New England Cheating Wife

This is Part 1 of Story # 45 of my series about my post-marital sexual journey.

If you want any background on me and how I got here, you can read the very first story I published (Babysitter Lauren) or my author's profile, and go from there. Each of my stories is published in chronological order

You may also see references to prior stories/people, but each story stands on its own and reading prior stories isn't necessary for understanding this one.

Not everyone likes me or my stories. That's OK. My writing style, and my sexual style, isn't everyone's cup of tea.

I enjoy all comments and welcome any private feedback

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Author's Note - trying something different here - writing from alternating perspectives. Hope it works for you.

Him:

In the weeks after a mini-vacation that I took with my daughter and her friend, and her friend's mom Wendy (see prior story series -- Vacation Affair) in the Fall, I didn't hear from Wendy at all. We had discussed our feelings for each other and what things might look like when we got home, but she had to decide when/if/how to leave her husband and her marriage, and asked me not to contact her. Weeks went by and nothing, so I started to get the feeling that our fling was just that -- a fling of opportunity.

As the holidays approached and my ex-wife planned to spend some time away with our daughters, I decided to leave the chill winter air of southern Virginia and escape to some sunshine. I booked a couple nights at a swanky resort in Miami and looked forward to some solo time.

Sex was on my mind to some extent. It had been over two months since the trip with Wendy, and I sat still since we got home. My main goal was to relax, and if I happened to get lucky, great, but I wasn't on a mission to get laid.

I checked into my resort- my home for the next few days. I went fishing, jet skiing, parasailing; played golf, went to clubs and chilled out on the beach. There were a lot of ladies there of course -- everything from young, hard-bodied wanna-be models, to older MILFs, and everything in between. I caught some glances, but I was afraid of hooking up and then having someone hanging on me the rest of the trip.

My last full day, I was looking out my window down into the pool area below. There were several people there in the mid-afternoon sun, maybe a dozen or so couples and a few singles, and the pool bar was getting ready to open for the night. My cock stirred as I looked at some of the ladies there by the pool, including one in particular. I decided to go check it, and her, out.

Her:

I'm Jen, a former yoga instructor turned housewife, living in New England.

An exhausting, busy summer, followed by an insane fall with back to school, club soccer and the parent-teacher association had wiped me out. Here I was, a 44-year-old stay at home mom of two active kids. Every day was running running running. My husband worked a lot, and though he was a good provider, I was in charge of the kids and the house and the dog and everything. It is exhausting!

Finally, one day, I decided that I needed a break. My husband had amassed some frequent flier miles from work, and since they were transferrable, I let him know that I was taking a trip between Christmas and New Years. He resisted at first - I had never travelled without him, though he did all the time for work -- but I insisted that I need some solo time to recharge my batteries.

I had never been to Florida, so I booked a room at a nice resort in South Beach. Sitting on the beach alone sipping wine for a couple days sounded like heaven!

I checked into my room and started to put my bikini on. The sign in the lobby said the pool bar opened at 4, and I thought to myself, "I need a stiff one."

That thought jolted me into a realization that I hadn't had a real "stiff one" in a long time. My husband hadn't fucked me in years. Our life was like a roommate situation. We got along fine and everything was good financially and health wise. But years of the daily routine had taken the spark out of our relationship, so for the past five years we have just been basically friends who live together.

I'm in great shape -- 5'6", about 130 pounds. Green eyes, brown hair down past my shoulders, B+ sized tits and a tight ass from yoga. Shame it was going to waste.

My pussy began to throb as I thought about how much I used to love a hard cock in me daily. I made a mental note to find the nearest drug store and grab a toy so that I could get myself off over the weekend.

With those thoughts in my head, I made my way to the pool, laid in a lounge chair and kept an eye on the time, finally wandering over to the bar as the bartender opened the wooden hatches and prepared to open for the day.

As I sat down, a tall man in a gray tank top approached the bar as well. He took a seat about ten feet from me and casually glanced my way. He was definitely hot, but something about him was a little off putting. Like he thought he was God's gift to humanity and did whatever he wanted. Probably an unfair first impression, but he just gave off that vibe.

I saw him checking me out through his sunglasses, and the thought of that sent a chill up my spine and back down right to my pussy. My clit tingled as I realized that I had caught a man's attention, even though I had no intention of doing anything about it. My nipples hardened, but I made no move to cover myself and let him know that I knew I was getting aroused.

Him:

I made my way down to the pool area wearing a tank top, swim trunks, and flip-flops. A hat and dark shades complete my outfit, and I walked up to the bar just as a young man opened the wooden gates to reveal a makeshift tiki bar.

The woman I had spied from my window was there as well, obviously waiting for the bar to open, and was sitting on a bar stool waiting rather impatiently for the bartender to take her order.

I took stock of her -- probably 10 years younger than me- I put her at early forties. Great body. A yellow bikini favored her figure well -- nice round and full tits, probably a C-cup, and they stood proudly. Long, firm legs that looked like they'd been out of the sun too long and were now in danger of burning after several hours in the Florida sun. Her stomach was flat, and she looked like she spent time caring for her body and her skin. Her toes were painted in a bright "fuck me" red. I knew from my hotel window that she had a nice round and tight ass as well. All capped off with brown hair in a pony tail to the middle of her back. Very sexy.

I noticed a wedding ring, but no husband that I had seen either from the window or now at the bar. She looked like she was happy to be alone and I surmised that she was either on a gals weekend or a solo trip. But from the lack of companionship, the obvious choice was solo.

My further assumption was that she wanted to get away from her home life for a short spell, and that the grind of day-to-day life had pushed her to this paradise for a few days of decompression. Without a husband in tow, that also likely meant that the romance was gone, otherwise they'd be here together fucking like bunnies while the kids stayed home with grandma.

Her nipples hardened under the thin material of her bikini, and it was obvious that she knew I was checking her out.

And she liked it.

Finally, the young bar keep turned his attention to the woman, but I quickly interrupted and took control of the situation.

"Grey goose and soda, lemon and lime. Doubles in a tall glass. Two of them. One for me and one for the young lady."

Her:

"Who does this fucking guy think he is?" I thought silently. "Gets here after me, checks me out, jumps ahead of me in line, and then presumes to order my drink. What an asshole."

But, I was powerless to say anything. I simply murmured a weak "thank you" then counted the seconds until my drink came so I could get the hell out of there and away from this guy. He ignored me after ordering, checking his apple watch and reading a text or email. The bartender set my drink in front of me. I grabbed it with two hands and got up to leave.

"You're welcome," I heard him say as I turned from the bar.

I simply turned toward him with an awkward smile as I ran from the bar.

The day was now scorching hot, and the interaction with this strange man had me sweating bullets. I made my way to the steps of the pool and walked in. When the cool water hit me between the legs, I swear I had a mini orgasm, the water immediately impacting the hot wetness between my legs.

I waded over to the far wall and set my drink down, facing out of the pool while my ass faced the bar I had just escaped from. I looked around as my breath settled, taking note of about six couples around the pool in lounge chairs, and another six or eight in the pool. All seemed to be coupled up, minding their own business.

Except me and the man who bought me the drink.

Finally I turned my head back toward the bar to sneak a peek, but he wasn't there. I breathed a sigh of relief, but as I turned my head back, there he was, in the pool with me. Right next to me!

He was leaning back against the wall of the pool, the water level right just above his waist, facing the opposite way, my stomach against the pool ledge and my drink resting on the pool deck.

I looked up at him- he was a good foot taller than me- and I knew from the look in his eyes that things were about to change. As much as I was put off by his cockiness, at the same time I felt helpless.

He reached up and cradled my chin, then slowly slid his hand down my neck to my chest. I was paralyzed. With his middle finger, he slipped inside my bikini top and ran his finger along my nipple. I gasped as he touched me, the first man other than my husband to do so in over 20 years.

Still staring into my eyes, he removed his finger from inside my top, and then pulled the top down under my tits, exposing both of them to the hot summer air. I had never been one to expose myself, but under the current circumstances, for some reason I was turned on beyond belief. Despite the warmth of the day, my nipples were rock hard under his gaze as his eyes dropped to look at me.

"You're wet, aren't you?" he asked, knowing the answer full well.

I tried to resist more.

"Wouldn't you like to know. You think getting publicly groped by a stranger turns me on?"

He nodded, not fooled by my false bravado.

My tits now out in the open for all to see, he slipped his hand into the front of my bikini bottoms, feeling the light strip of hair that I left behind when I shaved that morning.

I gasped, and my brain begged my body to slap his hands away and scream for help.

"What are you doing?" I asked. "I'm married, and there's people all over the place."

Ignoring me, he said, "You're a slut aren't you? I'll bet you were a real whore in your younger days. Getting fingered and giving blow jobs under the bleachers, getting fucked in the backseat of the quarterback's car. But now you're married and proper, but the slut is still in there, isn't she?"

"Fuck this guy" I thought. "Who is he to talk to me this way."

But my actions again contradicted my thoughts. He was right, and I bit my lipped as I nodded at him.

Him:

I knew I had her. She was a classic case of former slut gone good girl, but now years of sexual frustration, coupled with being away from home where no one knew her, was a perfect recipe for letting her repressed cock slut come out.

I felt the meaty flesh of her labia, engorged and hot. I reached between her legs with my entire palm, then grabbed her pussy lips with my fist. I squeezed, hard, feeling the skin of her labia being pinched between my fingers.

The pain must have been terrible, but her eyes still showed a flicker or resistance. I squeezed harder, finally watching her face drain of all will to resist further.

Once she submitted to me, I slipped a finger into her wet cunt, then added a second, jamming them up inside her as far as I could, and flicked her clit with my thumb. She began to tremble and moan, while trying to remain cool for the others around the pool. If anyone was paying attention, they would see what was happening, but very likely no one was.

But I wanted people to notice.

"Come for me, slut," I ordered, loud enough that others nearby would hear.

Sure enough, several heads turned in our direction, and my mystery woman looked at them with shame. That shame was enough to push her over the edge, and she let out a loud moan as she reached her peak, her pussy convulsing and spasming around my fingers.

"Oh God, yes, oh fuck, I'm coming," she ground loudly.

She shuddered as her orgasm gripped her, fingernails digging into my arm sharply, eyes closed, mouth open and head thrown back.

She slowly came down, opened her eyes and looked at me as if in a trance, then suddenly realized where she was as she noticed several people looking at her with big smiles. She quickly pulled back, my hand falling from her bikini bottom as she adjusted her top to cover her gorgeous tits.

She looked at me, her eyes a combination of continued arousal and silent anger.

Before she could say anything, I said "you're welcome, again."

I slowly exited the pool and took my place on a nearby lounge chair, on the other side of the pool from where she had been sitting. She held her head high and did the same, as the crowd murmured in realization that we weren't there together.

Her:

Oh God I was so embarrassed! Half the people in the pool area just watched me get fingered to an orgasm in the pool, and now they knew we weren't even together! My large wedding ring glistened in the sun as I walked to my lounge chair, trying to pretend that everything was normal, while the stranger that just violated me sat in his own chair, not a care in the world.

I didn't even know his name, nor he mine. He hadn't even asked!

I sat in my chair stewing, trying to figure out how long I had to remain before I could leave. If I ran out right out, it would be obvious that I was ashamed, and I couldn't do that.

So, I sat there for a full hour, looking at a book but not seeing the words. Only replaying in my head the feeling I had as this man touched me and fingered me, easily making me come.

After an hour, I had the nerve to look up. The man was gone, and the pool crowd was focused on themselves and their partners. No one cared about me again, so it was safe to leave the pool without shame.

I ran back to my room and laid on my bed, breathless as I alternated between feeling violated and feeling as turned on as I ever remembered. Before I knew it, my bikini was on the floor, I was rubbing my tits and pinching my nipples with one hand while I buried two fingers in my pussy with my other hand, reliving the scene at the pool just an hour before.

I came with a groan, sticky fluid covering my hand as my orgasm pulsed through me like it hadn't in over a decade.

I flopped back on the bed, and as I recovered, I hoped that this would be the end of it. My needs now being satisfied with two intense orgasms.

But as the minutes passed, I knew that wasn't going to be the case.

Him:

I went back to my room and took a quick nap and shower, then around 7:00, I found my way down to the resort restaurant and bar.

The bar and restaurant were in the same room, but separated by a light curtain. You could see the shape of people on the other side -- their heads and bodies, but not their faces. The bar was shaped like a semi-circle, so I found a spot at the very back, in semi darkness. Several couples were enjoying a quiet meal, and from my position I could see out to the people eating, but was kind of secluded from the restaurant. I ordered a glass of wine.

And waited.

I waited for my mystery woman. I knew that she'd come looking.

Sure enough, at 7:30, she walked in. She pretended to not be looking for me. But I knew she was, and when she spotted me alone at the bar, we made eye contact, and she gingerly made her way over and took a seat with a stool in between us. The bartender walked over and took her drink order, and she sat there as if we were strangers.

"Come sit next to me," I said.

Her eyes showed a mixture of resistance and submission.

"Don't make me tell you again," I said sternly.

She looked down, her submission taking over. She slid over and was now sitting at the stool next to me in the dark corner of the bar. The bartender was on the other side, fixing drinks for the waitresses, and we had the place to ourselves for the moment.

"Tell me why you're here. Here with me."

"I don't know. I shouldn't be. I came here because I needed to get away from my life for a little bit, just to relax. But now, I don't know, I need to let go, and be who I used to be if only for a little while."

"And who did you used to be?" I asked.

"A slut. I would let boys do whatever they wanted to me. And I loved it."

"Put your hand on my leg," I told her, and she complied, resting her right hand on my left thigh as she faced me.

Slowly her hand crept forward, under the leg of my shorts, until she found my cock and balls resting. I began to get hard as she fondled me, and within a minute or two, I had reached full hardness in my pants.

She stroked me with purpose, our eyes locked together as she pumped, pausing occasionally to cup and gently squeeze my balls.

"You want my cock, don't you?" I asked.

She bit her lip and nodded slowly.

I looked at her and said "you made me hard today and didn't do anything about it."

"I'm sorry, "she whispered.

I moved my hands to my waist and unsnapped my shorts, then pulled my zipper down.

"Right here?! Now?!" She asked with worry, looking around to see if anyone was around.

"Here and now, or never," I answered.

I lowered my shorts to my knees, my cock springing fully upright since she had been fondling me for a few minutes before.

"Oh my God," she gasped as I was exposed to her.

Reaching out with both hands, she gripped my shaft tight and squeezed it. A drop of precum had already formed from the handjob, and it rolled down my cock head and coated her hand.

She leaned forward and extended her tongue, and took a long lick of the salty fluid.

"Mmmmm," she groaned as she licked her lips.

She was hot, and I love some cock worship, but this was not the time or place. I placed a hand in her hair and gently pulled her head back to look at me.

"Suck it," I commanded.

Her:

A shiver ran down my spine as this man ordered me to suck his cock. I'd never been bossed around sexually; I always called the shots in my marriage. A moan escaped my lips as I opened my mouth and engulfed the huge head of his dick.

I ran my tongue along the rim as the bulbous, spongy head hit the roof of my mouth. I used my hand to pump his shaft while his cock forced its way deeper and deeper.

Now, I'm a blowjob expert. Before I met my husband, my younger, sluttier days involved many a blowjob in the backs of cars, behind football stadiums, in frat houses and just about anywhere I could get my mouth on a hard shaft. My husband was hooked the first time I sucked him off, and the first few years of our marriage involved frequent blowjobs and cum swallowing. But again, it had been years, and the cock currently invading my mouth was bringing back all the lustful memories of the dozens of cocks I had sucked and the gallons of cum I had swallowed.

As I focused on the task at hand, I vaguely became aware of movement around me. From the corner of my eye, I recognized the silhouettes of others, peering through the light shades that separated the dining room from the bar.

Unlike when we were at the pool, I was no longer embarrassed. The audience now fueled my lust. With both of his hands on my head, holding me firmly in place, this sexy stranger stood up. His shorts fell to the floor, and I looked up at him.