Category: First Time Stories

A Long, 'Boring' Summer

by writerjab©

Life as a 18 year old male took a dramatic turn in my favor a couple days ago, and now I was hoping for another happy day.

Johnny Bestley and I were best friends from age 5, and living in the only two houses with young kids nearby, our lives were intertwined all throughout the year. Spring time we splashed in mud puddles; summer, swam, fished and explored in the creek; fall, played football, jumped in leaf piles and trick-or-treated; winter, played in the snow.

He also had a sister my age, Kari, who played with a girl who lived across the creek a ways, and in time she became the center of some of my teenage fantasies. Fantasies that only fueled a young boy's imagination as he dealt with the peculiarities of puberty.

Johnny's mom was another story: A raven-haired beauty with brilliant blue eyes and pretty white teeth. Of course, I never realized this until I was around age 14 and discovered the wonders of porn in the magazines my dad owned. The magazines often had stories of older women initiating younger men into the joys of sex. Once again, this became fodder for my budding fantasy life, but fears of screwing my life up or incurring the wrath of my dad kept any actions at bay for another two years. Instead I'd sneak magazines out to look at and jerk off to when he was at work. I'd imagine older women lusting for my dick and shoot a load into my hand.

The summer of my 16th birthday began the move toward events that signaled my entry into adulthood. First, I shot up to my full height which was about 6'1" and though I was still rather slim, the weight began to fill out my chest. Second, sweeping changes in the neighborhood happened as Johnny's folks bought a cottage at a lake outside of town. So much for having a friend to hangout with, most summer days the Bestleys were at the lake. If it wasn't for my job at the local supermarket and my 10-speed bike, they surely would have erected a monument in the cemetery that said, "Here lies a young man who lived a boring life."

Occasionally I was invited out to the cottage and relished those opportunities to see Kari in a bikini. Quite surprising to me, I began to look for glimpses of their mom in a rather attractive one piece suit that highlighted a shapely ass and a pair of tits that reminded me of the chest Victoria Principal sported in her glory years. Hence, the name Mrs. Breastley came into being. I too came discovering the joys of frequently masturbating to thoughts of feeling those tits. I, of course, envied the Bestleys, who seemed to "have it all" as in a beautiful family, a dad who made a ton of family and a cottage on a lake with great fishing.

The shock that followed two years later took sometime to adjust to. One day the family was all together, and the next, Mrs. Breastley moved into town ... alone. I later learned that Trophy Wife wasn't all she aspired to. While she wanted to go to college, her husband insisted he wanted her at home so they could have fun for the rest of their lives. Well, I guess a woman scorned is not a recipe for a good marriage.

Living just with my dad, the neighborhood was indeed quiet. Often I'd see Mrs Breastley driving into town in her colorful Pontiac convertible. I'd either be out mowing the yard working on my tan or at time riding the bike into town. I'd preferred the workout to driving and liked to work up a sweat. We became familiar enough in passing that we began to flirt with each other. I figured she was just figuring out what single life was like again, and teasing me for the fun of it. But, one day she surprised me and said I could call her Karen ... an evil smile then filled her face as she leered at my muscular legs and added,

"Unless you prefer to call me Mrs. Breastley."

I, of course, turned beet red, but she waved it off and said it was flattering to know a young stud could find an interest in an older woman. Mrs. Brea... Karen hardly looked old and I told her that. She was pushing 40 but still had a sleek body with curves in the right places of her 5'7" frame. And, she dressed like a woman who knew she was hot. Either short shorts and form fitting T-shirts or small, colorful sundresses and high heels that had me panting every chance I stole a look her way.

Coming up from the creek one day, I happened upon Karen in the backyard sitting up on a beach towel and rubbing her neck. I cleared my throat so as not to startle her, but I'm guessing she saw me coming up the stairs from "Down Below" as we called it.

"Hi Randy, how ya doin?" she asked.

I said I was good (and was thinking I might be soon great) and inquired about how she was. She groaned in frustration and said studying for her college classes would have to wait until she got the horrible crook out of her neck. She then asked how I was at massaging knots. Taking a look at the deep amber color of her skin, that contrasted nicely with the sky-blue bikini she wore and the long flowing hair falling down her graceful back I suddenly realized I had my own "knot" to contend with.

She invited me over, offered me a glass of wine (she couldn't stand the taste of beer) and handed me a bottle of coconut oil. "This oughta do, if you make a mess you can lick it off ... your fingers!"

I'm afraid the cut-offs I was wearing did little to hide the rising interest I had in what might lay ahead. Despite all these positive signs I was nervous as hell having never even seen first base with a girl before. I managed to drain the wine glass in one long pull which met her approval and a big, sexy smile as she cheered and gave me a refill.

"To hell with the drinking age for one afternoon Randy." She in turn finished the contents of her glass arching her back and thrusting her hot looking tits up and out. "Have I ever told you how much I like your name -- Randy -- I guess you could say I can definitely relate."

She giggled at her brazen attitude and proceeded to refill our glasses as I nearly choked on her last comment. With all this teasing tension, I found the simplest tasks suddenly difficult to focus on. Fortunately, another hefty swig of liquid courage settled my nerves down a bit as I managed to get my hands lubed up without spilling the bottle. I then knelt down and began to rub her shoulders. My position gave me a good angle to spy out the lovely valley of her cleavage. Her neck, shoulders and back felt so silky soft, I soon realized my concentration was gone as I imagined mauling her tits with my open hands, squeezing what I estimated had to be 35C cups, still firm and inviting in a bikini with a deeply plunging front to it.

"Ouch! That's a little too hard there Stud-boy!"

She encouraged me to start again with a little less muscle power and was soon moaning her approval. Though I was glad to bring her some relief, I found myself in a predicament. How do I shifted my burning cock to a better position without getting telltale oil all over my crotch? Karen must have been a mind reader as she took care of that too. She reached back and untied the knot of her bikini as she turned to me.

"I thought you might like to see the breasts you've had your own special name for, for so long," she giggled. "Speaking of long, it looks like you're a bit uncomfortable yourself!"

As she reached out to unbutton my Levis, my hands went for her magnificent breasts. One hand gently squeezed her left breast and marveled at the silver dollar sized areolas with thick nipples that capped each magnificent orb. The other nipple beckoned me as I fastened my mouth onto it. Instinct took over with my ravenous sucking.

In between I squeezed her sexy stiff nipples between my tongue and the roof of my mouth quivering my jaw and biting down enough to give her a thrill. The next five minutes were spent worshiping her tits as I moved back and forth, sometimes with her coaching for what most women liked. She then placed her fingers under my chin and guided me upward. Taking the initiative, Karen introduced me to kissing, and though I wasn't the smoothest, judging from her response it was just what she needed. She moaned and wrapped her arms around my neck and passionately kissed me back jamming her tongue into my mouth. My kissing technique was rather limited, but Karen schooled me on that too.

She laughed lustfully and proclaimed home schooling was in session and that I'd get taught several lessons before the day was done. She told me all about her tongue in my mouth -- French kissing -- and invited me to do the same to her. My tongue interlocked with hers, and it danced along her smooth and even white teeth. She then directed me to nibble along her jawline and neck. I even delved into the channels of her ears, and was rewarded with points for extra credit.

Even as I stayed busy kissing, licking, sucking and stroking her body, Karen managed to remove my cut-offs marveling at what a dirty boy I was to not have any underwear on. Her hands then stroked my stiff cock, she cooed into my ear that I looked big and thick, and that she wanted it now.

Handing me my glass of wine, we toasted each other. "Here's to raw, sweaty sex!"

The look in her eyes and her command to untie her bikini panties was all the encouragement I needed. As her creamy white flesh came into view, I felt the image burn permanently into my gray matter. This hot pussy would remain a fixture in my mind for years to come.

Despite my inexperience, sex seemed to be something I felt ready, and yes, randy to experience. With both of us naked, I lustfully gazed at her clean shaven pussy. Just a wisp of black hair decorated the top of her grotto of delight. I wanted to eat that sloppy looking pussy, it was all dewy from her come spilling forth with her arousal. I also smelled that natural female scent, and if she didn't have other ideas I know I would have been feasting on her succulent flesh.

Instead, Karen stretched out on the towel and then holding my cock, pulled me on top of her.

"Please Randy, shove your fat cock in my cunt, it's been too long since I've been properly fucked!

Fuck me senseless and fill me with your hot come!"

With her hand leading the way she rubbed my cock head along the entrance to her pussy slicking up the big head.

"NOW!"

I bore down inside her and felt as if I'd just entered an alternate universe. She was so hot and slippery, and my cock sank about halfway down into her buttery depths.

"MMMmm! Ohhhh ... wait a sec ... MMM! Your cock feels wonderful, but oh, it's so big! ... wait a sec till I open up ... AHHHH, mmmm, your dick feels like it's splitting me in two!"

I leaned down making contact with her mouth again as we kissed more urgently than our first time. Karen acted like she was trying to inhale me, and we soon were a slobbery mess trading saliva and moans of passion. I then felt something give and Karen's pussy opened allowing the rest of my cock to sink down inside her steamy passage. Oh god, I was in heaven, what a first time to ever have sex. Karen was super hot, I just wanted to pound into her a blow my nut.

We got into a sweet rhythm as I thrust down hard into her. Each thrust she bucked her hips forward taking ever millimeter of my schlong way down inside her. She coached me along the way calling for hard fast thrusts then slower moves where I'd nearly exit her burning quim before driving back in again. She then told me to put her ankles on my shoulders, that I could get deeper into her in this position.

I found I really liked this position as I was leaning against her upturned pussy. While I continued my assault down into her, my tongue bathed her sexy legs and my hands and fingers played with her dainty feet.

"UUUHH, oh your ... cock ... feels wonderful ... mmm, keep fucking me, I .. uh, it feels like it's gonna come out my mouth!"

"Oh Karen, wow, your pussy is so hot, mmm, ... mmmm ... I'm gonna come soon do you want me to pull out?"

"NO! Keep your stiff prick inside me and plaster my insides with your sticky come. Trust me, you just have to feel what it's like to come insider a woman ... OHH! Oh god, this is so fucking hot, fucking you right here in the back yard ... OH, I ... I ... OH ... I'm gonna come!!"

Karen wrapped her legs around my waist and then as her orgasm exploded outward she squeezed her legs drawing me tightly to her.

"C'mon big boy, fill up my snatch!"

The tingling in my balls was too much, I could feel a river of sperm wanting to pour forth ... "Here it comes!"

"YES! GIVE IT TO ME!"

Wow, I can't recall I saw stars, but I did close my eyes and saw light flashing behind my eyelids as my entire cock head felt like one pulsating nerve ending. I plunged one last time in her and the first thick gooey glob blew into her drenched pussy. I was so sensitive I couldn't move as succeeding blasts of come issued forth and spraying into her womb. I considered for a moment I might get her pregnant, but as the after shocks of orgasm continued to send smaller streams of come inside her I just said "fuck it" to myself and enjoyed the moment. I felt like I was swimming in a hot pool of come as some of our combined fluids leaked out and ran down into the crease of her ass.

"AHH! Oh, Randy, you were great, and your cock ... mmm, I love a cock that blows a mighty load and stays stiff in my pussy. That was fucking awesome! I hope you'll give me a chance to enjoy a fuck again like that real soon. Oh, and just so you know, I had my tubes tied a while back, so we can fuck all night and you won't get me pregnant.

We cuddled together, I wasn't in any hurry to leave this party just yet. The throbbing in my cock eased up allowing me to gently thrust into her again. We kissed some more as Karen reached up and wiped the sweat from my forehead. She then asked me to roll us onto my back so she could straddle my cock and go for a ride.

As she got into position the river of our combined come flowed out her snatch and drenched my legs. Karen giggled again and said our combined juices would make a nice snack after she fucked me some more.

Wow, Johnny, if you only knew what a fucking hot mom you had ... actually he hoped no one else knew about Mrs. Breastley, because he planned on taking additional classes when "school was in session."

Yes, it was a long boring summer, now for a completely different reason ...

Written by: writerjab

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Story Tags: older woman, younger man, 18-year-old, milf, his first time, male virgin

Category: First Time Stories