Weekend Getaway Surprise Ch. 02

Thanks for the positive feedback and the encouragement to write part 2.

In part one. my wife had planned a little anniversary getaway. Unknown to me she had discovered sissy porn on my computer, and found some lipsticks in my night table. She decided to pack my suitcase with only women's clothes, dress me up and pick up a couple of guys.

Part 2. The next morning.

I didn't know what to expect as I woke up Saturday morning. My wife woke up with a big smile on her face. "Wasn't last night wonderful? After I found your lipstick stash I thought you would like dressing in sexy lingerie, but I never suspected you would actually suck a cock. I wonder what those boys would think if they knew you were a guy?"

I said, "Last night was kind of wild, but I think it was a one night only experience. I would like my male clothes back."

"Please don't say that. Let's give it another day at least, I bought you so many sexy things. You have so much more to experience. Wait til you feel panties and stockings after you have your legs and your balls waxed. Look, you are getting hard just hearing me talk about it."

"I don't know."

"How about we get dressed up. The hotel has a great spa, I booked us a massage and a manicure/pedicure. I promise you will love it."

I finally agree and my wife gives me a hug and a big kiss, "We are going to have so much fun."

My wife lays out the clothes for me to wear. Matching pink panties and bra, a pink sundress. I still need help with my eye makeup, but with my wife's encouragement I put on a pretty pink lipstick by myself.

"You do make a pretty girl", she says as she hands me my blonde wig. "I have a serious question, which did you like better last night? Wearing sexy lingerie, wearing lipstick, sucking a cock,or watching me get fucked by some young stud?"

"It was all pretty hot. I always fantasized about dressing up, but I never thought about sucking cock."

"Why didn't you tell me that you loved wearing lipstick?"

"I guess I was embarrassed. I didn't know what you would think."

"No need to be embarrassed, I think it is so hot. I love to wear lipstick, it makes me feel sexy. Think of the fun we can have going makeup shopping together."

"I guess so."

"Ok, let's go downstairs to the salon."

I follow my wife as she walks into the salon and hear her tell the receptionist,"I am here for the 11 o'clock manicure/pedicure for me and my husband."

"Yes" the receptionist says,"have a seat at chair #5 and 6 the manicurists will be with you shortly."

I question my wife, "Why did you tell them I was a man, now I am embarrassed?"

"Don't be embarrassed, what happens in the nail salon stays in the nail salon, I was just having some fun."

We sit at our chairs and two attractive manicurists come over. They put our feet in some warm water and soak our hands. It feels very relaxing. One of the girls winks at my wife and says,"Which one of you is the husband?" My wife smiles and points to me. The manicurist keeps the game going "We get plenty of lesbian couples here."

"Don't be embarrassed" my wife says "The girls are just having fun with us. Relax and enjoy getting our nails done."

It felt good having the manicurist fussing over my nails while she was massaging my feet, but I was not sure how I felt about my wife and the women discussing my crossdressing. The women seemed fascinated as my wife described last night's adventure.

"How did you know you could get him to dress up?" Her manicurist asked.

"Once I found his lipstick collection I started doing research on crossdressing and sissification. After I saw the porn on his internet I started to plan this weekend. I knew he would enjoy dressing up, but I didn't realize how easy it would be to get him to suck cock."

The conversation continued as if I weren't there. "How do I get my boyfriend to dress up?" one of the manicurists asks.

My wife answers,"You are smokin hot, you could probably get him to do whatever you want."

The other woman asks,"My husband has a really nice cock, but I am not into blowjobs. Do you think your husband would suck his cock?"

Finally I say, "Hello! Do I get a chance to talk here?"

The manicurist answers, "Sorry, do you like your pretty pink nails, it matches your wife's."

"It's very pretty." I answer.

"It matches your lipstick. Would you like to suck my boyfriend's cock?"

My wife chimes in, "I think we are embarrassing my husband, let's continue this conversation after our massages. He should be more relaxed."

The girls lead us to another room with two massage tables. I have never been a big fan of massages from strangers. I hate the feeling of oils on my body. My wife loves massages and has arranged for my massage to be oil free. We wait about 15 minutes before our masseuses come into the room. They are both tall with very athletic bodies. They apologize for being late and order us to strip to our bra and panties. I get undressed and lie down on the table, as does my wife.

My masseuse starts working on my back and neck. "Your are very tight" he says.

"I've had a lot on my mind lately."

"So I've been told, I've never massaged a man wearing a bra and panties before. I am here to help relieve your stress."

He continues his massage. His hands get lower and lower. Soon he is massaging my ass. I wonder if he can tell I have a bulge in my panties. I turn my head and watch my wife. She is very much enjoying herself. I notice her masseuse is also moving his hands lower until he reaches her ass. As he rubs harder my wife starts moaning. The moaning gets louder as he places a finger in her pussy.

"Do you like seeing another man fingering my pussy?" she asks me. "I don't even know his name, but I think want him to fuck me. Look, you have a hard on, are you enjoying watching my pussy get wet, or has your masseuse made you excited? Why don't you freshen up your lipstick. Maybe your masseuse will stick a finger in your ass while you watch me getting fucked."

I do as she says and I reapply my lipstick. Next thing I know my wife is on her back and both masseuses are sucking on her breasts while one continues to finger her pussy. Soon she has one cock in her mouth and one in her pussy. Her moaning gets louder and soon she cums. Minutes later both men cum, one on her tits and one in her pussy. I start rubbing my cock thru my panties when my wife stops me,"You can't play with yourself until after you have licked up these two loads of cum."

I lick the cum from her as the two masseuses look on and laugh.

"Did you liike watching your wife have sex with two men?" Asks one of the masseuses.

"Yes." I answer.

My wife replies, "Make sure you thank them and give them a good tip."

"Thank you for fucking my wife and making her cum."

"You are very welcome. By the way, you make a very pretty sissy. I wish we had more time, but you need to get dressed so we can get the room ready for our next appointments. Maybe next time you can suck our cocks."

My wife gives both of the men a big kiss. As we get dressed she says to me,"You are going to love our next appointment. We are going to get a leg and bikini wax. You will really love the way your clothes are going to feel once you lose that unsitely hair. When men feel your hairless stocking legs you will go wild."

Without going into details, I didn't enjoy having nearly all my body hair removed. But my wife was right about how it felt putting my clothes back on. The silky panties felt amazing, and I almost came when my wife started to rub them over what she called my boy pussy. The bra felt so much sexier now that I didn't have chest hairs, and I was looking forward to putting on stockings.

My wife says, "You look such much sexier without all that hair. We have one more appointment. We are going to get facials, then we are going to have a professional makeup artist make you even more beautiful."

"How long have you been planning this weekend?" I asked.

"About a month or so. Ever since I found your lipsticks and sissy porn I have been thinking of something to spice up our marraige. I talked it over with my friends Lacey and Erin and we planned this weekend."

"You did what? Who else did you tell?"

"Just Lacey and Erin. They are coming to the hotel later. They can't wait to meet Brianna. Now let's go get our facials."

The facial experience was much like the manicure. My wife and two women gabbing away, poking fun at me while telling my wife how lucky she is to be married to a crossdresser. 'You can go shopping together, try on each other's clothes, pick up guys. I wish my boyfriend would be into it."

After the facial the makeup expert comes in. First she washes my face and then massages in some lotions. She trims and colors my eyebrows. Some blush, eye makeup, more lotions, lipstick, lipgloss. Then she orders me to look into the mirror.

My jaw drops. I can't believe how much I look like a woman.

My wife says,"Wow you look gorgeous, I almost didn't recognize you. I wanted to take you shopping, but it's getting a little late. Let's go back to our room and relax. My friends will be here in a couple of hours."

I agree. We get back to the room and I say,"I know what you are going to say."

"What?"

"You are going to ask me what my favorite part of today was."

"You are so smart. So what was your favorite part?"

Then I say, "Why don't you tell me your favorite part first, and then I'll tell you mine."

"That's easy", she says. "I loved my massage. I couldn't believe how wet I got when the masseuse worked his hands down to my ass and then put his finger in my pussy. I can't believe he did it with you just a few feet away. I think that made it even hotter. Ok, what was your favorite part?"

"Watching you have sex with two men was pretty hot, so was licking up their cum. I guess I just like the entire experience of feeling feminine and the feeling of the sexy panties and bra on my hairless body."

We spend the next hour relaxing, then my wife lays out my clothes for the evening.

"I hope you like this outfit, I think it is very sexy."

I put on matching lacy black panties and bra. My wife hands me a pair of black thigh stockings. They feel even better than I imagined. Then she hands me a red mini skirt. I try it on and she says,"You are so pretty."

Just as she finishes the sentence there is a knock on the door. My wife says,"answer the door." I answer the door, it's Lacey and Erin.

Erin says, "Sorry, I think we have the wrong room."

My wife says, "You have the right room, say hello to my husband Brianna."

For as long as I've known these women this is the first time I have ever seen them speechless.

Then my wife says,"I guess I win our bet."

"What bet?" I ask.

"I bet Erin and Lacey that we could transform you into a pretty woman."

"What did you win?"

"Erin and Lacey have to lick my pussy."

Lacey says, "You won fair and square, I can't believe your husbnd can pass as a woman."

"Yes." My wife says, "He has even sucked cock, but I think he needs more practice. He also needs more practice walking in heels and doing his, I mean her, eye makeup, but we have plenty of time to work on those skills."

"Is she still a virgin?" Lacey asks.

"Yes, but with any luck that may change tonight."

"I may be ok with dressing up and giving a blowjob to some guy who thinks I'm a woman, but I don't want a cock up my ass."

"You will love it." The girls all say.

"I don't think so."

Erin adds,"Maybe if we all get fucked in the ass tonight it will make you feel more comfortable."

Then my wife says,"Don't worry girls, after Brianna watches you lick my pussy and then pick up a couple of guys she will be so horny she will do anything we say. You should have seen the bulge in his panties when the two masseuses fucked me."

Erin says, "Wow, when did you become such the slut?"

"I couldn't help myself, his hands started rubbing my ass and then he slipped a finger in my dripping wet pussy right in front of my husband. I've never been so turned on."

Lacey says, "Look how excited she is getting, I think it's time to pay off our bet."

Erin and Lacey take off my wife's clothes and take turns licking her pussy. My wife is loving it, starts shaking, and cums within minutes. I start rubbing my cock thru my panties and I cum within seconds of my wife.

The my wife angrily says,"Nobody gave you permission to cum. Take those panties off now!!"

I take my panties off and my wife shoves them in my mouth. Then she takes me over her knee and starts spanking my ass. "You dirty little sissy. How dare you embarrass me in front of my friends and cum without permission."

"I'm sorry", I cry, "Please stop spanking me."

She stops, then says "I will talk to my friends and think of an appropriate punishment."

The women make me leave the room, "Come back in an hour while we decide what to do with you. Don't even try to pick up some guy, if you do you will get another spanking. If anyone tries to hit on you simply tell them you are waiting for your wife."

I sit in the bar. Three separate men offer to buy me a drink, but I simply say I am waiting for my wife. Finally I get a text to come upstairs.

When I get upstairs my wife asks if anyone tried to hit on me.

"Were they handsome?" She asks.

"I guess so."

"Here's what we decided your punishment will be. First, when you are home we will lock your cock in a chastity cage. No more jerking off for you. Second, when we all go out later the three of us will pick up hot guys and then we will find the grossest man in the bar and bring him back to the room to take your virginity."

"That sounds disgusting, what if I say no?"

"Then you will never be allowed to dress up again. I will throw away your female clothes and all your lipsticks."

I have no choice but to agree.

Erin says,"We saw a sleazy biker bar about 15 minutes away, we can take Brianna there."

"Sounds like a plan. Should we dress Brianna sexy or slutty?"

"She is dressed sexy now, let's see what slutty looks like."

My wife says, "I have the perfect outfit." And she starts handing me clothes. Matching lacy panties and bra and a very short black minidress. She does my eye makeup.

Lacey says,"That isn't so slutty."

"We are not done yet" my wife says, "Brianna, go put on your red lipstick."

Lacey replies,"Now we are talking, cock sucking red lipstick. I love it."

'One more thing. Nothing says fuck me more than fishnet stockings"

"Wow." says Erin, "I need to take Brianna's picture."

Me, my wife, Lacey, and Erin get lots of looks and whistles as we walk thru the hotel lobby to Erin's car. Fifteen minutes we arrive at a very sleazy bikers bar. It doesn't take long before men start hitting on us. Erin and Lacey pick up two men right away and start making out with them. Two good looking younger men come over to our table and start talking to us. My wife asks how old they are.

"Twenty one."

My wife then says,"My friend loves younger men. Buy her a drink and she will give you both blowjobs." Less than a minute later they come back with drinks in their hands and sit next to us at our table. After a few minutes of small talk my wife tells me, "Get under the table and suck these young men's cocks."

I crawl under the table. The two men already have their pants down and cocks out. I am not very comfortable, but I manage to suck on one cock while I give the other a hand job. Then I switch cocks. I do this for about ten minutes before the first cock cums in my mouth. I put the other cock in my mouth and he cums seconds later.

The young men pull up their pants, thank me, and walk away with smiles on their faces.

I sit back at the table next to my wife. Finally Erin and Lacey return. My wife says,"Look at you three sluts with messed up lipstick, what am I doing wrong?"

Lacey says,"We found someone gross who we think Brianna should fuck. He's the overweight guy at the end of the bar."

I look toward the end of the bar and see someone about 5'10" maybe 300 pounds with a really gross bushy beard.

My wife says,"Perfect. Brianna, go over and ask that nice gentleman to please fuck you. Don't be shy, we will all go with you. But first you three girls should probably fix your lipstick."

We go to the ladies room and fix our lipstick, then we all walk over to the bar. I go over to the man and offer to buy him a drink. I introduce myself as well as my wife, Erin, and Lacey. He thanks me for the drink and introduces himself as Tom, but his friends call him Tiny.

I say,"Tiny, would you please fuck me?" He does a double take and I ask,"Tiny, do you think I'm pretty, would you please fuck me."

"I think you are hot. I would love to fuck you. How about right now in the back of my pick up truck?"

Tiny holds my hand as we walk to the pickup truck. My wife and friends are not far behind us. We get to his pick up truck and Tiny starts kissing me. Then he lays a blanket into the bed of the truck and lifts me up and places me in the truck. We continue to make out while he starts feeling me up. It feels gross and exciting at the same time. I unzip his pants and pull out his cock. Tiny is not tiny. Next he lays me down on the blanket and he gets on top of me. A 300 pound man on top of me reaching under me dress and pulling down my panties. At some point his hand brushes against my balls and then he touches my erect cock. He gives me a look like he is going to kill me, but instead he just says,"I love sissy boys, prepare to be fucked." But before he fucks me he says,"this is what you get for trying to fool me."

He smacks my ass harder than it's ever been smacked before.

"Ouch, that hurts." Then he smacks me again and says," complain again and you'll really be in trouble." Then he pulls my panties off, turns me over and says,"Stick that sissy ass up in the air"

I do as I am told. Tiny sticks his cock in my ass and starts pumping away, each thrust harder and faster than the one before. I start moaning and Tiny yells,"Tell me how much you love my cock in your ass."

"I love it, fuck me harder."

"Louder", he says.

"I LOVE IT, FUCK ME HARDER."

He keeps fucking me until he pulls his cock out of my ass then says to my wife, Erin, and Lacey "Are you enjoying the show?"

My wife answers, "Hell yes, my pussy is so wet."

Then Tiny grabs me by my neck and starts slapping me with his cock. "Suck it." He says.

I starts sucking his cock. He shoves it down my throat and cums. Then he slaps me again and says, "Get your sissy ass out of my truck."

I climb out of his truck to the waiting arms of my wife.

"Congratulations, you are no longer a virgin. You are a mess, let's get you back to the hotel and get you cleaned up."

As we head back to Erin's car Lacey says, "Looks like Brianna is having a little trouble walking."

Everyone has a big laugh.

To be continued?