Serendipity

I woke up on the Saturday morning three days before Christmas and wondered how long I could lie there before I had to surrender the warmth of the blankets and go relieve myself. My mind wandered to last night at the bar where I once again had no luck finding someone besides myself to have sex with. I was in a ridiculous dry spell; it had been weeks since I got laid. I was startled out of my reverie by the phone ringing and cursed myself for forgetting to put it on vibrate as I picked it up and looked to see it was my Mom.

I cleared my throat and answered "Hey Mom" but I still sounded a little gravelly. I cleared my throat again and said "What's up?"

"Did I wake you honey? I'm sorry."

"I was awake, just not out of bed yet."

"Oh ok." She paused for a couple seconds and said in a lower voice "Are you alone?"

I chuckled and said "Unfortunately."

She giggled at that and got to the point. "I need some help around here to get set up for the Christmas party. Are you free later this afternoon?" I could hold it no longer and got up and walked to the bathroom, I put her on speaker and set the phone on the countertop next to the toilet.

"Yeah, I can do that. I have to go to the mall first and finish shopping." I unleashed a torrent of piss into the bowl and sighed.

"That'll work, I have...what's that noise?"

"I'm peeing."

"Nick! Didn't I teach you any manners? Jeez."

"What? It's not like you can see me. I had to go, first thing in the morning and all that."

She laughed and said "I'm surprised you could even go with your morning wood!" One time before I moved out she came into my room to wake me up and saw my morning wood tenting my boxers. She's been teasing me about it ever since. "You need to settle down and find a nice girl to help you with that."

"Right now I'd let any girl help me with that." Then I had a wicked thought and decided to try and embarrass her for a change. "You're a nice girl, you want to help me with that?"

"What the fuck Nick! You shouldn't be asking your mother things like that! What are you thinking?" I could tell by the laughter she wasn't offended, just shocked.

"I'm thinking that you're the hottest girl I know."

"Ok, now I know you're fucking with me." We both laughed and she changed the subject. "Anyway, I have errands to run too, meet here at three?"

"That sounds good, see ya then. Love you."

"Yeah, a little too much by the sound of it." She said with a chuckle. "Love you too. Bye."

That kind of flirty banter was nothing new between us. Our family was always close and could talk and joke about anything. Dad left us as soon as my Sister Mandy turned eighteen and he gave Mom a nice settlement plus paid for our college. His business did well and she got what would amount to half of its worth at the time. It was all very friendly and settled without much pain. He simply didn't want to be married to her anymore and was willing to be fair if they didn't have to fight it out in the courts. I think him not wanting to open his accounting books to the court system had a lot to do with that.

That was six years ago and my Sister has since graduated and moved to Florida for her dream job. She has always said that as soon as she could she was getting out of this city and moving somewhere warm. She landed in Tampa, twelve hundred miles and whole different climate than Chicago where we were. She was married briefly to a guy that got arrested for dealing coke, like big quantities of coke. She had no idea what was going on after several interviews the cops agreed. The whole thing was a mess and she divorced him while he was still in Hillsborough County jail awaiting trial. He got four years and she never saw him again.

I moved out a year ago after living with Mom after college to save money for a down payment on a small house. Over time our relationship has transitioned from Mom/Son to more like friends. We could confide in each other and she was the first person I would go to with a problem knowing I could get a fair point of view without judgement. Although it was awkward at first I knew I could go to her with questions about sexual things and it became nice to have a woman's perspective while I was learning the ins and outs of sex while in school. I was also always jokingly flirting with her constantly, always telling her how beautiful she was or how hot she looked in one outfit or another.

One time a couple years ago she talked to me about the flirting and asked if I was serious. I fumbled my words but said no, that I just liked to flirt with a beautiful woman and I assured her it was all in good fun. She had a strange look on her face and I felt she wanted to say more but she let it go. She seemed to have bought my explanation and I cooled it for a while so as not to make her uncomfortable, but I was lying, I'd wanted her since I was old enough to understand what want is.

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I took a shower and got ready to go to the mall to get my shopping done. I realized I was hungry but my refrigerator was pretty bare so I decided to grab a bite there. The place was crowded and I was sitting alone at a table that would seat four when I looked up and saw a lady holding her tray of food with one hand and juggling her purse and an armful of shopping bags in the other. She was very attractive and probably twenty years older than my twenty six with long dark hair hanging in a loose ponytail and a mature body that was curvy in all the right places.

I caught her eye and motioned to the three open seats at my table and she smiled and headed my way. She made her way over to me, having to weave her way around tables full of people. I admired her clothes, casual pants and a nice blouse under a long winter coat. I noticed some jewelry but no wedding ring and could sense a hint of money but she didn't flaunt it. I stood and pulled out the chair to my right, offering to help her with her bags. She took off her coat and got situated and I caught a whiff of perfume, very light and pleasant.

"Thanks, this place is so crowded today" she said and dug into her noodles of some sort.

"The pleasure is all mine, having such an attractive lady to lunch with just made my day." I replied, laying it on thick with my best smile. "I'm Nick by the way."

"Mmmm" she held up a finger for me to wait while she finished her bite of food. She swallowed and held out her hand. "I'm Claire, nice to meet you." I took her hand and looked her in the eyes, they were bright blue and sparkling with mischief.

"So Nick, are you out shopping for your girlfriend?" She had to pull her hand out of mine as I had forgotten to let go while I checked her out. I really liked what I saw; flawless skin and very light make-up that was done perfectly and a nice manicure. She was way out of my league but seemed friendly, she made eye contact right away and turned in her chair to face me.

"No, I'm recently single. How about you Claire? Are shopping for your significant other?"

"He's in Denver with family, and he's not that significant." She said with a smile. "We're more like friends with benefits, know what I mean?" She winked and then laughed. "You should see your face Nick, you'd think I was talking about sex with a complete stranger!" We both laughed at that and shared some eye contact. I liked her attitude, confident and witty and clearly enjoying whatever this little game we were playing was. She caught me off guard with that and it showed. I needed to step up my game and recover.

"Well if you need another 'friend' to fill in I'm available." I was half joking as I said it using air quotes to emphasize the 'friend'.

"Oh really?" she said with a smile. "Interesting." I watched as she looked me over, her eyes taking in my whole body. She dug back in to her noodles and we sat eating for a couple minutes. I was trying to figure out a comeback to keep this going when she looked up from her food and caught my eye again.

"Here's the deal...Nick. I've been divorced for about eight months. Twenty years with same man. So right now I'm in my 'Hoe' phase, making up for lost time so to speak. I could use another 'friend' in my life if you're interested." I loved her bluntness, she had just made a quick decision about me and wasn't afraid to say so.

"I would like that very much Claire." I replied with false bravado as my stomach was fluttering with butterflies. I mean, you read stories about situations like this but I never thought it could be real.

"Good" she said as she got her purse and rummaged around for her phone. She opened her contacts and handed it to me. "Give me your number. I'm going to my daughters' house this afternoon to wrap presents but I'm free tonight. Do you know where Sphere is? The bar on the corner of Madison and Wells?"

"I do, been there a few times." I replied. It was upscale, quirky, expensive and fun. It was a place to go if you wanted to hook up. It kind of surprised me that someone her age would hang out there.

"Can you meet me there at eight?" I nodded my head and she smiled. "Good, we can get to know each other a little and my place is close if we decide to be friends" she said using the air quotes again. She then called my number and hung up when it rang.

"There. You have my number too. Text me by seven if you get cold feet, otherwise be there on time." We talked about the weather and prices of things while we finished our food. She was very easy to talk to and the conversation flowed freely. I found out she was in real estate downtown and she also explained how she rarely went to that bar except to meet a date there, like we were to do tonight. She stood and I helped her with her coat and put mine on while she gathered her bags. She moved over next to me and whispered in my ear "Bring me some recent test results and I'll let you hit it raw, or bring your own condoms, whatever you want to do." She then kissed my cheek and walked away with confidence, her long brunette hair flowing around her. I watched as people moved out of her way and then turned back to watch her as she went by like she was a force to be reckoned with.

She disappeared into the crowd and I sat back down and exhaled. I was grinning ear to ear as I replayed the last fifteen minutes in my head. I gathered my things and made my way to my car and it seemed like I was floating on air all the way home.

I had plenty of time to wrap the presents I had just bought and set them in the pile to take to Mom's house on Christmas day. Three days to go and I was done shopping, a personal record for me. I started a load of laundry and cleaned a little, my mind constantly on Claire and what the night could bring.

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I pulled into Mom's driveway right on time and let myself in with my key. She heard me and came rushing in from the kitchen while wiping her hands on a towel. She hadn't changed since running her errands and was dressed nicely. She never left the house without looking good, something that her own Mother always insisted on. No sweat pants and a hoodie for her, even if she was just going to the corner store. She wrapped me up in a big hug and I felt her breasts crush into my chest as she laid a big kiss on my cheek.

"It's been forever, you have to come see me more often." She mock scolded me.

"It's been ten days Mom, that's hardly forever." I kissed her cheek in return and pulled back a little only to have her pull me back in and hug me tighter.

"I know" she said into my chest. "I just get lonely around here since you moved out, especially now during the holidays." I liked the feeling of her body next to mine, perhaps a little too much. I had to make sure my hips were away from her before she felt my cock filling with blood and expanding. All it takes is a hug to have all of those feelings come rushing back and having her that close affects me every time, her subtle scent and the fact that I haven't been laid lately kicked my libido into high gear.

"It's been years now Mom, you need to find a guy to hang out with." She looked at me and smiled that beautiful smile with her cute dimples.

"That's what I have you for silly! You should hang with your Mom so she doesn't get lonely." We broke apart and I saw her briefly look at my crotch as if to confirm the effect she has on me. She didn't look back at my face but I saw a grin on hers as she spun around and headed for the living room. My eyes were glued to her shapely ass as she said "Come on, I'll show you what needs to be done."

"We need to move the sofa off to the side and the recliners over here." She said while pointing here and there. "I bought a poker table and chairs so we can play in here instead of in the kitchen." Poker was a yearly tradition after we were done eating Christmas dinner.

"Ok" I said and started unplugging the lamps and getting things ready to move.

"Let me go change out of these clothes and I'll help. Get yourself something to drink, I'll be right back." I stopped what I was doing and went to the refrigerator and grabbed a bottle of water. I looked around and admired her Christmas decorations, they were never the same each year and always looked great. I heard her coming back and got to the living room just in time to watch her bounce down the last couple stairs. She had changed into leggings and a loose fitting oversized tee shirt and it was obvious she didn't have a bra on judging by the way her thirty six C's were swaying to and fro. Her nipples were poking through the fabric and she caught me staring as she walked by with that same grin on her face. I tried not to stare too long at her ass in those leggings.

"C'mon kiddo, let's get to work." She smirked and we got to it. Every time she bent over her top drooped down and I got a good look at her tits almost to the nipples. She was driving me nuts and I began to wonder if it was on purpose. It took a half hour to finish what she wanted then we sat at the kitchen table to rest.

"So it's Saturday night, any big plans?" she asked.

"As a matter of fact yes" I replied and told her the story about meeting a lady at the mall. She looked shocked as I told her the comment about hitting it raw.

"You gotta be shittin' me!" She said while laughing. "Be careful, if I was you I'd take condoms."

"I plan to, we'll see how the night goes. It's all a bit crazy ya know?"

"Yes it is, you'll have to call me in the morning and let me know how it went."

"Will do. I'd better be going, I have to get ready." We stood up and she wrapped me up in another big hug, this time her braless tits felt wonderful against me and I took in the smell of her body wash mixed with her natural scent. We held each other for a long minute then she looked up at me and gave me a quick kiss on the lips. It was rare for her to do that and it kind of shocked me.

"Wow, what was that for?" I asked with a smile.

"For being here when I need you sweetie. I can always count on you." I looked at her as she smiled that huge smile of hers and felt my heart flutter. Something passed between us in that moment as we looked into each other's eyes. I felt my cock tingling as I looked at her and drew her back in for another hug.

"I'll always be here for you Mom, I love you." She pressed her whole body into mine this time and we held each other for a bit. She's only a couple inches shorter than my five foot nine and fit into my arms perfectly. I ran my hand up and down her back a couple times and she squeezed me tighter, I could feel her breath on my neck and it was arousing. I was starting to get hard and I know she felt it, and then she slowly pushed off me and took a step back. I couldn't help but look down at her nipples that were hard as pebbles and poking through her shirt.

She noticed where I was looking and said "Eyes up here buddy." When I looked up I could see that she was blushing so much even her neck was red. We held a look for a few seconds, neither of us smiling and her eyes were searching mine for the answer to a question that hadn't been asked. I was at a loss for words and she started to say something then stopped. The silence was starting to get awkward when she turned and headed for the stairs. She muttered "Call me tomorrow" and rushed upstairs. I let myself out and drove home wondering if she wanted me as much as I did her, and could I even bring myself to make a move.

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Claire was sitting at the bar when I got to the club ten minutes early. She was talking to a guy that was standing next to her when she saw me then looked at him and said "He's here, nice meeting you." He turned and walked away none too happy and I slid into the space he had just left.

"Hi Nick, I'm so glad to see you!" She stood to meet me and gave me a tight hug whispering in my ear "He was getting on my nerves, I told him I was waiting on someone but he wouldn't leave. Ugh."

"Well I can't blame him for trying, I mean look at you. You look amazing." She was wearing an almost transparent white top and I could faintly see her white bra underneath. Being winter in Chicago long pants were in order and she had on a pair of skin tight stretchy brown jeans that accentuated her bubble butt perfectly. Her long hair was up in a messy bun with a curly tendril framing each side of her beautiful face. A couple of rings with a tasteful necklace and a matching bracelet completed the look. She had put some effort into looking good for me and I couldn't believe my luck.

"Aww thanks, you're lookin' pretty good yourself." She had probably given me the once over while I was doing the same to her. I knew there was an informal dress code here so I had on a nice button down shirt and my best pair of black jeans and decent shoes. No tee shirts or gym shoes allowed here.

I took off my coat and draped it over the back of the stool. We sat down just as the bartender walked up and asked what I wanted. "I'd like a rum and coke and one more of what the lady is drinking." I replied while pointing to her almost empty glass.

"Chivas and water" she reminded him then swiveled on her stool to face me, putting her legs on either side of my left leg and inching closer. "So Nick, did you think about me today?" She set her hand on top of mine that was resting on my leg and ran a finger up and down the back of it.

"Only all afternoon." I lied, knowing that it was my mother that held my thoughts just as much as her. "I'm still having a hard time believing I'm sitting here with such a beautiful woman." She smiled at that and picked up her drink, finishing it with one swallow just in time for the bartender to bring the fresh ones.

I reached for my wallet but she signaled for me to stop. "Just put them on my tab" she told him. Looking back to me she said "Drinks are on me tonight, although if I get my way there won't be many of them before we get out of here."

"Yeah, I don't want to be too drunk when you have your way with me." That cracked her up and we laughed. She moved closer yet and trapped my leg between hers.

She leaned in and whispered "I'll expect the same amount of effort from you young man, I like a nice hard fuck once we get going." I was again impressed with her directness. I wasn't used to not having to work to get laid.

"I'll do my best to service you well madam." Another round of laughter and we finished our drinks talking about more mundane things. I found out her daughter is the same age as me and recently married and excited about hosting Christmas at her new house. I filled her in on my family and we made small talk until my second drink and her third was empty.

"Ok dude, I'm calmed down now, you weren't the only one who was nervous." That kind of surprised me, she hid it well. "How about we go to my place. It's only three blocks from here. Did you drive?"

"No, I Ubered, I wasn't sure about parking at your place and I don't drive when I'm buzzed."