The Bet Pt. 03

In part 1 I lost a sucker bet to my wife. The consequence was I had to dress as a woman for a party we were having at our house.

In part 2, my wife continues to feminize me, but to my surprise I enjoy dressing in sexy lingerie, wearing makeup, and being transformed into an attractive woman.

Although I am no longer having sex with my wife, every night she allows me to cum while discussing one fantasy or another.

The day before the party we completed the feminization. My wife took me to a spa for a waxing while she got a massage. That night she allowed me to lick her pussy. Afterwards she told me how her hot masseuse had fucked her and filled her pussy with cum. Rather than getting angry I found myself getting excited and cumming almost instantly.

As we got ready for bed I asked my wife about our party. "I know I lost the bet, but I really don't want all our friends to know I am dressed as a woman. Can I just be myself tomorrow?"

"You are right, you did lose the bet. But I could tell you really loved the past few weeks becoming Brianna. You will get dressed for the party, we'll tell everyone that you had to go back to your home town to take care of a family emergency and we will introduce you as my sister."

"What will I do if some guy tried hitting on me?"

"Don't worry honey, I will be by your side all night. I think there will be lots of guys who will want to fuck you, and to be honest I think you would enjoy it."

"I'm not gay."

"I know you're not, but I did notice on your computer history you enjoy watching sissy porn."

I was totally embarrassed and didn't know what to say. Then my wife added. "Don't be embarrassed, I thought those videos were pretty hot. I was going to ask you if you wanted to dress, but when I won the bet I thought forcing you to dress like a woman was a better idea. I must admit I didn't think you would make such a hot looking woman. I think more guys will hit on you then will hit on me."

"Don't be silly, you are way hotter than I am."

"You say the nicest things, that's way I love you. Let's get some sleep. Tomorrow will be a busy day."

I tossed and turned for awhile, but eventually fell asleep.

The next morning we had breakfast and I did some last minute cleaning.

Finally my wife laid out my clothes. Matching black bra and panties, sexy stockings. A very short beautiful red dress. I flawlessly put on my makeup, completed the look with hot red lipstick and a blonde wig. Moments later my wife walked in the room to check my out. She was dressed in an incredibly sexy outfit, complete with a garter belt and hot thigh high stockings.

Then she said." Brianna, you look great. Then she put a pretty neclace on me and added a bracelet on my wrist. She handed me a little purse and said. "Take this. Always keep a extra lipstick in there. You never know when you need to freshen up those sexy lips."

A few hours later our guests started to arrive. First was my wife's friend Jessica and her husband Michael. Jessica gave my wife a hug and whispered in her ear how hot she looked. A few couples came in that I didn't recognize, mostly my wife's friends and their husbands. Then Lacey, the woman from Victoria secret. Melissa, the woman from the spa who licked my wife's pussy, and her boyfriend whose cock she bragged about. Danica and Bill from the boutique. And finally my boss. He gave my wife a hug, patted her on the butt and thanked her for inviting him. A few of the guests ask where I was. My wife explained the family emergency. She introduced me as her sister. I must admit I was getting a bit turned on from all the compliments.

At one point my wife said to me. "All the guys think you are so hot."

Everyone was having a good time. Plenty of eating and drinking. I noticed my boss was spending a lot of time with my wife. Moments later she came up to me and said. "Your boss wants to fuck me. He said he would give you a 50% raise."

"What did you tell him?"

"I told him I would fuck him only if my sister can watch. What do you say? Please!"

I didn't know what to say, but she interrupted me and said. "That bulge in your panties gives you away. Freshen up your lipstick and meet me in our bedroom in 5 minutes."

A few minutes later I walk into the bedroom and see my wife and boss making out. He has her hand on her breasts and she is rubbing the bulge in his pants. He starts feeling under her dress and says. "Wow, your panties are so wet, I bet that husband of yours doesn't get you this excited."

As she pulls his pants down she says. "He certainly doesn't have a cock that big. Brianna have you ever seen a cock this big."

I was stunned, but managed to say. "No, that's the biggest cock I have ever seen."

"Why don't you get closer and watch me suck it."

I walked closer to the bed as my wife got on her knees and started sucking my boss's cock.

I think my panties were as wet as my wife's as I watched her giving a blow job which I thought she never liked to do.

Finally my wife stops sucking cock and begs my boss. "Please fuck me. I need that giant cock inside my pussy."

He picks her up, throws her on the bed and starts fucking her. Within seconds my wife is moaning. Her moans get louder and louder and screams fuck me harder, I am going to cum. Moments later she cums harder than I've ever made her cum.

"Keep fucking me, I want you to cum in my pussy."

He keeps fucking her and finally screams, "I'm cumming."

"Wow." My wife says. "That was amazing, how would you like to watch my sister lick your cum out of my pussy."

"Brianna come over and lick my pussy, I know you want to know what his cum tastes like."

I crawl over and stick my tongue in my wife's pussy. I can actually taste my boss's cum. I am so turned on, but my wife whispers. "You better not cum."

After I lick all the cum from her pussy my wife and boss get dressed.

My wife says. "Better get back to the party."

My boss says. "You know I can send your husband out of town every month for a few days. I know you want me to fuck you again."

"That would be great, I definitely want more of that cock. I better freshen up before I get back to my party."

We get back to the party. Jessica finds us and asks my wife how it was fucking my boss.

My wife answered. "He had an amazing cock, and after he came Brianna licked his cum from my pussy."

"That's great." Answered Jessica. "Speaking of Brianna, Michael really wants to have sex with her. He said he would do anything if we can set them up. I was thinking maybe I could convince him to crossdress. I may be wrong, but that bulge in Brianna's panties tells me she would be into it."

My wife agrees. "Ask Michael to put on a pair of panties, tell him that it's the wrong time of the month to fuck, but Brianna thinks he is hot and would love to give him a blowjob."

Finally I get to talk. "Don't I get a say here?"

"You are right honey, Why don't you just hang out with Michael for awhile and see where things go. Me and Jessica will be with you the whole time if you don't want to go thru with it, but I think if you are with a guy wearing panties it would be so hot."

Jessica finds her husband and the two of them disappear for a few minutes. When they reappear Jessica smiles and tells my wife. "He's wearing panties."

The four of us are sitting on the couch and Michael immediately starts flirting with me. I am getting incredibly turned on as his hand starts feeling my stockinged legs.

My wife suggests the four of us move to the bedroom. Michael and I are sitting on the bed. He is still feeling me up. I unbutton his pants and pretend to be surprised when I say. "Are you wearing panties?"

Michael is clearly embarrassed, but I ease his tension by adding. "I think that's so hot. Look at that big cock trying to escape. Can I touch it?"

Jessica interupts for a second. "You know what would be even hotter? If Michael puts on lipstick and him and Brianna make out."

Michael is clearly under Jessica's spell. She puts hot red lipstick on him and we start making out. Kissing a guy wearing lipstick is so hot. As our tongues meet I am getting hornier and hornier. I reach for his cock, get on my knees and try and remember how my wife sucked my boss's cock. I licked the precum from the tip and run my tongue up and down the shaft. Finally I put his cock in my mouth. I must be doing something right, Michael's breathing gets faster and his moaning louder. I start sucking faster and faster almost gagging. A few minutes later Michael came in my mouth and instinctively I swallow nearly every drop. As Michael pulls his cock out of my mouth I look over at my wife and Jessica. They both have their phones out. They have been taking pictures the entire time, and they both have big smiles on their faces.

"Well done." My wife says. "Michael, how was that blowjob from my sister?"

"She is amazing."

Jessica adds." Remember our deal Michael, you promised to dress as a woman if I got Brianna to suck your cock. I think I will call you Michelle. Do you like that name?"

"Yes dear, are you really going to make me do this?"

I add my two cents. "I think you will love dressing up. You will look so hot."

My wife says. "Maybe Michelle and Brianna can have a lesbian affair."

Jessica replies. "That's great idea. Come Michelle, I think we should go home now. We have a lot of work to do. I am so horny, if I stay here any longer I might fuck one of the guests. I think you will be horny again soon. Maybe you will get lucky again later."

Michael kisses me and my wife goodbye. As they leave many of our other guests start heading home. Soon there are only about a half dozen guests left. I am getting a little nervous and suspicious. Most, if not all, remaining guests know that I am not a woman.

I ask my wife what is going on. All she says. "Do you trust me?"

"Yes?"

"Well the last couple of weeks have been so amazing. I not only have a husband, but I also have a best friend in Brianna. I have never been so happy."

"I am happy too, these few weeks have been great."

"Well." She said. "You know every night we talk about a fantasy and you get to cum. Tonight your fantasies will come true, and with any luck we will both get to cum."

Next my wife addresses the remaining party guests. "I want to thank everyone for coming tonight. Many of you have played a part in the feminization of my husband. Brianna would not be here tonight without your help. Tonight Brianna gave her first blowjob. And with all your help we can help her live out the rest of her fantasies. Who would like to go first?"

Billy is the first to raise his hand.

My wife introduces him to the group. "This is Billy. He and his wife were at Danica's boutique the night we were picking out clothes for Brianna, and he took quite a liking to her. That night Brianna and Billy spoke on the phone. Whatever he said got Brianna quite excited and she masturbated moments later. What was that fantasy Billy?

"I said I want to spank his sissy ass."

Billy grabbed me, put me over his knee, and started spanking my ass while our guests applauded and shouted encouragement.

My wife chimed in and added to the embarrassment. "Nice job Billy. Looks like Brianna is getting excited. Check out that bulge in her panties."

As the party continued my wife and I mingled with the remaining guests. I couldn't sit because my ass was sore, but there were plenty of guests willing to rub it and make me feel better.

I see my wife talking to Melissa. She was the woman from the spa who waxed my body hair and licked my wife's pussy. She also bragged about her boyfriend's cock and how much she loved getting fucked in the ass. She and my wife were both smiling as they walked over to me.

Melissa said. "Thank you for inviting us to your party. I have convinced your wife to return the favor and lick my pussy, but she said she would only do it if my boyfriend fucked her in this ass."

My wife added. "Melissa kept telling me how big her boyfriend's cock is. I am so horny. Most of our guests have left. How about me, you, Melissa, and Thomas finishing the night off with a foursome?"

Before I could answer, my wife took my hand and the four of us walked to the bedroom. Immediately the two women take their clothes off.

Then my wife comes up with an idea. "Since this whole experience began with a bet, let's end the evening with a bet. I will lick Melissa's pussy while Thomas fucks my ass. I want you to bet on who will cum first. If you win you get to pick our next sexual adventure. If you lose I get to choose."

I said. "Melissa will come first. I don't think you will enjoy getting fucked in the ass."

Thomas said."I think you are wrong my friend, but to give you a fair chance I will give the girls a one minute head start."

Melissa lies down on the bed and spreads her legs as my wife puts on lipstick. Then my wife gets on the bed and the two of them start making out. As my wife's mouth moves down to Melissa's pussy Thomas looks at his watch. Exactly one minute later he gets undressed. Wow, his cock is huge. As my wife licks Melissa's pussy, Thomas starts rubbing my wife's breast. Then he puts his cock in her ass. Instantly my wife starts screaming. "Oh my God, your cock is amazing. Fuck me harder, I am going to cum. Seconds later she starts shaking and cums."

For a moment I thought she was going to pass out, but Melissa snaps her back to reality. "You're not finished here. I want to cum."

"Sorry, let me just catch my breath and then I will make you cum."

A minute later my wife once again starts eating Melissa's pussy. With Thomas whispering encouragement in her ear Melissa cums.

"Well honey, looks like you lost another bet."

My wife, Melissa, and Thomas huddle to decide my sexual fate, then my wife says. "I noticed you couldn't help stare at Thomas's huge cock. Believe me, having his cock fuck my ass was totally amazing. I want you to take off your panties, put on the slutty red lipstick and ask Thomas to fuck you."

So I take off my panties, fix my makeup and come back to the bedroom.

My wife is on the bed sucking Thomas's cock. "I am warming him up for you, you will thank me later. Don't you have something to ask Thomas?"

"Thomas, will you please fuck me."

"I love to fuck a virgin sissy ass, lie down on the bed."

My wife and Melissa take out their cell phones and start taking pictures. Clearly I am scared, but my wife says. "Don't be nervous I promise you will love this."

I bend over as told and Thomas gently slides his cock into my ass. It hurts a little at first, but as he fucks me harder and faster I am getting so turned on. I can't believe it, I am begging him to fuck me harder. After a few minutes he shoots a big load of cum up my ass. I am so excited that I cum seconds later and collapse on the bed. I

Ilook up at my wife and she smiles. "What do you want to bet on next?"