Sissy Santa

I'm a happily married man in my mid 40's. I have a very hot wife, Lacey, some 6 years younger and 2 teenager daughters, Amanda 18 and Erin 16.. We had a very healthy sex life until about 4 months ago when I lost my job. Lacey is mildly annoyed that she had to start working again, and she has made me feel less of a man staying home doing housework all day and making sure dinner is on the table when she gets home.A few nights ago Amanda suggested that I am the woman in the marraige and I should dress like one around the house. Lacey didn't say anything at dinner, but that night in bed said. " Maybe Amanda was right, you are the woman in this marriage, and I am not a lesbian. Until you find a job I can't see having sex with you in the near future."

Desperate to find work I took a job as Santa Clause at a local shopping mall. So I spend 6 hours a day in a Santa uniform with 2 elves greeting children with a very jolly "Ho, Ho, Ho".

Most nights I get home in time to make dinner for the family and we seem to be having a good time as I tell them stories of what the children are asking for this year.

Amanda still thinks I am the woman in the marraige, and Lacey is still not in the mood to have sex.

Horny and frustrated I head to the mall the next morning. I walk by Victoria Secret, and I find myself staring in the window. Lost in thought I am interrupted by one of Santa's elves. Her name in Jennica, and she is very hot looking. I think she is about 19, home from college for Xmas break.

"You like what you see in the window?"

"Very much." Then for some reason I told her what my daughter said about dressing as a woman."

"That would be hot, you have some feminine features I bet you would make a pretty woman. Have you ever dressed up?"

"No, the thought never crossed my mind until my daughter's comments."

"Never even tried on your wife's panties?"

"No."

"Well we are going to have to change that. I am going to buy you a pair." Then she walks into the store and comes out with a bag. She hands me a pair of sexy pink panties and says. "Go into the restroom and try these on."

Almost as if I were hypnotized I did as she said. I walked into the restroom, took off my pants and put on the panties. They felt amazing as I instantly got a hard on and became more horny.

"You like?" Jennica said.

"Actually I do."

"Told you, Santa. Time to see what the children want for Xmas."

So there I am, sitting in my Santa outfit wearing sexy panties. For the most part I was ok, but Jennica kept whispering perverted thoughts in my ear. "I think I'll call you Sandra Clause or maybe Panty Clause." I managed to get through the day, Ho, ho, hoing away listening to what the children want for Xmas.

When our shift was over Jennica said. "Today was hot, meet me a few minutes earlier tomorrow, I'll have some surprises for you."

I drove home with an erection, but I managed to change out of my panties before my wife got home. That night when I went to bed Lacey was wearing a very sexy nightie. I thought I was horny before, but now I was ready to burst. Thinking I might get lucky after what seemed like months without sex, but Lacey just said goodnight and rolled over and went to sleep.

The next morning I met Jennica outside Victoria Secret. She handed me a bag with a matching black bra and panties. "Put these on, you will love it. The bra may be a little tricky, but you will figure it out."

She was so beautiful it was impossible to say no. I went into the men's room and changed into the bra and panties.

Jennica smiled and squeezed my breasts over the bra. "Very nice, how does it feel?"

"Amazing." I said, and for some reason I started telling her how I haven't had sex in months.

"That's terrible. All I can say is if you let me dress you up I guarantee you will have great sex."

"That's a great offer, but I don't think it's going to happen."

"That's too bad."

Horny as hell and ready to explode I put my Santa outfit on and practice some ho, ho, hos.

Just then Jennica and I see the other elf. Dave is also about 19, trying to make a few extra dollars over Xmas break.

"Santa, are you ok? You seem a little distracted lately."

"He's got a lot on his mind." Jennica chimes in. "He hasn't been laid in awhile."

"Did you really have to say that?"

"I haven't been laid lately either." Says Dave. "My girlfriend is away at college."

"I get laid almost every night." Brags Jennica. "My boyfriend has a great cock."

"I don't think this is appropriate talk before meeting the children. Let's refocus. Ho, ho, ho. Merry Xmas.

As my frustration and horniness increased I began more and more to look forward to my daily meetings with Jennica, wondering what surprises she would have in store next for me.

The next morning I meet Jennica again. This time in addition to a new pair of panties she gives me a pair of pantyhose. "You will love the feeling of stockings."

Once again as if under her hypnotic spell I go to the men's room and try on my new sexy clothes.

"You don't have to tell me, I can tell by the look on your face you love, love the stockings."

"I can't lie, they feel amazing. You are amazing, I wonder what you have in store for me tomorrow."

"Well, just let me know when you are ready to get completely dressed. I can make you look beautiful. Sexy lingerie is only the beginning. There's makeup, sexy dresses, a nice wig. Plus the promise of hot sex."

"It's still not possible. It's getting hard enough to hide the panties and bra, plus now stockings, from my wife. How am I going to hide an entire wardrobe?"

"You can get dressed at my place."

"I can't just disappear and go to your place for the day. As much as I love your offer to dress me and have wild sex it really isn't possible. Lacey is too smart to not figure out something strange is going on."

"Too bad."

It's getting more difficult to focus on my Santa job with Jennica standing a few feet away from me. She has put on some hot lipstick, standing there licking her lips very seductively.

I drive home,put dinner on the table and manage to put away my new panties and stockings a few minutes before my wife gets home. Over dinner Lacey announcers that she and the kids are going to her parents for the weekend to celebrate the holidays and asks me to join them.

"I would love to, but this is the last weekend before Xmas, and the busiest of the year at the mall."

"I understand, everyone will miss you."

"I'll miss all of you too. I really like your parents, maybe we can visit again after the holidays."

I drive to work the next day, still horny and frustrated, excited to tell Jennica the news that my family will be away for the weekend. And like every other day she is standing outside Victoria Secret. Except this time she doesn't have a bag in her hand.

"This morning I want you to come into the store with me."

Again I don't say no. I walk into the store with her. She picks up a few pairs of panties, asking me what I think I would like to wear. I am pretty sure the sales girls can hear her and I am a little embarrassed. We pick out a couple of pairs of panties and walk to the check out counter. As I get ready to pay Jennica picks out a lipstick and hands it to the cashier. "Do you think my friend will look good in this color?'

"I think he will, it will match his panties."

I pay for the items and we walk out of the store. Jennica has a big smile on her face while I am totally embarrassed.

We have some free time so Jennica walks me around the mall window shopping. I finally get the nerve to tell her that my family is going away for the weekend.

"When are they leaving?"

'This afternoon."

"Then you can come to my place after work."

Still not 100% sure I ask again. "Are you still promising sex?"

"Not just sex, great sex. I can go shopping for you during lunch hour. I will buy a few nice outfits. I promise to make you look like a hot woman."

Well, the day seems to take forever, but finally it's time for my finally ho,ho,ho. I can't wait to get out of my Santa suit, excited to get feminized and have sex for the first time in months.

I followed Jennica to her home. She gives me a big kiss and says. "Strip down to your panties."

I take my male clothes off. Wearing only panties she says. "We are going to have to shave you legs."

"What?"

"Trust me. If you think stockings felt amazing before, wait to you feel them after your legs are shaved. Actually take off your panties and jump into the shower."

I get completely naked and she says. "More hair, I am afraid we are going to have to shave your pussy."

"It's not a pussy."

"It's not much of a dick. No wonder Lacey doesn't have sex with you,"

Beginning to wonder what I got myself into, but with the promise of sex I jump into the shower.

Ten minutes later I get out of the shower and Jennica is standing there with a friend.

"This is my friend Olivia. She is going to help. She is an amazing makeup artist. I promise she will make you look beautiful."

Jennica starts putting shaving cream all over my body. Ten minutes later I have no chest hairs and no leg hair. The pubic hair takes a little longer and a lot scarier.

Minutes later I was handed pink panties and black stockings. Jennica was right, the feeling was amazing and soon I had an erection and some pre cum. Jennica puts a finger on my pre cum and sticks it in my mouth. For some reason this gets me more excited. Next she helps me with a matching pink bra.

Jennica puts a few outfits on the bed, and her and Olivia pick out a very sexy short pink dress.

"Very nice." Olivia says. "Time for a manicure."

She places my hands in some lotion, then she files my nails. Jennica hans her a bottle of nail polish, and minutes later I have beautiful pink nails that match my dress, panties and bra.

While we wait for the nail polish to dry Olivia sits me in front of a mirror. She puts some moisturiser on my face, then some kind of blush. Then some eye makeup. Mascara, eyeliner, some eye shadow.

I hear Jennica complimenting the job Olivia is doing.

"It's easy when you have such pretty eyes to start with. You were right, Santa does have some feminine features. Finally comes lipstick and some lipgloss.

Jennica turns me around to look in the mirror. Wow, I couldn't believe what I saw. They transformed me into a very attractive woman.

Jennica thanks Olivia.

"My pleasure I love the challenge of making people look feminine and beautiful. But I think we should give her a name. She doesn't look like a Santa."

'How about Brianna."

"Yes, she looks like a Brianna."

I felt funny being referred to as she, but I looked like a woman.

I said goodbye to Olivia and thanked her.

"My pleasure, have a great night."

Finally I was alone with Jennica, but 5 minutes later the doorbell rang.

Two young men walked in. Jennica introduced them. "Brianna, this is my boyfriend Ethan and her friend Andrew. Ethan and Andrew this is my friend Brianna."

"She is even prettier than you said." Said Ethan.

At this point I was very confused. Jennica got us all some drinks, and the four of us sat on the couch.

A few minutes later Jennica and her boyfriend started making out, and soon they disappeared into the bedroom. So here I am sitting on the couch with a 20 year old boy. Next thing I know he has his arm around my and starts to kiss me. I have to admit, wearing lipstick and having a cute guy kissing me is really turning me on. I open my mouth and our tongues meet. Am I actually making out with a guy?

He starts feeling my breasts. When he starts feeling my stockinged legs I think I am about to explode. I am not sure if he knows I am not a woman so I stop his hand before before it reaches my panties. He takes my hand and puts it over his cock. Even through his pants I can tell his cock is huge.

"Unzip my pants." He says.

I do as he says. I unzip his fly and pull his pants down.

"Play with my cock."

It must be some 10" long. I start rubbing up and down. He is starting to moan so I must be doing something right.

"Do you like my cock?"

"Yes."

"Yes what?"

"Yes, I love your cock."

"Louder."

"Yes, I love your cock."

"What would you like to do with this cock?"

I couldn't believe the words coming out of my mouth. "Please let me suck your big cock."

"Is that why you put on that hot lipstick?"

"Yes, I put on hot lipstick so I could suck on a big cock."

"Go for it slut."

So I take his cock, start licking up and down. I lick his balls then I put his cock in my mouth. I could feel his breathing get faster as he grabs my head and starts fucking my mouth. His moaning and breathing picks up and he shoots his giant load down my throat.

After swallowing cum for the first time I look up and see Jennica and Ethan watching us.

Jennica said to Andrew. "How did Brianna do?"

"Great, are you sure she never sucked cock before."

"Brianna how did you like sucking cock for the first time."

"I'm still a little confused."

"Well, I did promise you great sex. You will never find a nicer cock than Andrew's"

Ethan chimed in. "How did you know you could turn Santa into Brianna and get her to suck cock?"

"I just had a feeling there was sissy potential there by the way he stared into the display at Victoria Secret."

"What about the thing we talked about earlier?" Ethan asked.

"Oh yeah, Brianna, Ethan wants to fuck my ass. I'm not into it tonight so I told him he could fuck you."

"What?"

"You will love it. I love it, Andrew loves it. The way you sucked cock I could tell your sissy adventure has just begun. Now come into the bathroom and let me freshen your lipstick.

In the bathroom Jennica kept saying how proud she was of me. "The way you begged for Andrew's cock let me know what a sissy you could be." She kissed me then freshened my lipstick.

We walked into the livingroom and Jennica had me take off my dress and my panties. Standing in just a bra and stockings Jennica said. "Doesn't Brianna have a nice pussy?"

All of a sudden having my erection called a pussy didn't seem to bother me.

As Andrew started to make out with me again Jennica pulled off Ethan's pants.

"Kiss Ethan's cock and ask him to fuck you."

I kissed the tip of his cock and got excited as I tasted some pre cum. Please fuck me Ethan. Please take my virginity."

Jennica said, "You can do better than that. He loves to be called daddy."

"Please daddy fuck me. I want to be your sissy slut. I got all dressed up in sexy lingerie and lipstick so some big strong daddy would fuck me."

Ethan bent me over and slowly put his big cock in my ass. Moments later he started fucking me harder and faster. I couldn't believe how excited I got. I could feel Ethan was ready to cum. As his cock exploded in my ass I came at the same time and collapsed on the floor.

Jennica said. "Did I tell you that you would love it? Now thank Ethan and Andrew."

"Yes that was great thank you boys."

"You are very welcome. I think you need to lick your come off the floor."

"I was going to remind him after you boys left. See you tomorrow."

Jennica kisses her boyfriend goodbye. Andrew kisses me.

"I guess I should have told you Andrew was gay. He really likes older sissies and he really likes you. I will give you his number. You should call him, he's young, cute, and his family has money. I think the two of you make a nice couple. Now let's lick up your cum.

Once again I do what Jennica says.

"Nice job. It's getting late, youshould get dressed and head home. Tomorrow isgoing to be a very busy day for Santa."

As I grab my clothes to get dressed Jennica stops me. "No, no, not your ugly male clothes Brianna. Put on your pretty woman's clothes."

I do as I am told and get dressed. Jennica kisses me goodbye and whispers in my ear. "You were amazing Brianna, let's do this again soon,"

I walk outside, get in my car, and drive home.

To be continued.