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My first time with an older woman
By: Dude143 (story_vote143@hotmail.com)I had an interesting experience with an older woman once that I would like to share with you. in fact, was a friend of my parents, a woman who was old enough to be my mom. It happened in the summer of 1998. I was fresh out of high school and working a summer job. My parents decided to take a trip to Florida and because I couldn’t get the time off of work, I couldn’t go. I was a bit angry about it, but this experience I’m going to tell you about surely made up for it.
I was pretty sure that word had gotten around to all of my parent’s friends that my parents were going out of town for a while, but still, their friend Margaret showed up two days after they left.
She had always been nice to me, and plus this woman was a total knockout. Aside from the fact that her face showed some mild signs of age, she had a nice tight body, a petite frame and her breasts were a thing of beauty. They must have been a D Cup and from the looks of them they were still nice and firm. Her ass had a nice curve to it too. It was one of those that just begged to be grabbed. This was a woman who rode a mountain bike everywhere she went, so she was in excellent shape.
Needless to say, I was happy to see her just for the eye candy factor, though I wasn’t figuring it would ever go past that. She had been wearing a pair of black riding shorts (the skin tight kind), and a long sleeve t-shirt. Her outfit was finished off with a simple pair of tennis shoes.
She had a bit of a sad expression on her face and her head was hanging low. From what my parents said, she had apparently just gone through a breakup a few months prior, and had been coming over a lot to visit my parents lately. Happy as I was to see her, I was a bit put off by the thought of having to entertain my parents’ friend, but I decided to answer the door.
The moment I opened the door, she said, hi, I need some company. Mind if I come in? I stepped aside and motioned for her to enter. She brought her bike in and parked it where she always does when she comes over, and walked in. I’m sorry for just showing up like this. Is this a good time?
Because if its not… she trailed off.
No, it’s alright. I was actually thinking of watching a movie or something in a little bit, I said. You got any ideas? we discussed a few options for a movie as we made our way into the family room. I lagged a few paces behind her to get a look at the sexy sway of her hips and ass, and I felt my cock stir meanwhile. Oh man it would have been so easy to just reach out and grab her ass right then and there, but I shoved my hands into my pockets to resist the urge.
After a short exchange, we decided on a murder mystery movie. I made some popcorn and we sat down to watch. The movie was a bit on the boring side, but sitting on just the opposite end of the couch from her afforded me a chance to steal plenty of peeks at her. I even swear she caught me looking at her a few times.
After the movie ended, we sat there talking casually about what each of us thought about the movie, and how I thought they could have done better to fill in the plot holes. We went on to watch the deleted scenes, and partway through that Margaret asked me if our Jacuzzi had been fixed yet. The motor had seized up on us a while ago, and we had just gotten it replaced last week.
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The motor is brand new, and we even got the stronger one this time, I said. in fact I just cleaned it earlier this morning.Feel like taking a dip? she asked me. I could use one myself. My back has been bothering me a bit older couple sex stories
Sounds good to me, I said, trying not to sound overly eager. I think I did a fair job of sounding casual.
I brought my suit so I guess I will just go and change, she said, while standing up and walking over to her bike in the other room. I heard her undo a zipper pouch that I guess was on her bike, and I headed into the other room where she was. I figured I would get a glimpse of what her bathing suit looked like before she put it on. By the time I got into the room, I heard the door of the guest bathroom close and lock. I decided that I better go and change into my board shorts and get the Jacuzzi uncovered while I was waiting for her.
After changing quickly and heading into the pool room, where our indoor pool and Jacuzzi were, I turned on the lights, and started the pump running.
The water was a nice 100 degrees and it smelled nice and clean. I decided against incense or anything else, but instead put on a radio station that played 60′s music. I dashed quickly into my bedroom and grabbed a couple of condoms just to be on the safe side, and stashed them in the pocket of my robe that was hanging within reach of the Jacuzzi.
As Margaret entered the room, Break on through, by the doors was playing, and she had her eyes closed, she was nodding her head to the music and singing along. What a sight she was. There she stood in a teal bikini, a nice head to toe tan, and even a pierced belly button. The bikini wasn’t as skimpy as I would have liked it to be, but even still, she wore it well, and I must say she looked fucking hot. I was glad I had already climbed into the water before she came in because I was instantly hard at the sight of her. I love this song!’ she said as she stepped into the water herself.
What happened for a moment was what I could best describe as an awkward silence.
We sat there, looking at each other, and she finally broke the tension by sighing, and leaning hear head against one of the side pillows while closing her eyes. so your back has been bothering you, you say? I asked to break the silence.
Yeah. I have a few sore spots and the water helps them a little bit. I guess I’ve just been… stressed lately. The way she paused before saying ‘stressed’ got my attention. I think it was more like sexual frustration from the looks of her.
Yeah, I know what that’s like, I said, trying to empathize. This water helps when I need to relax. I could spend hours in here, I saw a bit of a devious grin spread across her face for a second and then disappear, then her eyes opened for a moment, looking at me.
How are you at giving back massages? she asked me.
I’ve been told I’m pretty good at it. You want me to give you one? I asked her. Well at least I get to feel her back, and maybe check out her ass a little closer while I’m doing it, I thought to myself. The Jacuzzi is a square shaped one with five places to sit with jets on your back and then against the back wall there is a flat spot where you can lay down under water, and still have your head above water. I motioned to this spot while I told her that it would probably be better if she lay down for this.
okay, she said. She partly swam and partly climbed over to the flat area. My God she looked so sexy while she did that.
I was starting to wonder if maybe she was trying to tease me. I did a quick recap of the details of what’s been going on in my mind. She comes over a lot to visit my parents, my parents go out of town and she shows up, saying she needs company, and wants to hang out with me. Then she wants to go into the Jacuzzi with me while wearing a sexy bikini, and now she is asking me for a back massage. All of this seems like something that is a little out of character for someone who isn’t trying to take this somewhere. But I had decided to play along and let her lead this game. Who knows where this might lead, I thought to myself, watching her lay there as I approached to start rubbing her back.
I had a raging hard-on at this point, and I was partially hoping she would notice it and partially hoping she wouldn’t. I tried to hide it the best I could by kneeling under water, but it was no use. I discreetly re-adjusted it so it wouldn’t be poking straight out, and stood up so I could better reach her.
Her muscles were tense up in the shoulders and I did the best I could to massage them. She liked me to put lots of pressure on them, so I was soon leaning most of my body weight on her while rubbing. She was groaning the whole time and that was just turning me on even more. As I made my way down her back, lower and lower, she asked me to gradually lighten up until I was applying barely any pressure once I got to the small of her back. I stopped when I reached the top of her bikini bottom, figuring that was a good place.
In a dreamy voice, she cooed, that was great. Why don’t you keep going?
You… don’t mind? I asked her as I gradually slid my hands a bit closer to her ass.
Go ahead, you’ve earned it, she said in a serious but sly voice. I reached down and cupped my hands over her ass, and she arched her back and tipped it up a little bit, showing off its nice shape a bit more. I put my right hand under the seat of it and gave it a nice gentle squeeze. You’re an ass man, aren’t you? she asked, still in that sly tone.
Yeah, I am, I admitted and I like yours. I hoped that didn’t sound too cheesy. At this point all my blood was rushing away from my head and going elsewhere. come over and sit with me, I suggested, giving her ass another squeeze, then I stood up and offered her my hand. I made no effort to hide the fact that I was hard at that point. In a moment we were standing face to face looking at each other.
I thought we were going to sit, she said with a chuckle.
She gently pushed me down into one of the seats and then sat down on top of me, resting her hips against mine. I cupped both hands under her ass, and kept them there while she slowly rocked her hips against me for a moment, and began kissing me passionately.
I’ve wanted you for a long time, she said to me with a lusty look in her eyes. I casually reached up to my robe and pulled out a condom. She looked at me and smiled. I was just about to ask if you had any. I brought some too. We kissed some more while we explored each other’s bodies with greedy hands. Before too long we had both somehow removed each other’s swimsuits, and they were tossed aside.
I lifted her upwards slightly, and she took my cue to stood up. I propped my head up against one of the side pillows of the Jacuzzi and grinned at her. She knew what I wanted her to do, though I was surprised at how she got into position. She climbed up onto the edge of the Jacuzzi and squatted down above me, lowering her nice soft muff onto my face. I immediately set to work licking and sucking her. she had nice soft labia lips that parted easily with my tongue, and her clit was very responsive to the attention I was giving it. She stayed over me for quite a while, giving me ample chance to enjoy myself. She loved it.
I want you inside of me, she said through husky breath. She lifted herself up from my face and gracefully slid back into the water.
I stood up momentarily, unwrapped and put on the condom. A moment later she was pulling me into the water again. She hugged her body to mine and started rocking her hips, then with what seemed like a carefully practiced maneuver, she lifted one leg up and guided my cock inside of her. I was now sitting on the edge of the seat in the Jacuzzi, with her straddling me. she began rocking her hips with a rhythm that told of experience. It was wonderful. She was so sexy, and so beautiful, and here I was, fucking her.
I sat back and relaxed as we continued to fuck passionately. I fully intended on enjoying this moment. After a while we changed position so that she was laying back on the seat with her head above the water while I fucked her in the missionary position.
She wrapped her legs around me, and made no effort to stifle the moans she was letting out. I began rubbing her clit to add to the experience, and her eyes flew open for a moment, and then squeezed shut. I felt her vaginal muscles contract, and tighten around my penis, and she cried out. I had no doubt that she was having an orgasm.
I continued my thrusting, and started rubbing her clit with my thumb while doing it, and she seemed to like that. She tightened her legs around me slightly, though still left me room to move. Her eyes had been squeezed shut but she opened them, and looked me straight in the eyes, while my climax approached. I had one of those head-spinning orgasms, and she smiled at me.
I shuddered and couldn’t help but roll my eyes back and arch my back. She was doing something with her vaginal muscles that prolonged my orgasm for a few moments. I reluctantly pulled out of her and let out a satisfied sigh. after a brief pause, I got up, removed the condom, stuffing it back into the wrapper and slid back into the water. This is what I needed, she said with a satisfied grin. I needed a good lay with a hot guy like you! she cuddled close to me and hugged me. I shifted myself slightly and kissed her.
Lets do this again sometime, I said to her.
oh, you bet! she answered.
And that was the start of a wonderful secret affair that I had with Margaret, that continued until I had to move away to college. She has since moved on and married some guy who owns a Harley shop, but that is just how life goes.
I hope you have enjoyed this story. Please leave me feedback. I hearing what people think
