Crossdressing the teacher Pt. 03

I didn't know what do think when my wife banned me from the bedroom so I laid on the livingroom couch and tried to get some sleep. So much had happened in the last couple of weeks, from my students Lacey and Jessica tricking me to dress like a girl, to my wife and sister-in-law catching me wearing panties, stockings and lipstick, to watching my wife fuck another guy and then her throwing me out of the bedroom. I am still attracted to women, but I love the feeling of dressing up in sexy clothes and makeup and having good looking men with big cocks hitting on me. Needless to say I didn't get much sleep, tossing and turning on the couch all night.

About 9 am my sister-in-law Erin wakes up and comes into the livingroom.

"Did you have a fight with my sister because she fucked some guy?" she asked.

"No, she doesn't want me to be in the same bed with her since she caught me wearing women's clothes."

"I can understand that, especially after getting fucked by a stranger with a big cock. My sister told me she came twice, that's pretty hot."

I asked Erin how her night was. She said it was ok, but she really wanted Tony to fuck her in the ass, but he wasn't into it.

"That's too much information this early in the morning."

Finally my wife comes out of the bedroom looking well rested and with a big smile on her face, "It's amazing how well one can sleep after cumming twice while getting fucked by a real man with a big cock."

Then Erin asks her sister, "What do you want to do on this beautiful day? "

My wife answers. "I need to go to the mall and go shopping for a few things."

Erin says, "Sounds like fun, maybe Brianna would like to join us, she needs to get some women clothes of her own."

My wife agrees, "What a great idea."

I protest, but the women with have none of that. They are already planning which stores to take me to and what I should buy. This is going to be one embarrassing day.

Then my wife says. "I need to straighten up for awhile, let's leave in about an hour. Brianna can wear her man clothes to the mall while she shops for a new female wardrobe."

Erin and I are having breakfast when my wife walks into the kitchen holding 4 pairs of sexy panties. I completely forgot I left them in the dryer last night.

"What are these? How long have you been wearing panties,and what other secrets have you been hiding?"

I didn't know what to say, so I told them the whole story starting with Lacey wanting help with her school work, but her parents wouldn't let men come to the house. How Jessica dressed me as a woman, how I went to Lacey's house. I didn't mention Lacey promising me a lipstick blowjob ( I was already in enough trouble). I told them that I was forced to give Lacey's brother and friend a blowjob, and then the girls came in a took pictures. Then they blackmailed me into giving them A's, and bought me panties to wear to class everyday.

Erin says, "Wow, I knew you had sucked cock before, I could tell the way you gave Bob a blowjob."

My wife says, "I think I like this Lacey person, I would love to talk with her. After all, if it weren't for your two students I may never have been fucked by Roger last night. Maybe she would like to shopping with us, why don't you call her?"

"Do I have a choice?"

They both reply, "NO"

I pick up the phone to call Lacey. As soon as she answers my wife takes the phone from me.

"Hi Lacey, you don't know me, I am Brianna's wife."

Lacey asks, "Who is Brianna?

"Your math teacher. I understand you took photos of her sucking your brother's cock and blackmailed him into giving you and your friend A's. No, I am not mad, I wanted to thank you for helping him become a sissy. One problem though, you only bought him panties and stockings. He needs more clothes. Would you like to go shopping with us this afternoon?"

"Sure, I would love to. Can I bring Jessica?"

"Yes, and don't forget to bring pictures. Meet us in the mall at Victoria Secret about 1 o'clock"

Erin chimes in and asks, "Do we have time to shave Brianna's legs and pussy?"

My wife says, "No, we can do that when we get home. I can't wait to see everyone's reactions when we go shopping and he asks for women's clothes and makeup."

About 30 minutes later we are in the car driving to the mall. The women are talking a mile a minute about where to go and what to buy me. They are thinking one nice outfit, one sexy one, and one slutty one.

Then my wife adds, "Maybe a manicure and a pedi."

The mall seems crowded, but we find a good parking spot. We enter the mall and go straight to Victoria Secret to meet Lacey and Jessica. My wife gives them both a hug and thanks them again for turning me into Brianna. Erin walks into the store and asks a sales lady, "I need a couple of pairs of panties for me, and about half a dozen for my brother-in-law."

The girls all giggle, but the sales lady keeps a straight face.

"What type of panties do you like?"

"I like just plain ones, but my brother-in-law loves the sexy lacy ones in assorted colors"

The woman guesses my size and brings me assorted panties.

"Anything else?"

My wife chimes in, "I think he could use a couple of bras."

The sales lady measures my chest and brings over a few bras for me to look at.

"Do any of these interest you?"

My wife replies, "He, I mean she will take the black one and the pink one please."

Lacey joins the conversation, "They have really sexy nightgowns here, and how about a garter belt and stockings?"

"That's a great idea. You girls have been such a big help, is there anything you would like. You're teacher is paying."

"We could use some panties and a new bra."

My wife tells them to pick out whatever they like and add it to our cart, then she tells the sales lady we are done and ready to ring up the sale.

Not only am I going to be embarrassed today, this little adventure is going to cost me a lot of money. Next we go into a high end woman's clothing store. My wife tells me to go find a sales person and ask for something nice to wear to a cocktail party.

I find a middle aged attractive sales person and say exactly what my wife told me to.

"Do you have something nice to wear to a cocktail party?"

"Everything we have is nice, is this for your wife, or perhaps your girlfriend?"

I look over to my wife. She gives me a look so I know what I have to say.

"No, the clothes are for me."

She brings me to a fitting room, takes some measurements and then brings out two very pretty outfits.

"Would you like to try them on?"

My wife shakes her head yes, so I take the first dress and go into the changing room. I come out, take the next outfit and go back into the changing room. This time when I come out all the girls say "very pretty", and my wife says.

"She will take both of them, thank you so much for your help."

Next stop, a makeup store.

My wife says to Lacey and Jessica, "why don't you girls help Brianna buy some makeup while Erin and I go shopping on our own. Don't forget to get something nice for yourselves."

The girls immediately go to the counter and tell the woman, "We would like some help buying makeup for our teacher, he, I mean she loves to wear lipstick."

They pick out 3 different shades of lipstick and matching lipgloss. Jessica then says,

"Brianna has such lovely blue eyes, we must buy some eye makeup. I will pick out a nice eyeliner, mascara, and some eye shadow".

The girls give me makeup tips, what color to look pretty, what color to look slutty, what colors to attact guys. We leave the makeup store. Lacey texts my wife to see what our next stop is. My wife texts back to meet them at the nail salon. Ten minutes later we meet my wife and sister-in-law in front of the salon.

"Why don't the 3 of you get a manicure and pedicure. Erin and I met a couple of guys, we will meet you back here in an hour."

So me, Lacey, and Jessica walk into the nail salon. I have no idea what to expect, but the girls give instructions to the manicurist and they tell me to sit back and relax. So I relax, get a few odd looks from the women working there, and an hour later me, Lacey, and Jessica have matching hot pink nails.

It's been an exhausting day, but I am actually getting excited about trying on everything we bought today.

We meet my wife and sister-in-law and they suggest we go out for a drink and grab a bite to eat. They love my nail polish and ask me to put on a matching pink lipstick while we walk to the restaurant. We find a quiet booth in the corner of the restaurant. The waiter comes over to take our drink order and compliments me on my lipstick and nails. When he brings our drinks he smiles at me.

Erin comments, "Looks like our waiter likes Brianna, maybe you should give him your phone number."

After a couple of drinks my wife asks Lacey to show her the pictures of me sucking her brother's cock. Lacey takes out her phone and shows her the video. My wife and Erin are very impressed.

"Jessica, you did an amazing job dressing Brianna. What made you think he would be so into it?"

Jessica answers, "Thanks, I am a theater major taking a class in makeup and costume design, the way our teacher looked at us when we were wearing lipstick made me think he had some kind of fetish."

Erin asks, "Lacey, could your brother tell Brianna was really a guy?"

"No he couldn't, and now he has the biggest crush. Sometimes when he is being an asshole I want to tell him that my sexy teacher is really a guy, but I haven't yet. He is in town this weekend and he really wanted to see him, I mean her."

"So why isn't he seeing her?"

"Because your husband said he/she was busy this weekend."

My wife says, "Why don't you invite him over to our house tonight? You girls can bring your boyfriends and we can have a little party."

Jessica asks, "Can I get there a little early and help Brianna get dressed?"

"Of course you can dear, by the way, what are the chances that you can find a couple of college boys for me and Erin. Preferrably cute with big dicks."

Lacey says, "Consider it done, I know just the 2 guys to bring. They are both on the football team."

Erin replies, "I am getting wet just thinking about it. By the way, we forgot to buy Brianna a slutty outfit and a wig."

Lacey says, "That's ok we know a shady place about 10 minutes from here. Jessica and I will take him while the two of you go home and get ready for the party."

So Lacey and Jessica drive to the not so great part of town. They have me refresh my lipstick and we walk into this X rated store. The girls pick out a wig for me, then have me try on a slutty outfit. As we go to the counter to pay these two sleazy looking guys are staring at the 3 of us.

Lacey turns around and says, "What's the matter with you guys? Haven't you ever seen 2 cute girls and a guy wearing sexy lipstick before?"

The guys look startled, but their jaws drop when Jessica says,"Give me $100 and he will give you both blowjobs."

Lacey laughs, but then one of the guys pulls out a hundred dollar bill.

Before I knew it I was in the back room of this sex shop and two older sleazy men were pulling out their dicks and telling me to suck them. This was certainly not as exciting as sucking on Bob's cock the night before, but I was afraid to say no. I alternated between putting one in my mouth and jerking off the other with my hand. Soon their breathing got faster and they both started to moan. Seconds later they both shot their loads, one down my throat and one on my face. I got off my knees, thanked them both, and ran out of the store. I met the girls by their car. They cleaned the cum off my face, thanked me for making them $100 and started driving me home.

I started to complain a bit on the ride home, "I think your little game has gone too far, those two men were gross"

Lacey says, "Did you think being a woman was all fun and games? I am always fighting off boys trying to kiss me or cop a feel. But it is all worth it when you get all dressed up, meet a cute guy who has a nice cock and knows how to use it. You will feel much better in a few hours after you get to wear your new clothes and we make you up to be the pretty woman you were meant to be."

Strangely, Lacey's words were very comforting and I began to feel excited as we pulled into my driveway and we walked into the house.

Erin asked how things went at the sex shop.

"It went great, we got Brianna a wig and a slutty outfit. A couple of the sleazy men were staring at us, so your husband begged us to let him suck their cocks. That's why her lipstick is all messed up."

Even though that wasn't exactly the truth I didn't have the strength to argue.

Then my wife said to the girls, "Thank you for all your help. Jessica, you can stay here and help my husband transform into beautiful Brianna. Lacey, you can go home find me and Erin our hot dates for tonight, and give your brother the good news that he will be getting his cock sucked."

"I surely will, do you need anything else for the party? drinks or snacks?"

My wife says, "We're good, just bring the hot boys."

"Will do, this should be one epic party."

The first thing my wife and Erin do is run the bath and have me get undressed and sit in the tub. The warm water feels good. They each have a razor as they lather up my legs and begin to shave them.

"Once your legs are shaved you won't believe how good wearing stockings will feel"

It feels odd not having hair on my legs, but it feels way weirder when they decide to shave my pubic hairs. After I dry off my wife hands me a pair of panties.

"Put these on and see how much better they feel when you have a shaved pussy"

Wow, they felt so amazing, and so did the stockings on my shaved legs.

After my wife helps me with the matching bra Erin hands me a dress.

"We decided to go with something sexy rather than slutty, put this on and then see Jessica about your makeup."

I put on the dress then I sit in front of the mirror and wait for Jessica. She looks at me and says, "Love the outfit, now I will help you with your makeup. In about a half hour you will look beautiful."

Some coverup, some blush, then comes eye makeup. Eyeliner, mascara, eye shadow. I don't know how women do this by themselves, but Jessica tells me with a little practice I can do it myself. Then my favorite, lipstick followed by lipgloss. Then a blonde wig.

"Now go show your wife and Erin"

Their jaws drop when I walk into the livingroom and a get a couple of WOWs.

Erin says, "I think the guys are going to pay more attention to Brianna than to us."

Then my wife says, "Let's see if we have some time to teach her how to wear heels."

They give me a very sexy pair of shoes with about 3" heels, but I am having a bit of trouble walking so the women decide to scrap the idea until I have had more time to practice.

I am starting to get nervous and excited with the party being less than an hour away. My wife and Erin get dressed and look very hot. They are both wearing hot cock sucking lipstick.

About a half hour later Lacey shows up with her brother and her boyfriend. I recognized him because he is in one of my classes. I don't think he will recognize me, but I am not sure if Lacey has told me anything about him. Lacey's brother Jack gives me a big hug, a kiss on the lips and tells me he hasn't stopped thinking of me.

Fifteen minutes later the other two boys showed up. They bought a couple of 6 packs. I guess that's what football players do.

Everybody is having fun eating drinking and laughing. Jack is making out with me and feeling me up. I can't believe how turned on I am getting kissing a guy. Erin is making out with one of the football player. I don't know where my wife is.

Lacey comes over and interupts my makeout session. She tells me, "I told my boyfriend about your little secret. He is so turned on, he wants to fuck your ass, and he wants me to watch."

Now I am a little scared, but all I can think of saying is, "What about your brother?"

Lacey says, "Don't worry about him, your wife can handle my brother and the football player."

I kiss Jack and excuse myself.

"I need to talk with Lacey and her boyfriend, don't worry, my wife, I mean Rachel will take care of you."

Fortunately he didn't catch my slip up, and I go with Lacey and her boyfriend to the guest bedroom. I stop by the bathroom and freshen up my lipstick. I am not sure what to expect, but Lacey takes the lead and tries to put me at ease.

"Go ahead Brianna, start kissing my boyfriend."

We start kissing and he immediately puts his tongue in my mouth. After a few minutes he starts feeling me up. Lacey tells me to take off my dress, and I am now sitting on the bed in my bra, panties, and stockings. My bulge in my panties was clearly visible and I was both excited and embarrassed.

"Now suck on his tits.", Lacey orders her boyfriend.

He started licking and sucking on my nipples. I thought I was going to cum when he started rubbing my cock thru the panties, but Lacey stopped him.

"Brianna, take off my boyfriend's pants and underware."

I did as I was told. He had an enormous cock. Lacey said, "Do you like that?"

I shook my head yes.

"Then start sucking on it, but don't let him cum he needs to fuck you."

I start licking up and down his cock. I lick the tip and he starts moaning.

"I can't believe how good you are at giving blowjobs after only doing this for a couple of weeks. You must have watched a lot of sissy porn. Time to stop sucking."

Then she orders her boyfriend to take off my panties. Now I notice that Jessica is in the room, with her camera.

"I didn't want to miss this, I hope you like the makeup job I did on Brianna."

Lacey's boyfriend takes off my panties and bends me over the bed. He starts to fuck my ass. He is so big that it hurts at first, but after a little while it feels amazing. We are both moaning so loud, I don't know who is going to cum first. Then almost simultaneously he screams I'm going to cum while I yell the same. He shoots a giant load into my ass while I cum on the bed sheets. It was my most intense orgasm ever and I nearly pass out on the floor.

It takes me a couple of minutes to recover. I still feel his cum in my ass.

Jessica says, "Congratulations, Brianna has lost her virginity, what do you have to say to Lacey's boyfriend?"

I smile and say, "Thank you for fucking me, I guess you will also get an A in my class."

Everyone laughs.

"Let's get Brianna dressed and get back to the party."

We walk into the livingroom, but nobody is there. We hear a lot of noise from the bedroom so we check it out. There is my wife and Erin with the two football players and Jack. My wife has a cock in her pussy and one in her mouth. Erin is getting fucked by a huge cock and is moaning with delight. Moments later the guy starts cumming, leaving a big load dripping from her pussy.

My wife order, "Don't just stand there Brianna, lick the cum out of Erin's pussy!"

Which I do, much to the delight of Lacey, her boyfriend, and Jessica.

Soon the other football player shoots his load in my wife's pussy. She looks at me, points to her pussy and I rush over to lick it.

Then my wife asks, "Who hasn't cum yet?"

Jack, Lacey, and Jessica raise their hands.

"That doesn't seem fair, does it?"

"Brianna get on your knees and suck Jack's cock"

I am incredibly tired, but I do as I am told.

Then my wife tells Lacey's boyfriend to make Lacey cum.

Then she asks, "Jessica who would you like to have the pleasure of making you cum, me or Erin?"

Jessica answers, "That's a really tough choice, how about both of you?"

What a scene. Me sucking Jack's cock, Lacey getting fucked by her boyfriend, and my wife and sister-in-law licking Jessica's pussy.

No surprise, Jack cums first. I swallow his big load then sit back and watch the others having sex. With a tongue and a dildo in her pussy Jessica cums next. Then Lacey cums.