Kinky Vacation

My wife and I were trying to figure out where to go on a long overdue vacation. Because of covid we had not gone away for nearly three years. We didn't know where we wanted to go. The northeast cold and snow had gotten the best of both of us and we just knew we had to go somewhere warm. We decided on one of those all inclusive tropical island getaways. Seven days of sun and fun. All you can eat, all you can drink, music, dancing, it was the perfect vacation.

The last full day we decided to take it easy. We packed for our early morning flight and then relaxed by the pool.

I asked my wife if there was anything special she wanted to do on our last night. Her answer shocked me.

"I want to have sex with the lifeguard."

I thought she was kidding, then she repeated, "I want to have sex with the lifeguard. Look at him, so young, so hot. Be a sweetheart and ask him if he would want to fuck me."

My wife is in her early 30's still hot looking, and even hotter looking in her bikini. She got plenty of looks from resort guests and staff during the week, but she would just politely smile when someone would hit on her.

After 5 minutes she asks again, "why are you still sitting here? Ask the lifeguard if he wants to fuck me."

All I can say is, "Yes dear."

I walk over to the lifeguard. As I get closer I would guess he is about 20 years old with a very athletic body.

"Excuse me Mr. lifeguard, my wife would like to have sex with you. She is the one over there on the lounge chair wearing the red bikini."

"Your wife is very sexy, I would love to fuck her. I am off all day tomorrow, will that work?"

I tell him we have an early flight and tonight is our last night here.

The lifeguard, whose name is Bill, says, "Sorry, I have a friend visiting that I haven't seen in a couple of years, and tonight is the only night we can get together. Does your wife know another woman for my friend?"

I tell him no and he apologizes, "I am sorry to disappoint your wife, I am sure we would have had some fun."

I go back to deliver the news to my wife. She is disappointed, but after a few minutes she tells me to go back to the lifeguard.

"Tell him I found a woman, tell Bill to come to our room with his friend at 8 o'clock."

I deliver the news to the lifeguard, he smiles and says, "Tell your wife Mike and I will be there."

I go back and tell my wife that Bill and Mike will be over to our room at 8, and she smiles. I ask who she found to go out with Mike, we really didn't make a lot of friends on this trip.

"Never you mind," she said, "Just go to our room, I will be back in an hour or so."

I go back to the room. Part of me is really angry that my wife wants to fuck some other guy, but I guess a small part of me is excited. I always thought we had a pretty good sex life, but now I am confused.

About an hour and a half later my wife comes back to the room carrying a handful of bags. I ask her if she found someone to go out with Mike. She tells me yes, and I ask, "Who did you find to go out with Mike, and why are you doing this?"

She replies, "The why is easy. Every now and then I need to get fucked by some hot young guy, hopefully with a big cock. It has been a fantasy of mine for awhile now, but I can't really act on it back home. I still love you, but we are on vacation, what better time to act on our fantasies. The who is YOU. I've been shopping for the past hour to buy panties, a bra, stockings, a sexy outfit, and some makeup. I always thought you had some feminine features and would make a very pretty girl. Sometimes when you stare at me when I am putting on lipstick I think you would like to put some on your lips."

I admit that I have fantasized about wearing lipstick, but my fantasies never included dating some guy.

"It's one thing wearing lipstick and dressing up in woman's clothes, but it's another thing being with some guy. I am not gay, and I am not really comfortable with this."

"Hush!" My wife says, "Nothing is going to happen if you don't want it to. I will be in the room with you the entire time, and I will make sure it doesn't get uncomfortable. Now let's hurry, we need to shave your legs."

Then she smiles and says, "No guy wants to feel hairy legs when he is running his hands up your stockings."

After my legs are shaved my wife goes thru the bags that she bought earlier and pulls out a pink pair of panties.

"Try these on."

I try on the panties and she asks, "How do they feel?"

I tell her they feel really good, but actually they feel better than really good. They feel amazing.

"I knew you would like them, it gets better from here."

Then she hands me a pair of thigh high stockings.

She can tell I am a bit puzzled.

"Let me put on my stockings first, pay attention and see how it's done."

I watch her and I feel myself getting an erection in my panties. My wife notices this and says, "Careful now, we can't have you getting hard under your girlie clothes, it might scare away your date. Now let's see you put on the stockings."

I carefully put on the stockings.

"Nicely done, let me help you with a bra."

She shows me a very lacy pink bra that matches my panties and puts it on me.

"Someday you will able to do this by yourself, but we don't have a lot of time today."

Then she hands me a cute little dress.

"We call this a cocktail dress, it's sexy without being slutty, and it matches the bra and panties. Put it on and then go look in the mirror."

I put on the dress and look in the mirror. I like what I see and smile.

"Very nice." My wife says, "Now let's do your makeup."

A few minutes later, some cover up and blush. Then some eye liner, mascara, eye shadow.

"You have always had nice blue eyes, now they are feminine and prettier."

Next lipstick, lipgloss and a blonde wig.

Then she says, "I told you that you would make a lovely girl, I need you to smile for a picture."

I love what I see in the mirror, and smile as she takes my picture. Then I ask again,"I don't have to have sex with this guy?"

She says, "Of course not, I will be here the whole time, you will be fine."

At 8 o'clock the doorbell rings. It's Bill and Mike right on time, with a couple of bottles of wine. My wife greets Bill with a big kiss, and introduces me as her friend Brianna. She goes into the kitchen with Bill to open the bottle of wine while me and Mike sit on the living room couch making small talk.

About 15 minutes go by, my wife and Bill are still in the kitchen, so we decide to join them. We walk into the kitchen and there is my wife on her knees with her hot red lipsticked lips sucking Bill's cock. We stand there for a few minutes before they notice us.

"Sorry." My wife says, "Bill just pulled out his huge cock and I just had to suck it. Why don't the two of you have a glass of wine while we go to the bedroom and fuck."

So much for, don't worry I will be with you the entire time. I never heard my wife talk like that. It was kind of a turn on, but I didn't know what to say to Mike or what is reaction would be.

I figured that out soon when I saw a big bulge in his pants. He suggested we go back in the livingroom and have some wine. By the second glass of wine I was feeling a little tipsy. Mike was getting a little touchy feely, but I kind of like it. My wife was right, having my shaved legs touched while wearing stockings was incredibly hot. Then Mike kissed me and we started making out. I never made out with a guy, but I got more and more excited as his tongue darted in and out of my mouth. His hand started inching closer to my dick when I said, "Sorry, I am having my period and I really don't want to have sex tonight."

He said he understood, but then he unzipped his pants and took my hand and placed it on his huge cock and said, "I know you want to suck on this."

He was right, I pulled down his pants and started sucking on his cock. I didn't know what I was doing, but Mike took the lead and shoved his cock all the way in my mouth and started fucking my mouth. I was starting to gag, but at the same time I was horny as hell. After a few minutes he let out a big moan, pulled his cock out of my mouth and came all over my face.

A few minutes later Bill and my wife come into the room. I am a little embarrassed with cum on my face, but nobody seems to mind.

My wife says, "Mike, let's trade places. You come with me while Bill stays here with Brianna. Brianna, come with me to the bathroom so I can help clean you up. Mike, I will meet you in the bedroom in two minutes."

I go into the bathroom with my wife. She washes my face and helps me fix my makeup. Then she says, "Bill is amazing, he has a huge cock and a great tongue. The minute I saw that cock he had complete control over me. I became his little slut and I would do whatever he said. He fucked me so hard that we both came twice, and he was still hard. I squirted for the first time ever, and had the greatest orgasms. And loving you like I do I thought you should enjoy his cock too."

Then she gave me a kiss and thanked me.

When I get back to the livingroom Bill is waiting with a big smile and a bulge in his pants. He greets me with a big kiss and tells me, "Your wife is one amazing fuck."

I play dumb, "My wife?"

Then Bill says, "Yes, your wife. She told me everything. She said once she saw my cock it was some kind of truth serum. She begged for my cock, did whatever I said, and told me everything. Funny, I don't even know her name. She kept begging, "fuck me like the slut that I am." After she came for the second time she told me how you liked to dress up and it would be a crime for my big cock not to fuck you."

Then he stuck his fingers in my mouth and said, "How do you like how your whore wife's pussy tastes?"

Then he pulls his cock out of his pants.

"Put those pretty lips on this and start sucking"

My wife was right, I took one look at his giant cock and I was under his complete command. I was sucking like there was tomorrow.

Then Bill started getting more verbally abusive.

"Tell me how much you love sucking my cock little girl."

"I love it, I love it," I replied.

"How much do you want this cock to fuck you?"

"I want it so bad," I screamed.

"Beg for it." He demands, "Beg for it like your slut wife."

"PLEASE!" I begged, "Please fuck my ass with your giant cock."

Then he bends me over and sticks his cock up my ass while he keeps teasing me.

"Tell me how much you love it."

His cock felt amazing as he pumped it in and out of me. And I beg some more, "I love it, I love it, please cum in my ass, I want to feel your cum inside of me."

After what felt like hours Bill finally cums in my ass, then smacks it for good measure before telling me to lick his cock clean. I do as I am told. I can't believe how submissive Bill makes me feel, but I am loving it.

Then my wife and Mike come out from the bedroom.

My wife asks. "What's all the noise out here?"

Bill explains, "It was just your husband begging for my cock. You were right about him, he does make a good submissive sissy. I think he is a bigger slut than you. And for future reference, he loves to get his ass spanked."

My wife adds, "He should get his ass spanked for not telling me he wanted to get dressed and suck cock, spank him again for good measure."

Bill bends me over and gives me three sharp whacks across my ass.

Then he asks, "Mike, did you cum in this sluts pussy?"

Mike nods yes, and Bill says, "I bet she would love Brianna to lick all that cum."

Then Bill adds, "C'mon Brianna, show us what a submissive slut you are. Crawl over and start cleaning your wife's pussy. And for good measure Mike and I will smack your ass."

I do as he says and start licking my wife's pussy. Tasting the combination of Bill and Mike's cum with my wife's juices, plus getting spanked in the ass is really getting me excited and I am getting hard.

Finally Bill orders me to stop licking. He tells me to stand next to him and compare the size of our cocks, and just laughs, "Poor Brianna, she got fucked, sucked cock, licked pussy, has a hard on, but is the only one who didn't get to cum. That's what you get for being a sissy whore."

Finally my wife says, "Thank you boys for a wonderful evening, but we have an early flight to catch tomorrow and you must be going."

The boys thank us, Bill gives my ass one more smack, and as they leave he says, "I sure hope you come back again."

My wife says, "We surely will, but until then I will be fantasizing about you cock."

Bill adds, "I'm sure Brianna will be fantasizing about it also."

Then my wife kisses them both and says, "Honey, make sure you kiss the boys goodbye and thank them for letting you share your mouth and ass with their lovely cocks."

I kiss them and thank them.

As they leave my wife asks, "Wasn't that amazing? I thought this would just be a vacation fling, but I think we should do this when we get home. Let's get some sleep, we need to wake up early."

The next morning we wake up and call a cab to take us to the airport. My wife seems to be walking a little slower, complaining of a sore pussy.

I say, "My ass hurts, I don't know if I can sit on a plane for three hours."

She says, "I'm sore too, but it was worth it."

I agree, and we both laugh.

To be continued.