I've been involved with many different ladies over the years. Some of them were a passing fancy that faded quickly from memory in all but name, others had a lasting impression that still impact me today in their subtle ways. Ms. Weston was quite possibly the most important of them all. I'm not entirely sure what brings her to mind today, but I wanted to get these memories down here in my journal to preserve them in as much detail as I can manage.
It was in my university years. I was in my early twenties and the second year of a business major. I was a good enough student to keep my parents off my back, but I had yet to find any real sense of motivation that would push me out of my childish youth and into the realities of adult life.
Spring was in full swing and I was enjoying some much-needed time off school on a reading week. My parents were generous people and we got along well when I was home. They were trusting and I was usually respectful enough not to break that trust. Little gestures went a long way with them so I was quick to offer my help when it was needed. It was yardwork for my parents that initially brought me closer to Ms. Weston.
My parents moved to a new part of town during my high-school years. I had only met a few people in the new neighborhood before I moved away after graduating high school. I had met Mr. and Mrs. Weston once as a couple, Mr. Weston died unexpectedly of a heart condition sometime in my final year of high school and it wasn't until after the funeral that my parents and her were truly friends.
She had been widowed for about two years or so when she and I would get to know each other better. From what I heard from my parents, she had been dealing with the loss of her husband fairly well, about as well as could be expected I guess. She was smart, witty, and a genuine pleasure to talk to. She was also very funny and had a surprisingly dirty sense of humor for someone who seemed so proper. I enjoyed her company from the start, she had a way of making one feel that they had known her for years and it always made me feel comforted in her presence.
My parents usually made a point to help her out whenever she needed it after the death of her husband. She had a big backyard with several large trees that would cover her lawn with leaves. Normally my parents would come over to help her, but that year they found a good deal on plane tickets and were on an unexpected vacation. They volunteered my help since I was off school on a reading week. It was a warm spring day when our first incident would occur.
I wasn't overly thrilled about having to work on my day off while walking over but those feelings left me when I arrived. She seemed eager for some company and was in a talkative mood. She enjoyed living vicariously through the wild party stories of my youth, she relished every crazy and raunchy twist. I went into graphic detail at times to test her limits but she laughed heartily and only gave me an 'atta-boy' response that I would have expected from one of my uncles, but not Ms. Weston.
After an hour or so of work, Ms. Weston complained that she was hot and needed to change into some shorts so she went inside. I waited a minute by myself before I decided to follow her inside to use the washroom. When I got to the bathroom I pushed the door open without hesitation but was surprised to find Ms. Weston inside changing. She was facing away from me at an angle that gave me a perfect view of her chubby round butt as she pulled her shorts up.
“Oooopsy,” she spoke in a surprised, but otherwise jovial, sing-song voice. She wore a faded, old pair of black panties that hugged her butt nicely. Even after her shorts were pulled up and fastened, the image of her big, round ass was still sharp in my memory. In truth, I hadn't seen much before I backed out of the room with an apology, but I was filled with desire at the thrill of having seen something I wasn't supposed to see.
The only women I had seen undressing at that point in my life were all my age with youthful bodies and carefully selected lingerie. There was something sexy about the stretch marks on her thighs and the extra pounds contained by those full-butt panties that intrigued me in a way I couldn't quite explain. She noticed me checking her out and gave me a little smirk on my way out the door, I waited by the back door, trying not to look sheepish as she came out of the bathroom with a chuckle.
“I'm sorry to traumatize you with my fat, old-lady butt. I'm sure the girls at school work a little harder to keep the extra pounds off than I do. Although a simple knock on the door never hurts.” She had a teasing look on her face that pushed away my embarrassment instantly. I recognized an opportune moment to flirt that I was incapable of ignoring.
“Don't sell yourself short. Your ass looks great. You've got no reason to be self-conscious over some skinny twenty-year-old.” I fired a pick-up line at her from the hip without much forethought, but I was a little surprised to find the statement to be true after some quick reflection. I didn't have any experience with older women yet, but I had spent enough time trying to decipher passing glances from women at school that I could tell my compliment was well received.
“Well, aren't you a smooth talker? Let's get back to work before we flirt the day away. ” She had a look of intrigue in her eyes that would have been enough for me to make a move if she had been closer to my age. I agreed and motioned for her to walk out the door first. She knew I was watching her and seemed to add a little extra sway to her hips to exaggerate the motion of her walking.
Our conversation was more personal and flirtatious after this. It was plain to see that she enjoyed my attention from her smiles and laughter, but perhaps the most obvious sign was how often she would bend over in front of me. We continued working in the mid-morning sun and got a lot done by eleven O'clock when we stopped for a break. She invited me into the kitchen for a cold drink that I readily accepted.
“Now that you're a man, I can offer you an adult's drink.” She gave me a curious look before she continued speaking as she bent down to retrieve two beers from her fridge, “A hard worker deserves a beer on a hot day.” She smiled as she caught me looking at her ass again. She handed the can to me and cracked her own as she stood up and led me to the living room, she ignored the couch and invited me to join her on the loveseat.
Ms. Weston was usually in a good mood any time I saw her, but our flirtation had opened her up in a way I hadn't seen yet. She wanted me to make a move, I had suspected it for over an hour at that point but I waited until her intentions were obvious. She placed her hand on my mid-thigh and gripped it tightly as she asked if I wanted another beer when she noticed how quickly I drank the first one. I accepted and she gave my thigh a brief rub, her fingers inched provocatively close to my crotch before she stood up and made her way to the fridge.
I recognized my chance to make a move and gave her a firm smack on the ass as she walked past me. She let out an exaggerated gasp in surprise but the satisfaction was plain to see from the smile on her face when she came back with two more beers.
“I was wondering how long I would have to bend over and wiggle my ass in your face before you made a move.” She handed the beer to me before shuffling past on her way back to her seat. I reached up and grabbed a firm handful of her juicy ass, I released my grip and rubbed her butt to feel its roundness before firmly squeezing it again.
“You have a nice ass.” It wasn't the smoothest thing I would ever say to a woman by a long shot, but she was happy to see the truth of my words plainly on my face as she sat down on the couch and put the beers on the nearby coffee table.
“Your strong hands feel nice.” She spoke absent-mindedly as her hands roamed about my biceps and shoulders. She sat angled towards me in a way that told me she was waiting for me to do something, so I went for it. I leaned in and gently held the side of her face while I kissed her, she moaned softly while my fingers worked their way into the depths of her hair.
Her hand was stationary on my chest as she kissed me back with a passion that I could tell had been pent up for too long. My free hand rubbed along one of her inner thighs from her knee to about an inch shy of her crotch, with every sweep of my hand back and forth I would get a bit closer to her pussy. I could tell she wanted to feel my touch badly but she enjoyed being teased. We paused from kissing when I felt her fingers unzip the fly of my shorts.
There was a lusty determination in her eyes when she pulled my shorts and boxers off. The look intensified when she felt the warmth of my cock in her hand. I was so hard it was throbbing as she slowly stroked up and down.
I reached under her shirt and palmed her breasts over her bra. For most women I had been with, this would have been all I needed to prompt her to get topless. Ms. Weston kept all the power on her side though while she literally had me in the palm of her hand. She increased the pressure and speed of her hand and I forgot all about her shirt as I leaned back into the loveseat with an audible sigh.
“I'm sure a lot of girls from school would be quick to put this in their mouths, and I can't say I blame them, but never underestimate a hand-job from the right hands.” She giggled at her joke as she leaned closer to me and continued. “ Isn't this a little more intimate anyways?” She looked right at me to gauge my pleasure levels, I could feel the breath of her sultry voice on my face as she stoked a little faster on my penis.
“You're so good at that, Ms. Weston” My words came out somewhat sporadically as her adept fingers brought me closer to an orgasm. She laughed at me in a patronizing tone that I didn't mind in the slightest.
“Why don't you call me Kathy.” She could tell I was close to cumming and continued with her relentless work on my dick as she kept up with her patronizing tone, “You're gonna cum for me now, aren't you?” She had a shit-eating grin on her face as she waited for the response that she already knew was coming.
“Oh fuck, Kathy. I'm cumming!” I almost shouted the words out as the best hand job I've ever experienced came to a climax. She didn't skip a beat as my semen landed all over her hand and shirt.
“Good work, champ. You missed my face though.” She seemed to have enjoyed it almost as much as I did. She stood up to get a roll of paper towels and came back to help me clean up.
“Do want to go upstairs, Jack?” She removed her shirt which was now dirty with semen stains while she waited for my response. Even though she already knew it would be yes, she still smiled when she heard the excited tone of my reply. She kissed me one more time and then we left our unopened beers on the table as she led me up the stairs.
“Your mom would kick my ass if she knew about this,” she chuckled a dirty laugh as she opened her bedroom door and continued “This will have to be our little secret.” She turned around to face me when she got to the foot of her bed and gave me a good look at her chest.
Ms. Weston had an amazing pair of breasts, not the biggest I would ever see, but they suited her body perfectly. They were full and round, yet surprisingly firm for a woman her age. She removed her bra and let it fall to the ground. Her nipples were already stiff and I was overwhelmed by an urge to lick them that she picked up on quickly, she placed her hand on the back of my neck and lovingly pulled me into her breasts. I ran my tongue all over her areolas before sucking on each of her nipples.
She sighed and breathed heavily while she enjoyed the sensation of my tongue and lips on her sensitive nipples. I used one hand to hold her breast up to my mouth while the other drifted down to her ass. I pulled my mouth off and kissed her lips again while I worked at the button on her shorts, they were a bit tight so she helped me pull them down over her hips. We both stood in front of each other in nothing but our underwear as our eyes explored each other's bodies. The excitement in the air was palpable now and each second we hesitated felt like a moment, she smiled at me as we pulled our underwear off together.
When we got on the bed we lay next to each other on our backs. She spread her legs and placed one of her warm, thick thighs over top of mine to give my hand easy access to her pussy. She hummed with satisfaction to feel my hard, young dick in her hands again while my fingers gently stroked her labia. She was already moist so my fingertips become slick with her juices while I teased her. Her moaning got louder as I rubbed gentle circles on her clitoris while she slowly jerked me off.
I intended to tease her until she was begging for me to penetrate her, but in truth, I was the one whose patience cracked first. Her legs were already spread wide for me, so I positioned myself on top of her with my legs in between hers.
“I want to fuck you, Ms. Weston,” I said quietly as I slowly entered her, she gasped briefly when the head was first inside. Then she sighed as we looked deep into each other's eyes.
“Kathy.” She corrected with a quick giggle that turned into a moan when I was balls deep, she sounded as if I was scratching an itch that she had been dealing with for far too long. I hoped that my first orgasm would help my stamina but I was getting excited way too quickly so I had to go slow, but she responded well to the pace.
“You have no idea how much I need this.” She dug the fingernails of one hand into my shoulder while the other slipped down in between us to play with her clit as she spoke to me. She moaned louder than any other woman I had been with at that point in my life, there was a confidence in her voice that I loved and it excited me to bring this out of her.
I wanted to keep thrusting into her all afternoon, but my youthful body wouldn't cooperate with this hope. I could feel a pleasant sensation building in my loins faster than I could contain it, I informed Kathy of my impending orgasm with disappointment in my voice. She ran her fingers through my hair and gave me a look of reassurance.
“That's ok, Jack. I want to feel your cum inside me.” The genuine excitement in her voice brought me back into the moment. That wasn't a response I would expect from a university girl, she pulled her fingers out of my hair and raked her nails across my back as I continued my steady pace. The pleasure got stronger with each thrust and I knew I wouldn't last much longer. I gave her long, deep strokes to finish myself off while she moaned enthusiastically. None of the women I had ever been with before had tried to make me feel good for finishing before she did but when I announced my orgasm Kathy called out breathy encouragement with a proud glint in her eye.
I was a healthy, young man and I think Kathy was pleasantly surprised to feel how much semen I ejaculated inside of her so quickly after an orgasm. Part of me wanted to relax, but I was overwhelmed by the urge to make her cum. Knowing I was probably the first lover she had since her husband's passing, I needed to make sure that she had a good time. My oral skills were not as developed at that age as they are now at the time of writing, but I was confident enough to finish her off when she was that close to finishing.
I pulled myself out of her and slipped down her body with a few adeptly timed kisses placed on her lips, left nipple, and belly button on my way down to her pussy. She was a bit surprised at my sudden shift in positioning, and I could tell that she wasn't accustomed to having oral sex performed on her but she quickly relaxed under my moist tongue as I licked up and down her labia.
I didn't want to lose any momentum on her orgasm, so I moved up to her clit. I settled into a gentle but consistent rhythm with my licking that she enjoyed. She dug both hands into my hair as I teased a fingertip inside her and she moaned even louder still when I pushed it into the second knuckle.
She let go of my hair and I could see she was teasing her nipples in my peripheral vision, I loved watching the momentum play out in the ripples of flesh on her breasts as she gave each a brief pinch and shake. After that, she cupped and gently massaged them while the sensations gradually built up to the point of eruption.
I savored the slightly tangy flavor of her pussy as I worked her closer and closer to the orgasm I was intent on giving her. She was almost squirming under my touch and I loved every second of it.
“Oh! That's it, Jackie. I'm so close.” She gripped the bedsheets tightly as she called out in a loud voice. I lapped excitedly at her clit as I listened to the sweet sound of her heavy breathing mixed with the moaning as she got closer, when it sounded urgent, I knew she was close.
“I'm cumming, Oh Jackie, yes” She grabbed two handfuls of my hair as her orgasm took over. She let me continue for a few seconds longer before stopping me, she relaxed deep into the bed as she basked in the pleasure moving through her. Kathy Weston might have been the first person to call me Jackie without making me want to smack them. I've always hated that variation of my name, but it sounded like a song to hear from her mouth.
I lay next to her and stretched my jaw and neck out a bit while I listened to the sound of her breathing slowing down. She let out a deep breath and then rolled over to snuggle with me. The warmth of her breasts on my skin, and the feeling of her heart beating against my chest filled me with a sense of pride that I didn't fully understand. When I think back on that moment, it was one of the first times I truly felt like an adult. She wrapped her arms around me tight as we enjoyed the moment together as temporary lovers.
After a few more minutes of snuggling, she remembered that we had left our second beers on the coffee table so she went to go fetch us two cold ones while still in the nude. I loved watching her butt jiggle with every step as she excitedly left to get us drinks, the sight of her standing there in the doorway with those beers has been a regular memory in my spank bank for years. Her disheveled hair cascading down to her beautiful breasts was already working at my youthful libido as she walked to the bed and crawled in beside me.
“Your parents aren't expecting you home tonight, so drink up. I'm not done with you yet. ” She laughed a sexy laugh as we cracked our beers and touched our cans together in cheers. I savored each sip of that well-earned beer as Kathy and I continued with our dirty flirtation into the early afternoon.
