Mom’s Best Friend

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Nis 14, 2021 // By:analsex // No Comment

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I’ll start by saying this has nothing to do with my mom, so if you’re looking for something more Oedipus-sy, I wish you the best of luck. This is a quick story about my experience with an older woman.

My mom and Jenna met each other in the hospital while they were giving birth; mom was having my little sister and Jenna was having her first of three children. Despite the age difference – mom was in her early 30s and Jenna was barely 20 – they quickly became good friends, eventually becoming great friends. Jenna and her husband, Rick, became part of our family. Like an aunt and uncle, without any of the blood relations.

We lived in a small town and tended to do things together. Movie nights, BBQs, camping, and even holidays. One of my earliest sexy memories of Jenna was while we were in Mexico at one of those all-inclusive resorts. She’d had a couple of years to get her pre-baby figure back, and she looked amazing. The two of us were at the pool because the rest of our families had taken the ferry to Cozumel. I used to get terrible sea-sickness and Jenna wanted to lay by the pool and soak up the sun, so she suggested the two of us hang out while the rest of the family explored the little island. I had my books and she had a few margaritas. It was looking like it was going to be a very good day.

Being that I was a late bloomer, I’d seen a few of my dad’s stroke books and had a basic idea about sex, but I wasn’t particularly sexually aware. I was 18, but the hormones hadn’t quite kicked in yet.

I guess a bit about Jenna would be appropriate here – back then, she was an Italian goddess. Olive skin, hair so dark brown it was almost black, and a dedication to exercise combined with a superb metabolism had resulted in a near-perfect body. This was in the era of jazzercise and aerobics, so she didn’t have rock-hard abs and buns of steel, rather, soft curves and a toned body. The white bikini she wore showed off her supple skin and fantastic figure. I’m in my 50s now, and still can’t recall a body that amazing.

Jenna and I had been in and out of the pool for most of the afternoon, horsing around. We’d been playing water-basketball and there were a few times where I accidentally bumped her while trying to block a shot, or she’d do the same to me. Nothing major, but a young guy isn’t going to forget the first time a strange boob brushes against his arm – hell, any contact with the opposite sex was memorable. Eventually we got out and after a quick bite decided to sit and enjoy the sun for a while. My mom was paranoid about skin cancer, so I was well trained at making sure I was slathered in sunscreen regularly. I covered my arms, neck, chest, and legs before awkwardly trying to cover my back. That’s when Jenna took the bottle from me and rubbed it into my skin. It was amazing. The touch of her hands on my skin…exquisite. And then to make matters worse, she proceeded to squeeze out more lotion to ensure she was adequately covered.

She poured the lotion into her hands and began applying it to her long, luscious legs. She bent over to reach her shins and calves, giving me an incredible view of her more-than-ample cleavage as it strained against the flimsy material of her bikini top. As she moved up her legs, she gave me a polite smile as she caught me staring at her. I blushed and looked away, only to see that pretty much every guy on the pool deck was straining to watch her put on the sunscreen. Some of them were trying to be discreet, watching out of the corner of their eye to avoid confrontation with their wives, while others were openly ataşehir escort bayan ogling her. I laughed and tried hard not to look at her again, but apparently my hormones had finally kicked in and I soon found myself watching as her hands crossed her tight tummy and made their way to the land of underboob. She had her eyes closed as she applied the lotion, covering her body with the invisible sun barrier. Her hands moved with the natural motions that come from doing a task numerous times, and before long she was rubbing the last of the lotion into her face, smiling at me while she did it. With a bit of lotion on her finger, she tapped me on the nose to break me out of my trance.

“Would you mind putting some on my back for me?”

I knew she asked me, but it was funny to see four of the guys closest to us to jump out of their seats. Apparently everyone is a gentleman.

Jenna moved the lounge chair into the reclined position, and then turned over to give me access to her back. She jumped a bit when I squirted the cool lotion directly onto her back, but soon relaxed and let me caress her skin with my inexperienced hands. As I moved up to the strap of her bikini, she reached behind and undid the bow.

“I’ll just undo this so I don’t get any tan lines,’ she said.

I certainly wasn’t going to argue, so I continued to apply the sunscreen, enjoying my first experience of touching an actual woman. By the time I was done, I had a major tent pole situation and no clue what to do with it or how to hide it. I grabbed my book and smashed it against my swim trunks, painfully subduing the growing monster in my shorts, then excused myself to go back to my room. Jenna lazily nodded to me before drifting off to sleep in the hot sun. And that was the day I learned about the joy of masturbation, and to this day I will occasionally dip into that memory for inspiration.

It must have been a great trip for Jenna and Rick as well, as about nine months later their daughter was born.

Since it was a small town and we were nearly neighbors, I was often requested to babysit for Jenna. This was a dream come true for a horny eighteen year old – staying in the home of your crush and getting paid for it. Hell yeah I was “up” for the job. Looking back, I know it was wrong, but I explored every aspect of their home while they were out and the kids were asleep. I rubbed one out on more than one occasion thanks to her sexy underwear drawer, and the day I found their selection of toys I just about shot a load in my pants. Being that close to the selection of vibrators, dildos, and nipple clamps that I knew had been on – and in – her incredible body was painfully enjoyable. I picked each magical item up and brought it to my nose, detecting a faint hint of her natural perfume and burning more memories into my limitless spankbank. The week after I found her toy chest I could barely walk, as I must have taken advantage of myself ten times a day, each better than the last. Ahh, to be 19 again.

Time went by but my crush for Jenna never wavered. I’d dated a few girls in town, but I was still a virgin. Even though I had just entered my twenties, I still babysat for Jenna and Rick whenever possible, and fantasized about her at least once per week, usually more often. This was pre-internet days, so a man’s imagination was still a powerful thing.

The phone rang at my house one afternoon and my mom answered it. I heard her talking to Jenna for a few minutes, and then ending with a, “I’ll send him right over.” Apparently she needed some help moving escort kadıköy furniture, and since Rick had taken the kids out of town, she wanted to know if I could lend a hand.

I don’t think my feet touched the ground as I sprinted to help her.

I knocked and waited for the, “Come in,” before entering. I could hear that she was down the hall.

“I’m down here, Chris – can you please give me a hand?”

I gulped and walked towards the bedroom, my horny mind willing to make Faustian deals just for the opportunity to catch a peek of her while she was changing. I was not prepared for what I was about to find.

Jenna was lying on her bed wearing a black negligee and a smile as I walked into the room. I froze in my tracks, and I’m pretty sure my jaw bounced off my chest. She patted the spot beside her, and beckoned me to her side.

“Chris, since I didn’t get you a gift for your twentieth birthday, I was hoping there was something I could do to make it up to you.” she said.

I was dumbstruck and couldn’t say a word, but I kicked off my shoes and walked to the bed to sit beside her.

She took my hand, giving my palm a gentle kiss.

“You’ve always been a good boy, and I see you’ve turned into a good looking man,” she said. “I don’t think we’re going to have another opportunity to do this, but if you’re willing to learn a few things from an old lady, I’m willing to teach you. But this is a one-time only experience, and you can’t go blabbing about it to all your friends.”

My tongue was too tied to form actual words, so I just smiled and nodded.

“Ok, now, are you still a virgin?”

I nodded.

“Good, you don’t have any bad habits yet then. Ok, well, let’s get the first one out of the way. I can see that you’re just about ready to burst.”

And with that, she reached down to my waist and undid my belt and jeans. She hooked her fingers into my waistband and pulled my pants and underwear down around my knees in one swift motion. She leaned closer, taking my swollen cock in her hands. As soon as her soft fingers embraced my raging hard on, I exploded. I could have won an award for volume and distance as ropes of steamy cum shot out of me. Some landed on the bed spread, the carpet, and I think I even got some on the wall across from us. I was embarrassed to cum so early, but Jenna giggled and then guided my still-twitching cock into her mouth. I felt her tongue swirl around me and moments later I unleashed another volley of man juice down her throat.

She backed away, licking her lips and smiling at me.

“Ok, that should ease some of the pressure, now let’s get down to the fun stuff,” she said.

And that’s when my instruction began. Jenna guided me through everything she knew about sex, and in my opinion, she knew a helluva lot. We began with kissing and touching – deep passionate tongue kisses while our hands roamed. She guided my hands over her body, showing me how to tease her nipples to attention, and then bringing my fingers down to the warm and wet valley between her legs. She whispered in my ear how to use my fingers to pleasure her, explaining when to speed up and when to slow down. With every orgasm that rocked through her – and I quickly became aware as to when she was having one – I felt the shudder of her body all the way to the base of my straining cock. I’d already cum hard twice, but I was aching for release yet again. While I was teasing her with my fingers, Jenna guided my mouth down her neck and into her delicious cleavage, Another tremble coursed through her when I took bostancı escort a nipple in my mouth, and yet another when I lightly bit at the dark brown nub.

We paused for a moment, both out of breath and not saying a word. She pushed me back on the bed and manoeuvered herself so there was a knee on either side of my head. She bent forward and took my cock in her mouth again, and without any urging I brought my tongue to her delicious pussy. I buried my face between her wet folds and licked and sucked everything I could find. I noticed that certain areas brought an immediate response from her body, so I made sure to focus on them and help her ride through another course of orgasms. As I was sucking on her clit, I moved my hand up and slipped a few fingers into her, letting my digits fuck her as my tongue focused on her obviously sensitive clit. It was difficult to focus, as I could feel her sucking and licking my rock hard cock. I was able to last a bit longer this time, but eventually shot another load into her mouth. After she finished swallowing it all, she turned around and came face to face with me, bringing her mouth to mine. I tasted the cum on her lips as she forced her sticky tongue into my mouth, but this wasn’t the first time I’d tasted my own juices – after our trip to Mexico, let’s just say I found something to do with my free time.

While we kissed, Jenna moved her hand between my legs to grab onto my still swollen cock. She guided me into her pussy and began a gentle rocking while she sat on top of me. I bucked my hips in time with her movements, feeling her hot body wrap itself around my hard shaft until I felt her stiffen then begin to quiver as another orgasm raced through her. I slowed my pace to give her a rest, but when she whispered, “I want to feel your cum deep inside me,” I sped up. Being that this was my first time, I had pretty much no control, and in spite of the previous releases, I was ready to blow in seconds. I slammed my pelvis against hers, rocking my hips so hard that days later I could feel the strained muscles throughout my body. I felt the eruption and gasped as I unloaded it deep inside her. We collapsed on the bed, a heap of tangled limbs. Sticky with sweat and juices, we lay for a moment before we both nodded off to sleep.

We awoke an hour or so later, and Jenna suggested we should have a shower to “freshen up.” That led to even more fun, and I think I emptied the last of my sperm reserves about the same time we ran out of hot water.

While we dried off, Jenna said, “You should get going home now. Your mom is going to think I’ve abducted you. I know I said this was a one-time event, but maybe you can stop by tomorrow and I’ll teach you a few more tricks.”

I gulped and nodded, and made a mental note to stock up on Gatorade.

That summer, Jenna continued to teach me whenever we had the time to be alone together, but by late fall we knew it was coming to an end. She was pregnant again, and she told me it was her husband’s child, not mine. I didn’t know enough about anatomy yet to know if she was telling me the truth, but I couldn’t think of a reason as to why she’d lie about something like that. They named the baby Kristina.

Jenna and I kept in touch over the years, and while we didn’t hook up as often as I’d hoped, we still managed to enjoy each other’s’ company on more than one occasion. I asked her once if Kristina was my child, and Jenna just smiled at me and said, “Rick is her father, and always will be. Let’s just say you were her inspiration.”

Jenna passed away last summer, but she has always been the yardstick I measure all relationships against. I’ve never been with another woman as sexually powerful as Jenna was, but the tricks she showed me that summer made sure I was able to find enough willing victims to make a fair comparison.

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