The Bet

I am a mid 30 year old male married to my 30 year old very attractive wife for 6 years. Our sex life is pretty good, I think I have more of a kinky side than she does, but she still turns me on. One complaint I do have is that my wife hates to give blow jobs. If I am lucky I will get one on my birthday.

Mid October this year my alma mater played my wife's alma mater in football. To make the game more interesting I suggest we make a bet on the game. To my surprise she agreed.

"What would you like to bet?" She asked.

"How about a lipstick blowjob if my school wins."

"What about if my school wins?"

"What do you want?" I ask her.

"How about if my school wins, we have a Halloween party at the house and you dress up as a women."

Considering my school was a 4 touchdown favorite a happily took the bet.

As my team jumped out to a 10 point lead I started to tease my wife. "That new red lipstick you bought will look really nice sucking my cock."

"I am not worried,my school is a good 2nd half team, I think you will be the one wearing hot lipstick."

Well, my wife's school scored 2 late touchdowns to win the game, and immediately she went into "what will I make you wear" mode.

That night we were going out to dinner with our friends Jessica and Michael. As we were getting dressed my wife came into the bedroom wearing the hot red lipstick she had purchased. Then she smiled and handed me a pair of silky pink panties. "Put these on, you will love the way feel." After a mild protest she said. "You lost the bet and you promised to dress like a woman. The party is in a couple of weeks. You can't become an attractive woman overnight."

I reluctantly put the panties on and my wife immediately noticed an erection. "I told you that you would love the way they feel, this is going to be fun."

Dinner was very pleasant. Every now and then my wife would let her hand rub against my panties. Then she whispered in my ear. "This is hot, looks like both of us have wet panties."

As the meal ended and we were waiting for the check my wife and Jessica excused themselves and went to the ladies room. When they came back I noticed they had both refreshed their lipsticks. Michael left to get the car. The girls were smiling and Jessica said. " Can I see your panties?"

I turned bright red and my wife said. "She's my best friend, I had to tell her." Then she quickly unzipped my pants to show her friend my panties.

"Wow, that's hot." Jessica said. "My husband loves when I wear sexy lingerie, maybe I can get him to wear my panties. I'm really looking forward to your party, maybe me, you, and your husband can go shopping this week."

"That would be fantastic." My wife said. "You have such good taste in clothes You could really help us pull this off."

"You husband has some feminine features. I am sure we can transform him into an attractive woman."

As my wife and I drove home she rubbed my panties a few more times. When we walked into the house I thought I was going to explode. Then my wife said. "Sorry, I don't think I can have sex with a man wearing panties."

"You said your panties were wet. I thought that meant you were excited?"

"I was excited, did you see our hot looking waiter. Jessica slipped her phone number down his pants when we went to the ladies room. She said his cock was huge. Maybe he likes men wearing panties."

'What's got into you tonight?" I ask

"Just having fun honey, enjoying my victory over your school. Just thinking how you keep asking for blowjobs and wondering what horny men would think seeing you wearing hot lipstick."

I was both excited and embarrassed at the same time. Then my wife said. "I sense a little frustration. If you put on some lipstick and smell my wet panties I will let you masturbate."

I was so horny I did exactly that. "Pink lipstick to match your pink panties." She said. She applied the lipstick and said. "I think you will make a very pretty young lady, now go make yourself cum."

I started stroking my cock and came in about 30 seconds.

The next morning as I got ready to get dressed I noticed that all my underware had been replaced by panties. "You don't need ugly mens underware anymore." My wife said. "You love wearing panties so much, you should do it everyday. Do you like all the different colors I bought you? You did like wearing my panties last night, didn't you dear." I had to admit they did feel nice and definitely got me excited. Then she said. "Imagine how sexy they will feel when we shave your pussy."

"What did you say."

"Imagine how sexy they feel when we shave your pussy. We have less than 2 weeks before our party, I was thinking today we can shave your legs and pussy, then you can try on some different panties and learn how to put on stockings."

My wife ran a hot bath and ordered me to sit in the tub. She then proceeded to shave my legs and all my pubic hairs. When I got out of the tub she handed me a pair of black panties and matching pantyhose. I put the panties on. My wife was right, they felt even more amazing now that I had shaved. Then she helped me with the pantyhose. The stockings felt amazing, and my wife smiled as she saw my erection and the precum. "I told you that you would love the way it would feel after you shaved. Later you will practice putting on stockings and pantyhose by yourself."

Then my wife called her friend Jessica. I could hear the excitement in her voice as she told her of our progress. "Yes, I shaved his legs and pussy. He is wearing black panties and pantyhose. Last night he wore my slutty red lipstick and jerked off while smelling my panties. That's a great idea. I'll talk to you later."

"What's a great idea?" I asked, "And do you have to tell Jessica everything?"

"She said I should take a picture and send it to her, and maybe later we can go to Victoria secret and buy some sexy lingerie."

I tried to object, but she just said. "Stop whining, put on this lipstick and smile."

Next thing I know I am wearing lipstick and my wife is taking my picture. She texts the picture to Jessica and Jessica immediately texts back. "That is so hot, should I show my husband?"

Next thing I know, my wife and I are driving to the mall and we meet Jessica in front of Victoria secret.

Jessica tells me. "It's your lucky day, they are having a big sale today."

We walk in and my wife finds a sales lady. "We need to buy some panties for my husband. He lost a bet and he has to dress as a woman for a night."

"Has he worn panties before?" The sales lady asks.

"Yes, and he loves it. He's wearing panties now, and stockings."

"That's hot, believe it or not we do get a lot of men here buying sexy lingerie."

"Really?" Jessica asks.

"Oh yes. Sometimes they come in with their wives or girlfriends, sometimes they come in alone and say they are shopping for their wives and girlfriends, but I can tell when it's for them." Then she looks at me and says. "You are being very quiet, do any of these panties interest you?"

"I am a little embarrassed, I will let my wife and Jessica pick them for me."

"Don't be embarrassed, you have some feminine features, I think you will make a very pretty woman. You have very beautiful eyes, I would love to see them made up. Now tell me, what color panties would you like?"

So there I am picking out about a half dozen panties. A couple of red, a pink, purple, and black. My wife smiles and tells the sales lady to pick a couple of thongs.

"How about some matching bras?" The sales lady asks.

"Great idea." My wife answers.

So not only is this going to be embarrassing, it's going to be expensive. About twenty minutes later I walk out with panties, bras, a slip, and a nightgown. And my wife and Jessica have a new friend, Lacey the sales lady who promises to call when the store gets some new sexy items in stock.

As we leave Victoria secret Jessica suggests we continue shopping. Despite my protests my wife says. "One more store honey, would you like to get some makeup or shop for a nice outift."

Since I have no choice I pick the makeup store. Much like Victoria secret, my wife and Jessica embarrass me in front of the woman behind the counter. Jessica suggests the three of us buy matching lipsticks. Then it's eye makeup, blushes and stuff that I have no idea what it does.

As we walk back to the car, I am carrying all the bags of goodies while the girls are talking about the waiter they flirted with the night before.

Jessica said. "Charlie called my this morning. I invited him over to our house next Saturday while Michael is out of town. Do you think he will like my new lipstick?"

I said. "Are you asking me or my wife?"

"Both of you."

My wife answered. "I am sure he will love it, especially when you are sucking his cock."

"Do you want to join us? I am sure he would love a 3 some. It's a shame you don't like to suck cock."

"I would love to join you, but I still have a lot of work to do feminizing my husband."

As we drive home my wife asks me if I enjoyed our little shopping spree.

"I guess so, I do enjoy walking around in panties and stockings. I don't think I had as much fun as you and Jessica. I can't believe she is going to cheat on her husband with that waiter."

"She loves sucking cock and fucking younger guys. I really think she is jealous of us. She would love to see Michael dressed up. Sometimes she teases him and calls him Michelle. Which reminds me, we need to find a female name for you."

When we get home she lays out all the clothes and makeup on our bed. She orders me to get undressed. First she hands me a pair of red panties and I put them on. Next she hands me stockings and walks me thru putting them on by myself. Next she helps me with a matching red bra. "It's tricky, but you will soon be able to do this without help." Next she hands me a red lipstick. "You have watched me put on lipstick, I think you can do this by yourself." As I begin to put on lipstick my wife is complimenting me. "That was great. I am going to help you with your eyes. Pay attention, this is going to take a lot of practice." She takes her time. Eyeliner, mascara, eye shadow. When she's done she tells me to look in the mirror. "You have such beautiful eyes, they look even better with makeup."

My eyes do look very feminine, and all I can think of saying is, "thank you".

"That's enough for today, now smile so I can take a picture and send it to Jessica."

I smile, she takes my picture and texts it to Jessica. Seconds later the phone rings and my wife puts the call on speaker. "Your husband looks amazing. If he had a wig he could surely pass as a woman."

"I agree, do you think he should be a blonde or brunette? I think we should give him a new name and stop calling him my husband."

"I was thinking about both of those questions. One, I think he, I mean she should be a blonde and we should call her Brianna."

"That's perfect." My wife says. "We need to let him jerk off now, I'll talk to you tomorrow."

She hangs up the phone and asks. "Brianna, do you want to cum?"

"Yes, are you sure we can't have sex?"

"You know I can't have sex with anyone wearing panties. How bad do you want to cum?"

"I am ready to explode."

"Ok, freshen up your lipstick and meet me back on the bed."

I put on my lipstick and meet my wife on the bed. She takes off her wet panties has me smell them. "Today we will try something new, you will jerk off into my hands, and then I will have you lick up your cum."

"I don't want to lick up my cum I protested."

"Ok, I guess Brianna doesn't want to cum. Just give me my panties back and we'll get ready to go to bed."

"Ok,ok,ok, I'll do it."

"Do what?"

"I'll cum in your hands."

"Say please."

"Please let me cum in your hands."

"Ok Brianna stroke that cock. Cum for me you little slut."

Again I cum in less then a minute. Then my wife puts her hands in my face and orders me to lick up my cum. In all the excitement I lick up every drop.

"Good girl, Brianna. You have become quite the little slut."

I couldn't figure out what was going on, but the more my wife degraded me or demanded of me the more turned on I became, and now she had me enjoying licking my own cum.

The next morning I had to go to work, but that didn't stop my wife from laying out the sexy lingerie I needed to wear under my suit. She laid out matching panties and bra and complimented me on how well I put on my stockings. She then got dressed in the exact same lingerie and said. "We could be sisters."

As I drove to work wondering what sexual game my wife was planning for later, every movement I made got me more and more excited. The work day was pretty much normal, I don't think anyone at the office noticed my sexy underware. My wife would call every few hours to tease me. "Hi honey, are you horny today?"

"Yes I am."

"Why"

"Because I am wearing sexy panties, a bra, and stockings"

"I can't hear you, why are you horny?"

"Because I am wearing sexy panties, a bra, and stockings."

"I think it's time for you to change your panties, I am sure they are wet by now. I put an extra pair in the bag with your lunch."

She was right, my panties were wet. I went to the men's room to change then went back to my office.

An hour later my wife would call and suggest that I unbutton the top botton of my shirt. "What do you think your coworkers would say if they saw your wearing a bra?"

I don't know what got into me, but I answered. "That would be hot."

About 15 minutes before I was ready to go home she called again. "Why don't you meet me and Jessica at a cute little boutique clothing store about 10 minutes from your office." She texts me the address and I meet her and Jessica in front of the store. When we walk into the store I meet the owner, Danica. She is a good friend of Jessica, and clearly has been told of my situation.

"This must be Brianna, very nice to meet you."

"Nice to meet you too."

"What are you wearing under your male clothes tonight Brianna."

"Matching bra and panties, plus stockings."

"Very hot, what is your favorite thing to wear?"

"So far I enjoy everything."

"Do you know why you are here tonight?"

"I think I need to find an outfit to wear to our party next weekend."

"That's right. Before you got here your wife and Jessica picked out three outfits for you to try on."

My wife walks with me into one of the dressing rooms in the back of the store. She hands me a red dress. "This is called a cocktail dress. It's a little short, but with your sexy legs I think it will look good on you." She helps me put it on then says. "It looks great on you, lets show Jessica and Danica."

I am very nervous walikng out of the dressing room, and for good reason. There are about 5 customers in the store that can see me, including one man who was buying clothes for his wife. I turned red from embarrassment. All of the customers noticed me, and most of them were smiling or laughing. Back into the dressing room my wife says. "They are laughing because they are jealous. If you had some makeup, a wig, and some heels nobody would know you are a man and you would look 10 times better than them." Then she hands me another dress. "This is a little long and a little low cut." She helps me put it on, then takes a lipstick out of her purse and hands it to me. "Put on some lipstick. later we will get you a purse. A woman should never be without her purse or a lipstick."

I walk out of the dressing room and there seems to be even more customers watching. Jessica and Danica both nod in approval. Danica says. "That's a beautiful dress and it looks great on you. Love the lipstick." It looks like most of the customers also approve, and I go from embarrassed to excited.

One more trip to the dressing room and my wife hands me another short dress. This one is purple and very pretty, and I am actually able to put in on by myself. As I walk out some of the customers actually applaud. A few minutes later the store closes. Danica locks the door and the four of us stay behind and go over the dresses that I tried on. The woman agree we should take all three and decide at a later date which to wear to our party.

Danica says. "You will have a better idea which outfit to wear after we add a few accessories. Brianna still needs a wig and some high heels. Get her nails done and add some jewelry and she will get more attention than us. I think I'm a little jealous.

The cute guy shopping with his wife gave me his number. His name is Bill and he really wants Brianna to call him."

As the four of us leave the store I thank Danica for all her help. She says. "You are very welcome, I love helping people find their feminine side. I know you will make a beautiful woman. Let me know if there is anything else I can do."

"We will." Says my wife.

Danica says."One favor I would like to ask."

"Anything." I say.

"Actually two favors. Call Bill, and invite me to your party so I can see the final transformation."

"Definitely." My wife says. "We will do both."

On the way home my wife talks about how much fun we had at Danica's boutique. "I think when we get home you should call Bill. I think you should jerk off tonight after you talk to him."

I know that if I object to calling him she won't let me cum, and at this point I am so horny I will do just about anything.

We get home, I strip to my panties, bra, and stockking and I freshen my lipstick. My wife dials Bill's number, puts the call on speaker and hands me the phone.

"Hello Bill, this is Brianna, how are you doing?"

"Much better now that you called. You looked so hot tonight my wife and I couldn't stop talking about you."

"What were you saying?"

"Nothing much, just that I would love to smack that sissy ass of yours and then watch you suck my cock."

I couldn't believe how turned on I was getting, then my wife chimed in. "Bill, I am afraid you are getting Brianna too excited. He, I mean she, needs to be cumming soon. What does your wife think about you trying to seduce Brianna?"

"She loves it, she's into all kinds of sex. She thinks you are hot also."

"So is she, but I'm not into women. Anyway, I think I better let Brianna cum before she explodes."

My wife hangs up the phone before I get a chance to say goodbye. She sees the bulge in my panties and says. "Let's try something different tonight. I'm a little horny myself. Why don't we both cum."

Next thing I know she opens her underwear draw and pulls out two 8 inch dildos and says. "One for me and one for you. I want you to jerk off while pretending this dildo is Bill's cock while I watch porn and fuck myself with the other dildo. Do you want to bet on who can cum first?"

"I am not making any more bets."

I start sucking on the dildo pretending it's Bill's cock. My wife is watching porn while sliding the dildo in and out of her pussy. Her loud moans are distracting me, then I look over and see she is watching lesbian porn. Two hot women is sexy lingeries licking each other's pussy. I cum 10 seconds later. My wife's moaning gets louder and her breathing heavier. Less than a minute later she starts to squirt and has the most intense orgasm I've ever seen her have. A minute later she regains her composure, licks her pussy juices off her dildo and says. "Yum."

"I didn't know you were into lesbian porn." I ask.

She just ignores the question. "We still have work to do. Tomorrow you need to practice walking in heels, then we need to make an appointment to get our nails done.

Once again my wife calls Jessica and retells the evening events starting with the phone call with Bill and me sucking on a dildo. She leaves out the part of her masturbating to lesbian porn, but I don't think Jessica cared. The two girls gabbed for another few minutes before my wife said. "Ok, we will meet you tomorrow after Brianna comes home from work."