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Author's note: These are the tales of my journey from an unhappily married man to a very sexually active single/divorced man. These stories are based on true events and relationships, although the quotes may not be verbatim. All events are generally stated as best as I can recall, with some embellishment or artistic license as needed, especially considering I am writing this 20 years after the events of the first story. But the substance of each story is true.
I wrote these stories in chronological order but didn't title them very well. If you want to read them in order you have to start with "Middle Aged Male Sex Chronicles 01" and follow them by date of publication.
Everyone was over 18. Names and places have been changed or hidden to protect identities and privacy.
You may see references to other people or events in my stories, seemingly out of context. I've written all my stories as a chronological account of my life after divorce, but each story stands on it's own unless noted as a new part or chapter.
Ally
A friend of mine has three kids, the youngest of which is the same age as my oldest. His oldest is a girl five years older than them. Her name is Ally, and I've known her since I met her father when she was a toddler.
This guy likes to drink on his back deck almost every night, for sure every weekend, so he can always be found there. Every couple of weeks I'd go over there, and of course his kids, including Ally, and their friends were always running around in the yard and the pool. Ally and I always connected very well even when she was very young.
Over the years, we did a lot of things together with this family, pre and post-divorce -- hikes and bike rides and a couple vacations. My kids, Ally's siblings, and all the friends always joked that Ally had a crush on me, which was funny and cute.
I watched Ally blossom from a chubby gap-toothed kid into a beautiful athletic high school homecoming queen.
Ally went off to college, and I saw her on occasion the first two years, usually at holidays when I'd wander over for a drink and she'd be home on break. She was getting more beautiful as time went on.
Her last two years of school, she almost never came home, having gotten a job at the college, so she spent most of her time there working when she wasn't in class. She came home for an occasional holiday but only for a day or two, then right back, and I didn't see her on those occasions when I went to visit her dad.
As such, I didn't see Ally for about a year and a half. Once in a while I would see a social media post, and it looked like she had a boyfriend. One of my kids even screen-shotted one of these pics and sent it to me, saying, "I guess she's over you lol!" in a fun teasing way.
As the spring of her senior year approached, I was invited over for a graduation party for Ally at her house. This was soon after Tina had left (see "Forecast Calls for Sex"), so I was pretty down in the dumps, despite my continued fun with Jennifer and Susan (see "Soccer Moms" stories).
I arrived at the party and was in the living room talking to another guest, when Ally walked down the stairs, and I'm telling you she looked like an angel. My mood brightened immediately. I hadn't seen her in about a year and a half, and whatever she did for that time, it was working. Now 22 (I was 54), I can't remember ever being more stunned by someone.
She saw me and her eyes lit up!! She ran over and gave me a big hug. She smelled like dream and looked like a wet dream. Not tall and thin, but maybe 5'5" and with a fullish figure. She played college lacrosse and was just a tad on the curvy side. Not big boobs, but a bigger, muscular ass with a perfect shape.
Ignoring some of the other guests, we talked for a good 15 minutes before her mom came looking for her and pulled her away for some distant relatives to gush over her.
The rest of the party went as normal. Some of Ally's friends came and chatted with me, as I had known them for years as well from them just hanging around the house and pool, and of course they knew that Ally once had an innocent crush on me.
One of them even said, "Hey since you're divorced and she's legal, you should go for it," and they all cracked up laughing.
All in all it was a good time, and later that night I took care of myself with thoughts of Ally's gorgeous, now womanly body making love to mine.
Maybe two weeks later, I got a private message from her on Instagram. (We didn't have each other's cell numbers). She wondered if we might have a drink, she needed some advice and couldn't ask her dad.
Of course that was fine, so we met on Memorial Day Saturday early evening at a bar located just a short distance away. I figured Adana Escort if we were spotted 30 miles away, it would look very suspicious, versus closer to home where it might look more like we just bumped into each other.
We hugged again upon seeing each other, and we picked up the conversation where we had left it at her party. Small talk about her sports career and plans after graduation.
Finally I said, "OK my dear, how can I help you?"
She said, "Well, you might know, or maybe not, but I've been dating this guy that I met in college."
"Yes," I said, "I had heard that, how is he?"
"Well, that's the problem, he's not great. I mean, he's great, but he's not the greatest, you know, cocksman."
I almost spit out my drink! I haven't heard anyone use that term in a gazillion years in normal conversation, especially not a 22 year old female, nor was I expecting this from her at that moment.
She laughed and said, "I didn't know how else to say it without being crude!"
I said, "Ally, trust me you can be crude with me. Speak freely, I'm impossible to offend or embarrass."
She said, "Well, I mean it's fine and everything, but he just finishes so fast, and when he's down on me, you know, eating me, it's like he is maybe trying too hard. Plus, you know I don't have a lot of experience either, so for all I know he's thinking the same thing about me when I'm down on him."
"So what is the advice you need from me then?" I inquired.
"I guess I just need to know if you could teach me how to please a man. I can't ask my mom for tips, she thinks I'm still a virgin. And there's no way I could go to my dad on this, obviously. I've heard that older guys are experts at sex, with all the experience they've had over the years. We've known each other a long time and I trust you, plus I know you'd never tell anyone or my dad would kill you. So it seems like you'd be the perfect person to help me."
This was sounding like she needed more than advice.
I said, "So when you say 'teach' you, what do you mean by that?"
I wanted to be clear what was being asked so as not to get myself into trouble.
"You know," she said, "teach me. Show me how to please a man, and how a man should please me so I know what to expect and insist on."
"So," I finished for her, "You want me and you to actually do these things to each other?"
"Yes that's what I'm saying. Look, it's no secret that I've always had a thing for you, and still do. You've only gotten better looking, and I'm sure you can show me what great sex is supposed to be like."
"Ally," I said. "Great sex is as much about emotion as anything. Having feelings for someone is what makes sex great, and the more intense the feelings, the better. If the feelings are there, then communication about what you like and don't like is easy, and fun. Maybe this should tell you something about your feelings for this guy, if you aren't having great sex and can't find a way to talk about it. There, that's my advice."
I was proud of myself for taking this road. Giving fatherly advice as needed instead of picking the low hanging fruit and just fucking this vixen.
She sighed, and said, "Yes, I know all that. Dammit why are you making this so hard. I want to fuck you. You turn me on, and my boyfriend, if you can call him that, can't please me and is halfway across the country right now anyway. I've wanted to fuck you since I was old enough to know what sex was, and I've fingered my pussy raw a thousand times thinking about you."
Well, this was a different story. She was no longer the shy, bashful young lady I knew since before she had braces. She was all business on this issue. This was setting itself up so nicely. It was like I won the lottery without even buying a ticket.
I took a final slug of my drink and took her hands in mine. I said, "Ally, I'd love to help you. I've always thought the world of you, and you are now a beautiful young lady, so anything I can do to make your life better, I'm happy to do."
She responded with a big hug, and said "Thank you sooooo much! When can we get started. Wanna go right now?"
I wasn't expecting that, and had to think quickly as to what kind of shape my house was in. Had I left any dirty underwear around etc. Or worse, did Jennifer or Susan leave any of their underwear behind. My kids were away with their mom so that wasn't an issue. I couldn't be sure, but was willing to take the chance. I'm usually a pretty tidy person, and I didn't want to lose momentum here.
"Check please," I said, and she laughed.
"See!" she said, "You want this too!"
Couldn't argue with her there.
Ally followed me back to my place, and pulled her Adana Escort Bayan car into the garage. I opened the door and let her in in front of me, all the while my head spinning as I thought about how this would proceed. Would it be clinical, like a teacher-student situation, with me first giving a lecture and then moving to the lab for "practical application"? Or would it be more like an experiment, like a med student working on a cadaver and the professor explaining and giving instructions as things progressed. I didn't know what to do.
Ally answered those questions when she spun around as soon as we entered my house, wrapped her arms around my neck and planted a kiss on me that sent sparks flying. Her hands went to my ass and she worked her tongue into my mouth, and there was little doubt what this girl was after.
She pulled back for a second and said, "I've thought about this moment for 8 years, and it's finally here!"
She pulled me into the house, found my living room and threw me on the sofa, mounting me and grinding on me while she continued to feverishly kiss me. We pulled each other's tops off, and her braless 22 year old tits spilled into my hands.
Her tits were perfect. Not overly large, so firm yet soft at the same time. Pointy hard pink nipples that cried out to be pinched nibbled on, and I answered the call.
I slobbered on her tits while she kept grinding me. Finally I threw her onto the floor and ripped her leather mini skirt off, finding her pantie-less and shaved bare like a newborn. Whatever I thought a 22 year old pussy would look like was blown away by what I actually encountered. An absolute work of art, puffy pink lips glistening with juice, slightly open from arousal, not a hair or a pimple or a wrinkle or blemish to be found anywhere. Some otherworldly being made this vagina, and I was about to be the benefactor of the creation.
As much as I wanted to dive in and attack this pussy paradise, I wanted to take her to new heights. I was sure that her boyfriend didn't have the tricks up his sleeve that I did. She said he fumbled around a bit, so I took my time, using my tongue and fingers in concert, teasing and flicking her swollen clit, sucking her meat into my mouth, licking from the absolute bottom near her asshole and all the way up to the top, with my nose penetrating her pussy when I was down that low.
I even let my tongue touch her asshole for a millisecond, which sent her into orbit. Of course I would explore that with her over time, but for now I was focused only on her pussy, her pleasure, and giving her things she'd never had. I reached up and pinched a nipple on occasion, I looked right into her eyes as I put my tongue way up inside her. She looked confused, but then outright hungry, when I stuck a wet finger in her mouth to taste her own pussy juices.
I brought her to three orgasms this way, finally pulling up and kneeling over her as she laid on the floor spent.
I knelt over her and watched her spent body recover.
She slowly opened her eyes and said, "Oh. My. God!!! Is that the way it's supposed to be every time?"
I replied, "For your sake, I hope so. Oral sex should be done with passion and enthusiasm. No one wants to get oral if they feel like the other person is doing it as a chore. You have to love doing it, and the receiver should know that the giver is just as into it as the receiver. Make sense?"
I was pulling down my shorts as we spoke. I'm not sure if she heard me or not, because she was focused on my crotch as my shorts came down and my dick sprang into view. My cock was fully hard, and her eyes got wide when she saw it.
She looked at me and said, "I've seen a half a dozen dicks or so, but none like that."
She sat up and wrapped her hand around it, continuing, "It's amazing the difference between a man's dick and a boy's dick. It just looks so, I don't know, manly."
She stroked it a few times, pumping it with her hand enclosed around my shaft, staring at it as she did. She changed tactics and lightly ran just her fingertips up and down my shaft, then traced the big blue vein with just the tip of her index finger.
"How big is it?" she asked?
"Almost eight inches," I replied.
She looked up at me, her big brown eyes looking so innocent.
"Is that normal?"
"I always thought that was pretty normal," I answered. "But I'm learning over the last few years that it's a little bigger than normal."
I was throbbing, a large dollop of precum forming and starting to drip. She noticed and caught some with her finger.
"Is this cum?" she asked innocently.
"It's called pre-cum," I answered. "Taste it."
She scooped up as much as she could and put Escort Adana it in her mouth.
"Mmmm, salty and sweet at the same time. Can I have more?" she asked.
I showed her how to squeeze my cock, almost like a tube of toothpaste, to coax more precum out of my shaft. She giggled, "Oh wow, that's so cool."
She milked as much pre-cum from me as she could, while I explained that while this wasn't exactly cum, it still contained sperm (well, not mine anymore) so the pullout method was not always the best birth control. She was on the pill, she said, but that was good information to know.
Finally I said, "Lay back."
She looked a bit surprised, and asked, "Don't you want me to suck your dick?"
"Not right now," I replied, "We'll get to that, don't you worry."
"Are you going to fuck me now? God I've dreamed of this moment. I kind of wish I was still a virgin, but also kind of glad that I'm not. That thing would scare the hell out of me!"
Ally laid back and opened her legs. I touched her with my fingers, confirming that she was still very wet and ready for my cock. I poised myself over her, grabbing my dick in my hand and rubbing the head up and down her slit a few times. She shuddered each time I hit her clit. Slowly my cock head started to penetrate her.
As much as I wanted to watch my cock sink into this prime pussy, I had to watch her face, her eyes, and her mouth as I slowly pushed my meat into her. Ally's eyes rolled back in her head and her mouth opened in a silent groan as I hit about three quarters, and then the silent groan turned audible as I reached full penetration.
I held myself in that full penetration position for a couple seconds, just to watch her face and allow her to get used to the size.
She froze for a second, gripping my biceps and digging her nails into my flesh.
Then she whispered, "As soon as you move, I'm going to come."
Sure enough, all I did was shift my weight upwards to change the angle slightly, and she let loose. "Oh God I'm coming, fuck me please."
I started moving in and out, thrusting with slow but firm strokes as she fought through her orgasm. She moved her legs back and forth, feet in the air, as I thrusted. She had mentioned before that her boyfriend seemed to finish too quickly, so I was determined to give her a prolonged fucking.
Problem was, in addition to being so damn sexy, and watching her facial expressions and tits bouncing was such a turn on, she was just so damn tight! I knew that once I got her legs up on my shoulders or got her knees locked behind my elbows, that would be all she wrote. So I persisted with the position we were in, trying to think of anything that would keep me from coming. What's the saying, think about baseball? I was thinking about every sport there is while I fucked her.
I don't know how I was able to hold out so long, but I managed to fuck her through two more orgasms. She was a damn orgasm machine. When I was ready to plant a load in her, I sat back and watched my cock go in and out of her, and let some spit drool onto her cunt for some extra lubrication, and grabbed her hand to rub it around.
Finally I put her legs on my shoulders and leaned forward, fucking her now with purposeful strokes, pounding her pussy while she gasped for air. She would not soon forget this experience, I could promise you that. I rose up onto the balls of my feet and straightened my legs, getting great leverage on the floor and really wailing on her.
I slowed just a bit and said, "Open your mouth."
She complied, and I let some saliva drool out of my mouth and into hers.
She clamped her nails into my back and said "Oh God, that's so hot."
Then I said, "Ally, I'm going to come. I'm gonna come inside you, are you ready?"
"Oh yes, please, please come," she begged.
I unloaded into her, forcing myself as deep as I could. It was the most wonderful feeling to see the look on this young lady's face when she felt my hot cum bathing the inside of her pussy. She gripped me tight and held on for dear life while I throbbed inside of her.
Eventually I let her legs drop, and we were both a little shaky from the experience. I kissed her a few more times and rolled off of her, grabbing a throw blanket from the couch and covering us as we laid on the floor. We laid in silence, quietly reliving the experience.
"Wow," she finally said. "There's no way it can get better than that, can it?"
"Well," I agreed, "that was pretty damn good. But there is so much more to come. We've really just scratched the surface."
Ally rolled onto her side and threw an arm across my chest, kissed me on the cheek and said, "I want to scratch it ALL!"
We dressed and Ally left with a kiss soon after, wanting to get home so as not to raise any suspicions.
As she walked out the door she said, "Tomorrow I want to suck your dick and taste your cum."
Who was I to argue?
Next part coming very soon. Please comment, I enjoy them all.