shoulder.

"Yes Mommy," Emily responded as they stuck their head through the
door.

As they walked in it was clear Emily was completely transformed from the
boy Nick saw in the mall. Their blonde hair had been slightly curled and
held back on one side with a barrette. They were wearing an almost
matching tight black dress as if they were going clubbing with Taby that
night. They had cute make-up on which covered up any resemblance that
Emily was a boy, and Nick assumed they must be wearing a padded bra given
the cute little boobies showing through their tight dress. Their legs
were covered in shiny nylons.

Nick was sincere with his flattery, "Wow, Emily, you look even prettier
than your mom described you...very sexy!" Emily smiled and walked toward
Taby.

"You mentioned liking matching outfits today, this was Emily's idea,"
Taby said as she put her arm around Emily, "Sweetheart, this is Nick,
he's here for the reward you've earned for being such a wonderful
little sissy for Mommy. Nick, Mommy has been training Emily to be ready
for her first time with a man, and I know she's excited, aren't you,
sweetheart?"

"Yes, Mommy, I'm very excited...and...uh...," Emily started.

"A little nervous?" Nick asked. Emily nodded bashfully.

"There is nothing to be nervous about sweetie, we're going to have fun
tonight," Nick said sweetly.

"Emily likes taking directions from Mommy when we're trying something
new, Nick, so if you don't mind..." Taby asked.

"That sounds like a good plan to me. I bet your Mommy is great at
teaching and directing you, Emily," Nick said. Again, Emily nodded
bashfully.

"I know Emily won't be so shy once we all get comfortable," Taby
started, "Let's turn some music on, we don't want the neighbors
hearing any of our fun."

Taby walked toward the TV and began looking for the music channels.
"Emily, I know we probably won't be relaxed until we jump right in the
deep end. Why don't you sit on Nick's lap, he won't bite."

"I was right, Mommy is great with directions, yes, please get
comfortable, Emily," Nick answered, opening his arms for Emily. Emily
smiled and tucked their hair behind their ear on the side that was not
held by the barrette. Emily walked over and slid onto Nick's lap like a
proper little girl, ensuring her dress stayed in place as they sat. Nick
put one arm around Emily's back, and for the moment put the other to his
side. Clearly looking uncomfortable about what do to next, Nick tried to
comfort Emily. He whispered into their ear, "It's OK, I'm a little
nervous too, but I know your Mom will make sure we have fun." Emily
looked at Nick and smiled. Nick hesitated for a moment, but then gave
Emily a peck on the cheek.

Taby turned around having found a channel that seemed to be playing soft
romantic music, "Is Mommy going to have to tell you two to do
everything?" Taby sat down at the other end of the couch. She put her
arm on the back of the couch to support her leaning head, "All this time
Emily and I have been making out, and Emily has been telling me she
can't wait to make out with a guy...well, here we are sweetheart. Time to
get over being shy."

Nick and Emily both let out a nervous giggle. "OK Emily, show Nick how
great of a kisser you are," Taby encouraged. Nick moved his hand onto
Emily's nylon covered leg and caressed it with his thumb. He very gently
pulled her closer, encouraging her to give in to Taby's direction. Emily
leaned in and closed her eyes as her lips met Nick's. They held a long
kiss until Nick felt her tongue push through his lips and into his mouth.
He reciprocated and in an instant they began to French-kiss deeply. Their
tongues wrestled and Emily reached up to place her hand on the side of
Nick's face as they kissed deeper and deeper, sucking on each other's
tongues.

"Ummm, that's my sexy little sissy," Taby said, taking in the sight,
"See, you had nothing to be nervous about." Emily wrapped her other arm
around Nick's shoulder, getting more comfortable on his lap and in his
arms. Nick pulled her closer and began to caress her leg with his whole
hand, loving the feeling of her thin young legs. He slid his other hand
up Emily's back and into her hair, holding her head close to his as they
continued to make out. Just like Emily, Nick's nervous excitement turned
to arousal. Feeling Emily's young mouth and small tongue against his
felt so naughty. It brought back feelings of the first time he made out
as a child, but felt so much hotter knowing the age difference.

After letting them make out for a bit, Taby interjected, "Let's take a
break so you two can come up for air," she said with a laugh, "plus
Mommy wants a turn." Nick and Emily broke their kiss but were slow to
separate. Taby stood up and put her hand out to Emily. Emily took it and
Taby pulled her off Nick's lap. "I think we said we wanted to put on a
little show for our new friend, right sexy," Taby asked.

"Yes, Mommy," Emily responded sweetly.

Taby started to lead Emily toward the bedroom. Not sure what was
happening, Nick sat still for a moment. Emily turned around with a smile,
"Follow us!" They all walked into the bedroom where porn was playing
quietly on the TV, which was connected to a laptop. "Mommy and Emily
love hearing naughty sounds as we get it on," Taby said as she turned up
the volume a bit, "Make yourself comfy, Nick." Taby motioned for Nick
to sit at the head of the bed. Nick hopped onto the bed and got comfy. As
he turned around, he saw Emily and Taby were already making out at the
foot of the bed. Taby had to bend over to reach Emily's mouth, and she
held Emily's head with her hand. Emily was feeling up her Mommy's ass,
pulling up the bottom of her dress. The fucking sounds and moans from the
TV filled the room with Emily and Taby's sounds adding to the
soundtrack.

Taby reached up and pulled her dress off her shoulders. As it began to
slide down her body with Emily's help, the two paused their kissing.
Emily continued to kiss down Taby's chest and as she did so, took over
pulling down her dress. Emily squeezed and kissed Taby's breasts, and
then pulled down the cups of her bra to get at Taby's nipples. "Oh yes
baby, Mommy loves it when you play with her titties," Taby moaned. Taby
caressed Emily's head as Emily took turns sucking and kissing both of
her Mommy's nipples. Nick admired Taby's more exposed body - she was
wearing a matching lace bra, thong panties, and garter with nylons.

"I hope Emily's outfit matches Mommy's under that dress," Nick
commented.

"Just you wait...and feel free to ditch your clothes too, Nick," Taby
responded, winking at Nick before turning her gaze back down to Emily.
Taby unhooked her bra, giving Emily more access to her breasts, "Mmm
Emily, you're becoming an expert with that little tongue of yours, just
wait until you're working on Nick's cock!" Emily let out a little
moan. Nick unbuttoned his shirt and sat up to take it off. He unbuttoned
his pants and slid them down his legs, kicking them onto the floor. His
hard cock was tenting his boxers, but he purposely did not touch himself
knowing he would not last long given the show he was watching.

"Fuck, you're making Mommy so wet, baby," Taby said as she walked to
the side of the bed and pulled herself up onto it in front of Nick. She
laid back, resting on her elbows, with her legs propped up and wide open.
Emily followed and immediately went to work undoing the clasps of Taby's
garter. "That's right baby...," Taby encouraged. Once all four were
open, Emily pulled off Taby's thong, sliding up and down her propped
legs.

"Yes, eat Mommy's pussy you sexy little sissy," Taby instructed. Emily
sweetly kissed the inside of Taby's knee, and then slid her lips down
her legs toward Taby's pussy. Nick leaned over to find the best angle to
watch. "Give me that talented little tongue of yours, Emily," Taby
continued. Emily did as she was told and began to lick her Mommy's
pussy. Taby began to stroke her head again, grinding her pussy against
her little sissy's face. "Mmm yes, play with Mommy's clitty...fuck
you're so good at this you little slut," Taby moaned. Emily let out a
little snicker, enjoying Taby's compliment.

Nick was not satisfied with the view he had, so he slid off the bed and
walked behind Emily who was bending over to eat Taby's pussy. He stood
over Emily, putting his hands on her hips as he found a great view of the
little sissy licking Taby's clit. He pushed his hard cock against
Emily's dress, and Emily made a little squeal noise given the pleasant
surprise she was feeling.

"Oh I bet that's Nick's hard cock you just felt, wasn't it baby...umm,
give me some of your fingers, sissy," Taby instructed. Emily followed
her mom's instruction and began to finger Taby's pussy as she continued
to lick her clit. "Oh fuck, baby," Taby said, laying completely down.
Nick began to grind Emily a bit, and Taby could feel the push against her
pussy as her young sissy absorbed the pushes of Nick's cock.

"God this feels so good but I don't want to keep my little sissy
waiting any longer," Taby said, beginning to sit up. Emily stood
upright, and Nick held her close, his hands still on her sides. "Turn
around, Emily," Taby said quietly. Emily turned around as Nick kept his
hands on her sides, not wanting to let go of his embrace. He leaned over
and kissed Emily, who put her hands on his naked chest. Taby, sitting on
the edge of the bed behind Emily, began to pull the dress off of Emily's
shoulders.

"Remember you need to speak up, Emily, tell Nick what you want. I know
he'll tell you too," Taby said. Realizing what Taby was doing, Nick
reached up and helped slide off Emily's dress.

"I can't wait to see this matching outfit," Nick said as he stepped
back. As Emily's dress slid to the floor, Nick ran his hands down her
arms to take both her hands, gently pushing her back while holding them
to take a look at her young body. As promised, Emily was wearing a
matching padded bra, thong, garter, and nylons. Her little cock was
pushing through the lacy panties. "What a sexy little sissy body you
have, Emily," Nick commented.

"Thank you!" Emily smiled, "I, um, would, um, I would love to
play...play with your cock." Emily continued to smile but was clearly
getting nervous given the new territory.

"Please do, Emily, I'm so hard from watching you and your mom," Nick
replied.

"Pull off his boxers, sweetheart," Taby whispered.

Emily slid her hands down Nick's torso and pulled down his boxers. His
cock sprang out, just below Emily's young face. "Feel how hard you've
made me, you little sissy," Nick said, following Taby's tone of
instruction. Emily reached out, first with her right hand, and wrapped it
around Nick's rock-hard cock. Nick flexed his cock, making Emily smile
again.

"That's right, stroke my cock," Nick gently instructed. Emily began to
stroke his shaft, and began using her left hand fondle the tip of his
cock with her fingers. "Mmm, that's a good girl," Nick commented. The
"girl" comment made Emily smile even wider. "Mmm, play with my balls
too," Nick instructed. Emily kept stroking his shaft and cupped Nick's
balls, giving them an initial squeeze. She continued to fondle them
before working up the courage to ask, "Can I suck your cock?"

Emily's sweet question sent a shiver up Nick's spine. "Fuck yes, baby,
I can't wait!" he responded.

"Just like we practiced on Mommy's strap-on, Emily," Taby reminded.

Emily bent over, hands still grasping Nick's balls and shaft, and licked
the tip of Nick's cock. The feeling made Nick jump slightly, and Emily
chuckled. She wrapped her young lips around the tip of Nick's cock,
sucking lightly. She slid her hand down to the base of his cock and
pulled as much of his cock into her mouth as she could. His adult cock
filled her little mouth as she began to suck him in and out.

"Oh fuck, yes...," Nick moaned. Nick's moan encouraged Emily to try to
suck him harder, and to try to get more of his cock into her young mouth.
Nick looked down to admire the sight of the young sissy, with her
lipstick coated young lips wrapped around his cock.

"Don't forget about his balls, sissy," Taby instructed, "Nick, Mommy
can be pretty forceful with directions with this little slut so tell
Emily what you really want."

"Yes Emily, kiss my balls like a good sissy," Nick added. Emily pulled
the shaft out of her mouth and pressed her mouth against Nick's balls,
the sack spreading around her face. She licked and kissed them and then
sucked a ball into her mouth once she could find and position it
correctly. "Mmm, you are a natural, Emily," Nick encouraged.

Emily returned to sucking Nick's cock, tilting her head and pulling her
hair back to give Nick and Taby a better view.

"Yes, what a wonderful sissy you've become, sweetheart! You look like a
real pro!" Taby encouraged. Nick moaned. The affirmation Emily received
made her so comfortable she began to try new techniques she had seen in
porn. She stuck out her tongue and tapped the tip of Nick's cock against
it, she rubbed her lips against and licked his shaft, and started to try
deep throating.

"Oh fuck yeah, what a great sissy cocksucker!" Nick exclaimed.

Feeling more comfortable than ever, Emily looked up into Nick's eyes,
"I want you to fuck my mouth, please!" Taby moaned and feigned passing
out on the bed from hearing Emily's request.

"How could I resist such a sexy little sissy?" Nick answered. He put
his fingers through Emily's hair and grabbed onto her head. Emily kept
one hand on the base of Nick's cock and instinctually put her other hand
on the side of Nick's ass and opened her mouth. Nick slowly shoved his
cock to the back of Emily's young mouth until she gagged a little. He
pulled back and slowly thrusted again, and again. Which each thrust,
Emily learned to relax her gag reflex a little although it was impossible
to complete erase. Nick thrusted harder and harder until Emily's gags
suggested she needed a break. Nick pulled out his cock and Emily took a
coughing deep breath, "gahhh."

"More please," Emily said, trying to regain her breath and swallowing
the built-up saliva in her mouth and throat. Nick shoved his cock back
into the little sissy's mouth and went right back to fucking Emily's
face hard. Just as she had heard in her favorite porn videos, Emily made
pleasurable noises as she gagged.

"Fuck, baby, that is so hot," Taby said as she began to finger herself
at the sight of her little sissy getting face-fucked.

Nick pulled out of Emily's throat and mouth, again giving her a break.
"Fuck, I don't want to cum yet...," he said. As she regained her breath
and cleared her throat, "And not down my throat, I want to taste your
cum!" Emily said.

"Oh my fucking God, Emily, you're going to make Mommy cum too!" Taby
said with sexual frustration.

Emily was still panting and trying to regain her breath as Nick leaned up
and shoved his tongue into her mouth, kissing her deeply again. Emily
reached up and wrapped her arms around his shoulders. Feeling Emily
pulling herself up, Nick reached down and lifted Emily up, guiding her
legs around his waist. He held her up by her ass, squeezing her bare,
thong wearing cheeks. He walked them over to the foot of the bed,
avoiding Taby, and slowly bent over to lay Emily down.

"Fuck I love your sexy, young, little sissy, body," Nick half whispered
as he bent over on top of Emily.

"Thank you, Nick," Emily said in her sweetest, flirty voice - looking
Nick in the eyes with her arms still wrapped around his shoulders.

Nick kissed Emily on the lips and then on her neck, shoulders, and chest.
He traced his lips around her bra and back up to her neck.

"Don't you just love her perfectly pure young skin?" Taby inquired.

"Um hmm," Nick said, not wanting to stop to speak. He kissed down the
center of her chest, past her bra, and down her stomach. Emily moved her
arms from Nick's shoulders to run her hands through his hair. Nicked
continued to kiss down toward Emily's thong. When he reached the edge of
it, he paused to pull Emily's nylon covered legs over his shoulders.
Emily let out a giggle and a moan.

"Mmmm is right, baby, tell Nick what you want," Taby reminded.

"I want you to suck my sissy clit, please," Emily said again in her
sweet flirty voice.

"Your sissy clit, fuck, you're so fucking cute," Nick replied. Kissing
the insides of her legs above her nylons, "and fucking sexy." Keeping
her legs over his shoulders, Nick pulled down Emily's panties, tucking
them under her little balls. Her smooth little pubescent cock was hard.
Nick again traced his lips around her bare and pure smooth skin, humming
with pleasure at how perfect it was. He licked the tip of Emily's sissy
clit, making her jump in the same way Nick did with the first touch. He
sucked the young cock into his mouth and began to suck it in and out,
rubbing his tongue against it, making Emily moan. Nick ran his hands up
Emily's sides and began to rub her sides and tummy, loving the feeling
of her smooth body. Emily put her hands on top of his and moaned with
each suck.

Nick paused to play with her balls with this tongue. He sucked her small
sack into this mouth and played with her tiny balls with is tongue. Taby
slid closer and began to make out with Emily. Nick returned to sucking on
the smooth little clitty.

It did not take too long for Emily to get to the edge of cuming. She
gently pushed on Nick's head before it was too late, "Mmm stop, I
don't want to yet."

"Mmm, as long as you're saving it for me, sexy," Nick responded,
kissing her legs and around her crotch.

"I want you to fuck me first," Emily responded.

"Mmm, just what Mommy has been really training you for, my sexy little
sissy," Taby inserted.

Nick gently slid Emily's legs off his shoulders and began to unclasp the
garter from her nylons. Taby worked on the leg closest to her. As soon as
they were free, Nick began to pull down the thong, Emily pushed her
pelvis in the air to assist.

"Turn over, sexy," Nick instructed. Emily scooted backwards and rolled
over. She got onto her hands and knees, pulling up on her nylons to keep
them in place. Taby followed by Emily's side and unclamped the back of
the now useless garter, pulling it away. Nick crawled onto the bed behind
Emily and bent over her bare ass. Emily grabbed a pillow, hugging it as
she laid down still on her knees to keep her ass in the air - a position
she found to be comfortable during Mommy's strap-on trainings. Nick
kissed Emily's lower back just above her crack, and then kissed and
squeezed her ass cheeks. He pulled her ass open and held it with his
thumbs. One look at Emily's perfectly pure-looking pink asshole and Nick
could not resist thrusting his tongue inside. Emily immediately moaned at
the sensation, she turned her face, resting on the pillow, and smiled
toward Taby.

"What a lucky little sissy you are," Taby said, stroking Emily's face
with her finger.

"Mmmmm...," Emily responded.

As Nick licked Emily's smooth hole, her Mommy's training kicked in and
she worked to loosen her sphincter muscles. Nick hummed as he felt her
working. Taby rolled over for a moment and grabbed a bottle of lube that
was sitting on the nightstand. She tapped Nick on the arm with it, and he
stopped to take the bottle from her. Nick lubed up his middle finger and
dropped a bit directly onto Emily's hole. The cold lube made Emily
giggle. Gently squeezing her asscheek as he opened her butt again, Nick
rubbed the tip of his finger around the tiny hole before closely pushing
it in. Emily expertly accepted it.

"Mmm, what a great sissy you are," Nick encouraged.

He fucked Emily's asshole with his finger while pouring a little more
lube on it and the adjoining ring-finger. He pulled out his finger and
rubbed her hole with both fingers before gently pushing in both of them.
Emily braced her body knowing what was coming, but concentrated on
accepting the fingers. Nick could feel her tight hole resisting at first
but then slowly loosening up.

"That's right sweetheart, you've had bigger toys than that, good
girl," Taby said.

Nick fucked Emily with his fingers, trying to expand them a bit as she
worked to relax and loosen up her hole. "Mmm, you two make a great
team," Taby said with a laugh.

"Mommy trained Emily well is more like it," Nick responded.

Nick got to the point where he could fully fuck Emily's little hole with
his two fingers. "I think this little sissy slut is ready for my cock,"
Nick announced.

"Mmm, yes please fuck me!" Emily said enthusiastically.

"My sexy little sissy has been hoping for this for a while, I can't
wait to see how well she can take your cock, Nick," Taby added.

Nick pulled out his fingers, leaving Emily's sexy little hole slightly
gaping. Nick quickly poured some lube into the sweet little pink hole
before lubing up his cock. Emily shook her little tush with excitement as
Nick worked the lube all over his cock. Holding Emily's ass steady, he
guided his cock to her tight little hole. Although Nick was not
self-conscious over his size, he thought that this was certainly a good
time that he was not hung like a porn-star. He trusted his cock wouldn't
be too painful for Emily to take.

Nick was able to get enough of his tip to squeeze into Emily's hole that
he moved his hands to help hold her ass wide open. He carefully pushed as
Emily began to squirm and wince as the thick adult cock squeezed into her
young tight hole. "Good girl...gooood girrrrrl," Taby encouraged. The
ridge of Nick's cock head finally popped through Emily's ass. Emily let
out a little pleasurable moan, and Nick took a break before going
further, rubbing Emily's back.

"Ready, sexy?" Nick asked.

"Yes, please," Emily lightly moaned.

With his hands on Emily's sides, Nick held her as he pushed his cock
deeper into her asshole. Emily continued to wince and make sweet little
noises as she did her best to take the hard adult cock in her young ass.
Taby caressed her face and hair helping her little sissy to relax. Emily
took the cock like a pro and before long, all of Nick's cock was fully
in her ass. "Fuck, Emily, you feel so good, are you ok?" Nick asked.

"Mmmm... yessss," Emily responded.

Nick poured more lube on his cock as he pulled it out of Emily ass. He
quickly pushed it back in before Emily's ass would tighten up again.
"Tell me if you need me to stop," Nick said. Emily just moaned in
response.

"I want to hear you encourage Nick like you always encourage Mommy,"
Taby added.

Nick thrusted his cock back into Emily a bit harder, and then faster.
Emily moaned with every thrust, which Nick took as a signal that he could
go harder and faster.

"Mmmm....yes...fuck me...ugh...fuck me...," Emily tried to say as she
grunted. Nick began to moan as well, "Mmmm....good sissy....mmmmm....take
that cock you little slut..."

Taby fingered herself and also began to moan, beginning to climax from
the sight, "Fuck baby, yeah, fuck, mmmm, I love you my little sissy
slut, mmmm I love seeing you get fucked!"

"Fuuuck...yesss....fuck my little sissy hole.....fuck my sissy
pussy....mmmm....," Emily continued to moan.

Nick was not going to last much longer, the tightness of Emily's tight
and perfect asshole felt amazing, "Where should I cum? Where do you want
my cum you little slut?"

"In my mouth! I want to taste your cum please!" Emily moaned sweetly,
half muffled from the pillow.

"Mmmm, let's have you turn over then," Nick said, slightly out of
breath. He pulled his cock out of Emily's ass and helped her roll onto
her back. Nick reached over and grabbed the pillow and slid it under her
ass, Emily knowing to lift herself up. Like the perfect little sissy, she
also took the opportunity to pull her nylons back up which had slid down
her legs a bit. Nick went to resume fucking and realized they needed
another pillow. Taby noticed the predicament as well and grabbed one.
Nick took it and propped up Emily's young body even more. Taby also took
the opportunity to kiss Emily now that she was lying face up. When they
finished, Nick also leaned up and kissed Emily, and said gently, "Be
ready to sit up, baby."

Nick stroked his cock to get it completely hard again. He guided Emily's
legs into the air and resting against his body. Nick pushed his cock into
her hole and once slightly inside, grabbed Emily's sides for stability.
"Keep telling us how much you like this, sissy," Nick instructed. As he
began to fuck Emily harder and hard again, Emily followed the
instructions.

"Mmmm....yes...I love your cock in my pussy....mmmm fuck...fuck I love you
fucking my sissy pussy...," Emily moaned. Then Emily pushed Nick over the
line: just as their eyes met, Emily put her hands over Nick's on her
sides, smiled at him and said sweetly, "Mmmm, I can't wait to taste
your hot cum, Nick."

"Fuuuuck, now!" Nick cried out. He pulled his cock out of Emily's
tight hole and Emily quickly sprang up, so quickly that Taby jolted out
of the way even though she wasn't. Emily grabbed Nick's cock and sucked
his tip into her mouth. Nick grabbed Emily's head and began to fuck her
mouth while Emily held onto his shaft to stop him from going all the way
down her throat. In the instant he felt her warm mouth and tongue, Nick
came, shooting a giant load of hot cum into Emily's mouth.

"Mmm fuck....fuck....mmm," he moaned. Emily moaned as she felt her little
mouth fill with the hot load. Nick held her head as he pumped every drop
of his cum into her willing mouth. As he finished, he let go of Emily's
head, but Taby quickly jumped in, turning Emily's face toward her to
kiss her and share in Nick's cum. Taby moaned as she tasted the cum from
Emily's mouth. Emily pulled away from Taby after a moment and went back
to Nick's cock, wanting to lick it clean.

"Mmmm, what a sweet sissy you are," Nick commented, running his fingers
through Emily's hair. Normally, after such an amazing orgasm, Nick would
feel the typical deflation, but he was energized. He leaned down and
pulled Emily's face upward, also searching for a kiss. They made out
sweetly, both moaning with delight.

Nick pulled back, "Now I want your cum."

"And I want to show that sexy ass some care," Taby added.

"Mmmm, I want to cum first," Emily answered, laying back and spreading
her legs.

Nick immediately laid down to suck Emily. He sucked her young cock into
his mouth and began sucking hard. Emily began thrusting her hips and
squeezed her smooth legs against Nick's head, her nylons now hanging
around her ankles. Nick slid his hands under her ass and squeezed as he
sucked her harder and faster. It did not take long for her to begin
cumming, grabbing Nick's hair with her hands as she grunted and came.
Nick moaned as he felt the little cock pump cum into his mouth. Nick
lifted his head and motioned to Taby. Loving the offer of another cum
kiss, Taby quickly moved and the two exchanged the little sissy's cum
between their mouths before swallowing every drop.

Nick crawled up and laid next to Emily. He pulled her over and she rolled
on top of him, kissing him for a moment before resting her head on his
chest and shoulder, her arms and legs draped over Nick's sides. Nick
gently rubbed her back and caressed her head. Taby knelt over her little
sissy's ass and gently spread her cheeks. She began to gently lick and
tongue-fuck her little hole, still red from Nick's hard fucking. Emily
smiled and moaned with bliss given all the aftercare attention she was
receiving. If her Mommy wasn't tonguing her ass, Emily probably could
have fallen asleep.

"Mommy, can Nick sleep over?" Emily asked.

Nick was open to the idea, but waited for Taby to speak. "Oh sweetheart,
we actually need to get up really early tomorrow to get to your aunt's
house, but I hope Nick would like to play with us again tomorrow evening.
Maybe we could plan on him spending the whole night with us," Taby
answered.

"I love that idea, I had so much fun tonight, and we all need to get
some rest, right?" Nick asked, snuggling Emily close. Emily hugged him
back with her whole body.

"Well, that's the plan then," Taby said, "Emily, say goodnight to
Nick and go get cleaned up."

"Yes Mommy," Emily said before leaning up to give Nick a kiss,
"Goodnight!"

"Goodnight you sexy little sissy," Nick said before kissing Emily back
one more time.

Emily slid off Nick and off the bed. She gathered her panties, garter,
and dress, and headed into the bathroom. Taby slid up Nick's body and
snuggled up with him.

"I have something to tell you...I'm really a cop, this was all a set
up," Taby said dramatically.

"Well fuck, you better handcuff me," Nick replied with a laugh.

"No, that's tomorrow's fun," Taby replied with a laugh, "Thank you,
Nick, you were better with Emily than either of us imagined. I hope you
want us to be your long-term playmates..."

Nick pulled Taby close and kissed her deeply. She rolled on top of him
and kissed him back. After a moment, they both relaxed their embrace.

"Of course I do...I would have stayed for more fun tonight if you didn't
have early plans tomorrow," Nick replied.

"Oh I wish we didn't, but we are just beginning, we'll have plenty of
fun together," Taby assured Nick, finishing with a kiss.

"I better get going before Emily gets out of the bathroom, I may not be
able to resist them," Nick said.

"I don't think I'll be able to either, imagine having that sexy little
sissy with you all the time!" Taby responded.

They both got up and gathered their clothing. Nick got dressed and headed
for the door. Taby followed having only put back on her panties. They
kissed goodnight and Nick asked Taby to give Emily one more kiss for him.
She agreed, and realized they should exchange phone numbers, which they
immediately put into their phones. They kissed one last time, and Nick
walked out.