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  • — Sex Confessions —
    Straight Male / 50

    I have known Cheryl for many years, a slightly chubby girl that turned 39yo only a few weeks ago. She does some contract work through our office, she comes in and spends a few hours and then leaves.

    I'm a smoker, so is Cheryl. Sometimes we would meet outside at the smoking area. Cheryl would tell me her life of that day. She was a mother of two with a husband that she suspected was cheating on her.

    I heard about the divorce many months later, the boyfriends that came and went. Not many guys are into a ready made family. Sometimes Cheryl would call me just wanting to talk, hell I had my own problems with the girl I was dating.

    A few months later I noticed Cheryl looked different, she told me she was on a diet and was losing weight. Eight months later, Cheryl not only had a lovely face, she had a body to go with it. She colored her hair, started to wear makeup.

    Well the guys at work began to take notice of her then, always at her desk and bringing her coffee. We used to laugh about it while we smoked. Now I myself would have fucked Cheryl even before she lost weight, even dropped a few hints about it after she divorced her husband. But seeing her now, my thoughts were turning sexual in nature almost every time I talked to her in the smoking area.

    But reality sucks, I was old enough to be Cheryl's dad. If I was thinking about her wanting to fuck me, I was just dreaming and I knew it. I was the father figure, someone she could talk to and that was it, well sometimes the sun shines on a dog's ass when you least expect it!

    It's last Friday about 11pm and I'm thinking about calling it a day, flipping off the tv and turning off the lights, when my cell phone rings. I look at the caller ID and I see Cheryl's name on the screen.

    I answer the phone and there is silence, I'm thinking it's a butt dial. Cheryl had my number because she would call me about her work hours, so she could get paid. Then she says my name and I can tell she's crying. I can't even understand half of the conversation, and I tell her to meet me at the Wells Fargo bank that's not too far from where we both live. She says okay and the call ends.

    I put my shirt on and drive to the back parking lot, Cheryl's car is already there. I pull next to her car and she gets out and meets me as I come around the back. In the shadows of the bank parking lot lights she comes to me and puts her arms around my neck, telling me just to hold her for a while.

    I do it, no idea what's going on. She is trying not to cry into my neck. Suddenly I realize she seems taller, Cheryl is barely 5'2" on a good day. I barely have to lean forward to allow her to hug my neck.

    We stand there until the cops show up. I guess a bank parking lot isn't the best place to meet after banking hours are long over. The cop is really checking us out, an old guy and then I realized how Cheryl was dressed. May as well just say it, she looked like a hooker!

    In the darkness I didn't see what she was wearing, she came at me so quickly I didn't have a chance to see what she was wearing. She wore a nice blouse, but her skirt, the hem was at mid thigh in length. She wore stockings, they looked black, and heels. I mean she was wearing nose bleed heels, now I know why she seemed so tall.

    The cop told us whatever we were doing, we needed to do it someplace else! I started laughing because I knew what he must have been thinking. Cheryl started to explain, the cop didn't want to here it, he told us to move on, period!

    I just said to Cheryl, asking her if she wanted to go to my house and talk. She agreed quickly and she followed me home a few miles away. We got inside and that's when I really got to see Cheryl in her outfit and heels. Yes I looked, and I admit I was drooling inside. She wasn't the plain jane girl I saw at the office, sneakers, stressed jeans, maybe a bit of eye makeup.

    Her face glowed, the makeup, eyeliner, mascara, and lipstick. I never saw Cheryl with lipstick on. Her usually semi messy hair was so nicely styled, it didn't even look like the Cheryl I knew.

    I poured Cheryl a glass of wine and we went outside on the patio to have a smoke. We sat at the table and she told me what was going on. Most of the conversation was a repeat of the ones she shared at work. Another boyfriend that was either jealous as hell because a guy looked at her or that her boyfriend had a issue with alcohol and got stupid with her.

    The latest boyfriend was the jealous type. They had been out, a guy looked at her a bit too long and a fight ensued. The last time she saw the boyfriend, the cops were taking him to jail with a charge of assault and battery. Not only did her hit the guy but he was pissed at Cheryl and put his hand around her throat. She tilted her head upwards, I could see a bruise even in the dim patio lighting.

    So we talked, Cheryl had a couple more glasses of wine. It was almost 2am and Cheryl was a bit buzzed by now. I could take her home or she could sleep in my spare bedroom. Honestly I was shocked when she said she would take the spare bedroom. I had a spare toothbrush and knocked on the guest bathroom door. She opened it up and there in the bright lights of the bathroom stood Cheryl and I know she saw my eyes crawling all over her in a blink of the eye.

    She smiled and thanked me, closing the door, leaving me to my twisted sexual thoughts. I went to my bedroom and closed the door. Brushing my teeth and crawling into bed a few minutes later. My last thought before falling asleep, my cock had this excited tingle. The tingle you get when you know your cock would get hard if a breeze went by.

    I had no idea how long I had been asleep, the bed was moving or something? I opened my eyes to the pitch black bedroom. A body was crawling on top of me, I could smell lilac perfume suddenly. Soft hands on my face, warm lips to mine, pushing them apart as Cheryl's wet tongue pushed into my mouth.

    My hands went around her body, she was still clothed. We kissed like lovers, a deep passionate kiss that made my cock react instantly. Her thick mane of curls tickled my face as we kissed feverishly. My cock was growing by the moment, Cheryl could feel it now, pushing her hips downwards, grinding against it.

    Suddenly she sat up on me, still astride my waist. The only thing between us was the thin blanket. In the darkness I could feel her movements, her hands busy. She removed her blouse and bra a moment later. I raised up on my elbows and buried my face into her ample breasts.

    Cher yl put her hand behind my head, holding me there as I sucked on her nipples. She moaned loudly, I even bit those hard erasers gently and not so gently. She cried out again, letting me know it was wonderful and not to stop.

    My cock was now rock hard and Cheryl pushed her hips downward. She moaned with pleasure just as I was now. I put my hands to her shoulders and rolled her onto the bed, moving quickly I got between her legs. Her heels and stockings were still on, I pushed up that short skirt and pulled her panties down quickly, throwing them into the darkness of the bedroom.

    Spreading her legs, I found the object of my hunger. I went down on Cheryl like a starving animal. She was already wet by the time I pushed my tongue inside of her pussy. No idea how long I was there, Cheryl kept having one orgasm after another. I licked her feverishly, even taking her hard clit between my lips, biting it gently. Cheryl's long nails clawed my scalp and my shoulders, her heels digging into my waist, hips, legs.

    I pulled away and knelt between her legs. I shoved my raging hard on into her drenched pussy like a madman. One thrust and I was balls deep into Cheryl. She cried out, cursed, squirmed below, as I thrust my cock into her brutally. Those long nails raked my back as I leaned over top of her and fucked her with all the leverage I could muster. Those short legs wrapped around my waist and I couldn't hold back, blasting my hot load of cum into her a few moments later.

    I was so pissed with myself, wanting it to last longer. Cheryl lay there soaked in sweat and breathing hard with my spent cock still twitching inside of her. I lowered myself until my bare chest could feel her hard nipples against my skin. We kissed again, thinking about going another round in a little bit.

    Wasn't going to happen, Cheryl said she needed to get home. Her mom was watching her boys and she didn't want to over extend using her mom babysitting. We lay there for a few more minutes before Cheryl slid off the bed. She kicked off her heels, saying she wasn't in any shape to walk in those now.

    She went to the bathroom and freshened up, coming out a few minutes later. I put my jeans on but no shirt and walked Cheryl to her car. She stood on her tip toes to kiss me. I pulled her upwards slightly, another deep kiss like before. I wanted her again, tried to convince her to stay. She smiled at me under the streetlamp, telling me maybe another time? She got into her car and drove down the deserted street.

    Since that night, when I see Cheryl at the smoking area, we really don't talk about what happened. We have these stupid smiles between us, a few innuendos. She hasn't said it was a one time thing, she even sent me a photo text with her wearing a corset and heels a few days ago. Hoping we can make it happen again..........

    #41057 — Comments (1) — Aug 7, 2018 at 1:17 PM — That's Juicy! (8) Remove This.
  • 1
    Yeah man, that's the best kind of sex! Getting that pussy you don't think you have a shot of having. Many years ago I had that happen to me as well. It was a one time deal, but I made the most of it while she was in my bed! Hope you get another shot at it.....

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