Sissy Vacation Pt. 02

Kimmiann and Mistress Suzanne have been at the beach for a few days and kimmiann is dressing femme all the time now. The male clothes are packed away. She wears a silky nightie to bed, she has a pink floral femme robe and she wears sundresses at the house and her bikini on the beach. She has always worn panties at home but now she's wearing a lacy bralette too.

kimmiann feels more like herself than she ever has before. She always knew this is who she was deep down but fear kept her living the life that society taught her to live, instead of the one she wanted. All that changed when she met her Mommy Mistress and she's learning how to embrace her true self.

They've spent another sunny day in the sand and surf and now they're showered and getting ready for dinner. kimmiann loves her bikini tan lines and she begins posing in front of the mirror. Mommy Mistress notices so she gets her phone and takes pictures as kimmiann models for her. Such an attention whore.

Mommy Mistress has laid out kimmiann's clothes, as she always does, but tonight there's no sundress. Tonight there's a cropped halter top and a skimpy little schoolgirl skirt along with white thigh hi hose and pink heels. And the pink gem anal plug that makes kimmiann feel so sexy.

kimmiann is intrigued and curious but she is obedient and always does what her Mistress says. She inserts the plug and puts on the sexy clothes. Her skin is smooth and soft from the shower and lotion. She is still locked in her pink chastity cage.

When she goes out into the living space, she sees the table set for three and her eyes dart to her Mommy Mistress, silently questioning. She understands that Mistress Suzanne makes the rules because she knows best, but her intrigue and curiosity are now laced with fear and uncertainty.

She is dressed in a skimpy little schoolgirl outfit. A lacy bra and thong panties are visible. Her caged clit is hanging out, her ass is showing and while she enjoys slutting around the house privately, this isn't anything she was expecting or is ready for.

Mommy Mistress sees her pet's reaction and laughs.

"I told you earlier this week I was going to find new friends for my kimmiann."

kimmiann isn't sure how she feels. On one hand, it's exciting to think about what her Mistress has planned for her. On the other hand, she doesn't think she's ready to be seen like this or to do what she might be doing tonight.

Sometimes she struggles to fully submit and give up control. She wants to, but it's hard to release herself from her mind and her thoughts.

She knows her Mommy won't let anything bad happen and they negotiated this. She trusts her Mistress implicitly. So while she's a bit uncomfortable, she tries to relax and look forward to what may be turning into a very interesting night indeed.

"I vetted a Daddy for you on Grindr and we've been talking this week. I met with him and he's the perfect date tonight for my femme pet."

kimmiann's mind is racing as her Mommy Mistress sits her down and does a full face of makeup. She does the smoky eyes that kimmiann loves and dark red lipstick.

"I want to see my pet's lipstick all over that cock you're going to suck for me tonight, kimmiann."

The fear and doubt leave her, replaced by excitement and arousal. Her clit begins swelling and dripping in the tight cage, thinking about sucking a stranger's cock tonight. Doing exactly what her Mistress wants her to do.

A knock at the door and suddenly everything becomes way too real.

"kimmiann, on your knees, head down to greet our guest. He is your superior and you will submit to him as you submit to me," Mistress said sternly.

"Yes, Mistress."

"Hello Jack," purrs her Mistress as she opens the door.

kimmiann has a tiny pang of jealousy when he kisses Mommy Mistress and hands her a bottle of wine. But she isn't certain who she's jealous of. They've discussed cuckolding and kimmiann realizes this might be something very exciting to her.

"So this is the sexy little minx who was posing this afternoon?" He looks down at kimmiann and asks "was that for me, baby gurl?"

kimmiann realizes Mommy Mistress sent him the pictures from earlier. She's embarrassed when she looks up at him and says, "Yes Daddy."

Mistress tells kimmiann to get up and they all walk toward the table. kimmiann sits beside her Daddy and her Mistress sits across from them both. Daddy and Mistress had already been talking this week so he spends more time talking to kimmiann, getting to know her.

Mommy Mistress is very pleased with her pet so far and after a light dinner, she brings the wine into the living room for Jack and herself. As they sit down, she tells kimmiann to pose for her Daddy the way she was doing earlier.

At first she's shy and embarrassed and hesitant.

"kimmiann, who is in charge?"

"Mistress Suzanne is in charge."

"I told you to pose for our guest, don't make me punish you. We're having a good time tonight."

Mistress gets the paddle and sits back down.

"kimmiann, pose for your Daddy and me. Show us your clitty. Bend over and show us what a little slut you are. Show us that pretty pink plug you're wearing. Pucker your lips for your Daddy and blow him a kiss."

kimmiann loosens up and starts posing and modeling like the sexy gurl she truly was. She loves the attention and is really starting to feel comfortable in who she is.

Mommy Mistress turns on some pop dance music and all three of them dance together. kimmiann and her Daddy are enjoying each other so Mistress puts on a slow song so the two of them can get closer.

Daddy and kimmiann dance and he has his hands all over her. He keeps rubbing and cupping her ass and playing with her breasts, and rubbing her caged clit.

When the song is over Mommy says, "kneel down in front of your Daddy now, kimmiann." And she freshens up her pet's lipstick.

kimmiann is so excited for what's about to happen. She knows this is exactly what she desires, no matter how hard she tries to pretend it isn't. She's so happy that she found her Mistress and is being trained to be who she's supposed to be.

She's kneeling in front of her Daddy as he and her Mommy Mistress sit next to each other on the sofa. Mommy has undressed and is wearing a long, sheer, black robe over her black bra and panties. Daddy has removed his pants and is naked from the waist down.

His cock is an average length and girth and he doesn't shave. His balls are low hangers, the kind kimmiann always fantasizes about and she can hardly sit still anymore.

Mommy Mistress stands and takes Daddy's cock in her hand and pulls kimmiann toward it. She tells her to open her mouth.

"Suck this cock for me kimmiann. Show your Daddy what a good sissy cocksucker I've trained you to be."

kimmiann eagerly puts her mouth on his cock. She begins greedily licking and sucking. She rolls her tongue all over the head. She licks the shaft from base to tip. She holds and twists the shaft while she licks the head. All the things her Mistress trained her to do.

Mommy Mistress presses her pet's head further down the shaft. "Keep going, I know you can take it all for me, baby gurl."

Mommy Mistress holds her head and kimmiann gags and chokes a little but she doesn't stop. Then Daddy grabs the back of her head and pushes it down harder. kimmiann is all the way to the balls, she has his whole cock in her mouth.

It's hard to breathe but she doesn't want to stop. Her Daddy is moaning and she knows she's doing a good job.

"That's my good gurl, now play with his balls, kimmiann," she hears her Mommy Mistress say breathlessly. She moves her mouth down to his sack and licks and sucks. She strokes his cock while she licks his balls.

"Fuuuck," moans Mommy Mistress. "Your mouth on his cock is going to make me cum." And kimmiann sees her Mistress put her hand in her panties and it only took a few seconds for her to cum.

"Now eat his ass for me, kimmiann."

Daddy stands up and bends over and kimmiann begins to lick all around his asshole. Licking up and down his taint, she spreads his cheeks then presses her tongue against his hole. Finally she pushes her tongue inside his ass, licking, probing.

Daddy's moaning, "Oooh, fuck yes!"

Mommy's rubbing herself to another orgasm.

Daddy turns around and pushes kimmiann's mouth back onto his cock. "Make me cum, baby gurl. That's right. Mmm keep sucking. Rub my balls."

Then he grunts and pumps his load of sticky cum down kimminn's throat. Mommy Mistress makes kimmiann eat her own cum so she's used to it, but this was different.

kimmiann knows she'll never be the same again. She is a sissy faggot, cum swallowing cocksucker and there's no going back.