Wedding Hooup with Former Neighbor

This is story #19 of my series about my post-marital sexual journey. Read the first story (Babysitter Lauren) or my profile, for any background needed. You may see references to prior stories/people, but for the most part each story stands on its own.

Not everyone likes me or my stories. That's OK.

I enjoy all comments

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Sherry

Right after I got married in the mid 90's, my then wife Caitlin and I rented a condo in a small building. Our neighbors right next door with whom we shared a patio space were named Pat and Sherry. We were 27 at the time, Pat and Sherry a bit younger, around 22. Neither of us had kids yet.

We met and got along fine, although Pat was a bit of a douchebag. I frankly just didn't like him; and if we weren't neighbors, or if he wasn't married to Sherry, I wouldn't give him the time of day.

Sherry was a delight, however, and I adored her. I was always happy to spend time with them even though Pat was a dick. Pat would frequently make inappropriate comments to or about Sherry and occasionally Caitlin, and more than once I had to shut him down. I never did the same, because I'm not like that, and I had too much respect for Sherry to do anything like that. Sherry was clearly embarrassed by his boorish behavior.

Sherry and Pat got pregnant within about four months of us moving in, and they had two kids pretty quickly, then moved away to a four-bedroom home in the suburbs. They invited us over a couple times, and we went, but we just grew tired of them. Well, tired of Pat. Sherry continued to be a treasure.

Sherry reminded me of a brunette Pamela Anderson. Same facial features and smile, nice big tits and a killer ass. Her body survived the two childbirths quite well, and whenever I saw her, she looked great.

We lost touch over the years, and none of us exchanged cell phone numbers since cell phones weren't really a big thing then.

After Caitlin and I split in 2010, I joined social media. Pat immediately friended me, then sent me a message that he and Sherry divorced several years before. She blamed him for being an asshole, he blamed her for being a bitch, yada yada yada. I learned from him that she and the kids moved about five hours away, back to New York where Sherry grew up, and he rarely saw them. I didn't give him much thought beyond that.

I searched Sherry on social media, but I guess she wasn't on yet, and I wasn't able to find any contact information for her. The internet at that time wasn't nearly what it later became, so it wasn't real easy to find someone that didn't want to be found.

Fast forward another two years.

In southern Virginia there are several swanky resorts. You know the type- golf courses, spas, expensive wines etc. My company at the time scheduled a weekend retreat at one of these places every year, a combination business meeting and bonding time.

I went out a night early, on a Thursday night, since I was single and my kids were with their mom that weekend. I figured I'd get a jump on traffic and enjoy some solitude before everyone came out to golf and drink on the company dime.

As I was having a drink at one of the bars on Thursday after dinner, in walked Sherry. I hadn't seen her in quite a few years, but I recognized her right away. Her gorgeous Pamela Anderson-like face, and her generous tits and ass, having grown just slightly but still shapely, were impossible to miss.

She recognized me immediately as well, and we hugged, each of us happy to see the other after so many years. She sat with me and we had another drink, catching up on the last few lost years.

Sherry was very sweet. Not naïve in any sense of the word, quite the opposite. Very smart and successful, running a non-profit that did environmental research, kind of a Save the Whales type of group. But she had a very soft edge, versus the kind of bitchy, hard edge that many successful women had in modern times. I thought it impossible to be mean or rude to Sherry in any possible way.

Turns out that Sherry was at the resort because her oldest daughter was getting married there that weekend. This resort was a popular wedding venue for many southern girls, and I guess her daughter never lost those southern roots even though they moved back north when she was a kid.

Sherry had come out a night early to make sure that everything was in order -- rehearsal dinner, flowers, wedding space, cocktail hour, dinner space, food etc. Her daughter didn't want any glitches, so Sherry came out to make sure things were in order before anyone else arrived on Friday.

Sherry was half-heartedly committed to someone, a wealthy guy who travelled on business quite a bit, and she hadn't seen him in months. He had proposed about a year before, and she answered with a kind of "let's wait and see" half-answer. He had cancelled on her as her date just a few days before the wedding, claiming to have been stuck in whatever location he was currently in.

Normally, she explained, this wouldn't be an issue, but of course her ex-husband Pat would be attending, and word had it that he had a new girlfriend and would be showing her off. Sherry was dreading the spectacle that Pat would make of himself, but she was determined to get through it with a smile for the sake of her daughter.

We laughed and had a great time for about an hour. Slightly flirtatious but nothing overly obvious that I wanted to fuck her in the worst way. My mind was racing with the possibilities of what I would do with her heavenly body.

Around 8:30, Sherry excused herself, saying that she needed to take a shower since she had had a spa treatment that day and was covered in scented oils.

I had smelled the oil on her when we first hugged, so I commented, "Don't wash it all off - You smell delicious, and you look fantastic."

Her smile in response was just a slightly different type of smile, kind of a like she had a secret. It was clear that she appreciated that comment.

We exchanged numbers, and I offered for her to call me at any time over the weekend if she needed moral support or whatever. I could easily excuse myself from any activity or meeting if needed.

Around 10:00 that night, my phone buzzed. I was just about asleep, but thinking it might be one of my kids with a problem, I looked at my phone.

It was Sherry.

"Hi," her text said. "What are you doing?"

"Just lounging in bed, you?"

"Same, kind of bored. You want some company?"

"Sure, c'mon down; the door will be unlocked."

"Great!" she responded. "Be there soon," and she added a winking emoji.

I was thrilled at this turn of events, but still a bit unsure how to play it. I had about thirty seconds to decide, so I opted for the bold move.

I figured that the odds were pretty good that she was coming for something other than more conversation. I mean we were friendly, but certainly not close friends, and for her to invite herself to my hotel room at 10:00 at night seemed rather telling as to why she was coming to visit me. She wouldn't be so naïve as to not see how this would be interpreted.

A minute or so later, Sherry appeared in my doorway. The front portion of my room was pretty dark, but for a night light glowing in the bathroom.

"Phil?" she asked, making sure she was in the right room.

"Yep, I'm here," I answered.

I heard the door close and Sherry engage all the locks. She walked into the bedroom area and stood next to my bed. I had a small desk lamp on for some minimal lighting.

The moment of truth had arrived.

I was in bed with just the sheet over me, and I was very obviously stroking my cock. She stood, watching me wordlessly for at least a full minute. Then she reached forward to pull the sheet off of me.

Sherry gasped when she saw my cock, the big mushroom head peeking through my fist as I stroked myself. I watched her face as she watched me masturbate, and then her eyes met mine.

She was wearing a silk pajama top and matching shorts. She began to unbutton the top slowly, and her magnificent tits popped into view when all the buttons were undone. She peeled the top off and rubbed her tits, squeezing them together with both hands, our eyes still locked.

My eyes dropped briefly to her waist; my message clear. Sherry let her tits fall from her hands and pulled her shorts and panties off, revealing a small black bush.

Now standing fully naked before me, Sherry watched as I released my grip on my dick. It stood tall in the air and throbbed. Sherry was mesmerized by it, watching it bob in the air.

No words spoken, Sherry climbed onto the bed and straddled me. She grabbed my cock in her hands and placed it at the opening of her pussy, then slowly sunk down on it. Her eyes rolled back in her head as she slid down the length of my shaft, our pelvic bones eventually meeting as she reached maximum depth.

Sherry sat straight up on me and I took in the sight of her glorious breasts, her chest heaving as she grinded her pussy against me, alternating between small circles, then back and forth. After several minutes, Sherry's head flew back and her mouth opened, and I could tell she was coming.

After she came down, Sherry got up onto the balls of her feet and rode me in the squat position. With her hands on my chest, she rode me up and down, faster and faster. I rarely come with the woman on top, and I typically have significant stamina, but the squat is a game changer. Within just a minute or two, I reached my climax, pulling her down and holding her there while I deposited my load into her.

I held her there until I was done, then released the downward pressure on her. Still holding her hips, I pulled her toward my head. She seemed confused at first, but my insistent pulling finally got the message through. With my hands now on her ass, I helped her move toward me and plant her sloppy pussy on my face.

I softly licked the outside of her pussy, then used my tongue to penetrate her, scooping wads of cum out of her and relishing in the sweet nectar of our combined fluids. Sherry was holding onto the headboard of the bed, using it for leverage as she ground her hips and moved her pussy back and forth on my face.

The intensity of her movements increased, and moments later her movements stopped as she forced herself down on me with all her weight and shuddered, a heavy sigh escaping her lips as she orgasmed once again.

Sherry sat still on me as she recovered from her orgasm. Then she rolled off of me, laid down next to me and we kissed sensuously, sharing the aftertaste of the creampie I had just eaten.

She then wiped my wet face with her hand, threw her arm around my chest, and whispered, "Thank you," in my ear, the only words spoken during the whole encounter.

A minute later, she was asleep.

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I eventually drifted off as well, after my heartrate came down and my brain processed what had happened. When I woke up maybe around midnight, it took me a minute to remember that Sherry was in my bed. But once I did, I looked over and could see in the faint light that she was laying on her stomach.

Sherry always had a great ass. Not small and tight, even before kids, but a little bigger than the norm. The shape was exquisite, and having babies widened her hips and filled out her ass proportionately, so her ass was still perfectly shaped, just slightly bigger than it was.

We were both under the sheet, so I reached over and began rubbing the round globes of her ass. After a minute or so, I don't know whether she was awake at this point or not, but her hips began to rise and fall with my strokes along her ass.

As my fingers crept closer and closer into the crack, her hips rose further, allowing me access to her cunt. I fingered her from behind, feeling her pussy still a bit sloppy from my earlier load.

My cock was hard in no time. I mounted Sherry as she lay prone on the bed. Straddling the backs of her thighs, I positioned my cock between her legs. Her hips rose again as I thrust forward, and I could feel the head of my cock pop into her vagina.

No doubt she was awake now, as I heard her groan at the sudden intrusion.

"Yes," she hissed as her fists gripped the pillows.

My movements were forceful and steady, changing angles slightly with every dozen thrusts to mix up the friction. Sherry gripped the pillows tighter and tighter, the thin fabric entwined between her fingers. I pounded her over and over like this, ultimately holding her down by her shoulder blades and forcing her face into the pillows.

Our sex was intense, but again, very few words spoken.

"Take my cum," I said as I thrust forward one final time. Sherry shook with her own orgasm as I buried myself deeply within her, filling her again.

I held still within her, my cock eventually softening and falling out of her with a wet plop. I gave her ass a very light, playful slap as I rolled off of her, and we laid still and silent, eventually drifting off to sleep again.

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I'm usually an early riser, between 5:00 and 6:00 a.m. I didn't know about Sherry or what her plans were for the morning. I had to be at my company meeting by 8:00 a.m.

I was pretty much awake when Sherry got out of bed and went into the bathroom just before 6:00 a.m. I didn't know if she was just using the restroom or what, but within a minute I heard the shower running.

Figuring she was awake for the day, I called room service for some coffee and yogurt with fruit, and requested a toothbrush for Sherry since she didn't bring anything with her when she came over the night before. They promised to send it right away since we were the first order of the day.

The coffee arrived within just a few minutes. Sherry came out of the bathroom just as I was pouring the coffee. She had on a resort robe, her hair slightly wet.

"Coffee?" I asked.

"Yes please, you're a life saver! Cream and sugar please."

We sipped our coffee quietly, the morning news on in the background as we also ate the fruit and yogurt.

Watching me eat fruit, Sherry said, "Did you know that food can affect the taste of a guy's semen? Yours would probably be sweet later today since you're eating that fruit."

"Interesting," I replied. "No, I didn't know that. I wonder how we could test that theory."

"Yes," she said with a smile. "I wonder."

"What does your day look like?" I asked.

"My morning is open. People should start checking in around mid-afternoon. We have the rehearsal at 4:30, then dinner at 6:00. I'll just be helping to get people settled and making sure that everything runs smoothly. What about you?"

I answered, "I have this meeting 8:00 until Noon-ish, then lunch. Then we are shooting sporting clays at the range for anyone that wants to do that. Then we have our own dinner around 6:00 as well, probably in the same dining room as you."

"Do you mind if I just lounge around here this morning? My room has two double beds, and your king is just so cozy and comfy."

"Of course, that's fine." I tossed her a toothbrush. "Housekeeping brought this for you."

She smiled as she walked toward the bathroom with it.

"My hero!" she said with a laugh.

When Sherry was done in the bathroom, I jumped into the shower and got myself cleaned up. It was still only 7:00 a.m. when I walked out, and Sherry was reclined on the bed watching a morning talk show, still in her robe, which had started to fall open just a little bit, her right breast almost visible to me.

I grabbed the remote from the night stand and shut off the TV. Sherry looked at me and immediately understood why I had done that. I had dropped my towel on the floor and stood naked before her, my cock rising as I looked at her tits.

"I want that cock in my mouth" she said, her arousal evident in her voice.

"Lay flat," I told her.

Sherry scooted down off of the pillows and was lying flat on her back.

I straddled her head, resting on one knee and one foot on each side of her face. She opened her mouth like a baby bird waiting for dinner, and I dropped my balls into her mouth, a classic tea bag.

My balls are quite big and they hang down substantially, but Sherry was up to the task. She sucked my balls into her mouth as I rubbed my hard cock on her face, then she pushed them out and licked them all around, even getting down and licking my 'taint area.

A few minutes of this, and I shifted my position so that Sherry could lick and suck the shaft of my cock. Watching me, she did just that, pursing her lips and running them up and down the front of my shaft.

A large drop of precum had formed on the tip of my dick, so I pulled back just slightly away from her. We watched together as the precum slowly fell from my cock head, right into her waiting mouth.

Sherry groaned as the sweet/salty substance hit her tongue, and she pulled me to her, now licking the rim, kissing the head, and milking my shaft in an attempt to squeeze more precum out of me. She was rewarded with several more drops, which she eagerly licked up.

Readers of any of my prior stories know that I have a sexually dominant personality, and typically I get a bit on the rough side. Sometimes I take a different tact depending on the person and the situation.

With Sherry, I wasn't quite ready to make this move, though I sensed that she would react favorably to it. Most strong, independent, successful women have a tendency to be submissive in the bedroom, as a means of escape from the pressures of day-to-day life, kind of a sexual alter ego. But my regard for Sherry held me back for the time being. I knew she was no prude - her sucking my balls and licking my taint evidence of that - and obviously she wasn't opposed to anything we had done to date. But given how much I revered her, I just felt the need to hold back a bit.

So, I refrained from ramming my cock down her throat and facefucking her, for now. Instead, I watched her pleasure me, and sensed that she was fingering herself as she did so. I looked back to confirm that she was indeed diddling her clit as she licked my head and shaft.

Knowing we were short on time, I moved down her body and and positioned myself between her legs. Grabbing her with my hands on the back of her knees, I spread her open wide. Placing the head of my cock at her opening, I slid it up and down the length of her cunt for a few strokes.

Then, our eyes connecting, Sherry whispered a throaty "fuck me."

I slid the entire length in, not forcefully, but in one smooth motion.

Sherry's eyes rolled back, and her neck arched backwards as her mouth opened in a silent groan. My thrusts again were forceful and steady, and I alternated positions and angles frequently. Her gorgeous tits captivated me as they bounced around in time with my thrusts. Sherry caught me watching them, and used her fingers to pinch her nipples as my assault on her pussy continued.

As I felt my orgasm building, I grabbed Sherry's feet and spread her legs wide, then placed the soles of her feet flat against my chest. Leaning forward with my hands on the backs of her thighs, I had her in a very open and vulnerable position.

Sherry looked at me with those brown eyes and whispered, "oh yes, fuck me, fuck that pussy. Give me your cum," and that was all it took.

A dozen steady thrusts later and I was depositing yet another load into Sherry's now well-used pussy.

"Oh God, I can feel it," she said breathlessly as my typically big morning load splashed her inner walls.

When I was spent, I pulled out and once again slid down her body to get face to face with her freshly fucked pussy. My cum was abundant, and I placed my lips against hers and sucked out as much cum as I could.

"Mmmm yes, clean up my sloppy pussy, suck that cum and share it with me," Sherry moaned.

With a mouthful of cum, I worked my way back up her body and moved in to kiss her. Sherry attacked my mouth like she was starving, our tongues exchanging cum in a sloppy kiss that I'll always remember. Sherry groaned as our kiss continued, and I could feel her hand working her pussy as we kissed.