A Time in my Life
By hellraser101.
I met Jill as a trucker. Pulling into a truck stop in Los Angeles, I sat behind the wheel, thinking how boring at night on the lot would be. Thinking of the possibilities, I dollied down my trailer and prepared to bobtail into the city and try to find a club with some action. I’ll cut to the chase here and tell you I found an attractive woman sitting by herself, nursing a drink. One thing led to another – dancing, drinking, and she finally got around to asking me what I did for a living. When I told her I was a trucker, she became intrigued. When I mentioned my truck was in the parking lot, she immediately wanted to see it.
I unlocked the door and had to help her up into the cab. I should mention that Jill was a relatively tiny little woman, just 5’ tall, slender, with small, firm little breasts and a waist I could circle quickly with two hands. Once in the truck, she noticed the sleeper. I’d had this truck made to my specs. Queen-sized bed, clothes closets, sink, microwave, color TV, and a dynamite stereo system, not to mention blue mood lights around the ceiling.
Jill walked back to the bed and sat down, then patted the mattress beside her. I didn’t need a written invitation by that point. We were nude and exploring each other’s bodies in about a minute. Jill swung a leg over my thighs with me still sitting and straddled me with her arms around my neck. As I played with her tight little breasts, she reached down and guided me into her sopping cunt, sliding closer to my groin to get as much of me into her as possible. At 7”, I’m not a huge guy, with my penis being only a little over an inch & 1/2 thick, but a guy uses what one has….
Jill started hunching away as I tongued her erect little nipples. Part of my mind was surprised that each of her nipples was slightly larger than a dime, with her hard points only barely larger than my own. It was hard to suck the nipples themselves due to their size, so I pulled as much of her breast into my mouth as I could, keeping my tongue busy on the stiff little point.
Jill’s eyes were nearly rolled back into her head, lots of white showing. She pulled back and asked me if I had a towel handy. I thought it was a strange time to be asking that. I was gentleman enough always to offer warm, wet washrag after the deed, never before the culmination. I told her sure, and with her still impaled on me, I reached into the little cubby-hole beside the sink and grabbed a hand towel.
“Do you want me to wet it?” I asked.
“No, put it under you when you sit back down. I think we’re going to make a mess.”
I’d had women who creamed copiously as they got excited but other than running down their ass, no big deal. Oh well, she was running the show.
Jill started making mewling noises, and her bouncing and grinding became more pronounced when suddenly she leaned back, pushing herself onto me to the point of actually bruising my pubic bone. Stiff, as she’d gone into rigor mortis, she came, and cum she did. My entire crotch and the towel under me were soaked. Jill was a rainmaker, a woman that squirted when she came. In all my adventures, I’d heard of them, but had never run across one. When she’d finally showed signs of life, her arms went back around my neck, and she kissed me as her tongue would either go down my throat or punch through the back of my neck.
I did eventually get her the wet washrag, and I think this impressed her somewhat. Strangely, she didn’t want to lie down on the bed but asked if it was ok to just sit up front in my air-cushioned seats in the nude. Damn, an exhibitionist streak to boot. BONUS! We talked about where we were from. Talk about coincidence. We were both from the same city in the upper Northwest, me here on the run and her down for a banking conference. True – Jill was a bank VP here for a weeklong conference, but due to head back north in two days.
We just made plans to head for the truck stop where she planned to spend the night with me. After making love to her tight, diminutive body several times through the wee hours, she never failed to squirt about a cup of liquid every time she came. To myself, I was thinking of hitting Walmart for some plastic shower curtains. Anything long-term with this woman would make my laundry bill go through the roof.
We spent most of her remaining time together, getting to know one another and planning to meet at home. A week later, I parked the truck at a truck stop at home and planned to spend the next couple of weeks getting to know this little lady.
Before buying a truck, I’d been a SCUBA instructor for many years. The agency I certified for kept trying to get me to take a management job at one of the many franchises, especially along the California coast. After listening to my answering machine, one offer caught my attention. About half more than I made as a trucker, all-expense-paid trips out of the country at least every six months, and weekends at the beach with my classes. I would have no trouble getting rid of my year-old Kenworth conventional.
Meeting up with Jill, we had dinner at a nice restaurant, and I sprung my plan on her. Taking it all in, she was quiet for a bit, then looking me in the eyes, she asked, “Shall we just move in together?”
I hadn’t planned that far ahead, but the thought appealed to me. “Sure. We seem to get along great, and I suppose we can acclimate to each other as we go.”
The next few days were a flurry of moving, calling the dive shop, and arranging a meeting with the owner to hammer out a contract we could both live with. I had a reputation with the agency as a top salesman and had previously run retail businesses. We met, agreed on the terms, and sent it to a lawyer for finalization. Jill was thrilled she had a live-in lover, but sometimes, something dug at her mood.
During the exploratory time early in the relationship, I couldn’t help but notice something troubling her. I asked several times. Eventually, she sank into a kind of depression. She had a past and possibly a secret that weighed on her mind. I took her hands in mine and told her there was nothing she could have done before that would make me care for her any less. This led to a bawling, sobbing tale of her childhood.
Growing up, it seems her mother was divorced with a nine, ten, and eleven-year-old at home, very little money, and Mom was working two jobs to keep a roof over their heads. Her mother had made a deal with her brother and his wife to watch the kids in the evenings. Their end was that they were only willing to take one child per night, and the other two would have to either go to an evening daycare or find a neighbor to watch them. Jill kind of clams up at this point. A rough situation to grow up in, but not exactly terrible.
Coaxing her on, she finally admitted that her uncle and aunt had initiated her into sex at age nine. At that tender age, she’d not only had full penetration, learned to deep throat, ate pussy, and had her own licked but was also introduced to the family dog. Quite a load for a nine-year-old; to make matters worse, her relatives made her feel like it was all her fault. They told her she’d be put in a foster home if anyone found out.
Jill would be a wild woman for about ten months at a pop, then go into these depressions again for a few weeks. Hard to live with, but I eventually learned to read her moods. I got the hint after having my hand and arm nearly ripped off and beaten about the head and shoulders with it. After confessing her sexual awakening, Jill became a wild woman – always wanting a bigger high, so together, we sought wilder ways to satisfy each of us. We read an ad in the LA Times about a swing club near Huntington Beach.
Calling, we made an appointment for a ‘personal’ interview. Did they want to see the goods before they took our money? I’d never auditioned for sex before. Getting there on a Friday afternoon, we were shown into a lovely office by the man of the house and given long forms to fill out – questionnaires asking about our sexual history, preferences, and any kink we were into. Next came a release form, holding the club harmless in case of a civil dispute or diseases we might be exposed to.
Next, what later turned out to be the guy’s wife came into the room and asked me to join her in the other room. Once there, she asked me to disrobe as she did the same. Nude, she stepped into me and ran her hands over my chest until she reached my erect penis. She slowly stroked it and asked if my wife got jealous or if I were jealous of her with other men.
At this point, I corrected her thinking, telling her we were living together, and no, neither of us had a problem that I was aware of. She asked me if I’d ever been aids tested, and I told her yes, reasonably regularly. She asked if it would bother me to make love while others were present because a few members like to watch as or before they choose a playmate. Again, I told her no, I had no problems with public sex provided the setting was discreet. Holding me by my stiff dick, she led me through another door where Jill was writhing on top of her husband.
The woman looked at me and asked, “Shall we?”
Watching Jill ride this guy’s fat dick excited the crap out of me, and I pulled our host’s wife down into the same position as Jill. The woman guided me into her dripping pussy and slowly moved up and down. Soon, she leaned over my chest to ask me if I liked oral and anal or just plain vanilla sex. Playing with her taut nipples, I whispered that although I liked getting head, I seldom climaxed from it. As for anal sex, bring on the lube!
I also explained that I got a tremendous high from fucking in any style and didn’t always climax from it. She thought that was strange, but I told her my reasoning- I get involved in the penetration, feeling a woman’s vagina or rectum squeezing my hard dick, but part of my brain tells me when I get my nut, it’s all over for a while. As it is, I can go as much as an hour without cumming, and after a physical rest of a few minutes, I am ready for another bout.
“Marvellous!” She exclaimed. “So you’re all about the woman’s pleasure, then?”
“My old daddy told me, Son, take care of the woman, and somewhere along the way, you’ll get taken care of too, and the lady will always ask you back.”
I’ve lived by those words since puberty. The woman ground herself hard on my pubic bone, rubbing her clit as she did. Her breath came in short gasps, and she stiffened. As her climax passed, I could feel her cunt rippling and milking my dick. She lay down on my chest, still impaled on my hard dick.
Jill had ridden this woman’s husband to its inevitable conclusion, and both were wiping up the mess with a towel. The lady I had been with asked to excuse them, so Jill and I went back into the interview room. Shortly, both came out and welcomed us both to the club. The manager asked if we had a problem watching the other make love to a stranger. We both laughed, saying why else we would join a swing club if it weren’t for strangers –strange pussy and strange dick? The pair just smiled and asked us if we were up for anything.
“Define anything?” I asked.
The man said Jill was a remarkably avid and demonstrative lover and thought their members would enjoy the time spent with her. Jill was beaming by this time. The guy’s wife spoke up and said the women in the club were in for a treat being with me, as I had no hang-ups about sex. They both looked at each other.
Then the man spoke, “Would you, as a couple, like to help us with new member applicants? Many come in, mostly men with their wives and the man is all bullshit about ‘yeah, we talked it over, and we want something to spice up our life. Generally, when the hubby talks/coerces the wife into going along with the idea, one of two things usually happens. The wife goes bug-nuts seeing her hubby balls deep in another woman, or the hubby goes green with jealousy. Either thinking, the other may have found a replacement for them.
“We’d like you to chat with them as a couple, then feel them out and discover their real motivations. If it looks like one is pushing the other to do it, it’ll never work out, and the last thing we need is a domestic quarrel in the middle of mass lovemaking, don’t you agree?”
I could see that very thing happening, so after whispering to Jill, I told them yes, we’d be happy to escort the noobs. Our first club meeting was on the following Friday night, and our hosts took us to the side and explained a few details they hadn’t mentioned in the interview, and we’d had no clue to ask about.
“We forgot that we have a catered meal every Friday and Saturday night. Everyone is to remain clothed until the caterers leave. Eating is confined to the meeting room, which is more or less a massive pit in the middle of the house. Once people are seated and eating, I make club announcements. Afterward, I also remind everyone to use the lockers in the long haul. Smoking is allowed as long as people use the ashtrays.
“By the way, 90 to 120 couples are often here each weekend, so variety is just about boundless. New couples come with members they may or may not have partied with, so your job is to vet these noobs, as we spoke about earlier. If they pass your criteria, escort them into the club, otherwise, notify one of us, and we’ll gather their hosts and tell them the new people aren’t ready for this.
“One thing I want to make clear… NO DRINKING, NO DOPE. Tell us if you see or suspect someone is under the influence, and they are history. It’s not hard for you to imagine the hassles and the trouble involved with loaded members. We run a quiet house and want to keep it that way.”
Wow! I was impressed. This was not your typical orgy. Jill and I couldn’t wait to get started. We saw or participated in about anything two or more people could do together. If you could imagine sex without violence or jealousy, this was the place to be.
Time to move along. Jill was still on again/off again in the sex department, and if I had to hazard a guess, I think she was bipolar. Sadly, if you want to call it that, I was the only person who knew her secret for a few more months.
We’d received an invitation to Jill’s stepsister’s wedding. The couple decided on an open-air affair in San Diego, followed by a reception on a huge paddle wheeler. Jill’s older brother and sister attended also, and Jill was in one of her depressions, RIGHT after seeing her aunt and uncle walk by. I’m a people watcher by habit, and I watched the sister and brother closely as they noticed the relatives. Both faces went through an array of emotions, mostly fear and anger. I leaned over to Jill and told her I thought her secret could also be her siblings’. She just shivered and started crying. Noticing this, her brother and sister got very concerned. Deciding Jill would never broach the subject, I launched right into it.
“Neither of you has to give me a yes or no answer, but how many years did your aunt and uncle molest you?”
You could have heard a pin drop even out in the park as we were. Big sister looked at big brother and started crying, and in a few minutes, both hugged Jill and each other.
“I thought I was the only one,” said the brother.
“They both told me I was the special one, and it was a big dark secret that they’d never tell mom what a nasty girl I was.”
Jill got a mean look and stood up.
“What do you have in mind, hon?” I said
“This is something Mom needs to know. She thinks the sun sets in both their asses,” and off she marched in search of her mother, the other three of us close behind.
Her mom liked me and probably considered me son-in-law material, but this wasn’t my story to tell, so I hung back, just in hearing range, when they confronted her.
Their mother asked a few questions of each in a tight voice, then stomped off in search of her brother and his wife. We later learned she confronted them right before all the wedding guests; of course, they denied everything. However, Jill’s mom also told them there were now three witnesses to their little act. Go and never come around any of her family again, or she’d go to the cops.
*****
We’d moved into a duplex a year later, and life was again back to the old sexual roller coaster. However, her fits of depression seemed to last longer as time passed.
One afternoon, Jill was in her ON mood, and I ate her pussy for all I was worth. I knew she liked to have me lick her from asshole to clit, as this gave her the whole feeling. I might mention we’d never tried anal sex to this point. Sixty-nine and vaginal sex was plenty. Jill gasped out that she needed something more – to be filled up. Not wanting to lose my source of pussy nectar, I slid a couple of fingers into her hot hole while nibbling on her clit.
“More, I need more… Please!”
Being the considerate lover I am, I slid two more fingers into her slick cunt. She started hunching on my fingers, latching up, so I bent my thumb into my palm. POP! My whole hand disappeared into her pussy. I unclenched and clenched my fist inside her, only pulling back and pushing in a couple of inches. Jill’s head was rolling from side to side and babbling in some tongue known only to her. Jill rolled over on her hands and knees, and I started to withdraw my hand.
“No, don’t you fucking take it out!”
Ok, I could do that – this was her rodeo, after all.
She rocked back on her knees, driving my fist further inside her and nearly breaking my wrist. Struggling, she got to her feet and told me to put my elbow on the bed. Once in position, she squatted onto my hand, impaling herself to the depths I thought would permanently damage her.
During regular sex, she was tight, deliciously so, but I’d seen her take 12-inch dicks as quickly as she’d taken mine. But still, I was concerned. After possibly two or three minutes of her squatting, she came like a fire hydrant, covering me and the sheets with her cum. She stood up and eased herself off my hand.
By this time, I was rock hard and ready to rumble as Jill lay on the cum soaked bed on her stomach. I pushed a couple of fingers inside her wet pussy only to find it stretched to the point I would barely feel inside her. A thought struck me – she had another hole and one I’d never tried. Scooping her thick juices off the inside of her thighs, I rubbed it around her puckered little ring. Surprisingly, it was soft and partly open, likely due to the intense climax she’d just survived.
One finger, then two… to my hand. I planned to plow her bowels if she could do this without pain. As I said earlier, I’m long but somewhat thin. I slid into her like it was a custom-made glove, just for me. After about a dozen slow strokes, from the tip of my dick right down to the balls, she rocked back on her elbows and knees, head down on the pillow. After a few dozen more, she started rocking backward to meet my thrusts.
Within a minute, she reached back, grabbed her ass cheeks with both hands, and pulled them wide apart, allowing me nearly another inch to put inside her warm channel. I let Jill do all the slamming, hanging onto her lower back, when suddenly, she came. In all the time we’d been together, I’d never actually watched her pussy as she came. I had to rock back and watch it jet from her cunt. If I didn’t know better, I could have imagined she was peeing instead of cumming.
Months passed, and fisting, followed by ass fucking became a regular part of our lovemaking, but another thing entered our lives.
I don’t remember who gave us a huge mongrel dog. Long-haired and standing waist-high to me, it dwarfed Jill. The dog was pretty easy to housebreak and fun to wrestle with. To my dismay, the bastard won more often than not. Jill was back in one of her moods, and we’d gotten into a terrible fight. I figured life was too short for this bullshit, regardless of the good sex, so I packed and left. Toby, the dog, went with me to a house I’d rented after only a day of looking. A week or two went by, and Jill called, apologizing for her mood and her life, wanting me to return. I liked the woman, but her on-again / off-again moods drove me crazy, so I told her no. She asked me if she could at least keep Toby for a while because she missed him.
I’m not hateful, nor am I a bastard, so I took Toby and a big bag of food over and told her I’d pick him up after returning from a diving trip to Cozumel in two weeks; besides, better for Toby than boarding him while I was away.
The trip was fun and relaxing, and I got acquainted with two ladies on the trip who didn’t mind sharing since they were roommates. Another story there, but for later. On arriving back at the airport, I drove my car to my old duplex to retrieve the dog. Jill wanted me to come inside and have a beer while I told her all about the trip.
After maybe an hour, the story was done, and I got up to gather Toby’s things.
“Want to see what Toby learned to do?” She asked.
“Have you been teaching my dog tricks?”
“Well, this is kind of a special trick. Hold onto him. I’ll be right back.”
Off she went to the bedroom while I loved up Toby. It’s nice when your dog is glad to see you. Jill came out shortly in one of my old button shirts and nothing else. Toby started whining and pulling away from me.
“What the hell is going on? What’s wrong with Toby, and why are you dressed like that?”
“Watch and see.”
With that, she dropped to her hands and knees, and ass stuck high into the air. Toby ran over and started licking her pussy, and I swear, I could see his long tongue swabbing her tonsils from the back side.
Jill patted her ass, and Toby jumped on her back, wrapping his forepaws around her tiny waist. I looked at his hindquarters; his cock was fully extended, possibly 8 inches long, and nearly as thick as my wrist. He took one lunge at her and buried his dick in her cunt to the base. Tail wagging, he started jackhammering her pussy, and I could watch his knot expands, banging into the lips of her pussy.
As Jill felt his knot nudging at her inner lips, she suddenly pushed backward, forcing his swelling knot into her pussy. I watched the two of them go at it for five minutes, and Toby collapsed on her back. A short while later, he started to whine and dropped a leg over her back, turning until he was ass to ass with her. I sat on the couch, watching her in awe until Toby took a step away from her, and she relaxed her pussy, letting him slide out.
We continued to date for about a year, but she moved to California, taking Toby with her. I’ve yet to meet another woman as sexually crazy as she was. I hope she finds her dream.
The End.
*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Remember, even the limited editing done here doesn’t always mean the narrative/plot flaws in a story are fixed. The opinions/views expressed in this story (and in any comments) are those of the author and do not represent this site. We support freedom of speech.
