Maya Pt 01

This story is dedicated to someone very special, a beautiful and caring lady who is very dear to my heart. And I care about her dearly. You know who you are, sweetheart.

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My name is Ira. I grew up in Queens, NYC, in a mostly happy childhood. I married young, when I was 20 and still in college. Me and my ex, Tracey, were crazy in love and we just couldn't wait to get married until after we graduated. It was heaven at first, going to school and working part time and living in a tiny off campus apartment. We had little since neither of our parents were happy about us getting married in our junior year and they didn't help us out, but we didn't care. We were in love, after all.

The first 3 years were great. We didn't get out socially unless it was just to hang out with friends and it was enough for us. But after a few years, we fought about being broke all the time. We both worked, but we had starting salaries and loans to pay, Soon we were fighting about everything. The great sex we used to enjoy dried up to almost never. We realized we got married too young without knowing enough about each other. So we got an easy divorce. No kids, no assets, no fuss. No bitterness either. We said goodbye amicably and went our separate ways. I moved back in with my parents and she moved out West to stay with a friend in California, where she lives to this day. I'm in New York, our hometown.

So from the time I was 24 I was divorced and I concentrated on my career. Since my degree was in Philosophy, there weren't a lot of good paying jobs around in my field. You learn how to think in an objective way, but it's not a career practical area of study. I got a job in retail sales, and over 3 years I worked my way up to a management position in a major, upscale department store. 3 years after that, I was offered a position as a store manager in a new location, still near my home turf on Long Island. By then I had my own home, a small 3 bedroom, 2 bath about 20 minutes from where my new job would be. I invested my money, mostly wisely, and over the next twenty years I built up a nice nest egg and I was being considered for a corporate position working out of the headquarters in Manhattan.

I was 50 now, and had it all going right, except I was alone. I was now middle aged with no family. I looked good (you have to maintain a physical appearance and you have to dress well in upscale retail). I was 5'9" with a broad build, not fat. My hair was thinning and greying at the temples and I had a Van Dyck style beard and mustache, also going a little grey. I had a closet of dark suits, a couple of lighter suits for hot days, a whole bunch of white and blue dress shirts and about 20 ties. About a half dozen pair of black and brown shoes with plenty of socks. I looked the image for my career.

I had a number of blind dates over the years through friends. Some went decently well and led to short term relationships and others were just two people who had little in common, one and done dates. I could have dated plenty from the mostly women I worked with, but as the boss in the store, that's a huge no-no. It can only lead to problems, either with the woman you get involved with or with others who can develop the feeling that there's favoritism going on...just too many problems. I even had opportunities with various customers who let me know they were available, but that could be equally bad if things went south.

So over those years, unless I got into some relationship that went well for a few months, my sex life was pretty sparse. There were entire years I didn't get laid at all. Even more than that, I missed female companionship. Someone just to share life with, someone to cuddle with in bed or on the couch, someone to just have dinner with or take to a concert. I had a social life with my friends, went to ball games and concerts, dinners and drinks. I just couldn't seem to meet someone that I clicked with.

I was watching a ballgame, the Yankees, at home one night when an ad came on between innings for a dating site. Sure, the models were all gorgeous and they even did international connections. I knew people lied on these sites, sometimes even putting in a picture that was years old or had no resemblance at all to the actual person. Men and women did that. But I was tired of not having someone to share my life with and I figured, what the hell do I have to lose? A few bucks? So before I could change my mind I was on the website on my laptop, put in my credit card for a signup fee, and filled out the profile and uploaded a picture that was less than a year old, dressed in one of my best suits from a corporate event. If others wanted to lie, that was on them. I didn't search for a woman, I decided to let them seek me out and I could go from there. Then I went back to my game.

2 hours later, when the game was over (Yankees won!), I went back on my computer and saw I got over 20 hits on my profile. I had given an age range from between 25 (I know, too young for me) to 50. A few years older would be fine, but not more. And the hits were from everywhere. A few were local, within 10-30 miles but most were from other places in the country and 3 or 4 were from women in Europe. Talk about a varied pool of possibilities.

I was nervous as hell about answering any of those responses, so I decided to just winnow through a few and see what I had there, starting locally. No, no, maybe, definite maybe, no, maybe...I went through 10 profiles like that, deciding that 4 were worth following up on. But not that night. It was after 11 by then and I had to be at the store at 8 to open to let people in to set up a sale.

Two days later, I answered each of those four possible matches. Two were within 20 minutes drive, one was a little further and the fourth was in Connecticut, a lawyer and, from her picture, a real looker and 36 years old. She was actually my favored choice. The first one, after messaging back and forth, agreed to a Skype conversation.

I don't understand why people lie or fake their profiles and then agree to meet online. Her picture on her profile had to be at least 10 years old. She was clearly a lot older, and wasn't a little heavy, which I wouldn't have minded, but she was a big girl. Over 200 pounds. Everyone has their tastes, and I know some guys would have been very attracted to her, but not me. I was polite, we talked a while and she was nice and smart, but I just was not interested. And so it went with the next two, for one reason or another we didn't connect. I'm not going to claim it was always me finding fault. The third lady, who lived in Queens, about a half hour away, wasn't interested in me after we talked a while. The fourth, the lawyer, went very well. After talking by streaming for almost 2 hours, we agreed to meet in Manhattan for dinner. She worked in the city, so it was easy for her, and I suggested a night when I was off work. So that Thursday night I drove into the city and met Elaine at the agreed on Italian restaurant at 6.

The evening went very well, we had a lot in common and she was, as I said a looker. Short black hair and a slender build with a cute face. We were obviously attracted to each other and after dinner, we made plans for me to drive up to her house in Stamford Saturday. We'd spend the day together and she'd take me around and we'd see what happened.

I brought an overnight bag with me, just in case, which I left in the trunk of my car. It took about two hours to get there and when Elaine answered her door, she had a broad smile as we kissed on the cheek. She had a lovely home, which she had gotten in her divorce four years before. After showing me around, we got in her car and she took us to neighboring Greenwich, one of the most exclusive towns in the country. We went to lunch at a sidewalk bistro and then we walked around the historic district, wandering into a few art galleries and antique shops between our conversations. We were having a great time.

Around 6 we stopped into a bar for a couple of drinks and our hands touched across the table. We decided to stay there for dinner, specializing in seafood. We had wine with dinner as we kept talking and there was a definite sexual tension between us.

By the time we were done it was 9 and I had to know whether I was staying or going. I had a two hour ride ahead of me if I left and I had more than a little to drink. I'd need some coffee if I left. But I hoped I was staying the night. We got in Elaine's car and, after she started it, we faced each other and moved in for a tentative kiss. It was nice, soft and her lips invited me for more so I kissed her again, with more confidence. Her lips parted slightly and the tip of my tongue traced over her perfect white teeth. Our arms went around each other and our kisses became very passionate. After a couple of minutes of that, we broke off and Elaine smiled sweetly. "So, Rich, do you have to drive home tonight?"

Bingo. "No, I have no plans for tomorrow. What do you have in mind?" I asked, teasing her.

"I thought you might like to spend the night. With me."

"Let me think about it for a bit. Yes" I said quickly, and we both laughed. It wasn't a great joke but I tried to be cute and it worked well enough. Elaine drove us to her home and I asked if she minded if I brought my bag in with us.

"You must have been feeling kind of confident this morning. Of course, bring it in. You'll look kind of silly going out to your car in the morning with no clothes on. Or in my robe."

I got my bag and followed her to her door, her broad ass and perfect legs leading me on, shaking back and forth in front of my hungry eyes, in her tight, white skirt. She led the way upstairs, her ass shimmying from side to side like she was deliberately trying to entice me.

When we got in her room, we embraced for a series of kisses, soft and brief and hard and passionate. I ran my tongue along her teeth and Elaine bit softly on my tongue and then my lower lip. Our hands explored each other, getting to know the shapes of each others bodies. I'm sure she could feel all 6 inches of my erection pressed tight between our bodies. It was trapped in the snare of our tummies.

Elaine eased back and said "Why don't you get comfortable, and I do mean COMFORTABLE, while I go and put on something I'm sure you'll just love. I won't be too long. I expect you to be naked when I get back." She turned like a soft breeze and headed for her bathroom.

I was unusually clumsy getting out of my clothes. It had been over a year since I'd had sex with a woman and to say I was eager was a ridiculous understatement. My shoes and socks, my dark slacks and red Ralph Lauren button down shirt were in a pile on the floor, in a way I never left my clothing. I was going to leave my navy boxers on, then I remembered what Elaine said, and I shucked them off and added them to the pile before climbing on the bed. I propped up a couple of pillows to lay comfortably against the wrought metal bars that made up the headboard of her bed. I waited fairly impatiently for her to return.

A few minutes later she came out of her bathroom and she was worth waiting for. Elaine wore a matching black lace bralette and bikini panties set along with expensive thigh high stockings with black patent pumps. Clearly she had this outfit set aside in case things went well. She wasn't busty, but she had very nice tits. My cock twitched involuntarily and Elaine noticed and smiled her approval.

She silently slid into bed with me, right into my arms and we kissed hungrily right from the start. The lace of her lingerie scraped my chest in a very pleasant way as our bodies rubbed against each other. As we rolled around her bed, our heat raging, I heard a metallic clinking sound I couldn't place but that was familiar. We kept kissing as Elaine pushed me on my back and pushed my right arm up by the headboard, My cock was leaking a little precum on her flat tummy, leaving a trace of almost clear fluid there. I was ready for her. Ready for Elaine to mount me or pull me on top of her, whatever she preferred...

Then she grabbed my right wrist and tried to put a handcuff around it. The metallic sound. I pulled free and grunted "What the hell are you doing?"

"Just spicing things up. I like it very kinky" she said, like this was no big deal.

""Spice things up'? This is our first time together. This is the kind of thing you do when you've been together a year! And you ask first! We barely know each other, for goodness sake! Handcuffs take a lot of trust, Elaine."

"Well, this is what I need, and I'm not ashamed of it!"

"I didn't say you should be. But I'm not doing this the first time I'm in bed with a woman!"

"So you're just going to leave me frustrated? We're not going to fuck?" Her face was red, but it wasn't from passion. She was honestly furious with me.

"No, I guess we're not. I'm going home after all."

After that I dressed wordlessly. Nothing was said between us. Even when I left her house, not a word. Fuck, I was going to have to drive home with blue balls.

I needed some caffeine so I stopped at a Starbucks and got a large iced coffee and did the two hour drive back home. I walked into my house with a gait like I had just ridden a horse all day, went to my bedroom and took a long hot shower where I jerked off to relieve the discomfort and still went to bed frustrated. Online dating. Great way to meet crazy people. I said to myself that's the end of that before managing to fall asleep.

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Over the next few weeks I was in my routine. Work involved dealing with co-workers, dealing with unhappy customers, dealing with my own bosses on conference calls. My days were often 9 or 10 hours long. I wasn't in a rush to get home anyway. Nothing to rush home to.

Every few days I got notifications from various women. I'd take a cursory look and dismiss the requests. I was pretty discouraged.

Then, about a month later, I got a notification from a woman named Maya. She was Polish and she was a lot younger, about 20 years younger. And she was beautiful. I mean it. Not like a fashion model. More like a real down to earth lady. And she had the most lovely hazel eyes. Eyes that could make even the hardest man's heart melt. Her skin was pale and perfect, her lips were full and enticing with a smile that lit up a darkened room. She had brown hair with a touch of a reddish tint, down to her neck, straight, parted in the middle. Just her face alone was enough to catch my heart.

Her message, which she recorded, was in almost flawless English, with a slight accent that actually made my stomach flutter. She told me a few things about herself, about being a single mother of a 5 year old daughter, that she was a graphic designer, she liked books and movies and she ran to keep fit. Then she let her entire body into the shot and I was even more charmed. Maya was petite, about 5'3", she couldn't have been more than 100 pounds, small breasts under her sweater, and shapely legs. Maybe the most lovely woman I had seen.

This one I could not ignore, even though she was 4000 miles away. So I recorded my own message, telling her about myself, how I also loved books and movies, also I liked to swim and ride a bicycle, I loved rock and roll and jazz. A few more details. And I let her see me head to toe, this time in more casual clothes. I asked her if she'd like to skype so we could talk in real time. The time difference, 6 hours, would make things challenging, but I wanted to try. I was definitely interested.

We sent video messages back and forth, at first very friendly, getting to know you kind of messages. She always had a smile for me, sweet and gentle and a little flirty. Finally, after about two weeks, we were able to set up a time to chat live that worked for both of us, on my day off. I met her about noon my time, about 6PM her time. Her daughter, Maria, was with her father so we were alone.

At first, we were both nervous. This wasn't exactly a traditional way of meeting someone. But after a few minutes of uncomfortable giggles and silences, we found ourselves talking naturally, sharing more details of our lives. We were both divorced, me almost 30 years, and Maya 4 years. I was glad to hear her say how Maria was the most important person in her world; I would have been very disappointed if that wasn't the case. We talked for almost 2 hours and I think we were both falling for each other a little bit.

Then I brought up what concerned me most. "Maya, I'm too old for you, really. We're almost 20 years apart. I'll be an old man when you're still in your prime of your life."

Maya smiled, a big, wide smile that showed her perfectly white, even teeth. "Ira, don't you think I knew you were older when I responded to your profile? I prefer older men. They know so much more about how to treat a woman." Her voice, with that slight accent, made me giddy inside. Her eyes, big and warm, made my heart skip a beat. "Men my age, everything they know about women comes from porn. They think they all need to be studs in bed, and they don't make love to a woman. They always have to fuck like a machine. I like to fuck sometimes." Her language was shocking me, but also turning me on. "But mostly, I enjoy being loved. Could you love me, Ira? Emotionally, physically, in all ways? Could you be gentle when I need and be my man when I need that?" Her voice now had a sultry tone that had my cock swelling in my pants.

Maya was looking at me closely, her eyes bright with intelligence and curiosity, "I could. I am so excited by you, Maya. I think you're the most interesting woman I've ever met. You're definitely the most beautiful."

"And I think you're a very handsome, cultured man, who knows what a woman needs and wants." She bit her lip, that full lower lip, coated in a light pink lip gloss. "Do you know what I need right now?"

I was a bit breathless. I was pretty sure I knew where this was going, someplace I'd never gone before. I never masturbated with a partner in all my years. Not in person and not like this, certainly. I hoped I was reading Maya right. "I'm pretty sure I do. I just don't know if I know how to do this."

She sat back so I could see her body, in sweatpants on bottom and a tank top on her body, no bra straps beneath. I wanted to see her and I wanted her to see me. "Just do and say what comes to you. I'm very hot right now, Ira, Hot for you. Can you put out my fire?" She gently rubbed at her breasts over her top.

"I'm going to try my best" I said with a grin, leaning back on my couch so Maya could see all of me, in a pair of jeans and a gold polo shirt. "I would start by kissing you, a long slow kiss on those soft lips. And hold you tight in my arms so you just melt into me."

"Mmmm that sounds very nice. I like the feel of a nice strong man holding me, and I really love when you kiss me. I'd love to feel your lips and your tongue. The thought of it is making me wet."

"After kissing your lips I'd nibble softly on your earlobe, then down the side of your neck and to your shoulder. Your skin is so warm and soft. I love how salty your skin is, how tender your flesh feels. I'm pulling off your top so I can kiss and lick your chest."

Maya took my lead and peeled off her tank top and I got my first look at her breasts. They were small but round, lovely, perfect for her petite body. She had rose colored areolas and nipples and the nipples were firm like little pebbles. She tweaked them between her fingertips and I wished I was there to feel them in my fingers and between my lips.

"I want to kiss them and suck them, baby. I want you to hold my head while I run my tongue all around your hard points. I love to tease first."

"Yes, suck them, tease them, they're all yours, my dear. Just thinking of you is making my pussy flood my panties." The look on her face was lusty and hungry. I hurriedly pulled off my shirt, exposing my hairy chest to her. "Darling, I love a man with a hairy chest. It's so masculine. I love men who look like men with strong features. I bet you're hard for me, aren't you?"