The Wedding... part 1
written by:
jwdoney

This is a work of fiction created for and inspired by ideas submitted from two very loyal readers, James F. who is also my friend and editor and Dennis D. a longtime, loyal reader who is not afraid to tell me the truth when no one else will. Initially these ideas would have each made a great one off or short solo story, but after some careful thought, I came up with this idea, I hope you all like it.

This story involves casual sex with multiple partners and cheating, therefore it is not my typical fare. In the style of ALICIA AND THE BIKINI STORE, TANYA, and some of my other mayhem stories, this character will get laid alot, but the humor, scenarios and situations will make it fun. I do not advocate any of what I am about to write, including the careless afterthought of casual, freerunning sex and/or multiple lovers. This is only a story and my personal feelings and morals conflict with this style of writing. That being said, there is something exciting about sex without drama, stress and constant conversation. It happens in real life, so here's hoping my words evoke that... enjoy.

Any people, places, names, products or events mentioned are done so without permission or endorsement. This is a work of fiction.

My name is James Dennis, but my friends call me JD. I am 30 years old, stand 6' tall, have short black hair and a fit, athletic build thanks to running and working out often. I am single, live alone, and getting a date isn't an issue. Finding someone who wants to be in a relationship is hard, hooking up is not. I am seeing a girl that works with me, her name is Anna, but she wants to keep it light and it's less about dating and more about her staying over a few nights a week. We've been lovers but not dating for a long time, seeing each other, but not committed for over a year. Anna wants to be free, but wants to be with me, it's very confusing. I work for my parents who own several businesses. Mostly I manage things, keep all paperwork up to date, and pretty much handle HR, PR and personnel. My parents own a lot of property, most of which they rent or lease, including the small house they rent to me for $500 a month, which is way under market value. I've had money all my life, but I was raised right and never acted arrogant or entitled. The point of this story isn't that I'm single or can't find a girlfriend, I basically have one with Anna. Mostly.

My current issue is I have to go to Texas for my best friend's wedding in three days, and today is my fitting for the tux. Anna couldn't go so I'm going solo which works for me, because weddings are like catnip to single women. Anna is handling my travel, tickets and so forth, and she did something strange when I left to go to the tux fitting... she held me, stared into my eyes, then whispered "I'm going to miss you". I swear she was going to say three certain other words, but still, ‘I'm going to miss you' was huge coming from Anna. 29, 5' 8" and petite with long blonde hair, Anna is gorgeous, shapely and just plain beautiful. We kissed slow and warm and she said "When you get back, I'll stay over and you can tell me all about it". I smiled then said "I know what else we can do". Anna blushed and said "Maybe I'll stay over tonight and we can discuss the what else". Mom was coming into the office as I came out and she stopped, we hugged, and I said her favorite line "Man, if you weren't my mom..." She sighed and said "Then you wouldn't be here. That never gets old".

Mom is 48 and looks 30 with a body that I should NOT be thinking about. Dad is still buff and handsome at 49, they both stay active and look great, but mom still has it and she knows it. I winked at mom and said "You know that mom and son is a thing now" and she blushed and said "James Dennis, you are so naughty. Go take your ideas out on Anna" and she went into the office. I drove to the shop we've been using since my prom. I personally think mom and dad are investors or secretly own the bridal shop, but either way, they always treat me like royalty. I went inside and Gina was there and she looked hotter than usual, which is saying something. Maybe I was horny today, but Anna, my own mother, and now Gina... every woman I saw got me stoked. Gina is in her early 40's and is the walking definition of a MILF, especially since her daughter Rachel just turned 18 and is smoking hot herself. I glanced around the shop but didn't see Rachel and sighed... it didn't matter, Gina was hotter than fire, especially today.

Gina had on a short, knee length black skirt that was loose and flirty, a white button up blouse that was sheer enough to hint at a dark colored bra underneath. Her black heels were low and her long red hair was down and wavy, Gina looked amazing. She thanked a customer then smiled at me and said "You come here". Gina wrapped me up in a huge hug that sent electricity through my body and then shocked me completely when she kissed me on the lips. I got confused and tried to kiss her and Gina said "Oh..." then the next thing I knew we were kissing passionately. After the kiss, Gina stepped back holding my hands and said "I think you're excited to see me" and I gasped "Who wouldn't be?" She flirted with her eyes then said "Shall we? I have it ready back here". We went to the back and Gina led me to the private fitting room which has wall to wall mirrors and a large futon. I've made the joke before on a prior fitting, but I said "God it would be amazing to have sex in this room". Gina smiled slowly as she looked at herself in every mirror then said "Yeah..."

I looked at the tux and it seemed squared away, so I said "I'll just try this on and see what you think". Gina sat on the futon and I could see her panties were a soft purple, almost lilac. Now that I thought about it, her bra could be that same color. I blinked and asked "You're going to stay in here?" Gina smiled and said "Of course. You're wearing underwear aren't you? Don't be shy, I have to see how it looks on you and be ready if anything needs to be altered". Right. Okay. I took off my shirt and Gina took it, folded it, then said "Hold on" as she stood and slid her hand slowly around and on my bare chest. She said "You're buffer that I thought... hmmm..." Was buffer a word? Who cares. Gina stood close to me and said "Alright, keep going, we'll figure it out once you have it on". I took off my shoes and pushed them under the futon then undid my pants. Gina took them from me, folded them, then crouched to touch and rub my legs, especially my thighs. She was hot as Hell, her skirt was hiked practically to her waist, her panties were pulled tight against her crotch... so I started getting hard.

Gina stayed where she was and said "Okay, this isn't going to work. You need to calm down, that tux is fitted and I didn't expect this". Gina poked my bulge with her manicured nail and left her fingertip there as she looked up at me. I was feeling bold and horny so I said "I can't help it Gina. On a normal day, you're easily a 10, but today you're like a 13 at least". Gina blinked twice, exhaled, stood, then said "I never do this". She went over to the door, flicked the lock, then started to unbutton her blouse. I stared as her lilac bra came into view and then she undid and slid her skirt off, pulled the blouse off, then stood before me in her lingerie. Oh my God she was hot. I was shaking and my cock ached as Gina said "Your move". I moved closer and kissed her softly, but our hunger overtook us and we were pulling at each other's underwear. I got her bra off, she pulled at my briefs, and then I watched as she slipped her panties down. We got onto the futon and Gina said "No one can know about this" and I said "I swear".

Gina pulled me to her and there was no foreplay, we had barely kissed twice, and I slid inside her warm, wet, and very tight pussy. Gina moaned and said "You're bigger than Ryan". Her husband was actually a nice guy, but Gina said "Don't worry about him, he has his deal, I have mine... it's how we stay happily married". Okay then. I stroked deep into Gina and she held me with her warm hands, slid them along my sides, all while smiling up at me. My mind was blown, this was my first MILF sex, Hell... this was my first casual encounter period, and it was exhilarating. Gina said "Wherever your mind is going, don't forget about me" and I stared into her eyes then kissed her furiously. I can't ever remember being so excited and aroused and Gina was an amorous lover to say the least. The more I thought about it, there had been no drama, no hard work, no commitment or complaining or conditions, Gina just met my excitement and we here having sex.

I was so hard it hurt and I realized I was driving into Gina and slowed my pace. She stared at me intently and asked "What's wrong?" I kept going even as I said "I just... it felt like I was fucking you". Gina gasped, then laughed "You are, and trust me, I'm enjoying it". I kept going and Gina moaned then said "Stop thinking and enjoy this...". So I did. We kept at it until Gina tightened around me, her body tensed, and her eyes were locked onto me. She was breathing deep and heavy and clinging to me firmly as I just stroked deep and hard. My cock ached and I knew I was close even as Gina seemed to be holding her breath and staring at me. She asked "Are... are you..." she moaned and her eyes rolled back then Gina exhaled slowly and asked "...close?" I nodded and she smiled then gasped "Give it to me" and I came. I exploded deep inside Gina in a blinding explosion that numbed my body and muddled my brain. Gina was panting, gasping, and moaning, then rammed her face into my shoulder and even muffled, her scream was loud. We came together and finished together and the entire thing start to finish was mind blowing.

Gina held me until we started to kiss and she said "Okay, you need to actually try the tux on now. I have to see if it fits before you take it with you". We cleaned up using a small black towel that Gina handed me and she was dressed by the time I had the tux on, She was very informal and touched me a lot, but in the end the tux fit perfectly and she smiled at me then said "I do good work". I took it off, got dressed, and Gina touched my chest while I was tying my shoes. She said "Just so there's no confusion, this is not something I just do, and it won't happen again. You excited me, we had fun, and now we go back to being friends... with a secret". I smiled and said "Best secret I've ever had". Gina stared into my eyes for a long time, then finally asked "Seriously?" I said "By far". Gina stared into my eyes and said "Maybe... maybe when you get back and return the tux... maybe we can have another secret... maybe". I smiled and said "I look forward to it". Gina blushed then smiled and said "You should". She kissed me softly then said "Deep breath then walk of shame, are you ready?" I smiled and said "Yeah". The best part was the look Gina and Ryan exchanged when she bagged the tux for me and he asked me "Did Gina take good care of you?" I smiled and said "Without a doubt".

I went back to the office and mom was coming out and said "You need to stop playing around with Anna and do the right thing". Where did that come from? I asked "What happened?" Mom glanced through the front window and said "She was telling me about everything she did to get you ready for this trip and I may have mentioned she would make a good wife". I stared at my shoes and exhaled. No pressure. Thanks mom. I said "Mom, I have never treated her like that, she's the one that wants things to be open and casual". Mom stared at me like mom does and I sighed and said "Okay". She kissed me and said "You know what you need to do". My heart revved and mom somehow knew and whispered "What was that?" I swallowed and lied "Nothing". Mom stared into my soul then crowded closer to whisper "There is no greater compliment any man could give me. Now, take that energy and focus it on Anna". I sighed and mom completely blew me away when she turned the tables on me and said "James Dennis Riley, if you weren't my son..."

I was still standing there frozen in shock when she winked and drove away.

I went inside and Anna was on the phone so I wrote "I love you" on a post it note and slid it across her desk. Her eyes widened, she drew in a long, deep breath, and Anna stared at me as she asked her caller "Can I put you on hold while I look into that?" She set her phone down and asked "What's this?" She was holding the post it note and I said "I don't want to be friends anymore Anna. Be my girlfriend. Come with me to Texas. Hell, move in with me". Anna stared at me for a long time then said "Yes, I can't and maybe. You don't move until I finish this call". I smiled and sat at my desk, checked my emails, made a phone call, then ordered parts for the maintenance team at one of the properties. I was putting stamps on some outgoing mail when Anna hung up the phone and asked "Can I see you in your mom's office for a second?" I should have, but I never saw it coming as I entered the office. Anna shut the door, then slammed me against the wall and kissed me furiously. She was wired and wild as she breathed "You really want me to be... for us to... are we going out?" I said "Yes. I thought you wanted to..."

Anna kissed me again and when we finally parted she gasped "Forget all that, what I want is you... us. That's what I want". I asked "You can't go to Texas with me?" Anna said "I can't JD. I have too much going on. I'll make you a deal though. If you really want me to move in, I'll do it while you're down there getting drunk and laid". I laughed and asked "What? I'm not going to get laid" but Anna put her hands on her hips and said "Don't you lie to me. It's Brian's wedding. You're going to get laid probably the entire time you're down there and I'm going to let you, because when you get home, you're mine and only mine. Have your fun, get it all out of your system, because when you get back, we start planning". I sighed and asked "Planning what?" Anna said "Oh, I see. You just randomly decided to ask me out the same day your mom and I talked about a relationship and marriage. Okay, so it's all a coincidence?" I asked "Why do you have to be so smart?" Anna said "It's a curse. I was always cute and smart. It is what it is".

We kissed some more and Anna said "You go get your refills and call me, I'll grab something for dinner and meet you at your house, I have to finish some things up here. Unlike you, I have to work to get paid". I gave Anna a dirty look and she said "Sorry, I didn't mean that and you know it. Your parents take good care of me". I asked "My parents? Hello? What about me?" Anna said "Hmmm... well, I guess we'll see. Bye... weren't you leaving?" I said "Now you're just being rude". Anna got serious and said "No. Rude would be to ask you why you smell like perfume, why your hair is messy and why you act like someone who just got laid. Knowing you just came from seeing Gina, well... what can I say. Still think I'm being rude?" I stared at Anna and said "It's not what you think. I can explain". Anna sighed and said "Why don't men realize that ‘it's not what you think' is basically a confession and ‘I can explain' means I'm guilty and trying to talk my way out of it?" I sighed and said "Tell me what I have to say or do Anna. I'm sorry and I want to make this right". Anna said "Just don't lie to me and get all this out of your system before you fly home. That's it. No meltdown or huge fight. Just get it together and buy me a ring. We've been dancing for over a year, it's time to call it".

I stared at Anna for a long time, even as she eased by me and opened mom's office door, looked to see the main office was quiet, then smiled at me. I asked "So how long have you wanted things to be serious?" Anna said "A while" and I sighed then said "No bullshit. I'll buy you a ring today and..." Anna touched my lips with her fingers and said "Don't talk about it JD. Do it. If you really love me and want this, don't tell me, show me. You're 30 and I will be soon. I don't mean to brag, but you can't do any better than me. Who else looks like I do, works her ass off, never asks for anything, and puts up with your shit?" I said "You're right. I better go look at rings today". Anna said "No, next week is fine. When you get home, you can take me and let me pick one, and maybe I'll wear that pink miniskirt you love so much". I gasped and Anna smiled then said "Yeah. In fact, I might have a surprise for you when we get home tonight if you play your cards right". I sighed and said "I better go to my doctor appointment before we have sex here in the office". Anna flirted "Wouldn't be the first time" and I sighed.

I stared at Anna and said "You are the most beautiful creature I have ever met, I love you and I want you to move in with me". Anna said "Thank you, I love you too, and I will. Now get going before I take what I want". I grinned and asked "Oh? What do you want?" Anna rubbed the bulge in my pants and said "Try me and see". I kissed Anna passionately then said "I'll see you at home" and she was smiling at me and twirling her hair when I left and went to my car. I stood there at my car but something was off, something wasn't right. I went back inside and asked "How did you know about me and Gina?" Anna said "Lot's of little signs. Kind of like the vibe you're giving off now. You want to sneak around and buy a ring and surprise me. I can read you like a book JD". I exhaled slowly and said "I'll make you a deal. From now on I'll include you in everything as long as you let me". Anna smiled until I asked "Well?" Anna smiled and said "Oh, that was an actual question? You should already have the answer". I exhaled and said "So I can seriously go down to Brian's and do whatever and then come home to you?"

Anna smiled at me with the smile a teacher gives a naughty child as she said "No. What you should do is behave like I matter most and keep it in your pants. But since I know Brian, there's no sense putting the leash on you until you get back. Then you're mine, Have your fun, get it out of your system, because when you get home, the only woman in your bed will be me". I said "Deal" and Anna smiled then sighed "It's cute how you thought you had a choice". I blinked and Anna said "Go to your doctor's appointment and I'll see you at the house". We kissed again, this time slow and romantically, then Anna pushed me towards the door and said "You can't have what I'm trying to give you if you never go to your appointment. Now get so I can finish my work". This time I left and drove to the doctor's office my family has been using since I was old enough to remember. While most practices have fancy shiny buildings and huge parking lots, Doctor Ames still practices out of the old converted house with parking for six cars at most and a hand carved wooden sign out front. Doctor Ames is my parent's age and plays golf with my father and Uncle, his wife is his nurse and my mom's closest friend. As small town as you can get, their son Charlie is the office manager and bookkeeper while his wife Carrie is both their nurse and receptionist.

I've known Charlie for 20 years at least and he met Carrie at college, brought her home, and the rest is history. Two kids and 10 years of marriage, they give me hope. Charlie checked me in and I told him about Anna. Charlie was also going to Brian's wedding and said "We can talk on the plane, but my advice is go big. It starts with little comments and off hand jokes, but eventually everyone knows you could have gotten a nicer ring if you really cared" Carrie said "I can hear you" and Charlie said "I know". Carrie is a hottie, even after two kids, and if Charlie ever gets sick of her, the line is pretty long... trust me. 30 with long black hair, Carrie is 5' 11" tall with an athletic body and curves that dare to be touched. I admit to being envious and to this day Charlie has no idea that Carrie and I made out last New Year's when we were both drunk. Carrie came into the waiting room and I gasped. Instead of her usual scrubs, she had on a short, loose, black mini skirt that barely touched her mid thigh. Black flats and a crisp white and black blouse that was unbuttoned daringly to her bra line, I could only stare.

Carrie smiled and waited as I drank in her presence and finally said "Wow". She blushed then said "I was supposed to be off today and planned to surprise whiny boy with a lunchie". I blinked and asked "Lunchie?" Charlie said "You know, a quickie at lunch? A lunchie". I blinked then said "And?" Charlie said "Mom had to go do something so Carrie stayed but I'll make it up to her, she knows it". Carrie said "Do I? Seems like you were just complaining. I think maybe I'll see if JD wants a lunchie instead". Charlie said "Go ahead". We were all silent until Charlie said "Anyways, dad is with mom, but he gave me refills for you. All you have to do is go in with hot stuff and do the usual check up things". I stared at Charlie and he said "What? If I trust anyone with my wife it's you. Besides, she has the hots for you and I'm not supposed to tell you". I gasped as Carrie blushed and looked away. Charlie said "I also know about New Year's, just so you know". I said "Well, since we're throwing each other under the bus, does your wife know about you and Anna at the pool party last month?"

Charlie was bright red and whispered "You bastard. Damn you". Carrie crowded her husband and inadvertantly pressed her hot little body against mine as she demanded "You better tell me what happened". I meant to hold Carrie's waist so that she wasn't rubbing her firm ass against the front of my slacks, but she shifted and my hands ended up on her lower hips. Carrie placed her hands atop mine and held them there as she demanded "Well?" Charlie said "We were all drunk and Anna and I woke up naked in bed. We thought we had sex while drunk and figured we were both dead anyways, so we kinda did it again. She made me swear never to tell anyone because she said JD would kill me". I tried to let go of Carrie's body but she held my hands where they were and said in a low, seething voice "I will deal with you Charles, I promise you. If I were you, I would call to make sure your will is up to date". Carrie pushed me down the hallway and into the exam room, then slammed the door. She was livid and I was worried she might blow a gasket. Instead she said with wild, angry eyes "Just get undressed and we'll get this over with".

I undressed to my socks and underwear while Carrie wrote in my file then asked "Everything feel okay?" I said "Well, I get this unusual stiffness whenever you're around and my brain fills with bad ideas, but my asthma is fine". Carrie blinked and then said quietly "You picked the wrong day to light this fuse JD. You want a shot at the goal? Take it". I stood there as Carrie reached under her skirt, pulled down light blue panties, stepped out of them, then said "Take the shot". Charlie was my closest friend and Anna just basically asked me to ask her to marry me. Plus, I just had out of nowhere sex with Gina, the hottest MILF I know. Carrie said "Okay, you need some incentive?" She moved closer to me and kissed me furiously. My body felt warm and her body pressed against mine as Carrie took my hand and slipped it under her skirt. I felt her hot, wet lips and then forgot rules of society and stripped my underwear down. Right there against the exam table, Carrie put me inside her and we started fucking in the exam room.

Was this my birthday and I didn't know it?

The moment was overwhelming and I tried to hold back, but Carrie's pussy was like a furnace and she was very tight. Carrie was also a very amorous lover and kissed me everywhere, whispered sexy things, and her hands were all over my body. I was in a whole new zone and my cock throbbed inside her as I got closer to cumming. I stroked hard, fast and deep while Carrie gasped "Fuck me" in my ear and nibbled my ear and neck. Carrie's body tightened and tensed then she sucked in a whole lot of air before moaning "Oh God..." She bit into my neck and squealed as her body shook through her orgasm and I gripped her hips as I exploded deep inside her body. We worked together as I pumped into her body and we finished at the same time, then held each other trying to catch our breath. I stared into Carrie's eyes and asked "Why?" She blushed and said "You have to promise not to be mad, especially at Anna". What? Anna? What did Anna have to do with this? Carrie said "Anna and I have been trying to figure out how to get you to... um... play around a little bit". I blinked and asked "Like swinging?" Carrie said "No. Not even like swapping. That's so 1970's. More like sharing. The four of us would just be really close and now and then... well... you know".

I pulled out of Carrie and she used a cloth to clean my cock off then wiped herself up before picking up her panties and putting them back on. All of this was a seduction? Seriously? Carrie literally handed me my clothes and helped me get dressed, then said "I really did dress like this for a lunchie with Charlie. We weren't going to talk to you about any of this until you got back from Texas. You just kind of sped things up when you told me about him and Anna. I actually didn't know about that, so I guess now we're all even if you think about it". I sighed and said "Not really. He got to see Anna naked, got to sleep with her, but I... we..." Carrie blinked rapidly then said "Oh... uh... okay. I don't know how we can squeeze it in before you two fly out tomorrow, but when you get back, I can make that happen if you really want it to. After all, they owe us if you think about it". I shook my head and said "This is giving me a headache". Carrie said "Stop thinking and let us do the thinking. You boys go down to Brian's and get laid because when you come back, it's on". I sighed. Great. Suddenly I have a fiancee... well sort of... and now apparently I was having an affair with Carrie?

Forget my birthday, did I win the lottery and not realize it?

Charlie handed me my prescription slips and said "I'll pick you up tomorrow around 9am. You got everything nailed down?" I stared at him and apparently everyone was on board with the deal but me. I sighed and said "Yeah. Thanks, I'll see you tomorrow" and I just left because Carrie was sitting on Charlie's lap kissing his neck. Nothing made sense as I drove home and sat in the driveway. Anna's SUV was parked out front and I sighed and went inside. I never got the chance to ask her about the ‘deal' with Charlie and Carrie because Anna was wearing a scorchingly sexy and very sheer negligee. Her hair was back in a ponytail, her eyes sparkled with excitement and Anna said "Hi".

.............. To be continued...