Kelly’s Conundrum

So I am married, but I had an affair with a single woman, Kelly. We only actually got together once. We chatted and talked a lot, but after we got together she got serious with a boyfriend. I know from a physical standpoint sex with him was very vanilla, and well I wasn't vanilla.

She had admitted to me no one had ever made her cum or gone down on her. I broke both those records. When we got together, I pushed her back on the bed, and went down on her.

She has a sweet soft pussy. I licked and sucked on her pussy and clit. She had three orgasms before I stopped. I then crawled over her and fucked her until I came inside her. I rolled off her and laid back, and the next thing I know she is getting dressed, and leaving. We talked later and she said she was overwhelmed, and was driving home on Cloud 9 she came so much. I promised her next time to take her anal cherry that I was supposed to take our first time too.

Next time never happened, and I can't get her sweet tasting pussy, and her hot, wet, and soft pussy out of my head.

I am talking to a good friend of mine about her and he says "Give me her name and cell number. I know a guy that can do a quick work up on her."

"What?" I ask.

"Just give me the number." He says. I do and we talk for a while. I tell him about being bummed. I never got a chance to take her anal cherry, or to tie her up and have my way with her.

"Has she ever been with a woman, or does she want to fuck a woman?" Dennis asks.

"No she hasn't, and yes she does, but I don't know a woman." I say.

"I do." He says with a smile.

"You do? Who?" I ask.

"Jean." He says.

"Your girlfriend, Jean?" I ask.

"Yup." He says.

"Really?"

"Jean admitted to me she wants to try having sex with a woman while she was on Molly one night." He says, looking at me seriously.

I can't help laughing. "You have used Molly?" I ask in disbelief.

"Well it's a mix of Molly, the viagra for women Addyi, and pot, well the extract. Dave gave me 6 a while back to try. Jean gets extremely horny, relaxed and is up for Anything when she takes it." He says.

"No way!"

"Yes way. She has always been submissive, but with this stuff, I have tied her down to the bed, vibrated her silly, spanked her leaving handprints behind, fucked her ass and cum on her face. And she loves it all." He says.

"Who are you?" I ask laughing. We have never talked in this detail before. I am very surprised. Just then his phone dings. Dennis picks it up and my phone dings with an air drop from Dennis. I open it and look at it. It's Kelly's full name, address, DOB, credit report, DMV records. WTF!

"Dennis, I thought Dave was an attorney. How did he get all this?" I ask.

Dennis smiles. "His firm does a ton of divorce cases. He has told me he has an investigator that is absolutely amazing." He says.

"No shit." I mutter still flipping through it all.

Dennis looks at his phone. "Dave says he will have some financials in a bit." He says. "I'll make you a deal. I will get a nice room, and bring all the toys we will need. You bring Kelly, and we will all fuck her. Do you think she would like that?" Dennis asks.

"I know I would, and if this pill works like you say, and it gets her out of her head, feeling guilty about cheating on her boyfriend. You have a deal." I say.

I am at home later that night and I start pouring over all the information I got on Kelly. Dennis got more information as we were leaving the bar. The house she lives in belongs to her parents, which makes sense since I knew she lived with them. And thanks to the bank and credit card statements I know where Kelly goes to get waxed, and according to her charges it seems she goes around the first Friday of the month, followed by a stop at a local pot shop.

The first of the month is just a week away. I start to think and plan. The next day I call the salon she goes to for the waxing. I put a voice filter on my phone so I sound like a woman. "Hi, this is Kelly. I believe I have an appointment for Friday, but I forgot the time. Oh 5PM. Thank you." I say and hang up.

I text Dennis.

ME - Friday night?

DENNIS - The local Hilton. Rm 508. I will send you the link for the door when I check in, and I will drop by with a pill for you.

ME - What toys were you talking about?

DENNIS - Trust me I will have whatever you are looking for.

He sends a picture of a good sized duffle bag damn near full. And the zipper is open. I can see dildos, some straps, and a padded wrist restraint.

ME - Jesus. What the Fuck!

DENNIS - I told you Jean is submissive. I have had some fun with her. I will stop by after work with the pill for you next week.

I sit there shaking my head. I figured like most couples Dennis and Jean would have tried a toy or two, but I wasn't expecting a duffle bag full of shit.

I sit there contemplating how to approach Kelly. I decide I will run out tonight after dark and put a GPS tracker on her car so I can be sure she is going to the salon & the pot shop. If I remember correctly, when we were talking before she got serious with the boyfriend, he works early Saturday AM. So they don't go out on Friday nights. Now I might have to get a little heavy handed with her and fib a little to get her to agree to get in my car and take the pill. I mean I could hold the back of her head and force it down her throat, but I would rather not.

I sit in the parking lot of the pot shop waiting, when I see her pull up. I watch her walk in. I give her just a minute and I follow her in. I walk up behind her and decide to call her by her last name, that I didn't know before Dennis got me all the information.

I walk up behind her and tap her on the shoulder. She spins around and her face drops a little bit. She wasn't expecting to see me. Miss Jones, how are you? How are your parents Don & Mary?" I ask leaning in to give her a tight hug. I let my hand wander down just over her ass and back up.

She pulls away and looks up at me. She tries to play it cool when she notices people are watching. "They are good. How are you Larry?" She asks.

"I am great. I was about to get a six pack next door when I saw you walk in here. I had to come say hello. It's been a while." I say.

We keep up the small talk until she is called up. She gets a few things and it comes to just under $100. I am prepared. I grab a wad of cash out of my pocket and give the cashier $100.

She looks at me. "I have it." She says reaching for her purse.

I put my hand on her wrist and give it a gentle but firm squeeze as I rub my thumb on the back of her hand. "I insist. What are friends for?" I say as I smile and take the change from the cashier.

I grab Kelly's hand and hold it in mine. "Come on. Let's go catch up." I say a tad loud as we walk out. I walk her towards the passenger side of my car.

"Larry, I can't." She says softly.

"Yes you can. I open the door, and you sit in the car." I say.

She sighs. "Ok, I shouldn't." She says.

"Let's get in the car and discuss that." I say.

She stops in front of me. "I know what you want, if I get in that car." She says.

I move behind her and wrap my arms around her. We are half hidden by the car and shadows. I grab a boob in each hand and feel for her nipples. They are already hard. "It seems like your body definitely wants something." I say.

"Please, Larry." She begs. "Don't."

I let her boobs go. With one hand I open the car door, and with the other I gently grab and squeeze her ass. I try a slightly different approach. "Daddy says get in the car." I say as I let her ass cheek go and then spank her ass.

She gasps in surprise, and moans in defeat as she gets in the car. "YES!" I scream in my head as I get in the driver's seat and pull away.

"My car? Where are we going?" She asks surprised.

"Somewhere a little more private to talk, away from security cameras." I say with a smile. I pull into an old wooded area that leads to hiking trails. There are no cameras here. I flip the middle armrest up and turn towards her. I reach out and put my hand behind her head and pull her towards me as I move forward.

"Larry." She half sighs and half pleads just before my lips kiss hers. I push my tongue into her mouth and she moans and kisses me back. I let my hand slip from her head down over her boobs and between her legs. She has on loose shorts. Probably a good thing to wear after getting waxed. I slip my hand up the leg of her shorts and I can feel the heat and moisture from her pussy. Kelly pulls back from the kiss. "Please. I can't. How about I blow you and you can go home happy." She says.

With my hand still in her shorts rubbing her pussy through her silky underwear. "You can't deny it. Your nipples are hard." I say glancing down and the bumps on her shirt. I rub my knuckles a little harder against her pussy, and she moans. "Your pussy is obviously wet." I say as I lean in and kiss her again. There is no doubt she is kissing me too. I pull my hand out of her shorts. I reach into my shirt pocket for the pill. I reach up as I break the kiss. I run the back of my fingers along her lips and she opens her mouth to suck on them. Her eyes go wide as she realizes I have a pill in my hand that is now in her mouth. I push it into the back for her mouth, pull my fingers out, and hold her mouth closed. "Swallow it." I say as I look at her. "It's just a little something to help you relax and listen to your body. Don't make me hold your nose until you swallow it."

I can see the resignation in her eyes, and I watch her swallow. "Open." I say. She opens her mouth, and it's empty. I lean back in and kiss her deep. She doesn't resist as I kiss her. I slide my hand under her shirt and push it up. I pull her boob out of her bra and suck and nibble on the exposed nipple. Kelly holds my head to her chest, sighing as I do.

She runs her fingers in my hair. "Sit back and let me blow you. I will make you feel so good." She says softly & sweetly.

I sit up and look into her eyes. "Oh you will blow me tonight, and a whole lot more. Once we get to the hotel. Listen to your body." I say as I lean in and nuzzle her neck. "Does your boyfriend get you worked up like this?" I ask, but she doesn't answer. I grab the other side of her neck and hold her to me. "Do you want to explain a big hickie on your neck?" I ask as I apply a little suction to a kiss on her neck.

"No." She gasps. "No he doesn't." She sighs.

"Did you like when I went down on you?" I ask.

She sighs as I nibble on her earlobe. "You know I did." She says.

"Did you like feeling my dick pushing into your pussy?" I ask as I kiss her neck.

"Yes, you have a beautiful cock. I loved it inside of me." She sighs.

"Has your boyfriend tried to fuck your ass?" I ask.

"No." She sighs, sounding disappointed.

"Would you like me to take your anal cherry tonight?" I ask.

"Oh God! This is why I didn't want to see you again. I knew you would do this, and I wouldn't be able to say no." She says softly.

I reach my hand back up her shorts, and push her underwear aside. She isn't just moist she is wet. My fingers slide right through her soaked lips, and she moans as I rub her clit. "What did you give me? I am getting so sensitive and turned on right now." She says.

"A friend gave it to me. It's a mix of Molly, Addyi & THC." I say.

"Oh come on Molly! What's Addyi?" She asks.

"Molly to turn you on and lower your inhibitions. THC, well to relax you and maybe get you a bit high. And finally Addyi. It's the new female Viagra. It increases blood flow to your genitalia, and that physically excites you and makes your pussy wetter." I say.

"Ohh." She sighs as I pull my fingers away.

I smile to myself. Good! I sit up and pull out of the parking lot. "Put yourself together. The hotel is just 10 minutes away. This time you aren't leaving until I say you can, Little Girl." I say.

She smiles at me. "Yes, Daddy." She says putting her boob back in her bra.

I reach into the pocket on the car door. I feel the swim goggles I brought with me. I pull them out and put them in my pants pocket. I bought a cheap pair of swimming goggles, and put two coats of black paint on the lenses. I didn't want the top half of her face covered, and you can not see out of them.

We park and I help her out of the truck, and hook my arm in hers to make sure she can walk ok. Dennis and I talked earlier. He and Jean are already in the room. He will keep quiet until I have her tied to the bed. We make it through the lobby and onto the elevator. Once the doors close I reach down and cup my hand over her pussy and kiss her hard. She moans and kisses me back. I hear the ding for our stop and I pull away from her. Kelly doesn't move. You can see how horny she is. It's all over her face. I grab her hand and pull her off the elevator.

I open the app Dennis sent me and hold my phone to the door, and it clicks open. I walk us into the hallway of the room and stop. I look at Kelly and smile. I open the closet and like all hotel rooms there is a small safe. I recode it and turn to Kelly. "Strip and put all your clothes in the safe." I tell her.

"What?" She asks.

"You aren't leaving this time until I am done with you." I say as I push her against the wall and look down at her. "I plan on fucking your mouth, pussy and ass. And you aren't leaving until that's done." I say.

I can clearly see the lust burning in her eyes, as she reaches for the bottom of her shirt. She pulls it over her head. Once it's off she reaches behind her back and opens her bra. She shrugs it off, gravity takes over and her big tits fall out. She hands me her clothes and I stuff them in the small safe as I watch her step out of her sandals and push off her shorts and panties. She stands there smiling at me holding her shorts out to me hanging off a finger. I put them in the safe and close it.

I reach into my pocket and pull out the swim goggles. "Put them on." I say handing them to her. "I don't want you to see, I want you to feel everything that happens. And I don't want a big blindfold hiding half your face. I want to see the pleasure on your face, and maybe give you a facial."

"No one has ever done that before." She says as she puts on the goggles.

I reach out, hold her face and kiss her hard. "You may not be able to say that soon." I say.

I take her shoulders and spin her towards the room, and walk her in. As I walk in I see Dennis on the couch, his pants are off, with Jean naked on her knees quietly sucking on Dennis's dick. Jean looks good naked. She has a thick MILF body, with a good sized ass, hips and tits. What surprises me are her big nipples. They look like they would be fun to suck and chew on.

I stop Kelly at the foot of the bed. It's a high bed which be nice for fucking her while standing beside the bed. I turn her around and push her back. "Sit." I say as she half falls, half sits on the edge of the bed.

I smile as I look at the bed. Dennis has tie downs already on the corners of the mattress. He has a set of padded wrist and ankle restraints, and a spreader bar. I laugh to myself. I never knew Dennis was into bondage with Jean. I grab a restraint and her wrist. As I start strapping it to her wrist I can see the surprise and nervousness on her face. I start talking to her. "I am going to do Everything to you that you told me you fantasized about. I am going to restrain you. I am going to eat you out again. I am going to use a vibrator on you until you scream. I am going to cum in your mouth and on your face. You are going to get fucked senseless." I finish saying as I snug down her second wrist restraint. I push her back flat onto the bed. I grab her ankle and pull it back. "Ankles." I say.

I finish her ankles and grab the bar. I click in one ankle, and I can see the confusion on her face. She isn't sure what's happening. She was expecting to get tied to the bed. When I click her other ankle in she gets it. "Oh God." She moans. I reach down and grab her wrist. As I pull it to the bar and click it in place. She sighs. "Oh Shit."

I stand back and look at her. I realize I have her too far at the bottom of the bed, but I also realize she is Extremely turned on. Her nipples are hard, and her pussy is obviously red and wet, and I have done nothing but tease her pussy through her shorts. I get on the bed behind her and reach under her armpits. "I should have moved you up the bed before I tied you up." I say as I pull her most of the way up the bed. I move, and put a pillow under her head, and I step back.

I sometimes forget Jean is deaf. I want her to "hear" this if you will, so I wave to Dennis, and Dennis turns Jean towards me so she can read my lips. "So remind me." I say. "I was the first person to ever go down on you last time right?" I ask.

I see the disbelief in Jean's face. "Yes." Says Kelly, and I nod Yes for Jean.

"And did I give you two or three orgasms when I went down on you?" I ask.

"Three amazing orgasms." She sighs.

I repeat it for Jean. "Three amazing orgasms. I guess I did a good job." I say. I want Jean to know they were amazing orgasms. Jean smiles and gives me a thumbs up. "Do you think a woman would do a better job than I did?" I ask.

"Oh I don't know, but I would sure like to find out someday. Right now I want to feel your amazing tongue again, please. I am so turned on." Kelly says as I watch Dennis sign it for Jean.

"Do you think you would want to go down on a woman, or have a woman go down on you more?" I ask.

"Right now I am so turned I wouldn't care if a man or woman went down on me. I just want to feel you lick me. Please go down on me. I want to feel your mouth on my pussy again." Kelly begs.

"Who am I to say no to a horny woman." I say as I wave Jean over, and point at Kelly's pussy. Jean looks at Dennis looking a bit more nervous than horny. I watch Dennis sigh something to Jean, she nods yes, and he just points to Kelly.

Jean stands up and realizes I am looking at her naked. I watch her blush a bit. I smile at her, and mouth. "Fucking Sexy." Jean blushes a little more, as she climbs onto the bed. She stops for a moment and just looks at Kelly's wet red pussy.

"Please. I will do anything. Don't make me beg." Kelly says. Jean must have caught most of that by reading her lips. She reaches out and gently runs her fingers over Kelly's wet lips, and hard clit that is just peeking out. "Please." Begs Kelly.

Jean smiles, leans down and licks up Kelly's pussy. She pulls back smiling and looks at Dennis as she licks her lips. She then bends back down to lick Kelly's clit. Kelly sighs. "God I can't believe how good this feels."

To Jean's credit she doesn't stop. She keeps licking and sucking on her first pussy. She spends a lot of time sucking and licking on Kelly's clit, and Kelly is definitely enjoying it. It's a different experience standing back and watching Kelly as she cums. Her breathing comes in gasps. Her wrists pull against her restraints. This rolls her hips, and pushes Kelly's thigh against Jean's face as she cums. "AAAAHHHHHH!" Jean keeps a hold of Kelly's hips and keeps eating Kelly through her orgasm.

Kelly lets out a big sigh as she rolls her hips flat again, and Jean keeps licking. "Oh. Oh you are so good at...wait." She says as she wiggles her hips bouncing her thigh off Jean again. Kelly rolls her head to the side facing the room. "Larry who is....ooohhh...between my thighs? I know it's not you. They have a smooth face. What are you doing? Ooohhhh." She asks.

I stand beside the bed near her head. "Didn't you once say you wanted to have a threesome? I brought a good friend of mine with me tonight." I say.

"Oh God. Two men are going to fuck me." She sighs.

"Oh two men are definitely fucking you. I warned you. You aren't leaving until I, well we are done with you." I say.