Jake: Finding True Love
by Dapper Dan
Copyright© 2008 by Dapper Dan
Erotica Sex Story: Jake spends too much time looking in the wrong places for the true love he's seeking.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa mt/ft Consensual Heterosexual Interracial First Oral Sex Anal Sex Masturbation Voyeurism .
FORMATIVE YEARS
"Jake! Jake, are you in there?"
Oh, hell, that's Jane! "Yeah, just a minute." Damn! No privacy even in my own room. Damn good thing that door's locked. Jane was the thirteen year old girl from next door. I had just been looking through a copy of Sunshine & Health, a nudist magazine with my pubescent, fifteen year old dick at full mast and dripping precum. Shit, not now. I quickly jammed my cock back into my pants and zipped up. Just as quickly, I shoved the nudie magazine under my mattress.
"I'm coming, Janie, I'm coming." I wish to God I was, my balls are aching now.
That was summer, 1950. Back in 1939, the year before my birth, my folks built the house in which we lived for the next umpteen dozen years. I had two younger sisters but no brothers. Jane's family moved into the house next door three years later. I'd been baby sitter for Jane and her two younger sisters since my eighth birthday.
Jane and I grew up close and became "bosom buddies" ever since her tenth birthday party when the two year difference in our ages no longer seemed so great. She and I were more like two male buddies, bonding over the years into a pair of roughnecks in the summer woods and baseball lots. We went through grade school, junior high, and senior high school together and remained close, in both a brother/sister sort of way and as really close friends and confidants, but nothing intimate.
As for more intimate relationships, I did date girls in high school, quite often, as a matter of fact. As to sex though, I was shy and morbidly fearful of rejection so rarely tried, let alone made it, to what was back then was so quaintly called, second base. That certainly precluded going all the way around the bases to score a home run.
In fact, I distinctly recall a date during which we saw the movie Tammy. There was a line in the movie that saw "Tammy," played by Debbie Reynolds, smile up at the young bachelor, I forget the actor's name, and say, "I'm a she-wolf on the make." My date and I had doubled that night, and we had the back seat. I leaned into my date's ear to whisper something and she thought I was going to do something else with my mouth.
When I pulled back after only the whispered words, she looked at me and with a leering, come hither look, said, "I'm a she-wolf on the make." I just sat there in petrified silence. So, I had to be satisfied with Sunshine & Health and other girlie magazines and my right hand. A lot of Playboys changed hands in the boy's bathrooms at the junior and senior high schools for a similar purpose.
There was one other source I used for my teenaged sexual outlet. As I remember, the first time was just after sunset on a warm, humid, summer evening between my ninth and tenth grade years. The house Jane's family lived in had a full basement, but it was shallow. This meant the house stood tall above ground level and, more to the point, the bottom of the basement widows were at ground level. The basement windows also did not have shades or curtains. I was sitting idly on our back porch step that evening when movement inside the dimly lit basement across the way caught my eye.
There I spotted Jane's eighteen year old sister Cora, a senior at out local high school, moving around. My head snapped up with my eyes focusing intently into the window and my cock twitched mightily when I saw that all she had on was her panties and bra.
I stared even more intently as I watched her reach behind and unfasten her bra and I produced an instant, raging hardon as she slowly let the bra fall forward and off, exposing such a delicious pair of large tits that I nearly came in my pants, then and there. Cora stepped out of view for a moment, God, I sure hoped she'd reappear.
The thought'd barely cleared my mind when Cora did in fact step back into view. She paused, her back to me, and slowly peeled out of her panties. Damn, that bare ass had my cock really throbbing. Cora held her panties and slowly turned full face to me, exposing that beautiful black triangle of hair at the apex of her legs. Then I did cum in my pants, in buckets as is the proverbial but erroneous saying. Meanwhile, Cora had once again disappeared from view.
The noise of a car driving my direction caused me to lurch to my feet and, in somewhat of a daze, walk toward our garage and out of sight. As the car turned into Jane and Cora's family drive [which was separated from our drive by only two inches of grass], I peeled out my dick and rapidly stroked myself to another climax just thinking about what I had just witnessed. Ah, blessed youth.
As I peeked around the corner, I saw a senior class boy exit the car and walk around to the back door of Cora's house. By the time I got back to our porch, my cock safely tucked away, and looked through that window again, George, was embracing the naked Cora in a tight clinch with both of his hands tightly clasped to Cora's tight little ass cheeks. My half deflated cock instantly rose to full attention again. My sticky underwear and jeans confined my dick to the point of real pain by that time.
I'd heard rumors around school about Cora having round heels and such, but I was too shy and embarrassed to ask Jane or anyone else about the rumors. Jane and I could talk about most anything, but not her sister. Anyway, as Cora and George walked into another room out of view, I decided to investigate further. With some malice aforethought, I ran to my room and grabbed my Polaroid camera and then walked to Cora's back door.
I did know the rest of Cora's family, including Jane, were gone for the evening, so the coast was clear from that angle. I was barefooted for stealth, as I eased the back screen door open and slipped inside. Damn, where I got the courage, I still don't know. I paused a moment to ponder the sanity of the audacious action I contemplated. Shit! Nothing ventured, nothing gained. I started down the basement stairs.
The descent of the basement stairs was agonizing as I stepped slowly on the outside edge only to gain the bottom without making a sound. I'd been in this basement numerous times with Jane [platonic visits only] so I knew where George and Cora were most likely to be located.
As I peeked cautiously around the door, my guess was confirmed. There, on a day bed, were George and Cora deeply involved with each other. They were both completely naked, George sitting on the bed, legs spread wide. Cora was on her knees in front of George, deep throating him. I couldn't help it, the sight was too much for me and I came in my pants again, instantly. They were much too busy and engrossed in each other to notice me.
I continued to watch as Cora suddenly backed off, climbed on the bed, and lay on her back with her legs spread wide. God, her pussy was unbearably gorgeous. She cooed to George, "Fuck me now and fuck me hard, Georgie." George didn't say a word, he just moved up, climbed in the saddle, and plunged the biggest cock I ever saw straight into Cora's pussy in one swift, hard stroke.
That elicited a loud, "UNGGHHH!" from Cora. George pounded in and out of Cory's pussy while his hands played with her tits. My cock pulsed, but no cum erupted. I almost forgot why I was there. I quickly raised the camera. The flash got their attention! I got off a second shot. This one caught their surprised expressions as they stared at the camera. I don't know how I stood there so calmly, but I got still a third shot off as George was half pulled out of Cora's pussy, catching his huge cock half in and half out.
It was at that point that I cut and ran as fast as I could up the stairs, knowing if I made it out the door, George was unlikely to follow me outside nude as he was. I made it out and back to my house. I slammed and locked the door behind me and dashed for my room.
I looked at my developing pictures, locked in my room upstairs. The faces of both showed quite clearly in all three pictures! Then the phone rang. My folks and sister were gone for the evening also, to the same function as Jane and her parents. I picked up the extension in my room and heard, "Jake, please."
"S-s-speaking," I recognized the voice on the other end.
"Ahhhh, Jake!" Cora exclaimed. "You are a very naughty little boy, aren't you."
"Depends on what you call 'naughty',"
"You know what I mean, Jake, you and your naughty picture taking."
"I wasn't the naughty one, doing the nasty deed," I reminded her, "I was just photographing 'nature'." I was also wondering how I suddenly came up with the courage to stand up to Cora.
"Be that as it may," Cora responded, "just whata ya got in mind now, Jake?"
"Well, I could ask you and George for a chunk of money. I could also simply leave copies of the pictures I took in likely places all over school and town, but I can think of something even better."
"Like what?"
"Like a front row, free seat for the next couple of shows would be much better!"
After a momentary pause, Cora answered, "I'll have to talk to George first," and hung up.
So, that's how I got an exclusive ticket to the next show. Cora had me come over before George got there so that I got to see them undress each other. George was not a bit happy with me and I didn't like the look he gave me as they plopped into bed. Moments later, as George was pumping in and out of her in a missionary fuck, Cora turned her head to look straight at me and asked, "Do you like what you see, Jack?"
"Y=yeah, I, uh, I do," I groaned with a croak in my voice.
"Would you like to join us, Jake? I could use a cock in my mouth right now."
"N-N-NO," I stuttered in surprise, "I, uh, w-w-will just w-watch, t-thank you."
"Suit yourself, but I can plainly see you are enjoying yourself."
She sure was right as hll about that. Fully clothed, my boner was so huge it simply could not be hidden. Not touching myself anywhere, I came spontaneously in my pants yet again. The wet spot clearly soaking through both my underwear and my jeans. And, the wet spot was steadily growing larger and larger without a hint of the boner going away.
"See how it's done, kid?" grunted George with a growl. "Nothing like it in the world, kid. Just blow your dick up and pump it in and out. Nothin' beats dippin' your wick in a sweet pussy."
"Oh shit, I'm gonna to cum!" yelled Cora.
And cum she did. really hard. George was right behind her as he arched his back and slammed his cock as deep as he could go, spewing a shit load of cum deep into Cora's hot box. I came again too, still without ever touching myself! Fucking amazing.
I watched as George uncoupled and Cora sucked his cock clean and then I hastily excused myself. I couldn't take anymore without getting involved. Without taking my eyes off the naked Cora, I backed out of the room to a wicked wink and smile from her and fled up the stairs.
There was only one other show, but I wasn't invited. I think George was too nervous with me on the scene. George and Cora only got together those two times before they left for separate colleges a month later. Though I never got that lucky again, I continued my Peeping Tom career for many more years at any opportunity that presented itself as an adjunct to my sexless dating and masturbation in private. Jane never knew about this side of me. I would have died on the spot if she had found out.
To this day, I still enjoy visiting a nude beach for the view, and I certainly don't mean the ocean view, though that's nice too.
When I graduated, in 1958, still a virgin, Jane had two more years of high school and I went off out of state to college at the end of that post grad summer. The night before I was to leave, Jane and I spent a lot of time together, alone. After a movie, we sat, cuddled close with my arm around her in my car on Lookout Point. She cried a lot and I almost did.
Jane asked, "What am I going to do without you? You've always been there, with me and for me--from giving me a shoulder to cry on, to wiping my tears away, helping me with my Algebra, to counseling me about my boyfriends. God, Jake, what am I going to do?" And she burst into fresh sobs.
"You'll do ok, Janie, you will find a good guy to take my place and forget all about me."
"NEVER!" Jane screamed. "NO ONE will EVER take your place and I will NEVER, EVER FORGET YOU! Don't even SUGGEST such a terrible thing."
"Well, I'll never forget you, Janie, and I'll write to you regular like. You can write me with any questions or problems."
We kissed then, tenderly, even passionately.
Things started to heat up and I had to break the spell. "Janie, we can't spoil the perfect relationship we have had for sixteen years with where this is trying to go. I'd better get you home." I did then manage to get her home, but not before she had soaked my hanky and nearly exhausted the box of Kleenex I keep in my car.
When I pulled into my family's drive, she piled out of the car before I could get around to open the door for her and she fled across the way to the back door of her house, still in tears. "Shit!" was my only comment, whispered to myself as I climbed the porch steps to our back door.
The next morning at ten, I stepped off the train platform and climbed the steps into the train coach that would take me to the University of Michigan, some 1,200 miles away. Jane didn't come to see me off. Jane's parents apologized but said Jane was so grief stricken, they couln't get her out of the house.
That was twelve years ago. Now, I'm on my way home for the first time in those twelve years and wondering what I'll find. Why the passage of twelve years before I saw home again? Because my parents died in an auto accident my first year at Michigan, and my siblings went to live with Mom's sister on the left coast.
So, I spent my college summers on archaeology field trips and a quick visit or two to my aunt's to see my sisters. After college graduation, I spent several more years at the Missouri School of Mines with intermittent and quick visits to my Aunt's house on Christmas, and then more years overseas, as a company geologist for a big oil giant, looking for oil.
Jane or Janie? Yeah, we corresponded for two years fairly often, quite often, in fact, for the first year. But that correspondence dwindled quickly after Jane went to college. My side of it, anyway. After a while, her unanswered letters quit arriving. But, before I tell you about my homecoming, I need to fill in some of the details of those years between high school graduation and my pending homecoming.
UNIVERSITY YEARS
I spent my freshman year at the university in a state of near perpetual fear. I just thought I had to work at studying to get through high school! At the university, everything was big: the campus, the student body, the buildings, and most of all, the class assignments.
Girls, oh yeah, girls. Well, they existed in big numbers too on campus, some really great looking babes, but I was so engrossed in keeping my head above water grade-wise, that I barely noticed them. I was so scared and studied so hard that I made the Dean's List of the top 20% of the student body the first semester and never dropped from the list in four years. But, at the cost of very little social life. Instead, I had my girlie mags and typewritten copies of sex stories that circulated throughout the dorm in those days before computers and the internet, and my right hand. That was my "social life." That was my freshman year.
My sophomore year? Ahhh, yes, my sophomore year. I joined a fraternity and my social life improved to the point I began dating some, ordinary girls, ordinary dates, and definitely no sex. Then, I celebrated my 19th birthday in January and met HER in February, on the 28th. I lost my virginity on February 29th [yes, it was a leap year].
HER (she) was Jennifer. Jennifer could have been the other girl next door--the one on the other side of our house. Jennifer possessed a flaming and natural red head of hair with green eyes and a quite cute, turned up nose. Her face contained a sprinkling of freckles. My red headed flame stood a petite five foot three with a tight, trim, well proportined figure that was to die for.
She had a tight little ass and two gorgeous legs descending down like they were never going to stop. Said ass would also sway and twitch deliciously as she walked. Her tits were in perfect proportion to the rest of her body, not too big, not too small. At least that was waht I thought from what I could tell through clothes.
I met Jen one day on my way to class--she was descending the steps of the science building as I was starting up. We both had our heads down, avoiding the blowing, stinging snow, deep in thought and not watching where we were going. We crashed into each other and both fell to the steps, scattering our books and papers in the wind and snow flurries. Neither one of us got hurt, physically.
"God damn, why don't you watch where you are going?" shouted this angry red head as her temper began to rise. "You, You Y..."
"I could say the same to you," I said, cutting off her sentence.
"Nothing gallant about you, is there, you big overgrown ass!"
"Not in this day of women's lib." I quipped.
This was quite out of character for the old me, but a year at the big U had changed me some. I could see that Jen was really angry, but neither of us said anymore as we frantically tried to retrieve our blowing papers and books. We charged off in opposite directions: me to be late for class and she to where ever she was headed.
And, what about that "big, overgrown ass" comment? Well, I was, sort of. Not my ass, especially, but some of me was pretty big. By my second year at the university, I had reached six foot six in height and two-hundred and thirty-five well muscled pounds. I possessed really broad shoulders, a chiseled face, dark brown hair and eyes, a narrow waist, and although she could not see them, I also possessed a bigger than average cock and balls along with a near six-pack set of abs.
The next night, February 29th my fraternity was invited to a sorority house Leap Year Party. I decided at the very last minute to attend. I had a big exam the next day, but I decided, the hell with it, I'm tired of studying. So, I went.
About an hour into the party, I was at the buffet table where I picked up some hors d'oeuvres and a glass of punch, heavily spiked, I was told, and had started to turn around to my right to return to the other room. The up to now unnoticed girl on my right, just at the same moment, began her turn to the left to leave and we crashed. My drink was knocked into her and spilled all down the inside of her dress, soaking boobs and chest.
Yes, of course it was Jen. I caught the flaming red hair and the matching angry red face just as I also caught her drink, purposely tossed straight into my face! We both stood there, glaring at one another and dripping down our fonts.
Impulsively and deftly, I flipped an hors d'oeu'vre into the exposed cleavage (which offered a great deal of exposure) of her cocktail dress bodice. I used a hand to squish it around some, copping a great feel of her boobs in the process. She stood, dumbfounded, watching me until I with drew my hand.
She then reacted by slapping my face. I slapped hers just as quickly in a knee jerk response! Then we stood there and glared at each other again, silently daring each other to continue.
I slowly, calmly, picked up another hors d'oeuvre with a whipped cream top and, with Jen watching my every move, squished it against her mouth and forced it in. With equal agonizing slowness, she then did the same to me.
By that time, quite a few other guests stood in horrified, silent trances, looking on as we stood in a glaring face off, dripping punch and whipped cream. Everyone was afreaid to move; afraid they might set off a real physical battle between Jen and myself.
Time stood still for I don't know how long as we continued to stand with hands on hips, glaring at one another, literally nose to nose with our hands on our hips, silently daring the other to keep it going, not wishing to be the first to give in and quit.
Suddenly, smacking my lips on the gooey cream on my lips, I started to chuckle, Jen started to giggle, and then we both broke into laughter so hard we had to hold our sides. Tension abating, the onlookers also began to laugh.
"We seem to keep bumping into each other," I said.
"Yes," Jen replied, "shall we kiss and make up?"
By now we had semi collapsed in spasms of laughter with my hands on her shoulders and her hands on my shoulders, foreheads touching. We looked into each other's eyes and--we kissed. It was an amazing kiss that just kept going, and going, and...
We finally broke apart when the loud applause began to register in our heads. We both grinned at each other and the crowd and then Jen said, "Let's go up to my room and see if we can get cleaned up a bit. Come on."
With that, Jen took my hand and led me out and up some stairs in the hallway to the upper floor. After unlocking the door, Jen led me into her room, reclosing and I noted, relocking the door.
"My name's Jennifer, but you can call me Jen," she said, "what's your name?"
"Jake, but you can call me Jake."
"Well, Jake," she laughed, "let's get that shirt and tie off and stashed in my dirty clothes bag."
So, off came my tie, dress shirt, and Tee shirt, leaving me bare to the waist, exposing those broad shoulders and near six-pack abs. Not wasting anytime after disposing of my stuff, Jen, standing right in front of me, face to face, then dropped her cocktail dress off her shoulders and let it drop to puddle on the floor at her feet.
With a big grin at me, Jen next unhooked her soaked and gooey front closing strapless bra and let it drop, baring herself to her waist to match me.
Those very lovely melons of hers suddenly began sprouting erect nipples. Jen slipped off her heels and then walked up to me saying, "Jake, I think I like you--a lot, even if you do make me so damned mad sometimes."
We were instantly into a tight clutch, her perky, firm boobs crushed against my chest, her erect nipples so hard they nearly broke my skin. Our mouths lip locked in a long and passionate kiss. Any whipped cream that remained after our kiss downstairs, disappeared now in a flash.
Breaking the kiss, Jen stood and shed her half slip, leaving her in just the skimpiest of panties and a garter belt with attached black thigh highs. Her nipples continued to protrude in erect anticipation.
She advanced on me and dropped my pants and boxers before I could blink. My shoes and socks went with them. My large boner sprang out to full attention as Jen kneeled in front of me to stroke my shaft and lick my purpling shaft helmet.
Her tongue dipped into the opening of the helmet to lick up the precum oozing out into the open. She put her mouth over the helmet and inched downwards with my hands curled in her hair, helping to force her head down further and tighter against me until her nose brushed into my pubic hair.
"Ohhk," I groaned, as Jen gave me the first blow job of my life. It wasn't the last "first" that night, either;
After Jen cleaned my dick, I picked her up and carried her to the bed. I laid her down on her back and climbed up between her legs. Although I never done this before, I seemed to know what to do by instinct, and when I didn't, Jen coached me quite well.
Now it was Jen's turn to groan as I kissed and licked around on her neck, ears, and face as my cock rubbed her just below knee level becuase of our highth differential.
Mky God. Could she ever mewel and groan. I backed down some more to start on her gorgeous, large and all natural boobs with my mouth, sucking one nipple with my thumb and forefinger of a free hand working on the nipple of her other boob.
"Ohhh, yes!" she cried. "Yeesss."
When I removed my face and hands, Jen yelped., "Oh, God! don't stop now!"
"I don't intend to," I hoarsely replied. 'Not on your life." What I did do was move down to her feet and then kiss my way up her ankle, calf, and thigh towards the apex of her legs, ever so excruciatingly and slowly.
"Oh, Christ, Jake, don't tease me like that, FUCK ME!"
I paid no attention to her plea but continued kissing up to her pubic mound, which received one light kiss as I moved over to the other leg and proceeded down to her other foot, equally slowly. Jen was by then bucking her hips like a rodeo bronc. Then I started back up to the apex again.
"Oh, for God's sake Jake, I'm dying! Quit teasing and FUCK ME!"
When I got back to the top, without warning, I suddenly grabbed a mouthful of nether lips and ran my tongue up the slit to her clit and nibbled on what I found. I grabbed a bite hold on that clit and Jen exploded into rolls of orgasm for a full two minutes, one after the other which included a niagara squirt of pussy juice into my face.
"Oh shit, oh shit, OHHHHH SHIT!" Jen managed to croak out."
Jen had not quite subsided from her high before I finally ripped her miniscule panties off and totally out of the way, mounted her, and pushed my cock into her to the hilt in one, swift thrust. She was so wet with anticipation that I slid in easily.
"Ohhh, Unh," was her only exclamation.
She didn't need to coax or coach me on that one. I pumped slowly at first, but then faster and faster. I was so horny and ready that I came fairly quickly, blasting a load of cock cream deep into her pussy as Jen blasted off at the same time with another round of rolling orgasms.
"Well," I gasped, sweat dripping profusely from my face and chin, "there, (sigh), goes my uh, virginity! Damn! I uh, could do this uh, all night, oohhh, I think!"
"Damn!" panted Jen, "I uh, really do think uh, oh God, Jake that was the best ever. And uh, you say you've uh, never done this before?"
"Nope, first time," I answered, as my cock finally deflated enough to make a loud sucking noise as it dropped free of Jen's pussy.
Jen turned and began slurping my dick clean of our combined juices. When she was done, we lay on our sides and I spooned up against her back as we lay in post coital bliss with our combined sex fluids slowly trickling out of Jen's heavenly gate.
After about twenty minutes or so of this, I reached up and played with Jen's nipples again. "OH, recharged again, are we?'
"I think so, yes," I said as my cock began to rise against Jen's leg, "yes, I really do think so."
"Well, I want it in the butt this time," said Jen as she got on all fours and stuck her ass into the air while she tucked her head into a pillow.
My dick was now at full mast again and I rubbed it up and down Jen's slit, lubing it up with our combined sex juices still leaking from her pussy. When I was thoroughly slicked up, I centered my cock on her rosebud and slowly attempted to push in.
At first, I got nowhere. But I used my finger to smear more juices on the target and managed to open her with my finger and smear some inside. My next try with my cock got the head through her sphincter and inside. Jen grunted with pleasure and some pain. I continued to inch forward slowly until I was once again buried to the hilt.
"My virgin ass," Jen cooed, "you're the first there!"
I stopped and just rested, savoring the tight grip Jen had on my cock and she savored the filled up feeling of my fully expanded dick deep inside her. I slowly pumped in and out, barely moving at first, but slowly increasing the speed until Jen yelled, "Fuck me, Fuck me fast and hard, give it to me."
So, I did, until once more I felt the cream rise and blew a load of it into her butt. Jen had been working her clit while I gave her ass a reaming and she followed me with another of her series of orgasms. I backed out and we collapsed side by side again on the bed.
"Shit," said Jen, "I rarely have a multiple orgasm and never have I had three separate and rolling orgasms, one for each hole. And you have never done this before! Fucking amazing!"
"Nope, before tonight, I was a virgin for all three, anal, oral, and vaginal."
"Jesus, I don't know how you learned to do it so well then. Anyway, I'm certainly not going to turn loose of you very soon you fucking stud."
She climbed out of bed to get my fraternity pin and climbed back into bed, pinning it to her pillow for now as I climbed back aboard, missionary style, and fucked her again.
And she didn't, either. Turn loose of me, that is. We remained together until our graduation three years later. We fucked like minks most of that time, sometimes, both day and night. How we kept our grades up, I'll never know, but we did.
I also retained my voyeuristic nature at heart and a voyeur of opportunity in practice. Jen and I usually were naked in our by then off campus apartment. I liked her that way and she liked to indulge me. It helped promote spontaneous fucks.
Rather late in our relationship, I found out that Jen came from and Eastern, blue-blood family and sort of broke the traces by attending the University of Michigan rather than Vassar or some such high society school back east.
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