First Time Cheater

I can be a judgmental prick at times about quite a number of things. Life, however, has a funny way of teaching us lessons. I had always viewed people that cheated on their spouses with a fair amount of disdain, particularly those people that just don't give a shit and constantly pursue extramarital sex without the consent of their spouse. Truth be told, I'm still quite judgmental about those folks to this day. Me? I'm different kind of cheater altogether.

I never would have thought I would succumb to stepping out on my wife. She and I are very much in love with each other, recently celebrating our fifteenth wedding anniversary. We have very good jobs, live in a beautiful apartment in a luxury building in New York City, own a beach cottage on the North Fork of Long Island, and have two wonderful children. We have accumulated a fair amount of wealth. Many people would think we have perfect lives, and I reckon we do at that.

When I took my wedding vows, I had every intention of living up to the forsaking all others. I was not, however, so naïve as to think there would never be any temptation to break that vow. As such, I have always avoided situations that could put me in a compromising situation. I understood that we humans are animals, and it is the natural order of things that we try to mate. Our intellect allows us to override that natural instinct, because we can consider the consequences of such a thing in ways that other animals cannot.

I have also mentally kept other women that I know in the friend zone in my mind. We have a group of couples that we socialize with frequently. Several of the women are quite attractive, but I don't focus on that or think about it at all. I don't fantasize about them when I'm having sex or masturbating. I see them as friends. I do understand they are beautiful, much the same as a father might realize his eighteen year old daughter is beautiful. But the recognition of that beauty is only that; it does not become sexual in nature or become a point of obsession.

I found myself alone in my apartment on the Saturday morning of Memorial Day weekend. My wife and her mother had taken the kids down to Disney for five days, so I was on my own. I was scheduled to play in a charity golf tournament at the Trump Golf Club in Westchester on Sunday morning, so I decided I would just stay in the city for the weekend.

After eating a light breakfast, I pulled on my swim trunks and a t-shirt, stepped into some flip flops, grabbed a book, and took the elevator up to the roof deck to take in some sun and a dip in the pool. The pool area was already crowded, which was a bit surprising. Usually, a holiday weekend such as this saw they city empty out and become a virtual ghost town, Today, however, it seemed as if everyone that was still in the city was up on this roof. I was fortunate that a chair opened up just as I arrived, and I promptly took up residence in it.

It was a beautiful sunny morning, the temperature on the poolside thermometer reading eighty two degrees, and the air dry with a light breeze. I picked up my book to read, and the woman who was lying face down in the lounge chair next to me sat up. I glanced over and saw that it was Hannah, who lived with her husband and two daughters down the hall from us.

"Hi, Hannah. I didn't realize it was you lying there," I said.

"Hey, Tom. I'm surprised you're in the city this weekend. Don't you all go out to the beach every chance you get?"

"We do, but I'm flying solo this weekend. Vicki and her mom took the kids down to see Mickey Mouse. I'm playing golf in Westchester tomorrow, so I decided to just stay in."

"That's funny. I'm solo too. Dave took the girls to Paris for a week, and I couldn't get off from work. Where are you playing tomorrow? I'm playing in a charity tournament myself."

"The Trump Club in Briarcliff Manor," I replied.

"Get out! Me too! How are you getting up there? I was going to rent a car, but there aren't any available. I'm stuck with the train," she said with a frown.

"You can hitch a ride with me. I'm driving up".

"That would be perfect! Are you sure you don't mind?"

"Not at all, Hannah. It will be nice to have some company for the ride".

"Great! Could you watch my chair? I need to go to the little girl's room".

"Sure. It will be under my watchful eye."

Hannah smiled and padded off to the ladies room, and I watched her go. Hannah is a doll. She is short, perhaps about five feet, two inches tall, and athletic. She is trim, with a flat tummy and toned limbs, and an ass that is just curvy enough and completely adorable. It was that ass I was staring at as she walked, and she had an adorable little wiggle to her step. I'd guess that her cup size is a very full B spilling over into a C, which on her frame looks quite nice indeed. She has flowing blond hair that is a bit longer than shoulder length. She requires very little makeup, and has bright blue eyes and soft, full lips. Picture that cheerleader you lusted after in high school at her twentieth reunion, still looking incredible. That is Hannah.

Hannah returned and we chatted a bit more, and then I got up to take a dip in the pool. I spent about twenty minutes doing laps, and then floated around for a while. Hannah sat up and was applying sunscreen to her arms when I got out of the pool and walked back to my chair. She was wearing sunglasses, but I could tell she was watching me as she rubbed the cream into her arms.

At forty two years of age, I'm still in great shape. I watch what I eat, lift weights, and perform some rather intense workouts on a regular basis. Standing at six foot three inches tall, I tip the scales at about two hundred and eight pounds, and with a body fat percentage that is usually in the eight percent range. I've been told that I'm quite handsome by women in my life, but honestly, what are they going to say?

I grabbed a towel and dried off, and then sat on the chair. Hannah continued applying sunscreen, now moving to the front of her legs, then standing up and spreading it onto the back of her legs and whatever part of her butt cheeks were exposed. I was watching out of the corner of my eye. I mean, who wouldn't? When she finished, she looked over at me.

"Could you do me a favor and do my back," she asked.

"Sure," I said, grabbing the tube from her hand. She sat with her back to me, and I put a glob of sunscreen into the palm of my hand and spread it all over her back. As much as I enjoyed it, I was respectful and didn't linger in any one place too long. I handed her the container back, and said "I think you're good, but I take no responsibility for any missed spots".

"Thank you, Tom," she said. "I promise I will take full responsibility".

I sat in the sun and read for a bit, breaking it up with some small talk and a swim now and again. By two in the afternoon, I was getting antsy and started gathering my stuff up to leave. Hannah looked up at me.

"Leaving already," she asked?

"Yeah. I'm going to get a workout in, and then maybe take a walk along the river. I've been sitting in one spot for too long."

"I'd better think about getting out of the sun myself," she said. "Hey, what are you doing for dinner tonight? There's that new steak place that opened up on eighty-fourth street that I'd love to try. I don't want to go to dinner by myself. Are you game?"

"Sure, why not? It will be nice having dinner without the kids bickering with each other all meal long."

"Don't I know it," she said. "How about seven o'clock?"

"Perfect. I'll meet you down in the lobby."

"See you then."

I got changed for the gym, and headed over for my workout. At this point, there were no alarm bells going off in my head, at least not yet. We really weren't flirting with each other at all. Of course, I noticed that Hannah looked great, but I wasn't mentally taking that anywhere. I got in a very good workout, and afterword, I walked up and down the riverside walk that runs along the east side of Manhattan. After arriving home, I shaved and jumped in the shower, dried off, and then got dressed. I was wearing tan shorts, a light blue golf shirt, and a pair of casual shoes with no socks. I went down to the lobby at around a quarter before seven to wait for Hannah.

The first alarm bell that went off was when Hannah got off the elevator and walked into the lobby. She looked stunning, wearing a form fitting casual black dress and black sandals, her hair put up in a casual looking bun that must have taken her an hour to get just right. Her tan was perfect, and she had an incredible smile.

"Hi Tom. Were you waiting long?"

"No, I've just been down here for a few minutes." I paused for a moment. Wow. Summer really agrees with you. You look incredible," I said.

Honestly, I don't know why I said that, other than the fact that I was just a bit off kilter by how good she really did look. It was out of my mouth before I could even think.

"Thanks Tom, she said with huge grin. It must be the tan. Between that shirt and the tan you got, your blue eyes are like neon signs screaming to be noticed," she giggled. "You ready? Let's go make everyone gawk at us."

"I am," I said, and we walked out of the building, turned left onto Third Avenue, and walked the few blocks down to the restaurant.

We were seated at a sidewalk table, and had a wonderful dinner, sharing a bottle of wine and some good conversation. We decided that we'd go see "The Hangover, Part Two", which had just come out that weekend.

Walking home from the theater, Hannah giggled. "I feel like I'm on a date, and I haven't been on one of those in ages. It was actually fun and I feel a little naughty," she said.

"I had a nice time too," I offered, backing off her comment just a bit.

We entered the building and rode up the elevator in silence. When we got to our floor, we walked down the hall towards our apartments. Hannah stopped at her door. "What time should we leave tomorrow," she asked.

"Around eight? I'll meet you downstairs again?"

"Sure." She paused. "Tom?"

I looked at her.

"Thanks for dinner and some good company. It's a little lonely with Dave and the girls gone."

"I hear you. Thank you too. Now, get some sleep. We have some golf to play tomorrow."

She opened her door, waved goodbye, and went inside.

I stripped down naked and fell into bed, and slept long and hard.

The next morning I met Hannah down in the lobby again. She was wearing white shorts and a pink shirt, her hair pulled back in a pony tail. She looked a bit like that cheerleader she surely had been in high school. I took her clubs from her and we went down into the parking garage, loaded them into the car, and were on our way.

We engaged in some more small talk, updating each other on what the spouses and kids were doing on their trip. We arrived at the club and went to check in. We were both playing solo, so we were paired up with another couple and assigned a tee time.

I was a fairly decent amateur golfer in my day, and Hannah held her own as well. In fact, we were running neck and neck, and were tied coming down to the final hole. We had been taunting each other the entire day, and now we would see who would hold the title of best golfer of Eighty Seventh Street.

"Loser buys the winner a beer," I proclaimed as I prepared my tee shot.

"Deal. I'll have a Blue Moon, just so you know when you go up there to buy," she said with a wink.

I hit a perfect tee shot on the par four, eighteenth hole, and smiled at Hannah.

"I hope you brought your money," I said.

She stuck her tongue out at me, and prepared for her drive. She hooked her shot into the rough, and ended up with a bogey to my birdie.

"Okay, I'll buy the beer. But please tell me I'm not going to have to listen to you brag all the way back down to the city," she said.

"Just halfway down," I chuckled.

We went into the clubhouse, cool with the air conditioning, and had a beer and a burger. After finishing, we were walking to the car when Hannah fell down as she was walking next to me. I stopped to help her up, and realized she had twisted her ankle on an errant ball that lying was in the parking lot. I lifter her up and brought her to a bench, then went into the pro shop. They had a disposable ice pack, and, fortunately, an Ace bandage. I held Hannah's foot on my lap as I wrapped the ice pack around her ankle and secured it with the bandage. She was watching me intently as I worked. I took the golf bags to the car, and then came back to help Hannah. The car was quite some distance away, and we weren't making much progress with her hobbling along with my arm around her waist.

"Hold on," I said, and scooped her up in my arms. She wrapped one arm around my neck and put her other hand on my shoulder, and giggled like a school girl. The walk to the car was about four hundred yards, and I effortlessly walked over there. She turned her face towards me, about a foot away, and looked in my eyes.

"You're pretty damned strong, Tom," she said.

"This is why I work out. You never know when a damsel will be in distress. One must be prepared in life."

"I'm a damsel in distress, am I," she said. "I guess I'm very lucky you happened to be here, then, aren't I."

The second alarm bell went off when I looked at her face. It was obvious she was seeing me as a man. Not as a friend or as an acquaintance, but as a man. I admit that I liked it. Quite a bit, in fact.

"I reckon so," I said, as I smiled at her.

I got her settled into the passenger seat of the car, and we drove back down. I teased her about purposely spraining her ankle in order to avoid further discussion about my victory. Despite her tender ankle, we had an enjoyable ride back to the building teasing and chatting. When we got into the garage, I helped her over to the elevator and into her apartment. We got her settled onto her couch, and I pulled up the ottoman and sat on it.

"Let's have a look at this," I said as I unwrapped the bandage. The ankle was swollen and a bit discolored.

"This is going to take a few days to heal. What can we do to set you up so that you can function?"

"I did the same thing a couple years ago," she said. I have a pair of crutches in the closet in the bedroom. If you could get those for me, I'd appreciate it."

I went into the bedroom and found the crutches. I carried them out into the living room, and leaned them against the couch.

"Let me wrap this up again for you," I said, grabbing the bandage. "You should ice it every hour or so, and then put the bandage back on."

She rested her foot on my thigh and watched my hands intently as I wrapped her ankle and foot up. I glanced up at her, and she had that look on her face again. It was clear that she was enjoying the feel of my hands on her flesh. Frankly, so was I. I lowered her foot to the ground, and looked across at her. She was biting her lip, and I could see that her breathing was a bit labored.

"I can't believe we are going to do this," she whispered. It wasn't a question. It didn't require a response. It just was. We both leaned forward and I put a hand on her cheek, drawing her in for a kiss. That first moment...her lips were so soft. Tentative at first, then our kisses got bolder. Kissing, pulling back a bit to look at each other, seeing the lust written all over our faces. She reached down and pulled my shirt up and over my head.

"You are an incredibly sexy man," she said to me. "This body is ridiculous. Your wife should make you wear a winter coat all year long," she laughed.

We kissed some more as her hands roamed all over my chest and back. She pulled away and yanked her own shirt off, revealing a pink lace bra that produced picture perfect cleavage. The cleavage didn't last long, as she removed the bra very quickly. I ran my hands up her sides and cupped her tits in my hands, lightly pinching the nipples.

"Fuck. I've been watching those strong hands of yours. They turn me on. I found myself wishing you would touch me with them like you are now."

We continued to kiss as I played with her tits, and our passion grew by the minute.

I stood up before her, and she unbuttoned my shorts and yanked them down, along with my underpants. She looked up at me with a bit of fear in her eyes, then looked back down at my cock. She grabbed it and stroked it several times, looking up at me again, but this time with a lust filled smile on her face. She took me into her mouth, stroking me as she slowly moved her mouth up and down on my cock. She spent a couple minutes stroking, licking and sucking, and then she got up with a helping hand from me.

I undid her shorts and yanked them down, running my hands over her ass cheeks. I then reached a hand around in front of her and slid it down to her pussy. She opened her legs to give me access, and I slipped a finger inside her. She was wet and well lubricated, but I toyed with her until she whimpered. I pulled her thong down and tossed it aside. I lay on my back on the floor, and she got on her knees straddling me, rubbing her pussy on my stiff cock, grinding her clit on me. She tensed up and bit her lip, trying to stifle her moans as she had her first orgasm.

When she had calmed a bit, she reached behind her and grabbed my cock, bent forward, and rubbed it against her slit until the head pierced her and slipped inside. She let out a deep breath, and slowly moved back to let more of me inside her.

"Easy," she said. "You're a bit bigger than Dave. Give me some time to adjust."

I was pinching her nipples and watching her face as she backed up, inch by inch, until I was fully inside her. She sat like that for what seemed an eternity, a look of immense satisfaction on her face, before she slowly started to rock back and forth on me. She leaned forward and started kissing me, and we fucked like that for ten minutes, kissing and groping, us moving in unison.

"I'm going to cum," Hannah, I said. I wanted to give her fair warning in case she wanted me to pull out.

"Yes. Give it to me, Tom. Fill me. Fuck me. Fill me now, baby". She was bucking harder and faster than ever, and I bit her bottom lip as I came hard, thrusting into her as she rode me. She collapsed onto my chest, and didn't move until my cock had subsided slipped out of her.

She rolled off of me onto her back, and I kissed her neck, then made my way down her tits to her tummy and then down to her pussy. Hannah had a beautiful cunt, and it was adorned with neatly trimmed blond hair. So, she was a natural blond as I suspected, I thought.

I started by sucking on her clit as I flicked my tongue around it in circles. She arched her back and moaned, reaching down to grab and pull my hair. I kept this up until she came again, and then I slipped a couple fingers inside her and began fucking her with them. Hannah had given up on trying to be quiet, and now everything I did to her brought out a gasp or moan or scream. Using my tongue and my fingers, I made her cum twice more, until she finally pushed me away as she could take no more.

She curled up next to me and put her head on my shoulder, kissing me and touching me, lost in the moment. We lay like that for a while, until she got chilly and got up. She hobbled into the bedroom to get a robe, and I threw my clothes back on.

We were both hungry, so we ordered some food and ate while we watched a ball game on television. After dinner, Hannah snuggled up next to me and started nibbling my earlobe and whispering suggestive ideas to me. I scooped her up in my arms and brought her into the bedroom, and layed her face down on top of the bed. I pulled my clothes off and climbed onto the bed, kneeling between her legs. I reached down and grabbed her by the hips, pulling her up onto all fours. I rubbed my stiff cock all over her pussy, making her squirm and wiggle her cute little ass.