Older and Sexier
by Caesar
Copyright© 1999 by Caesar
Conflicting research paradigms
Have legitimized various crimes.
The worst we can see
Is in psychology,
Measuring reaction times.
While my friends concentrated all their time and energy on the girls of my high school in an attempt to vent even a minute amount of sexual frustration, I aimed my own in another direction.
It all started three years ago, when I was a 14-year-old teenager. Hitting puberty not long before I still had the tall lankiness of that age, my body hard with muscles from sports but otherwise uninspiring. It was that year that I truly came of age; you see, I finally noticed girls.
Bonnie
It was a girl at school that I first noticed and had my first teenage crush upon; she was tiny, cute, and had a big, bright smile. I was obsessed with her after I accidentally saw her full legs and panties when she fell on the ice outside school one morning. No one else saw, and after a quick look and quickly pushing down her pleated skirt, she thought no one else saw either.
Her name was Trish.
I followed her everywhere, hounded and nagged her with my presence, and generally made a fool of myself. Yet, I never said more than two words to her up to that point. But my insistent teenage determination demanded that I act.
So I went over to her home after supper time one evening. I can remember that the snow was falling lightly and the moon was bright. Even with few lights on the houses and the road lights barely making a difference, I thought the night was brightly lit.
Her mom answered my knock. “Hello?” She was drunk. Trish’s mom was also an older model of her daughter, compact, cute, and had a wide, generous mouth that I imagined could smile and brighten any room.
“Oh ... hi.”
“Yes?” I felt like a fool; what was I doing on Trish’s door late at night, her mom standing in a cold doorway as some awkward teenager stuttered his way through normal conversation?
“Is Trish ... I mean...”
She interrupted, “Trish? No, she is at her friends tonight.” She frowned and looked me slowly up and down in a most disagreeable way, as if I was a fancy dress in a shop window that she considered buying. “Would you like to come in? Out of the cold, I mean?”
I didn’t see the reason for it. Trish wasn’t home. The hours of building up my resolve to come here were wasted. If Trish had only been home!
“Is she expected soon?”
Her mom just smiled and stood back from the door, evidently Trish must be expected very soon. Not wanting this little adventure in my short life to end without at least talking to my objective, I thought it would not hurt to wait a couple of minutes.
I stood in the foyer, pulling my jacket and winter boots off. “I’ll make some hot chocolate. Have a seat.” She waved over towards the living room adjacent to the foyer. I watched her half-stumble her way to the kitchen. My teenage hormones forced me to check out the older woman. Nice. Small frame but round bottom that wiggled just the way I like it in those tight jeans she wore. Short but slim legs, well-shaped from what I could see. Her hair was darker than Trish’s, light brown, and shorter by a few inches but still hung halfway down her back.
She finally returned with the chocolate and a beer for herself. “What is your name?” She practically slurred her words.
“Ben.”
“I’m Bonny.” And after a quick drink from her glass, she asked, “Do you have a nice cock, Ben?”
Time stood still. The clock on the wall reverberated about the room. My heart pounded so loudly I thought it louder than the clock, and I froze. No one, I mean no one, had ever spoken to me that way? So blunt, so graphic, and so personal, especially a woman the same age as my mother. What could I say? How could I move ... if I did, Bonnie would see how scared I suddenly was.
She waited a few moments, then asked another question, “Would you like to fuck me, Ben?”
That was it. Like some idiot, I started to cough and hack. The blood went to my face, and I felt like my cheeks were on fire.
Still keeping me unbalanced, Bonnie set down her drink and stood. “Trish is staying at her friends’ overnight. If you want to fuck me, I’ll be upstairs in my room.” She slowly walked away, nearly tripping over her own feet.
As soon as Bonnie was gone, I nearly ran to the door and started to fumble with my boots. God, how did I get into this situation?
Then it hit me, with one boot on and bouncing about trying to get the second one on: Bonnie wants to have sex with me. Me!
Holy shit!
I slipped my boot off and stood there at the base of the stairs, feeling nervous and extremely out of my realm of expertise. Approximately at that time was when the hormones finally kicked in. I even thought how it was unfair to have sex with a woman that was drunk. Would she still have asked me if the alcohol was not in her system? Yet the hormones overrode common sense and intelligent reasoning. Who cares! Bonnie, Trish’s mom, wanted to fuck me!
Wow.
I ran up the stairs and found myself standing in the open doorway to Bonnie’s room. It was the first time in my life that I’d ever seen a naked woman.
Bonnie lay on her bed, right in the middle, fully unclothed. She was rubbing her hand between her legs over and in a generous mound of pubic hair. Her breasts, hung nearly to either side of her chest, had dark, inch-wide nipples that beckoned my gaze. Her legs were wide apart, with knees slightly bent. It was a lewd and bawdy position. It was also more than I’ve ever seen.
My teenage cock thrust painfully against my pants. It knew why it was here.
“Come here and fuck me, Ben.” Her fingers spread the generous pussy, and I saw the glistening pink beneath.
My hands scrambled at pulling my clothes off. When I bounced comically about, anxious to lose my virginity, Bonnie continued to taunt me with her words. “Get that hard teenage cock in this pussy ... fuck me hard ... use me like a whore...” I climbed up on the bed, between her legs, and aimed my cock towards the junction between her thighs as if it was my love missile. “ ... my husband likes whores...” I fumbled about, poking her hand, pussy, and thighs - unable to deliver my missile. “ ... but he doesn’t like to get them at home...”
Bonnie grabbed my shaft with her free hand and held me firm. It was the first touch of a woman’s hand upon my cock, and it felt great. Then she slowly pulled me towards her. Without a preamble, I suddenly felt myself sink into the most desirable feeling in the world, the hot, wet channel of a woman.
Both her hands came out from between us and grabbed my skinny, hard teenage ass and pulled me roughly in, towards her. I was seated fully within her love grotto.
It was too much. I felt my cock begin to twitch and spasm as the seed of my loins flooded into the first vagina I’ve ever been in. Bonnie whined, “Come on, my face, on my tits...”, and quickly I pulled from her, allowing my seed to continue to spurt from my body upon her breasts. I aimed for her nipples, as sexy as they looked. “ ... use me like a whore!”
I was.
Bonnie grasped both her breasts and wrapped those delightful, warm, soft flesh globes about my cock. Nearly as delicious a feeling as her sex had been. She tilted her head and opened her mouth. A tongue began to tease the head of my cock even as the spasms were nearly gone.
I knelt panting above her, looking down at the most incredible sight. Bonnie only stared at my cock.
Thankfully, especially this being my first time, my cock never softened. Oh, the pain-filled hardness was gone, but it still throbbed with desire.
Bonnie looked up into my eyes with a lust-filled smile when she realized the same.
“My husband never fucked my tits before, never had me lick the head of his cock either.” Awkwardly, I moved off her, as she motioned me to give her room to move. “If he ever asks you...”, she turned over and showed me that sexy round ass and got up on her knees, “ ... you will have to tell him how you fucked me. Perhaps then he’ll not need to go out to get his whore’s.” Bonnie motioned me behind her.
The unexperienced idiot that I was, I had no idea what she was trying to get me to do. Thankfully, she simply grasped my hard cock and pulled it until I again felt it enter her body. “Now fuck me, Ben. Hard!”
I did.
It would soon become my favourite position, behind a kneeling passionate woman. I grabbed her hips and watched with delight as she slammed her body back against me again and again. My cock felt as if it was halfway to her chest. Bonnie began to make noises that I’ve never heard before, noises that I wanted to hear again and again. It was of a woman in the heat of passion.
Soon, I again felt the familiar tingle in my balls and attempted to hold it back, unsuccessfully. Bonnie must have felt me tense up also. She squealed in delight and ordered, “Oh yes, come on, my ass, Ben. Come all over my ass hole.”
Strange request, but I complied.
Soon, I lay next to Bonnie on her marriage bed. She lay panting, her back to me. I couldn’t take my eyes off her. She was beautiful, sexy, and the most delightful sight I’ve ever seen.
A mumble from her side of the bed, “Rub my ass, Ben?” No longer was it a command from her, but a request. One that I had no problems complying with.
“Hum ... rub that wonderful spunk all over my ass.”
Certainly. My hand was bold. Why not, I thought after what we had just done? I slipped it between the cheeks of her round, firm ass and slipped my sperm-coated fingers around the tiny, round, hard muscle of her anus. I had seen it winking at me as I pounded her from behind and thought how sexy it looked but had not had the nerve to touch it. With her request, I now did.
She moaned lightly and squirmed about while also arching her back and pushing out her ass, which effectively allowed her ass crack to widen. I took this as permission to enjoy myself even more and slipped my finger into her backside.
That was when the fun ended. She giggled. I have never heard an older woman giggle like this before and spun about, which disengaged my hand. “That’s enough, stud.” Me? “I’m going to have a long, hot bath. Maybe next time, this whore may even let you fuck her there!” In her ass hole? Wow.
Bonnie rolled out of bed and quickly disappeared into an adjoining bathroom. I slowly stood up, feeling as if I was on top of the world. Me, I had just fucked a woman. Not a teenage giggly, inexperienced girl, but a real, live, sexy woman! I had given my virginity to this woman, or rather, she took it from me.
As I finished putting my sweater on, I remembered two things. That Bonnie no longer staggered when she walked to the bathroom or was slurring her words since I joined her in her bedroom - was she even drunk? Why would she feel the need to fake intoxication? It made no sense to me. The other was her words as she departed, “ ... next time...”!
I couldn’t stop from smiling all the long walk home.
My father wouldn’t have noticed if we had a roof or not on our house, but Mom did. She asked me several times what I was smiling so much about. She asked for several days after my adventure with Bonnie.
Something happened to me after I left Bonnie. Something inside me changed from a young teenager, a boy really, to a young man. I knew what all my peers had been anxious to discover with girls their own age, what they wanted to ultimately do with them but didn’t know how. I did. Bonnie had taught me without being a teacher.
Trish approached me at school. Though I thought she never even knew I was alive, “Hi, Ben?” See, she wasn’t even sure of my name. “Mom said you came around last Thursday. Did you want something?”
Now a week earlier, I would have stammered and stumbled at the approach with this sexy little teenager, but no longer. I no longer felt interest in her, only her mother. “Yes, but I found more than I came for.” I left her standing in the hallway with a puzzled frown upon her face.
Darlene
I have been shovelling Mrs. Harrison’s walks for several years. With the abundant snow these last couple of winters, I’ve made enough to purchase a new bike last summer. Unfortunately, they had a very long walk and driveway. Fortunately, my pay reflected this when she came time to pay me.
Mrs. Harrison had been living next to us for as long as my parents had been here. She and her husband were professional people, she being a lawyer, I believe, and had no children.
Big deal, you may ask?
Just as I started to shovel, Mrs. Harrison drives up, waves, and forces her truck past me into her garage. Thinking nothing of it, and this not being the first time, nor the last, that I was shovelling their walk in winter. Half done, I stood up to stretch and to catch my breath and saw Mrs. Harrison standing in her huge living room window with a steaming mug of tea in both hands, looking right at me with a strange half-smile and faraway look. I simply waved spiritedly; she just smiled and turned about into the shade beyond my vision.
I returned to shovelling.
No big deal, right?
True. At least if I had not had a taste of older women in the form of Bonnie. Don’t get the idea that my one sexual experience left me an expert in the subject; far from it. Only that it left me with a new perspective towards the ladies that I never truly noticed before.
Within her garage, hours later, I was cleaning off the shovel and pick before returning them to their rightful spot when Mrs. Harrison opened the inner door to her garage and smiled gently at me. “Good work again, Ben.”
“Thanks, Mrs. Harrison.”
“Can I pay you next week?”
Of course, she can. She always paid me at the end of each month for the sum total of my work. “Sure.” I was finished with my tools and stood facing her, in all my winter-bundled glory.
Mrs. Harrison smiled again, then turned as if she was leaving. “Do you have any hot chocolate, Darlene?”
It just sort of blurted out of my mouth. I certainly had not planned to ask or especially to use her first name.
She stopped, looked over her shoulder with an uncertain and surprised look, and nodded. “Certainly. Come on in, Ben.”
I had never used her first name before and had only known it from overhearing conversations between my mother and Mrs. Harrison, Darlene. As I pulled off all my winter gear, it was cold that day, I remember. She returned to the kitchen, and I could hear her prepare my warm drink.
In wool socks, I eventually joined her, my sweater hanging comically halfway to my knees. I must have looked like a red-cheeked bundled string bean. As she stirred in the milk for the cocoa, which I rarely have and is always a treat rather than simply instant hot chocolate, I enjoyed the sight of her.
From the rear, Mrs. Harrison looked rather good in her black jeans, white socks, and fuzzy sweater. Her auburn hair bounced whenever she moved, and her pale skin nearly as white as my own, blame it on the winter.
Darlene must have noticed my appraisal and looked sideways over her shoulder with an unknown sparkle in her eyes. I know not what I had gotten myself into but felt a heat gathering between my legs and resisted an urge to give my cock a squeeze.
She delivered the cocoa into my cold hands, and our fingers lingered for just a brief instant. “My goodness, you are cold, aren’t you?”
I just smiled and took a sip of the hot drink; it was very good.
“Is your mother home, dear?”
“Yup, but she is going grocery shopping later today.”
She nodded. “I must call and ask her to get some frozen blueberries for me.”
Small talk sucks.
I looked down right at the bump in her sweater, gaging her breasts to be small. “Do you find me attractive, Ben?”
With a flash, I returned my eyes up to her own and found her face smiling with amusement. “I find you very attractive, Darlene.” I couldn’t believe how calm my voice sounded, as if I had played this verbal game with many other ladies. In fact, I felt my free hand trembling and grasped my mug of cocoa with both hands to stifle its movement.
“You are a rare one, dear. I’m older than your mother.” She sipped at her tea mug, but her eyes never left mine.
What could I say? I just shrugged and again found my eyes drifting down to the bump in her sweater. In my absence, both small mounds now had a prominent thrust of what could only be nipples. Darlene now had hard, thrusting nipples that could even be seen beneath her expensive, fuzzy sweater.
I tried to return my gaze back to her face but could not, and found my eyes drifting down to her small waist and to the junction of her pant legs. I wondered what she looked like naked.
My teenage hormones began to work overtime.
Again, I stared boldly at her nipples. A voice startled me, “Are you a breast man, Ben?”
Shit, she caught me. Finally, I returned my gaze to hers. “No.” She was about to ask a question, but I continued, “though I would make an exception with yours, Darlene.”
That caught her attention, as well as my own, if the truth be told. Her eyebrows shot up, and she looked down into the contents of her tea mug in silence. How bold can I be? Certainly not as bold as Bonnie had been ... could I?
No. Just asking such a bold question scared the hell out of me. Hell, my own mother may hear of it!
I certainly did not want the conversation to end at this point and said, “Normally, I am an ass and leg person. And yours are great, Mrs. Harrison!” I meant it. They were great in a petite, slender sort of way.
Finally, she looked back up into my eyes. “Darlene, I like it when you call me by my name, Ben.” She turned about, opened the dishwasher, bent over slowly, and put in her now-empty tea mug. I watched every movement. Finally, she turned back to me. “No one has ever said those things to me before, dear.” Darlene actually looked sad.
Truth was, I was a bit surprised. Of course, she was no beautiful woman, but especially, for her age, she looked great. “Even Mr. Harrison?”
She snapped. “Especially my husband.” She quickly softened her look. “Are you finished, dear?” She meant my cocoa.
I was, and she also added this to the dishwasher, giving me a great show of her bent-over ass. In fact, she fumbled around, moving a few dirty dishes and cups about, all the while staying bent over for my pleasure, I was sure.
Finally, she stood back up and faced me awkwardly. I had nothing to say. Of course, I lusted after her but knew not what else or how else to approach her. To me, I ran the marathon and couldn’t get to the finish line. I had to quit. I turned and headed back to the garage door. “Well, I better get home. I’ll tell Mom that you wanted some blueberries.”
“Wait!” Her voice was rather frantic, and I turned to find her roughly rubbing her palms along the flanks of her black, faded jeans. “Do you have to go so soon?”
Again, I enjoyed the sight of her thrusting nipples. What else could I do? I hadn’t the experience to take this little adventure of ours any further? I simply shrugged and answered rather stupidly, “No, I guess not.”
“Would you like a quick lunch perhaps?” She now looked nervous, possibly even more so than I. Could I do this to her? What a flow of power and adrenaline flowed through my teenage veins.
“No, thank you.”
Nervously, Darlene looked about as if wondering what else she could offer me. Couldn’t she tell what I wanted? Her nervousness was calming to me.
I walked up to her slowly. “Would you like...”, she started to ask but stopped when my hands came up to her chest.
With a move that surprised me for years to come, I opened my hands palm-up towards her and placed them upon her small mounds, pressing inwards until her nipples poked into my palms firmly. Her reaction surprised me; Darlene closed her eyes, sighed deeply, and with a ragged breath, she pushed her torso harder into my hands.
Wow.
Towering about a foot above her five-foot frame, I felt strong, big, powerful, and in control. I suddenly wanted this woman with a passion that I never felt for anyone ever before, not even Bonnie. I brought my lips down to hers.
Those lips were slightly open, enough to breathe through, and partially dry. When my moist, hot lips touched hers, Mrs. Harrison came alive, and her demeanour changed instantaneously. In a way, she attacked me.
Darlene opened her mouth wide and stuck out her tongue, forcing it between my teeth. Her hands came around and grasped my hard, lean buttocks. As she forced her mouth upon me, not that I was disagreeable though, she groaned with a guttural sound into my open mouth.
That woman taught me more about kissing in the ten minutes we stood there than most of my friends would ever learn. After attacking my mouth with her own, though her hands were also busy behind me, she softened her attack. Those hard, fast kisses quickly turned to soft, moist, very sensual kisses that allowed her to grind her body into my hands and thighs. Darlene alternated with soft, slow kisses to hard, frantic, rushed plunges of her tongue and lips. I loved it.
We had been standing so long, kissing and fondling, though my hands never came off her breasts, that my jaw was actually tired. I slowly pulled away, opened my eyes, and stood looking down into her eyes.
With amusement, she asked, “Now do you want to leave?” My answer was a big grin, and both of her nipples found their way between my thumbs and index finger in a playful but firm pinch. “Oh god! I may come just from your hands on my tits and your kisses.”
She stood swaying slightly, as if there was a slight breeze, enjoying my hands upon her breasts. I twisted one nipple as my palm fondled her other round breast. “What is it you want me to do for you, Ben?”
Do? I wanted to fuck her. What else could she have meant?
Do you remember those moments in life that you felt as if you were in a place that you just didn’t fit in? This was one of those for me. I suddenly felt as if Mrs. Harrison was being fondled by another person, a person that knew exactly what they wanted to do with her. I didn’t; I was surprised to discover.
I think she realized my sudden fear, yes, fear, and took my busy hands in her own, leading me to her living room. With her eyes never coming off my own, she led me, walking backwards, I may add, to the middle of the room and pushed me gently backwards till I found myself seated facing her.
Darlene took a step back and started to unbutton her sweater. It wasn’t some erotic striptease but a slow, deliberate undressing by a woman that hadn’t been naked with a man, other than her husband, for many years. Her hands actually trembled as the buttons opened.
She didn’t hesitate but instead watched my eyes, my hungry eyes, as she allowed the sweater to drop to the floor before her. Still watching, she reached behind to undo the brassiere.
Those conical white breasts suddenly revealed themselves to me. Her nipples were dime-sized but thrusting far out like a small finger. I wanted to see her pull upon those sexy nipples and wanted to ask but found my mouth too dry to talk.
No matter, with a slightly red face, Darlene began to undress the remainder of her garments. The white socks quickly disappeared, the jeans took a while longer but soon those joined the other clothing. The panty, white cotton but high in the hip and well cut in the crotch, looked superb on her. Those also joined the small pile at her feet.
Finally, she stood completely naked and nervous before me. Her pussy, the same wonderful auburn as her head, was surprisingly sparse, with only a tuft above the dark pink cleft below it.
“Do you still want to go?” She tried to smile as if it was a joke, but I knew better. I would never have guessed it before today, but Mrs. Harrison must not think highly of herself.
I just nodded an answer and was awarded with what looked like a thankful look on her part.
Darlene didn’t saunter or slink over towards me, as I had read some women like to do. Instead, she took the short steps necessary to stand between my spread knees.
No words were exchanged, though I would not be able to anyways, but our eyes stayed fast upon the other.
Darlene bent at the waist and began to fumble with my pants, her trembling hands making it more difficult. I didn’t need to watch to know that my cock suddenly found a way out of its prison, as the cool air kissed its sensitive surface. Darlene, though, stole a look down between my legs and gasped in what I could only take as pleasure.
She didn’t waste any time, nor did I help or hinder as she quickly came closer and crawled up upon my waist, her knees to either side. Her warm hand fumbled with my shaft, and her torso moved about anxiously. All the while, I just watched her face, marvelling at her beauty and that she too was nervous and excited just as I was.
Then it happened. I felt her warm, clenching wetness engulf my thrusting manhood. Darlene finally closed her eyes, wrapped her arms about my neck, and threw her head back to groan loudly.
Finally, I looked away from her face and moved my gaze downwards to her breasts and to her navel. I reached around and grasped her tiny, soft buttocks in my hands. Darlene groaned out and threw her face into my neck, her lips whispering, “Tell me what you want me to do, Ben?”
Crazy question, but this time I was more prepared to answer. I lifted her torso by her buttocks with my strong hands and whispered into her ear, “I want you to fuck me, Darlene!”
“Oh yes!” She began to move, ever so slowly, up and down on my hard shaft. I dare say, she was noticeably tighter than Bonnie had been, while still feeling the abundant juices flowing down to drench the front of my pants.
Movement caught my eye to my right and slightly over Darlene’s shoulder. It was a mirror. I saw the most lewd and sexy sight of my life. A mature and very sexy woman whose body was perfect for my desires moving seductively and deliciously above my clothed tall teenage body. I couldn’t help but watch the show Darlene inevitably put on for me as she twisted her head and back all the while her buttocks responded to my fondling.
I pulled apart her buttocks to reveal the hairless crack and tiny brown winking hole between. Yes, ‘winking’, it opened slightly and closed as Darlene moved with the length of my cock.
Remembering what Bonnie had said, I had wondered at the feeling of my cock within a woman’s ass hole, wondered how it felt for a woman.
One hand moved inwards and I pressed my centre finger against the hard round muscle. Darlene gasped when I touched her there and groaned out, “Oh god! Touch me Ben, use me please!”
Certainly.
I shoved, a little too roughly, but it was my first time. My digit into her rectum to the third knuckle. Darlene hissed and grimaced in pain, but it quickly subsided and turned to more moans of pleasure when I began to frig her ass in time with the cock in her cunt.
When my mouth enclosed a tiny thrusting nipple and drew it strongly into the back of my mouth, Darlene suddenly clenched every muscle in her body and squealed out so loud it actually hurt my ears. I simply froze my body and watched her face as it danced with erotic music of a woman during the explosion of her orgasm. Her spine began to bend backwards and her head rolled about on her neck as she called my name out again and again. Her body suddenly broke out in a sudden cold sweat and her skin got little goose bumps that only highlighted this special moment.
Finally, she lay above me, spent.
My hormones were still raging, and I moved my hands as if to steady her. I was going to roll her over with disengaging our erotic link. Instead, a tired-sounding Darlene placed her hands upon mine and moved her lips to my own. She kissed me soundly but quickly, “Let me, darling, I want to...!”
Again, that petite, sexy body began to move, my cock engulfed in the hottest, most addictive furnace that I had ever imagined.
Her arms wrapped about me in a strong embrace, her lips whispered in my ear, “I need to make you feel as good as you have made me feel!” Her tiny, hard thrusting nipples poked through my clothing enough to notice. “I want you to fill me with you.”
Those words, the tight, hot, wet sex, and her sweaty, soft, petite body were enough to grant Darlene her wish. My seed began to flood her depths. She also had another orgasm, smaller though. Our bodies clenched and vibrated with a symphony of pleasure.
I sat panting beneath her sweaty body, feeling like the luckiest guy alive. My penis shrunk within her until I felt it begin to slither out of her slimy, warm hole. Darlene groaned when it finally slipped out of her.
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