Chapter 25: Jill

I had always been sexually active growing up and nothing changed as I grew older and supposedly wiser. If anything, I got more imaginative. This brings us to this place in time:

My hometown had just too many bad memories for me, so I took up another line of work.

I met Jill as a trucker. Pulling into a truckstop in Los Angeles, I sat behind the wheel thinking how boring a night on the lot would be. Thinking of the possibilities, I dollied down my trailer and prepared to bob tail 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 rather tiny little woman, just at 5’ tall, slender, with small, firm little breasts, and a waist I could circle easily with two hands. Once in the truck, she noticed the sleeper. ‘85 fully customed KW AntEater, I’d had this truck made to my personal 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. In about a minute, we were both nude and exploring each other’s body. With me still sitting, Jill swung a leg over my thighs 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 slightly less than 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 were 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 to always 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 cubbyhole 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.”

Hmm, 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, like she’d gone into rigor mortis, she came ... and cum she did. My entire crotch and the towel under me was soaked. Jill was a rainmaker, a woman that squirted when she came. In all my adventures, I’d heard of them but had never ran across a real one. When she’d finally showed some signs of life, her arms went back around my neck and she kissed me like 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 really 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 north of here, me here on a run and her down for a banking conference. True – Jill was a bank VP here for a week long conference but due to head back north in two days. We made plans to just head for the truckstop 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 to hit 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 off time together, getting to know one another and planning to meet up at home. A week later, I parked the truck in a truckstop 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. The owner of the shop I’d certified through was very sorry to see me go. I had a satellite shop in the rear of a family business and set sales records for the entire certifying organization. [A whole different story, not needed to do more than mention here] After listening to my answering machine, one offer definitely caught my attention. About half again more than I made as a trucker, all expense paid trips out of the country at least every 6 months and weekends at the beach with my classes. I would have no trouble getting rid 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 actually 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 day were a flurry of moving, calling the dive shop, arranging a meeting with the owner to hammer out a contract we could both live with. I had a reputation with the agency of being a top salesman and had run retail businesses in the past. We met, agreed on the terms and sent it to a lawyer for finalization. Jill was thrilled she had a live-in lover but something kind of dug at her mood at times.

During the exploratory time early in the relationship, I couldn’t help but notice that something troubled her. I asked, several times. Eventually, she sank into kind of a 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 working 2 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, 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 clammed 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, and to make matters worse, her relatives made her feel like it was all her fault. They told her if anyone, anyone at all found out, she’d be put in a foster home and her mom would end up in prison.

Jill would be a wild woman for about 10 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. Actually, 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 out wilder ways to satisfy each of us. We read an ad in the LA Times about a swing club out near Huntington Beach.

Calling, we made an appointment for a ‘personal’ interview. Hmm, did they want to see the goods before they took our money? I’d never been auditioned for sex before. Getting there on a Friday afternoon, we were shown into a nice office by the man of the house and given long forms to fill out - questionnaires asking about our sexual history, preferences and/or 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 just 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, fairly regularly. She went on to ask if it would bother me to make love while others were present, because a few members like to watch as or before they chose a playmate. Again, I told her no, I had no problems with public sex provided the setting was discreet. Holding my 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 said “Shall we?”

Watching Jill ride this guys 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 me dripping pussy and started slowly moving 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 to her 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 totally 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, am ready for another bout.

“Marvelous!” she exclaimed, “So you’re all about the woman’s pleasure then?”