Diane

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A young man desires sexy older co-worker.
2.5k words
4.41
125.1k
33

Part 1 of the 3 part series

Updated 10/05/2022
Created 03/23/2009
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bignfirm
bignfirm
340 Followers

I don't know what's wrong with me. Here I am having sex with a cute girl I met at the bar, and all I could think about is my coworker Diane. The weird part is that Diane is 52 years old and has 4 kids. As I watch the bar chick's tits sway in front of my face, all I could imagine was Diane's still firm boobs stretching the material of the thin sweater she wore today. I remember it perfectly, a cream colored sweater with just a hint of her nipples aching to poke through. Her brown pants clung to her ass, clearly indicating she keeps herself in great shape. We are close work friends, but every time I see her, I devour her lusty body with my eyes, desperately hoping she's thinking about me.

I finished up with whoever this girl was on top of me, kicked her out, and instantly got hard again thinking of Diane. I jerked my 7 inches until I erupted onto my stomach, and then I passed out. When I awoke in the morning, I showered and headed off to work, wondering why I wasn't normal like every other guy. Why am I obsessed with an older married woman with kids when I should be fucking everything else in sight? My question was answered when I arrived in the parking lot, and Diane was getting out of her car next to me. We spoke on the walk to the door, and I made sure to catch many peeks of her taut ass while she told me something about her kids.

Let me finish describing my object of desire. Five foot three, 100 pounds, blond hair halfway to her sexy tush, sexy green-blue eyes, and as I alluded to earlier, fantastic tits sitting proudly atop her chest. They weren't huge, but they were easily a handful, a mouthful even.

We parted ways and met again for lunch, doing what we always did, sitting in her car as we ate, talking about our lives. All I wanted to do was touch her, feel her sexy body, and make her feel like the gorgeous woman I thought she was. I wanted her small hands to fish my hard cock out of my pants, and then her mouth to take me in, inch by inch. After lunch, we had a meeting where it was determined that Diane and I were to attend a training session together out of town that weekend. I was ecstatic obviously, but I feared that she would drag her husband along and I would again be a third wheel. Well to my fortune, her hubby had a golf outing that weekend and Diane and I would be by ourselves. I offered to drive and she gladly accepted.

Saturday morning came and I took my time in the shower, dreaming a bunch of 'what ifs' as I felt my cock rising up. I imagined Diane's 52 year old small frame being ravaged by my 25 year old penis, a look of pure joy on her face as I fucked her. I came back to earth, dressed, and hit the road. Diane was waiting in front of her house when I arrived, donned in a fairly short skirt, and a dark tank top. Her tits looked fantastic, and I tried to make sure I focused on something else when she got in the car. I did feel a bit like a sleaze when her young children came out to say goodbye to her. After all, I should not be lusting after their mother. Their sexy, older mother with her tight little body, her great ass, those tits....Ugh, how was I going to get through this weekend?

Diane and I hit the road, and I had to have the AC pumping full blast as this particular summer day was sweltering. A few hours went by, and we were about halfway to the conference center and hotel. Every time Diane looked out her window, I would examine her hot body, alternating between her firm tits and her bare legs. One time I was just about to get caught as she abruptly turned toward me, but as this happened, I felt the car start to shake. I couldn't get control and there was smoke coming from the hood. I managed to get us to the side of the road safely, and I checked under the hood, feigning any mechanical ability. We determined the car had overheated. It was undriveable and we were in the middle of nowhere, on a long highway that had no visible life in either direction from where we stood. We waited around for several minutes until a truck happened to come by and took us to the next town up, where I had the local gas station tow my car. They wouldn't be able to look at it until tomorrow morning, and they suggested that my 'mother' and I get a room at the motel up the block.

Diane had been outside trying to reach her husband but she couldn't get any reception. I told her what the mechanic said, and she agreed we had no choice but to grab a room. I must admit I was not that bummed that this was all happening because it gave me more time around my sexual fantasy Diane. The motel clerk offered me a room with two queen beds, and as I was handing him my credit card, I had a better idea. I figured it was now or never with Diane, so I took a room with only one bed.

When I returned to Diane outside, I gave her the 'bad news' that the only room available was a single bed. She gave me a strange look and agreed, but I don't think she thought I was lying to her. I followed her sexy ass as it sashayed in front of me to Room 16, wondering if I had the balls to do make any kind of move, and assuming that the answer to my question was no. After all, Diane is happily married. She went to take a shower as I got settled in the room. I noticed it was a bit chilly in the room so I raised the temperature to a more comfy level. Then I got another bright idea. I raised it way up until the room was almost unbearably hot. When Diane exited her shower and commented on the heat, I explained that the thermostat was broken and the clerk told me they wouldn't be able to fix it until the next day.

After I showered we grabbed a quick bite, and then retired to the motel room, as we were going to have a long day tomorrow. I told Diane to take the bed, and I would sleep on the floor, knowing and hoping that she was too sweet a woman and would not allow me to sleep on the floor. Luckily I was right and she told me to share the bed with her. I agreed and I laid down facing away from her, wearing my shorts and a t-shirt. She wore a t-shirt as well, along with sweatpants. Ill admit that as great as this was for me, it was a bit awkward as we were only work friends, and she was married.

I tried to fall asleep as she put the lamp on to read. I felt the bed suddenly move a bit and I looked over to see Diane removing her t-shirt, leaving her in just a white, lacy bra. She saw me glance over and she quickly apologized, telling me how hot she was. Um, I already knew! Anyway I faced away again, now with the image of her bra imprinted into my brain. My dick was rock hard instantly, and I could almost smell the sweet pussy sitting right beside me. I tossed around in the bed trying to get comfortable, when Diane leaned over and said:

"You can't be comfortable trying to fall asleep with your penis like that."

I was mortified. Here I thought she had no idea what she was doing to me, and now she's bringing it up. I asked her naively what she was talking about, and she took my shoulder and turned me toward her so my dick tented straight up toward the ceiling.

"That's what I mean," Diane whispered. Her breathing was becoming noticeably heavy.

I asked her if she was mad, and she told me she was flattered. She went on to tell me how she sees me catching glimpses of her body all the time, and she can never believe why I would lust after a significantly older, married woman. I told her I thought she was the sexiest woman I know, and how I dream about her when I fuck other girls. As I spoke, her hard nipples stuck out, telling me she was aroused like me. I decided to see where this could lead so I reached over slowly to her chest and I placed my hand on her breast. I looked to her face for a sign, and when she smiled, I proceeded to squeeze her boob, feeling her up like a giddy schoolboy. I massaged her tits through her bra, and she moaned lightly as her eyes closed.

By now my dick was ready to rip through my pants but I didn't want to press my luck just yet. I lifted her up slightly so I could undo her bra, and she made no effort to stop me. That's when I knew I was going to live my ultimate fantasy out right now by fucking my lovely coworker. I removed her bra and took a minute to stare at Diane's bare tits, right here in front of me after all this time trying to imagine what they looked like under her tight sweaters. She told me to go ahead and lick them, which I quickly obliged her on, slipping one of her rock hard nipples into my mouth and nibbling it as my hands grabbed at her other tit. As I got into a rhythm of sucking on her tits and caressing her body, I felt her small hand reaching for my crotch. I couldn't wait for her bare hand to touch my cock, but I didn't want to help her by unzipping my shorts. I wanted her to do the work and find my hard surprise. She seemed to like this little game, and she eventually used both hands to free my cock. I could tell right away she was very happy with the size. I don't have the longest cock, but it is very thick, and from what I'm told, it's the girth that makes the girls go crazy.

I could see Diane's excitement as she explored my cock and balls, as I made my way down her body with my tongue and my hands. As I came face to face with her crotch, I looked up for approval, in case she was having second thoughts. When I saw pure lust on her face, I knew I could proceed. I slid her sweats down, just enough for me to see her plain white panties, wet with desire. I could smell her hot snatch and I had to have it now. I always envisioned this moment, and how I would take my time to tease her through her panties before touching her pussy. But as we lay here, I wanted nothing more in life than to see and feel her sopping cunt.

I yanked down her panties, and pulled them off along with her sweats. There it was, her golden bush, glistening with juices and begging to be eaten. I buried my face right in, licking her clit and her meaty lips as I rubbed her hairy mound. She released my cock and gripped the sheets as I went to town eating her delicious vagina. I held her legs apart as my tongue tasted every inch of Diane's most private areas. Her eyes remained closed, and almost as soon as I slid my two fingers into her warm hole, she shook with orgasm, soaking my fingers. I wasted no time tasting her juices off my fingers and she tasted great. I was in heaven and so was she, as I started to really fuck her with my fingers. Her pussy quivered and she yelled out incoherent words as she came again. I lay back next to her, tired from making her cum. Diane grabbed my dick again, this time jerking it hard. I inched up on the bed, hinting that I wanted her mouth on my cock. She got the hint as I watched this mother of four's mouth open wide to engulf my hard meat.

She gave it a few long licks up and down, and her small hand played with my balls. As great as her mouth felt on my cock, I HAD to have her now. I pushed her back onto the bed, and climbed between her legs. I leaned down and met her tongue with mine, the same tongues that were just devouring each other's privates. My dick nestled against her still wet pussy lips. It felt all sticky down there and I knew she was going wild with lust. She grinded her pelvis forward, begging to be fucked. I let my dick sit just along her lips until she screamed for me to fuck the shit out of her, like she's never been fucked before. That was all I needed to hear, and I slipped my mushroom head into her body, letting in linger for a moment before she grabbed my dick herself and shoved it deeper. I took the hint and began plowing Diane's older cunt for all I was worth. Her gorgeous titties flopped all over the place as my cock drilled into my biggest desire. Our bodies were covered in sweat, and more, and I pulled out to turn Diane over onto all fours. She smiled at me as I felt for her pussy from behind. I slid in again and we quickly found our rhythm, my groin rubbing her tight ass as her tits hung below us. I got a little adventurous and pulled on her blond mane as I fucked her from behind. She loved it, screaming for my cock to go even deeper into her tiny body.

The cheap bed frame shook and I thought we were going to break the bed. We fucked and fucked and Diane came again. I felt her creamy juices spilling onto my hard cock. Shortly after she came, I gripped her ass tightly and pumped her hard three or four more times before announcing that I was going to cum. When a guy says this, the woman has seconds to decide where she wants it. Diane's lack of telling me to stop, or making me remove my dick meant that she was ok with my huge load getting shot into her sweet mature snatch. I groaned and dug my nails into her ass. I screamed out as I felt my cum shooting out into her, glob after glob filling her hole. She moaned at the feel of my cum inside her, and I reached under her to massage her beautiful tits as my seed began to subside its force within Diane's pussy. I pulled out my cock and let the last drops drip onto her ass. We both collapsed down onto the bed in a mess of sweat and cum.....

bignfirm
bignfirm
340 Followers
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4 Comments
AnonymousAnonymousalmost 13 years ago
Great story

Sometimes u just gotta get lucky

AnonymousAnonymousalmost 15 years ago
GRRRRRREATTTTT!!!!!

I wish I knew someone this sexy when I was younger. Diane is the women of my dreams. Please keep writing about her.

AnonymousAnonymousalmost 15 years ago
Nice

A little abrupt, but hot, quick and dirty, like sex in a desert motel.

vargas111vargas111about 15 years ago
Lacking

With no risk of pregnancy, it just wasn't that exciting.

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