She starts to get excited knowing I always give great surprises and tries to get me to tell her what the plans are, or at least give her a few hints.
I smile knowing she has no idea what I have planned, but do tell her, “Well, I need you to at least help prepare for it. I will tell you this much, you need to pack a suitcase for a three day weekend, but you need to pack two, one for warm weather and one for cold weather.”
She looks puzzled and asks “Are we going two different places?”
I just laugh and confess, “No honey, I don’t want you to guess, so you need to do both to be prepared and I will take the right one.” She then looks over and sees two pieces of identical luggage. “Just so you don’t think I’m giving you any clues, I will grab the right luggage.”
For the next few days, Kendra tries to get hints from me, but I won’t budge. The night before we leave, we are in bed and she starts to fondle my cock. “If I give you a great blow job will you tell me or at least give me a hint?”
I laugh and say, “Maybe.”
Then Kendra pulls down my boxers and starts to work her magic with her mouth on my cock. This time she uses all the tricks she’s learned over the years to make it more incredible. Looking up as she sucks it, using her hand to stroke it as she sucks and goes from light to hard pressure from time to time. She knows she has me like putty in hands when she feels my hands go on top of her head. Every time I do that, she knows I’m about to come and I blow a huge load deep into her throat.
She takes it and swallows it and looks up and asks, “What’s my hint?”
I laugh loud and joke, “I said maybe.” She playfully calls me a bastard and I say “Well, let’s just say it will blow your mind, things you’ve wanted to see and do.”
She perks up but knows it’s not much of a hint and is a bit annoyed thinking I’d give her more. I get out of bed to go to brush my teeth and come out seeing her pulling the belt out of my pants. She gives me a wicked grin and says “I saw this in a movie once” and puts the belt under my elbows and behind my back and fastens it.
“Holy shit Kendra, that hurts a little” as my elbows are pinned and I’m completely immobile with my arms. She grabs the belt and pulls me over to the bed and pushes me back and lose my balance and fall onto my back.
She gets on the bed and starts to play with my nipples with gentle kissing and sucking. My cock starts to get hard again from the attention to my nipples. She looks up and says “That was such a weak hint, I think I need to punish you.”
I smile and say “God yes, if this is your punishment, keep going.” But then her gentle nibbling and sucking becomes much more intense and her teeth start to dig in to my hard nipples. I start to fidget and moan more as she continues.
She looks up with a devilish smile and says, “Well, if you’re not gonna give me any hints, I thought I should make this nipples sore for the entire 3 day weekend” and starts to go harder and harder. I always love it when my nipples are played with, but this time the right one is tormented by her mouth and the left one by her fingers and nails. I get more vocal and she reaches down, slides off her panties and comes up and stuffs them in my mouth.
“Since you’re not giving me any hints and you’re squealing a little louder than normal, you need this” as she puts the wet part of the fabric on my lips and then uses a finger to push them in a little by a little. She smiles as I’m there with my arms bound and her pink panties in my mouth. When my mouth is full, she continues going back to working on my nipples. After about 15 minutes, they are sore and burning and I finally get relief as she stops on my nipples and goes down to stroking my cock sensually.
She then moves up and straddles my cock and I enter her wet pussy, as she starts to move up and down. My body is sensitive from the attention as I buck my hips to help with the momentum. She looks me in the eye and says “If I let you come, will you give me more hints?” I shake my head no as she moves her hips more and says “Pretty please, if I let you come, will you tell me?”
She can tell I’m in agony between wanting to come and not telling her more. I keep moving my hips and catch her off guard by climaxing earlier than she expects. She looks at me and says “Darn you, I was gonna get you to break.” But then pinches my nipples hard, making me squeal into the panties, leaving out just a muffled sound.
The then pulls out the panties and moves up quick and straddles my face. Over the years, I’ve eaten her pussy a few times after sex, but she knows it’s not one of my favorite things. Normally, she does it if I come too fast before she gets off and I usually focus on her clit, not her used pussy. This time when she comes up, her pussy goes right over my mouth. I can’t move still as the mixture of my climax and hers seeps from her pussy into my mouth.
She reaches back and teases my cock as I go soft. She knows how sensitive it is right after an orgasm and really torments it with her fingers. When her pussy is finally drained and clean, she rolls off and smiles. “Since you didn’t give me a hint, I thought you might deserved punished.” She playfully flicks a nipple and I wince and she adds, “MMM, good, those will be sore for a while.”
She has me sit up and unfastens the belt from my arms. I get the blood flowing again and I say “Damn, that was a lot. You will pay for that this weekend. I wasn’t sure I was going to at first, but now, I know all bets are off.”
She looks and says, “But you won’t do anything I don’t want, right?”
“Well Kendra, you know I would never do anything you were totally against, but I’m gonna push it now.” I play with her used pussy and say “You can always say no, but I don’t think you will. But if you want to stop at any point, you just need to say ‘Aim to please’ and I will stop. I hope you won’t, but I will stop if you say it.”
I can tell her mind is racing but we head to bed. The next morning comes and I grab one suitcase and head out. We get to the airport and sit by the gate that has a Miami flight departing. She keeps trying to get more hints.
After about 30 minutes of waiting, I take her hand and move her to another gate and start to board and then she realizes we are going to New York City for the weekend and starts to get excited. It’s about 6 PM when we land and get to the hotel at Times Square.
“Kendra, I need to take care of a few things, I have a favor to ask of you.” I reach into my wallet and get a credit card. “Gotta love New York. There’s a sex toy shop right across the street, why don’t you go browse a while and get a few fun things for the weekend and to take home.” She looks a little nervous but agrees.
I text her when I’m finished and we meet at the hotel. I ask what she got and she shows me some fur lined cuffed, nipple clamps, a dildo, a vibrator and some oils and stuff. I tell her to get dressed, we only have about 30 minutes. We both get ready and head out for dinner and drinks in NYC for New Year’s Eve. We have a magical evening and finish us the night with drinks over looking Times Square and the ball drop.
It takes a while to get back to the hotel. We’re a little tired from trip and night out. We have a nice but fairly quick round of sex and both pass out pretty quickly on the bed. We get up in the morning, have breakfast and head out for some sightseeing. We get back to the hotel around 2 and I go in and run a bubble bath for her. “Why don’t you relax a little, we had a long day.” As she gets in, I bring in a bottle of wine and light a few candles.
“Hey Drew, are you trying to get me drunk and seduce me?”
I laugh and say “Seduce, no” and laugh more as I fill up her glass and head out to the room. For the next 45 minutes, she relaxes and I keep filling up her glass. She gets out of the tub and I immediately start kissing her passionately and taking her to the bed. I throw her on the bed and keep kissing passionately. I start to move to her chest and playfully bite her nipple harder than normal and look up, “You were so cruel the night before we, I might have to get back at you.”
She smiles and says “Go for it.”
I get off the bed and get the cuffs she bought and put her hands above her head and bind her to the headboard. She is always a little nervous about being cuffed like that, so I leave enough room she can get out if she really wants too. I move down between her legs and start to kiss and lick her pussy for a minute or two. But I get up and head to the bathroom and come back.
“You know there is always something I wanted to try but you never really game for it, but since it’s a new year, I thought what the hell.” I move in and push her knees apart and reach back and get some shaving cream and start to apply it over the hair on her trimmed pussy. She looks down and says “What the hell are you doing?”
I smile and say “Well, I asked you to shave for me and you never did, so I thought I’d just shave it for you.” She looks nervous and I use the razor and take a swipe across the top of her pussy. “Well, I started, I better finish now. You better be still, wouldn’t want to cut you here.” For the next 10 minutes, she looks down and watches me shave her pussy bare. She sees I’m very focused on being careful but also getting all of the hair off. When I finish, I take a towel and remove the extra shaving cream.
I look up and say “Now that’s a pretty pussy, perfect for eating” and I dive down and start to lick and suck. This time, I do more licking and kissing on the bare skin around the pussy. Using my tongue to trace different paths and shapes. She always liked how I ate her pussy but tonight I am spending more time around the area right next to her slit. It builds in anticipation and when I finally get to her clit, she climaxes so quickly from the build up. “God baby, you should have done that years ago, makes licking you even more fun.”
I finish and she looks down and says “I can’t believe you shaved me, I told you I don’t like being bare like that.”
I giggle, “Well baby, you know I don’t really like you making me eat a messy pussy but you did that. And you know you just had to say ‘Aim to please’ and I would have stopped. In fact, I think you liked the attention I paid to your perfect pussy. You sure didn’t complain when I was worshipping it.” I come up and uncuff her hands and get a bottle of liquor and two shot glasses and we do back-to-back shots. I look into the bag of what she bought from the toy store and get out some of the massage oil and have her lay on her stomach as I start to work the oil into her skin on her back.
As I give her the massage, she continues to feel my erection against her flesh, slightly humping her. I move down and start to massage her ass cheeks. My fingers move down to her pussy and start to enter it and then use my hands to lift up her hips, putting her on all fours. I can’t take it anymore and I start to fuck her hard from behind. My cock is aching from the excitement of shaving the pussy and the massage and I pound hard and fast. I don’t last very long as I fill her pussy with a load of hot come.
I keep my knees pressed against her legs as I get some of the lotion and start to rub it on her ass cheeks for a few minutes. I then spread the cheeks and she feels my finger on her ass hole, teasing it with little circles. Then she feels more lotion go on the hole and I slowly slide a finger in her ass. Kendra looks back and says “What are you doing?”
I laugh, “Well, if you don’t know, I’m not doing a very good job at it” and I start to slide my finger in deeper. I take my time on her tight hole, adding more lotion and moving my finger to loosen her up. I reach down into the bag and get the little vibrator she bought and put it on the rim of her ass and slowly insert it. She’s had enough to drink and I warmed her up enough that she takes the vibrator pretty easy. I guide it in and out slowly as I come up and whisper, “I’m gonna take your ass right now. ”
She’s always been adventurous in bed, but the ass is one thing she was never really fond of because she thought it hurts too much. I keep working the vibrator on her ass and then pull it out and move up and put the tip of my cock on her asshole. “You want it Kendra, don’t you?” I ask.
She doesn’t answer and I put some pressure on the rim and say “Say it Kendra, say you want me to take your ass, tell me.”
After a second I hear a murmur, “Yes, take my ass.” I slowly use my cock on her tight hole and take my time as not to hurt her. The lotion, liquor and vibrator have loosened her up quite a bit as I start to get into the rhythm on her hole. Once I know she can take it, I start to pick up the pace. She feels my hand on her upper back, pushing her head down as her ass is in the air. I playfully spank her ass as I take her from behind. With the tightness of her ass on my cock, it doesn’t take long for me to climax hard and fast, deep in her ass.
I pull out and roll over and kiss her and say “I told you I was going to rock your world and explore new things. And the weekend has just begun.”
As she lays on the bed to recover, I smile and say “I have two new year’s presents, naughty and nice, which do you prefer first?”
She looks a bit disheveled and comments “After that, I better take nice.” I hand her two wrapped boxes. Of course, she goes for the bigger one and opens it.
As she pulls out a pair of leather boots, I comment, “You always commented how much you liked Jill’s boots, so I had a pair custom made for you. I hope you like.” She smiles looking at them, how nice they are and how much they must have cost to be custom made to fit properly. She gives me a kiss and goes for the other box and pulls out a black skirt, just like the one Jill wore with the boots.
I add, “I know you’re not really a dress or skirt person, but you always commented how hot Jill looked when she wears that. I think it’s sexy too, so I want you to wear it tonight for me.”
She puts on the boots and they fit perfectly, but she wobbles a little on the four inch heel. Kendra normally dresses more for comfort, but I convince her to give them a try.
I get the other box, much smaller and comment, “Time for the naughty present.” I hand it to her and she opens it and can tell it’s lingerie right away. As she pulls out the red panties, she notices they are a little different and sees the tag that says “Crotchless.” I giggle as she holds them up.
“You expect me to wear these Drew?” she asks.
I smile and say, “Yes, tonight and the other thing in the box too.” As she pulls out the bra, she looks and sees it’s basically a half bra. There is material and support for under her breast, but wide open for the nipple.
“Come on Drew,” she gasps, “I will fall out of this. You know my boobs are too big.”
I laugh and say “Well, I asked the salesgirl if it would work and she said they are made to help support too. Give it a shot.”
Kendra goes into the bathroom and comes out wearing the panties and the bra. She is surprised at how much support the bra gives her, even though her nipples are showing. I drop to my knees and playfully kiss her pussy threw the opening in the crotchless panties. I giggle, “Mmm, I do love easy access.” I stop and say, “You have to get dressed baby, reservations in 30 minutes.”
We both get ready and head down to the hotel restaurant. Kendra comments how her nipples are sensitive since they are bare and rubbing against her sweater. I laugh and say “Well, they aren’t as sore as mine from the other night” which causes her to laugh.
We sit down and have a few drinks at the bar and then Kendra is surprised by a hug from behind and kiss on the cheek. She turns and it’s Jill there. She squeals and stands and gives her a big hug. Jill smiles and says “Thanks for letting me know you were coming up Drew, we are here visiting friends.”
We have quite a few drinks and the liquor starts flowing and Jill comments how much she likes the boots I bought. “Thanks for your help Jill,” I comment, “I didn’t know where to start. But I think Kendra loves the boots, maybe a little more than the other things I got.”
Being drunk, Jill asks “What other things” and I tell her about the panties and bra. Since Jill is normally pretty open sexually and has a few drinks, she laughs and says “I was wondering why her nipples have been sticking out all night.” Kendra looks down and blushes. Jill adds, “Don’t worry, kind of sexy” and puts her hand on Kendra’s knee.
We have a few drinks and then Jill stands up and waves. Over walks her husband Brian and an old college friend, Jeff. They grab a few chairs and join us and we have more drinks. I smile watching Kendra because she always thought Brian was the hottest hubby of any of her friends and I see her literally licking her lips, looking at Jeff time to time.
The drinks gets stronger and stronger and everyone gets drunk. After a while, Kendra tells stories about the last vacation where she got so drunk and doesn’t remember much and how she loves her Dirty Whore Sex. She gets pretty graphic talking about how everything is open to her. The guys get up and chat with another college friend and I lean in and whisper something to Jill.
She looks at Kendra and says, “Did he really shave you there?”
Kendra blushes, but has enough alcohol to nod. Jill looks at me and says, “I can’t believe you did it.” It hits Kendra I told Jill my plans. Jill looks at Kendra and says “Can I see?”
I grab both their hands and take them back up to the room. Everyone is pretty drunk as I stand behind Kendra and kiss her neck and lift up her skirt. Jill smiles as she sees the crotchless panties and her soft fingers caress the new bare skin. “Drew did a good job, but you should wax Kendra, must softer.”
I’m behind Kendra as I fondle her tits and nipples through her top and Jill kneels and starts to go under her skirt. She feels Jill’s tongue on her pussy which sends shock waves through her body. I pull off Kendra’s sweater, showing her hug tits, barely covered and then unzip the skirt and let it fall. Jill looks up and smiles seeing the outfit. “Wow Drew, you sure did go slutty, I like it” and goes back to licking Kendra’s pussy. From the alcohol and excitement of her pussy being licked, she climaxes fast.
“Thanks Jill” I say,” but Kendra’s true fantasy is to go down on you.” Kendra is embarrassed I said that but doesn’t argue and Jill sits in a chair, lifts her skirt and puts one leg over each arm of the chair. She uses one of her painted nails to slide her panties to one side, exposing her bare pussy.
Jill looks down at Kendra and says “Lick, see how much softer a waxing is.” Kendra goes in and starts licking hard and fast. She’s as anxious as a schoolboy with his first girl, licking and sucking. I turn on some music to drown out some of the noise from the room, but both women don’t hear much as they focus on each other.
As Jill climaxes, I am behind Kendra and say “You are a dirty little whore when you’re drunk, aren’t you?”
She moans, “Yes.”
I add, “Tell me how much of a whore you are, how much you want to be.”
I pull her hair a little and says “I’m a total whore, I like it nasty.”
I moan and lean down and say, “Oh, you are a whore tonight” and take a blindfold put it on her eyes. I command in a louder tone “If you take off the blindfold, the night and fantasy are over.” She feels something go on her wrists again. When I’m done, she moves her arms quite a bit but when she tries to get them to go forward, she feels a chain against her back. She realizes she has quite a bit of motion but can’t get her hands too far out in front of her.
Kendra feels hands playing with her nipples, pinching and twisting them. Then she feels the hands move to her pussy which is dripping from Jill’s attention. In a fast movement, she feels hands on her hips that guide her over a pair of legs sitting on the edge of the bed and then pulls her down hard onto a cock and starts to fuck her hard. She always likes to be on top, but being blindfolded and semi-bound makes it harder for her to control the motion. Her pussy is aching from the build up all day as she is getting fucked hard and fast.
Kendra feels a pair of hands on her hand and I lean in a whisper. “Yes you are a whore baby, a total whore. In fact you’re gonna get fucked in all three holes tonight.”
She moans from the comment and thinks I’m gonna take her a few different ways, but then the hands push her head down to one side. Her pussy is still getting fucked on top of his lap but then she feels the tip of another cock on her lips. He pulls her hair slightly and she opens it up and he starts to pound her mouth with his cock.
Kendra’s body is in spasms as her pussy and mouth are both getting fucked at the same time. After a few minutes when the shock wears off, she gets much better at focusing on the blow job as she is taking the cock in her pussy. Her body is bent over as she sucks him and then she feels something go against her ass.
A second later, she is being fucked in the mouth, pussy and ass, at the same time by three different men. She squeals as she takes all three at one time. Her mouth is fucked so hard but the other guys are gentle enough as not to hurt her, but hard enough to push her body to its limit.
With her ass being so tight, the first guy holds on to her hips and pumps her a little faster and shoots a big load of come deep into her ass. That feeling sends Kendra over the edge and she has a hard climax which tightens her pussy muscles. Her climax and tightening is enough to send the second guy over the deep end and he climaxes and fills her pussy with a load of hot come. With both guys done in her ass and pussy, the other guy grabs Kendra’s head and starts fucking her mouth harder and faster.
She can barely keep balance and struggles with breathing with her mouth being used like a sex toy. A few minutes later, she can tell by the movement and pace, he’s about to come and a second later, she takes her third load of come directly in her mouth. The guy moves off the bed and she collapses hard on the bed in exhaustion. Still blindfolded, she hears movement and the door close.
A minute later, the bed moves again and Kendra feels her hair being pulled a little and then pushed down and smells a pussy this time instead of a cock. Jill pulls off the blindfold and pushes Kendra’s head to her pussy and says “God that was so hot seeing you fucked by Drew, Brian and Jeff. The best part is you don’t know which one of them took you in which hole.”
“Lick my pussy Kendra. I love you drunk since you like Dirty Whore Sex,” as she pushes her head down further and wraps her legs around Kendra’s head. The heels of Jill’s boots dig into Kendra’s back as she climaxes hard and lets her up to breathe.
Jill smiles and says, “Happy New Year.” She gets up and gives me a hug and kiss on the cheek and says, “Tomorrow at 4 right?” and leaves…….