Company Executive

By Stoneypoint

Original link:

Tags: Mature, older, younger man, sex,

Added: 12 Sep 2011 Views: 23509 Avg Score: 4.67

Younger man meets older woman, who is attractive, at mall and has sex

I had to go and get a few new shirts for work, seeing as I finally got a new job. So instead of going to some lower priced store, instead I went to the mall where I knew they’d have better but a little higher priced shirts.

When I started heading for the department store there I saw her, a tall, but slender and shapely woman who had to be several years older then me. My eyes and soon enough my thoughts latched on to her figure as I headed closer and closer to the department store.

Maybe she’s going into the department store too, I told myself. A smile soon developed on my lips. It vanished as she turned left into another store just before where I was going. I looked up. It was a lingerie store. I smiled again. Hmmm, that’s interesting I told myself and again I looked down at her and at her figure.

She stopped just inside the store and I watched her a little bit, as I slowed down too, and I quickly studied her figure. Wow, the woman had to be closing in on, I don’t know, but it appeared to me she had to be nearing 60 years old. She was attractive. She wore short, above the collar blondish hair, but it was her figure which my eyes attached with seeing as although she was older the woman was, like I said, very nice looking, and she appeared to have a heck of a figure as well.

I almost bumped into someone. I excused myself. She smiled and said “Not a problem sonny” and then I walked in and looked for a few, five shirts in fact, for the new job. That took me about 20 to 25 minutes. I paid and began walking out.

By this time I figured the woman was gone. I didn’t see her in the store and so I slowly walked forward as I forgot about her. For whatever reason, I looked back. There she was and she was carrying a rather big looking bag as if she’d purchased several items.

I had it in my mind to say something to the slightly older woman. Personally, I’m 46, and once I looked at her again, I determined she couldn’t be more then 60, but she was pretty for her age and for whatever reason I told myself to say something to her.

I slowed down again. I slowed some more and “acted” as if I was looking into a store window. She came closer and closer. I saw her from the corner of my eye. As she was upon me, I turned left as if to “bump” into her.

I didn’t. I almost did but didn’t. “Oh excuse me,” I said as I almost ran into her.

“That’s quite alright,” she said.

I immediately looked at her bag. Yep, it was from that lingerie store, and it had me wondering exactly was in it. I looked up and I smiled at her. Do it, I told myself. Just say something. It doesn’t matter. Just say it.

I looked down and back up again. “I bet you’ll really look nice in whatever you bought from there,” I told her.

And her response was “You think so, really?” She never once got righteous with me. She didn’t ever become too haughty with me at all but without smiling or even frowning as if I’d said something totally wrong, which many women might do she said, “I do hope so. It isn’t like I have a man to show these off to so it is nice to hear you say so.”

Wow, like on that note, hearing her say what she’d said, had me heating up, and burning up like a hot stove. My eyes, for a moment, got bigger. I was at a loss for words for a moment. Then finally I got a hold of myself.

“Really, me neither,” I said. “I mean, I’m divorced and I do wish,” and then I thought about what I was telling a woman I knew I had no chance with.

She smiled and her eyes seemed to soften. She followed with “You do wish what?”

“Ohhh nothing,” I said as she seemed to notice me blushing and “retreating” from what I was about to say.

“No, it is alright,” she said. “We have to stick together. What I mean to say is when you are single and older it does seem to get tougher to hear nice compliments so what were you going to tell me?”

I stalled a second. Then I looked at her bag. Then I said it. “All I was going to say I guess is that I believe you’ll look really, really good in whatever you bought in there.”

She smiled right into my eyes. It was a warm and endearing smile too. I absolutely loved her smile. There isn’t any other way of putting it. Her eyes and that smile and how she approached me, so to speak, when she said it warmed me deeply.

All I could think was ohhhhhh, come to papa. Come to papa.

“Is everything alright?” she said.

“Oh, uh, yeah,” I told her once I came back to reality. She was smiling and still looking me over. “I was thinking.”

“I had a thought,” she said, still smiling at me. “Why don’t we see what you think about what I purchased. That is of course if you’re interested.”

I instantly heated up for some reason. Okay, here I am, a man of 46 and here she is a woman of around about 60 and I think she was inviting me to come over to her place and check her out or what she looked like in whatever it was she bought.

“Uhhh, I don’t know ma'am,” I said.

“I’m Theresa, by the way,” she said introducing herself. She smiled, stuck out her hand, and I stuck mine out too. We shook and she then said, “And you are?”

“Oh, uh sorry, I’m Danny,” I told her.

Personally, I’ve always thought I was an okay looking guy so seeing as she shook my hand, and held on to it for a moment, only made me feel better about myself.

“I hope I didn’t insult you in any way,” I told her.

“Nooooo oh no Danny, you didn’t. To be honest, a woman such as me does like receiving compliments such as what you told me. But to be truthful, no man ever sees what I bought in there” she went on to tell me as if she felt bad. “It’s just that it does help to wear this type of stuff, this lingerie. It can and will make me feel better.” She smiled and out of nowhere I noticed she winked at me.

That had my mind streaming, wildly. It had me wondering, a lot. Okay, so she might not look as hot and sexy as some young 20 or 30 year old woman, but I had to admit to myself that Theresa, figure wise, by way of what she had on had highlighted her sleek looking curves and “healthy” figure.

“So thank you,” she went on to say. “I do appreciate what you told me.”

“Uh you’re welcome,” I replied, smiling. We said our goodbyes and I thought I’d seen her look back at me but she didn’t and then I called out to her for some reason. “Hey, Theresa, hey Theresa,” I yelled out.

She stopped. She was smiling, again. She looked at me. I seemed to think I liked those eyes. I did like her eyes. I really liked her smile too. And I knew I liked her body for sure.

“Can I invite you to an early dinner?” I said.

She looked at her watch. She smiled and looked back at me and then looked at her watch again. It appeared she started nodding when out of nowhere she said yes that she’d like that. Wow, I told myself, here I am, and was about to have dinner with a woman I didn’t know at all. However, I was having doing it anyway. I was having dinner with her even though it was only a bit after five pm.

“This is nice,” she said warmly. “Meeting you and having dinner too,” she went on to say “I mean what woman, my age,” and that got me to wondering just how old she was exactly “gets a chance to have dinner with a younger man as nice looking as you?”

Me, a nice looking man, really I told myself. She had to be kidding me. She had to be I told myself but I thanked her and smiled and then she went on to ask, or say, “So do you really want to see me in all this, I mean what I bought?”

Hell yes, I thought. Why not? “If you think that’s appropriate” I told her.

“Danny, I’m a single 61 year old woman. I may be somewhat attractive in some ways but a woman, my age doesn’t ever get a chance, like today, and so I’ll take whatever chance I can get. That is of course if you really would love to come by.”

I heated up, again. What the hell, I thought. Yes, yes, and again yes I thought as the smile grew bigger on me. I was nodding and telling her yes as modestly as I could. That smile of hers seemed to sweeten and warm me up as if someone had turned up the heat in the restaurant. She gave me directions to her house. She ended up paying and told me I could buy the next one, seeing as I had been out of work, and was just starting a job, which I hadn’t told her where. We got up and I tried following her. I got a little “lost” but found her house, a nice, small, and modest two story place.

She had already changed or maybe she was wearing it beneath what she had on. When she answered the door it surprised me too. Smiling, as always, she answered it while adorning a robe, and whatever was beneath that.

My eyes were all over it. “I assume from how you’re looking at this that you like it?” she asked in the sweetest sounding tone. “Now, I have a question for you. Come in and sit down," and with that she offered me something to drink. I took water. “Now my question is this.”

I waited and she went on to ask “What do you think about my thighs?” as she pulled up the gown showing them off to me.

Wow, holy shit I told myself. "And you’re 61 years old, really? Come on, no way." She couldn’t be. No way, not with thighs that looked as sleek as those looked. I looked up at her once I looked at her thighs.

“God, Theresa you’ve got to be kidding” I told her as I ogled her thighs. “You have,” and I looked for the appropriate words and then found them right away “immaculate looking thighs and legs too.”

“Awwww, you’re just being kind,” she said. I saw her blushing a little as she then sat down beside me. I “warmed” up quickly as she sidled up to my body. “Really, you mean that?”

She happened to smell terrific as well. For whatever reason, I wanted to grab her, and kiss her madly. Whatever that scent she was wearing was it was, it wasn’t overpowering, but it did seem to envelope my desires, quickly. Even I had to admit it. I wanted to kiss this older and very, very good looking woman.

It turned out, of course, that she felt the same way about me as her fingers lightly trailed up over my arm. Seeing as we really didn’t know one another, I didn’t kiss her. Not yet that is of course.

However, she stood up. I grew anxious as hell, and then she removed it. She took off her gown. Holy fuck I told myself! Holy freaking shit! My eyes bulged. I knew she’d see that as I looked at this older woman’s body. Get a load of her figure. Her breasts, that thin waistline, her amazingly awesome looking hips as well, and a body, I thought, was to die for. And she was now 61 years old.

She knew that I loved what she was wearing and showing off as well.

“Let me go and put on something else for you,” she said and then she disappeared. In a minute she was out in another piece. “Now I know I’m not one of your young and sexy looking models or anything but do you like this?” she asked, wearing a soft yet yielding smile.

Yes, I did. It hugged her nicely. Again it highlighted her shapely figure. I loved it. I loved her body like nothing ever before her. Each and every other piece she walked out in looked awesome, but I asked myself, what was in this for me? I mean, for a woman of 61, she appeared to easily liven up a guys life in pieces that did that to her. I felt like the little kid in the candy store, but I was the 46 year old, and she was getting me too interested.

“Ohhhhhhh damn Theresa,” I said. “Everything, and I mean each and everything you’ve shown me is arousing.”

She didn’t turn around. She simply walked up to the couch and sat beside me, smiling. She took my hand and held it. “So this means you like my figure? I’m assuming other men would too?”

“Oh god, hell yes, and I don’t know why you don’t have a boyfriend,” I told her.

Okay, yes. I was aroused. I was horny at that point. I wanted to reach out and touch her body. However, I didn’t even know the woman although we did have an early dinner and we had spent some time talking. But it was general stuff and who really knew what was really going on in her life.

Still I had truly thought about going for it.

“Well, uhhh Theresa,” I started to say to her. “It was uh nice. The dinner and all but I think I should get going seeing as I start work tomorrow. Don’t think for one second I’m not impressed by what you uh showed me, by what you bought.” We looked at each other and she smiled right into my eyes. “I mean you are a very, uhhh, attractive woman,” and I said a few other things.

I stood to leave. She walked me to the door. Before it was opened, she took hold of my hand, and leaned into me kissing me on the cheek.

“Stay in touch, somehow. We can have dinner again, alright?” and I said that dinner sounded good to me, despite of how old she was and how much younger I was then her.

I left, thinking about her, and thinking about her figure too. Wow, that woman did look marvelous, and it took me a long time to shake her out of my head.

That next day, I went into my new job. They had me fill out paperwork and after a while began showing me around the place. “I do want you to meet up with and talk to our Human Resources director” my manager said as we headed down a corridor.

I had no idea. I don’t think she did either. My manager knocked and said to come back in an hour or so once I’d spoken with the Human Resources woman.

My eyes instantly bulged out of their sockets. “Holy shit,” I said accidentally. “Theresa?” as this “loving” like smile adorned her face and eyes. “I never,” and I stopped. “Did you know it was me?”

She nodded and took me by my hand, gently as she smiled and closed the door behind me. I’d heard a click as if did she lock her door? It made me wonder a little. “Hmmm, welcome to the company?” Theresa said. “Hard to believe isn’t it? I mean that you and I working at the same company and ohhh Danny, to think, we almost had sex last night?”

I swallowed hard. She did look good. She looked really good too. Her eyes were full as if happy to see me. They sparkled. She sparkled too. All I thought about was what was she wearing underneath that business suit? Was it simply underwear and a bra or was it something more ornate and sexy such as one of those pieces she’d bought yesterday?

I’m a pretty confident guy. I’m pretty self assured. I think I’ve got balls. Even she said it too that I’m a good looking guy, which doesn’t hurt at all, and so with that I said it. “Okay, so what do you have on today under that nice looking business suit of yours?”

She giggled and also winked at me. “Danny oh Danny, we’re at work honey. We have to follow the rules although yes, we sometimes stray from them” and then she winked again and stood up.

She removed her jacket. I didn’t say a word. She smiled as she did. She slowly, as she watched my eyes, began unbuttoning her blouse. My eyes slowly grew larger. Holy shit, I thought, as I saw it come into plain sight. She was wearing a satiny like corset. Her breasts seemed enhanced to me. Her cleavage was almost “Hyper-extended” to a degree. I looked into her face and she was smiling as she held open her blouse and showing herself off to me.

“I really look nice when I take off all my clothes off too. I bet you’d think that too, wouldn’t you?” she said.

I nodded because that was what I was thinking and as I was something told me that I should say we should get together tonight.

Her eyes seemed to sparkle again and she said “Let’s do this, Danny. Come on over, say around 6:30 and I’ll show you a few more things I’ve bought. I’m sure you’ll love them.”

“You uh really mean that?” I said, seeing as I worked at the same company.

“Sure dear, why not?” she said as she nodded her head and laid a hand on mine. “I’d love that if you would. You would wouldn’t you?”

Here I was, again. 46 and she was sexy and 61. Here I was. Wanting to jump her bones now and kiss the living hell out of her plus of course whatever came with that. I didn’t care if she was older. I’d been married. I had kids. My life, in the past had sucked, but now things were different. I’d finally gotten my degree in business management and I’d met her, a very attractive older woman with a body that didn’t quit.

I told her I’d be over. She smiled. We stood and then she hugged me, warmly. She even kissed me on my cheek. “Remember, 6:30 okay honey?”

She smelled incredible. I wanted to taste her body. I wanted to lick her neck, and more. I wanted to undress her and dress her in something else. I wanted to be passionate. I wanted soooo much more. I wanted whatever we had to be fiery and I wanted to “slam” her against the wall and kiss her forever. That was how and what I felt but I had to get back to work. The day seemed long but I got through it. I couldn’t wait for 6:30.

I drove slowly and pulled up at 6:31. I walked up and knocked. She answered and she was wearing something new but let me tell you. What she had on was sexier then what she was wearing earlier.

She had on a babydoll. It was sort of purple but it didn’t matter. This piece did things to her body that would never work for any other woman. It emphasized her boobs. It showed off her legs. It did everything it was meant to do As she invited me in, she turned, smiled, and asked me if what I’d seen so far, aroused me. Yes, she used the word “aroused.”

Seeing as she was up against the wall, kind of, I “slammed” her against it in a surprising manner, and I enthusiastically kissed Theresa madly. I wouldn’t let up on her either. I kissed her hard. I pushed into her as I kissed her. I threw my tongue out into her mouth and I didn’t let up.

Before I knew it, she appeared to join in, and we were pulling and kissing and grapping at one anothers bodies, wildly. I’m pretty damn sure she loved it. I did. She could kiss and she could kiss really, really well. Her tongue impressed me. She pulled me into her body as her hands reeled all over me and my ass.

“Let’s go to my bedroom,” she said out of nowhere. “Let’s go and see what happens.”

I didn’t say a word. She got me in there and right away she undid my buttons to my shirt. Seeing as my back was to her bed, she pushed me down on it, and jumped on me. She kissed me hard and she kissed me pleasurably.

Our hands joined in as we held one another in that matter, moving them up, and down but always holding on to one another at the very same time. I grew horny. I grew harder. Her hand found its way into my crotch, petting it and pressing down on it a little harder each time. I heard her moaning ever so slightly as her hand worked its way over my crotch.

“You want to get out of your clothes?” she said.

I said yes and before I even had a chance to undress myself she was doing it for me. Her hands were on the buttons and undoing each one as if she’d done it a million times over. Before I realized it, my shirt was off and she was already pushing my pants off my legs as she smiled and worked them all the way down. I was naked except for my briefs.

Still her hand rubbed my briefs enjoying any way she could because she never let up. Her hand moved over my limp cock smoothly and she always looked into my face.

Out of nowhere I felt it. Looking me in the eyes, as she smiled, she slid her soft fingers down inside my briefs. Uhhh ohhhhhh god did that feel good. On it and rubbing my limp cock softly, she went down, and lightly rubbed the tip of my cock, and then caressed it as she came back up.

My eyes closed and remained closed while feeling her fingers and hand do what they were doing. I smiled. She enhanced me or better yet my desire for her. I kept my eyes closed while feeling her hand on my cock.

“You like this do you?” she asked softly.

I nodded and as I opened my eyes I smiled. “You know,” I said, “you really are beautiful.”

“Awwww thank you,” and with that she kissed my lips.

With that, she took one of my hands and brought it up so that I’d feel her boob. It felt too terrific for words. I handled it splendidly. I rubbed one and then the other. I did it some more and then some more and as I did, I’d squeeze them more and more.

As I did, I’d look at her. She seemed to like it a lot and seeing as she did, I pulled the straps off her piece she had on and I began kissing her upper body, slowly. She stopped moving about once I kissed her body.

I went lower and lower and as I did I began to kiss her cleavage and eventually her boobs and once I did that, I pushed what she had on down off her upper body altogether.

I wanted to swallow this woman up. I wanted to consume her body. I wanted all of her and I wanted it now but I didn’t do anything but kiss her all over the place. I kissed her cleavage and breasts and her sides and her belly. I went back up doing it all over again.

I finally knew it. I wanted her thighs. I began pulling almost everything off her. She was almost naked but naked enough for me as I kissed and kissed and sucked on her body.

Before too long, I’d gone down all the way. I’d gone to her thighs and sucked and kissed them just before landing on her pussy. Ohhhhhhh yeah, her pussy. Yeah, it was shaved and it was just as good as any young woman’s ever could be too.

I licked her and she loved it. I sucked on it and she loved that also. I went into her pussy, with my tongue, and she seemed to “growl” once I did that, and it even kind of aroused me also. So, I did it again and she “growled” again. It was weird but she loved me doing it so I didn’t stop doing it as I tongued her pussy some more.

“Want me to go in you?” I asked.

She shook her head. “Just do what you’re doing,” she said.

So I did and she loved it. Her body jerked and moved about as I ate my lover out. Theresa and her body was total joy for me as I held it and ate her out. I climbed her, finally, and with a leg on each side of her I climbed over her. I smiled.

“Are you enjoying all this?” I asked.

“Yes but are you enjoying all this?” she said.

“Oh yeah, for sure Theresa,” I told her. “Do you really think I’d be here if I thought you weren’t sexy and attractive and a nice woman and all?”

She had to think about that. Then she told me no. Then she said come here as in bend over so she could kiss me and hold me, which I did. With that, she reached in, found my cock, and slid it up inside her.

“Want to fuck me now?” she asked.

“Uh sure,” I told her. “I’d love to if you want me to.”

“I do,” and with that, she put me inside her warm and wet cunt.

She pushed at me. I pulled out a little and pushed down into her. We repeated it and kept on doing the same thing but before I knew it she was on top of me. We fucked that way and a number of ways and I told myself do it whatever way she wants it done.

She yelped and cried out as well as squealed pleasurably while I blissfully had my fun too. I liked this woman, personally, and also physically. She was, regardless if she was the Human Resources director at the same company that I worked at, a fun and fantastic fuck if ever there was one.

She dropped on top of me, breathing heavily. Finally, she looked into my eyes. “Did you enjoy it too?”

“Oh god, yeah,” I said.

“But you didn’t cum, Danny.”

“Oh heck, Theresa” I told her. “Maybe another time” I went on to tell her. “We can always do that another time.”

“Nooooo, oh no,” she said as if demanding something. Then I knew what it was. “A man, who makes love with a woman, like we made love, has to cum on her or with her so here. Let me make you cum and you can do it all over my face and tits.”

And so she did and once that was done, she swallowed, and we snuggled for a while.

“If an invite’s open, I’d sure like to come and enjoy being with you again,” I told her.

She was silent for a bit but eventually looked into my eyes and she nodded.