Weekend Getaway Surprise

I am a mid 30's married man, my wife is in her late 20's. We were about to celebrate our 5th wedding anniversary. My wife suggested we celebrate by going away for a 3 day weekend. She loved planning little trips like these and she found a nice hotel in some artsy town about a 3-4 hour drive from our home.

I was really busy at work that week and had to stay late on Thursday night and go into the office and work a few hours on Friday. My wife said, "Don't worry honey, I know you are really busy. I will pack everything then pick you up from work and drive to the hotel. We should definitely be there by dinner time Friday night."

I thought that was a great idea, and I thanked her for planning this little anniversary trip. A little getaway was just what we needed. I had been so busy and stressed at work for the past month I didn't have the time or the energy to have sex. I suggested to her, "Why don't you pack that sexy lingerie I bought for you on Valentine's Day, we have some romantic evenings to catch up on."

'Yes we do, And yes I packed some sexy lingerie. I can hardly wait to show you what else I bought."

Friday finally comes. My wife picks me up from work. We make excellant time on the drive and we get to the hotel about 5:30. I decide to take a shower before we go out to dinner while my wife makes reservations. As I take a shower I am very relaxed and at the same time I am getting excited for this romantic weekend.

When I get out of the shower my wife says, "How was the shower, your clothes are in the suitcase."

The suitcase is on the bed. When I open it I find only woman's clothes.

"Where are my clothes?" I ask.

"These are your clothes this weekend dear." I noticed you have been watching some crossdressing sissy porn lately, and I thought you might like dressing up. Look what I brought you, sexy panties, stockings, make up. Do you like??"

I didn't know what to say. How could I have been so stupid to not delete the porn I had been watching?

Then my wife added, "After I watched those videos I found your secret stash of lipsticks hidden in the night table next to the bed."

All I could think of saying was, "Sorry dear."

"Sorry you like to wear lipstick, or sorry you got caught?"

"Both??" I said.

Then she said, "You don't have to be sorry, I love wearing lipstick. I love the idea of knowing that men got excited when they see me with hot lipstick on. It makes me kind of horny when I put on my slutty red lipstick and I think about all those men who want me to suck their cocks. Is that how you feel when you put on your red lipstick? Do you want to suck a cock?"

"NO, I'm not gay. I just find lipstick a turn on, especially when you wear it."

"I didn't say you were gay. A sissy maybe, but I didn't say you were gay. And how do you know that you won't like to suck a cock? That lipstick says otherwise. Why don't you put some on for me."

I said, "I will put some on if you do."

So we both put on red lipstick, and then my wife kisses me. "Pretty hot" she says,"You do look kind of cute wearing that lipstick, I bet you would make a very pretty girl. Why don't you get dressed so we can go get some dinner. I'm getting kind of horny, I mean hungry."

I answered, "I'm a little hungry myself, where are the clothes I wore when we got here?"

"I threw them out while you were in the shower. Put on those sexy clothes I bought for you. Your are already wearing lipstick, you watch sissy videos, you will love wearing panties and stockings."

"Are you crazy, I can't go out dressed like this."

"Sure you can, besides you can't just sit in our room all weekend. I came here to have some fun."

"I am not going out dressed in women's clothes!!"

Then my wife says, "OK, let's compromise. I will go downstairs to the bar for a drink while you stay here and get dressed. Then I will come back to the room. If you don't enjoy wearing these clothes I will get you some men's clothes for the rest of the weekend."

"This is crazy.", I said, but Iagreed.

My wife lays out clothes on the bed. Sexy panties, a matching bra, pantyhose, a sexy short black cocktail dress. and a blonde wig.

Then she says "Watch me get dressed, pay attention and learn." She puts on the same clothes that she has laid out for me. I watch as she puts on lacy panties and matching bra. I start to get a little horny when she puts on pantyhose. A short sexy dress completes the outfit. She freshens up her lipstick, then says " Eye makeup is a little tricky,so when I come back I will help you. You have such pretty blue eyes, I can't wait to make them feminine and beautiful."

She looks so hot. As she leaves she says " Ok, I will go downstairs, I'll call you in about a half hour to see if you are ready."

I get dressed. I have a little trouble with the bra and the pantyhose, but I manage. I look in the mirror, I make a pretty good looking woman, and I am excited being dressed. I was hoping my wife would have been back by now, it's been about an hour.

Finally she calls and sounds like she may have had more than one drink. "Hi honey, are you dressed?"

"Yes, where are you?"

"At the bar,I got a little distracted, I will be upstairs in a minute. Don't the stockings feel amazing?"

"Yes they do."

"I told you so, they will feel more amazing after we shave your legs. Now freshen up that hot lipstick, I will be upstairs in a minute with a big surprise."

Two minutes later the door opens and my wife is standing there with some guy.

"Honey, this is Donald. I met him at the bar. Isn't he handsome? When I told him that my husband was upstairs getting dressed in sexy woman's clothes he said he just had to meet you."

Totally embarrased, I said hello and went to shake his hand, but instead he grabbed me and gave me a big kiss. He was bigger and stronger than I was. I couldn't fight him off, so when the kiss became a little more passionate I opened my mouth and let his tongue meet mine. I couldn't believe I was enjoying this.

Then my wife said, "Slow down boys, I need to finish my husband's makeup."

So she takes me over to the mirror and starts making up my eyes. Eyeliner, mascara, and some eye shadow to complete the look. Instead of asking me what I think she says,"Donald, how do you like it?"

Donald gives the thumbs up, then my wife tells me, "You better freshen up your lipstick after that make out session. Go look in the bathroom mirror while Donald and I think of a name for you."

I freshen up my lipstick and come back to the room.

"Very pretty, we were having trouble picking a name. Donald wanted something plain, but I want something more sissy and slutty. We decided on Brianna. Do you like that?"

"I guess so." I said, not really knowing what was going on.

"Donald has a big surprise for you. I checked it out downstairs and I just know it's something you will love. Go ahead Donald, show Brianna what you have for her."

With my wife's prompting, Donald unzips his pants and pulls out an enormous cock.

"Isn't that wonderful honey", she says.

I say, "It certainly is huge."

Then Donald says, "Go ahead Brianna, come over here and touch it."

I touch it and play with it a little, but I freeze when he says, "Now suck on it."

My wife chimes in, "Sorry Donald, I don't think Brianna has ever sucked a cock before. Let me show her how it is done."

Next thing you know my wife is licking the tip of Donald's cock, running her tongue up and down the shaft. She calls me over to get a better view.

"I think Donald's cock is too big to fuck your virgin ass, but I can tell by the bulge in your panties that you are loving this. What excites you more, watching your hot wife giving a blow job, or the thought of having that big cock in your mouth?"

I honestly didn't know, but moments later she took Donald's cock and placed it by my mouth, all the time giving me intructions. After licking and stroking I finally had his cock in my mouth. My wife was holding the back of my head, moving it up and down, all the time encouraging me. Finally she took Donald's cock out of my mouth and yelled,"Brianna, beg him to cum on your face!"

"Please cum on my face, please,please."

Just then Donald moans and shoots a load of cum all over my face. My wife yells, "lick the cum off your lips and taste it." I did, then she said, "The first time I tasted cum I was hooked for life, hopefully you will be too. Make sure you thank Donald."

I thank Donald, then he says, "You are very welcome." As he zips up his pants and gets ready to leave he says to my wife, "There is some kind of convention here this weekend, lots of men from out of town looking for a good time. I think you and Brianna should go downstairs."

After Donald leaves my wife sits next to me, holds my hand, and gives me a big kiss. "Wasn't that hot? You were amazing, I love you so much. I think we can take our marriage to a new level. Let's get dressed, go downstairs to the bar, and see where the evening takes us."

My head is still spinning. Unsure of what to say I just agree with my wife. "I love you too, and I trust you, and yes it was pretty amazing sharing Donald's cock and getting cum on my face."

"Speaking of cum,we need to wash your face and redo your makeup. Let's go for a less slutty look. How about pretty pink lipstick and matching nails? You don't have to answer, the bulge in your panties tells me you love this."

My wife finishes my makeup, she touches up hers and as we go downstairs, and she says, "There is still work to be done. We need to shave all your body hair, teach you to walk in heels, how to flirt and so much more, but you make a very pretty woman. I never had a best girlfriend to out with, but now I feel I do. Someone to go shopping with, someone to get their nails done with, someone to pick up men with."

Everything is happening so fast, I am nervous and excited at the same time. We get into the elevator to go downstairs. Three men get in at the same time. I am pretty sure they are staring at my wife, but it's nice to think they are looking me over at the same time.

My wife says,"Easy Brianna you can't get too excited over every man you see. The night is still young."

We go to the bar and find a little table in the corner. My wife says,"Since you are new at this just follow my lead." A waitress comes over to take our drink order. My wife orders some girly cosmopolitan, so I do the same. I am not much of a drinker so it doesn't take much to get me a littled buzzed. By the second drink my wife starts talking about some of the men in the bar.

"Brianna, do you think that guy in the blue shirt is cute? I bet he has a nice cock."

Then she spots two men, maybe in their twenties walking into the bar and she asks me, "Would you rather have an experienced older man or a young man in his early 20's?"

"I'm a little buzzed, what do you prefer?"

"Let's go to the ladies room, freshen our lipstick and see if anyone tries to pick us up."

We go to the ladies room, and as we head back to our table these two young men approach us and ask if they can buy us a drink. We say yes, and about 15 minutes later they bring drinks to our table. Their names are Robert and Brandon. Turns out the are each 19 years old, sophmores at a local college. They are trying to act cool, but clearly they do not have a lot of experience with women. My wife whispers in my ear, "Follow my lead, I think we can have fun with these two boys."

"How would you boys like to get your cocks sucked tonight?" she asks.

The boys nearly spill their drinks and I say, "I take that as a yes."

My wife gently rubs Brandon's cock and says, "Brianna, he is already hard, rub Robert's cock to see if he is hard. No need, I can see the bulge in his pants"

I tease him and rub his cock anyway, following the lead of my wife.

"Let's go up to our room.",my wife says.

We take the elevator upstairs. Robert tries to kiss me and feel me up, but my wife tells him to slow down til we get to our room.

We get to our room and my wife asks, "How would you boys like to see a little lesbian show before we give you a blow job?" It took two seconds before they both say yes.

"Ok, I will make out with Brianna if you two boys kiss each other"

They both hesitate for a moment and then give each other a quick kiss on the cheek.

"You call that a kiss? I want a full kiss on the lips with a little tongue, like this." Then she proceeds to kiss me. The boys hesitate again. This time my wife says," I guess you don't want to see our lesbian show. Then they look at each other and start to make out.

"Now that's what I call a kiss." Then she kisses me some more and we start feeling each other up. We are making out hot and heavy, then my wife pulls her panties down. "Do you boys want to see Brianna lick my pussy?" They instantly shake their heads yes.

"Then pull your pants down and start playing with each other's cocks." The boys are so confused they start playing with each others cocks.

"Look how hard they are Brianna, do you think they are gay?"

"I don't know."

Then my wife says, "I want to fuck Brandon, why don't you suck Robert's cock"

I start to suck Robert's cock. He is so excited by the little lesbian show he cums in my mouth after about thirty seconds. Brandon is fucking my wife and she is screaming, "I want that big cock inside of me, I want to feel your cum." A minute later he cums and my wife says, "Brianna please lick Brandon's cum from my pussy." As I lick my wife's pussy we notice the boys getting hard again. This time I give Brandon a blow job while Robert fucks my wife. I swallow another load of cum while my wife is moaning and begging for Robert's cock. Robert cums in my wife's pussy.

I lick my wife's pussy again tasting Robert's cum. Then I kiss each boy, trying to stick my tongue in their mouths to see if they can taste their cum. My wife kisses each of them and thanks them for a fun evening. They hug us and ask if we could do this again. My wife says, "Yes indeed, maybe next time you can bring some friends, Brianna loves to take multiple cocks."

The boys leave, my wife smiles at me. "You were great, hard to believe this was your first time. I guess those sissy videos taught you a thing or two. What was your favorite part?"

"I don't know, it was all amazing. The way the sexy panties and bras felt, watching you get fucked while I was sucking cock, swallowing cum, the way you made my eyes look so sexy, it was all unbelievable. But at the end of the day, I really love wearing lipstick."

"Yes, you do look hot in lipstick. I have one more surprise for you. Close your eyes."

I close my eyes.

"Now open them."

My wife is standing there wearing an 8"strap on, then in a deep manly voice she says, "Ready to get fucked, slut?"

I say yes.

"Bend over bitch, let me shove my cock in that sexy ass of yours."

She slowly puts the dildo in my ass. It hurts a little at first, but soon feels good as she starts fucking me. While she continues verbally humiliating me I am moaning and moaning, louder and louder, "Please fuck me, I want to be your whore." She is pounding my ass faster and faster, harder and harder, until I cum and collapse on the floor.

"You really are a slut, aren't you Brianna? I have one more surprise, I bought us matching nightgowns. Let's go to bed and get some sleep. We still have two days vacation left and if you want to suck some more cocks and get fucked in the ass you really need to get some rest."

The nightgown feels so sexy, "Thank you, this feels so silky, I love it. I can't wait to see what other surprises you have in store for the rest of the weekend. Goodnight, I love you."