Chapter Good:
Sandy
PREFACE:
I’m taking a new direction, here. My stories will still be graphic, raunchy and all the other good stuff, similar to the 80 stories I’ve previously posted. Yet, most of those tales, largely set aboard my full-time liveaboard Love Boat, were largely pure fantasy. A few were loosely based on real life encounters, but, by-and-large, they were basically only a tawdry substitute for the total lack of sex in my life.
I still live aboard; I still don’t have sex with anyone except Ms. Michigan (inside joke – the state is shaped like a mitten). When I’m not watching porn to satisfy myself, I close my eyes and visualize about past actual encounters with prior lovers. I’ve had good, better, and best. With your indulgence, I’d like to share a few recollections of my times before moving aboard my Love Boat. Please believe me when I tell you that all these encounters actually happened in real life. A few details might be obscured by my failing memory but otherwise every one of these stories is true.
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The first few years of my married live were textbook perfect. Beautiful wife, cute dog, white picket fence, big house in a very upscale neighborhood … we were living the so-called “American Dream.” We had a sedate but workable sex life. Then we decided to have children. My wife got pregnant soon yet miscarried early. After that, try as we might, it was not to happen again. Years of fertility testing, basal body temp, fuck on demand, rush to Dr., jackoff in a cup in the Dr. office, numerous rounds of artificial insemination. Our inability to conceive was never officially diagnosed.
I recall driving home from the Dr. office discussing our options with my wife. She remarked that she didn’t want to end up in a rocking chair on the porch without grandkids. So, we started the adoption process. We ultimately adopted two S. Korean infants (3 mo. and 6 mo.) two years apart.
The years of fertility testing and the arrival of infants basically deleted any sex life that we had enjoyed. Sex became either non-existent or merely perfunctory, twice a year. No spontaneous blowjobs, no pussy licking. Just a missionary labor of love. I jacked off constantly. I was so horny that I got it down to a quickie science. I could rub one out just about anywhere in no time flat. Of course, spanking the monkey only lasts so long and the urge and returning boner soon call for another fix.
After years of no sex, I was desperate. I worked at a huge international Fortune 10 company. I was in the real estate department, staffed with 10 – 15 people. There were 3 females, all attractive and approachable. One, Sandy, was the cutest little thing. Petite, long hair, late 30’s, pleasingly plump, flirty. She sent out that unmistakable sex vibe. It turns out that she was fucking one of the draftsmen. He was married, a swinger, and had sex parties at his suburban home. I never attended one, but she did, several times.
On a few occasions, a group from work would meet for drinks at the local bar. One time, Sandy sat right across from me, her draftsman side piece way down at the end of the table. After some small talk, I suddenly felt her stocking feet between my legs, rubbing my crotch. Whoa!! It seemed to come from nowhere but the look she leveled at me told me differently. After another drink or two, I convinced her to go to my car to “talk.” We got right to it, kissing like kids, grabbing tits, reaching for belt buckles. She freed my rock-hard cock from my pants, leaned over and took his swollen head into her warm mouth. OMG. I hadn’t had a mouth on my dick in years!! It felt so fucking good.
She started working her head up and down on my stiff shaft, taking in a bit more with each stroke. She had a nice touch and knew how to use her tongue. She’d take 4 or 5 inches in, withdraw and do it again, over and over. Then she’d stop, spit on him, and plunge her mouth back down on him. She got me right to the edge and pulled away, slurping and panting. I needed more so I asked her: “Do you know the difference between like and love? One spits; the other swallows.”
With that, I grabbed her face in my hands and started kissing the hell out of her sloppy mouth and squeezing her boobs and nipples. Then I pulled away and forced her head back down on my boner. She got the message and began thrusting her mouth deep on my cock as she cradled my balls in her hand. Within moments, I exploded, shooting hard ribbons of thick cum on her deepthroat door. After 4 or 5 spasms, she pulled her mouth away, licked her lips and swallowed it all. My first blowjob in years and I got to cum in her mouth. Exquisite!!
Over the next year or so, just Sandy and I would very sporadically meet for drinks, ending up in my car for sex. Sometimes she’d let me finger fuck her. She’d pull her skirt up, panties aside and let me ravish her cunt with as many fingers as I could ram in there. She said she liked really fat cock, so 4 fingers became the norm. As soon as I had all four fingers lubed up and sliding in and out, I’d pound my hand as far up her slit as I could get it sitting in a car. I’d always get her to climax. I knew because she’d always squeeze her thighs together when she came, and her crotch got all wet.
One time, we went out for lunch. I had two dirty martinis and we talked about sex. She told me that she had been married once before. Her ex used to fuck her in the ass constantly. Like several times a day. Every day. The martinis gave me an idea. Between the restaurant and our office, there was a seedy, run down, by-the-hour motel. She was driving and I told her to pull into the motel. Much to my surprise, she did. I bought an hour and we disappeared behind closed doors. I sat in the chair and told her I wanted to watch her masturbate. She obliged by pulling her skirt up and lying on the bed. She pulled her panties aside and began stroking her vagina, inserting one finger at a time, getting them lubed up. Watching her stroke herself got my blood flowing so I moved over to the bed to assist.
I leaned over and started kissing her passionately. I placed my hand on the back of hers and synchronized our motions. I’d stick my middle finger deep in her cunt, then use the juices to lube it as I pushed it into her anus. Soon I had three fingers stroking her asshole. I couldn’t stand it any longer; I needed my dick in there. I quickly dropped my pants and crawled between her legs. She rocked her hips up to give me direct access. Her years of practice paid off.
I spit on my hand to lube my rod and pressed it against her ruby red target. This was a well-used hole. It didn’t offer any resistance, none at all, and my cock slid right in. First the glans, then the frenulum, then the shaft. All of it, balls deep. Her asshole could easily have accommodated more dicks or something much bigger. There was a lot of play left in that hole. I’ve fucked both very tight assholes and big Bertha’s like Sandy’s; they’re equally nice to fuck.
Being a pro at getting her ass fucked, she folded her legs back as high as she could and let me mount her proper so that I could piledrive my cock, hard pounding her wide-open hole. It was thrilling and I didn’t want it to stop. I kept slamming my groin into her crotch as long as I could. Suddenly, though, my orgasm came on very fast. As I spasmed the first shot of jism, I stopped and held my whole cock deep in her hole. Withdrew and repeated for the second and third spasm. After shooting my load up her ass, I left my shrinking dick inside as I caught my breath.
After that episode, I left that job, but I kept her number. A few years later, I had one other run-in with Sandy. She had moved, bought a new house. I invited myself over one lunch hour to see it and, hopefully, get to fuck her nice asshole again. I even took a house-warming gift of a bottle of champagne, thinking that would grease the skids. Much to my dismay, it was a washout. She said NO to all my ideas. No champagne. No going upstairs for some hanky-panky ass fucking (she didn’t want any more skeletons in her closet!). No bend over the kitchen stool for a quickie. Not even a blowjob. C’est la vie. Win some; lose some.
I don’t recall ever seeing Sandy again after that although I’ve relived fucking her in the ass in the motel room numerous times.
