Sissy Santa Pt. 03

My time as a shopping mall Santa was over. While my wife was away Santa's helper elf Jennica had tricked me into wearing sexy lingerie and makeup, and with the help of a friend transformed me into an attractive woman. I didn't realize this transformation would make me become a sissy cock sucking slut.

On Xmas eve she took me and a coworker to a local bar, and before the evening was over I sucked my coworker's cock. After he came on my face Jennica found someone on the bar who would pay $100 for a blow job. I didn't even know his name and at first he was hesitant, but after I freshened up my lipstick and asked him very nicely he let me suck his cock.

Finally Jennica and I were alone. We wished each other happy holidays and I let her know our little feminization experiment was over.

"My wife and kids are coming home tomorrow. I need to find a real job. Giving blow jobs for $10 won't pay the bills."

Jennica was disappointed but seemed to understand. "We'll see, now drive home and don't you dare wipe that come off your face until you get there."

For some reason I could not say no to her. I don't think anyone saw me as I drove home. I walked thru my front door, immediately washed the cum and makeup off my face and took off my cum stained panties. I was completely exhausted and fell asleep in minutes.

The next morning I cleaned the house and waited for my family to come home. I had mixed emotions about the craziness of the past few days, but I was pretty sure my dressing up days were over.

My wife called around noon. They were going to have an early Xmas dinner at her parents and then drive home. She told me not to worry, there would be lots of leftovers so I will have plenty to eat when they got home.

I didn't know what to do about my female clothes and makeup. For some strange reason I packed everything in a box and hid it in the attic with a bunch of my old stuff. Nobody ever goes up there so I felt comfortable it would not be found.

About 6 o'clock I hear a car pull into the driveway. I was excited to see my family and they seemed very happy to see me.

We sat around the dining room table while my family watched me eat. I have to admit it was nice to eat a home cooked meal, even if they were leftovers. The girls were very chatty telling me how much fun they had at their grandparents and showing me the presents they received.

After a couple of hours my wife said. "I'm getting a little tired. Girls why don't you go to your rooms and unpack. I'm going upstairs to talk with your father."

We go up to the bedroom. Thinking I might get lucky, Lacey quickly snaps me back to reality. "I want a divorce!"

"What? Why?"

"I know you were cheating on me."

"What are you talking about?"

"Don't lie. I know you brought a woman back here while I was gone. Cheating is bad enough,but to do it in our house??"

"You're crazy, I never brought a woman here,"

Then Lacey takes out her phone and shows me some pictures. "Our neighbor sent me these pictures of some slutty whore coming to the house."

I was busted. What could I do? I had to tell my wife the truth.

I began to tell Lacey the entire story from the beginning. How Jennica saw me looking in the window of Victoria secret, how she bought me a pair of panties and how everyday she bought me a different piece of sexy lingerie, how she named me Brianna. Of course I left out some details like Jennica promising me amazing sex. I wasn't quite sure she believed me so I went up to the attic and brought her my collection of female clothes.

"Get undressed and put those clothes on." Lacey demands.

I get undressed and a puzzled Lacey says. "Did you shave your body hairs?"

"Jennica and her friend shaved me."

"Ok, get dressed now."

So I put on a pair on panties, and immediately get an erection.

"Look at that, I haven't seen you that hard in years."

I struggle to put on my bra and pantyhose. I put on a red lipstick and explain how Jennica's friend did my eye makeup.

"You can stop now. You don't look half bad."

"I guess I looked better with a wig and eye makeup."

"I guess so. I would like to talk to this Jennica girl."

"What?"

"You heard me. I want to speak with Jennica."

So I hand the phone to Lacey and dial Lacey's number. I can only hear half the conversation between the two of them. They talk for about 15 minutes. When Lacey gets off the phone I ask her what Jennica said.

"You will find out tomorrow. We are meeting her at the mall and taking you shopping."

"Do I have to?"

"Well, if you don't we can always tell our children when I explain why I am filing for divorce."

"I guess I have no choice."

The next morning we get up early. Lacey tells the girls. "Your father and I are going shopping."

"Can we come?" Erin asks.

"Maybe next time."

We make Jennica shortly after the mall opens. Lacey smiles and she and Jennica hug. First stop, Victoria Secret. Jennica had already explained to the sales lady that they were shopping for me. Jennica and Lacey were loving every minute of teasing me. letting anyone who would listen that the sexy lingerie was for me.

It was more of the same at Ulta as the girls picked out makeup. Then off to a boutique dress shop wear I had to dry on about six dresses and model them for the girls. We picked out three outfits that the girls and the sales woman voted were the nicest. As we walked to the register to pay a young woman smiled at us, and her husband winked at me.

Next we stopped for lunch. The waiter took our order.

Jennica said. "That waiter is very cute. Do you think he has a nice cock?"

Lacey answered. "He is cute, but I don't know about his cock."

"Oh, I wasn't asking you, I was asking your husband. So what do you think Brianna."

"I don't know. How long do the two of you plan on torturing me?"

The girls laughed. "I know you want to change into your sissy clothes, but we have special plans after lunch."

The check comes. Jennica says. "Make sure you give the cute waiter a big tip. Maybe you should leave him Lacey's phone number. I have a feeling she is going to need a real man pretty soon."

"I think that's a great idea. I think I'll go to the ladies room and put on that sexy red lipstick that we just bought for Brianna."

I pay the check. Jenncia and Lacey flirt with the waiter, and I worry about what surprise they have for me next.

We walk around the mall for a few more minutes doing some window shopping when the girls tell me my surprise.

"Time for your manicure and pedicure."

We walk into the nail salon. Jennica says. "Tell the receptionist you are here for your 1 o'clock appointment."

"I am here for my 1 o'clock appointment."

"Your name?"

"Brianna."

"Follow me."

The receptionist takes me to the back where two girls sit me down and start pampering me. They massage my hands and feet. I am now totally relaxed as they file my nails and then put on a pretty pink polish.

The girls are very pleased, and I must admit that I love the color. Plus I have been incredibly turned on ever since Lacey flirted with the cute waiter.

"Ready to see your husband get feminized?"

"Looking forward to it."

"Ok, meet me at my house in 10 minutes."

We arrive at Jennica's home and go to her bedroom. I am carrying all the bags that we bought from the mall.

"You know what to do." Jennica says.

I take off all my clothes. Lacey hands me a black pair of sexy panties. I put them on. they feel amazing. Jennica hands me a matching bra, and I put them on.

"Wow, that bra makes it look like he has boobs." Lacey says.

"You should see how excited he, I mean she, gets when a big strong guy feels him up."

Next I put on stockings.

"Very nice." Lacey says. "I love wearing stockings and having a cute guy feel up my legs."

I am so turned on and horny I answer. "So do I."

Jennica says. "Go ahead Lacey, help your husband with his eye makeup."

Mascara, eye shadow, and false eye lashes.

"Some day Brianna will learn to do this herself, but for now show us your lipstick skills."

I put on lipstick and some gloss. Jennica places the blonde wig on my head while my wife looks at me stunned.

"She's beautiful. This is amazing. I always wanted a best girlfriend. Someone to go shopping with. Someone to pick up guys with. Thank you so much Jennica."

Just then Jennica gets a phone call and starts to smile. "I'll call you back."

"That was my friend Jose, he's the quarterback on the football team. They are having an end of the season celebration and he wanted to know if I could bring a couple of slutty women to the party. Are you in."

Lacey jumped at the opportunity. "I'm in, and so is my husband."

"Great, I will call and tell them I have 1 sissy slut and one very hot milf."

"I don't have anything sexy to wear." Lacey says.

"No worries." Answers Jennica. "We are about the same size, come with me I will find something."

Lacey and Jennica disappear for about 30 minutes. When they come back they are both dressed in incredibly sexy outfits.

"What do you think?" Asks Jennica. "Is your wife hot enough to fuck?"

"Oh yes."

"I'm so horny now." Says Lacey. "I don't know if I can wait four more hours until the party."

"That's not a problem. My brother is upstairs. He has a pretty nice cock for a nerd would you like to meet him?"

"Sure."

Jennica calls her brother. "Mikey, can you come downstairs."

Jennica's brother walks down the stairs.

"He's really cute." Lacey says.

Jennica introduces her brother to Lacey. "Mikey this is Lacey, she is very frustrated because her husband became a sissy and can't fuck her anymore. Would you please fuck her while her husband watches."

Mikey takes Lacey's hand and walks her upstairs followed by me and Jennica.

They walk into Mikey's room and immediately start making out. Jennica can tell I am getting excited and warns me. "You better not cum without my permission."

Meanwhile Lacey is already naked as she starts to take Mikey's clothes off. She starts rubbing his erect cock then gets on her knees and starts sucking it. The sight of another man's cock in my wife's mouth is driving me wild.

Finally Jennica says to me. "Is there something you want to say to my brother?"

"Yes. Mikey, please fuck my wife."

"You can do better than that."

"Mikey, pretty please fuck my wife with that big cock of yours. Your sister has helped me become a sissy and I can no longer satisfy my wife. She needs your big young cock in her wet pussy."

As Mikey starts fucking my wife she begins moaning louder and louder. She begins screaming. "Give my that cock, harder, harder." The screaming and moaning gets louder and louder. "I'm going to cum." She starts shaking as she begins to cum.

Mikey looks like he is ready to explode when Jennica yells out. "Cum on those beautiful tits." Mikey pulls his cock from my wife's pussy and shoots a giant load on her breasts.

"Great job. Now, Brianna lick Mikey's cum from your wife's tits. If you lick up every drop maybe I will let you cum."

Lacey is nearly passed out when I start licking Mikey's cum. As I do this Jennica starts to lick Lacey's pussy. This gets my wife excited again, but after about 30 seconds Jennica stops. Lacey seems disappointed, but Jennica says. "Maybe later, I don't want to tire you out before the party."

I finish licking all of the cum. Jennica inspects Lacey's breasts. "Nice job. Now you get to cum."

She puts a plate on the floor. "Cum on this plate then lick it up."

I do as I as told and shoot my cum on to the plate. Then I lick it all up much to the delight of Lacey and Jennica.

With a few hours to go before the party the three of us relax for awhile. The girls go freshen up a bit then they help me with my makeup.

"Are you ready for a wild night?" Jennica asks.

"I'm ready." says Lacey

"Have you ever been to a gang bang?" Jennica says

"I've never had sex with more than one man at a time."

"If you are lucky that is going to change tonight."

As we drive to the house Jennica explains that one of players lives in a huge house just outside of town. His parents are out of town and once a year he throws a giant party for the team. "There are no drugs, lots of bedrooms with different sexual themes."

When we get to the house there are about 20 guys and 4 or 5 women. Jennica's boyfriend is there and he comes over to give her a kiss. Jennica introduces him to Lacey. "This is my boyfriend Ethan,he was the first person to fuck Brianna in the ass, but I am guessing he won't be the last."

We spend the next hour mingling. Finally Jennica asks Lacey. "Which one of the guys would you like fuck."

"They are all so hot, I can't choose just one."

"Ok, let's see what I can do. Stand here for a minute."

Then Jennica stands on a chair and yells. "Can I have your attention. Let me introduce everyone to my friend Lacey. Lacey is a drop dead gorgeous 36 year old milf with a beautiful body."

She has Lacey stand on a chair next to her. She takes off Lacey's dress, and as my wife stands in front of 20 horny guys in just her sexy lingerie.

"Who would like to fuck this beautiful woman."

Twenty hands go up.

"Ok, let's start the bidding at $100."

For the next few minutes I hear everyone shouting numbers.

Finally Jennica announces. "We have 2 winners. Anthony and Tyler each bid $2500."

They both come over and give Lacey a big kiss.

"Ok guys, congratulations. Now take Lacey to room number three."

Tyler lifts Lacey and throws her over his shoulder and he carries her to room number 3. As they walk into the room Jennica turns on the 60" television in the livingroom. There are cameras in room 3 and we are now about to watch my wife have sex with two football studs. As Lacey starts making out with one of the guys, the other is feeling her breasts. As they both take their clothes off Lacey gets on her knees. She is going from cock to cock licking and sucking as the men in the livingroom are cheering. Finally Anthony lifts Lacey up and throws her on the bed.

"Are you ready to get fucked you little whore."

"Yes please fuck me like the whore that I am. My husband is a sissy who can't fuck me. I need lots of big strong young cocks to fuck and suck."

I don't know which guy is which as one is fucking her pussy and the other fucking her mouth.

"This bitch is definitely worth $2,500." Says Tyler.

They turn her over and start fucking her ass. I don't know if I were more turned on or more annoyed because she never let me fuck her ass.

Lacey is moaning and screaming. "Fuck my pussy, please cum in my pussy. Please. I'm your little whore."

As Anthony and Tyler take turns fucking Lacey she screams. "I'm cumming."

Moments later Tyler cums in her pussy and Anthony cums on her face.

A few minutes later the three of them walk out of the room and get a rousing standing ovation.

Lacey takes a bow, gives me a kiss and whispers in my ear. "Lick the cum off my face. Thank you for this wonderful night."

Jennica stands up again." Let's give Lacey a big hand. Now for the highlight of the evening. We have a brand new sissy. She started dressing less than two weeks ago and has only been fucked in the ass once. She loves wearing lipstick and sucking cock. She is looking for a big strong young man to dominate him and be his daddy. What is my bid for Brianna?"

The bidding is going wild. Finally Michael and Jose each bid $3,000. Before they take me to room 4, the spanking room, I have to suck the cocks of the next 5 bidders. I get on my knees and suck the 5 young men one at a time. Each cock is bigger than the one before. Twenty minutes later I have a sore jaw and have swallowed 5 loads of cum.

Lacey asks Jennica. "How did he learn to give blow jobs like that?"

"He's a natural. Once he put on lipstick he couldn't help himself."

"I should have seen this coming. He always seemed to be overly interested when I would put on lipstick or wore stockings. I have been sexually frustrated for a few years now but was afraid to cheat on my husband. There's my boss at work who has been flirting with me for years, now I can fuck him and everyone else in the office."

"You know what else you can do now?"

"What?"

"You can eat pussy! I got a little horny watching you with those two studs."

"That's the least I can do to thank you for all this."

"Sounds like a plan, but first let's watch Jose and Michael fuck your husband's brains out."

I've been given a few minutes to recover from the 5 blow jobs. I go to the ladies room to refresh my lipstick. When I come out Michael and Jose lift me up and carry me to the spanking room. They rip my dress off and throw me on the bed. Michael pulls down my panties.

"Nice ass." Then he begins to smack me ass.

"Ouch." I cry

Then he smacks my ass again.

"Ok little sissy boyare you ready to get that sweet ass fucked."

"Yes."

"i can't hear you."

"Yes. Please fuck my ass. I spent hours getting dressed in this slutty outfit and putting on hot lipstick hoping to find two young studs to fuck me."

"That's better. Now pull down those sexy panties and beg your daddy to fuck that ass."

"Please daddy fuck my ass. I want your big cock in my ass and your friend's cock in my mouth."

Jose takes off his pants. His cock is huge and I get a little nervous.

"I don't know if I can take that big cock in my ass."

"Quiet sissy. Michael's cock is bigger. Bend over."

I bend over and Jose slowly shoves his cock in my ass. It hurts at first, but as he fucks me faster it feels better.

"Do you like my cock in your ass?"

"Yes daddy, yes. Fuck me, fuck me. Fuck me sissy ass."

Then Michael climbs on the bed and sticks his cock in my mouth. It's bigger than Jose's,if that's possible, and I begin to gag a bit.

Jose's keeps fucking me for what feels like an hour. Finally his breathing begins to pick up and moments later he cums in my ass. As I feel his warm cum inside of me I cum and collapse on the bed.

Michael says. "I'm not done yet."

He lifts my ass and starts fucking me. I'm exhausted, but his cock feels so amazing.

All I want to do is please my two daddies, so I lay there moaning and begging for more. Finally Michael cums, Then he and Jose spank my ass a few more times while I thank them.

They put there clothes on and as they leave the room they thank me.

I lay on the bed alone for about ten minutes when the door opens. It's Jennica and Lacey.

"You were amazing. I would never be able to take that big a cock in my ass." Lacey said.

Jennica added. "Michael and Jose loved you. They can't wait to share you with their friends."

"I can't wait either."

Lacey says. "We have one more surprise for you. How would you like to watch me eat Jennica's pussy?"

To be continued