Kinky Vacation Pt. 02

My wife and I were waiting for a cab to the airport after our week at a tropical island paradise. The previous night my wife had lived out her fantasy of have wild sex with a younger man. To make her fantasy come true she needed to dress me as a woman to find a date for her young man's friend. I may have objected at first, but wearing sexy clothes and makeup and having sex with two men was incredible. But as my wife said, "We are on vacation, what better time to live out our fantasies. We can't do this at home" In other words, what happens on vacation stays on vacation. Or so I thought. So what my wife said next shocked me. "Last night was so much fun I think we should continue this when we get home."

"Yes", I replied, "but I thought it was a one time only, I hate the thought of you having sex with other men."

"But you looked so hot dressed as a woman, and you seemed really into sucking cock and getting fucked. Admit it you loved being a submissive slut."

As usual she was right, but that wasn't the point. Then I said again, a little angrier this time, "I don't want you having sex with other men."

Then my wife said, "You are just upset because you didn't get to cum last night. C'mom loosen up, I'm so excited thinking about last night my pussy is wet. why don't you put your hand up my dress."

Seeing I was angry she said, "I can see you are upset, we can talk about it when we get home."

We barely said a word to each other the first hour of the flight. We were about an hour from landing when my wife got up to stretch her legs and go to the bathroom. When she got back to her seat she whispered in my ear, "I took my panties off, please put your hand on my pussy" Then she tooked my hand put it under her dress and started rubbing her pussy while still whispering in my ear, "See how wet I am, make me cum."

She was incredibly wet and she started moaning as I put two fingers in her pussy. Then she started rubbing my cock as she continued to whisper dirty thoughts, "Your cock is getting hard, I bet you are thinking of those huge cocks we fucked last night"

"Yes" I whispered back, "Last night was unbelievable, I have never seen you so excited."

"I don't know what was hotter, getting fucked by Bill's huge cock, or watching you all dressed up and beautiful getting spanked and begging for cock"

As she whispered more dirty thoughts in my ear I became more and more excited. I moved my fingers in and out of her pussy, while she unzipped my pants and gently stroked my cock. Within seconds I came, squirting my cum on my wife's hand.

Then she said, "lick the cum from my hand."

I licked every drop from her hand as I continued to finger her pussy. Her moans got louder and moments later she came. Then she leaned over and kissed me, "I think that couple in row 8 heard and saw everything. Tell me how much you enjoyed tasting your own cum."

"I loved it, and I love you."

Then she kissed me again and said, "You better go to the bathroom and wash your face. You should also change your underware, put on these panties."

Finally we get home. We unpack from the trip and do a couple of loads of laudry. I see my wife throwing out some of my clothes and rearranging the closet.

"We need to keep a separate drawer in the dresser for you girlie clothes. You certainly don't need your boring underware when you can wear lacy panties. I also made some space in the bathroom for your makeup."

With no food in the house we decided to go out to dinner and then do a quick supermarket run. All thru dinner my wife started making more sexual comments. She would ask me if I thought the waiter was cute, or did I think the man sitting at the next table had a big cock. I could see wear she was going, and I was getting a bit turned on, but I continued to say, "We are not on vacation anymore, I am not happy about you fucking other men."

"Who said anything about me fucking other men, you must have a dirty mind. I was just asking if you thought some guy was cute or if he had a big cock. I will change the subject. Do you think that woman is hot? Do you like her shade of lipstick? I bet she wears that color when she wants to give a blowjob."

Her little game continued thru dinner. It didn't stop in the supermarket. It was embarrassing when she picked up a cucumber and put it under her skirt.

"This is a big one, I think I will bring it home. If I can't have another man's cock tonight at least I can get fucked by a giant cucumber."

When we get home my wife is still horny as hell and she says, "Honey let's ready for bed." I tell her I need to take a quick shower and I will be there in 15 minutes. As I get out of the shower and start drying off I hear moaning from the bedroom.

"Oh Bill, please fuck me. I want your cock so bad." There was my wife dressed in sexy lingerie wearing hot red lipstick alternating between putting the cucumber in her mouth and her pussy.

Seeing her dressed in her hot lingerie gives me an erection. I jump in the bed. We start making out and I start playing with her tits. She stops me and says, "Put on these sexy panties and some lipstick." By now I am so horny I do as she says. I get back into bed and ask, "Where was I?" She answered "Sucking my tits!"

So I go back to sucking her tits and she says, "Look, lipstick marks on my nipples, we must be lesbians. Please lick my pussy Brianna." As I get ready to lick her pussy, my wife starts smacking my ass. By the third or fourth smack she is hurting me and I yell, "OUCH".

"Stop whining, I didn't hear you complain when Bill was smacking your pretty little ass." I immediately apologized and told her to keep smacking my ass. She asked if I really liked it. I don't know what got into me and I said, "Yes, Brianna really loves getting her ass smacked." We proceeded to have amazing sex and we fell asleep in each others arms.

The next day was Sunday, last day before we both had to go back to work. I guess I was a bit stressed because the company I worked for was not doing well and there were rumors of upcoming layoffs. My wife was aware of this and was being very supportive. Sometimes I thought that her crazy sexual fantasies were her just trying to distract me. But I was wrong. That afternoon she brought it up again. "Honey let's talk about this. We had an amazing time on vacation. Clearly you loved wearing women's clothes and sucking cock, and I loved getting fucked by someone 15 years younger than me who just happened to have a big cock. What's your problem?"

"My problem is we were on vacation, had some fun, but never have to see these people again. We know so many people here I don't need friends and neighbors knowing I am wearing panties, or thinking that you may be fucking them."

"Sweetheart, I would never fuck anyone behind your back. Half the fun is knowing you are there and will eat my pussy after a cock cums inside of me. And nobody has to know that you are a sissy slut that loves to get spanked"

"I am still not comfortable with this, can we change the subject."

"OK, by the way I just got pictures of Bill's cock texted to me, do you want to see them? He told me to say hi to Brianna. "

For some strange reason I was getting excited. I looked at the pictures and my wife saw I had an erection.

"See, look how excited you are to see these pictures. I know you want that cock in your mouth as much as I do."

"Like I said, we were on vacation and never have to see them again"

"OK, but I thought it was nice of Bill to send those pictures and ask about you. I have an idea, why don't I buy you a sexy outfit, dress you up as Brianna, and send pictures to Bill."

The thought excited me so I said, "Fine, then will you stop talking about fucking other men?"

"I will stop for a week."

I get to work Monday morning. I still have a job, but for how long nobody knows. Everyone is walking around on eggshells waiting to see if they are getting laid off.

I get home and my wife has a bag that she has put on the bed. She asks me to open it. It was from Victoria Secret, a couple of pairs of panties and matching bras. She asks me to try them on. The panties are easy, but I need help with the bra.

"How do you like them, you look very sexy."

"I like the way they feel, thank you."

This goes on for the next few days. Funny thing is that knowing I have a package of women's clothes waiting for me helps me get thru the stressful days at work, and I find myself getting excited as I drive home. One night I get stockings and a garter belt, one night a couple of sexy dresses. another night assorted makeup, lipsticks, eyeliners, mascara. By Friday night I have everything I need to get dressed and send a picture to Bill. My wife dresses me from head to toe, or should I say 3" heel shoes to a blonde wig. I smile for the camera, she takes a few pictures and texts them to Bill. He responds almost immediately with a smile face. Then my wife says, "I have a little surprise." She has one more bag with a little gift wrapped package inside. "Go ahead, open it." I open the package and it's a 7" dildo. Then she says,"Freshen up your lipstick and then suck on it." I put on lipstick and then start sucking on this dildo, but instead on taking pictures my wife is taking a video." This time Bill sends back a video of him stroking his cock and saying "Wish you were here."

My wife and I were so turned on we had wild sex, complete with spankings and each of us getting fucked with the dildo. My wife said, "That was amazing, what do we do for an encore?" "I am sure you will think of something.", I reply.

The following week the shit hit the fan at work. I along with nearly half of my coworkers are laid off. Two weeks later with no job prospects in sight I start getting depressed. My wife tries to cheer me up by buying me sexy clothes and making up fantasies, but nothing is working. I am getting frustrated with no job offers on the horizon. My wife is getting frustrated because she is not getting laid and she is working extra hours at her job to help us out with the bills.

This goes on for another few weeks and life keeps getting worse. Finally one day my frustrated wife comes home and says, "I have some good news, my boss's secretary is pregnant and she is taking the next few months off."

"How is this good news?" I ask.

"My boss needs a secretary."

Again I ask, "How does this help me?"

"It doesn't help you, it helps Brianna."

"What?"

"It helps Brianna, you can be my boss's new secretary. I already told him about you and the job is yours. You start next week."

"But your boss is a pervert!"

By now my wife seems annoyed, "So he's a pervert. He will squeeze your tits and try and kiss you, but he is basically harmless. I am tired of you sitting at home moping. I am tired of not getting laid. You love wearing women's clothes and makeup, now you can get paid for it"

"Do I have a choice?"

"Not really. We can go shopping for work clothes this weekend, and you will go to work on Monday"

Saturday we go to the mall. Shopping for conservative work clothes is not as much fun as shopping for sexy clothes and my wife senses my lack of enthusiasm.

"Stop moping, let's do this. If you behave we can buy something sexy later."

So we spend the next few hours shopping for work outfits. Then my wife says, "I know what will cheer you up. We can get a manicure and a pedi."

That definitely cheers me up. My wife says, "Do you want to buy something sexy now?"

I shake my head yes and she says, "Then you go shopping on your own. I think it's about time you learned to shop for yourself."

"But you have such better taste than I do."

"You need to learn how to do this, start by going to the makeup store then come out and show me what you bought."

I walk into the makeup store. I am like a kid in a candy shop. So many choices of lipsticks and eyeliners. Mascara and eye shadow. I am getting excited just looking at everything. A half hour later I make my purchase and run out to show my wife what I bought. My wife is impressed, "You did great, love the assorted color lipsticks. Something sexy, something slutty. Now go to Victoria Secret and pick up some sexy lingerie. Don't get too excited, you don't want that bulge in your pants to give it away that you are not a real woman."

That last thought in my head makes me nervous as I walk into Victoria Secret. I am thinking that nobody has suspected I am a man, but maybe I am wrong.

As I wonder around the store a very attractive sales girl walks to me and says, "Hi, my name is Taylor, can I help you with anything?"

"No thank you I say, just looking for a few pairs of panties."

Then she says,"We have a sale on nighties, why don't you follow me so I can show you."

We walk over to the nighties and she says, "Feel how soft they are, they will feel amazing against your skin."

They do feel amazing and I start to get nervous when I say, "I will take one in black and one in pink."

"Nice choice, they will look amazing on you. Is there anything else you need?"

"Not today, thank you for your help."

Taylor thanks me and walks me to the cashier. Then she hands me a piece of paper with a phone number and says, "By the way, my boyfriend loves cute sissy men. Why don't you come over later and show him what you bought. Oh, and bring your wife, I think she is kind of cute."

I don't know what to say, so I quickly pay for the nighties and panties and run out of the store.

My wife asks, "What did you buy?"

I show her, then she says,"You seem a little tense, did you meet Taylor?"

Now I am completely confused.

"Oh, I didn't tell you that my new friend Taylor works at Victoria Secret? I met her a couple of months ago when I bought you panties and bras. We had a wonderful conversation. I told her all about our vacation, she told me all about her boyfriend.

I will call her and say we will come over at 7 tonight. That should give us just enough time to get home and make you all beautiful. You know you want to."

My wife calls Taylor and then tells me, "A slight change in plans, Taylor's boyfriend prefers you come over as a man and then get dressed and changed in to Brianna, doesn't that sound like fun. Taylor also said she knows another young man into sissies. She said he is single and very cute. Maybe you will find yourself a boyfriend and snap out of your funk."

"But I don't want a boyfriend."

"That bulge in you panties says otherwise, let's go home a relax. It's going to be a fun night."

We get home, my wife is getting excited about the evening. I am nervous, but I am getting excited myself.

My wife says, "You should probably put on your makeup at home, you can freshen it up later if necessary. Then I think we should bring over a few outfits for you to wear. You can try on some of the work clothes that we brought today and get everyone's opinion."

"I think that's a great idea. I wonder if Taylor's friends have big cocks"

I can't believe what I am saying, but then I add, "Sorry I have been a bit of an ass lately. Thank you setting this up tonight. You are always right about me, I think this will snap me out of my funk."

"Nothing like a big cock to cheer someone up" She says.

"YES, I hope they have big cocks. And honey, I've been thinking it over. You deserve to to have sex with other men once in awhile. Sorry if I haven't been more understanding."

"That's alright honey, but tonight is all about you."

As we drive to Taylor's my wife suggests we stop at a liquor store to get a bottle of wine. "I remember how horny you got when you had a couple of glasses of wine when we were on vacation. Did I mention my pussy is getting wet just thinking about tonight?"

"No you didn't mention it."

"I wonder if Tayor would be in to licking my pussy?"

We get to Taylor's house. She thanks us for the wine and introduces us to her boyfriend Kyle and his friend Daniel. Everyone seems nice. They compliment me on my makeup and say they are looking forward to my fashion show. After a glass of wine Taylor says, "Let's get the fashion show going."

So me and my wife go into the guest bedroom and she says,"Let's start with this outfit. It's very pretty, but on the conservative side. It's perfect for the office or a casual night out. The pantyhose really make your sexy legs stand out. Try carrying this purse to complete the look."

I walk back to the family room to a whistle and a couple of "very pretty's." As I walk back to try on another outfit Kyle feels my tits and Daniel smacks my ass.

"Time for something sexy?" my wife asks. I don't need to answer she picks out sexy black panties, a garter belt, and stockings. She adds a black bra and says, "Let's complete the look with that nightie you bought from Taylor at Victoria Secret. Wow, what a sexy girl you make, those young men are going to love you."

Before I walk out of the room I add some lipgloss. "Nice touch", my wife adds. "That color will look good on someone's cock."

When we walk back to the room Taylor directs us where to sit, "Brianna, why don't you sit on the couch between these two handsome men while your wife and I sit on this couch enjoy a glass of wine and take some pictures."

There I am sitting between Kyle and Daniel. They both start feeling up my stocking, moving closer and closer to my aroused cock. Kyle says," Brianna, your panties are so wet and your pussy seems to be growing." I can't really speak because Daniel is kissing me, his tongue moving in and out of my mouth. They both start feeling me up under my nightie and I start moaning with delight. I start rubbing both their cocks while they keep feeling my tits.

Taylor chimes in,"you were right, he really is a slut."

My wife agrees,"yes she is, don't forget to smack her ass and make her beg, she loves that"

Next Daniel is smacking my ass and Kyle is making me beg for his cock. I look across the room Taylor is sitting there video taping this while her legs are spread and my wife is licking her pussy. Kyle pulls out his cock, it is much bigger than mine, and he starts smacking me in this face with it. "I didn't tell you to stop begging slut"

"Please let me suck that huge cock. I got all dressed up slutty to suck cock and get fucked. I want to swallow your cum and feel another load on my ass."

Finally I get a cock in my mouth and another in my ass. My wife stops licking pussy so she can watch and shout encouragement.

"Let me see you boys cum, Brianna really wants it." They both cum within seconds, the women applaud, and I collapse on the couch.

Taylor says, "Brianna you are amazing."

"No" I say, "Daniel and Kyle are amazing. I certainly hope we can do this again."

"How about tomorrow?", Taylor asks.

Then my wife answers, "We can't do tomorrow, Brianna needs to relax and get ready for her new job. She's very excited about dressing full time as a woman, and there are a few female things we have to go over."

On the way home my wife complimented me on my feminine skills. "I am so proud of you, and so horny I can't wait til we get home."

We get home, my wife has yet another surprise. Taylor had emailed the video of me having sex with Daniel and Kyle. What a turn on watching myself suck a cock.

"This whole night has been amazing, but I have one question."

"What's that dear?"

"How did Taylor's pussy taste?"

"Shut up and kiss me."

We kissed, had amazing sex, and passed out.

The next morning when I woke I noticed that my wife and I were wearing matching nighties which I thought was pretty hot. I asked my wife if we could watch the video again.

"Sure we can, after you call Taylor and thank her for last night."

I pick up the phone and call, "Hi Taylor, this is Brianna. I just wanted to thank you for a wonderful evening."

"You are very welcome. Kyle and Daniel can't stop talking about you. They want to know when they can see you again"